WO2022267839A1 - Organic compound, electronic component, and electronic device - Google Patents

Abstract

The present application relates to the technical field of organic materials, and specifically relates to an organic compound, an electronic component, and an electronic device. The organic compound having a structure represented by formula (1). When being used as an organic electroluminescent layer to prepare an organic electroluminescent device, the organic compound of the present application can effectively prolong the service life of the organic electroluminescent device and improve luminous efficiency.

Description

Organic compounds and electronic components and electronic devices

This application claims the priority of the Chinese patent application with application number CN202110699952.7 submitted on June 23, 2021, and the entire disclosure of the Chinese patent application is incorporated in this application by reference.

technical field

The application belongs to the technical field of organic materials, and specifically provides an organic compound and an electronic component and an electronic device using the same.

Background technique

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 becoming wider and wider. Such electronic components generally include a cathode and an anode oppositely arranged, and a functional layer arranged 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 located between the energy conversion layer and the anode, and an electron transport layer located between the energy conversion layer and the cathode.

Taking an organic electroluminescent device as an example, it generally includes an anode, a hole transport layer, an organic electroluminescent layer serving as an energy conversion layer, an electron transport layer and a cathode, which are stacked in sequence. When a voltage is applied to the cathode and anode, the two electrodes generate an electric field. Under the action of the electric field, the electrons on the cathode side move to the organic electroluminescent layer, and the holes on the anode side also move to the organic electroluminescent layer. The luminescent layers combine to form excitons, and the excitons release energy outwards in an excited state, thereby making the organic electroluminescent layer emit light.

At present, there are problems such as reduced luminous efficiency and shortened lifespan during the use of the organic electroluminescent device, which leads to a decline in the performance of the organic electroluminescent device.

Contents of the invention

In view of the above-mentioned problems in the prior art, the purpose of this application is to provide an organic compound, an electronic component and an electronic device. The organic compound can be used in an organic electroluminescent device to improve the performance of the organic electroluminescent device.

In order to achieve the above object, the first aspect of the present application provides an organic compound, the organic compound has a structure shown in formula 1:

Wherein, X is selected from O or S;

Het is a heteroarylene group with 3 to 20 carbon atoms;

L ₁ , L ₂ and L ₃ are the same or different, and are independently selected from single bonds, substituted or unsubstituted arylene groups with 6 to 30 carbon atoms, or substituted or unsubstituted arylene groups with 3 to 30 carbon atoms the heteroarylene;

Ar ₁ and Ar ₂ are the same or different, and are independently selected from hydrogen, a substituted or unsubstituted aryl group with 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group with 3 to 30 carbon atoms;

The substituents in L ₁ , L ₂ , L ₃ , Ar ₁ and Ar ₂ are the same or different, and are independently selected from deuterium, halogen group, cyano group, heteroaryl group with 3 to 20 carbon atoms, carbon Aryl groups with 6 to 20 atoms, alkyl groups with 1 to 10 carbon atoms, haloalkyl groups with 1 to 10 carbon atoms, cycloalkyl groups with 3 to 10 carbon atoms, and cycloalkyl groups with 2 to 10 carbon atoms 10 heterocycloalkyl groups or alkoxy groups with 1 to 10 carbon atoms;

Optionally, in Ar ₁ and Ar ₂ , any two adjacent substituents form a ring;

Each R ₁ , R ₂ , R ₃ and R ₄ are the same or different, and are independently selected from hydrogen, deuterium, halogen group, cyano group, aryl group with 6 to 20 carbon atoms, and 3 to 30 carbon atoms heteroaryl group, trialkylsilyl group with 3 to 12 carbon atoms, alkyl group with 1 to 10 carbon atoms, haloalkyl group with 1 to 10 carbon atoms, ring with 3 to 10 carbon atoms Alkyl, heterocycloalkyl with 2 to 10 carbon atoms or alkoxy with 1 to 10 carbon atoms;

n ₁ represents the number of substituent R ₁ , n ₁ is selected from 1, 2 or 3, when n ₁ is greater than 1, any two R ₁ are the same or different;

n ₂ represents the number of substituent R ₂ , n ₂ is selected from 1 or 2, when n ₂ is greater than 1, any two R ₂ are the same or different;

n ₃ represents the number of substituent R ₃ , n ₃ is selected from 1 or 2, when n ₃ is greater than 1, any two R ₃ are the same or different;

n ₄ represents the number of substituent R ₄ , n ₄ is selected from 1, 2, 3 or 4, when n ₄ is greater than 1, any two R ₄ are the same or different.

In this application, carbazole derivatives are fused through heteroaryl groups to form a large conjugated seven-membered ring, which can fix the configuration of carbazole groups and form a new mother nucleus, which can improve the planarity of molecules and make The rotation angle of other aromatic groups attached to the carbazole ring is reduced, thereby improving the carrier transport capability of the compound and the stability of the compound, and at the same time, it can adjust the HOMO/LUMO energy level of the compound to balance the transport efficiency of holes and electrons . The organic compound of the present application can be used as the host material of the organic electroluminescent layer, and can improve the luminous efficiency and lifespan of the organic electroluminescent device.

According to a second aspect of the present application, an electronic component is provided, comprising an anode, a cathode, and at least one functional layer between the anode and the cathode, the functional layer comprising the above-mentioned organic compound.

According to a third aspect of the present application, an electronic device is provided, including the above-mentioned electronic component.

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.

Description of drawings

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

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

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

Explanation of reference signs

100, anode; 200, cathode; 300, functional layer; 310, hole injection layer; 320, hole transport layer; 321, first hole transport layer; 322, second hole transport layer; 330, organic electro-induced luminescent layer; 340, hole blocking layer; 350, electron transport layer; 360, electron injection layer; 400, electronic device.

detailed description

Example embodiments will now be described more fully with reference to the accompanying drawings. Example embodiments may, however, be embodied in many 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 in order to give a thorough understanding of embodiments of the present disclosure.

In the drawings, the thicknesses of regions and layers may be exaggerated for clarity. The same reference numerals denote the same or similar structures in the drawings, and thus their detailed descriptions 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 in order to give a thorough understanding of embodiments of the present disclosure. However, one skilled in the art will appreciate that the technical solutions of the present disclosure may be practiced without one or more of the specific details, or that other methods, components, materials, etc. may be employed. In other instances, well-known structures, materials, or operations are not shown or described in detail to avoid obscuring the main technical idea of the present disclosure.

The application provides an organic compound, the organic compound has a structure shown in formula 1:

Wherein, X is selected from O or S;

Het is a heteroarylene group with 3 to 20 carbon atoms;

L ₁ , L ₂ and L ₃ are the same or different, and are independently selected from single bonds, substituted or unsubstituted arylene groups with 6 to 30 carbon atoms, or substituted or unsubstituted arylene groups with 3 to 30 carbon atoms the heteroarylene;

Ar ₁ and Ar ₂ are the same or different, and are independently selected from hydrogen, a substituted or unsubstituted aryl group with 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group with 3 to 30 carbon atoms;

The substituents in L ₁ , L ₂ , L ₃ , Ar ₁ and Ar ₂ are the same or different, and are independently selected from deuterium, halogen group, cyano group, heteroaryl group with 3 to 20 carbon atoms, carbon Aryl groups with 6 to 20 atoms, alkyl groups with 1 to 10 carbon atoms, haloalkyl groups with 1 to 10 carbon atoms, cycloalkyl groups with 3 to 10 carbon atoms, and cycloalkyl groups with 2 to 10 carbon atoms 10 heterocycloalkyl groups or alkoxy groups with 1 to 10 carbon atoms;

Optionally, in Ar ₁ and Ar ₂ , any two adjacent substituents form a ring;

Each R ₁ , R ₂ , R ₃ and R ₄ are the same or different, and are independently selected from hydrogen, deuterium, halogen group, cyano group, aryl group with 6 to 20 carbon atoms, and 3 to 30 carbon atoms heteroaryl group, trialkylsilyl group with 3 to 12 carbon atoms, alkyl group with 1 to 10 carbon atoms, haloalkyl group with 1 to 10 carbon atoms, ring with 3 to 10 carbon atoms Alkyl, heterocycloalkyl with 2 to 10 carbon atoms or alkoxy with 1 to 10 carbon atoms;

n ₁ represents the number of substituent R ₁ , n ₁ is selected from 1, 2 or 3, when n ₁ is greater than 1, any two R ₁ are the same or different;

n ₂ represents the number of substituent R ₂ , n ₂ is selected from 1 or 2, when n ₂ is greater than 1, any two R ₂ are the same or different;

n ₃ represents the number of substituent R ₃ , n ₃ is selected from 1 or 2, when n ₃ is greater than 1, any two R ₃ are the same or different;

n ₄ represents the number of substituent R ₄ , n ₄ is selected from 1, 2, 3 or 4, when n ₄ is greater than 1, any two R ₄ are the same or different.

In this application, the descriptions "independently selected from" and "independently selected from" can be used interchangeably, and should be interpreted in a broad sense. It can refer to the same symbols in different groups The specific options expressed do not affect each other, and it can also mean that in the same group, the specific options expressed by the same symbols do not affect each other. E.g,"

Wherein, each q is independently 0, 1, 2 or 3, each R" is independently selected from hydrogen, deuterium, fluorine, chlorine", and its meaning is: Formula Q-1 represents that there are q substituents R" on the benzene ring , each R" can be the same or different, and the options of each R" do not affect each other; Formula Q-2 means that there are q substituents R" on each benzene ring of biphenyl, and the R on the two benzene rings The number q of "substituents may be the same or different, each R" may be the same or different, and the options of each R" do not affect each other.

In the present application, the term "substituted or unsubstituted" means that the functional group described after 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" means an aryl group having a substituent Rc or an unsubstituted aryl group. Wherein the above-mentioned substituent, namely Rc, can be, for example, deuterium, a halogen group, a cyano group, a heteroaryl group with 3 to 30 carbon atoms, an aryl group with 6 to 20 carbon atoms, and an aryl group with 3 to 20 carbon atoms. 12 trialkylsilyl groups, alkyl groups with 1 to 10 carbon atoms, haloalkyl groups with 1 to 10 carbon atoms, cycloalkyl groups with 3 to 10 carbon atoms, and alkyl groups with 2 to 10 carbon atoms Heterocycloalkyl and alkoxy having 1 to 10 carbon atoms. In this application, the "substituted" functional group can be substituted by one or more than two substituents in the above Rc; when two substituents Rc are connected to the same atom, these two substituents Rc can be independently exist or connect with each other to form a ring with the atom; when there are two adjacent substituents Rc on the functional group, the two adjacent substituents Rc can exist independently or be fused with the functional group to which they are attached to form a ring.

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

In this application, in "any two adjacent substituents form a ring", "any two adjacent" includes two substituents on the same atom, and may also include two adjacent atoms having A substituent; wherein, when there are two substituents on the same atom, the two substituents can form a saturated or unsaturated ring with the atom connected together; when two adjacent atoms have a substituent respectively When , the two substituents can be fused to form a ring. For example, when Ar has more than ₂ (2 or more) substituents, and any adjacent substituents form a ring, the formed ring can be saturated or unsaturated, and the number of carbon atoms is 5- 14 rings, for example: benzene ring, naphthalene ring, phenanthrene ring, anthracene ring, cyclopentane, cyclohexane, adamantane, etc.

In the present application, the number of carbon atoms of a substituted or unsubstituted functional group refers to the number of all carbon atoms. For example, if L ₁ is selected from a substituted arylene group with 12 carbon atoms, all the carbon atoms of the arylene group and the substituents thereon are 12. Example: Ar ₁ is

Then its carbon atom number is 7; L is

Its carbon number is 12.

In this application, when no specific definition is provided otherwise, "hetero" refers to including at least one heteroatom such as B, N, O, S, P, Si or Se in a functional group and the remaining atoms are carbon and hydrogen . An unsubstituted alkyl group may be a "saturated alkyl group" without any double or triple bonds.

In the present application, the alkyl group may include a straight-chain alkyl group or a branched-chain alkyl group. The alkyl group may also be an alkyl group having 1 to 10 carbon atoms. The alkyl group can also be an alkyl group having 1 to 6 carbon atoms. Furthermore, an alkyl group may be substituted or unsubstituted.

Preferably, the alkyl group is selected from alkyl groups with 1 to 5 carbon atoms. 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 single ring and condensed ring structures. The cycloalkyl group may have 3 to 10 carbon atoms, and specific examples include, but are not limited to, cyclopentyl, cyclohexyl, adamantyl and the like.

In this application, aryl refers to an optional functional group or substituent derived from an aromatic carbocycle. The aryl group can be a single-ring aryl group (such as phenyl) or a polycyclic aryl group, in other words, the aryl group can be a single-ring aryl group, a condensed ring aryl group, two or more single-ring aryl groups connected by carbon-carbon bond conjugation. Cyclic aryl groups, single-ring aryl groups and condensed-ring aryl groups connected through carbon-carbon bond conjugation, and two or more fused-ring aryl groups connected through carbon-carbon bond conjugation. That is, unless otherwise specified, two or more aromatic groups linked by carbon-carbon bond conjugation can also be regarded as an aryl group in the present application. Wherein, the fused ring aryl group may include, for example, a bicyclic fused aryl group (such as naphthyl), a tricyclic fused aryl group (such as a phenanthrenyl, a fluorenyl, anthracenyl) and the like. The aryl group does not contain heteroatoms such as B, N, O, S, P, Se and Si. For example, in the present application, biphenyl, terphenyl, etc. are aryl groups. Examples of aryl groups include, but are not limited to, phenyl, naphthyl, fluorenyl, anthracenyl, phenanthrenyl, biphenyl, terphenyl, quaterphenyl, pentphenyl, benzo[9,10]phenanthryl base, pyrenyl, benzofluoranthene,

base, spirobifluorenyl, etc. The substituted or unsubstituted aryl group in the present application may contain 6 to 30 carbon atoms. In some embodiments, the number of carbon atoms in the substituted or unsubstituted aryl group may be 6 to 25. In some embodiments, the substituted or unsubstituted aryl group may have 6 to 25 carbon atoms. The number of carbon atoms in the unsubstituted aryl group can be 6 to 20. In other embodiments, the number of carbon atoms in the substituted or unsubstituted aryl group can be 6 to 18. In other embodiments, the substituted or unsubstituted aryl group can have 6 to 18 carbon atoms. The number of carbon atoms in the unsubstituted aryl group may be 6-12.

In the present application, the number of carbon atoms of the substituted or unsubstituted aryl group may be 6, 10, 12, 13, 14, 15, 16, 18, 20, 24, 25 or 30.

In the present application, biphenyl can be understood as a phenyl-substituted aryl group, or as an unsubstituted aryl group.

In the present application, an arylene group refers to a polyvalent group formed by further losing one or more hydrogen atoms from an aryl group.

In this application, the terphenyl group includes

In this application, the substituted aryl group can be that one or more than two hydrogen atoms in the aryl group are replaced by such as deuterium atom, halogen group, cyano group, aryl group, heteroaryl group, trialkylsilyl group, alkyl group, Cycloalkyl, alkoxy and other groups are substituted. It should be understood that the number of carbon atoms of a substituted aryl group refers to the total number of carbon atoms of the aryl group and the substituent on the aryl group, for example, a substituted aryl group with 18 carbon atoms refers to the aryl group and its The total number of carbon atoms in the substituents is 18.

In the present application, the fluorenyl group may be substituted by one or more substituents. Where the above fluorenyl groups are substituted, the substituted fluorenyl groups may be:

etc., but not limited to this.

In the present application, specific examples of aryl as a substituent include, but are not limited to: phenyl, naphthyl, anthracenyl, phenanthrenyl, fluorenyl, biphenyl and the like.

In this application, heteroaryl refers to a monovalent aromatic ring or its derivatives containing at least one heteroatom in the ring, and the heteroatom can be at least one of B, O, N, P, Si, Se and S. The heteroaryl group can be a monocyclic heteroaryl group or a polycyclic heteroaryl group, in other words, a heteroaryl group can be a single aromatic ring system, or a plurality of aromatic ring systems connected by carbon-carbon bond conjugation, and any aromatic The ring system is an aromatic single ring or an aromatic fused ring. Exemplary, heteroaryl groups may include thienyl, furyl, pyrrolyl, imidazolyl, thiazolyl, oxazolyl, oxadiazolyl, triazolyl, pyridyl, bipyridyl, pyrimidyl, triazinyl, Acridyl, pyridazinyl, pyrazinyl, quinolinyl, quinazolinyl, quinoxalinyl, phenoxazinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyridine Azinyl, isoquinolyl, indolyl, carbazolyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothienyl, dibenzothienyl, thiophene Thienyl, benzofuryl, phenanthrolinyl, isoxazolyl, thiadiazolyl, benzothiazolyl, phenothiazinyl, silfluorenyl, dibenzofuryl and N-arylcarbazole Base (such as N-phenylcarbazolyl), N-heteroarylcarbazolyl (such as N-pyridylcarbazolyl), N-alkylcarbazolyl (such as N-methylcarbazolyl), etc., It is not limited to this. Among them, thienyl, furyl, phenanthrolinyl, etc. are heteroaryl groups of a single aromatic ring system type, and N-phenylcarbazolyl and N-pyridylcarbazolyl are polycyclic rings linked by carbon-carbon bonds. System type heteroaryl. The "substituted or unsubstituted heteroaryl" in the present application may contain 3 to 30 carbon atoms. In some embodiments, the number of carbon atoms in the substituted or unsubstituted heteroaryl may be 3 to 25. In some embodiments In some embodiments, the number of carbon atoms in the substituted or unsubstituted heteroaryl group can be 5 to 25. In other embodiments, the number of carbon atoms in the substituted or unsubstituted heteroaryl group can be 5 to 20. In other In some embodiments, the number of carbon atoms in the substituted or unsubstituted heteroaryl group can be 5-12.

In the present application, the number of carbon atoms of the substituted or unsubstituted heteroaryl group can be 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 24, 25 or 30.

In the present application, a heteroarylene group refers to a polyvalent group formed by further loss of one or more hydrogen atoms from a heteroaryl group.

In the present application, the substituted heteroaryl group can be one or more than two hydrogen atoms in the heteroaryl group replaced by such as a deuterium atom, a halogen group, a cyano group, an aryl group, a heteroaryl group, a trialkylsilyl group, an alkane group, etc. Substituted by radicals, cycloalkyls, alkoxy groups, etc. It should be understood that the number of carbon atoms in a substituted heteroaryl group refers to the total number of carbon atoms in the heteroaryl group and the substituents on the heteroaryl group.

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

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

In the present application, specific examples of a 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, trifluoromethyl.

In this application,

Both refer to the chemical bonds connecting with other groups, and the various marks on the bonds are only for distinguishing each other.

In this application, a non-positioning linkage refers to a single bond protruding from the ring system

It means that one end of the link can be connected to any position in the ring system that the bond runs 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 group represented by the formula (f) is connected to other positions of the molecule through two unpositioned linkages that run through the bicyclic ring, and the meanings represented include the formula (f -1) to any possible connection shown in formula (f-10).

For another example, as shown in the following formula (X'), the dibenzofuryl group represented by the formula (X') is connected to other positions of the molecule through an unpositioned link extending from the middle of a benzene ring on one side, The meaning represented by it includes any possible connection mode shown in formula (X'-1) to formula (X'-4).

Hereinafter, the meaning of non-positioning connection or non-positioning replacement is the same as here, and will not be repeated hereafter.

In some embodiments of the present application, the Het is a nitrogen-containing heteroarylene group with 3-16 carbon atoms.

Optionally, the Het is selected from the group consisting of the following groups:

in,

Represents a chemical bond; X ₁ and X ₂ are independently selected from O, S or N(Ar), and Ar is selected from phenyl, naphthyl and biphenyl.

In some embodiments of the present application, the Het is selected from the group consisting of the following groups:

in,

Represents a chemical bond.

In some embodiments of the present application, the Het is selected from the group consisting of the following groups:

In some embodiments of the present application, the Het is selected from the group consisting of the following groups:

in,

Indicates the _bond connected to L1,

Indicates any chemical bond; two

Indicates that two bonds connect L ₁ and L ₂ respectively; there is only one in the group

, it means that -L ₂ -Ar ₂ is hydrogen,

Connect to _L1 .

In some embodiments of the present application, the L ₁ , L ₂ and L ₃ are independently selected from a single bond, a substituted or unsubstituted arylene group with 6 to 20 carbon atoms, or an arylene group with 5 to 20 carbon atoms substituted or unsubstituted heteroarylene;

Optionally, the substituents in L ₁ , L ₂ and L ₃ are the same or different, and are independently selected from deuterium, halogen groups, cyano groups, alkyl groups with 1 to 5 carbon atoms, and An aryl group having 6 to 14 carbon atoms or a heteroaryl group having 5 to 12 carbon atoms.

In some embodiments of the present application, said L ₁ , L ₂ and L ₃ are selected from single bond, substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted biphenylene substituted or unsubstituted terphenylene, substituted or unsubstituted fluorenylene, substituted or unsubstituted phenanthrenylene, substituted or unsubstituted anthracenylene, substituted or unsubstituted pyridylene, substituted or Unsubstituted dibenzofurylene, substituted or unsubstituted dibenzothienylene, or substituted or unsubstituted carbazolylidene.

Optionally, the substituents in L ₁ , L ₂ and L ₃ are the same or different, and are independently selected from deuterium, cyano, fluorine, methyl, ethyl, n-propyl, isopropyl, tert-butyl base, phenyl or pyridyl.

In some embodiments of the present application, the L ₁ , L ₂ and L ₃ are each independently selected from a single bond, a substituted or unsubstituted group W ₁ , and the unsubstituted group W ₁ is selected from the following groups Composed of groups:

in,

Represents a chemical bond; the substituted group W has _one or more substituents, each of which is independently selected from deuterium, cyano, fluorine, methyl, ethyl, n-propyl, isopropyl, tert-butyl Base, phenyl or pyridyl; when the number of substituents is greater than 1, each substituent is the same or different.

According to some embodiments of the present application, L ₁ , L ₂ and L ₃ are each independently selected from a single bond or the group consisting of the following groups:

In some embodiments of the present application, the Ar ₁ and Ar ₂ are each independently selected from hydrogen, a substituted or unsubstituted aryl group with 6 to 25 carbon atoms, or a substituted or unsubstituted aryl group with 3 to 25 carbon atoms. Substituted heteroaryl.

Optionally, the substituents in Ar1 and Ar2 are selected from deuterium, halogen groups, cyano groups, alkyl groups with ₁ to ₅ carbon atoms, haloalkyl groups with 1 to 5 carbon atoms, carbon atoms A cycloalkyl group with 5 to 10 carbon atoms, an aryl group with 6 to 12 carbon atoms or a heteroaryl group with 5 to 18 carbon atoms; optionally, in Ar ₁ and Ar ₂ , any two adjacent The substituents form the fluorene ring

or benzene ring

In some embodiments of the present application, the Ar ₁ and Ar ₂ are each independently selected from hydrogen, a substituted or unsubstituted group V, and the unsubstituted group V is selected from the group consisting of the following groups:

in,

Represents a chemical bond; the substituted group V has one or more substituents, each of which is independently selected from deuterium, cyano, fluorine, methyl, ethyl, n-propyl, isopropyl, tert-butyl , cyclopentyl, cyclohexyl, adamantyl, phenyl, biphenyl, naphthyl, pyridyl or trifluoromethyl; when the number of substituents is greater than 1, each substituent is the same or different.

In some embodiments of the present application, Ar ₁ is selected from substituted or unsubstituted group V, Ar ₂ is selected from hydrogen, substituted or unsubstituted group V, wherein, unsubstituted group V is selected from the following groups Composed of groups:

in,

Represents a chemical bond; the substituted group V has one or more substituents, each of which is independently selected from deuterium, cyano, fluorine, methyl, ethyl, n-propyl, isopropyl, tert-butyl , cyclopentyl, cyclohexyl, adamantyl, phenyl, biphenyl, naphthyl, pyridyl or trifluoromethyl; when the number of substituents is greater than 1, each substituent is the same or different.

Optionally, Ar ₁ and Ar ₂ are each independently selected from the group consisting of hydrogen or the following groups:

In some embodiments, each R ₁ , R ₂ , R ₃ and R ₄ are the same or different, each independently selected from hydrogen, deuterium, fluorine, cyano, trimethylsilyl, trideuteromethyl, trifluoro Methyl, cyclopentyl, cyclohexyl, methyl, ethyl, isopropyl, tert-butyl, phenyl or naphthyl.

In some embodiments, in formula 1

selected from the group consisting of:

Optionally, the organic compound is selected from the group consisting of the following groups:

The present application also provides an electronic component, which comprises an anode and a cathode disposed opposite to each other, and at least one functional layer 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 electronic component is an organic electroluminescent device.

Optionally, the functional layer includes an organic electroluminescent layer comprising the organic compound.

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

Optionally, as shown in FIG. 1 , the organic electroluminescent device includes an anode 100, a cathode 200, and at least one functional layer 300 between the anode layer and the cathode layer. Wherein, the functional layer 300 may include a hole injection layer 310, a hole transport layer 320, an organic electroluminescent layer 330, a hole blocking layer 340, an electron transport layer 350, and an electron injection layer 360; wherein the hole transport layer 320 Including a first hole transport layer 321 and a second hole transport layer 322 (relative to the second hole transport layer 322, the first hole transport layer 321 is closer to the anode 100); a hole injection layer 310 , a hole transport layer 320 , an organic electroluminescent layer 330 , a hole blocking layer 340 , an electron transport layer 350 and an electron injection layer 360 may be sequentially formed on the anode 100 . The organic electroluminescent layer 330 may contain the organic compound described in the first aspect of the present application.

Optionally, the anode 100 includes the following anode material, which is preferably a material with a large work function (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 SnO ₂ :Sb; or conducting polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene ](PEDT), polypyrrole and polyaniline, but not limited thereto. It preferably includes a transparent electrode comprising indium tin oxide (ITO) as an anode.

Optionally, the hole transport layer 320 may include one or more hole transport materials, and the hole transport materials may be selected from carbazole polymers, carbazole-linked triarylamine compounds, or other types of compounds. There is no special limitation here. In one embodiment of the present application, the hole transport layer 320 includes a first hole transport layer 321 and a second hole transport layer 322, with respect to the second hole transport layer, the first hole transport layer Layer 321 is closer to the anode 100 . According to a specific implementation manner, the first hole transport layer 321 includes HT-01, and the second hole transport layer 322 includes NPAPF.

Optionally, the organic electroluminescent layer 330 may consist of a single luminescent material, or may include a host material and a guest material. Optionally, the organic electroluminescent layer 330 is composed of a host material and a guest material, the holes and electrons injected into the organic electroluminescent layer 330 can recombine in the organic electroluminescent layer 330 to form excitons, and the excitons transfer energy to The host material, the host material transfers energy to the guest material, thereby enabling the guest material to emit light.

According to one embodiment, the host material of the organic electroluminescent layer 330 includes the organic compound provided in this application. In this application, carbazole derivatives are fused through heteroaryl groups to form large conjugated seven-membered rings, which can fix the configuration of carbazole groups and form a new type of mother nucleus, which can improve the planarity of molecules, making The rotation angle of other aromatic groups attached to the carbazole ring is reduced, which improves the carrier transport capability of the compound and the stability of the compound. At the same time, it can adjust the HOMO/LUMO energy level of the compound and balance the transport efficiency of holes and electrons. When the organic compound of the present application is used as the host material of the organic electroluminescent layer, the luminous efficiency and service life of the organic electroluminescent device can be improved.

The guest material of the organic electroluminescent layer 330 may be a compound with a condensed aryl ring or its derivatives, a compound with a heteroaryl ring or its derivatives, an aromatic amine derivative, or other materials, which are not discussed in this application. special restrictions. In one embodiment of the present application, the guest material of the organic electroluminescent layer 330 is Ir(piq) ₂ (acac).

The electron transport layer 350 can be a single-layer structure or a multilayer structure, which can include one or more electron transport materials, and the electron transport material can be selected from benzimidazole derivatives, oxadiazole derivatives, quinoxaline Derivatives or other electron transport materials, the present application does not make special limitations on this. In one embodiment of the present application, the electron transport layer 350 is composed of ET-01 and LiQ.

Optionally, the cathode 200 includes a cathode material that is a material with a small work function that facilitates injection of electrons into the functional layer. Specific examples of cathode materials include: 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, LiO ₂ /Al, LiF/Ca, LiF/Al and BaF ₂ /Ca, but not limited thereto. A metal electrode comprising silver and magnesium is preferably included as the cathode.

Optionally, a hole injection layer 310 may also be provided between the anode 100 and the hole transport layer 320 to enhance the ability to inject holes into the hole transport layer 320 . The hole injection layer 310 can be selected from benzidine derivatives, starburst arylamine compounds, phthalocyanine derivatives or other materials, which are not particularly limited in this application. In one embodiment of the present application, the hole injection layer 310 is composed of F4-TCNQ and/or other materials.

Optionally, an electron injection layer 360 may also be provided between the cathode 200 and the electron transport layer 350 to enhance the ability to inject electrons into the electron transport layer 350 . The electron injection layer 360 may include inorganic materials such as alkali metal sulfides and alkali metal halides, or may include complexes of alkali metals and organic compounds. In one embodiment of the present application, the electron injection layer 360 is composed of Yb.

The present application also provides an electronic device, which includes the electronic component described in the present application.

As shown in FIG. 2 , the electronic device provided by the present application is an electronic device 400 , and the electronic device 400 includes the above-mentioned electronic components. The electronic device 400 may be a display device, a lighting device, an optical communication device or other types of electronic devices, such as but not limited to a computer screen, a mobile phone screen, a TV, electronic paper, an emergency lighting, an optical module, and the like. Since the electronic device 400 has the above-mentioned organic electroluminescence device, it has the same beneficial effects, and the present application will not repeat them here.

The present application will be described in detail below in conjunction with the embodiments, however, the following description is for explaining the present application, rather than limiting the scope of the present application in any way.

Synthetic example

Those skilled in the art will recognize that the chemical reactions described in this application can be used to suitably prepare many other compounds of this application, and that other methods for preparing the compounds of this application are considered to be within the scope of this application Inside. For example, the synthesis of those non-exemplified compounds according to the application can be successfully accomplished by those skilled in the art by modification methods, such as appropriate protection of interfering groups, by using other known reagents (in addition to those described in the application), Or make some routine modifications to the reaction conditions.

Among them, the compounds of the synthetic methods not mentioned in this application are all raw material products obtained through commercial channels. The analysis and detection of intermediates and compounds in this application use ICP-7700 mass spectrometer.

The compounds in this application were synthesized using the following methods.

Synthesis of intermediate a1-1:

12H-benzofuro[3,2-a]carbazole (32.5g; 126.2mmol), 2-chloro-3-fluoronitrobenzene (22.2g; 126.2mmol), cesium carbonate (25.4g; 126.2mmol) and dry DMSO (300 mL) were added into a nitrogen-protected round-bottom flask, and the temperature was raised to 100° C. for 15 h under stirring. The reaction mixture was lowered to room temperature, the mixed solution was extracted with dichloromethane, the organic phase was collected, and after drying the organic phase with anhydrous magnesium sulfate, the solvent was removed under reduced pressure to obtain the crude product; dichloromethane/n-heptane was used as the elution The crude product was purified by silica gel column chromatography to obtain white solid intermediate a1-1 (30.7 g; yield 59%).

Referring to the synthesis method of intermediate a1-1, using reactant A in table 1 instead of 12H-benzofuro[3,2-a]carbazole, intermediate a1-2 shown in table 1 was synthesized.

Table 1

Synthesis of intermediate a2-1:

Add intermediate a1-1 (35.5g; 86.0mmol), cesium carbonate (84.1g; 258mmol) and DMAC (500mL) into a round bottom flask, stir and raise the temperature to 140°C under nitrogen protection, and divide the water for half an hour; then Cool down to 80°C, add tricyclohexylphosphine fluoroborate (4.8g; 12.9mmol) and palladium acetate (1.5g; 6.9mmol), then stir and heat up to 140°C for 16 hours; cool the reaction mixture to room temperature, wash with water , separate the organic phase, use anhydrous magnesium sulfate to dry the organic phase, and remove the solvent under reduced pressure to obtain the crude product; using dichloromethane/n-heptane as the eluent, the crude product is purified by silica gel column chromatography to obtain intermediate a2-1 (17.2 g; yield 53%).

Referring to the synthesis method of intermediate a2-1, intermediate a1-2 was used instead of intermediate a1-1, and intermediate a2-2 shown in Table 2 was synthesized.

Table 2

Synthesis of Intermediate IM-A-1:

Add intermediate a2-1 (23.6g; 62.7mmol), triphenylphosphine (41.1g; 156.8mmol), o-dichlorobenzene (250mL) into the flask, raise the temperature to 175°C under nitrogen protection, and stir for 36 hours. Cool down to room temperature, wash the reaction mixture with water, and separate the organic phase; after drying the organic phase with anhydrous magnesium sulfate, remove the solvent under reduced pressure to obtain the crude product; use dichloromethane/n-heptane as the eluent, and perform silica gel column chromatography on the crude product Purification gave white solid intermediate IM-A-1 (15.1 g, yield 70%).

Referring to the synthesis method of intermediate IM-A-1, using intermediate a2-2 instead of intermediate a2-1, intermediate IM-A-2 shown in Table 3 was synthesized.

table 3

Synthesis of intermediate IM-B-1:

2,4-dichlorobenzofuro[3,2-D]pyrimidine (21.9g; 91.5mmol), 2-naphthaleneboronic acid (15.0g; 87.2mmol), tetrakistriphenylphosphine palladium (2.0g; 1.7mmol ), potassium carbonate (24.1g; 174.4mmol), tetrabutylammonium bromide (0.6g; 1.7mmol), toluene (160mL), water (40mL), ethanol (40mL) were added into a round bottom flask, under nitrogen protection , heated to 76 ° C and stirred for 12 hours; lowered to room temperature, the reaction liquid was washed with water and separated, the organic phase was dried with anhydrous magnesium sulfate, and the solvent was removed under reduced pressure to obtain the crude product; dichloromethane/n-heptane was used as the eluent The crude product was purified by silica gel column chromatography to obtain a white solid compound, intermediate IM-B-1 (19.0 g; yield 66%).

Referring to the synthesis method of intermediate IM-B-1, the reactant C-X (X is 2 to 9) in Table 4 is used to replace 2,4-dichlorobenzofuro[3,2-D]pyrimidine (C-1), The reactant D-X (X is 2-13) replaces 2-naphthylboronic acid (D-1), and the intermediate IM-B-X (X is 2-16) shown in Table 4 is synthesized.

Table 4

Synthesis of Intermediate IM-B-17:

The intermediate IM-B-12 (15.0g; 50.5mmol), m-chlorophenylboronic acid (8.3g; 53.1mmol), tetrakistriphenylphosphine palladium (1.1g; 1.0mmol), potassium carbonate (13.9g; 101.8mmol ), tetrabutylammonium bromide (0.3g; 1.0mmol), toluene (160mL), water (40mL), and ethanol (40mL) were added into a round bottom flask, and under nitrogen protection, the temperature was raised to 76°C and stirred for 12 hours. After cooling down to room temperature, the reaction mixture was washed with water and separated, and the obtained organic phase was dried with anhydrous magnesium sulfate, and the solvent was removed under reduced pressure to obtain the crude product; using dichloromethane/n-heptane as the eluent, the crude product was subjected to silica gel column chromatography Purified by the method to obtain a white solid compound, the intermediate IM-B-17 (14.3 g; yield 76%).

Referring to the synthesis method of intermediate IM-B-17, use reactant E in Table 5 to replace IM-B-12, and reactant F-X (X is 2 to 3) to replace m-tolylboronic acid (F-1), and synthesize Table 5 The intermediate IM-B-X (X is 18-19) shown in.

table 5

Synthesis of compound C5:

Intermediate IM-A-1 (15g; 43.5mmol), 2-chloro-4-(naphthalene-2-yl)quinazoline (13.3g; 45.7mmol), sodium tert-butoxide (NaOtBu, 8.4g; 87.1 mmol), Pd(t-BuP ₃ ) ₂ (0.4g; 0.8mmol) were put into xylene (200mL), stirred and heated to 140°C, reacted for 5h, cooled to room temperature after the reaction, and the reaction mixture was washed with water and separated , the resulting organic phase was dried using anhydrous magnesium sulfate, and the solvent was removed under reduced pressure to obtain the crude product; using dichloromethane/n-heptane as the eluent, the crude product was purified by silica gel column chromatography to obtain solid compound C5 (16.6g, yield 64%).

Referring to the synthesis method of compound C5, use the reactant IM-A-X (X is 1～2) in Table 6 instead of IM-A-1, and the reactant IM-B-X (X is 1～3, 5～11, 13～19, 21-60) Instead of IM-B-20, the compounds shown in the table below were synthesized.

Table 6

Mass spectrometry was performed on some of the compounds synthesized above, and the results are shown in Table 7.

Table 7

compound	mass spectrometry	compound	mass spectrometry
Compound C5	m/z＝599.18[M+H] +	Compound C201	m/z＝675.21[M+H) +
Compound A3	m/z＝652.21[M+H] +	Compound C131	m/z＝675.21[M+H] +
Compound A8	m/z＝728.24[M+H] +	Compound C202	m/z＝764.24[M+H] +
Compound A14	m/z＝666.19[M+H] +	Compound C203	m/z＝765.22[M+H] +
Compound A15	m/z＝682.16[M+H] +	Compound C151	m/z＝599.18[M+H] +
Compound A9	m/z＝676.21[M+H] +	Compound C154	m/z＝649.20[M+H] +
Compound A23	m/z＝702.22[M+H] +	Compound C171	m/z＝599.18[M+H] +
Compound A26	m/z＝665.20[M+H] +	Compound D37	m/z＝590.15[M+H] +
Compound A99	m/z＝808.30[M+H] +	Compound D12	m/z＝689.19[M+H] +
Compound A52	m/z＝604.21[M+H] +	Compound D50	m/z＝639.17[M+H] +
Compound A53	m/z＝612.16[M+H] +	Compound D56	m/z＝741.22[M+H] +
Compound A100	m/z＝578.17[M+H] +	Compound D130	m/z=681.17[M+H]
Compound A54	m/z＝677.20[M+H] +	Compound D143	m/z＝820.21[M+H] +
Compound A48	m/z＝651.21[M+H] +	Compound D177	m/z＝681.17[M+H] +
Compound A59	m/z＝728.24[M+H] +	Compound D178	m/z＝846.22[M+H] +
Compound A65	m/z＝652.21[M+H] +	Compound D100	m/z＝711.12[M+H] +
Compound A77	m/z＝702.22[M+H] +	Compound E1	m/z＝537.16[M+H] +
Compound A101	m/z＝728.24[M+H] +	Compound E60	m/z＝613.20[M+H] +
Compound C2	m/z＝625.20[M+H] +	Compound B5	m/z＝744.21[M+H] +
Compound C14	m/z＝675.21[M+H] +	Compound B7	m/z＝718.20[M+H] +
Compound C198	m/z＝689.19[M+H] +	Compound F16	m/z＝691.19[M+H] +
Compound C17	m/z＝714.22[M+H] +	Compound F66	m/z＝615.16[M+H] +
Compound C64	m/z＝549.16[M+H] +	Compound F123	m/z＝691.19[M+H] +
Compound C65	m/z＝599.18[M+H] +	Compound F143	m/z＝615.16[M+H] +
Compound C68	m/z＝625.20[M+H] +	Compound F163	m/z＝615.16[M+H] +
Compound C199	m/z＝617.15[M+H] +	Compound G21	m/z＝606.13[M+H] +
Compound C106	m/z＝550.16[M+H] +	Compound G34	m/z＝655.15[M+H] +
Compound C121	m/z＝699.21[M+H] +	Compound G113	m/z＝697.14[M+H] +
Compound C200	m/z＝781.20[M+H] +	Compound H1	m/z＝553.14[M+H] +

Fabrication and Evaluation of Organic Electroluminescent Devices

Example 1

Divide the thickness into

The ITO/Ag/ITO glass substrate was prepared into an experimental substrate with cathode, anode and insulating layer patterns by photolithography process, and then cut into a size of 40mm×40mm×0.7mm.

Substrate cleaning: firstly blow the surface of the substrate with nitrogen to remove pollutants on the surface of the substrate; then use acetone, isopropanol, and deionized water to ultrasonically clean the substrate; then blow with nitrogen to remove the deionized water on the surface of the substrate; after drying, Treated with UV-Ozone for 10 minutes, then placed in a vacuum chamber.

On the experimental substrate (anode), the compound F4-TCNQ and HT-01 were co-evaporated at an evaporation rate ratio of 2%:98%, forming a thickness of

The hole injection layer (HIL), and HT-01 is evaporated on the surface of the hole injection layer to form a thickness of

The first hole transport layer (HTL-1);

Evaporate compound NPAPF on the first hole transport layer to form a thickness of

The second hole transport layer (HTL-2);

On the second hole transport layer, compound RH-P, compound A3 and Ir(piq) ₂ (acac) were co-evaporated with the evaporation rate ratio of 49%: 49%: 2%, forming a thickness of

The red organic electroluminescent layer (red emitting layer, R-EML).

On the organic electroluminescent layer, compound ET-01 and LiQ were co-evaporated with a film thickness ratio of 2:1 to form a thickness of

The electron transport layer (ETL);

Evaporate metal ytterbium (Yb) on the electron transport layer to form a thickness of

The electron injection layer (EIL);

On the electron injection layer, metal magnesium (Mg) and silver (Ag) were co-evaporated at a weight ratio of 1:10 to form a thickness of

the cathode;

Evaporate compound CP-01 on the cathode to form a thickness of

The organic cover layer (CPL) completes the preparation of organic electroluminescent devices.

Embodiment 2 to Embodiment 58

An organic electroluminescent device was fabricated by the same method as in Example 1, except that the compounds shown in Table 6 were used instead of Compound A3 when forming the organic electroluminescent layer.

Comparative example 1

An organic electroluminescent device was prepared in the same manner as in Example 1, except that Compound a shown in Table 8 was used instead of Compound A3 in Example 1 when forming the organic electroluminescent layer.

Comparative example 2

An organic electroluminescent device was prepared in the same manner as in Example 1, except that Compound b shown in Table 8 was used instead of Compound A3 in Example 1 when forming the organic electroluminescent layer.

Comparative example 3

An organic electroluminescent device was prepared in the same manner as in Example 1, except that Compound c shown in Table 8 was used instead of Compound A3 in Example 1 when forming the organic electroluminescent layer.

Comparative example 4

An organic electroluminescent device was prepared in the same manner as in Example 1, except that Compound d shown in Table 8 was used instead of Compound A3 in Example 1 when forming the organic electroluminescent layer.

Wherein, when preparing the organic electroluminescent device, the structural formulas of the materials used in the above comparative examples and examples are shown in Table 8.

Table 8

For the organic electroluminescent device prepared above, the photoelectric performance of the device was analyzed under the condition of 10mA/cm ² , and the lifetime performance of the device was analyzed under the condition of 20mA/cm ² , the results are shown in Table 9.

Table 9

In conjunction with the above table, it can be seen that, under the same situation as other layers of the device, when the organic compound of the present application is used as the host material of the organic electroluminescent layer, compared with Comparative Examples 1 to 4, the luminous efficiency and The lifetimes are all improved; wherein the current efficiency is increased by at least 11.5%, and the device lifetime is increased by at least 23.3%.

Therefore, when the organic compound of the present application is used as the host material of the organic electroluminescent layer to prepare an organic electroluminescent device, the luminous efficiency and service life of the organic electroluminescent device can be effectively improved.

The foregoing variations and modifications fall within the scope of the present disclosure. It shall be understood that the disclosure disclosed and defined in this specification extends to all alternative combinations of two or more of the individual features mentioned or evident in the text and/or drawings. All of these different combinations constitute alternative aspects of the disclosure. The embodiments described in this specification describe the best modes known for carrying out the disclosure and will enable others skilled in the art to utilize the disclosure.

Claims (11)

1. An organic compound, characterized in that the organic compound has a structure shown in formula 1:

   

   Wherein, X is selected from O or S;

   Het is a heteroarylene group with 3 to 20 carbon atoms;

   L ₁ , L ₂ and L ₃ are the same or different, and are independently selected from single bonds, substituted or unsubstituted arylene groups with 6 to 30 carbon atoms, or substituted or unsubstituted arylene groups with 3 to 30 carbon atoms the heteroarylene;

   Ar ₁ and Ar ₂ are the same or different, and are independently selected from hydrogen, a substituted or unsubstituted aryl group with 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group with 3 to 30 carbon atoms;

   The substituents in L ₁ , L ₂ , L ₃ , Ar ₁ and Ar ₂ are the same or different, and are independently selected from deuterium, halogen group, cyano group, heteroaryl group with 3 to 20 carbon atoms, carbon Aryl groups with 6 to 20 atoms, alkyl groups with 1 to 10 carbon atoms, haloalkyl groups with 1 to 10 carbon atoms, cycloalkyl groups with 3 to 10 carbon atoms, and cycloalkyl groups with 2 to 10 carbon atoms 10 heterocycloalkyl groups or alkoxy groups with 1 to 10 carbon atoms;

   Optionally, in Ar ₁ and Ar ₂ , any two adjacent substituents form a ring;

   Each R ₁ , R ₂ , R ₃ and R ₄ are the same or different, and are independently selected from hydrogen, deuterium, halogen group, cyano group, aryl group with 6 to 20 carbon atoms, and 3 to 30 carbon atoms heteroaryl group, trialkylsilyl group with 3 to 12 carbon atoms, alkyl group with 1 to 10 carbon atoms, haloalkyl group with 1 to 10 carbon atoms, ring with 3 to 10 carbon atoms Alkyl, heterocycloalkyl with 2 to 10 carbon atoms or alkoxy with 1 to 10 carbon atoms;

   n ₁ represents the number of substituent R ₁ , n ₁ is selected from 1, 2 or 3, when n ₁ is greater than 1, any two R ₁ are the same or different;

   n ₂ represents the number of substituent R ₂ , n ₂ is selected from 1 or 2, when n ₂ is greater than 1, any two R ₂ are the same or different;

   n ₃ represents the number of substituent R ₃ , n ₃ is selected from 1 or 2, when n ₃ is greater than 1, any two R ₃ are the same or different;

   n ₄ represents the number of substituent R ₄ , n ₄ is selected from 1, 2, 3 or 4, when n ₄ is greater than 1, any two R ₄ are the same or different.
2. The organic compound according to claim 1, wherein the Het is a nitrogen-containing heteroarylene group with 3 to 16 carbon atoms.
3. The organic compound according to claim 1, wherein the Het is selected from the group consisting of the following groups:

   

   in,

   

   Represents a chemical bond.
4. The organic compound according to claim 1, wherein said L ₁ , L ₂ and L ₃ are each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, or a carbon A substituted or unsubstituted heteroarylene group with 5 to 20 atoms;

   Optionally, the substituents in L ₁ , L ₂ and L ₃ are the same or different, and are independently selected from deuterium, halogen groups, cyano groups, alkyl groups with 1 to 5 carbon atoms, and An aryl group having 6 to 14 carbon atoms or a heteroaryl group having 5 to 12 carbon atoms.
5. The organic compound according to claim 1, wherein said L ₁ , L ₂ and L ₃ are independently selected from single bond, substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene, Substituted or unsubstituted biphenylene, substituted or unsubstituted terphenylene, substituted or unsubstituted fluorenylene, substituted or unsubstituted phenanthrenylene, substituted or unsubstituted anthracenylene, substituted or unsubstituted Substituted pyridylene, substituted or unsubstituted dibenzofurylene, substituted or unsubstituted dibenzothienylene, or substituted or unsubstituted carbazolylidene;

   Optionally, the substituents in L ₁ , L ₂ and L ₃ are the same or different, and are independently selected from deuterium, cyano, fluorine, methyl, ethyl, n-propyl, isopropyl, tert-butyl base, phenyl or pyridyl.
6. The organic compound according to claim 1, wherein said Ar ₁ and Ar ₂ are each independently selected from hydrogen, a substituted or unsubstituted aryl group with 6 to 25 carbon atoms, or a aryl group with 3 to 25 carbon atoms. 25 substituted or unsubstituted heteroaryl;

   Optionally, the substituents in Ar1 and Ar2 are selected from deuterium, halogen groups, cyano groups, alkyl groups with ₁ to ₅ carbon atoms, haloalkyl groups with 1 to 5 carbon atoms, carbon atoms A cycloalkyl group with 5 to 10 carbon atoms, an aryl group with 6 to 12 carbon atoms or a heteroaryl group with 5 to 18 carbon atoms; optionally, in Ar ₁ and Ar ₂ , any two adjacent The substituents form a fluorene ring or a benzene ring.
7. The organic compound according to claim ₁ , wherein said Ar and Ar are each independently selected from _hydrogen , substituted or unsubstituted group V, and the unsubstituted group V is selected from the group consisting of Group:

   

   in,

   

   Represents a chemical bond; the substituted group V has one or more substituents, each of which is independently selected from deuterium, cyano, fluorine, methyl, ethyl, n-propyl, isopropyl, tert-butyl , cyclopentyl, cyclohexyl, adamantyl, phenyl, biphenyl, naphthyl, pyridyl or trifluoromethyl; when the number of substituents in the group V is greater than 1, each substituent is the same or different.
8. The organic compound according to claim 1, wherein the organic compound is selected from the group consisting of the following compounds:

   

   

   

   

   

   

   

   

   

   

   

   

   

   

   

   

   

   

   

   

   

   

   

   

   

   
9. The electronic component is characterized in that it includes an anode and a cathode arranged oppositely, and a functional layer arranged between the anode and the cathode;

   The functional layer comprises the organic compound according to any one of claims 1-8;

   Preferably, the functional layer comprises an organic electroluminescent layer comprising the organic compound.
10. The electronic component according to claim 9, wherein the electronic component is an organic electroluminescent device;

    Preferably, the organic electroluminescent device is a red organic electroluminescent device.
11. An electronic device, comprising the electronic component according to claim 9 or 10.

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