CN113292566A

CN113292566A - Organic compound, application thereof, organic electroluminescent device using organic compound and electronic device

Info

Publication number: CN113292566A
Application number: CN202110179074.6A
Authority: CN
Inventors: 刘文强; 马天天; 韩超
Original assignee: Shaanxi Lighte Optoelectronics Material Co Ltd
Current assignee: Shaanxi Lighte Optoelectronics Material Co Ltd
Priority date: 2020-04-28
Filing date: 2021-02-09
Publication date: 2021-08-24
Anticipated expiration: 2041-02-09
Also published as: CN113292566B; WO2021218829A1

Abstract

The application provides an organic compound with structures shown in formulas I-1 and I-2, application thereof, an organic electroluminescent device and an electronic device using the organic compound, and belongs to the technical field of organic materials. The organic compound is applied to a light emitting layer of an organic light emitting device, so that the driving voltage of the device can be reduced, the current efficiency and the light emitting efficiency can be improved, and the service life of the device can be greatly prolonged.

Description

Organic compound, application thereof, organic electroluminescent device using organic compound and electronic device

Technical Field

The application belongs to the technical field of organic materials, and particularly provides an organic compound, application thereof, an organic electroluminescent device using the organic compound and an electronic device using the organic compound.

Background

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

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

At present, the problems of reduced luminous efficiency, shortened service life and the like exist in the using process of an organic electroluminescent device, so that the performance of the organic electroluminescent device is reduced.

Disclosure of Invention

The purpose of the present application is to provide an organic electroluminescent material having excellent properties, which can be used as a light-emitting layer in an organic electroluminescent device.

In order to achieve the above object, the present application provides an organic compound having a structure represented by formula I-1 and formula I-2:

wherein represents the point of attachment of formula I-1 fused to formula I-2;

a is selected from benzene ring or condensed aromatic ring with ring carbon number of 10-14;

L₁and L₂The same or different from each other, and each is independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms;

R₁、R₂、R₃、R₄and R₅The same or different from each other, and are independently selected from deuterium, cyano group, halogen group, substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, trialkylsilyl group having 3 to 12 carbon atoms, substituted or unsubstituted aryl group having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms, or any two adjacent R₁The atoms linked to each other to be common to them form a ring, or any two adjacent R₂The atoms linked to each other to be common to them form a ring, or any two adjacent R₃The atoms linked to each other to be common to them form a ring, or any two adjacent R₄The atoms linked to each other to be common to them form a ring, or any two adjacent R₅Atoms that are linked to each other to be commonly bound to them form a ring;

R₆selected from substituted or unsubstituted alkyl with 1-20 carbon atoms, substituted or unsubstituted aryl with 6-30 carbon atoms, substituted or unsubstituted heteroaryl with 3-30 carbon atoms, and substituted or unsubstituted cycloalkyl with 3-20 carbon atoms;

n₁-n₅with n_tIs represented by R₁-R₅With R_tIs represented by t is a variable and represents an arbitrary integer of 1 to 5, n_tRepresents a substituent R_tThe number of (2); when t is 1 or 3, n_tSelected from 0, 1,2, 3, 4; when t is 2, n_tSelected from 0, 1,2, 3; when t is 4, n_tSelected from 0, 1, 2; when t is 5, n_tSelected from 0, 1,2, 3,4, 5, 6, 7, 8, 9, 10; when n is_tWhen greater than 1, any two R_tThe same or different;

R₁、R₂、R₃、R₄、R₅、R₆、L₁and L₂Each substituent of (a) is independently selected from: deuterium, fluorine, chlorine, bromine, cyano, heteroaryl having 3 to 20 carbon atoms, aryl having 6 to 20 carbon atoms, trialkylsilyl having 3 to 12 carbon atoms, arylsilyl having 8 to 12 carbon atoms, alkyl having 1 to 10 carbon atoms, haloalkyl having 1 to 10 carbon atoms, cycloalkyl having 3 to 10 carbon atoms, heterocycloalkyl having 2 to 10 carbon atoms, alkoxy having 1 to 10 carbon atoms;

at R₆And L₂When two substituents are present on the same atom, optionally, the two substituents are linked to each other to form, together with the atom to which they are commonly attached, a 5-13 membered saturated or unsaturated ring.

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

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

The organic compound of the present application has an adamantane spirofluorene group and a nitrogen-containing fused heteroaryl group as main structures, and contains a substituent. On one hand, the compound taking the nitrogen-containing condensed heteroaryl as a main group has high electron mobility, and the electron mobility of the compound is obviously improved as a plurality of groups are connected. On one hand, the spiro ring formed by the spiro ring and the adamantane is a three-dimensional spatial structure, so that the aggregation among molecules can be effectively prevented, and the spiro ring is not easy to crystallize; the strong rigidity of the spiro ring ensures that the compound has stable structure. On the other hand, the compound structure has an extensible three-dimensional structure, and the continuous pi-conjugate is used for bringing better electron mobility, so that the compound has high electron mobility; and, the combination of the three makes the carrier transport balanced. The organic light emitting diode is applied to an organic light emitting device and used as a light emitting layer, the driving voltage of the device can be reduced, the current efficiency and the light emitting efficiency are improved, and the service life of the device can be greatly prolonged on the premise that the driving voltage and the light emitting efficiency are similar.

Additional features and advantages of the present application will be described in detail in the detailed description which follows.

Drawings

The accompanying drawings, which are included to provide a further understanding of the application and are incorporated in and constitute a part of this specification, illustrate embodiments of the application and together with the description serve to explain the principles of the application and not to limit the application. In the drawings:

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

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

Fig. 3 is a schematic structural view of a photoelectric conversion device according to an embodiment of the present application.

Fig. 4 is a schematic structural diagram of a second electronic device according to an embodiment of the present application.

Description of the reference numerals

100. An anode; 200. a cathode; 300. a functional layer; 310. a hole injection layer; 320. a hole transport layer; 321. a first hole transport layer; 322. a second hole transport layer; 330. an organic light emitting layer; 340. an electron transport layer; 350. an electron injection layer; 400. a first electronic device; 500. a second electronic device.

Detailed Description

The following detailed description of embodiments of the present application will be made with reference to the accompanying drawings. It should be understood that the detailed description and specific examples, while indicating the present application, are given by way of illustration and explanation only, and are not intended to limit the present application.

The present application provides an organic compound having the structure shown in formula I-1 and formula I-2:

wherein represents the point of attachment of the fusion of formula I-1 with formula I-2;

Specifically, ring a may be a benzene ring or a naphthalene ring.

In the present application, since adamantane is a three-dimensional structure, in the structure diagram of the compound, different structural formulas are shown because of different drawing modes, and the cyclic structures formed on 9, 9-dimethylfluorene are all adamantane, and the connection positions are also the same. For example:

all have the same structure.

In the present application, the descriptions "… … is independently" and "… … is independently" and "… … is independently selected from" are interchangeable, and should be understood in a broad sense, which means that the specific items expressed between the same symbols do not affect each other in different groups, or that the specific items expressed between the same symbols do not affect each other in the same groups. For example,

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

In this application A, L₁、L₂、R₁To R₆The number of carbon atoms of (b) means all the number of carbon atoms. For example, if L₁Selected from the group consisting of substituted arylene having 12 carbon atoms, such that the total number of carbon atoms of the arylene group and the substituents thereon is 12。

In the present application, the term "substituted or unsubstituted" means that a functional group described later in the term may or may not have a substituent (hereinafter, for convenience of description, the substituent is collectively referred to as Rc). For example, "substituted or unsubstituted aryl" refers to an aryl group or an unsubstituted aryl group having a substituent Rc. Wherein Rc as the substituent may be, for example, deuterium, fluorine, chlorine, bromine, cyano, heteroaryl having 3 to 20 carbon atoms, aryl having 6 to 20 carbon atoms, trialkylsilyl having 3 to 12 carbon atoms, arylsilyl having 8 to 12 carbon atoms, alkyl having 1 to 10 carbon atoms, haloalkyl having 1 to 10 carbon atoms, alkenyl having 2 to 6 carbon atoms, alkynyl having 2 to 6 carbon atoms, cycloalkyl having 3 to 10 carbon atoms, heterocycloalkyl having 2 to 10 carbon atoms, cycloalkenyl having 5 to 10 carbon atoms, heterocycloalkenyl having 4 to 10 carbon atoms, alkoxy having 1 to 10 carbon atoms, alkylamino having 1 to 10 carbon atoms, alkylthio having 1 to 10 carbon atoms, aryloxy having 6 to 18 carbon atoms, aryloxy having 1 to 18 carbon atoms, heteroaryl having 1 to 10 carbon atoms, heteroarylene, or a heteroarylene, Arylthio group having 6 to 18 carbon atoms, alkylsulfonyl group having 6 to 18 carbon atoms, trialkylphosphino group having 3 to 18 carbon atoms, trialkylboron group having 3 to 18 carbon atoms. In the present application, a "substituted" functional group may be substituted with one or 2 or more substituents in the above Rc; when two substituents Rc are attached to the same atom, these two substituents Rc may be independently present or attached to each other to form a ring with the atom; when two adjacent substituents Rc exist on a functional group, the adjacent two substituents Rc may exist independently or may form a ring fused with the functional group to which they are attached.

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

In this application, aryl refers to an optional functional group or substituent derived from an aromatic carbocyclic ring. The aryl group may be a monocyclic aryl group (e.g., phenyl) or a polycyclic aryl group, in other words, the aryl group may be a monocyclic aryl group, a fused ring aryl group, two or more groups conjugated by a carbon-carbon bondMore monocyclic aryl groups, monocyclic aryl and fused ring aryl groups linked by carbon-carbon bond conjugates, two or more fused ring aryl groups linked by carbon-carbon bond conjugates. That is, unless otherwise specified, two or more aromatic groups conjugated through a carbon-carbon bond may also be considered as aryl groups herein. The fused ring aryl group may include, for example, a bicyclic fused aryl group (e.g., naphthyl group), a tricyclic fused aryl group (e.g., phenanthryl group, fluorenyl group, anthracyl group), and the like. The aryl group does not contain a hetero atom such as B, N, O, S, P, Se or Si. For example, biphenyl, terphenyl, and the like are aryl groups in this application. Examples of aryl groups may include, but are not limited to, phenyl, naphthyl, fluorenyl, anthracyl, phenanthryl, biphenyl, terphenyl, quaterphenyl, pentabiphenyl, benzo [9,10 ]]Phenanthryl, pyrenyl, benzofluoranthenyl, phenanthrenyl, pyrenyl,

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

As the aryl group as a substituent in the present application, there may be mentioned, for example, a phenyl group, a biphenyl group, a naphthyl group, a 9, 9-dimethylfluorenyl group, a 9, 9-diphenylfluorenyl group, a spirobifluorenyl group, an anthracenyl group, a phenanthrenyl group, a,

And (4) a base.

In the present application, substituted aryl groups may be aryl groups in which one or two or more hydrogen atoms are substituted with groups such as deuterium atoms, halogen groups, cyano groups, aryl groups, heteroaryl groups, trialkylsilyl groups, alkyl groups, cycloalkyl groups, alkoxy groups, alkylthio groups, and the like. Specific examples of heteroaryl-substituted aryl groups include, but are not limited to, dibenzofuranyl-substituted phenyl, dibenzothiophene-substituted phenyl, pyridine-substituted phenyl, and the like. It is 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 having a carbon number of 18 refers to the total number of carbon atoms of the aryl group and the substituent being 18.

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

In the present application, substituted heteroaryl groups may be heteroaryl groups in which one or more hydrogen atoms are substituted with groups such as deuterium atoms, halogen groups, cyano groups, aryl groups, heteroaryl groups, trialkylsilyl groups, alkyl groups, cycloalkyl groups, alkoxy groups, alkylthio groups, and the like. Specific examples of aryl-substituted heteroaryl groups include, but are not limited to, phenyl-substituted dibenzofuranyl, phenyl-substituted dibenzothiophenyl, phenyl-substituted pyridyl, and the like. It is understood that the number of carbon atoms in the substituted heteroaryl group refers to the total number of carbon atoms in the heteroaryl group and the substituent on the heteroaryl group.

In the present application, heteroaryl as a substituent is, for example, pyridyl, pyrimidinyl, carbazolyl, dibenzofuranyl, dibenzothienyl, quinolyl, quinazolinyl, quinoxalinyl.

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

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

For example, as shown in the following formula (f), naphthyl represented by formula (f) is connected with other positions of the molecule through two non-positioned connecting bonds penetrating through a double ring, and the meaning of the naphthyl represented by the formula (f-1) to the formula (f-10) comprises any possible connecting mode shown in the formula (f-1) to the formula (f-10).

As another example, as shown in the following formula (X '), the phenanthryl group represented by formula (X') is bonded to other positions of the molecule via an delocalized bond extending from the middle of the benzene ring on one side, and the meaning of the phenanthryl group includes any of the possible bonding modes as shown in formulas (X '-1) to (X' -4).

An delocalized substituent, as used herein, refers to a substituent attached by a single bond extending from the center of the ring system, meaning that the substituent may be attached at any possible position in the ring system. For example, as shown in the following formula (Y), the substituent R' represented by the formula (Y) is bonded to the quinoline ring via an delocalized bond, and the meaning thereof includes any of the possible bonding modes as shown in the formulae (Y-1) to (Y-7).

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

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

In this application, the explanation for aryl applies to arylene and the explanation for heteroaryl applies equally to heteroarylene.

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

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

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

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

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

In one embodiment of the present application, the organic compound has a structure represented by any one of formulas 2-1 to 2-24:

in one embodiment of the present application, the L₁And L₂Each independently selected from the group consisting of a single bond or the following groups:

wherein M is₁Selected from a single bond or

Q₁～Q₅And Q'₁～Q’₄Each independently selected from N or C (F)₁) And Q is₁～Q₅At least one is selected from N; when Q is₁～Q₅Two or more of C (F)₁) When, two arbitrary F₁Same or different, when Q'₁～Q’₄Two or more of C (F)₁) When, two arbitrary F₁The same or different;

Q₆～Q₁₃each independently selected from N or C (F)₂) And Q is₆～Q₁₃At least one is selected from N; when Q is₆～Q₁₃Two or more of C (F)₂) When, two arbitrary F₂The same or different;

Q₁₄～Q₂₃each independently selected from N orC (F)₃) And Q is₁₄～Q₂₃At least one is selected from N; when Q is₁₄～Q₂₃Two or more of C (F)₃) When, two arbitrary F₃The same or different;

each E₁～E₆、F₁～F₃Equal to or different from each other, each independently selected from: hydrogen, deuterium, fluorine, chlorine, bromine, cyano, heteroaryl with 3-20 carbon atoms, aryl with 6-20 carbon atoms, trialkylsilyl with 3-12 carbon atoms, arylsilyl with 8-12 carbon atoms, alkyl with 1-10 carbon atoms, haloalkyl with 1-10 carbon atoms, cycloalkyl with 3-10 carbon atoms, heterocycloalkyl with 2-10 carbon atoms, and alkoxy with 1-10 carbon atoms;

e₁～e₆with e_rIs represented by₁～E₆With E_rR is a variable and is an arbitrary integer of 1 to 6, e_rRepresents a substituent E_rThe number of (2); when r is selected from 1,2, 3, 6, e_rSelected from 1,2, 3 or 4; when r is selected from 4, e_rSelected from 1,2, 3,4, 5 or 6; when r is 5, e_rSelected from 1,2, 3,4, 5; when e is_rWhen greater than 1, any two of E_rThe same or different;

K₁selected from O, S, Se, N (E)₇)、C(E₈E₉)、Si(E₁₀E₁₁) (ii) a Wherein E is₇、E₈、E₉、E₁₀、E₁₁Are the same or different from each other and are each independently selected from: aryl having 6 to 20 carbon atoms, heteroaryl having 3 to 20 carbon atoms, alkyl having 1 to 10 carbon atoms, cycloalkyl having 3 to 10 carbon atoms, heterocycloalkyl having 2 to 10 carbon atoms, or E₈And E₉Are linked to each other to form, together with the atoms to which they are commonly attached, a 5-to 13-membered saturated or unsaturated ring, or E₁₀And E₁₁Are linked to form, together with the atoms to which they are commonly attached, a 5-13 membered saturated or unsaturated ring, for example, in formula j-4

In (A) when M₁When it is a single bond, E₅Are each hydrogen, K₂Is a single bond, K₁Is C (E)₈E₉) When is optional, E₈And E₉The atoms that are linked to each other to form a 5-13 membered saturated or unsaturated ring with the atoms to which they are commonly attached refer to: e₈And E₉Can be connected with each other to form a ring, and can also exist independently; when E is₈And E₉When the ring is formed, the number of carbon atoms of the ring may be 5-membered, for example

Or may be a 6-membered ring, e.g.

And may also be a 13-membered ring, e.g.

Of course, E₈And E₉The number of carbon atoms forming the ring can also be other values, which are not listed one by one, and the number of carbon atoms forming the ring is not particularly limited in the present application;

K₂selected from the group consisting of a single bond, O, S, Se, N (E)₁₂)、C(E₁₃E₁₄)、Si(E₁₅E₁₆) (ii) a Wherein E is₁₂、E₁₃、E₁₄、E₁₅、E₁₆Are the same or different from each other and are each independently selected from: aryl having 6 to 20 carbon atoms, heteroaryl having 3 to 20 carbon atoms, alkyl having 1 to 10 carbon atoms, cycloalkyl having 3 to 10 carbon atoms, heterocycloalkyl having 2 to 10 carbon atoms, or E₁₃And E₁₄Are linked to each other to form, together with the atoms to which they are commonly attached, a 5-to 13-membered saturated or unsaturated ring, or E₁₅And E₁₆Are linked to each other to form, together with the atoms to which they are commonly attached, a 5-to 13-membered saturated or unsaturated ring, not E₁₃And E₁₄Number of carbon atoms in Ring formation, E₁₅And E₁₆The number of carbon atoms forming the ring is specifically defined, E₁₃And E₁₄Cyclization E₁₅And E₁₆Number of carbon atoms in Ring formation and E₈And E₉The same ring formation process is not repeated here.

In one embodiment of the present application, the L₁、L₂Each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, and a substituted or unsubstituted heteroarylene group having 3 to 20 carbon atoms.

In one embodiment of the present application, the L₁、L₂Each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 12 carbon atoms, and a substituted or unsubstituted heteroarylene group having 3 to 15 carbon atoms.

In one embodiment of the present application, the L₁、L₂Each independently selected from the group consisting of a single bond or the following groups:

in one embodiment of the present application, L₁And L₂The substituents on (A) are selected from deuterium, fluorine, chlorine, bromine, cyano, phenyl, naphthyl, biphenyl, pyridyl, methyl, ethyl, isopropyl, tert-butyl, trimethylsilyl.

In one embodiment of the present application, L₁And L₂The substituent is selected from deuterium, fluorine, chlorine, bromine, cyano, heteroaryl with 3-10 carbon atoms, aryl with 6-12 carbon atoms, trialkylsilyl with 3-12 carbon atoms and alkyl with 1-5 carbon atoms.

In one embodiment of the present application, each R is₁、R₂、R₃、R₄、R₅The same or different from each other, and each independently selected from deuterium, cyano group, halogen group, trialkylsilyl group having 3-10 carbon atoms, unsubstituted alkyl group having 1-5 carbon atoms, or the group consisting of;

R₆independently selected from the group consisting of unsubstituted alkyl groups having 1 to 5 carbon atoms or:

wherein M is₂Selected from a single bond or

Z₁～Z₅And Z'₁～Z’₄Each independently selected from N or C (F)₄) And Z is₁～Z₅At least one is selected from N; when Z is₁～Z₅Two or more of C (F)₄) When, two arbitrary F₄The same or different; z'₁～Z’₄Two or more of C (F)₄) When, two arbitrary F₄The same or different;

Z₆～Z₁₃each independently selected from N or C (F)₅) And Z is₆～Z₁₃At least one is selected from N; when Z is₆～Z₁₃Two or more of C (F)₅) When, two arbitrary F₅The same or different;

Z₁₄～Z₂₃each independently selected from N or C (F)₆) And Z is₁₄～Z₂₃At least one is selected from N; when Z is₁₄～Z₂₃Two or more of C (F)₆) When, two arbitrary F₆The same or different;

G₁selected from: hydrogen, deuterium, fluorine, chlorine, bromine, cyano, trialkylsilyl having 3 to 12 carbon atoms, arylsilyl having 8 to 12 carbon atoms, alkyl having 1 to 10 carbon atoms, or C1-a haloalkyl group having 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, a heterocycloalkyl group having 2 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms;

each G₂～G₆、G₁₂Are the same or different from each other and are each independently selected from: hydrogen, deuterium, fluorine, chlorine, bromine, cyano, heteroaryl having 3 to 20 carbon atoms, trialkylsilyl having 3 to 12 carbon atoms, arylsilyl having 8 to 12 carbon atoms, alkyl having 1 to 10 carbon atoms, haloalkyl having 1 to 10 carbon atoms, cycloalkyl having 3 to 10 carbon atoms, heterocycloalkyl having 2 to 10 carbon atoms, and alkoxy having 1 to 10 carbon atoms;

each G₇～G₁₁、F₄～F₆Are the same or different from each other and are each independently selected from: hydrogen, deuterium, fluorine, chlorine, bromine, cyano, aryl of 6 to 20 carbon atoms optionally substituted by deuterium, fluorine, chlorine, bromine, cyano, heteroaryl of 3 to 20 carbon atoms, trialkylsilyl of 3 to 12 carbon atoms, arylsilyl of 8 to 12 carbon atoms, alkyl of 1 to 10 carbon atoms, haloalkyl of 1 to 10 carbon atoms, cycloalkyl of 3 to 10 carbon atoms, heterocycloalkyl of 2 to 10 carbon atoms, alkoxy of 1 to 10 carbon atoms, in which case "aryl of 6 to 20 carbon atoms optionally substituted by deuterium, fluorine, chlorine, bromine, cyano" means that aryl may or may not be substituted by deuterium, fluorine, chlorine, bromine, cyano;

g₁～g₁₂in g_kIs represented by G₁～G₁₂With G_kK is a variable and is an arbitrary integer of 1 to 12, and g_kRepresents a substituent G_kThe number of (2); wherein, when k is selected from 2, 4, 5, 8, 12, g_kSelected from 1,2, 3 or 4; when k is selected from 1,3, 6, g_kSelected from 1,2, 3,4 or 5; when k is selected from 9 and 10, g_kSelected from 1,2, 3,4, 5 or 6; when k is selected from 7, g_kSelected from 1,2, 3,4, 5, 6 or 7; when k is selected from 11, g_kSelected from 1,2, 3,4, 5, 6, 7 or 8; when g is_kWhen greater than 1, any two G_kThe same or different;

K₁selected from O, S, Se, N (G)₁₃)、C(G₁₄G₁₅)、Si(G₁₆G₁₇) (ii) a Wherein G is₁₃～G₁₇Are the same or different from each other and are each independently selected from: aryl group having 6 to 20 carbon atoms, heteroaryl group having 3 to 20 carbon atoms, alkyl group having 1 to 10 carbon atoms, cycloalkyl group having 3 to 10 carbon atoms, heterocycloalkyl group having 2 to 10 carbon atoms, or G₁₄And G₁₅Are linked to each other to form, together with the atoms to which they are commonly attached, a 5-13 membered saturated or unsaturated ring, or G₁₆And G₁₇Are linked to each other to form, together with the atoms to which they are commonly attached, a 5-to 13-membered saturated or unsaturated ring, not G₁₄And G₁₅Number of carbon atoms in Ring formation, G₁₆And G₁₇The number of carbon atoms forming the ring is specifically defined, G₁₄And G₁₅Cyclization G₁₆And G₁₇Number of carbon atoms in Ring formation and E₈And E₉The same ring formation process is not repeated herein;

K₂selected from single bond, O, S, Se, N (G)₁₈)、C(G₁₉G₂₀)、Si(G₂₁G₂₂) (ii) a Wherein G is₁₈～G₂₂Each independently selected from: aryl group having 6 to 20 carbon atoms, heteroaryl group having 3 to 20 carbon atoms, alkyl group having 1 to 10 carbon atoms, cycloalkyl group having 3 to 10 carbon atoms, heterocycloalkyl group having 2 to 10 carbon atoms, or G₁₉And G₂₀Are linked to each other to form, together with the atoms to which they are commonly attached, a 5-13 membered saturated or unsaturated ring, or G₂₁And G₂₂Are linked to each other to form, together with the atoms to which they are commonly attached, a 5-to 13-membered saturated or unsaturated ring, not G₁₉And G₂₀Number of carbon atoms in Ring formation, G₂₁And G₂₂The number of carbon atoms forming the ring is specifically defined, G₁₉And G₂₀Cyclization G₂₁And G₂₂Number of carbon atoms in Ring formation and E₈And E₉The same ring formation process is not repeated here.

In one embodiment of the present application, each R₁、R₂、R₃、R₄、R₅The same or different from each other, and each is independently selected from deuterium, cyano, fluorine, trimethylsilyl, triphenylsilyl, substituted or unsubstituted alkyl having 1 to 5 carbon atoms, substituted or unsubstituted aryl having 6 to 20 carbon atoms, and substituted or unsubstituted heteroaryl having 3 to 25 carbon atoms;

R₆selected from substituted or unsubstituted alkyl with 1-10 carbon atoms, substituted or unsubstituted aryl with 6-20 carbon atoms and substituted or unsubstituted heteroaryl with 3-25 carbon atoms.

In one embodiment of the present application, R₆Selected from alkyl groups having 1 to 5 carbon atoms or substituted or unsubstituted W selected from the group consisting of:

when the W group is substituted, the substituent of W is selected from deuterium, fluorine, chlorine, cyano, trimethylsilyl, halogenated alkyl with 1-4 carbon atoms, methyl, tert-butyl, phenyl, carbazolyl, furyl, biphenyl, pyridyl, naphthyl and carbazolyl; when there are a plurality of substituents for W, the substituents may be the same or different.

In another embodiment of the present application, R₆Each independently selected from the group consisting of alkyl groups having 1 to 5 carbon atoms or groups consisting of:

in one embodiment of the present application, the R is₆Selected from substituted or unsubstituted alkyl with 1-5 carbon atoms, substituted or unsubstituted aryl with 6-18 carbon atoms or substituted or unsubstituted heteroaryl with 5-15 carbon atoms.

In one embodiment of the present application, each R₁、R₂、R₃、R₄、R₅Are identical or different from each other and are each independently selected fromDeuterium, cyano, fluoro, methyl, ethyl, isopropyl, tert-butyl, substituted or unsubstituted aryl having 6 to 18 carbon atoms, substituted or unsubstituted heteroaryl having 5 to 20 carbon atoms.

In one embodiment of the present application, each R₁、R₂、R₃、R₄、R₅Identical or different from each other and each independently selected from deuterium, cyano, fluoro, methyl, ethyl, isopropyl, tert-butyl or the following substituted or unsubstituted groups: phenyl, naphthyl, biphenyl, terphenyl, phenanthryl, anthracyl, 9-spirobifluorenyl, 9-dimethylfluorenyl, pyridyl, carbazolyl, pyrimidinyl, pyridazinyl, triazinyl, quinolinyl, quinazolinyl, phenylpyridinyl, quinoxalinyl, pyrenyl, N-phenylcarbazolyl, dibenzofuranyl or dibenzothiophenyl,

the substitution is substituted by a group selected from: deuterium, fluorine, chlorine, cyano, silicon base, methyl, ethyl, isopropyl, tert-butyl, halogenated alkyl with 1-4 carbon atoms, phenyl and pyridyl; when there are plural substituents, the plural substituents may be the same or different.

In one embodiment of the present application, R₆Each substituent of (a) is independently selected from: deuterium, fluorine, chlorine, bromine, cyano, methyl, ethyl, isopropyl, tert-butyl, phenyl, naphthyl, biphenyl, terphenyl, phenanthryl, anthracenyl, 9-spirobifluorenyl, 9-dimethylfluorenyl, pyridyl, carbazolyl, pyrimidinyl, pyridazinyl, triazinyl, quinolyl, quinazolinyl, quinoxalinyl, pyrenyl, N-phenylcarbazolyl, dibenzofuranyl, dibenzothienyl, trimethylsilyl, triphenylsilyl, or trifluoromethyl.

In one embodiment of the present application, L₁And L₂Each substituent of (a) is independently selected from: deuterium, fluorine, chlorine, bromine, cyano, methyl, ethyl, isopropyl, tert-butyl, phenyl, naphthyl, biphenyl, 9-dimethylfluorenyl, pyridyl, carbazolyl, pyrimidinyl, pyridazinyl, triazinyl, quinolyl, quinazolinyl, quinoxalinyl, pyrenyl, dibenzofuranyl, dibenzothienyl, trimethylsilyl, triphenylsilyl, or trifluoro-phenylA methyl group.

In one embodiment of the present application, the R is₁、R₂、R₃、R₄、R₅、R₆Each substituent of (a) is independently selected from: deuterium, fluorine, chlorine, bromine, cyano, heteroaryl having 3 to 12 carbon atoms, aryl having 6 to 12 carbon atoms, trialkylsilyl having 3 to 12 carbon atoms, arylsilyl having 8 to 12 carbon atoms, alkyl having 1 to 5 carbon atoms, and haloalkyl having 1 to 10 carbon atoms.

In one embodiment of the present application, n₁、n₂、n₃、n₄、n₅Are all selected from 0.

In one embodiment of the present application, the organic compound is selected from the group consisting of:

the synthesis method of the organic compound provided herein is not particularly limited, and those skilled in the art can determine an appropriate synthesis method according to the organic compound of the present invention in combination with the preparation method provided in the synthesis examples section. In other words, the synthetic examples section of the present invention illustratively provides methods for the preparation of organic compounds, and the starting materials employed may be obtained commercially or by methods well known in the art. All organic compounds provided herein are available to those skilled in the art from these exemplary preparative methods, and all specific preparative methods for preparing the organic compounds will not be described in detail herein, and those skilled in the art should not be construed as limiting the present application.

A second aspect of the present application provides the use of an organic compound as described in the first aspect of the present application in an organic electroluminescent device.

A third aspect of the present application provides an organic electroluminescent device comprising an anode and a cathode disposed opposite to each other, and a functional layer disposed between the anode and the cathode; the functional layer comprises an organic compound according to the first aspect of the present application.

The organic compound provided herein may be used to form at least one organic film layer in a functional layer to improve efficiency characteristics and lifetime characteristics of an organic electroluminescent device.

In a specific embodiment, the functional layer includes a light-emitting layer including the organic compound. The light-emitting layer may be composed of the organic compound provided herein, or may be composed of the organic compound provided herein together with other materials. The light-emitting layer may be one layer or two or more layers.

In one embodiment, the organic electroluminescent device is a red device or a green device.

Specifically, as shown in fig. 1, the organic electroluminescent device may include an anode 100, a first hole transport layer 321, a second hole transport layer 322, an organic light emitting layer 330 as an energy conversion layer, an electron transport layer 340, and a cathode 200, which are sequentially stacked.

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

Alternatively, the first hole transport layer 321 and the second hole transport layer 322 respectively include one or more hole transport materials, and the hole transport materials may be selected from carbazole multimers, carbazole-linked triarylamine compounds, or other types of compounds, which are not specifically limited in this application. For example, the first hole transport layer 321 may be composed of a compound NPB.

Alternatively, the organic light emitting layer 330 may be composed of a single light emitting material, and may also include a host material and a guest material. Alternatively, the organic light emitting layer 330 is composed of a host material and a guest material, and a hole injected into the organic light emitting layer 330 and an electron injected into the organic light emitting layer 330 may be combined in the organic light emitting layer 330 to form an exciton, which transfers energy to the host material, and the host material transfers energy to the guest material, thereby enabling the guest material to emit light.

The host material of the organic light emitting layer 330 may be a metal chelate compound, a bisstyryl derivative, an aromatic amine derivative, a dibenzofuran derivative, or other types of materials, which is not particularly limited in the present application.

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

The electron transport layer 340 may have a single-layer structure or a multi-layer structure, and may include one or more electron transport materials selected from, but not limited to, benzimidazole derivatives, oxadiazole derivatives, quinoxaline derivatives, or other electron transport materials. In one embodiment of the present application, the electron transport layer 340 may be composed of TPBi and LiQ.

In the present application, the cathode 200 may include a cathode material, which is a material having a small work function that facilitates electron injection into the functional layer. Specific examples of the cathode material 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 a multilayer material such as LiF/Al, Liq/Al, LiO₂Al, LiF/Ca, LiF/Al and BaF₂and/Ca. Preferably, a metal electrode comprising magnesium and silver is included as a cathode.

Optionally, as shown in fig. 1, a hole injection layer 310 may be further disposed between the anode 100 and the first hole transport layer 321 to enhance the ability to inject holes into the first hole transport layer 321. The hole injection layer 310 may be made of benzidine derivatives, starburst arylamine compounds, phthalocyanine derivatives, or other materials, which are not limited in this application. For example, the hole injection layer 310 may be composed of HAT-CN.

Optionally, as shown in fig. 1, an electron injection layer 350 may be further disposed between the cathode 200 and the electron transport layer 340 to enhance the ability to inject electrons into the electron transport layer 340. The electron injection layer 350 may include an inorganic material such as an alkali metal sulfide or an alkali metal halide, or may include a complex of an alkali metal and an organic material. For example, the electron injection layer 350 may include LiQ.

According to another embodiment, the organic electroluminescent device may be a photoelectric conversion device. As shown in fig. 3, the photoelectric conversion device may include an anode 100 and a cathode 200 disposed opposite to each other, and a functional layer 300 disposed between the anode 100 and the cathode 200; the functional layer 300 comprises an organic compound as provided herein.

According to an exemplary embodiment, as shown in fig. 3, the functional layer 300 includes an organic light emitting layer 330, and the organic light emitting layer 330 includes an organic compound of the present application. The organic light emitting layer 330 may be composed of the organic compound provided herein, or may be composed of the organic compound provided herein and other materials.

Optionally, the organic light emitting layer 330 may further include an inorganic doping material to improve light emitting performance of the organic light emitting layer 330.

According to a specific embodiment, as shown in fig. 3, the photoelectric conversion device may include an anode 100, a hole transport layer 320, an organic light emitting layer 330, an electron transport layer 340, and a cathode 200, which are sequentially stacked.

Alternatively, the photoelectric conversion device may be a solar cell, and particularly may be an organic thin film solar cell. For example, in one embodiment of the present application, a solar cell may include an anode, a hole transport layer, an organic light emitting layer, an electron transport layer, and a cathode, which are sequentially stacked, wherein the organic light emitting layer includes the organic compound of the present application.

Alternatively, the functional layer 300 includes an organic light emitting layer 330, and the organic light emitting layer 330 includes an organic compound provided herein. In one embodiment, the organic light emitting layer 330 may be composed of an organic compound provided herein; in another embodiment, the organic light emitting layer 330 may be composed of the compound provided herein together with other materials.

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

According to one embodiment, as shown in fig. 2, the electronic device is a first electronic device 400, and the first electronic device 400 includes the organic electroluminescent device. The first electronic device 400 may be, for example, a display device, a lighting device, an optical communication device, or other types of electronic devices, which may include, but are not limited to, a computer screen, a mobile phone screen, a television, electronic paper, an emergency light, an optical module, and the like.

In another embodiment, as shown in fig. 4, the electronic device is a second electronic device 500, and the second electronic device 500 includes the above-mentioned photoelectric conversion device. The second electronic device 500 may be, for example, a solar power generation apparatus, a light detector, a fingerprint recognition apparatus, a light module, a CCD camera, or other types of electronic devices.

Compounds of synthetic methods not mentioned in this application are all commercially available starting products.

Analytical detection of intermediates and compounds in this application uses an ICP-7700 mass spectrometer and an M5000 element analyzer.

The following will specifically explain the method for synthesizing the organic compound of the present application with reference to the synthesis examples.

Synthetic examples

The compounds of the invention were synthesized using the following method:

synthesis of intermediate a-1

1, 2-dibromo-3-chlorobenzene (80.0g, 298.7mmol), phenylboronic acid (36.5g, 298.7mmol), tetrakis (triphenylphosphine) palladium (6.9g, 6.0mmol), potassium carbonate (103.2g, 746.7mmol), tetrabutylammonium bromide (19.2g, 59.7mmol) were added to a flask, and a mixed solvent of toluene (600mL), ethanol (150mL) and water (150mL) was added, heated to 80 ℃ under nitrogen protection, and stirred at the temperature for 18 hours; cooling to room temperature, stopping stirring, washing the reaction solution with water, separating an organic phase, drying with anhydrous magnesium sulfate, and removing the solvent under reduced pressure to obtain a crude product; purification by column chromatography on silica gel using dichloromethane/n-heptane as the mobile phase gave the product intermediate a-1 as a white solid (42.0g, 53% yield).

The intermediate b-1 and the intermediate c-1 were synthesized by the method for synthesizing the intermediate a-1, using the reactant a in table 1 instead of 1, 2-dibromo-3-chlorobenzene:

TABLE 1

Synthesis of intermediate d-1

Adding 1-bromo-2-iodobenzene (50g, 176.73mmol), 3-chlorobenzeneboronic acid (27.64g, 176.73mmol), tetrakis (triphenylphosphine) palladium (1.02g, 0.88mmol), potassium carbonate (48.79g, 353.4mmol), tetrabutylammonium bromide (11.4g, 35.3mmol) into a flask, adding a mixed solvent of toluene (400mL), ethanol (100mL) and water (100mL), heating to 80 ℃ under nitrogen protection, keeping the temperature, and stirring for 12 hours; cooling to room temperature, stopping stirring, washing the reaction solution with water, separating an organic phase, drying with anhydrous magnesium sulfate, and removing the solvent under reduced pressure to obtain a crude product; purification by column chromatography on silica gel using dichloromethane/n-heptane as the mobile phase gave the product, intermediate d-1, as a white solid (29.3g, 62% yield).

Synthesis of intermediate a-2

Adding the intermediate a-1(42.0g, 157.9mmol) and tetrahydrofuran (300mL) into a flask, cooling to-78 ℃ under the protection of nitrogen, dropwise adding a tetrahydrofuran (2.5M) solution (95mL, 236.9mmol) of n-butyllithium under stirring, keeping the temperature and stirring for 1 hour after dropwise adding, dropwise adding a tetrahydrofuran (100mL) solution dissolved with adamantanone (19.0g, 126.3mmol) at-78 ℃, keeping the temperature and stirring for 24 hours after 1 hour after dropwise adding; a solution of hydrochloric acid (12M) (26.3mL, 315.8mmol) in water (100mL) was added to the reaction mixture, and the mixture was stirred for 1 hour; separating liquid, washing an organic phase to be neutral by using water, adding anhydrous magnesium sulfate for drying, and removing a solvent under reduced pressure to obtain a crude product; the crude product was purified by column chromatography on silica gel using ethyl acetate/n-heptane to give intermediate a-2(25.8g, 48% yield) as a white solid.

Using reactant a in table 2 instead of intermediate a-1, intermediate b-2, intermediate c-2 and intermediate d-2 were synthesized using the method for synthesizing intermediate a-2:

TABLE 2

Synthesis of intermediate a-3

Adding the intermediate a-2(25.8g, 76.3mmol) and glacial acetic acid (300mL) into a flask, slowly dropwise adding a concentrated sulfuric acid (98%) (0.8mL, 15.3mmol) solution in acetic acid (20mL) under the condition of nitrogen protection and normal temperature stirring, raising the temperature to 80 ℃ after dropwise addition, and stirring for 2 hours; cooling to room temperature, filtering the precipitated solid, leaching the filter cake with water and ethanol, and drying to obtain a crude product; the crude product was purified by column chromatography on silica gel using a dichloromethane/n-heptane system to give intermediate a-3(20.4g, yield 84%) as a white solid.

Using reactant a in table 3 instead of intermediate a-2, intermediate b-3, intermediate c-3 and intermediate d-3 were synthesized using the method for synthesizing intermediate a-3:

TABLE 3

Synthesis of intermediate a-4

Adding 1-bromo-9H-carbazole (15.65g, 63.7mmol), sodium hydrogen (2.3g, 95.4mmol) and N, N dimethylformamide (160mL) into a flask, stirring and dissolving under the protection of nitrogen at 20 ℃, starting to dropwise add N, N dimethylformamide (100mL) solution of an intermediate a-3(20.4g, 63.7mmol), and after the solution is completely dropwise added, the solution becomes clear, a large amount of white solid is generated after the solution turns yellow after 0.5H, sampling for 3H, detecting the conversion rate to be 86%, and finishing the reaction of the raw materials; adding 300ml of water into the reaction solution for washing, filtering to separate out solid, leaching with 100ml of ethanol, and pumping to obtain a crude product; the crude product was purified by column chromatography on silica gel using a dichloromethane/n-heptane system to give intermediate a-4(21.9g, yield 65%) as a white solid.

The intermediates shown in table 4 were synthesized by a method of synthesizing the intermediate a-4 using the reactant a in table 4 instead of 1-bromo-9H-carbazole and the reactant B instead of the intermediate a-3:

TABLE 4

Synthesis of intermediate a-5

Adding the intermediate a-4(17.13g, 32.3mmol), 2-nitrobromobenzene (7.1g, 35.5mmol), tetrakis (triphenylphosphine) palladium (0.7g, 0.6mmol), potassium carbonate (11.1g, 80.7mmol) and tetrabutylammonium bromide (2.1g, 6.5mmol) into a flask, adding a mixed solvent of toluene (80mL), ethanol (20mL) and water (20mL), heating to 80 ℃ under the protection of nitrogen, keeping the temperature and stirring for 24 hours; cooling to room temperature, stopping stirring, washing the reaction solution with water, separating an organic phase, drying with anhydrous magnesium sulfate, and removing the solvent under reduced pressure to obtain a crude product; purification by column chromatography on silica gel using dichloromethane/n-heptane as the mobile phase gave the product intermediate a-5 as a white solid (12.0g, 65% yield).

The intermediates shown in Table 5 were synthesized by the method of synthesizing intermediate a-5, using reactant A in Table 5 instead of intermediate a-4 and reactant B instead of 2-nitrobromobenzene:

TABLE 5

Synthesis of intermediate a-6

Adding the intermediate a-4(12.57g, 23.7mmol), 2-chloroaniline (3.2g, 24.9mmol), tris (dibenzylideneacetone) dipalladium (0.2g, 0.2mmol), 2-dicyclohexylphosphonium-2 ',4',6' -triisopropylbiphenyl (0.2g, 0.5mmol), sodium tert-butoxide (3.4g, 35.6mmol) and toluene (50mL) to a flask, and stirring at 98 ℃ under nitrogen protection for 4 hours under reflux; cooling to room temperature, washing the reaction solution with water, separating liquid, washing the organic phase with water, drying with anhydrous magnesium sulfate, and removing the solvent under reduced pressure to obtain a crude product; the crude product was purified by column chromatography on silica gel using a dichloromethane/n-heptane system to give intermediate a-6(7.66g, 56% yield) as a white solid.

The intermediates shown in table 6 were synthesized by a method of synthesizing the intermediate a-6 using the reactant a in table 6 instead of the intermediate a-4 and the reactant B instead of 2-chloroaniline:

TABLE 6

Synthesis of intermediate A to intermediate O

Adding the intermediate a-5(9.0g, 15.7mmol), triphenylphosphine (14.5g, 55.3mmol) and o-dichlorobenzene (100mL) into a flask, heating to 175 ℃ under the protection of nitrogen, stirring for 18 hours, cooling to room temperature, washing the reaction solution with water, separating the solution, washing the organic phase with water, drying with anhydrous magnesium sulfate, and removing the solvent at high temperature under reduced pressure to obtain a crude product; the crude product was purified by column chromatography on silica gel using ethyl acetate/n-heptane to give intermediate A as a white solid (7.56g, 89% yield).

Intermediates shown in table 7 were synthesized using the method for synthesizing intermediate a, using reactant a in table 7 instead of intermediate a-5:

TABLE 7

Synthesis of intermediate P to intermediate Y

Adding the intermediate a-6(10.79g, 18.7mmol), palladium acetate (2.1g, 9.4mmol), cesium carbonate (24.4g, 74.9mmol), tricyclohexylphosphine tetrafluoroborate (6.9g, 18.7mmol) and dimethylacetamide (70mL) into a flask, heating to 160 ℃ under the protection of nitrogen, stirring for 12 hours, cooling to room temperature, adding dichloromethane (300mL) into the reaction liquid, washing with a large amount of water, drying the obtained organic phase with anhydrous magnesium sulfate, and removing the solvent under reduced pressure to obtain a crude product; the crude product was purified by column chromatography on silica gel using a dichloromethane/n-heptane system to give intermediate P as a white solid (8.69g, yield 86%).

Intermediates shown in table 8 were synthesized using the method for synthesizing intermediate P, using reactant a in table 8 instead of intermediate a-6:

TABLE 8

Synthesis example 1: synthesis of Compound 1

Adding the intermediate A (7.5g, 13.87mmol), 4-bromobiphenyl (3.23g, 13.87mmol), cuprous iodide (0.8g, 4.0mmol), potassium carbonate (6.1g, 43.9mmol), 1, 10-phenanthroline (1.4g, 8.0mmol), 18-crown-6-ether (0.5g, 2.0mmol) and dimethylformamide (50mL) into a flask, heating to 145 ℃ under the protection of nitrogen, and stirring for 12 hours; cooling to room temperature, adding dichloromethane (100mL) and water into the reaction solution, separating, washing the organic phase with water, adding anhydrous magnesium sulfate, drying, and removing the solvent under reduced pressure to obtain a crude product; the crude product was purified by silica gel column chromatography using a methylene chloride/n-heptane system and then purified by recrystallization using a toluene/n-heptane system to give the product compound 1(5.1g, yield 53.1%) as a white solid.

Synthesis example 2: synthesis of Compound 131

Adding the intermediate Q (7.5g, 13.87mmol), 2-chloro-4, 6-diphenyl-1, 3, 5-triazine (3.71g, 13.87mmol), cuprous iodide (0.8g, 4.0mmol), potassium carbonate (6.1g, 43.9mmol), 1, 10-phenanthroline (1.4g, 8.0mmol), 18-crown-6-ether (0.5g, 2.0mmol) and dimethylformamide (50mL) into a flask, heating to 145 ℃ under the protection of nitrogen, and stirring for 12 hours; cooling to room temperature, adding dichloromethane (100mL) and water into the reaction solution, separating, washing the organic phase with water, adding anhydrous magnesium sulfate, drying, and removing the solvent under reduced pressure to obtain a crude product; the crude product was purified by column chromatography on silica gel using a methylene chloride/n-heptane system and then purified by recrystallization using a toluene/n-heptane system to give the product compound 131 as a white solid (6.21g, yield 58%).

¹H-NMR(CD₂Cl₂,400MHz):8.66(d,1H),8.37-8.31(m,4H),8.21-8.14(m,4H),7.90-7.89(m,1H),7.74(d,1H),7.58-7.55(m,3H),7.50-7.38(m,9H),7.28-7.24(m,2H),7.09(br,1H),6.95(d,1H),2.74-2.47(m,4H),2.01-1.97(m,2H),1.81(br,2H),1.62(br,2H),1.38-1.14(m,4H).

Synthetic example 3: synthesis of Compound 132

Adding the intermediate P (7.5g, 13.87mmol), 2-chloro-4, 6-diphenyl-1, 3, 5-triazine (3.71g, 13.87mmol), cuprous iodide (0.8g, 4.0mmol), potassium carbonate (6.1g, 43.9mmol), 1, 10-phenanthroline (1.4g, 8.0mmol), 18-crown-6-ether (0.5g, 2.0mmol) and dimethylformamide (50mL) into a flask, heating to 145 ℃ under the protection of nitrogen, and stirring for 12 hours; cooling to room temperature, adding dichloromethane (100mL) and water into the reaction solution, separating, washing the organic phase with water, adding anhydrous magnesium sulfate, drying, and removing the solvent under reduced pressure to obtain a crude product; the crude product was purified by column chromatography on silica gel using a methylene chloride/n-heptane system and then purified by recrystallization using a toluene/n-heptane system to give the product compound 132(5.67g, 53%) as a white solid.

¹H-NMR(CD₂Cl₂,400MHz):8.45-8.44(m,1H),8.34(d,1H),8.33-8.31(m,1H),8.27-8.17(m,5H),8.12(d,1H),7.88(d,1H),7.70(s,1H),7.54-7.26(m,13H),7.13(d,1H),7.10-7.15(m,2H),2.89-2.86(m,1H),2.70-2.68(m,1H),2.26(s,2H),2.08-2.05(m,2H),1.72-1.68(m,3H),1.58-1.54(m,2H),1.46-1.44(m,1H),1.18(s,2H).

Synthetic example 4: synthesis of Compound 136

Adding the intermediate B-1(7.5g, 13.87mmol), 2-chloro-4, 6-diphenyl-1, 3, 5-triazine (3.71g, 13.87mmol), cuprous iodide (0.8g, 4.0mmol), potassium carbonate (6.1g, 43.9mmol), 1, 10-phenanthroline (1.4g, 8.0mmol), 18-crown-6-ether (0.5g, 2.0mmol) and dimethylformamide (50mL) into a flask, heating to 145 ℃ under the protection of nitrogen, and stirring for 12 hours; cooling to room temperature, adding dichloromethane (100mL) and water into the reaction solution, separating, washing the organic phase with water, adding anhydrous magnesium sulfate, drying, and removing the solvent under reduced pressure to obtain a crude product; the crude product was purified by column chromatography on silica gel using a methylene chloride/n-heptane system and then purified by recrystallization using a toluene/n-heptane system to give the product compound 136(6.63g, 62%) as a white solid.

Compounds shown in table 9 were synthesized by the method of synthesis example 4 using reactant a in table 9 instead of intermediate B-1:

TABLE 9

Synthetic example 15: synthesis of Compound 20

Adding the intermediate K (8.65g, 16.0mmol), 2-chloro-4-phenylbenzo [ h ] quinazoline (4.9g, 16.8mmol), 4-dimethylaminopyridine (1.0g, 8.0mmol), cesium carbonate (5.2g, 16.0mmol) and dimethyl sulfoxide (80mL) into a round-bottomed flask, stirring and heating to 100 ℃ under the protection of nitrogen, and reacting for 10 hours; cooling to room temperature after the reaction is finished, filtering, leaching a filter cake by using water and ethanol, and drying to obtain a crude product; the crude product was purified by recrystallization from toluene to give compound 20 as a yellow solid (6.74g, 53% yield).

Compounds shown in table 10 were synthesized using the method of synthesis example 15, using reactant a in table 10 instead of intermediate K and reactant B instead of 2-chloro-4-phenylbenzo [ h ] quinazoline:

watch 10

Mass spectrometry analysis was performed on the above compounds, and the data are shown in table 11 below:

TABLE 11

Compound 1	m/z＝693.3(M+H)⁺	Compound 120	m/z＝899.3(M+H)⁺
				Compound 9	m/z＝848.4(M+H)⁺	Compound 20	m/z＝795.3(M+H)⁺
Compound 13	m/z＝733.3(M+H)⁺	Compound 33	m/z＝871.3(M+H)⁺
				Compound 24	m/z＝848.4(M+H)⁺	Compound 50	m/z＝885.3(M+H)⁺
Compound 40	m/z＝927.3(M+H)⁺	Compound 64	m/z＝863.3(M+H)⁺
				Compound 52	m/z＝793.3(M+H)⁺	Compound 69	m/z＝786.3(M+H)⁺
Compound 77	m/z＝833.3(M+H)⁺	Compound 89	m/z＝783.3(M+H)⁺
				Compound 84	m/z＝921.4(M+H)⁺	Compound 98	m/z＝927.3(M+H)⁺
Compound 95	m/z＝923.4(M+H)⁺	Compound 104	m/z＝895.4(M+H)⁺
				Compound 112	m/z＝908.4(M+H)⁺	Compound 108	m/z＝911.4(M+H)⁺
Compound 131	m/z＝772.3(M+H)⁺	Compound 132	m/z＝772.3(M+H)⁺
				Compound 136	m/z＝772.3(M+H)⁺

Preparation and evaluation of organic electroluminescent device

Device example 1: green organic electroluminescent device

An anode is formed of Indium Tin Oxide (ITO) on a substrate having a reflective layer formed thereon and has a thickness of

Cutting into 40mm (length) × 40mm (width) × 0.7mm (thickness), performing photolithography to prepare experimental substrate with cathode, anode and insulating layer patterns, and treating with ultraviolet ozone and N₂Plasma is used for surface treatment to increase the work function of an anode (experimental substrate), and an organic solvent is also used for cleaning the surface of the ITO substrate to remove impurities and oil stains on the surface of the ITO substrate.

The experimental substrate (anode) was vacuum evaporated with m-MTDATA (4,4' -tris (N-3-methylphenyl-N-phenylamino) triphenylamine) to a thickness of

And NPB is deposited on the hole injection layer to form a thickness of

The first hole transport layer of (1).

Vacuum evaporating TCBPA on the first hole transport layer to form a layer with a thickness of

The second hole transport layer of (1).

On the second hole transport layer, a composition of compound 1: GHp 1: ir (ppy)₃＝45％：45％：1Co-evaporating 0% of the mixed components to a thickness of

Green emitting layer (EML).

DBimiBphen (4, 7-diphenyl-2, 9-bis (4- (1-phenyl-1H-benzo [ d ]) is reacted]Imidazol-2-yl) phenyl) -1, 10-phenanthroline) and LiQ (8-hydroxyquinoline-lithium) in a weight ratio of 1:1 and vapor deposited to form

A thick Electron Transport Layer (ETL) formed by depositing Yb on the electron transport layer

And then magnesium (Mg) and silver (Ag) are mixed in a ratio of 1: 9 is vacuum-evaporated on the electron injection layer to a thickness of

The cathode of (1).

The thickness of the vapor deposition on the cathode is set to

Forming an organic capping layer (CPL) to complete the fabrication of the organic light emitting device, the structure of which is shown in fig. 1.

Device examples 2 to 9

An organic electroluminescent device was produced by the same method as that of device production example 1 except that the mixed components shown in table 13 were used instead of the mixed components in example 1 in forming the green light emitting layer.

Comparative example 1

An organic electroluminescent device was produced in the same manner as in device example 1, except that compound a was used in forming the green light-emitting layer.

Comparative example 2

An organic electroluminescent device was fabricated in the same manner as in device example 1, except that the compound B was used in forming the green light-emitting layer.

Comparative example 3

An organic electroluminescent device was fabricated in the same manner as in device example 1, except that compound C was used in forming the green light-emitting layer.

The material structures used in device example 1 and comparative examples 1-3 are shown in table 12 below:

TABLE 12

At 20mA/cm²Performance analysis was performed on the organic electroluminescent devices prepared in device examples 1 to 9 and comparative examples 1 to 3 under the conditions shown in table 13:

watch 13

Referring to the table, it can be seen that device examples 1-9 using the compound of the present invention as a green light emitting layer mixed host material reduced the driving voltage by at least 2.7%, improved the current efficiency (light emitting efficiency) by at least 10%, and improved the device lifetime by at least 14% as compared to comparative examples 1-3.

Therefore, when the novel compound disclosed by the invention is used for preparing a green organic electroluminescent device, the service life of the organic electroluminescent device can be effectively prolonged, and the luminous efficiency can be improved to a certain extent.

Device example 10: red organic electroluminescent device

On the substrate formed with the reflecting layerThe anode is formed of Indium Tin Oxide (ITO) with a thickness of

And NPB is deposited on the hole injection layer to form a thickness of

The first hole transport layer of (1).

Vacuum evaporating TPD on the first hole transport layer to form a layer with a thickness of

The second hole transport layer of (1).

On the second hole transport layer, a composition of compound 40: ir (piq)₂(acac) ═ 95%: 5% of the mixed components are co-evaporated to a thickness of

Red emitting layer (EML).

A thick Electron Transport Layer (ETL) formed by depositing Yb on the electron transport layerIs formed to a thickness of

The cathode of (1).

The thickness of the vapor deposition on the cathode is set to

Device examples 11 to 23

An organic electroluminescent device was produced by the same method as that of device production example 10, except that the mixed components shown in table 15 were used instead of the mixed components in example 10 in forming the red light emitting layer.

Comparative example 4

An organic electroluminescent device was fabricated in the same manner as in device example 10, except that BAlq was used instead of compound 40 in forming the red light-emitting layer, and the composition of the mixed components was as shown in table 15.

Comparative example 5

An organic electroluminescent device was fabricated in the same manner as in device example 10, except that the compound D was used instead of the compound 40 in forming the red light-emitting layer, and the composition of the mixture was as shown in table 15.

The material structures used in device examples 10-23 and comparative examples 4-5 are shown in table 14 below:

TABLE 14

At 20mA/cm²Performance analysis was performed on the organic electroluminescent devices prepared in device examples 10 to 23 and comparative examples 4 to 5 under the conditions of (1),the results are shown in Table 15:

watch 15

As can be seen from the table above, in device examples 10 to 23, when the compound of the present invention is used as a host material of a red light emitting layer, compared with comparative examples 4 and 5, the driving voltage of the device is greatly reduced by at least 0.17V, and the current efficiency is greatly improved by at least 4.5%; meanwhile, the service life is improved by at least 8.4 percent.

Therefore, when the novel compound disclosed by the invention is used for preparing a red organic electroluminescent device, the efficiency of the organic electroluminescent device can be effectively improved, and meanwhile, the service life is also improved.

The preferred embodiments of the present disclosure are described in detail with reference to the accompanying drawings, however, the present disclosure is not limited to the specific details of the above embodiments, and various simple modifications may be made to the technical solution of the present disclosure within the technical idea of the present disclosure, and these simple modifications all belong to the protection scope of the present disclosure.

It should be noted that, in the foregoing embodiments, various features described in the above embodiments may be combined in any suitable manner, and in order to avoid unnecessary repetition, various combinations that are possible in the present disclosure are not described again.

In addition, any combination of various embodiments of the present disclosure may be made, and the same should be considered as the disclosure of the present disclosure, as long as it does not depart from the spirit of the present disclosure.

Claims

1. An organic compound having a structure represented by formula I-1 and formula I-2:

wherein represents the point of attachment of formula I-1 fused to formula I-2;

n₁-n₅with n_tIs represented by R₁-R₅With R_tIs represented by t is a variable and represents an arbitrary integer of 1 to 5, n_tRepresents a substituent R_tThe number of (2); when t is 1 or 3, n_tSelected from 0, 1,2, 3, 4; when t is 2, n_tSelected from 0, 1,2, 3; when t is 4, n_tSelected from 0, 1, 2; when t is 5, n_tSelected from 0, 1,2, 3,4, 5, 6, 7, 8, 9, 10; when in usen_tWhen greater than 1, any two R_tThe same or different;

2. The organic compound according to claim 1, wherein the organic compound has a structure represented by any one of formulas 2-1 to 2-24:

3. the organic compound of claim 1 or 2, wherein L is₁And L₂Each independently selected from the group consisting of a single bond or the following groups:

wherein M is₁Selected from a single bond or

Q₁₄～Q₂₃each independently selected from N or C (F)₃) And Q is₁₄～Q₂₃At least one is selected from N; when Q is₁₄～Q₂₃Two or more of C (F)₃) When, two arbitrary F₃The same or different;

each E₁～E₆、F₁～F₃Are the same or different from each other and are each independently selected from: hydrogen, deuterium, fluorine, chlorine, bromine, cyano, heteroaryl with 3-20 carbon atoms, aryl with 6-20 carbon atoms, trialkylsilyl with 3-12 carbon atoms, arylsilyl with 8-12 carbon atoms, alkyl with 1-10 carbon atoms, haloalkyl with 1-10 carbon atoms, cycloalkyl with 3-10 carbon atoms, heterocycloalkyl with 2-10 carbon atoms, and alkoxy with 1-10 carbon atoms;

e₁～e₆with e_rIs represented by₁～E₆With E_rIs shown, r is a variable, tableRepresents an arbitrary integer of 1 to 6, e_rRepresents a substituent E_rThe number of (2); when r is selected from 1,2, 3, 6, e_rSelected from 1,2, 3 or 4; when r is selected from 4, e_rSelected from 1,2, 3,4, 5 or 6; when r is 5, e_rSelected from 1,2, 3,4, 5; when e is_rWhen greater than 1, any two of E_rThe same or different;

K₁selected from O, S, Se, N (E)₇)、C(E₈E₉)、Si(E₁₀E₁₁) (ii) a Wherein E is₇、E₈、E₉、E₁₀、E₁₁Are the same or different from each other and are each independently selected from: aryl having 6 to 20 carbon atoms, heteroaryl having 3 to 20 carbon atoms, alkyl having 1 to 10 carbon atoms, cycloalkyl having 3 to 10 carbon atoms, heterocycloalkyl having 2 to 10 carbon atoms, or E₈And E₉Are linked to each other to form, together with the atoms to which they are commonly attached, a 5-to 13-membered saturated or unsaturated ring, or E₁₀And E₁₁Are linked to each other to form, together with the atoms to which they are commonly attached, a 5-13 membered saturated or unsaturated ring;

K₂selected from the group consisting of a single bond, O, S, Se, N (E)₁₂)、C(E₁₃E₁₄)、Si(E₁₅E₁₆) (ii) a Wherein E is₁₂、E₁₃、E₁₄、E₁₅、E₁₆Are the same or different from each other and are each independently selected from: aryl having 6 to 20 carbon atoms, heteroaryl having 3 to 20 carbon atoms, alkyl having 1 to 10 carbon atoms, cycloalkyl having 3 to 10 carbon atoms, heterocycloalkyl having 2 to 10 carbon atoms, or E₁₃And E₁₄Are linked to each other to form, together with the atoms to which they are commonly attached, a 5-to 13-membered saturated or unsaturated ring, or E₁₅And E₁₆Are linked to form, together with the atoms to which they are commonly attached, a 5-13 membered saturated or unsaturated ring.

4. The organic compound according to any one of claims 1 to 3, wherein L is₁、L₂Each independently selected from single bond, substituted or unsubstituted carbon atom number is 6-12And a substituted or unsubstituted heteroarylene group having 3 to 15 carbon atoms.

5. The organic compound according to any one of claims 1 to 4, wherein L is₁、L₂Each independently selected from the group consisting of a single bond or the following groups:

6. the organic compound according to any one of claims 1 to 5, wherein L is₁、L₂Each independently selected from the group consisting of a single bond or the following groups:

7. the organic compound according to any one of claims 1 to 6, wherein L₁And L₂The substituents on (A) are selected from deuterium, fluorine, chlorine, bromine, cyano, phenyl, naphthyl, biphenyl, pyridyl, methyl, ethyl, isopropyl, tert-butyl, trimethylsilyl.

8. The organic compound according to any one of claims 1 to 7, wherein each R is₁、R₂、R₃、R₄、R₅The same or different from each other, and each independently selected from deuterium, cyano group, halogen group, trialkylsilyl group having 3 to 10 carbon atoms, unsubstituted alkyl group having 1 to 5 carbon atoms, or the group consisting of;

R₆independent of each otherIs selected from the group consisting of unsubstituted alkyl groups having 1 to 5 carbon atoms or the group consisting of:

wherein M is₂Selected from a single bond or

G₁selected from: hydrogen, deuterium, fluorine, chlorine, bromine, cyano, trialkylsilyl having 3 to 12 carbon atoms, arylsilyl having 8 to 12 carbon atoms, alkyl having 1 to 10 carbon atoms, haloalkyl having 1 to 10 carbon atoms, cycloalkane having 3 to 10 carbon atomsA group, a heterocycloalkyl group having 2 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms;

each G₇～G₁₁、F₄～F₆Are the same or different from each other and are each independently selected from: hydrogen, deuterium, fluorine, chlorine, bromine, cyano, aryl of 6 to 20 carbon atoms optionally substituted by deuterium, fluorine, chlorine, bromine, cyano, heteroaryl of 3 to 20 carbon atoms, trialkylsilyl of 3 to 12 carbon atoms, arylsilyl of 8 to 12 carbon atoms, alkyl of 1 to 10 carbon atoms, haloalkyl of 1 to 10 carbon atoms, cycloalkyl of 3 to 10 carbon atoms, heterocycloalkyl of 2 to 10 carbon atoms, alkoxy of 1 to 10 carbon atoms;

K₁selected from O, S, Se, N (G)₁₃)、C(G₁₄G₁₅)、Si(G₁₆G₁₇) (ii) a Wherein G is₁₃～G₁₇Are the same or different from each other and are each independently selected from: aryl group having 6 to 20 carbon atoms, carbonHeteroaryl having 3 to 20 carbon atoms, alkyl having 1 to 10 carbon atoms, cycloalkyl having 3 to 10 carbon atoms, heterocycloalkyl having 2 to 10 carbon atoms, or G₁₄And G₁₅Are linked to each other to form, together with the atoms to which they are commonly attached, a 5-13 membered saturated or unsaturated ring, or G₁₆And G₁₇Are linked to each other to form, together with the atoms to which they are commonly attached, a 5-13 membered saturated or unsaturated ring;

K₂selected from single bond, O, S, Se, N (G)₁₈)、C(G₁₉G₂₀)、Si(G₂₁G₂₂) (ii) a Wherein G is₁₈～G₂₂Each independently selected from: aryl group having 6 to 20 carbon atoms, heteroaryl group having 3 to 20 carbon atoms, alkyl group having 1 to 10 carbon atoms, cycloalkyl group having 3 to 10 carbon atoms, heterocycloalkyl group having 2 to 10 carbon atoms, or G₁₉And G₂₀Are linked to each other to form, together with the atoms to which they are commonly attached, a 5-13 membered saturated or unsaturated ring, or G₂₁And G₂₂Are linked to form, together with the atoms to which they are commonly attached, a 5-13 membered saturated or unsaturated ring.

9. The organic compound according to any one of claims 1 to 8, wherein R is₆Selected from alkyl groups having 1 to 5 carbon atoms or substituted or unsubstituted W selected from the group consisting of:

10. The organic compound according to any one of claims 1 to 9, wherein R is₆Each independently selected from the group consisting of alkyl groups having 1 to 5 carbon atoms or groups consisting of:

11. the organic compound according to any one of claims 1 to 10, wherein R is₆Selected from substituted or unsubstituted alkyl with 1-5 carbon atoms, substituted or unsubstituted aryl with 6-18 carbon atoms or substituted or unsubstituted heteroaryl with 5-15 carbon atoms.

12. The organic compound according to any one of claims 1 to 11, wherein each R is₁、R₂、R₃、R₄、R₅Identical or different from each other and each independently selected from deuterium, cyano, fluoro, methyl, ethyl, isopropyl, tert-butyl or the following substituted or unsubstituted groups: phenyl, naphthyl, biphenyl, terphenyl, phenanthryl, anthracyl, 9-spirobifluorenyl, 9-dimethylfluorenyl, pyridyl, carbazolyl, pyrimidinyl, pyridazinyl, triazinyl, quinolinyl, quinazolinyl, phenylpyridinyl, quinoxalinyl, pyrenyl, N-phenylcarbazolyl, dibenzofuranyl or dibenzothiophenyl,

13. The organic compound according to any one of claims 1 to 12, wherein the organic compound is selected from the group consisting of:

14. use of an organic compound according to any one of claims 1 to 13 in an organic electroluminescent device.

15. An organic electroluminescent device, wherein a light-emitting layer of the organic electroluminescent device comprises the organic compound according to any one of claims 1 to 13.

16. An electronic device comprising the organic electroluminescent element according to claim 15.