CN114716443A

CN114716443A - Organic compound, and organic electroluminescent device and electronic device using same

Info

Publication number: CN114716443A
Application number: CN202210503529.XA
Authority: CN
Inventors: 岳娜; 李应文; 金荣国
Original assignee: Shaanxi Lighte Optoelectronics Material Co Ltd
Current assignee: Shaanxi Lighte Optoelectronics Material Co Ltd
Priority date: 2022-05-09
Filing date: 2022-05-09
Publication date: 2022-07-08
Anticipated expiration: 2042-05-09
Also published as: CN114716443B

Abstract

The present application relates to an organic compound, and an organic electroluminescent device and an electronic apparatus using the same. The organic compound has a chemical structure as shown in formula 1 below. The organic compound is used in an organic electroluminescent device, and can improve the luminous efficiency and the service life of the device.

Description

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

Technical Field

The present invention relates to the field of organic material technology, and in particular, to an organic compound, and an organic electroluminescent device and an electronic apparatus using the same.

Background

The organic electroluminescent material is a thin film device prepared from an organic photoelectric functional material and capable of emitting light under the excitation of an electric field. At present, organic electroluminescent devices (OLEDs) are widely used in the fields of mobile phones, computers, lighting, and the like due to their advantages of high brightness, fast response, wide adaptability, and the like.

The organic electroluminescent device needs different organic functional materials besides an electrode material film layer, and the semiconducting property of the organic functional materials is that shifted pi bonds in material molecules, and pi bond or inverted pi bond orbitals form shifted atomic valence and conduction performance, and the overlapping of the pi bonds or the inverted pi bond orbitals respectively generates highest occupied orbitals (HOMO) and Lowest Unoccupied Molecular Orbitals (LUMO), so that charge transmission is generated through intermolecular hopping.

The continuous improvement of the performance of the organic electroluminescent device requires not only the innovation of the structure and the manufacturing process of the organic electroluminescent device but also the continuous research and innovation of the organic electro-optical functional material. At present, the performance of an organic electroluminescent device is improved by changing an organic functional material, and the capabilities of reducing the driving voltage of the device, improving the luminous efficiency of the device and prolonging the service life of the device are required.

Disclosure of Invention

An object of the present invention is to provide an organic compound that can be used in an organic electroluminescent device to improve the performance of the organic electroluminescent device, and an organic electroluminescent device and an electronic apparatus using the same.

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

wherein the group a has a structure as shown in formula 2 below:

het is a 6-18 membered electron-deficient nitrogen-containing heteroarylene group, and Het contains at least two nitrogen atoms;

L、L₁and L₂The same or different, and each independently selected from single bond, substituted or unsubstituted arylene group with 6-30 carbon atoms, substituted or unsubstituted heteroarylene group with 3-30 carbon atoms;

R₅selected from alkyl with 1-10 carbon atoms, halogenated alkyl with 1-10 carbon atoms, naphthenic base with 3-10 carbon atoms and substituted or unsubstituted aryl with 6-20 carbon atoms, wherein R is₅The substituent is selected from deuterium, cyano, halogen group, alkyl with 1-6 carbon atoms, halogenated alkyl with 1-6 carbon atoms, deuterated alkyl with 1-6 carbon atoms and aryl with 6-12 carbon atoms;

or R₅And L are linked to each other to form, together with the carbon atoms to which they are commonly linked, a 5-18 membered aliphatic ring or a 5-18 membered aromatic ring;

Ar₁and Ar₂The same or different from each other, and each independently selected from hydrogen, deuterium, substituted or unsubstituted aryl group having 6 to 30 carbon atoms, and substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms;

each R₁、R₂、R₃And R₄The same or different from each other, and each independently selected from deuterium, cyano, halogen group, alkyl group having 1 to 10 carbon atoms, haloalkyl group having 1 to 10 carbon atoms, deuterated alkyl group having 1 to 10 carbon atoms, cycloalkyl group having 3 to 10 carbon atoms, and aryl group having 6 to 20 carbon atoms; n is₁Represents R₁Number of (2), n₁Selected from 0, 1,2, 3 or 4; n is₂Represents R₂Number of (2), n₂Selected from 0, 1,2 or 3; n is₃Represents R₃Number of (2), n₃Selected from 0, 1 or 2; n is₄Represents R₄Number of (2), n₄Selected from 0, 1,2, 3 or 4;

L、L₁、L₂、Ar₁and Ar₂Wherein the substituents are the same or different and are each independently selected from the group consisting of deuterium, cyano, a halogen group, an alkyl group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, a deuterated alkyl group having 1 to 10 carbon atoms, and a ring having 3 to 10 carbon atomsAn alkyl group, an aryl group having 6 to 20 carbon atoms, a heteroaryl group having 3 to 20 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an alkylthio group having 1 to 10 carbon atoms, a trialkylsilyl group having 3 to 12 carbon atoms, an arylsilyl group having 6 to 18 carbon atoms, an aryloxy group having 6 to 20 carbon atoms, or an arylthio group having 6 to 20 carbon atoms; optionally, said Ar₁And Ar₂In (b), any two adjacent substituents are connected to each other to form a 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; preferably, the functional layer comprises an electron transport layer and a light emitting layer, and the electron transport layer and/or the light emitting layer comprise the organic compound.

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

Through the technical scheme, the organic compound has a carbazole fluorene type condensed mother ring, and can form a large rigid plane structure, so that the material has high thermal stability, film stability and carrier migration stability; in addition, the electron-deficient heteroaryl Het in the organic compound is connected to a 9' -position carbon atom of fluorene, and the molecular torsion is large, so that the evaporation temperature of molecules is reduced, the molecules are more stable, and the service life of a product can be effectively prolonged. The molecular structure contains the electron-deficient heteroaryl, so that the electron transmission capability of the material is greatly improved, and the organic material with high electron mobility is obtained; in addition, by adjusting the substituent groups on the heteroaryl group, the transport capabilities of electrons and holes can be further adjusted. The organic compound is used as the main material of an electron transport layer or a light emitting layer of an organic electroluminescent device, and can improve the light emitting efficiency and prolong the service life of the device.

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 an electronic device according to an embodiment of the present application.

Description of the reference numerals

100. Anode 200, cathode 300, functional layer 310, hole injection layer

321. Hole transport layer 322, electron blocking layer 330, light emitting layer 340, and electron transport layer

350. Electron injection layer 400 and 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.

A first aspect of the present application provides an organic compound having a chemical structure as shown in formula 1 below:

wherein the group a has a structure as shown in formula 2 below:

R₅selected from alkyl with 1-10 carbon atoms, halogenated alkyl with 1-10 carbon atoms, naphthenic base with 3-10 carbon atoms and substituted or unsubstituted aryl with 6-20 carbon atoms, wherein R is₅Wherein the substituent is selected from deuterium, cyano, halogen group, alkyl with 1-6 carbon atoms, halogenated alkyl with 1-6 carbon atoms, deuterated alkyl with 1-6 carbon atoms and aryl with 6-12 carbon atoms;

or, R₅And L are linked to each other to form a 5-to 18-membered aliphatic ring or a 5-to 18-membered aromatic ring together with the carbon atoms to which they are commonly attached (when R is₅And L are linked to each other to form a 5-to 18-membered aliphatic ring or a 5-to 18-membered aromatic ring, Het is linked to R₅And any position on the ring formed by L);

L、L₁、L₂、Ar₁and Ar₂Wherein the substituents are the same or different and are independently selected from deuterium, cyano, halogen, C1-10 alkyl, C1-10 haloalkyl, C1-10 deuterated alkyl, C3-10 cycloalkyl, C6-20 aryl, C3-E20 heteroaryl, alkoxy having 1 to 10 carbon atoms, alkylthio having 1 to 10 carbon atoms, trialkylsilyl having 3 to 12 carbon atoms, arylsilyl having 6 to 18 carbon atoms, aryloxy having 6 to 20 carbon atoms or arylthio having 6 to 20 carbon atoms; optionally, said Ar₁And Ar₂In (b), any two adjacent substituents are connected to each other to form a ring.

In the present application, the description "… … is" independently "and" … … is "independently" and "… … is" independently selected from "are used interchangeably, and should be understood broadly, which means that the specific items expressed between the same symbols in different groups do not affect each other, or that the specific items expressed between the same symbols in the same groups do not affect each other. For example, in the case of a liquid,

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 shows 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 mutually.

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 is deuterium, cyano, halogen, alkyl having 1 to 10 carbon atoms, haloalkyl having 1 to 10 carbon atoms, deuterated alkyl having 1 to 10 carbon atoms, cycloalkyl having 3 to 10 carbon atoms, aryl having 6 to 20 carbon atoms, heteroaryl having 3 to 20 carbon atoms, alkoxy having 1 to 10 carbon atoms, alkylthio having 1 to 10 carbon atoms, trialkylsilyl having 3 to 12 carbon atoms, arylsilyl having 6 to 18 carbon atoms, aryloxy having 6 to 20 carbon atoms, arylthio having 6 to 20 carbon atoms. The "substituted" functional group may be substituted with 1 or 2 or more substituents in the above Rc; 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. When two adjacent substituents Rc are attached to the same atom, the two substituents Rc may be independently present or screwed into a ring 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 Ar₁And is a substituted aryl group having 20 carbon atoms, then all carbon atoms of the aryl group and substituents thereon are 20 carbon atoms.

In this application, L, L₁、L₂、Ar₁、Ar₂And R₅The number of carbon atoms of (b) means all the number of carbon atoms. For example: l is a radical of an alcohol₁And is a substituted arylene group having 12 carbon atoms, the total number of carbon atoms in the arylene group and the substituents thereon is 12. For example: ar (Ar)₁Is composed of

The number of carbon atoms is 15; l is₁Is composed of

The number of carbon atoms is 12.

In the present 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 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 monocyclic aryl groups connected by carbon-carbon bond conjugation, a monocyclic aryl group and a fused ring aryl group connected by carbon-carbon bond conjugation, two or more fused ring aryl groups connected by carbon-carbon bond conjugation. Fused ring aryl refers to two or more rings in a ring system in which two carbon atoms are common to two adjoining rings, at least one of which is aromatic, the other rings can be, for example, cycloalkyl, cycloalkenylAnd an aryl group. Examples of aryl groups in the present application may include, but are not limited to, phenyl, naphthyl, anthracyl, phenanthryl, biphenyl, terphenyl, quaterphenyl, pentabiphenyl, benzo [9,10 ] or a mixture thereof]Phenanthryl, pyrenyl, benzofluoranthryl,

Perylene, fluorenyl, triphenylene, tetracenyl, triphenylene, spirobifluorenyl, and the like. In the present application, a fused aromatic ring refers to a polyaromatic ring in which two or more aromatic or heteroaromatic rings share a ring side, such as naphthalene, anthracene, phenanthrene, pyrene.

In the present application, the fluorenyl group may be substituted, and 2 substituents may be combined with each other to form a spiro structure. In the case where the above-mentioned fluorenyl group is substituted, the substituted fluorenyl group may be:

and the like, but is not limited thereto.

In this application, substituted aryl means that one or two or more hydrogen atoms in the aryl group are substituted with groups such as deuterium atoms, halogen groups, cyano groups, aryl groups, heteroaryl groups, trialkylsilyl groups, arylsilyl groups, alkyl groups, haloalkyl groups, cycloalkyl groups, alkoxy groups, alkylthio groups, 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 this application, terphenyl comprises

In the present application, examples of the aryl group as the substituent include, but are not limited to, phenyl, naphthyl, anthryl, phenanthryl, biphenyl, terphenyl, fluorenyl, dimethylfluorenyl, pyrenyl, perylenyl.

In the present application, the number of carbon atoms of the substituted or unsubstituted aryl group may be 6, 10, 12, 13, 14, 15, 16, 18, 19, 20, 24, 25, 29 or 30, and of course, the number of carbon atoms may be other numbers, which are not listed herein. In the present application, biphenyl is understood to mean phenyl-substituted aryl radicals and also unsubstituted aryl radicals.

In the present application, the arylene group is a polyvalent group, and in addition thereto, the above description about the aryl group can be applied.

Heteroaryl in this application refers to a monocyclic or polycyclic ring system containing 1,2, 3,4, 5, 6 or 7 heteroatoms independently selected from O, N, P, Si, Se, B and S in the ring, and wherein at least one ring system is aromatic. Heteroaryl groups contain a ring of 5 to 7 ring atoms per ring system and have one or more attachment points to the rest of the molecule. 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. Fused ring heteroaryl refers to two or more rings in a ring system in which two atoms are common to two adjoining rings, wherein at least one of the rings is aromatic, e.g., the other rings can be cycloalkyl, heterocyclyl, cycloalkenyl, aryl. Exemplary heteroaryl groups can include thienyl, furyl, pyrrolyl, imidazolyl, thiazolyl, oxazolyl, isothiazolyl, oxadiazolyl, triazolyl, pyridyl, bipyridyl, phenanthridinyl, pyrimidinyl, triazinyl, acridinyl, pyridazinyl, pyrazinyl, quinolyl, quinazolinyl, quinoxalinyl, phenoxazinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinyl, isoquinolyl, indolyl, carbazolyl, benzoxazolyl, benzimidazolyl, benzocarbazolyl, benzothienyl, benzothiophenyl, benzofuranyl, phenanthrolinyl, isoxazolyl, thiadiazolyl, benzothiazolyl, phenothiazinyl, silafluoxanyl, 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, substituted heteroaryl means that one or two or more hydrogen atoms in the heteroaryl group 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. 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. For example, a substituted heteroaryl group having 14 carbon atoms refers to a heteroaryl group and a substituent group having a total of 14 carbon atoms.

Examples of heteroaryl groups as substituents in the present application include, but are not limited to, dibenzothienyl, dibenzofuranyl, carbazolyl, N-phenylcarbazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, quinolinyl, isoquinolinyl, quinazolinyl, benzimidazolyl, indolyl, phenanthrolinyl.

In the present application, the number of carbon atoms of the substituted or unsubstituted heteroaryl group may be 3,4, 5, 7, 8, 9,10, 11, 12, 13, 14, 15, 16, 18, 20, 24, 25 or 30, and of course, the number of carbon atoms may be other numbers, which are not listed herein.

In the present application, electron-deficient nitrogen-containing (arylene) is taken to mean an aryl radical comprising at least one sp²Nitrogen atom hybridized (arylene) heteroaryl, wherein lone pair electrons in nitrogen atoms do not participate in conjugation, so that the overall electron density is low. The "6-to 18-membered electron-deficient nitrogen-containing heteroarylene group" is a group consisting of 6 to 18 ring atoms and containing sp²A heteroaromatic ring that hybridizes to a nitrogen atom; such as, but not limited to, pyrimidinyl, triazinyl, pyridazinyl, pyrazinyl, benzimidazolyl, quinazolinyl, quinoxalinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, benzimidazolyl, phenanthrolinyl, and the like.

In the present application, a heteroarylene group is a polyvalent group, and in addition thereto, the above description about a heteroaryl group can be applied.

As used herein, "alkyl" includes saturated straight or branched chain, monovalent or polyvalent hydrocarbon groups of 1 to 10 carbon atoms. In some embodiments, the alkyl group contains 1 to 10 carbon atoms; in other embodiments, the alkyl group contains 1 to 8 carbon atoms; in other embodiments, the alkyl group contains 1 to 6 carbon atoms; in other embodiments, the alkyl group contains 1 to 4 carbon atoms; in still other embodiments, the alkyl group contains 1 to 3 carbon atoms. Examples of the alkyl group having 1 to 4 carbon atoms as a substituent include, but are not limited to, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl and the like.

In the present application, hydrogen atoms, shown or not shown, each include various isotopes of hydrogen: hydrogen, deuterium and tritium.

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

In this application, "alkoxy" means an alkyl group attached to the rest of the molecule through an oxygen atom, wherein the alkyl group has the meaning as described herein. Examples of the alkoxy group as the substituent include, but are not limited to, methoxy group, ethoxy group, 1-propoxy group, 2-propoxy group, 1-butoxy group, 2-methyl-l-propoxy group, 2-butoxy group, 2-methyl-2-propoxy group, and the like.

In the present application, trialkylsilyl means

Wherein R is^G1、R^G2、R^G3Each independently an alkyl group, specific examples of trialkylsilyl groups include, but are not limited to, trimethylsilyl, triethylsilyl, t-butyldimethylsilyl, propyldimethylsilyl.

As used herein, "haloalkyl" means an alkyl group substituted with one or more halogen atoms, wherein the alkyl group has the meaning as described herein. In one embodiment, the haloalkyl group having 1 to 4 carbon atoms includes a fluoro-substituted alkyl group having 1 to 4 carbon atoms, examples of which include, but are not limited to, trifluoromethyl, difluoromethyl, 1-fluoro-2-chloroethyl, and the like.

The "ring" in the present application includes saturated rings, unsaturated rings; saturated rings, i.e., cycloalkyl, heterocycloalkyl; unsaturated rings, i.e., cycloalkenyl, heterocycloalkenyl, aryl, and heteroaryl.

In the present application, a ring system formed by n ring atoms is referred to as an "n-membered ring". For example, phenyl is a 6-membered aryl. The 5-to 10-membered aromatic ring is an aryl or heteroaryl group having 5 to 10 ring atoms; the 5-18 membered aliphatic ring means a cycloalkyl or cycloalkenyl group containing 5 to 18 ring atoms. The 5-18 membered aromatic ring is a ring system having 5-18 ring atoms, and the ring system includes aromatic moieties, such as but not limited to thiophene ring and benzene ring fluorene ring. As another example, a 5-18 membered aromatic ring is a ring system having 5 to 18 ring atoms and comprising an aromatic ring. For example, the fluorene ring is a 13-membered aromatic ring.

Is a substituted 14-membered aromatic ring.

In this application, the terms "optional" or "optionally" mean that the subsequently described event or circumstance may, but need not, occur, and that the description includes instances where the event or circumstance occurs or does not. For example, "optionally, any two adjacent substituents form a ring" means that two adjacent substituents may or may not form a ring, and this scheme includes a scenario in which two substituents are connected to each other to form a ring, and also includes a scenario in which two substituents are present independently of each other. For example, two adjacent substituents may be present in the form of a saturated or unsaturated ring, or may be present independently of each other. In the case where two adjacent substituents attached to the same atom form a ring, the ring formed is spiro attached to the rest of the molecule. In the case where two adjacent substituents attached to adjacent atoms form a ring, the ring formed is a fused connection to the rest of the molecule.

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

As another example, as shown in formula (f), the naphthyl group represented by formula (f) is connected to other positions of the molecule through two non-positional bonds through the bicyclic ring, and the meaning of the naphthyl group includes any of the possible connections shown in formulas (f-1) to (f-10).

In some embodiments herein, the Het group is selected from triazinylene, pyrimidylene, quinoxalylene, quinazolinylene, benzimidazolylene, phenanthrolinylene, benzoxazolinylene, phenanthrolinylene, phenanthreneimidazolyl, benzofuropyrimidylene, benzothienopyrimidylene.

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

wherein

Denotes the bond linking Het to L, the remaining two bonds

Are respectively connected with L₁And L₂。

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

wherein the content of the first and second substances,

represents the position at which Het is connected with L,

denotes Het and L₁The position of the connection is such that,

represents Het and L₂The location of the connection; in the formula

Absence, meaning that the position is connected to

In, L₂Is a single bond, Ar₂Is hydrogen.

In some embodiments of the present application, L, L₁And L₂The same or different from each other, and each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 18 carbon atoms, and a substituted or unsubstituted heteroarylene group having 5 to 18 carbon atoms.

Optionally, said L, L₁And L₂The substituents are independently selected from deuterium, cyano, fluorine, C1-5 alkyl, C1-5 haloalkyl, C1-5 deuteratedAn alkyl group, an aryl group having 6 to 12 carbon atoms, or a pyridyl group.

In some embodiments of the present application, L, L₁And L₂The same or different from each other, and each is 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 terphenylene group, a substituted or unsubstituted fluorenylene group, a substituted or unsubstituted anthrylene group, a substituted or unsubstituted phenanthrylene group, a substituted or unsubstituted dibenzothiophenylene group, a substituted or unsubstituted dibenzofuranylene group, and a substituted or unsubstituted carbazolyl group.

Optionally, said L, L₁And L₂Each substituent in (a) is independently selected from deuterium, fluoro, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, trifluoromethyl, trideuteromethyl, phenyl, naphthyl or pyridyl.

In some embodiments of the present application, L, L₁And L₂Identical or different from each other and each independently selected from a single bond, a substituted or unsubstituted group W selected from the following groups:

wherein the content of the first and second substances,

represents a chemical bond; the substituents on the group W are each independently selected from deuterium, fluoro, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, trifluoromethyl, trideuteromethyl, phenyl or naphthyl.

In some more specific embodiments of the present application, L, L₁And L₂Identical or different from each other, wherein L is selected from a single bond or the following groups:

alternatively, L₁And L₂Each independently selected from a single bond or the following groups:

in some embodiments of the present application, Ar₁Selected from substituted or unsubstituted aryl with 6-25 carbon atoms and substituted or unsubstituted heteroaryl with 12-18 carbon atoms;

Ar₂selected from hydrogen, deuterium, substituted or unsubstituted aryl group having 6 to 25 carbon atoms, and substituted or unsubstituted heteroaryl group having 12 to 18 carbon atoms.

Optionally, the Ar is₁And Ar₂Wherein the substituents are the same or different and are each independently selected from deuterium, halogen, cyano, haloalkyl having 1 to 4 carbon atoms, deuterated alkyl having 1 to 4 carbon atoms, cycloalkyl having 5 to 10 carbon atoms, aryl having 6 to 12 carbon atoms, heteroaryl having 5 to 12 carbon atoms, or trialkylsilyl having 3 to 8 carbon atoms; optionally, Ar₁And Ar₂In which any two adjacent substituents are bonded to each other to form a fluorene ring

Or a benzene ring

In some embodiments of the present application, Ar₁Selected from substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted terphenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted pyrenyl, substituted or unsubstituted perylenyl, substituted or unsubstituted anthracenylSubstituted phenanthryl, substituted or unsubstituted dibenzothienyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted spirobifluorenyl;

Ar₂selected from the group consisting of hydrogen, deuterium, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted terphenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted pyrenyl, substituted or unsubstituted perylenyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted dibenzothienyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted carbazolyl, and substituted or unsubstituted spirobifluorenyl.

Optionally, the Ar is₁And Ar₂Wherein the substituents are the same or different and are each independently selected from deuterium, fluoro, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, trifluoromethyl, trideuteromethyl, pyridyl, phenyl, naphthyl, dibenzothienyl, dibenzofuranyl, or carbazolyl; optionally, Ar₁And Ar₂In (b), any two adjacent substituents are connected to each other to form a fluorene ring or a benzene ring.

In this application, Ar₁、Ar₂Wherein any two adjacent substituents form a fluorene ring means Ar₁Any two adjacent substituents of (a) may form a fluorene ring, and Ar₂Any two adjacent substituents of (a) may form a fluorene ring, for example when Ar₁Is composed of

When having the structure shown, Ar₁The substituents of (a) are two phenyl groups on the fluorenyl group, and the two phenyl groups are not connected to form a ring; in addition, the substituents may be linked to form a ring

The structure shown, the ring structure formed at this time is the fluorene ring.

In some embodiments of the present application, Ar₁And Ar₂Identical or different, Ar₁Selected from substituted or unsubstituted groups Y, Ar₂Selected from hydrogen, deuterium, a substituted or unsubstituted group Y, wherein the unsubstituted group Y is selected from the group consisting of:

represents a chemical bond; when said group Y is substituted with one or more substituents, each of said substituents is independently selected from deuterium, fluoro, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, trifluoromethyl, trideuteromethyl, pyridyl, phenyl, naphthyl, dibenzothienyl, dibenzofuranyl, or carbazolyl.

In some more specific embodiments of the present application, Ar₁Selected from the group consisting of Ar₂Selected from hydrogen, deuterium or the group consisting of:

in some embodiments of the present application, the first and second electrodes are,

selected from the following structures:

in some more specific embodiments of the present application,

selected from the following structures:

in one embodiment of the present application, each R₁、R₂、R₃And R₄Identical or different from each other and are each independently selected from deuterium, fluoro, cyano, trimethylsilyl, trideuteromethyl, trifluoromethyl, cyclopentyl, cyclohexyl, methyl, ethyl, isopropyl, tert-butyl or phenyl.

In one embodiment of the present application, R₅Selected from methyl, ethyl, n-propyl, isopropyl, tert-butyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted terphenyl, substituted or unsubstituted phenanthryl, and substituted or unsubstituted fluorenyl, wherein R is₅Each substituent in (a) is independently selected from deuterium, fluoro, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, trifluoromethyl, trideuteromethyl or phenyl;

or, R₅And L are linked to each other to form, together with the carbon atom to which they are commonly attached, a cyclopentane, cyclohexane or fluorene ring, in which case,

is connected to R₅And L is on the spiro ring formed by the compound. For example, when R is₅And L are connected with each other to form a loopWhen constructed as cyclohexane, the group A is attached in a manner

In some embodiments herein, the organic compound is selected from the group consisting of the compounds of claim 12.

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 the organic compound provided in the first aspect of the present application.

In a specific embodiment, the functional layer comprises an electron transport layer comprising an organic compound provided herein. The electron transport layer may be composed of the organic compound provided herein, or may be composed of the organic compound provided herein and other materials, and the electron transport layer may be one layer or two or more layers.

In a specific embodiment, the functional layer comprises a light-emitting layer comprising an organic compound provided herein. The host material in 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.

As shown in fig. 1, the organic electroluminescent device may include an anode 100, a hole injection layer 310, a hole transport layer 321, an electron blocking layer 322, a light emitting layer 330 as an energy conversion layer, an electron transport layer 340, an electron injection layer 350, 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 SnO₂: sb; or conductive polymers such as poly (3-methylthiophene), poly[3,4- (ethylene-1, 2-dioxy) thiophene](PEDT), polypyrrole and polyaniline, but are not limited thereto. Preferably, the electronic component includes a transparent electrode having Indium Tin Oxide (ITO) as an anode.

Alternatively, the hole transport layer 321 may include one or more hole transport materials, and the hole transport material may be selected from carbazole multimer, carbazole-linked triarylamine-based compound, or other types of compounds, which are not specifically limited herein. For example, the hole transport layer 321 is composed of a compound NPB.

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

Optionally, an electron blocking layer 322 is further provided between the hole transport layer 321 and the light emitting layer 330 to block the transport of electrons to the hole transport layer 321 side, improve the recombination rate of electrons and holes in the light emitting layer 330, and protect the hole transport layer 321 from the impact of electrons. The material of the electron blocking layer 322 may be carbazole multimer, carbazole-linked triarylamine-based compounds, or other feasible structures. For example, electron blocking layer 322 is EB-01.

The light emitting layer 330 may be composed of a single light emitting material, or may include a host material and a dopant material (also referred to as a guest material). Alternatively, the light emitting layer 330 is composed of a host material and a dopant material, and holes injected into the light emitting layer 330 and electrons injected into the light emitting layer 330 may be combined at the light emitting layer 330 to form excitons, which transfer energy to the host material, which transfer energy to the dopant material, thereby enabling the dopant material to emit light.

The host material of the 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. In one embodiment of the present application, the light emitting layer host material comprises a compound described herein.

The doping material of the 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, and the present application is not particularly limited thereto. The dopant may be selected from a red phosphorescent dopant, a green phosphorescent dopant, or a blue dopant. Specific examples of the blue light dopant include but are not limited to,

in another embodiment of the present application, the light emitting layer 330 is composed of BH-01 and BD-01.

Alternatively, 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, which may be selected from, but not limited to, organic compounds, benzimidazole derivatives, oxadiazole derivatives, quinoxaline derivatives, or other electron transport materials of the present application. In one embodiment of the present application, the electron transport layer 340 is composed of the organic compound provided herein and LiQ.

In the present application, the cathode 200 comprises a cathode material, which is a material with a small work function that facilitates electron injection into the functional layer. Specific examples of the cathode material include, 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, an electron injection layer 350 is 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 contains LiQ.

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

According to one embodiment, as shown in fig. 2, the electronic device is an electronic device 400, and the electronic device 400 includes the 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, 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.

Synthesis example:

in the synthesis examples described below, all temperatures are in degrees celsius unless otherwise stated. Some of the reagents were purchased from commercial suppliers such as Aldrich Chemical Company, Arco Chemical Company and Alfa Chemical Company, some of the intermediates that could not be purchased directly were prepared by simple reactions from commercially available starting materials, and all of the compounds of the synthetic methods not mentioned in this application were commercially available starting products.

Unless otherwise stated, none was used without further purification. The other conventional reagents were purchased from Shantou Wen Long chemical reagent factory, Guangdong Guanghua chemical reagent factory, Guangzhou chemical reagent factory, Tianjin Haojian Yunyu chemical Co., Ltd, Tianjin Shucheng chemical reagent factory, Wuhan Xin Huayuan science and technology development Co., Ltd, Qingdao Tenglong chemical reagent Co., Ltd, and Qingdao Kaolingyi factory. During purification, the chromatographic column is a silica gel column, and the silica gel (100-200 meshes) is purchased from Qingdao oceanic plants.

In each synthesis example, the conditions for measuring low resolution Mass Spectrometry (MS) data were: agilent 6120 four-stage rod HPLC-M (column model: Zorbax SB-C18, 2.1X 30mm,3.5 μ M, 6min, flow rate 0.6 mL/min. mobile phase: ratio of 5% -95% (acetonitrile containing 0.1% formic acid) in (water containing 0.1% formic acid)), using electrospray ionization (ESI), at 210nm/254nm, with UV detection.

Hydrogen nuclear magnetic resonance spectroscopy: bruker 400MHz NMR instrument in CDCl at room temperature₃Or CD₂Cl₂As solvent (in ppm) TMS (0ppm) was usedIs a reference standard.

1. Preparation of intermediates

9H-fluoren-9-one (307g, 1703.57mmol), tetradecyltrimethylammonium chloride (74.60g, 255.54mmol) and tetrabutylammonium bromide aqueous solution (4.5L,4258.93mmol) were added to a three-neck flask, stirred and heated to 75 ℃, and then potassium bromate (312.95g,1873.93mmol) was added to the flask three times, and the reaction was incubated for 4H after the addition. After the reaction was completed, the temperature was lowered to room temperature, and 20% (mass fraction) of an aqueous sodium sulfite solution (bromine-removing solution) was added thereto to wash, filter, wash the cake with water and dry it to obtain IM A-1-1(281.79g, yield 63.84%) as a yellow solid.

Under the protection of nitrogen, adding IM A-1-1(281.75g,1096.3mmol) and tetrahydrofuran (1690mL) into a three-mouth reaction bottle, starting stirring, cooling the system to-78 ℃ after uniform stirring, starting dropwise adding n-butyl lithium (43mL,978.68mmol) after the temperature is stable, preserving heat at-78 ℃ for reaction for 2h after dropwise adding, then dropwise adding a tetrahydrofuran (410mL) solution of bromobenzene (204.88g,1304.9mmol) into the system, continuing preserving heat at-78 ℃ for reaction for 1h after dropwise adding, naturally heating to 25 ℃ and stirring for 12 h. The reaction was then poured into water (600mL) and stirred for 10min, followed by extraction with dichloromethane (500mL) 2 times, the organic phases were combined, dried over anhydrous magnesium sulfate, the organic phase was passed through a silica gel funnel, and the filtrate was concentrated to give IM A-2-1(219.58g, 59.88% yield).

IM A-2-X was synthesized in the same manner as IM A-2-1, except that bromobenzene was replaced by raw material 1 in the following Table, and IM A-2-X was synthesized and its yield are shown in Table 1 below.

TABLE 1

IM A-2-1(219.35g,650.47mmol) and toluene (1755mL) are added into a three-neck flask, stirring is carried out at room temperature, HBr (225mL,1951.4mmol) with the mass concentration of 48% is added, stirring is carried out to increase the temperature to 60 ℃, reaction is stopped after 48h of reaction, cooling is carried out to room temperature, water washing and toluene extraction are carried out, an organic phase is dried by anhydrous magnesium sulfate and then concentrated under reduced pressure, and the obtained crude product is recrystallized by normal hexane to obtain a white solid IM A-3-1(176.98g, yield 68.12%).

The intermediates IM A-3-X were synthesized in the same manner as IM A-3-1 except that IM A-2-1 was replaced with IM A-2-X, and the synthesis of IM A-3-X and the yields thereof are shown in Table 2.

TABLE 2

A three-necked flask equipped with a mechanical stirrer, a thermometer and a dropping funnel was purged with nitrogen (0.100L/min) for 15min, IM A-3-1(176.8g, 441.88mmol) and tetrahydrofuran (1415mL) were added thereto, liquid nitrogen was cooled to-80 ℃ to-90 ℃, a tetrahydrofuran solution of t-butyllithium (t-BuLi) (64.43mL,663mmol) was added dropwise, stirring was carried out while maintaining the temperature for 2h after completion of the addition, triisopropyl borate (124.66mL,662.82mmol) was further added thereto, the reaction mixture was gradually warmed to room temperature and stirred for 3h, an aqueous hydrochloric acid solution (500mL) was added to the reaction mixture, and then the reaction was stirred at room temperature for 1.5 h. The reaction was complete, the precipitate was filtered, and the filter cake was washed with water and ether and dried under vacuum to give IM A-4-1(107.33g, yield 66.54%).

Each intermediate IM A-4-X was synthesized in the same manner as IM A-4-1, except that each IM A-3-X was used in place of IM A-3-1, and the synthesis of IM A-4-X and the yield thereof are shown in Table 3.

TABLE 3

A three-necked flask equipped with a mechanical stirrer, a thermometer and a bulb-shaped condenser was purged with nitrogen (0.100L/min) for 15min, and IM A-4-1(107.0g,293.13mmol), 2-iodo-nitrobenzene (73.0g,293.13mmol), tetrahydrofuran (645mL) and H were added₂O (215 mL). The mixture was stirred at elevated temperature until clear and refluxed, tetrabutylammonium bromide (1.89g, 5.86mmol), tetrakis (triphenylphosphine) palladium (3.39g,2.93mmol) and potassium carbonate (60.68g,439.7mmol) were added, the mixture was refluxed for 15 hours, and after the reaction was completed, the mixture was cooled to room temperature. Dichloromethane was added for extraction, water washing was performed to neutrality, the organic phase was collected, the organic phase was dried over anhydrous magnesium sulfate, the filtrate was concentrated by distillation under reduced pressure after filtration to give a crude product, which was purified by silica gel column chromatography to give IM a-5-1(88.59g, yield 68.33%).

Each intermediate IM A-5-X was synthesized in the same manner as IM A-5-1, except that each IM A-4-X was used in place of IM A-4-1, and IM A-5-X was synthesized with the yields shown in Table 4.

TABLE 4

A three-necked flask equipped with a mechanical stirrer, a thermometer and a bulb-shaped condenser was purged with nitrogen (0.100L/min) for 15min, and IM A-5-1(88.50g,200.09mmol), triphenylphosphine (3.15g,12.01mmol) and o-dichlorobenzene (885mL) were added thereto. Starting stirring, heating to 180 ℃ for reaction for 16h, and cooling to room temperature after the reaction is finished. Washing the reaction solution with water, drying the separated organic phase by using anhydrous magnesium sulfate, filtering, and distilling the filtrate under reduced pressure to remove the solvent to obtain a crude product; the crude product was purified by silica gel column chromatography to give IM A-6-1(50.81g, yield 61.89%).

Each intermediate IM A-6-X was synthesized in the same manner as IM A-6-1, except that each IM A-5-X was used in place of IM A-5-1, and the synthesized IM A-6-X and the yield thereof were as shown in Table 5.

TABLE 5

Introducing nitrogen (0.100L/min) into a three-neck flask provided with a mechanical stirring thermometer and a spherical condenser for replacement for 15min, adding IM A-6-1(50.53g,123.15mmol), o-chlorobromobenzene (24.76g,129.31mmol), tris (dibenzylideneacetone) dipalladium (1.13g,1.23mmol), S-Phos (1.00g,2.46mmol), sodium tert-butoxide (17.75g,184.73mmol) and toluene (405mL), heating the reaction mixture to 105-110 ℃, stirring for reaction for 2h, and cooling to room temperature after the reaction is finished. Extraction, washing of the combined organic phases with water, drying of the organic phases over anhydrous magnesium sulphate, filtration, removal of the solvent by distillation under reduced pressure and purification of the crude product by recrystallisation from a dichloromethane/n-heptane system gave IM A-7-1(45.75g, 71.33% yield).

Each intermediate IM A-7-X was synthesized in the same manner as IM A-7-1, except that each IM A-6-X was used in place of IM A-6-1, and the synthesized IM A-7-X and the yield thereof were as shown in Table 6.

TABLE 6

A three-necked flask equipped with a mechanical stirrer, a thermometer and a bulb-shaped condenser was purged with nitrogen (0.100L/min) for 15min, and IM A-7-1(45.58g, 87.51mmol), palladium acetate (1.96g, 8.75mmol), tricyclohexylphosphonium fluoroborate (6.44g,17.50mmol), cesium carbonate (42.77g,131.27mmol) and N, N-dimethylacetamide (274mL) were added thereto. Starting stirring, heating and refluxing for reaction for 2h, and cooling to room temperature after the reaction is finished. Extracting the reaction liquid with chloroform, drying the combined organic phase with anhydrous magnesium sulfate, filtering, and distilling the filtrate under reduced pressure to remove the solvent to obtain a crude product; the crude product was purified by silica gel column chromatography to give IM A-8-1(27.90g, 65.82% yield).

Each intermediate IM A-8-X was synthesized in the same manner as IM A-8-1, except that each IM A-7-X was used in place of IM A-7-1, and the synthesis and yield of IM A-8-X are shown in Table 7.

TABLE 7

A three-necked flask equipped with a mechanical stirrer, a thermometer and a spherical condenser was purged with nitrogen (0.100L/min) for 15min, and IM A-8-1(42.27g, 87.51mmol), pinacol diboron diboride (33.34g,131.26mmol), potassium acetate (12.88g,131.26mmol), x-Phos (0.48g,1.75mmol), tris (dibenzylideneacetone) dipalladium (0.50g,0.87mmol) and 1, 4-dioxane (250mL) were added thereto, followed by stirring with heating and refluxing for 2h, and after completion of the reaction, the mixture was cooled to room temperature. Extracting the reaction liquid with chloroform, drying the combined organic phase with anhydrous magnesium sulfate, filtering, and distilling the filtrate under reduced pressure to remove the solvent to obtain a crude product; the crude product was purified by silica gel column chromatography to give IM A-9-1(27.90g, yield 65.82%).

Each intermediate IM A-9-X was synthesized in the same manner as IM A-9-1, except that each IM A-8-X was used in place of IM A-8-1, and the synthesis of IM A-9-X and the yield thereof were as shown in Table 8.

TABLE 8

Introducing nitrogen (0.100L/min) into a three-necked flask provided with a mechanical stirring device, a thermometer and a spherical condenser for replacement for 15min, adding IM A-9-1(38.50g,72.44mmol), p-chloroiodobenzene (18.14g,76.07mmol), palladium acetate (0.33g, 1.45mmol), potassium carbonate (15.0g, 108.66mmol), S-Phos (1.19g,2.90mmol), toluene (234mL), anhydrous ethanol (77mL) and deionized water (77 mL); stirring and heating are started, reflux reaction is carried out for 4 hours when the temperature rises to 70-80 ℃, and cooling is carried out to room temperature after the reaction is finished. Extraction, water washing, combining the organic phases, drying over anhydrous magnesium sulphate, filtering to remove the solvent and purification by recrystallisation of the crude product using the dichloromethane/petroleum ether system gave solid IM A-10-1(25.79g, 68.98% yield).

IM A-10-X was synthesized in the same manner as IM A-10-1, except that IM A-9-X was used in place of IM A-9-1, and p-chloroiodobenzene was used in place of raw material 2, and the synthesized IM A-10-X and the yield thereof were as shown in Table 9.

TABLE 9

A three-necked flask equipped with a mechanical stirrer, a thermometer and a spherical condenser was purged with nitrogen (0.100L/min) for 15min, followed by addition of IM A-10-1(26.01g,50.40mmol), pinacol diboron diborate (19.12g,75.60mmol), potassium acetate (7.42g,75.6mmol), x-Phos (0.48g,1.01mmol), tris (dibenzylideneacetone) dipalladium (0.46g,0.50mmol) and 1, 4-dioxane (208mL), heating to reflux for 3h, and after completion of the reaction, cooling to room temperature. The reaction solution was extracted, the organic phase was dried over anhydrous magnesium sulfate, the filtrate was filtered, the solvent was removed under reduced pressure, and the crude product was purified by recrystallization using a toluene/n-heptane system, and filtered to obtain IM A-11-1(19.66g, yield 64.22%).

IM A-11-X was synthesized in the same manner as IM A-11-1, except that IM A-10-X was used in place of IM A-10-1, and the synthesized IM A-11-X and the yield thereof were as shown in Table 10.

Watch 10

Introducing nitrogen (0.100L/min) into a three-neck flask provided with a mechanical stirring device, a thermometer and a spherical condenser for 15min, adding IM A-9-1(19.58g, 36.84mmol), cyanuric chloride (8.15g, 44.21mmol), palladium acetate (0.083g, 0.37mmol), potassium carbonate (7.63g, 55.26mmol), s-phos (0.30g, 0.74mmol), toluene (160mL), absolute ethanol (40mL) and deionized water (40 mL); stirring and heating are started, reflux reaction is carried out for 4 hours when the temperature rises to 70-80 ℃, and cooling is carried out to room temperature after the reaction is finished. Extraction, water washing, combined organic phases, drying over anhydrous magnesium sulfate, filtration to remove solvent, and purification of the crude product by recrystallization using a dichloromethane/n-heptane system gave solid IM A-12-1(13.66g, 67.0% yield).

IM A-12-X was synthesized in the same manner as IM A-12-1, except that raw material 3 was used in place of IM A-9-1, and the synthesized IM A-12-X and the yield thereof were as shown in Table 11.

TABLE 11

A three-necked flask equipped with a mechanical stirrer, a thermometer and a spherical condenser was purged with nitrogen (0.100L/min) for 15min, followed by addition of IM A-12-1(13.55g,24.48mmol), biphenyl-4-borate (6.30g,31.82mmol), potassium carbonate (5.07g,36.72mmol), TBAB (0.16g,0.49mmol), palladium tetrakistriphenylphosphine (0.28g,0.25mmol), THF (84mL) and deionized water (28mL), heating to reflux for 5h, and after completion of the reaction, cooling to room temperature. The reaction solution was extracted, the organic phase was dried over anhydrous magnesium sulfate, filtered, and the filtrate was freed of the solvent under reduced pressure, purified by recrystallization of the crude product using DCM/n-heptane system, and filtered to give IM A-13-1(10.36g, yield 63.05%).

Each intermediate IM A-13-X was synthesized in the same manner as IM A-13-1, except that each IM A-12-X was used in place of IM A-12-1 and that 4-boratabiphenyl was used as the starting material 4, and the synthesized IM A-13-X and the yield thereof were as shown in Table 12.

TABLE 12

2. Preparation of the Compounds

Introducing nitrogen (0.100L/min) into a three-neck flask provided with a mechanical stirrer, a thermometer and a spherical condenser for replacement for 15min, sequentially adding IM A-13-1(10.32g,15.24mmol), 4-diphenyl borate (3.92g,19.81mmol), potassium carbonate (3.15g,22.86mmol), TBAB (0.25g,0.79mmol), palladium tetrakistriphenylphosphine (0.35g,0.31mmol), toluene (60ml), ethanol (20ml) and water (20ml), heating to 75-80 ℃, refluxing for 4h, and cooling to room temperature after the reaction is finished. Extracting the reaction solution, drying the organic phase with anhydrous magnesium sulfate, filtering, removing the solvent from the filtrate under reduced pressure, and usingThe crude product was purified by recrystallization from toluene/n-heptane and filtered to yield compound 17(7.36g, 61.23% yield). Mass spectrum: 789.3[ M + H ] M/z]⁺。

Compound X was synthesized in the same manner as in Compound 17 except that IM A-13-1 was replaced with raw material 5 and biphenyl-4-borate was replaced with raw material 6, and the synthesized compound X and the yield and mass spectrum results thereof are shown in Table 13.

Watch 13

Nuclear magnetic data

Device embodiment

Example 1: blue organic electroluminescent device

The anode pretreatment is carried out by the following processes: the thickness is sequentially

The ITO/Ag/ITO substrate is subjected to surface treatment by using ultraviolet ozone and O2: N2 plasma to increaseAnd (3) cleaning the surface of the ITO substrate by using an organic solvent to remove impurities and oil stains on the surface of the ITO substrate.

HAT-CN was vacuum-deposited on an experimental substrate (anode) to a thickness of

A Hole Injection Layer (HIL).

Vacuum evaporating NPB on the hole injection layer to form a thickness of

And EB-01 is vacuum-evaporated on the hole transport layer to form a layer having a thickness of

Electron Blocking Layer (EBL).

On the electron blocking layer, BH-01: BD-01 as a 98%: co-evaporation at 2% evaporation rate ratio to form a film with a thickness of

Blue organic light emitting layer (EML).

Compound 17 and LiQ were mixed at a weight ratio of 1:1 and vapor-deposited to form

A thick Electron Transport Layer (ETL), and depositing LiQ on the electron transport layer to form a layer with a thickness of

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

The cathode of (2).

Evaporating CP-01 on the cathode to form a film with a thickness of

Thereby completing the fabrication of the organic electroluminescent device.

Examples 2 to 28

Except that in the formation of the Electron Transport Layer (ETL), the remaining compounds shown in the column of compound X in table 14 were used instead of compound 17 in example 1, and an organic electroluminescent device was fabricated by the same method as in example 1.

Comparative examples 1 to 4

An organic electroluminescent device was produced in the same manner as in example 1, except that compound A, B, C, D was used instead of compound 17 in example 1 in the formation of the Electron Transport Layer (ETL).

In examples 1 to 28 and comparative examples 1 to 4, the structural formulae of the respective main materials used are as follows.

For the organic electroluminescent device prepared as above, at 10mA/cm²The IVL performance of the device was analyzed at 20mA/cm²The life of T95 was tested under the conditions shown in Table 14 below.

TABLE 14

As can be seen from table 14 above, compared with comparative examples 1 to 4 using known compounds a to D, the organic electroluminescent device prepared using the organic compound provided in the present application has a luminous efficiency at least improved by 13.8% and a device lifetime at least improved by 18.7%. Therefore, when the organic compound provided by the application is used as an electron transport layer, the luminous efficiency and the service life of an organic electroluminescent device can be obviously improved.

Claims

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

wherein the group a has a structure as shown in formula 2 below:

or, R₅And L are linked to each other to form, together with the carbon atoms to which they are commonly linked, a 5-to 18-membered aliphatic ring or a 5-to 18-membered aromatic ring;

Ar₁and Ar₂The same or different from each other, and each independently selected from hydrogen, deuterium, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, and a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms;

each R₁、R₂、R₃And R₄Identical to or different from each other, and are each independently selected from deuterium, cyano, halogen radicals, having 1 to E carbon atomsAn alkyl group having 10 carbon atoms, a halogenated alkyl group having 1 to 10 carbon atoms, a deuterated alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, and an aryl group having 6 to 20 carbon atoms; n is₁Represents R₁Number of (2), n₁Selected from 0, 1,2, 3 or 4; n is a radical of an alkyl radical₂Represents R₂Number of (2), n₂Selected from 0, 1,2 or 3; n is₃Represents R₃Number of (2), n₃Selected from 0, 1 or 2; n is₄Represents R₄Number of (2), n₄Selected from 0, 1,2, 3 or 4;

L、L₁、L₂、Ar₁and Ar₂Wherein the substituents are the same or different and are each independently selected from deuterium, cyano, halogen, alkyl having 1 to 10 carbon atoms, haloalkyl having 1 to 10 carbon atoms, deuterated alkyl having 1 to 10 carbon atoms, cycloalkyl having 3 to 10 carbon atoms, aryl having 6 to 20 carbon atoms, heteroaryl having 3 to 20 carbon atoms, alkoxy having 1 to 10 carbon atoms, alkylthio having 1 to 10 carbon atoms, trialkylsilyl having 3 to 12 carbon atoms, arylsilyl having 6 to 18 carbon atoms, aryloxy having 6 to 20 carbon atoms or arylthio having 6 to 20 carbon atoms; optionally, said Ar₁And Ar₂In (b), any two adjacent substituents are connected to each other to form a ring.

2. An organic compound according to claim 1, characterised in that Het is selected from the group consisting of:

wherein

Denotes the bond linking Het to L, the remaining two bonds

Are respectively connected with L₁And L₂。

3. An organic compound according to claim 1, characterised in that Het is selected from the group consisting of:

wherein the content of the first and second substances,

represents the position where Het is connected with L,

represents Het and L₁The position of the connection is such that,

represents Het and L₂Position of connection in

Absent, representing connection to that location

In, L₂Is a single bond, Ar₂Is hydrogen.

4. An organic compound according to claim 1, wherein L, L is represented by₁And L₂The same or different, and each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 18 carbon atoms, and a substituted or unsubstituted arylene group having 5 to 18 carbon atomsThe heteroarylene group of (a);

optionally, said L, L₁And L₂Wherein the substituents are independently selected from deuterium, cyano, fluorine, an alkyl group having 1 to 5 carbon atoms, a haloalkyl group having 1 to 5 carbon atoms, a deuterated alkyl group having 1 to 5 carbon atoms, an aryl group having 6 to 12 carbon atoms, or a pyridyl group.

5. An organic compound according to claim 1, wherein L, L is represented by₁And L₂The same or different from each other, and each is 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 terphenylene group, a substituted or unsubstituted fluorenylene group, a substituted or unsubstituted anthrylene group, a substituted or unsubstituted phenanthrylene group, a substituted or unsubstituted dibenzothiophenylene group, a substituted or unsubstituted dibenzofuranylene group, and a substituted or unsubstituted carbazolyl group;

6. An organic compound according to claim 1, wherein L is selected from a single bond or the group consisting of:

7. the organic compound of claim 1, wherein Ar is Ar₁Selected from substituted or unsubstituted aryl with 6-25 carbon atoms and substituted or unsubstituted heteroaryl with 12-18 carbon atoms;

Ar₂selected from hydrogen, deuterium, substituted or unsubstituted aryl group having 6 to 25 carbon atoms, and substituted or unsubstituted heteroaryl group having 12 to 18 carbon atoms;

optionally, the Ar is₁And Ar₂Wherein the substituents are the same or different and are each independently selected from deuterium, halogen, cyano, haloalkyl having 1 to 4 carbon atoms, deuterated alkyl having 1 to 4 carbon atoms, cycloalkyl having 5 to 10 carbon atoms, aryl having 6 to 12 carbon atoms, heteroaryl having 5 to 12 carbon atoms, or trialkylsilyl having 3 to 8 carbon atoms; optionally, Ar₁And Ar₂In (b), any two adjacent substituents are connected to each other to form a fluorene ring or a benzene ring.

8. The organic compound of claim 1, wherein Ar is₁Selected from the group consisting of substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted terphenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted pyrenyl, substituted or unsubstituted perylenyl, substituted or unsubstituted anthryl, substituted or unsubstituted phenanthryl, substituted or unsubstituted dibenzothienyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted spirobifluorenyl;

Ar₂selected from the group consisting of hydrogen, deuterium, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted terphenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted pyrenyl, substituted or unsubstituted perylenyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted phenanthrenylSubstituted dibenzothienyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted spirobifluorenyl;

optionally, the Ar is₁And Ar₂Wherein the substituents are the same or different and are each independently selected from deuterium, fluoro, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, trifluoromethyl, trideuteromethyl, pyridyl, phenyl, naphthyl, dibenzothienyl, dibenzofuranyl, or carbazolyl; optionally, said Ar₁And Ar₂In (b), any two adjacent substituents are connected to each other to form a fluorene ring or a benzene ring.

9. The organic compound according to claim 1,

selected from the following structures:

10. an organic compound according to claim 1, wherein each R is₁、R₂、R₃And R₄Identical or different from each other and are each independently selected from deuterium, fluoro, cyano, trimethylsilyl, trideuteromethyl, trifluoromethyl, cyclopentyl, cyclohexyl, methyl, ethyl, isopropyl, tert-butyl or phenyl.

11. An organic compound according to claim 1, wherein R is₅Selected from methyl, ethyl, n-propyl, isopropyl, tert-butyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, and mixtures thereofSubstituted or unsubstituted naphthyl, substituted or unsubstituted terphenyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted fluorenyl, wherein R is₅Each substituent in (a) is independently selected from deuterium, fluoro, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, trifluoromethyl, trideuteromethyl or phenyl;

is connected to R₅And L is spiro.

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

13. an organic electroluminescent device including an anode and a cathode which are oppositely disposed, and a functional layer which is disposed between the anode and the cathode;

the functional layer comprises an organic compound according to any one of claims 1 to 12;

preferably, the functional layer includes an electron transport layer and a light emitting layer, and the electron transport layer and/or the light emitting layer contain the organic compound.

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