WO2024082645A1

WO2024082645A1 - Organic compound, organic electroluminescent device, and electronic device

Info

Publication number: WO2024082645A1
Application number: PCT/CN2023/097886
Authority: WO
Inventors: 马天天; 呼琳琳; 刘云
Original assignee: 陕西莱特光电材料股份有限公司
Priority date: 2022-10-17
Filing date: 2023-06-01
Publication date: 2024-04-25
Also published as: CN117946132A

Abstract

The present application relates to the technical field of organic electroluminescence, and relates to an organic compound, an organic electroluminescent device using same, and an electronic device. The organic compound has a structure as represented by formula (1). The organic compound is used in the organic electroluminescent device, so that the performance of the organic electroluminescent device can be remarkably improved.

Description

Organic compound, organic electroluminescent device and electronic device

CROSS-REFERENCE TO RELATED APPLICATIONS

This application claims priority to Chinese patent application No. 202211266690.6 filed on October 17, 2022. The entire text of the above Chinese patent application is hereby cited as part of this application.

Technical Field

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

Background technique

With the development of electronic technology and the progress of materials science, the application scope of electronic components for realizing electroluminescence or photoelectric conversion is becoming more and more extensive. Such electronic components generally include a cathode and an anode arranged relatively to each other, 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 light-emitting layer as an energy conversion layer, an electron transport layer and a cathode stacked in sequence. When a voltage is applied to the positive and negative electrodes, the two electrodes generate an electric field. Under the action of the electric field, the electrons on the cathode side move toward the organic light-emitting layer, and the holes on the anode side also move toward the organic light-emitting layer. The electrons and holes combine in the organic light-emitting layer to form excitons, and the excitons are in an excited state and release energy outward, thereby causing the organic light-emitting layer to emit light outward.

The prior art discloses host materials that can be used to prepare organic light-emitting layers in organic electroluminescent devices. However, it is still necessary to continue to develop new materials to further improve the performance of electronic components.

Summary of the invention

To solve the above problems, the purpose of the present application is to provide an organic compound and an organic electroluminescent device and an electronic device containing the organic compound, wherein the organic compound can improve the performance of the organic electroluminescent device and the electronic device, such as reducing the driving voltage of the device and improving the efficiency and life of the device.

In a first aspect of the present application, an organic compound is provided, wherein the organic compound has a structure as shown in Formula 1:

Wherein, _R1 is selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms or a substituted or unsubstituted heteroaryl group having 12 to 30 carbon atoms;

Ar is selected from a substituted or unsubstituted arylene group having 6 to 30 carbon atoms or a substituted or unsubstituted heteroarylene group having 12 to 30 carbon atoms;

R ₄ is selected from hydrogen or a group represented by formula 2;

_R2 and _R3 are the same or different and are independently selected from hydrogen, deuterium, cyano, halogen, aryl having 6 to 30 carbon atoms, A heteroaryl group having 3 to 30 carbon atoms or a group represented by formula 2;

And only one of R ₄ , R ₂ and R ₃ is a group represented by Formula 2;

L, L ₁ , L ₂ and L ₃ are the same or different and are independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms or a substituted or unsubstituted heteroarylene group having 12 to 30 carbon atoms;

Ar ₁ and Ar ₂ are the same or different and are independently selected from a substituted or unsubstituted aryl group having 6 to 40 carbon atoms or a substituted or unsubstituted heteroaryl group having 12 to 40 carbon atoms;

The substituents in R ₁ , L, L ₁ , L ₂ , Ar, Ar ₁ and Ar ₂ are the same or different and are independently selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, a heteroaryl group having 12 to 20 carbon atoms, a deuterated aryl group having 6 to 20 carbon atoms, a halogenated aryl group having 6 to 20 carbon atoms, a trialkylsilyl group having 3 to 12 carbon atoms, a triarylsilyl group having 18 to 24 carbon atoms, a halogenated alkyl group having 1 to 10 carbon atoms, a deuterated alkyl group having 1 to 10 carbon atoms or an aryl group having 6 to 20 carbon atoms;

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

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

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

The core group of the organic compound of the present application is formed by condensing benzocarbazole and oxazole in a specific manner, and the core group has a planar quasi-ring structure, which can have a strong carrier transport capability and a high energy transfer capability while maintaining a high first triplet energy level value; at the same time, the group has a good electron dispersion capability. The core group is combined with a triarylamine, and the organic compound formed can effectively improve the electron tolerance of the molecule when it is used as a hole transport material of the light-emitting layer. In particular, when the organic compound of the present application is used as a main material of the light-emitting layer in an organic electroluminescent device, the device performance can be significantly improved.

Other features and advantages of the present application will be described in detail in the subsequent specific implementation section.

BRIEF DESCRIPTION OF THE DRAWINGS

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

FIG. 1 is a schematic diagram of the structure of an organic electroluminescent device of the present application.

FIG. 2 is a schematic diagram of the structure of an electronic device of the present application.

Reference numerals

100. Anode 200. Cathode 300. Functional layer 310. Hole injection layer

320, first hole transport layer 330, second hole transport layer 340, organic light emitting layer 350, electron transport layer

360. Electron injection layer 400. Electronic device

Detailed ways

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

R ₄ is selected from hydrogen or a group represented by formula 2;

_R2 and _R3 are the same or different and are independently selected from hydrogen, deuterium, cyano, halogen, aryl having 6 to 30 carbon atoms, heteroaryl having 3 to 30 carbon atoms or a group represented by Formula 2;

And only one of R ₄ , R ₂ and R ₃ is a group represented by Formula 2;

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

In the present application, the terms "optionally" and "optionally" mean that the event or circumstance described subsequently may occur but need not occur, and the description includes occasions where the event or circumstance occurs or does not occur. For example, "optionally, any two adjacent substituents form a ring" means that the two substituents may form a ring but do not have to form a ring, including: the situation where the two adjacent substituents form a ring and the situation where the two adjacent substituents do not form a ring.

In the present application, in the phrase "any two adjacent substituents form a ring", "any two adjacent" may include two substituents on the same atom, or one substituent on each of two adjacent atoms; when two substituents are on the same atom, the two substituents may form a saturated or unsaturated ring with the atom to which they are connected; when two adjacent atoms each have one substituent, the two substituents may be fused into a ring. For example, when there are two or more substituents in Ar ₁ , when any adjacent substituents form a ring, a saturated or unsaturated cyclic group is formed, such as a benzene ring, a naphthalene ring, a phenanthrene ring, an anthracene ring, a fluorene ring, a cyclopentane, a cyclohexane, adamantane, and the like.

In the present application, the fluorenyl group may be substituted by 1 or 2 substituents, wherein, when the fluorenyl group is substituted, it may be: etc., but not limited thereto.

In this application, the descriptions "each... is independently" and "... are independently" and "... are independently selected from" are interchangeable and should be understood in a broad sense. They can mean that in different groups, the specific options expressed by the same symbols do not affect each other, or in the same group, the specific options expressed by the same symbols do not affect each other. For example, " Wherein, each q is independently 0, 1, 2 or 3, and each R" is independently selected from hydrogen, deuterium, fluorine, and chlorine, which means: Formula Q-1 indicates that there are q substituents R" on the benzene ring, and each R" can be the same or different, and the options of each R" do not affect each other; Formula Q-2 indicates that there are q substituents R" on each benzene ring of biphenyl, and the number q of R" substituents on the two benzene rings can be the same or different, and each R" can be the same or different, and the options of each R" do not affect each other.

In the present application, the term "substituted or unsubstituted" means that the functional group recorded after the term may or may not have a substituent (hereinafter, for the convenience of description, the substituents are collectively referred to as Rc). For example, "substituted or unsubstituted aryl" refers to an aryl having a substituent Rc or an unsubstituted aryl. The above-mentioned substituent, i.e., Rc, can be, for example, deuterium, a halogen group, a cyano group, an alkyl group, a cycloalkyl group, a heteroaryl group, a deuterated aryl group, a halogenated aryl group, a trialkylsilyl group, a triarylsilyl group, a halogenated alkyl group, a deuterated alkyl group, etc.

In the present application, the number of carbon atoms of a substituted or unsubstituted functional group refers to the total number of carbon atoms. For example, if _L1 is a substituted arylene group having 12 carbon atoms, the total number of carbon atoms of the arylene group and the substituents thereon is 12.

In the present 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 (such as phenyl) or a polycyclic aryl group. In other words, the aryl group can be a monocyclic aryl group, a condensed ring aryl group, two or more monocyclic aryl groups connected by carbon-carbon bond conjugation, a monocyclic aryl group and a condensed ring aryl group connected by carbon-carbon bond conjugation, and two or more condensed ring aryl groups connected by carbon-carbon bond conjugation. That is, unless otherwise specified, two or more aromatic groups connected by carbon-carbon bond conjugation can also be regarded as aryl groups of the present application. Among them, condensed ring aryl groups can include, for example, bicyclic condensed aryl groups (such as naphthyl), tricyclic condensed aryl groups (such as phenanthrenyl, fluorenyl, anthracenyl), etc. The aryl group does not contain heteroatoms such as B, N, O, S, P, Se and Si. Examples of aryl groups can include, but are not limited to, phenyl, naphthyl, fluorenyl, anthracenyl, phenanthrenyl, biphenyl, terphenyl, benzo[9,10]phenanthrenyl, pyrenyl, benzofluoranthenyl, Base, spirobifluorenyl, etc.

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

In the present application, terphenyl includes

In the present application, the substituted aryl group may be one or more hydrogen atoms in the aryl group replaced by groups such as deuterium atoms, halogen groups, cyano groups, aryl groups, heteroaryl groups, alkyl groups, cycloalkyl groups, etc. It should be understood that the number of carbon atoms in the 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 with 18 carbon atoms means that the total number of carbon atoms in the aryl group and the substituents is 18.

In the present application, heteroaryl refers to a monovalent aromatic ring or a derivative thereof containing 1, 2, 3, 4, 5, 6 or 7 heteroatoms in the ring, and the heteroatoms may be at least one of B, O, N, P, Si, Se and S. The heteroaryl may be a monocyclic heteroaryl or a polycyclic heteroaryl. In other words, the heteroaryl may be a single aromatic ring system or a plurality of aromatic ring systems conjugated by carbon-carbon bonds, and any aromatic ring system is an aromatic monocyclic ring or an aromatic condensed ring. For example, the heteroaryl may include thienyl, furanyl, pyrrolyl, imidazolyl, thiazolyl, oxazolyl, oxadiazolyl, triazolyl, pyridyl, bipyridyl, pyrimidyl, triazine, azetyl, thiazolyl, oxadiazolyl, triazolyl, pyridyl, bipyridyl, pyrimidyl, triazine, thiazolyl, thiazolyl, oxazolyl, oxadiazolyl, triazolyl, pyridyl, bipyridyl, pyrimidyl, triazine, thiazolyl ... The pyridyl, pyridazinyl, pyrazinyl, quinolyl, quinazolyl, quinoxalinyl, phenoxazinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, isoquinolyl, indolyl, carbazolyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothienyl, dibenzothienyl, thienothiphenyl, benzofuranyl, phenanthrolinyl, isoxazolyl, thiadiazolyl, phenothiazinyl, silyfluorenyl, dibenzofuranyl, and N-phenylcarbazolyl, N-pyridylcarbazolyl, N-methylcarbazolyl, etc., but not limited thereto. Among them, thienyl, furanyl, phenanthrolinyl, etc. are heteroaryl groups of a single aromatic ring system type, and N-phenylcarbazolyl and N-pyridylcarbazolyl are heteroaryl groups of a polycyclic system type connected by carbon-carbon bonds. In the present application, the heteroarylene group refers to a divalent group formed by further losing a hydrogen atom from a heteroaryl group.

In the present application, the substituted heteroaryl group may be a heteroaryl group in which one or more hydrogen atoms are replaced by groups such as deuterium atoms, halogen groups, cyano groups, aryl groups, heteroaryl groups, alkyl groups, cycloalkyl groups, etc. It should be 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 substituents on the heteroaryl group.

In the present application, the number of carbon atoms of the substituted or unsubstituted aryl group can be 6 to 25, for example, the number of carbon atoms can be 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24 or 25.

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

In the present application, the number of carbon atoms of the substituted or unsubstituted heteroaryl group may be 12 to 24, for example, the number of carbon atoms may be 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23 or 24.

In the present application, specific examples of heteroaryl groups as substituents include, but are not limited to, triazine, pyridyl, pyrimidinyl, carbazolyl, dibenzofuranyl, dibenzothiophenyl, quinolyl, quinazolinyl, quinoxalinyl, isoquinolyl, carbazolyl, and N-phenylcarbazolyl.

In this application, the non-positioned connecting bond refers to the single bond extending from the ring system. It means that one end of the connecting bond can be connected to any position in the ring system that the bond passes through, and the other end is connected to the rest of the compound molecule.

For example, as shown in the following formula (f), the naphthyl group represented by formula (f) is connected to other positions of the molecule through two non-positional connecting bonds that penetrate the bicyclic ring, and its meaning includes any possible connection method shown in formulas (f-1) to (f-10).

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

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

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

In the present application, specific examples of triarylsilyl include, but are not limited to, triphenylsilyl.

In the present application, the carbon number of the cycloalkyl group having 3 to 20 carbon atoms may be, for example, 3, 4, 5, 6, 7, 8, 10, etc. Specific examples of the cycloalkyl group include, but are not limited to, cyclopentyl, cyclohexyl, and adamantyl.

In some embodiments of the present application, the substituents in R ₁ , L, L ₁ , L ₂ , Ar, Ar ₁ and Ar ₂ are the same or different and are independently selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, a heteroaryl group having 12 to 20 carbon atoms, a deuterated aryl group having 6 to 20 carbon atoms, a halogenated aryl group having 6 to 20 carbon atoms, a trialkylsilyl group having 3 to 12 carbon atoms, a triarylsilyl group having 18 to 24 carbon atoms, a halogenated alkyl group having 1 to 10 carbon atoms or a deuterated alkyl group having 1 to 10 carbon atoms.

In the present application, the organic compound is selected from the compounds shown in Formula 1-1, Formula 1-2 or Formula 1-3:

Ar in the above formula 1-2 and formula 1-3 represents that when R ₄ is hydrogen

In some embodiments of the present application, L, L ₁ , L ₂ and L ₃ are the same or different and are independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 15 carbon atoms or a substituted or unsubstituted heteroarylene group having 12 to 20 carbon atoms.

Optionally, the substituents in L, L ₁ , L ₂ and L ₃ are the same or different, and are independently selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 5 carbon atoms or a phenyl group.

In other embodiments of the present application, L, L ₁ , L ₂ and L ₃ are the same or different, and are independently selected from a single bond, a substituted or unsubstituted phenylene, a substituted or unsubstituted biphenylene, a substituted or unsubstituted naphthylene, a substituted or unsubstituted fluorenylene, a substituted or unsubstituted phenanthrenylene, a substituted or unsubstituted carbazolylene, a substituted or unsubstituted dibenzofuranylene or a substituted or unsubstituted dibenzothiophenylene.

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

Further optionally, L and _L3 are the same or different and are independently selected from a single bond, a substituted or unsubstituted phenylene, a naphthylene, biphenylene, dimethylfluorenylene, dibenzothiophenylene, dibenzofuranylene or carbazolylene.

Preferably, L ₃ is selected from a single bond, a substituted or unsubstituted phenylene group, a naphthylene group, a biphenylene group, a dimethylfluorenyl group, a dibenzothienyl group or a dibenzofuranyl group.

Further optionally, _L1 and _L2 are the same or different, and are independently selected from a single bond, a substituted or unsubstituted phenylene, a substituted or unsubstituted biphenylene, a substituted or unsubstituted naphthylene, a substituted or unsubstituted fluorenylene, a substituted or unsubstituted phenanthrenylene, a substituted or unsubstituted carbazolylene, a substituted or unsubstituted dibenzofuranylene or a substituted or unsubstituted dibenzothiophenylene.

In some embodiments of the present application, L, L ₁ , L ₂ and L ₃ are the same or different, and are independently selected from a single bond, a substituted or unsubstituted group V, wherein the unsubstituted group V is selected from the group consisting of the following groups:

in, represents a chemical bond; the substituted group V contains one or more substituents, and the substituents are selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl or phenyl; and when the substituted group V contains multiple substituents, the substituents are the same or different.

Specifically, L is selected from the group consisting of a single bond or the following groups:

Specifically, _L1 and _L2 are the same or different and are independently selected from a single bond or the following groups:

Specifically, _L3 is selected from a single bond or the group consisting of:

In some embodiments of the present application, Ar ₁ and Ar ₂ are the same or different, and are independently selected from a substituted or unsubstituted aryl group having 6 to 25 carbon atoms or a substituted or unsubstituted heteroaryl group having 12 to 24 carbon atoms.

Optionally, the substituents in Ar ₁ and Ar ₂ are the same or different and are independently selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 5 carbon atoms or a phenyl group;

Optionally, in _Ar1 and _Ar2 , any two adjacent substituents form a fluorene ring

In some embodiments of the present application, _Ar1 and _Ar2 are the same or different, and are independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted triphenylene, substituted or unsubstituted fluorenyl, substituted or unsubstituted spirobifluorenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl or substituted or unsubstituted carbazolyl.

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

In some embodiments of the present application, Ar ₁ and Ar ₂ are the same or different, and are independently selected from substituted or unsubstituted groups W, wherein the unsubstituted group W is selected from the following groups:

The substituted group W has one or more substituents, each of which is independently selected from the group consisting of deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl and phenyl. When the number of substituents on the group W is greater than 1, each of which is The bases are the same or different.

Optionally, Ar ₁ and Ar ₂ are the same or different and are independently selected from the following groups:

Specifically, Ar ₁ and Ar ₂ are the same or different and are independently selected from the group consisting of the following groups:

In some embodiments of the present application, The same or different, each independently selected from the group consisting of the following groups:

specifically, The same or different, each independently selected from the group consisting of the following groups:

In some embodiments of the present application, Selected from the group consisting of:

In some embodiments of the present application, R ₁ is selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothienyl or substituted or unsubstituted carbazolyl.

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

In other embodiments of the present application, R ₁ is selected from a substituted or unsubstituted group G, wherein the unsubstituted group G is selected from the group consisting of the following groups:

The substituted group G has one or more substituents, and the substituents are independently selected from the group consisting of deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl and phenyl, and when the number of substituents on the group G is greater than 1, the substituents are the same or different.

Specifically, _R1 is selected from the group consisting of:

In some embodiments of the present application, Ar is selected from substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted biphenylene, substituted or unsubstituted fluorenylene, substituted or unsubstituted carbazolylene, substituted or unsubstituted dibenzothienylene or substituted or unsubstituted dibenzofuranylene;

The substituents in Ar are the same or different and are independently selected from hydrogen, deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl or phenyl;

R ₄ is selected from hydrogen or a group represented by formula 2;

_R2 and _R3 are the same or different and are independently selected from hydrogen or a group represented by Formula 2;

And only one of R ₄ , R ₂ and R ₃ is a group represented by Formula 2.

In some embodiments of the present application, R ₄ is a group represented by Formula 2, and Ar is selected from substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene, or substituted or unsubstituted biphenylene;

Optionally, the substituents in Ar are the same or different and are independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl or phenyl.

In some embodiments of the present application, _R4 is hydrogen, Ar is selected from substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted biphenylene, substituted or unsubstituted fluorenylene, substituted or unsubstituted carbazolylene, substituted or unsubstituted dibenzothienylene or substituted or unsubstituted dibenzofuranylene;

In some embodiments of the present application, _R4 is hydrogen, Selected from the group consisting of:

In some embodiments of the present application, R ₄ is selected from hydrogen or a group shown in Formula 2.

In some embodiments of the present application, _R4 and _R2 are hydrogen, and _R3 is a group shown in Formula 2.

In some embodiments of the present application, R ₄ is a group represented by Formula 2, and R ₂ and R ₃ are both hydrogen.

In some embodiments of the present application, _R4 and _R3 are hydrogen, and _R2 is a group shown in Formula 2.

In some embodiments of the present application, _R2 and _R3 are the same or different, and are independently selected from hydrogen or a group shown in Formula 2.

Ar represents when R ₄ is hydrogen

In some specific embodiments of the present application, L ₃ is selected from a single bond, a phenylene group, a naphthylene group or a biphenylene group;

Ar is selected from substituted or unsubstituted phenylene, substituted or unsubstituted biphenylene, substituted or unsubstituted terphenylene or substituted or unsubstituted carbazolylene;

Optionally, the substituents in Ar are the same or different and are independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl or phenyl;

_R3 is a group represented by formula 2, _R2 is hydrogen, and _R4 is hydrogen.

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

In a second aspect of the present application, the present application provides an organic electroluminescent device, comprising an anode and a cathode arranged opposite to each other, and A functional layer is provided between the anode and the cathode; the functional layer comprises the organic compound of the present application.

In some embodiments of the present application, the organic electroluminescent device is a red organic electroluminescent device. As shown in FIG1 , the organic electroluminescent device may include an anode 100, a first hole transport layer 320, a second hole transport layer 330, an organic light emitting layer 340, an electron transport layer 350, an electron injection layer 360 and a cathode 200 stacked in sequence.

Optionally, the anode 100 includes the following anode material, which is optionally a material with a large work function that facilitates hole injection into the functional layer. Specific examples of anode materials include: metals such as nickel, platinum, vanadium, chromium, copper, zinc and gold or their alloys; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO) and indium zinc oxide (IZO); combined metals and oxides such as ZnO:Al or SnO ₂ :Sb; or conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDT), polypyrrole and polyaniline, but are not limited thereto. It is preferred to include indium tin oxide (ITO) as a transparent electrode of the anode.

Optionally, the first hole transport layer 320 and the second hole transport layer 330 include one or more hole transport materials, and the hole transport material can be selected from carbazole polymers, carbazole-linked triarylamine compounds or other types of compounds. Those skilled in the art can refer to the prior art for selection, and this application does not make any special restrictions on this. In some embodiments of the present application, the first hole transport layer 320 is HT-22 and the second hole transport layer 330 is HT-23.

Optionally, a hole injection layer 310 may be provided between the anode 100 and the first 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, and the present application does not impose any particular limitation on this. The material of the hole injection layer 310 may be selected from the following compounds or any combination thereof;

In some embodiments of the present application, the hole injection layer 310 is composed of PD and HT-22.

Optionally, the organic light-emitting layer 340 may be composed of a single light-emitting layer material, or may include a main material and a doping material. Optionally, the organic light-emitting layer 340 is composed of a main material and a doping material, and holes injected into the organic light-emitting layer 340 and electrons injected into the organic light-emitting layer 340 may be recombined in the organic light-emitting layer 340 to form excitons, and the excitons transfer energy to the main material, and the main material transfers energy to the doping material, thereby enabling the doping material to emit light.

The main material of the organic light-emitting layer 340 may be a metal chelate compound, a bisphenylethylene derivative, an aromatic amine derivative, a dibenzofuran derivative or other types of materials, and the present application does not impose any special limitation thereto.

In one embodiment of the present application, the organic light-emitting layer 340 includes the organic compound of the present application.

Optionally, the organic compound of the present application is used as a host material (hole transport type host material) of the organic light emitting layer 340 .

In some embodiments of the present application, the electron transport type host material of the organic light emitting layer 340 is (RH—N).

The guest material of the organic light-emitting layer 340 can be a compound having a condensed aromatic ring or a derivative thereof, a compound having a heteroaromatic ring or a derivative thereof, an aromatic amine derivative or other materials, and the present application does not impose any special restrictions on this. The guest material is also called a doping material or a dopant. Specific examples of red phosphorescent dopants for red organic electroluminescent devices include, but are not limited to,

In a more specific embodiment, the host material of the organic light emitting layer 340 is the organic compound of the present application and RH—N, and the guest material is RD.

The electron transport layer 350 may be a single-layer structure or a multi-layer structure, and may include one or more electron transport materials, which may be selected from but not limited to ET-1, LiQ, benzimidazole derivatives, oxadiazole derivatives, quinoxaline derivatives or other electron transport materials, and the present application does not make any special restrictions. The materials of the electron transport layer 350 include but are not limited to the following compounds:

In some specific embodiments of the present application, the electron transport layer 350 is composed of ET-1 and LiQ.

In the present application, the cathode 200 may include a cathode material, which is a material with a small work function that facilitates electron injection into the functional layer. Specific examples of cathode materials include, but are not limited to, metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead or alloys thereof; or multilayer materials such as LiF/Al, Liq/Al, LiO ₂ /Al, LiF/Ca, LiF/Al and BaF ₂ /Ca. Optionally, a metal electrode containing magnesium and silver is included as the cathode.

In some embodiments of the present application, the electron injection layer 360 may include ytterbium (Yb).

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

According to one embodiment, as shown in FIG2 , the provided electronic device is an electronic device 400, which includes the above-mentioned organic electroluminescent device. The electronic device 400 may be, for example, a display device, a lighting device, an optical communication device or other types of electronic devices. For example, it may include but is not limited to computer screens, mobile phone screens, televisions, electronic paper, emergency lighting, optical modules, etc.

The synthesis method of the organic compound of the present application is specifically described below in conjunction with synthesis examples, but the present application is not limited thereto.

The compounds whose synthesis methods are not mentioned in this application are all raw materials obtained through commercial channels.

The present application does not particularly limit the synthesis method of the organic materials provided. Those skilled in the art can determine a suitable synthesis method based on the organic materials of the present application in combination with the preparation methods provided in the preparation examples. Those skilled in the art can obtain all the organic materials provided in the present application based on these exemplary preparation methods. All specific preparation methods for preparing the organic materials will not be described in detail here, and those skilled in the art should not be understood as limiting the present application.

Preparation of compounds

Synthesis of intermediate IM-a-1

Under nitrogen protection, 2-bromo-7-chlorobenzo[d]oxazole (11.63 g, 50 mmol), 2-naphthaleneboronic acid (9.46 g, 55 mmol), tetrakis(triphenylphosphine)palladium (Pd(PPh ₃ ) ₄ , 0.58 g, 0.5 mmol), anhydrous sodium carbonate (10.60 g, 100 mmol), toluene (140 mL), tetrahydrofuran (35 mL) and deionized water (35 mL) were added to a 500 mL three-necked flask in sequence, stirring and heating were started, and the temperature was raised to reflux for reaction for 16 h. After the system was cooled to room temperature, it was extracted with dichloromethane (100 mL×3 times), the organic phases were combined and dried over anhydrous magnesium sulfate, filtered and then distilled under reduced pressure to remove the solvent to obtain a crude product. The crude product was purified by silica gel column chromatography using n-heptane as the mobile phase to obtain a white solid (12.45 g, yield 89%).

Referring to the synthesis method of intermediate IM-a-1, the intermediate shown in Table 1 was synthesized by substituting raw material 1 in Table 1 for 2-bromo-7-chlorobenzo[d]oxazole and raw material 2 for 2-naphthaleneboric acid:

Table 1: Preparation of intermediate IM-a-2

Synthesis of intermediate IM-b-1

Under nitrogen protection, intermediate IM-a-1 (12.31 g, 44 mmol), biboric acid pinacol ester (12.28 g, 48.4 mmol), potassium acetate (KOAc, 9.50 g, 96.8 mmol) and 1,4-dioxane (120 mL) were added to a 500 mL three-necked flask in sequence, and stirring and addition were started. Heat, when the system is heated to 40°C, quickly add tri(dibenzylideneacetone)dipalladium (Pd ₂ (dba) ₃ , 0.40g, 0.44mmol) and (2-dicyclohexylphosphine-2',4',6'triisopropylbiphenyl) (XPhos, 0.42g, 0.88mmol), continue to heat to reflux, and stir to react overnight. After the system is cooled to room temperature, add 200mL of water to the system, stir well for 30min, filter under reduced pressure, wash the filter cake with deionized water until neutral, and then rinse with 100mL of anhydrous ethanol to obtain a gray solid crude product; the crude product is slurried once with n-heptane, and then dissolved with 200mL of toluene and passed through a silica gel column to remove the catalyst, and concentrated to obtain a white solid intermediate IM-b-1 (13.56g, yield 83%).

Referring to the synthesis method of intermediate IM-b-1, the intermediate shown in Table 2 was synthesized by replacing intermediate IM-a-1 with raw material 3 in Table 2:

Table 2: Synthesis of intermediate IM-bX

Synthesis of intermediate IM-c-1

Under nitrogen protection, 1-bromo-7-chloronaphthalene (24.15g, 100mmol) and sulfuric acid (50mL) were added to a 200mL three-necked flask in sequence, and stirring was started. After the system was stirred evenly, nitric acid (5.04g, 80mmol) was added to a constant pressure dropping funnel and dripped into the reaction system, keeping the system temperature not higher than 55°C. After the dripping was completed, the reaction was stirred at room temperature overnight. The reaction solution changed from a transparent liquid to a red liquid, and finally a large number of solid particles were slowly precipitated. After the reaction was completed, the reaction solution was slowly poured into 200mL ice water, fully stirred for 30min, filtered under reduced pressure, the filter cake was washed with deionized water until neutral, and then rinsed with 100mL anhydrous ethanol to obtain a yellow solid; dried in a blast oven to obtain a yellow solid intermediate IM-c-1 (15.76g, yield 55%).

The same method as intermediate IM-c-1 was used to replace 1-bromo-7-chloronaphthalene with the raw material 4 in Table 3 to synthesize the intermediate shown in Table 3:

Table 3: Synthesis of intermediate IM-cX

Synthesis of intermediate IM-d-1

Under nitrogen protection, intermediate IM-c-1 (12.61 g, 44 mmol), intermediate IM-b-1 (15.55 g, 48.4 mmol), potassium acetate (KOAc, 9.50 g, 96.8 mmol) and 1,4-dioxane (120 mL) were added in sequence to a 500 mL three-necked flask, stirring and heating were started, and when the system was heated to 40°C, tris(dibenzylideneacetone)dipalladium ( _Pd2 (dba) ₃ , 0.40 g, 0.44 mmol) and (2-dicyclohexylphosphine-2',4',6'triisopropylbiphenyl) (XPhos, 0.42 g, 0.88 mmol) were quickly added, and the temperature was continued to rise to reflux, and the reaction was stirred overnight. After the system is cooled to room temperature, 200 mL of water is added to the system, stirred thoroughly for 30 min, and filtered under reduced pressure. The filter cake is washed with deionized water until neutral, and then rinsed with 100 mL of anhydrous ethanol to obtain a gray solid; the crude product is slurried once with n-heptane, dissolved with 200 mL of toluene, and then passed through a silica gel column to remove the catalyst and concentrate to obtain a white solid intermediate IM-d-1 (14.11 g, yield 80%).

Referring to the synthesis method of intermediate IM-d-1, the intermediate IM-c-1 was replaced by raw material 5 in Table 4, and the intermediate IM-b-1 was replaced by raw material 6 to synthesize the intermediates shown in Table 4:

Table 4: Preparation of intermediate IM-dX

Synthesis of intermediate IM-f-1

Under nitrogen protection, add intermediate IM-d-1 (20.04 g, 50 mmol), triphenylphosphine (32.78 g, 125 mmol) and o-dichlorobenzene (160 mL) to a 250 mL three-necked flask, start stirring and heating, and raise the temperature to reflux for 16 h. After the system is cooled to room temperature, The solvent was removed by distillation under reduced pressure to obtain a crude product. The crude product was purified by silica gel column chromatography using n-heptane as the mobile phase to obtain a white solid intermediate IM-e-1 (12.54 g, yield 68%).

Under nitrogen protection, bromobenzene (7.85 g, 50 mmol), intermediate IM-e-1 (18.44 g, 50 mmol), tris(dibenzylideneacetone)dipalladium (0.916 g, 1 mmol), (2-dicyclohexylphosphine-2', 4', 6'triisopropylbiphenyl) (0.95 g, 2 mmol), sodium tert-butoxide (9.61 g, 100 mmol) and xylene (250 mL) were added to a 500 mL three-necked flask in sequence, and the temperature was raised to reflux, and the reaction was stirred overnight; after the system was cooled to room temperature, it was extracted with dichloromethane (100 mL × 3 times), the organic phases were combined and dried over anhydrous sodium sulfate, filtered and the solvent was removed by reduced pressure distillation to obtain a crude product. The crude product was purified by silica gel column chromatography using n-heptane/dichloromethane as the mobile phase to obtain a white solid intermediate IM-f-1 (16.24 g; yield 73%).

Referring to the synthesis method of intermediate IM-f-1, the intermediate IM-a-1 is replaced by raw material 7 in Table 5, and bromobenzene is replaced by raw material 8 to synthesize the intermediates shown in Table 5:

Table 5: Preparation of intermediate IM-fX

Synthesis of compound 1

The intermediate IM-f-1 (5.83 g; 13.1 mmol), diphenylamine (2.22 g; 13.1 mmol), tris(dibenzylideneacetone)dipalladium (0.2 g; 0.3 mmol), 2-dicyclohexylphosphine-2,6-dimethoxybiphenyl (0.2 g; 0.5 mmol), sodium tert-butoxide (1.9 g; 19.7 mmol) and toluene (100 mL) were added to a round-bottom flask protected by nitrogen, heated to 110°C under stirring, and reacted for 16 hours; the reaction solution was cooled to room temperature, washed with water, separated from the organic phase, dried with anhydrous magnesium sulfate, and the solvent was removed under reduced pressure; the crude product was purified by silica gel column chromatography using dichloromethane/n-heptane, and then recrystallized and purified using toluene/n-heptane to obtain a white solid compound 1 (5.75 g; yield 76%). Mass spectrum: m/z=578.2[M+H] ⁺ .

The compounds shown in Table 6 were synthesized by referring to the synthesis method of compound 1, except that raw material 9 was used instead of intermediate IM-f-1, and raw material 10 was used instead of diphenylamine to prepare the compounds shown in Table 6 below:

Table 6: Compound structure preparation and characterization data

Synthesis of compound 25

Under nitrogen protection, add intermediate IM-d-6 (18.32 g, 50 mmol), triphenylphosphine (32.78 g, 125 mmol) and o-dichlorobenzene (160 mL) to a 250 mL three-necked flask, start stirring and heating, and heat to reflux reaction for 16 h. After the system is cooled to room temperature, the solvent is removed by vacuum distillation to obtain a crude product. The crude product is purified by silica gel column chromatography using n-heptane as the mobile phase to obtain a white solid intermediate IM-e-6 (11.03 g, yield 66%).

Under nitrogen protection, 4-bromotriphenylamine (16.21 g, 50 mmol), intermediate IM-e-6 (16.72 g, 50 mmol), tris(dibenzylideneacetone)dipalladium (0.916 g, 1 mmol), (2-dicyclohexylphosphine-2',4',6'triisopropylbiphenyl) (0.95 g, 2 mmol), sodium tert-butoxide (9.61 g, 100 mmol) and xylene (250 mL) were added to a 500 mL three-necked flask in sequence, and the temperature was raised to reflux, and the reaction was stirred overnight; after the system was cooled to room temperature, it was extracted with dichloromethane (100 mL × 3 times), the organic phases were combined and dried over anhydrous sodium sulfate, filtered, and the solvent was removed by vacuum distillation to obtain a crude product. The crude product was purified by silica gel column chromatography using n-heptane/dichloromethane as the mobile phase to obtain a white solid compound 25 (20.80 g; yield 72%). Mass spectrum: m/z = 578.2 [M+H] ⁺ .

The compounds shown in Table 7 were synthesized by referring to the synthesis method of compound 25, except that raw material 11 was used instead of intermediate IM-d-6, and raw material 12 was used instead of 4-bromotriphenylamine to prepare the compounds shown in Table 7 below

Table 7: Compound structure preparation and characterization data

The NMR data of some compounds are shown in Table 8 below.

Table 8

Preparation and evaluation of organic electroluminescent devices:

The present application also provides an organic electroluminescent device, including an anode, a cathode, and a functional layer between the anode and the cathode, wherein the functional layer includes the organic compound of the present application. The organic electroluminescent device of the present application is described in detail below by way of examples. However, the following examples are merely examples of the present application, and do not limit the present application.

Example 1: Preparation of red organic electroluminescent device

Substrate processing: The thickness is The ITO/Ag/ITO substrate is pretreated, the substrate surface is cleaned with an organic solvent to remove scum, and the surface is treated with ultraviolet ozone and O ₂ :N ₂ plasma to improve the substrate anode work function.

PD and compound HT-22 were co-evaporated at an evaporation rate ratio of 2%:98% to form a film with a thickness of A hole injection layer (HIL) is formed by evaporating HT-22 on the hole injection layer to form a thickness of The first hole transport layer is formed by a plurality of holes.

HT-23 was vacuum-deposited on the hole transport layer to form a layer with a thickness of The second hole transport layer is formed by a plurality of holes.

Then, on the second hole transport layer, compound 1: RH-N: RD was evaporated at a rate ratio of 48%: 48%: 4%. Co-evaporation to form The red organic light-emitting layer.

ET-1 and LiQ were evaporated at a rate ratio of 1:1. As the electron transport layer, Yb was evaporated An electron injection layer is made on the electron transport layer, and then magnesium and silver are evaporated at a deposition rate of 1:10. On the electron injection layer, a cathode is formed.

Finally, the cathode is evaporated CP-1 is used to form an organic covering layer, thereby completing the manufacture of a red organic light-emitting device.

Embodiments 2 to 27

A red organic electroluminescent device was prepared by the same method as in Example 1, except that the compound 1 in Example 1 was replaced by the compound shown in Table 9.

Comparative Example

Comparative Example 1: Compound D was used instead of Compound 1 in Example 1, and a red organic electroluminescent device was prepared in the same manner as Example 1.

In Comparative Example 2, Compound E was used instead of Compound 1 in Example 1, and a red organic electroluminescent device was prepared in the same manner as in Example 1.

Comparative Example 3: Compound F was used instead of Compound 1 in Example 1, and a red organic electroluminescent device was prepared in the same manner as Example 1.

In Examples 1 to 27 and Comparative Examples 1 to 3, the structural formulas of the materials used are as follows:

The performance of the red organic electroluminescent device prepared as above was analyzed under the condition of 15 mA/cm ^2. The results are shown in Table 9 below:

Table 9: Device performance test results

According to Table 9, the organic compound of the present application is used in the organic electroluminescent device, compared with Comparative Examples 1 to 3, the current efficiency Cd/A is increased by at least 17.9%, and the T(95) life is increased by at least 12.9%.

It should be understood that the present application is not limited to the precise structures that have been described above and shown in the drawings, and that various modifications and changes may be made without departing from the scope thereof. The scope of the present application is limited only by the appended claims.

Claims

An organic compound, characterized in that the organic compound has a structure as shown in Formula 1:

Wherein, R1 is selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms or a substituted or unsubstituted heteroaryl group having 12 to 30 carbon atoms;

Ar is selected from a substituted or unsubstituted arylene group having 6 to 30 carbon atoms or a substituted or unsubstituted heteroarylene group having 12 to 30 carbon atoms;

R 4 is selected from hydrogen or a group represented by formula 2;

R2 and R3 are the same or different and are independently selected from hydrogen, deuterium, cyano, halogen, aryl having 6 to 30 carbon atoms, heteroaryl having 3 to 30 carbon atoms or a group represented by Formula 2;

And only one of R 4 , R 2 and R 3 is a group represented by Formula 2;

L, L 1 , L 2 and L 3 are the same or different and are independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms or a substituted or unsubstituted heteroarylene group having 12 to 30 carbon atoms;

Ar 1 and Ar 2 are the same or different and are independently selected from a substituted or unsubstituted aryl group having 6 to 40 carbon atoms or a substituted or unsubstituted heteroaryl group having 12 to 40 carbon atoms;

The substituents in R 1 , L, L 1 , L 2 , Ar, Ar 1 and Ar 2 are the same or different and are independently selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, a heteroaryl group having 12 to 20 carbon atoms, a deuterated aryl group having 6 to 20 carbon atoms, a halogenated aryl group having 6 to 20 carbon atoms, a trialkylsilyl group having 3 to 12 carbon atoms, a triarylsilyl group having 18 to 24 carbon atoms, a halogenated alkyl group having 1 to 10 carbon atoms, a deuterated alkyl group having 1 to 10 carbon atoms or an aryl group having 6 to 20 carbon atoms;

Optionally, in Ar 1 and Ar 2 , any two adjacent substituents form a ring.
The organic compound according to claim 1, characterized in that the substituents in R 1 , L, L 1 , L 2 , Ar, Ar 1 and Ar 2 are the same or different and are independently selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, a heteroaryl group having 12 to 20 carbon atoms, a deuterated aryl group having 6 to 20 carbon atoms, a halogenated aryl group having 6 to 20 carbon atoms, a trialkylsilyl group having 3 to 12 carbon atoms, a triarylsilyl group having 18 to 24 carbon atoms, a halogenated alkyl group having 1 to 10 carbon atoms or a deuterated alkyl group having 1 to 10 carbon atoms.
The organic compound according to claim 1 or 2, characterized in that the organic compound is selected from the compounds represented by Formula 1-1, Formula 1-2 or Formula 1-3:
The organic compound according to claim 1 or 2, characterized in that L, L 1 , L 2 and L 3 are the same or different and are independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 15 carbon atoms, or a substituted or unsubstituted heteroarylene group having 12 to 20 carbon atoms;

Preferably, the substituents in L, L 1 , L 2 and L 3 are the same or different and are independently selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 5 carbon atoms or a phenyl group.
The organic compound according to claim 1 or 2, characterized in that L, L 1 , L 2 and L 3 are the same or different and are independently selected from a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted fluorenylene group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted carbazolylene group, a substituted or unsubstituted dibenzofuranyl group or a substituted or unsubstituted dibenzothiophenylene group;

Preferably, the substituents in L, L 1 , L 2 and L 3 are the same or different and are independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl or phenyl.
The organic compound according to claim 1 or 2, characterized in that Ar 1 and Ar 2 are the same or different and are independently selected from a substituted or unsubstituted aryl group having 6 to 25 carbon atoms or a substituted or unsubstituted heteroaryl group having 12 to 24 carbon atoms;

Preferably, the substituents in Ar 1 and Ar 2 are the same or different and are independently selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 5 carbon atoms or a phenyl group;

Optionally, in Ar 1 and Ar 2 , any two adjacent substituents form a fluorene ring.
The organic compound according to claim 1 or 2, characterized in that Ar 1 and Ar 2 are the same or different and are independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted triphenylene, substituted or unsubstituted fluorenyl, substituted or unsubstituted spirobifluorenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl or substituted or unsubstituted carbazolyl;

Preferably, the substituents in Ar 1 and Ar 2 are the same or different and are independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl or phenyl.
The organic compound according to claim 1 or 2, characterized in that The same or different, each independently selected from the group consisting of the following groups:
The organic compound according to claim 1 or 2, characterized in that R 1 is selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothienyl or substituted or unsubstituted carbazolyl;

Preferably, the substituents in R 1 are the same or different and are independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl or phenyl.
The organic compound according to claim 1 or 2, characterized in that Ar is selected from substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted biphenylene, substituted or unsubstituted fluorenylene, substituted or unsubstituted carbazolylene, substituted or unsubstituted dibenzothiophenylene or substituted or unsubstituted dibenzofuranylene;

The substituents in Ar are the same or different and are independently selected from hydrogen, deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl or phenyl;

R 4 is selected from hydrogen or a group represented by formula 2;

R2 and R3 are the same or different and are independently selected from hydrogen or a group represented by Formula 2;

And only one of R 4 , R 2 and R 3 is a group represented by Formula 2.
The organic compound according to claim 1 or 2, characterized in that the organic compound is selected from the group consisting of the following compounds:
An organic electroluminescent device, characterized in that it comprises an anode and a cathode arranged opposite to each other, and a functional layer arranged between the anode and the cathode;

The functional layer comprises the organic compound according to any one of claims 1 to 11;

Preferably, the functional layer comprises an organic light-emitting layer; the organic light-emitting layer comprises the organic compound;

Preferably, the organic electroluminescent device is a red organic electroluminescent device.
An electronic device, characterized by comprising the organic electroluminescent device according to claim 12.