CN113045434B

CN113045434B - Organic compound, and organic electroluminescent device and electronic device using same

Info

Publication number: CN113045434B
Application number: CN202110237053.5A
Authority: CN
Inventors: 刘文强; 李应文; 韩超; 冯震
Original assignee: Shaanxi Lighte Optoelectronics Material Co Ltd
Current assignee: Shaanxi Lighte Optoelectronics Material Co Ltd
Priority date: 2021-03-03
Filing date: 2021-03-03
Publication date: 2022-11-29
Anticipated expiration: 2041-03-03
Also published as: CN113045434A; WO2022183798A1

Abstract

The application relates to an organic compound, and an organic electroluminescent device and an electronic device using the organic compound, wherein the structure of the organic compound is shown as formula 1, and when the organic compound is used as a hole adjusting layer material of the electronic device, the luminous efficiency and the service life of the electronic device can be improved.

。

Description

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

Technical Field

The application belongs to the technical field of organic materials, and particularly provides an organic compound, 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 includes 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 cathode and the anode, an electric field is generated by the two electrodes, 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.

In the prior art, patent CN107459466A discloses a luminescent layer material that can be prepared in an organic electroluminescent device. However, there is still a need to develop new materials to further improve the performance of electronic components.

Disclosure of Invention

An object of the present invention is to provide an organic compound, and an organic electroluminescent device and an electronic device using the same, which can improve the luminous efficiency and the lifetime of the electronic device when the organic compound of the present invention is used for a hole adjustment layer material of the electronic device.

In order to achieve the above object, the present application provides, in a first aspect, an organic compound having a structure represented by formula 1:

in formula 1, ring a is adamantyl or norbornyl;

L ₁ 、L ₂ and L ₃ The same or different, 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;

R ₁ 、R ₂ 、R ₃ 、R ₄ and R ₅ Identical or different from each other and each independently selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, a heteroaryl group having 3 to 30 carbon atoms;

R ₆ selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, and a heteroaryl group having 3 to 30 carbon atoms;

n ₁ 、n ₂ 、n ₄ and n ₆ Are the same or different from each other and are each independently selected from 0, 1,2, 3 or 4; n is a radical of an alkyl radical ₃ Selected from 0, 1,2 or 3;

n ₅ selected from 0, 1,2, 3,4 or 5;

Ar ₁ selected from substituted or unsubstituted aryl with 6-30 carbon atoms and substituted or unsubstituted heteroaryl with 3-30 carbon atoms;

said L ₁ 、L ₂ 、L ₃ And Ar ₁ Wherein the substituents are independently selected from deuterium, a halogen group, a cyano group, a heteroaryl group having 3 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms, a trialkylsilyl group having 3 to 12 carbon atoms, a triarylsilyl group having 18 to 24 carbon atoms, an alkyl group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, an alkenyl group having 2 to 6 carbon atoms, an alkynyl group having 2 to 6 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, a heterocycloalkyl group having 2 to 10 carbon atoms, a cycloalkenyl group having 5 to 10 carbon atoms, a heterocycloalkenyl group having 4 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an alkylthio group having 1 to 10 carbon atoms, an aryloxy group having 6 to 18 carbon atoms, an arylthio group having 6 to 18 carbon atoms, and a phosphinyloxy group having 6 to 18 carbon atoms.

In a second aspect, the present application provides an organic electroluminescent device, comprising an anode and a cathode oppositely arranged, and a functional layer arranged between the anode and the cathode;

the functional layer comprises an organic compound provided in the first aspect of the present application;

preferably, the functional layer includes a hole-adjusting layer containing the organic compound.

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.

Through the technical scheme, one aryl in triarylamine groups is fixed into 9-fluorenyl which is connected through phenylene by the organic compound, and the aryl is combined with a fluorene spiral ring structure, wherein compared with the 9-fluorenyl which is directly connected with the fluorenyl at the 1-4 position, the 9-fluorenyl connected with the phenylene avoids the defect of poor thermal stability of 9, 9-disubstituted fluorenyl, simultaneously makes full use of the excellent hole transmission characteristic of fluorene, and combines the adjustment of the connection position of N and phenyl to ensure that the material has excellent space configuration, has more easily adjustable HOMO energy level, has hole transmission capability which is better than that of the disubstituted fluorenyl connected at the 1-4 position, is not easy to crystallize, is used for an organic electroluminescent device, and can greatly improve the luminous efficiency of the device. Meanwhile, the material has excellent hole transport capability and excellent film forming property of a cycloalkyl-spirofluorene structure, so that the material can keep relatively better service life while keeping high efficiency. Particularly, the introduction of adamantane or norbornane into the fluorene ring can provide good mobility.

When the organic compound is used as a hole adjusting layer of a green light device of an organic electroluminescent device, the luminous efficiency and the service life of the device are effectively improved.

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 diagram of one embodiment of an organic electroluminescent device of the present application;

FIG. 2 is a schematic structural diagram of one embodiment of an electronic device including an organic electroluminescent device of the present application;

fig. 3 is a schematic structural view of another embodiment of an electronic device including the organic electroluminescent device of the present application.

Description of the reference numerals

100 anode 200 cathode 300 functional layers

310 hole injection layer 321 hole transport layer 322 hole adjusting layer

330 organic light-emitting layer 340 hole blocking layer 350 Electron transport layer

360 electron injection layer 400 electronic device 500 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 terms "the" and "said" are used to indicate the presence of one or more elements/components/etc.; the terms "comprising," "including," and "containing" are intended to be inclusive and mean that there may be additional elements/components/etc. other than the listed elements/components/etc.

In a first aspect, the present application provides an organic compound, wherein the structure of the organic compound is shown in formula 1:

in formula 1, ring a is adamantyl or norbornyl;

R ₁ 、R ₂ 、R ₃ 、R ₄ and R ₅ Identical to or different from each other and each independently selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, a heteroaryl group having 3 to 30 carbon atoms;

n ₁ 、n ₂ 、n ₄ and n ₆ Are identical to or different from each otherAnd each is independently selected from 0, 1,2, 3 or 4; n is ₃ Selected from 0, 1,2 or 3;

n ₅ selected from 0, 1,2, 3,4 or 5;

said L is ₁ 、L ₂ 、L ₃ And Ar ₁ Wherein the substituents are independently selected from deuterium, a halogen group, a cyano group, a heteroaryl group having 3 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms, a trialkylsilyl group having 3 to 12 carbon atoms, a triarylsilyl group having 18 to 24 carbon atoms, an alkyl group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, an alkenyl group having 2 to 6 carbon atoms, an alkynyl group having 2 to 6 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, a heterocycloalkyl group having 2 to 10 carbon atoms, a cycloalkenyl group having 5 to 10 carbon atoms, a heterocycloalkenyl group having 4 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an alkylthio group having 1 to 10 carbon atoms, an aryloxy group having 6 to 18 carbon atoms, an arylthio group having 6 to 18 carbon atoms, and a phosphinyloxy group having 6 to 18 carbon atoms.

Preferably, n ₁ 、n ₂ 、n ₃ 、n ₄ 、n ₅ 、n ₆ Each independently is 0.

In the application, the description mode of ' each of the methods is used for ' \8230, independently for ' \8230and ' \8230 \ 8230, independently selected from ' can be interchanged, and are understood in a broad sense, which can mean that specific options expressed between the same symbols in different groups are not influenced with each other, and can mean that specific options expressed between the same symbols in the same groups are not influenced with each other.

For example,'

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

In the present application, the term "substituted or unsubstituted" means that a functional group described later in the term may or may not have a substituent (hereinafter, for convenience of description, the substituent is collectively referred to as Rc). For example, "substituted or unsubstituted aryl" refers to an aryl group or an unsubstituted aryl group having a substituent Rc. Wherein Rc, which is the substituent, may be selected from, for example, deuterium, a cyano group, a halogen group, an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms, a heteroaryl group having 3 to 20 carbon atoms, an alkoxy group having 1 to 40 carbon atoms, an alkylthio group having 1 to 25 carbon atoms, a methylsilyl group having 1 to 20 carbon atoms, an arylsilyl group having 6 to 25 carbon atoms, an aryloxy group having 6 to 25 carbon atoms, and an arylthio group having 6 to 25 carbon atoms.

In the present application, the number of carbon atoms of a substituted or unsubstituted functional group refers to all the number of carbon atoms in the functional group and the substituents thereon. For example, if Ar ₁ Selected from substituted aryl with 30 carbon atoms, all the carbon atoms of the aryl and the substituent groups on the aryl are 30; as another example, if L ₁ And is selected from substituted arylene having 15 carbon atoms, all of the carbon atoms of the arylene and the substituents thereon are 15 carbon atoms.

In the present application, the number of carbon atoms refers to all the number of carbon atoms. For example: l is a radical of an alcohol ₁ In the case of a substituted arylene group having 12 carbon atoms, all of the carbon atoms of the arylene group and the substituents therein are 12. For example: ar (Ar) ₁ Is composed of

The number of carbon atoms is 7; l is ₁ Is composed of

The number of carbon atoms is 12. This applicationAryl refers to an optional functional group or substituent derived from an aromatic carbocyclic ring.

In the present application, an aryl group may be a monocyclic aryl group (e.g., phenyl) or a polycyclic aryl group, in other words, an aryl group may be a monocyclic aryl group, a fused-ring aryl group, two or more monocyclic aryl groups linked by a carbon-carbon bond conjugate, a monocyclic aryl group and a fused-ring aryl group linked by a carbon-carbon bond conjugate, two or more fused-ring aryl groups linked by a carbon-carbon bond conjugate. 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 heteroatoms such as B, N, O, S, P, se, si and the like. For example, in the present application, phenyl and the like are aryl groups. Examples of aryl groups may include, but are not limited to, phenyl, naphthyl, fluorenyl, 9-dimethylfluorenyl, spirobifluorenyl, indenyl, anthracenyl, phenanthrenyl, biphenylyl, terphenylyl, quaterphenylyl, pentabiphenylyl, benzo [9,10 ] biphenyl]Phenanthryl, pyrenyl, fluoranthenyl, benzofluoranthenyl,

Perylene groups, and the like. The "aryl" groups herein may have one or more linkages to the rest of the molecule. In the present application, the substituted aryl group may be an aryl group in which one or two or more hydrogen atoms are substituted by a group such as deuterium atom, halogen group, cyano (-CN), aryl group, heteroaryl group, trialkylsilyl group, alkyl group, cycloalkyl group, alkoxy group, alkylthio group, or the like. It is understood that the number of carbon atoms of a substituted aryl group, as used herein, refers to the total number of carbon atoms in the aryl group and the substituents on the aryl group, e.g., a substituted aryl group having a carbon number of 20, refers to a total carbon number of 20 in the aryl group and the substituents.

In the present application, the number of carbon atoms of the aryl group having 6 to 30 carbon atoms is, for example, 6 (phenyl), 10 (naphthyl), 12 (biphenyl, for example), 14, 15, 16, 18, 20, 24, 25, or the like.

Specific examples of aryl groups as substituents in the present application include, but are not limited to: phenyl, naphthyl, biphenyl, terphenyl, phenanthryl, anthracyl, fluorenyl, and the like.

In the present application, the term "arylene" refers to a group formed by an aryl group further deprived of a hydrogen atom. In some embodiments of the present application, arylene comprises groups formed by aryl groups further deprived of one or two or more hydrogen atoms, such as arylene groups. The definition of aryl may apply to arylene and arylene groups.

In the present application, heteroaryl refers to a monovalent aromatic ring containing 1,2, 3,4, 5, 6, or 7 heteroatoms in the ring, which may be at least one of B, O, N, P, si, se, and S, or derivatives thereof. The heteroaryl group may be a monocyclic heteroaryl group or a polycyclic heteroaryl group, in other words, the heteroaryl group may be a single aromatic ring system or a plurality of aromatic ring systems connected by carbon-carbon bonds in a conjugated manner, and any one of the aromatic ring systems is an aromatic monocyclic ring or an aromatic fused ring. Illustratively, heteroaryl groups may include thienyl, furyl, pyrrolyl, imidazolyl, thiazolyl, oxazolyl, oxadiazolyl, triazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, acridinyl, pyridazinyl, pyrazinyl, quinolyl, quinazolinyl, quinoxalinyl, phenothiazinyl, phenoxazinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, isoquinolyl, indolyl, carbazolyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothienyl, 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. It is understood that a "heteroaryl" group may have one, two, or more bonds attached to other parts of the molecule.

In the present application, the carbon number of the heteroaryl group having 3 to 30 carbon atoms is, for example, 3,4, 5, 8, 9, 12, 15, 18, 24, etc. The number of carbon atoms of the arylene group having 6 to 18 carbon atoms is, for example, 6, 12, 18, or the like.

Specific examples of heteroaryl groups as substituents in the present application include, but are not limited to: phenanthroline, furyl, thienyl, pyridyl, dibenzofuryl, dibenzothienyl, carbazolyl, N-phenylcarbazolyl, and the like.

In the present application, "alkyl" refers to a saturated straight or branched chain monovalent hydrocarbon radical, wherein the alkyl radical may be optionally substituted with one or more substituents described herein. Specifically, the alkyl group having 1 to 20 carbon atoms may be a straight-chain alkyl group having 1 to 20 carbon atoms or a branched-chain alkyl group having 3 to 20 carbon atoms. The number of carbon atoms may be, for example, 1,2, 3,4, 5, 6, 7, 8, 9,10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20. In some embodiments, alkyl groups herein contain 1 to 10 carbon atoms; in other embodiments, the alkyl groups herein contain 1 to 6 carbon atoms; in still other embodiments, the alkyl groups herein contain 1 to 4 carbon atoms; in other embodiments, alkyl groups herein contain 1 to 3 carbon atoms. Specific examples of the alkyl group include, but are not limited to, methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 2-methylpentyl, 2-ethylbutyl, heptyl, n-heptyl, octyl, n-octyl, tert-octyl, n-nonyl, decyl, and the like. Examples of alkyl groups of 1 to 4 carbon atoms in the present application include, but are not limited to: methyl (Me, -CH) ₃ ) Ethyl (Et, -CH) ₂ CH ₃ ) N-propyl (n-Pr, -CH) ₂ CH ₂ CH ₃ ) Isopropyl (i-Pr, -CH (CH) ₃ ) ₂ ) N-butyl (n-Bu, -CH) ₂ CH ₂ CH ₂ CH), tert-butyl (t-Bu, -C (CH) ₃ ) ₃ ) And so on.

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

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

Throughout this document, groups do not explicitly indicate whether or not they are substituted, and are all unsubstituted.

For connecting keys in this application

And (4) showing.

In this application, 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 runs, 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 dibenzofuranyl group represented by formula (X') is attached to another position of the molecule via an delocalized bond extending from the middle of the phenyl ring on one side, which has the meaning shown in any of the possible attachment means as shown in formulas (X '-1) to (X' -4).

In one embodiment of the present application, ar ₁ Selected from substituted or unsubstituted aryl groups having 6 to 20 carbon atoms and substituted or unsubstituted heteroaryl groups having 12 to 20 carbon atoms.

Alternatively, the first and second liquid crystal display panels may be,Ar ₁ the substituent(s) is (are) deuterium, a halogen group, a cyano group, an alkyl group having 1 to 5 carbon atoms, an aryl group having 6 to 12 carbon atoms, a heteroaryl group having 12 to 14 carbon atoms, or a haloalkyl group having 1 to 5 carbon atoms.

Specifically, ar ₁ Specific examples of the substituent(s) include, but are not limited to: deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, phenyl, naphthyl, biphenyl, phenanthryl, dimethylfluorenyl, dibenzofuranyl, dibenzothienyl, carbazolyl, trifluoromethyl, and the like.

In another embodiment of the present application, ar ₁ Selected from the group consisting of substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted dimethylfluorenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted 9, 9-dimethyl-9H-9-silafluorenyl, substituted or unsubstituted dibenzothienyl, substituted or unsubstituted dibenzofuranyl, and substituted or unsubstituted carbazolyl.

In one embodiment of the present application, ar is ₁ Selected from the group consisting of substituted or unsubstituted W, said unsubstituted group W being selected from the group consisting of:

wherein the content of the first and second substances,

represents a chemical bond; when the group W is substituted with one or more substituents, each of said substituents, which may be the same or different, is independently selected from: deuterium, fluoro, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, phenyl, naphthyl, biphenyl, trifluoromethyl.

Alternatively, ar ₁ Selected from the group consisting of:

in one embodiment of the present application, L is ₁ 、L ₂ And L ₃ The substituents are the same or different, and each is independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, and a substituted or unsubstituted heteroarylene group having 12 to 20 carbon atoms.

Optionally, said L ₁ 、L ₂ And L ₃ Wherein the substituents in (A) are independently selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 5 carbon atoms, and an aryl group having 6 to 12 carbon atoms.

Specifically, the L ₁ 、L ₂ And L ₃ Specific examples of the substituent in (1) include, but are not limited to: deuterium, fluoro, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, phenyl, naphthyl, biphenyl.

In one embodiment of the present application, L ₁ 、L ₂ And L ₃ The same or different, each is independently selected from a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted phenanthrylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted fluorenylene group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, and a substituted or unsubstituted N-phenylcarbazolylidene group.

In another embodiment of the present application, said L ₁ 、L ₂ And L ₃ Each independently selected from a single bond, a substituted or unsubstituted group V; the unsubstituted group V is selected from the group consisting of:

wherein, the first and the second end of the pipe are connected with each other,

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

Optionally, the

Selected from the group consisting of:

alternatively, L ₃ Selected from single bonds or phenylene.

Further optionally, L ₃ Selected from the group consisting of single bonds or the following groups:

in one embodiment of the present application, R is ₁ 、R ₂ 、R ₃ 、R ₄ And R ₅ Identical to or different from each other and each independently selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 15 carbon atoms, an aryl group having 6 to 25 carbon atoms, a heteroaryl group having 3 to 25 carbon atoms;

preferably, said R is ₁ 、R ₂ 、R ₃ 、R ₄ And R ₅ Identical to or different from each other and each independently selected from deuterium, a halogen group, a cyano group, a methyl group, an ethyl group, an n-propyl group, an isopropyl group, a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a phenyl group, a naphthyl group, a phenanthryl group, an anthracyl group, a carbazolyl group, a dibenzothienyl group, a dibenzofuranyl group.

R ₆ Selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 15 carbon atoms, and a heteroaryl group having 3 to 25 carbon atoms;

preferably, said R is ₆ Selected from deuterium, halogen groups, cyano, methyl, ethyl, n-propyl, isopropyl, cyclopropyl, cyclobutyl, cyclopentyl, carbazolyl, dibenzothienyl, dibenzofuranyl.

In one embodiment of the present application, n ₁ ，n ₂ ，n ₃ ，n ₄ ，n ₅ ，n ₆ Are all 0.

In the present application, the adamantyl group refers to an unsubstituted adamantyl group, and the norbornyl group refers to an unsubstituted norbornyl group.

In one embodiment herein, the ring a is selected from the group consisting of:

in one embodiment of the present application, the organic compound is selected from one or more of the following organic compounds:

in a second aspect, the present application provides an organic electroluminescent device comprising an anode and a cathode oppositely disposed, and a functional layer disposed between the anode and the cathode.

For example, as shown in fig. 1, the organic electroluminescent device may include an anode 100 and a cathode 200 oppositely disposed, and a functional layer 300 disposed between the anode 100 and the cathode 200; the functional layer 300 contains an organic compound provided herein. In one embodiment herein, the functional layer 300 comprises a hole adjusting layer 322, the hole adjusting layer 322 comprising an organic compound as provided herein.

According to one embodiment, the organic electroluminescent device may be, for example, a green organic electroluminescent device.

In one embodiment of the present application, the organic electroluminescent device may include an anode 100, a hole transport layer 321, a hole adjusting layer 322, an organic light emitting layer 330 as an energy conversion layer, an electron transport layer 350, and a cathode 200, which are sequentially stacked. In the present application, the anode 100 contains an anode material, which is preferably a material having a large work function (work function) that facilitates hole injection into the functional layerfunction) material. 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 such as ZnO: al or SnO ₂ : sb; 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, the anode 1 includes a transparent electrode including Indium Tin Oxide (ITO) as an anode.

In the present application, as shown in fig. 1, 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. In one embodiment of the present application, the hole injection layer 310 may be composed of HAT-CN.

In this application, a hole transport layer 321 may be further disposed between the hole injection layer 310 and the hole adjusting layer 322, and the hole transport layer 321 may further 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 particularly limited in this application. For example, in one embodiment of the present application, the compound NPB is contained in a hole transport layer, which is adjacent to the hole injection layer 310.

In the present application, the functional layer 300 includes a hole adjusting layer 322, and the hole adjusting layer 322 includes an organic compound provided herein. The hole adjusting layer 322 may be composed of the organic compound provided herein, or may be composed of the organic compound provided herein and other materials.

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 holes injected into the organic light emitting layer 330 and holes injected into the organic light emitting layerThe electrons of 330 may recombine in the organic light emitting layer 330 to form excitons, which transfer energy to the host material, which 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 doping 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. For example, the organic light emitting layer 330 may contain CBP and Ir (ppy) ₃ 。

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

Alternatively, the electron transport layer 350 may have a single-layer structure or a multi-layer structure, and may include one or more electron transport materials, which may be 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 TPyQB and LiQ.

In the present application, as shown in fig. 1, an electron injection layer 360 may be further disposed between the cathode 200 and the electron transport layer 350 to enhance the ability to inject electrons into the electron transport layer 350. The electron injection layer 360 may include an inorganic material such as an alkali metal sulfide or an alkali metal halide, or may include a complex of an alkali metal and an organic material. In one embodiment of the present application, the electron injection layer 360 may include ytterbium (Yb).

In one embodiment of the present disclosure, a hole blocking layer 340 may be further disposed between the organic light emitting layer 330 and the electron transport layer 350.

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. Since the electronic device has the organic electroluminescent device described above, the electronic device has the same advantages, and the description of the electronic device is omitted here.

For example, as shown in fig. 2, the present application provides an electronic device 400, wherein the electronic device 400 includes any one of the organic electroluminescent devices described in the above organic electroluminescent device embodiments. The electronic device 400 may be a display device, a lighting device, an optical communication device or other types of electronic devices, and may include, for example and without limitation, a computer screen, a mobile phone screen, a television, electronic paper, an emergency light, an optical module, and the like. Since the electronic device 400 has any one of the organic electroluminescent devices described in the above embodiments of the organic electroluminescent device, the same advantages are obtained, and details are not repeated herein.

As another example, as shown in fig. 3, the present application provides an electronic device 500, where the electronic device 500 includes any one of the photoelectric conversion devices described in the above embodiments of the photoelectric conversion device. The electronic device 500 may be a solar power generation device, a light detector, a fingerprint recognition device, a light module, a CCD camera, or other types of electronic devices. Since the electronic device 500 has any one of the photoelectric conversion devices described in the above embodiments of the photoelectric conversion device, the same advantages are obtained, and details are not repeated herein.

The present application is further illustrated by the following examples, which, however, are not to be construed as limiting in any way

EXAMPLE 1 preparation of intermediates

1, 2-dibromo-3-chlorobenzene (80.0g, 298.7mmol), phenylboronic acid (36.5g, 298.7mmol), tetratriphenylphosphine 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 (600 mL), ethanol (150 mL) and water (150 mL) 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 by using anhydrous magnesium sulfate, and removing the solvent under reduced pressure to obtain a crude product; purification by silica gel column chromatography using dichloromethane/n-heptane as mobile phase crude gave the product intermediate a-1 as a white solid (42.0 g, 53%).

The intermediates b-1 and c-1 shown in Table 1 were synthesized by referring to the intermediate a-1 by substituting the reactant A in Table 1 for 1, 2-dibromo-3-chlorobenzene.

TABLE 1

1-bromo-2-iodobenzene (50g, 176.73mmol), 3-chlorobenzeneboronic acid (27.64g, 176.73mmol), tetrakistriphenylphosphine palladium (1.02g, 0.88mmol), potassium carbonate (48.79g, 353.4 mmol), tetrabutylammonium bromide (11.4 g, 35.3 mmol) was added to the flask and a mixed solvent of toluene (400 mL), ethanol (100 mL) and water (100 mL) was added, warmed to 80 ℃ under nitrogen and stirred for 12 hours maintaining the temperature; cooling to room temperature, stopping stirring, washing the reaction solution with water, separating an organic phase, drying by using 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 mobile phase gave the product intermediate d-1 as a white solid (29.3 g.

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

The intermediates B-2, c-2 and d-2 shown in Table 2 were synthesized by referring to the intermediate a-2 by replacing the intermediate a-1 with the reactant B shown in Table 2.

TABLE 2

Adding the intermediate a-2 (25.8g, 76.3mmol) and glacial acetic acid (300 mL) into a flask, slowly dropwise adding a concentrated sulfuric acid (98%) (0.8mL, 15.3mmol) solution in acetic acid (20 mL) under the conditions of nitrogen protection, 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 silica gel column chromatography using a dichloromethane/n-heptane system to yield intermediate a-3 as a white solid (20.4g.

The intermediates b-3, C-3 and d-3 shown in Table 3 were synthesized by referring to the intermediate a-3 by replacing the intermediate a-2 with the reactant C shown in Table 3.

TABLE 3

Adding the intermediate a-1 (42.0 g, 157.9 mmol) and tetrahydrofuran (300 mL) into a flask, cooling to-78 ℃ under the protection of nitrogen, dropwise adding 236.9mmol of tetrahydrofuran (2.5M) solution of n-butyllithium (95mL) under stirring, keeping the temperature and stirring for 1 hour after dropwise adding, dropwise adding tetrahydrofuran (100 mL) solution dissolved with norborneone (17.29g, 156.98mmol) at-78 ℃, keeping the temperature for 1 hour after dropwise adding, then heating to room temperature, and stirring for 24 hours; a solution of hydrochloric acid (12M) (26.3ml, 315.8mmol) in water (100 mL) 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, drying, and removing a solvent under reduced pressure to obtain a crude product; the crude product was purified by silica gel column chromatography using an ethyl acetate/n-heptane system to give the product intermediates a-ii as white solids (23.92g, 51%).

Intermediates b to II, intermediates c to II and intermediates D to II shown in Table 4 were synthesized by referring to intermediates a to II by substituting the intermediate a to 1 with the reactant D shown in Table 4.

TABLE 4

Adding the intermediate a-II (23.92g, 80.05mmol) and glacial acetic acid (300 mL) into a flask, slowly dropwise adding a concentrated sulfuric acid (98%) (0.8mL, 15.3mmol) solution in acetic acid (20 mL) under the condition of nitrogen protection and normal temperature stirring, raising the temperature to 80 ℃ after dropwise adding, and stirring for 2 hours; cooling to room temperature, filtering the precipitated solid, leaching a filter cake by using water and ethanol, and drying to obtain a crude product; the crude product was purified by silica gel column chromatography using a dichloromethane/n-heptane system to give white solid intermediates a-iii (20.0 g, 89%).

Intermediates b to III, intermediates c to III and intermediates d to III shown in Table 5 were synthesized by referring to the intermediates a to III using the reactant E shown in Table 5 in place of the intermediates a to II.

TABLE 5

EXAMPLE 2 Synthesis of Compound 2

Intermediate a-3 (12.57g, 39.17mmol), 3-aminobiphenyl (6.63g, 39.17mmol), tris (dibenzylideneacetone) dipalladium (0.18g, 0.2mmol), 2-dicyclohexylphosphonium-2 ',4',6' -triisopropylbiphenyl (0.2g, 0.4mmol), sodium tert-butoxide (5.64g, 58.76mmol) and toluene (50 mL) were added to the flask and stirred at 110 ℃ 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 silica gel column chromatography using a dichloromethane/n-heptane system to yield intermediate b-3 as a white solid (11.55g. Mass spectrum: m/z =454.13[ M ] +H] ⁺ 。

Intermediate b-3 (11.55g, 25.46mmol), starting material RM-a (10.12g, 25.46mmol), tris (dibenzylideneacetone) dipalladium (0.23g5 mmol), 2-dicyclohexylphosphonium-2 ',4',6' -triisopropylbiphenyl (0.23 g;0.46 mmol), sodium tert-butoxide (3.67 g;38.19 mmol) and toluene (96 mL) were added to the flask and stirred under reflux at 108 ℃ for 4 hours under nitrogen protection; 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 silica gel column chromatography using a dichloromethane/n-heptane system to yield compound 2 as a white solid (6.86g. Mass spectrum: m/z =770.3[ M ] +H] ⁺ 。

EXAMPLE 3 Synthesis of Compound 450

Intermediate c-iii (12.57g, 39.17mmol), intermediate c (13.06g, 39.17mmol), tris (dibenzylideneacetone) dipalladium (0.18g, 0.2mmol), 2-dicyclohexylphosphonium-2 ',4',6' -triisopropylbiphenyl (0.2g, 0.4mmol), sodium tert-butoxide (5.64g, 58.76mmol) and toluene (50 mL) were added to the flask and stirred at reflux at 110 ℃ for 4 hours under nitrogen; 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 c-4 as a white solid (10.86g.

Intermediate c-4 (10.86g, 18.8 mmol), 3-bromodibenzothiophene (4.92g, 18.8 mmol), tris (dibenzylideneacetone) dipalladium (0.23g, 0.25mmol), 2-dicyclohexylphosphorus-2 ',4',6' -triisopropylbiphenyl (0.23g, 0.46mmol), sodium tert-butoxide (3.67g, 38.19mmol) and toluene (96 mL) were added to the flask and stirred at 108 ℃ under nitrogen; 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; crude product ofPurification by silica gel column chromatography using a dichloromethane/n-heptane system gave compound 450 (6.14g. Mass spectrum: m/z =760.3[ m ] +H] ⁺ 。

EXAMPLE 4 Synthesis of Compound 285

Intermediate a-3 (20.4 g, 63.7 mmol), pinacoldiboron (19.4 g, 76.5 mmol), tris (dibenzylideneacetone) dipalladium (0.6 g, 0.6 mmol), 2-dicyclohexylphosphonium 2',4',6' -triisopropylbiphenyl (0.6 g, 1.3 mmol), potassium acetate (12.5g, 127.4 mmol) and 1, 4-dioxane (150 mL) were added to the flask and stirred at 100 ℃ under nitrogen protection for 16 hours under reflux; cooling to room temperature, adding dichloromethane and water into the reaction solution, separating, 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-4 as a white solid (13.3g, 51%).

Intermediates b-4, c-4, d-4, intermediates a-IV, intermediates b-IV, intermediates c-IV and intermediates d-IV shown in Table 6 were synthesized by referring to the intermediates a-4 by replacing the intermediates a-3 with the reactant F shown in Table 6.

TABLE 6

Intermediate b-4 (13.3g, 32.3mmol), 3-chloroaniline (4.12g, 32.3mmol), tetrakistriphenylphosphine palladium (0.7g, 0.6 mmol), potassium carbonate (11.1g, 80.7mmol), tetrabutylammonium bromide (2.1g, 6.5mmol) were added to the flask and a mixed solvent of toluene (80 mL), ethanol (20 mL) and water (20 mL) was added, warmed to 80 ℃ under nitrogen and stirred for 24 hours with temperature maintained; 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 silica gel column chromatography using dichloromethane/n-heptane as mobile phase gave the product intermediate b-5 as a white solid (7.56g 62%.

Intermediate b-5 (7.56g, 20.0mmol), bromobenzene (3.14g, 20.0mmol), tris (dibenzylideneacetone) dipalladium (0.18g, 0.2mmol), 2-dicyclohexylphosphonium-2 ',4',6' -triisopropylbiphenyl (0.2g, 0.4mmol), sodium tert-butoxide (5.64g, 58.76mmol) and toluene (50 mL) were added to the flask, and stirred at 105 ℃ under nitrogen protection at reflux for 3 hours; cooling to room temperature, washing the reaction solution with water, separating liquid, washing the organic phase with water, drying with anhydrous magnesium sulfate, and removing the solvent under reduced pressure to obtain a crude product; the crude product was purified by silica gel column chromatography using a dichloromethane/n-heptane system to afford intermediate b-6 as a white solid (6.35g, 70%). Mass spectrum: m/z =454.13[ m ] +H] ⁺ 。

Intermediate b-6 (6.35g, 14mmol), bromobenzene (5.56g, 14.0mmol), tris (dibenzylideneacetone) dipalladium (0.18g, 0.2mmol), 2-dicyclohexylphosphonium-2 ',4',6' -triisopropylbiphenyl (0.2g, 0.4mmol), sodium tert-butoxide (5.64g, 58.76mmol) and toluene (50 mL) were added to the flask and stirred at 105 ℃ under nitrogen protection under reflux for 3 hours; cooling to room temperature, washing the reaction solution with water, separating liquid, washing the organic phase with water, drying with anhydrous magnesium sulfate, and removing the solvent under reduced pressure to obtain a crude product; the crude product was purified by silica gel column chromatography using a dichloromethane/n-heptane system to give compound 285 (6) as a white solid.35g of a soybean milk powder; 61%). Mass spectrum: m/z =744.26[ m ] +H] ⁺ 。

Referring to the synthesis of compound 2, and using starting material 1 instead of intermediate a-3, starting material 2 instead of 3-aminobiphenyl, and starting material 3 instead of starting material RM-a, the compounds shown in table 7 were prepared. Wherein, the number, structure, raw materials, synthesis yield of the last step, characterization data and the like of the compound are shown in table 7.

Table 7: structure, preparation and characterization data of the Compounds

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

TABLE 8

Example 1: production of green organic electroluminescent device

The anode 1 was prepared by the following procedure: the thickness of ITO is set as

The ITO substrate is cut into a length of 40mm40mm (width) × 0.7mm (thickness), prepared by photolithography process as experimental substrate having cathode 5, anode 1 and insulating layer patterns, and using ultraviolet ozone and O ₂ :N ₂ Plasma is used for surface treatment to increase the work function of the anode 1, and an organic solvent can be used for cleaning the surface of the ITO substrate to remove impurities and oil stains on the surface of the ITO substrate. It should be noted that the ITO substrate may also be cut into other sizes according to actual needs, and the size of the ITO substrate in this application is not particularly limited.

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

And NPB is vacuum-evaporated on the hole injection layer to form a layer having a thickness of

The hole transport layer of (1).

Compound 2 is vacuum deposited on the hole transport layer to a thickness of

The hole adjusting layer of (2).

Then, on the hole adjusting layer, ir (ppy) having CBP as a main component ₃ As a dopant. According to the weight percentage of the materials as 90%: co-evaporation is carried out at a ratio of 10% to form a film having a thickness of

Green emitting layer (EML).

TPyQB and LiQ were then mixed at a weight ratio of 1

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

And then the Electron Injection Layer (EIL) ofMagnesium (Mg) and silver (Ag) were mixed at a deposition rate of 1

The cathode of (1).

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

CP-1, thereby completing the fabrication of the organic electroluminescent device.

The structure of the organic compound used in example 1 is shown below:

examples 2 to 25

Organic electroluminescent devices were produced in the same manner as in example 1, except that compounds shown in examples 2 to 25 in Table 9 were used instead of compound 2 in the formation of the hole-adjusting layer, respectively, and the performance parameters of each device are specified in Table 9.

Comparative examples 1 to 6

Organic electroluminescent devices were produced in the same manner as in example 1, except that compounds a to F were used instead of compound 2 in the formation of the hole-adjusting layer, respectively, and the performance parameters of each device are specified in table 9. The structural formulas of the compounds A to F are respectively shown as follows:

in the examples and comparative examples, IVL (Current, voltage, brightness) data were compared at 10mA/cm ² As a result of the test, T95 lifetime was 20mA/cm ² Test results at current density.

TABLE 9 Green organic electroluminescent device Properties

From the results of table 9 above, it is understood that the organic electroluminescent devices of examples 1 to 25 using the compounds of the present application as the hole-adjusting layer are highly improved in both the light-emitting efficiency and the device lifetime as compared with comparative examples 1 to 6 using compounds a to F. Wherein, the luminous efficiency is improved by at least 20.7%, and the service life is improved by at least 42%.

From the above results, it is clear that the compounds of the present application are improved in both efficiency and life as compared with the compounds a to D of comparative examples 1 to 4. For this reason, it is possible that the organic compound of the present application avoids the disadvantage of poor thermal stability of 9,9-dimethylfluorene by introducing a phenyl group between the arylamine group and the 9-position of the fluorenyl group.

Compared with comparative examples 5 and 6, in the triarylamine structure of the compound, one aryl is a fluorenyl with 9-position screw-joint polycyclic alkyl, the other aryl is a phenylene substituted by 9-phenylfluorenyl, the spatial structures of the aromatic groups connected with nitrogen in the arylamine are more matched, the compound has stronger rigidity and more proper steric hindrance, and the hole mobility and the thermal stability of the compound can be improved. Therefore, when the compound is used as a hole adjusting layer of a green device, the luminous efficiency and the service life of the device are remarkably improved.

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

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

In addition, any combination of the various embodiments of the present application can be made, and the same shall be considered as the disclosure of the present application as long as the idea of the present application is not violated.

Claims

1. An organic compound, wherein the structure of the organic compound is represented by formula 1:

in formula 1, ring a is adamantyl or norbornyl;

L ₁ 、L ₂ and L ₃ Each independently selected from a single bond, a substituted or unsubstituted group V; the unsubstituted group V is selected from the group consisting of:

wherein the content of the first and second substances,

represents a chemical bond; when group V is substituted with one or more substituents, each of said substituents, which may be the same or different, is independently selected from: deuterium, fluoro, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, phenyl, naphthyl;

R ₆ selected from deuterium, halogen group, cyano group, alkyl group having 1 to 20 carbon atomsCycloalkyl of 3 to 20, heteroaryl of 3 to 30 carbon atoms;

n ₁ ，n ₂ ，n ₃ ，n ₄ ，n ₅ ，n ₆ are all 0;

Ar ₁ selected from the group consisting of substituted or unsubstituted groups W selected from the group consisting of:

wherein the content of the first and second substances,

2. The organic compound of claim 1, wherein L is ₁ 、L ₂ And L ₃ The same or different, each independently selected from a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, and a substituted or unsubstituted biphenylene group.

3. The organic compound of claim 2, wherein L is ₁ 、L ₂ And L ₃ Wherein the substituents in (A) are independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, phenyl and naphthyl.

4. An organic compound according to claim 1, wherein ring a is selected from the group consisting of:

5. the organic compound of claim 1, wherein the organic compound is selected from one or more of the following organic compounds:

6. an organic electroluminescent device is characterized by comprising an anode and a cathode which are oppositely arranged, and a functional layer arranged between the anode and the cathode;

the functional layer comprises an organic compound according to any one of claims 1 to 5.

7. The organic electroluminescent device according to claim 6, wherein the functional layer comprises a hole adjusting layer containing the organic compound.

8. An electronic device comprising the organic electroluminescent element as claimed in any one of claims 6 to 7.