Organic compound, and electronic element and electronic device using same

文档序号：80545 发布日期：2021-10-08 浏览：23次中文

阅读说明：本技术 一种有机化合物以及使用其的电子元件和电子装置 (Organic compound, and electronic element and electronic device using same ) 是由张孔燕马天天曹佳梅于 2021-05-13 设计创作，主要内容包括：本公开涉及有机材料技术领域,提供了一种有机化合物以及使用其的电子元件和电子装置,所述有机化合物的结构由化学式I和化学式II组成。本申请的有机化合物用于有机电致发光器件时,可以有效地提升器件的器件效率,并延长有机电致发光器件的寿命。(The present disclosure relates to the technical field of organic materials, and provides an organic compound, and an electronic element and an electronic device using the same, wherein the structure of the organic compound is composed of a chemical formula I and a chemical formula II. When the organic compound is used for an organic electroluminescent device, the device efficiency of the device can be effectively improved, and the service life of the organic electroluminescent device is prolonged.)

1. An organic compound, wherein the structure of the organic compound consists of formula I and formula II:

wherein formula I and formula II are fused, representing the point of attachment of formula I to formula II;

in (Ad)_mIn the formula, Ad is an adamantyl group,m represents the number of Ad, and m is selected from 1,2 or 3;

the ring A is selected from a benzene ring or a condensed aromatic ring with 10-14 ring carbon atoms;

Y₁and Y₂Are the same or different and are each independently selected from O, S, C (R)₄R₅)、N(R₆)、Si(R₇R₈) Or Se, wherein R₄～R₈The same or different, and each is independently selected from hydrogen, aryl with 6-18 carbon atoms, heteroaryl with 3-18 carbon atoms, alkyl with 1-10 carbon atoms, cycloalkyl with 3-10 carbon atoms, and optionally R₄And R₅Are linked to each other to form, together with the atoms to which they are commonly attached, a 5-15 membered saturated or unsaturated ring, optionally R₇And R₈Are linked to each other to form, together with the atoms to which they are commonly linked, a 5-15 membered saturated or unsaturated ring;

X₁、X₂、X₃are identical or different and are each independently selected from C (H) or N, where X₁、X₂、X₃At least one of which is N;

R₁、R₂、R₃the same or different, and each is independently selected from deuterium, a halogen group, a cyano group, a trialkylsilyl group having 3-12 carbon atoms, a triarylsilyl group having 18-24 carbon atoms, a substituted or unsubstituted alkyl group having 1-10 carbon atoms, a substituted or unsubstituted alkoxy group having 1-15 carbon atoms, a cycloalkyl group having 3-10 carbon atoms, a substituted or unsubstituted aryl group having 6-30 carbon atoms, and a substituted or unsubstituted heteroaryl group having 3-30 carbon atoms;

R₁、R₂、R₃with R_iIs represented by n₁～n₃With n_iIs represented by n_iRepresents R_iI is a variable, represents 1,2 and 3, and when i is 1 or 2, n is_iSelected from 0, 1,2, 3 or 4; when i is 3, n_iSelected from 0, 1,2, 3,4, 5, 6, 7, 8, 9 or 10; and when n is_iWhen greater than 1, any two n_iThe same or different; optionally, any two adjacent R_iForming a ring;

L₁、L₂and L₃The same or different, and are respectively and independently selected from single bond, substituted or unsubstituted arylene with 6-40 carbon atoms, and substituted or unsubstituted heteroarylene with 3-30 carbon atoms;

Ar₁and Ar₂The aryl groups are the same or different and are respectively and independently selected from substituted or unsubstituted aryl groups with 6-40 carbon atoms and substituted or unsubstituted heteroaryl groups with 2-40 carbon atoms;

R₁、R₂、R₃、Ar₁、Ar₂、L₁、L₂and L₃Wherein the substituents are the same or different and 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, a cycloalkyl group having 3 to 10 carbon atoms, a heterocycloalkyl group having 2 to 10 carbon atoms, and an alkoxy group having 1 to 10 carbon atoms.

2. The organic compound of claim 1, wherein R₁、R₂、R₃、Ar₁、Ar₂、L₁、L₂And L₃Wherein the substituents are the same or different and are independently selected from deuterium, fluorine, cyano, heteroaryl having 3 to 20 carbon atoms, aryl having 6 to 20 carbon atoms, trialkylsilyl having 3 to 7 carbon atoms, triphenylsilyl, alkyl having 1 to 5 carbon atoms, haloalkyl having 1 to 5 carbon atoms, and cycloalkyl having 3 to 10 carbon atoms.

3. The organic compound of claim 1, wherein formula I has a structure according to any one of formulae I-1 to I-5:

4. the organic compound of claim 1, wherein formula I has a structure according to any one of formulae 4-1 to 4-8:

5. the organic compound according to claim 1, wherein ring a is selected from a benzene ring, a naphthalene ring, an anthracene ring, or a phenanthrene ring.

6. The organic compound according to any one of claims 1 to 5, wherein Ar is Ar₁And Ar₂The same or different, and each is independently selected from substituted or unsubstituted aryl with 6-30 carbon atoms and substituted or unsubstituted heteroaryl with 3-30 carbon atoms.

7. The organic compound according to any one of claims 1 to 6, wherein Ar is Ar₁And Ar₂Identical or different and are each independently selected from substituted or unsubstituted groups W selected from the group consisting of:

the substituted group W has one or more substituents, and the substituents in the substituted group W are independently selected from deuterium, fluorine, cyano, alkyl having 1 to 5 carbon atoms, trialkylsilyl having 3 to 7 carbon atoms, fluoroalkyl having 1 to 4 carbon atoms, phenyl, pyridyl, and naphthyl.

8. Root of herbaceous plantThe organic compound according to any one of claims 1 to 7, wherein Ar is Ar₁And Ar₂Are the same or different and are each independently selected from the group consisting of:

9. the organic compound of claim 1, wherein L₁、L₂And L₃The same or different, and each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 32 carbon atoms, and a substituted or unsubstituted heteroarylene group having 3 to 20 carbon atoms.

10. The organic compound of claim 1, wherein L₁、L₂And L₃The same or different, and each independently is a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted pyridylene group, a substituted or unsubstituted dibenzofuranylene group, a substituted or unsubstituted dibenzothiophenylene group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted terphenylene group, a substituted or unsubstituted anthrylene group, a substituted or unsubstituted phenanthrylene group, a substituted or unsubstituted 9, 9' -spirobifluorenylene group, a substituted or unsubstituted 9, 9-dimethylfluorenyl group, a substituted or unsubstituted 9, 9-diphenylfluorenyl group, a substituted or unsubstituted quinolylene group; or a group formed by connecting two or three of the above groups through a single bond; the substituents in the above groups are the same or different and are each independently selected from deuterium, fluorine, cyano, alkyl having 1 to 5 carbon atoms, phenyl, biphenyl, pyridyl, naphthyl, trialkylsilyl having 3 to 7 carbon atoms, and fluoroalkyl having 1 to 5 carbon atoms.

11. The organic compound according to any one of claims 1 to 10, wherein L₁、L₂And L₃Are identical to each otherOr different and each is a single bond, or a substituted or unsubstituted group T₁Unsubstituted radicals T₁Selected from the group consisting of:

substituted radicals T₁Having one or more substituents, substituted radicals T₁Wherein the substituents are independently selected from deuterium, fluorine, cyano, C1-4 alkyl, C3-7 trialkylsilyl, triphenylsilyl, C1-4 fluoroalkyl, phenyl, biphenyl, pyridyl, naphthyl.

12. The organic compound of claim 1, wherein L₁、L₂And L₃The same or different, and each is independently selected from the group consisting of a single bond or the following groups:

13. the organic compound of claim 1, wherein R₁、R₂、R₃The same or different, and each is independently selected from deuterium, fluorine, cyano, trialkylsilyl with 3-7 carbon atoms, triphenylsilyl, alkyl with 1-4 carbon atoms, cycloalkyl with 5-10 carbon atoms, aryl with 6-15 carbon atoms and heteroaryl with 3-18 carbon atoms;

optionally, any two adjacent R_iForm 5-15 membered saturated or unsaturated ring, preferably form benzene ring or naphthalene ring.

14. The organic compound of claim 1, wherein R₆Selected from hydrogen, phenyl, naphthyl and biphenyl.

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

16. an electronic component 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 according to any one of claims 1 to 15.

17. The electronic element according to claim 16, wherein the functional layer comprises an organic light-emitting layer containing the organic compound.

18. The electronic element according to claim 16 or 17, wherein the electronic element is an organic electroluminescent device;

preferably, the organic electroluminescent device is a green device.

19. An electronic device comprising the electronic component according to any one of claims 16 to 18.

Technical Field

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

Background

Organic electroluminescent diodes (OLEDs), as a brand new display technology, have advantages that the existing display technology does not have in various performances, such as full solid state, self-luminous, high brightness, high resolution, wide viewing angle, fast response speed, thin thickness, small volume, light weight, flexible substrate availability, low voltage direct current driving, low power consumption, wide working temperature range, and the like, so that the organic electroluminescent diodes have a very wide application market, for example, in the fields of lighting systems, communication systems, vehicle-mounted displays, portable electronic devices, high-definition displays, and even military. The organic electroluminescent device technology can be used for manufacturing novel display products and novel lighting products, is expected to replace the existing liquid crystal display and fluorescent lamp lighting, and has wide application prospect.

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

In the conventional organic electroluminescent device, the characteristics thereof were determinedThe most important problems of energy are lifetime and efficiency, and as the area of a display increases, a driving voltage increases, luminous efficiency and power efficiency also need to be improved, and a certain lifetime is secured, but efficiency cannot be maximized by simply improving an organic layer. The reason is that when the energy level, T, between the organic layers₁When values, intrinsic properties of the substance (mobility, interface properties, etc.), and the like are optimally combined, both long life and high efficiency can be achieved. In order to fully exploit the excellent properties of organic electronic devices, it is necessary to first support the substance forming the organic layer in the device by a stable and efficient material, such as: a hole injecting substance, a hole transporting substance, a light emitting substance, an electron transporting substance, an electron injecting substance, a light emitting auxiliary layer substance, and the like, but a stable and effective organic layer material for an organic electronic element has not yet been developed. The existing organic electroluminescent materials still have room for improvement in light-emitting properties, and development of new organic electroluminescent materials is urgently needed in the industry.

Disclosure of Invention

In view of the above problems in the prior art, it is an object of the present invention 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 electronic element and an electronic device using the same.

In order to achieve the above objects, the present application provides an organic compound having a structure consisting of formula I and formula II:

wherein formula I and formula II are fused, representing the point of attachment of formula I to formula II;

in (Ad)_mIn the formula, Ad is adamantyl, m represents the number of Ad, and m is selected from 1,2 or 3;

the ring A is selected from a benzene ring or a condensed aromatic ring with 10-14 ring carbon atoms;

Y₁and Y₂Are identical to each otherOr are different and are each independently selected from O, S, C (R)₄R₅) Or N (R)₆)、Si(R₇R₈) Or Se, wherein R₄～R₈The same or different, and each is independently selected from hydrogen, aryl with 6-18 carbon atoms, heteroaryl with 3-18 carbon atoms, alkyl with 1-10 carbon atoms, cycloalkyl with 3-10 carbon atoms, and optionally R₄And R₅Are linked to each other to form, together with the atoms to which they are commonly attached, a 5-15 membered saturated or unsaturated ring, optionally R₇And R₈Are linked to each other to form, together with the atoms to which they are commonly linked, a 5-15 membered saturated or unsaturated ring;

X₁、X₂、X₃are identical or different and are each independently selected from C (H) or N, where X₁、X₂、X₃At least one of which is N;

L₁、L₂and L₃The same or different, and each is independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 40 carbon atoms, and a substitution group having 3 to 30 carbon atomsOr unsubstituted heteroarylene;

A third aspect of the present application provides an electronic device comprising the electronic component according to the second aspect of the present application.

The organic compound has a parent structure of condensed aromatic rings with polycyclic conjugated characteristics, has high bond energy among atoms, has good thermal stability, is favorable for solid-state accumulation among molecules, and can prolong the service life of a device when being used as a light-emitting layer material in an organic electroluminescent device. In the structure, on one hand, the triplet state energy level of the condensed heterocyclic ring is higher, which is beneficial to the transition of excitons of the luminous layer and improves the luminous efficiency; on the other hand, the fused heterocyclic compound can effectively improve the HOMO value due to the existence of a large conjugated segment, is beneficial to the injection of holes, improves the injection efficiency of the holes and realizes a good voltage reduction effect. The large conjugated system enables the transfer of charges in the system to be more effective, and the transition rate of the charges is improved. In the structure, the adamantyl group expands a molecular system, so that the overall molecular weight and asymmetry are enhanced, and the film forming property of the molecule is improved. When the condensed heterocyclic ring segment is connected with the electron-deficient aza-benzene group, the high-efficiency transmission of electrons in the molecule is realized, so that the organic compound can improve the exciton utilization rate, and improve the current efficiency, external quantum efficiency and service life of the device when used as a luminescent layer main body material.

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

Detailed Description

The following detailed description of specific embodiments of the present disclosure is provided in connection with the accompanying drawings. It should be understood that the detailed description and specific examples, while indicating the present disclosure, are given by way of illustration and explanation only, not limitation.

In a first aspect, the present application provides an organic compound having a structure consisting of formula I and formula II:

wherein formula I and formula II are fused, representing the point of attachment of formula I to formula II;

in (Ad)_mIn the formula, Ad is adamantyl, m represents the number of Ad, and m is selected from 1,2 or 3;

the ring A is selected from a benzene ring or a condensed aromatic ring with 10-14 ring carbon atoms;

Y₁and Y₂Are the same or different and are each independently selected from O, S, C (R)₄R₅) Or N (R)₆)、Si(R₇R₈) Or Se, wherein R₄～R₈The same or different, and each is independently selected from hydrogen, aryl with 6-18 carbon atoms, heteroaryl with 3-18 carbon atoms, alkyl with 1-10 carbon atoms, cycloalkyl with 3-10 carbon atoms, and optionally R₄And R₅Are linked to each other to form, together with the atoms to which they are commonly attached, a 5-15 membered saturated or unsaturated ring, optionally R₇And R₈Are linked to each other to form, together with the atoms to which they are commonly linked, a 5-15 membered saturated or unsaturated ring;

X₁、X₂、X₃are identical or different and are each independently selected from C (H) or N, where X₁、X₂、X₃At least one of which is N;

In this application, "' indicates the point of attachment of formula I to formula II" means that formula II is attached to any two adjacent fused positions of the eight fused sites.

In this application, the terms "optional" and "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, two adjacent substituents x form a ring" means that the two substituents may but need not form a ring, including: a case where two adjacent substituents form a ring and a case where two adjacent substituents do not form a ring. For another example, "optionally, R₄And R₅The "saturated or unsaturated ring bonded to each other to form 5 to 15 members together with the atom to which they are bonded" means R₄And R₅May be linked to each other to form a 5-to 15-membered saturated or unsaturated ring together with the atoms to which they are commonly linked, or R₄And R₅Each independently exists.

In the present application, "any two adjacent substituents form a ring," any two adjacent "may include two substituents on the same atom, and may also include two substituents on two adjacent atoms; wherein, when two substituents are present on the same atom, the two substituents may beThe atom to which they are commonly attached forms a saturated or unsaturated ring; when two adjacent atoms have a substituent on each, the two substituents may be fused to form a ring. For example "any two adjacent R_iForm a ring "comprising any two adjacent R₁The atoms linked to each other to be common to them form a ring, or any two adjacent R₂The atoms linked to each other to be common to them form a ring, or any two adjacent R₃The atoms that are linked to each other to be commonly linked to them form a ring. For example: any two adjacent R_iA ring having 6 to 15 carbon atoms or a ring having 6 to 10 carbon atoms can be formed; the ring may be saturated (e.g., five-membered ring)Six-membered ringEtc.) or unsaturated, for example, an aromatic ring, and specific examples of the aromatic ring include benzene ringNaphthalene ringPhenanthrene ringEtc.).

In this application, any one of Ad may be attached to any of the positions of attachment of the structures framed by brackets and fused to the structure of formula II, L₃And can be attached to any of the structures framed by parentheses and fused to formula II.

In the structure of the organic compounds of the present application, - (Ad)_mCan be connected to each Ad inCan be specifically connected to L₁And/or L₂Upper (L)₁And L₂Not a single bond) and may be bonded to Ar₁And/or Ar₂The above step (1); furthermore, - (Ad)_mCan also be connected toAndthe structure formed by the fusion, in particular Ad, may be linked to L₃(L₃Not a single bond), may be bonded toAndat any position in the fused structure formed, for example, on the benzene ring, on the fused ring formed, on the A ring, or on the group Y₁、Y₂And R₁、R₂、R₃If present.

In the structure of the organic compound of the present application,group L of₃Can be connected toAndat any position in the structure formed by the fusion, for example, when the structure formed by the fusion isWhen the group L is₃May be bonded to any of the benzene rings in the structure, may be bonded to ring A, or may be bonded to Y₁Or Y₂On the radical; by way of further example, whenAndthe concrete structure formed by thickening isWhen the group L is₃Can be connected with benzene ring, ring A, naphthalene ring and Y shown in the specific structure₁、Y₂The above.

In one embodiment of the present application, Y₁、Y₂May each be independently selected from C (R)₄R₅)、N(R₆)、Si(R₇R₈) And R is₄～R₈Are all hydrogen. It should be understood that in this embodiment, when Ad and L are used₃And Y₁、Y₂When connecting, R₄～R₈Neither of the corresponding hydrogens is present, i.e., Ad and L₃Directly bonded to C, N and the Si atom described above.

In the present application, the descriptions "… … is independently" … … is independently "and" … … is independently selected from "are interchangeable, and should be understood in a broad sense, which means that the specific options expressed between the same symbols in different groups do not affect each other, or that the specific options expressed between the same symbols in the same groups do not affect 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 that Q substituent groups R ' are arranged on a benzene ring, each R ' can be the same or different, and the options of each R ' are not influenced mutually; the formula Q-2 represents that each benzene ring of biphenyl has Q substituent groups R ', the number Q of the substituent groups R' on the two benzene rings can be the same or different, each R 'can be the same or different, and the options of each R' are not influenced with each other.

In 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 having a substituent Rc or an unsubstituted aryl group. The substituent Rc may be, for example, deuterium, a halogen group, a cyano group, a heteroaryl group, an aryl group, a trialkylsilyl group, a triarylsilyl group, an alkyl group, a haloalkyl group, a cycloalkyl group, a heterocycloalkyl group, an alkoxy group, or the like.

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 L₁Is a substituted arylene group having 12 carbon atoms, all of the carbon atoms of the arylene group and the substituents thereon are 12.

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

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

Examples of the aryl group as a substituent in the present application include, but are not limited to, phenyl, biphenyl, naphthyl, 9-dimethylfluorenyl, 9-diphenylfluorenyl, 9' -spirobifluorenyl, anthracenyl, phenanthrenyl, and the like,And (4) a base.

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

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

In the present application, heteroaryl as a substituent is exemplified by, but not limited to, pyridyl, pyrimidinyl, carbazolyl, dibenzofuranyl, dibenzothienyl, quinolyl, quinazolinyl, quinoxalinyl, quinoline, isoquinoline.

As used herein, an delocalized linkage refers to a single bond extending from a ring systemIt means that one end of the linkage may be attached to any position in the ring system through which the linkage extends, and the other end to the rest of the compound molecule.

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

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

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

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

In the present application, the number of carbon atoms of the cycloalkyl group having 3 to 10 carbon atoms may be, for example, 3,5, 6, 7, 8, 9, or 10. Specific examples of the cycloalkyl group having 3 to 10 carbon atoms include, but are not limited to, cyclopentyl, cyclohexyl, and adamantyl. The number of carbon atoms of the cycloalkyl group may be, for example, 3,5, 6, 7, 8, 9 or 10. Specific examples of cycloalkyl groups include, but are not limited to, cyclopentyl, cyclohexyl, adamantyl.

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

Specific examples of the trialkylsilyl group herein include, but are not limited to, trimethylsilyl group, triethylsilyl group, and the like.

Specific examples of haloalkyl groups in the present application include, but are not limited to, trifluoromethyl.

Alternatively, R₁、R₂、R₃、Ar₁、Ar₂、L₁、L₂And L₃Wherein the substituents are the same or different and are independently selected from deuterium, fluorine, cyano, heteroaryl having 3 to 20 carbon atoms, aryl having 6 to 20 carbon atoms, trialkylsilyl having 3 to 7 carbon atoms, triphenylsilyl, alkyl having 1 to 5 carbon atoms, haloalkyl having 1 to 5 carbon atoms, and cycloalkyl having 3 to 10 carbon atoms.

Further alternatively, R₁、R₂、R₃、Ar₁、Ar₂、L₁、L₂And L₃Wherein the substituents are the same or different and are independently selected from deuterium, fluorine, cyano, heteroaryl having 3 to 15 carbon atoms, aryl having 6 to 15 carbon atoms, trialkylsilyl having 3 to 7 carbon atoms, triphenylsilyl, alkyl having 1 to 5 carbon atoms, fluoroalkyl having 1 to 5 carbon atoms, and cycloalkyl having 5 to 10 carbon atoms.

In one embodiment of the present application, the organic compound has a structure represented by any one of formulas 1-1 to 1-6:

alternatively, the organic compound has a structure represented by any one of formulas 2-1 to 2-34:

alternatively, formula I has a structure represented by any one of formulas I-1 through I-5:

alternatively, in the formula I-2,anddifferent; or, in the formula I-2, X₁、X₂And X₃Not N at the same time.

Alternatively, the organic compound has a structure represented by any one of formulas 4-1 to 4-8:

in this application, ring A refers toWherein the ring A is a benzene ring or a condensed aromatic ring having 10 to 14 ring-forming carbon atoms, and the condensed aromatic ring may be, for example, a naphthalene ring, an anthracene ring, or a phenanthrene ring. For example, in the compoundsWherein, ring A is benzene ring, and substituent R on ring A₃The number is 0, Y₂Is N (Ph), Ad is bonded to the benzene ring of N (Ph), L₃Is a single bond, Y₁Represents an N atom. As another example, in the compoundsIn (1), it is understood that ring A is a benzene ring and that the substituent R on ring A₃The number is 0, Y₂Is N (Ph), Ad is bonded to the benzene ring of N (Ph), L₃Is a single bond, Y₁Represents a N atom, any two adjacent R₂A benzene ring is formed.

In some embodiments, Ar₁And Ar₂The same or different and each is independently selected from the group consisting of:

wherein M is₁Selected from a single bond or

G₁～G₅Are the same or different and are each independently selected from N or C (J)₁) And G is₁～G₅At least one is selected from N; when G is₁～G₅Two or more of C (J) are selected from₁) When, two arbitrary J₁The same or different;

G₆～G₁₃are the same or different and are each independently selected from N or C (J)₂) And G is₆～G₁₃At least one is selected from N; when G is₆～G₁₃Two or more of C (J) are selected from₂) When, two arbitrary J₂The same or different;

G₁₄～G₂₃are the same or different and are each independently selected from N or C (J)₃) And G is₁₄～G₂₃At least one ofEach is selected from N; when G is₁₄～G₂₃Two or more of C (J) are selected from₃) When, two arbitrary J₃The same or different;

G₂₄～G₃₃are the same or different and are each independently selected from N or C (J)₄) And G is₂₄～G₃₃At least one is selected from N; when G is₂₄～G₃₃Two or more of C (J) are selected from₄) When, two arbitrary J₄The same or different;

Z₁selected from hydrogen, deuterium, fluorine, chlorine, bromine, cyano-group, trialkylsilyl with 3-12 carbon atoms, triarylsilyl with 18-24 carbon atoms, alkyl with 1-10 carbon atoms, haloalkyl with 1-10 carbon atoms, cycloalkyl with 3-10 carbon atoms, heterocycloalkyl with 2-10 carbon atoms and alkoxy with 1-10 carbon atoms;

Z₂～Z₉、Z₂₁are the same or different and are each independently selected from: hydrogen, deuterium, fluorine, chlorine, bromine, cyano, heteroaryl with 3-20 carbon atoms, trialkylsilyl with 3-12 carbon atoms, triarylsilyl with 18-24 carbon atoms, alkyl with 1-10 carbon atoms, haloalkyl with 1-10 carbon atoms, cycloalkyl with 3-10 carbon atoms, heterocycloalkyl with 2-10 carbon atoms, and alkoxy with 1-10 carbon atoms;

Z₁₀～Z₂₀、J₁～J₄are the same or different and are each independently selected from: hydrogen, deuterium, fluorine, chlorine, bromine, cyano, aryl with 6-20 carbon atoms, heteroaryl with 3-20 carbon atoms, trialkylsilyl with 3-12 carbon atoms, triarylsilyl with 18-24 carbon atoms, alkyl with 1-10 carbon atoms, haloalkyl with 1-10 carbon atoms, cycloalkyl with 3-10 carbon atoms, heterocycloalkyl with 2-10 carbon atoms and alkoxy with 1-10 carbon atoms;

h₁～h₂₁by h_kIs represented by Z₁～Z₂₁With Z_kK is a variable and represents an arbitrary integer of 1 to 21, h_kRepresents a substituent Z_kThe number of (2); wherein, when k is selected from 5 or 17, h_kSelected from 1,2 or 3; when k is selected from 2, 7, 8, 12, 15, 16, 18 or 21, h_kSelected from 1,2, 3 or 4; when k is selected from 1,3, 4,6, 9 or 14, h_kSelected from 1,2, 3,4 or 5; when k is 13, h_kSelected from 1,2, 3,4, 5 or 6; when k is selected from 10 or 19, h_kSelected from 1,2, 3,4, 5, 6 or 7; when k is 20, h_kSelected from 1,2, 3,4, 5, 6, 7 or 8; when k is 11, h_kSelected from 1,2, 3,4, 5, 6, 7, 8 or 9; and when h is_kWhen greater than 1, any two Z_kIdentical or different, optionally, any two adjacent Z_kAre connected with each other to form a ring;

K₁selected from O, S, N (Z)₂₂)、C(Z₂₃Z₂₄) Or Si (Z)₂₅Z₂₆) (ii) a Wherein Z is₂₂、Z₂₃、Z₂₄、Z₂₅、Z₂₆Are the same or different and are each independently selected from: an aryl group having 6 to 20 carbon atoms, a heteroaryl group having 3 to 20 carbon atoms, an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, a heterocycloalkyl group having 2 to 10 carbon atoms, or Z₂₃And Z₂₄Are linked to each other so as to form a saturated or unsaturated ring having 3 to 15 carbon atoms with the atoms linked together, or Z is₂₅And Z₂₆Are linked to each other so as to form a saturated or unsaturated ring having 3 to 15 carbon atoms with the atoms to which they are commonly linked;

K₂selected from single bond, O, S, N (Z)₂₇)、C(Z₂₈Z₂₉) Or Si (Z)₃₀Z₃₁) (ii) a Wherein Z is₂₇、Z₂₈、Z₂₉、Z₃₀、Z₃₁Are the same or different and are each independently selected from: an aryl group having 6 to 20 carbon atoms, a heteroaryl group having 3 to 20 carbon atoms, an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, a heterocycloalkyl group having 2 to 10 carbon atoms, or Z₂₈And Z₂₉Are linked to each other so as to form a saturated or unsaturated ring having 3 to 15 carbon atoms with the atoms to which they are commonly bondedOr Z above₃₀And Z₃₁Are linked to each other so as to form a saturated or unsaturated ring having 3 to 15 carbon atoms with the atoms to which they are linked together.

In the present application, Z is as defined above₂₃And Z₂₄、Z₂₆And Z₂₇、Z₂₈And Z₂₉、Z₃₀And Z₃₁In the four groups, the ring formed by connecting two groups in each group can be a saturated or unsaturated ring with 3-15 carbon atoms. By way of example, formula i-10In, when K₂And M₁Are all single bonds, Z₁₉Is hydrogen, and K₁Is C (Z)₂₃Z₂₄) When Z is₂₃And Z₂₄When they are linked to each other so as to form a 5-membered ring with the atoms to which they are commonly attached, formula i-10 isLikewise, the formula i-10 can also be representedNamely Z₂₃And Z₂₄The atoms that are linked to each other to be commonly bound to them form a partially unsaturated 13-membered ring. Similarly, L is referred to hereinafter₁To L₃Of formula j-8 to formula j-9, E₁₆And E₁₇、E₁₈And E₁₉、E₂₁And E₂₂、E₂₃And E₂₄The rings formed by connecting two groups in each group to each other have similar explanations, and are not described in detail herein.

In the present application, in the formulae i-13 to i-15, J₂To J₄Can be represented by J_jWherein j is a variable, representing 2,3 or 4. For example, when J is 2, J_jMeans J₂. It should be understood that when the delocalized linkage is attached to C (J)_j) When above, C (J)_j) J in (1)_jIs absent. For example, in the chemical formula i-13, whenIs connected to G₁₂When, G₁₂Only C atoms can be represented, namely the structure of the chemical formula i-13 is specifically:

alternatively, Ar₁And Ar₂The aryl group is the same or different and is independently selected from substituted or unsubstituted aryl groups with 6-30 carbon atoms or substituted or unsubstituted heteroaryl groups with 3-30 carbon atoms. For example, Ar₁And Ar₂Each may independently be a substituted or unsubstituted aryl group having 6, 7, 8, 9,10, 14, 15, 16, 17, 18, 20, 21, 25 carbon atoms, or a substituted or unsubstituted heteroaryl group having 3,4, 5,7, 9, 12, 14, 18, 19, 20 carbon atoms.

Alternatively, Ar₁、Ar₂Wherein the substituents are the same or different and are independently selected from deuterium, fluorine, cyano, heteroaryl having 3 to 12 carbon atoms, aryl having 6 to 12 carbon atoms, trialkylsilyl having 3 to 7 carbon atoms, alkyl having 1 to 5 carbon atoms, fluoroalkyl having 1 to 5 carbon atoms, and cycloalkyl having 5 to 10 carbon atoms.

Alternatively, Ar₁And Ar₂The same or different, and each is independently selected from substituted or unsubstituted aryl with 6-15 carbon atoms and substituted or unsubstituted heteroaryl with 5-12 carbon atoms.

In one embodiment, Ar₁And Ar₂The same or different, and each is independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted pyridyl, substituted or unsubstituted naphthyl, substituted or unsubstituted quinolyl, substituted or unsubstituted isoquinolyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted anthryl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted silafluorenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted carbazylAzolyl, substituted or unsubstituted 9, 9' -spirobifluorenyl.

Alternatively, Ar₁And Ar₂The substituents in (a) are the same or different and are each independently selected from deuterium, fluoro, cyano, methyl, ethyl, isopropyl, tert-butyl, phenyl, pyridyl, naphthyl, biphenyl, phenanthryl.

Alternatively, Ar₁And Ar₂Identical or different and are each independently selected from substituted or unsubstituted groups W selected from the group consisting of:

Alternatively, Ar₁And Ar₂Are the same or different and are each independently selected from the group consisting of:

in some embodiments, L₁、L₂And L₃The same or different, and each independently is a single bond or a group represented by formula j-1 to a group represented by formula j-13:

wherein M is₂Selected from a single bond or Represents a chemical bond;

Q₁～Q₅are the same or different and are each independently selected from N or C (J)₅) And Q is₁～Q₅At least one is selected from N; when Q is₁～Q₅Two or more of C (J) are selected from₅) When, two arbitrary J₅The same or different;

Q₆～Q₁₃are the same or different and are each independently selected from N or C (J)₆) And Q is₆～Q₁₃At least one is selected from N; when Q is₆～Q₁₃Two or more of C (J) are selected from₆) When, two arbitrary J₆The same or different;

Q₁₄～Q₂₃are the same or different and are each independently selected from N or C (J)₇) And Q is₁₄～Q₂₃At least one is selected from N; when Q is₁₄～Q₂₃Two or more of C (J) are selected from₇) When, two arbitrary J₇The same or different;

Q₂₄～Q₃₃are the same or different and are each independently selected from N or C (J)₈) And Q is₂₄～Q₃₃At least one is selected from N; when Q is₂₄～Q₃₃Two or more of C (J) are selected from₈) When, two arbitrary J₈The same or different;

E₁～E₁₄、J₅～J₈are the same or different and are each independently selected from: hydrogen, deuterium, fluorine, chlorine, bromine, cyano, heteroaryl with 3-20 carbon atoms, aryl with 6-20 carbon atoms, trialkylsilyl with 3-12 carbon atoms, triarylsilyl with 18-24 carbon atoms, alkyl with 1-10 carbon atoms, haloalkyl with 1-10 carbon atoms, cycloalkyl with 3-10 carbon atoms, heterocycloalkyl with 2-10 carbon atoms and alkoxy with 1-10 carbon atoms;

e₁～e₁₄with e_rIs represented by₁～E₁₄With E_rR is a variable and represents 1 to 14An arbitrary integer, e_rRepresents a substituent E_rThe number of (2); when r is selected from 1,2, 3,4, 5, 6, 9, 13 or 14, e_rSelected from 1,2, 3 or 4; when r is selected from 7 or 11, e_rSelected from 1,2, 3,4, 5 or 6; when r is 12, e_rSelected from 1,2, 3,4, 5, 6 or 7; when r is selected from 8 or 10, e_rSelected from 1,2, 3,4, 5, 6, 7 or 8; when e is_rWhen greater than 1, any two of E_rThe same or different;

K₃selected from O, S, Se, N (E)₁₅)、C(E₁₆E₁₇) Or Si (E)₁₈E₁₉) (ii) a Wherein E is₁₅、E₁₆、E₁₇、E₁₈And E₁₉Are the same or different and are each independently selected from: an aryl group having 6 to 20 carbon atoms, a heteroaryl group having 3 to 20 carbon atoms, an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, a heterocycloalkyl group having 2 to 10 carbon atoms, or E₁₆And E₁₇Are linked to each other so as to form a saturated or unsaturated ring having 3 to 15 carbon atoms with the atoms to which they are commonly linked, or E₁₈And E₁₉Are linked to each other so as to form a saturated or unsaturated ring having 3 to 15 carbon atoms with the atoms to which they are commonly linked;

K₄selected from the group consisting of a single bond, O, S, Se, N (E)₂₀)、C(E₂₁E₂₂) Or Si (E)₂₃E₂₄) (ii) a Wherein E is₂₀To E₂₄Are the same or different and are each independently selected from: an aryl group having 6 to 20 carbon atoms, a heteroaryl group having 3 to 20 carbon atoms, an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, a heterocycloalkyl group having 2 to 10 carbon atoms, or E₂₁And E₂₂Are linked to each other so as to form a saturated or unsaturated ring having 3 to 15 carbon atoms with the atoms to which they are commonly linked, or E₂₃And E₂₄Are linked to each other so as to form a saturated or unsaturated ring having 3 to 15 carbon atoms with the atoms to which they are linked together.

Alternatively, L₁、L₂And L₃Are the same or different and are each independently selected from the group consisting of a single bond, a carbon atomA substituted or unsubstituted arylene group having 6 to 32 subgroups, and a substituted or unsubstituted heteroarylene group having 3 to 20 carbon atoms. For example, L₁、L₂And L₃May each independently be a single bond, or a substituted or unsubstituted arylene group having 6, 7, 8, 9,10, 11, 12, 13, 14, 15, 17, 18, 19, 20 carbon atoms, or a substituted or unsubstituted heteroarylene group having 3,4, 5, 9,10, 12, 14, 18 carbon atoms.

Alternatively, L₁、L₂And L₃Wherein the substituents are the same or different and are independently selected from deuterium, fluorine, cyano, heteroaryl having 3 to 12 carbon atoms, aryl having 6 to 12 carbon atoms, trialkylsilyl having 3 to 7 carbon atoms, alkyl having 1 to 5 carbon atoms, fluoroalkyl having 1 to 5 carbon atoms, and cycloalkyl having 5 to 10 carbon atoms.

Alternatively, L₁、L₂And L₃The same or different, and each independently is a single bond, a substituted or unsubstituted arylene group having 6 to 15 carbon atoms, or a substituted or unsubstituted heteroarylene group having 12 to 18 carbon atoms.

Alternatively, L₁、L₂And L₃Wherein the substituents are the same or different and are each independently selected from deuterium, fluorine, cyano, aryl having 6 to 10 carbon atoms, methyl, ethyl, isopropyl, tert-butyl, heteroaryl having 5 to 12 carbon atoms.

Alternatively, L₁、L₂And L₃The same or different, and each independently is a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted pyridylene group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted terphenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted phenylene group, a substituted or an aromatic hydrocarbon group, a substituted or substituted hydrocarbon group,A substituted or unsubstituted anthrylene group, a substituted or unsubstituted phenanthrylene group, a substituted or unsubstituted 9, 9' -spirobifluorenylene group, a substituted or unsubstituted 9, 9-dimethylfluorenyl group, a substituted or unsubstituted 9, 9-diphenylfluorenyl group, a substituted or unsubstituted quinolylene group; or a group formed by connecting two or three of the above groups through a single bond; the substituents in the above groups are the same or different and are each independently selected from deuterium, fluorine, cyano, alkyl having 1 to 5 carbon atoms, phenyl, biphenyl, pyridyl, naphthyl, trialkylsilyl having 3 to 7 carbon atoms, and fluoroalkyl having 1 to 5 carbon atoms.

Alternatively, L₁、L₂And L₃Identical or different and are each independently a single bond or a substituted or unsubstituted group T₁Unsubstituted radicals T₁Selected from the group consisting of:

Alternatively, L₁、L₂And L₃The same or different, and each independently is a single bond or a group consisting of:

in one embodiment of the present application, R₁、R₂、R₃、Ar₁、Ar₂、L₁、L₂And L₃Wherein the substituents are the same or different and are each independently selected from deuterium, fluoro, cyano, pyridyl, phenyl, naphthyl,Trimethylsilyl, methyl, ethyl, isopropyl, tert-butyl.

Alternatively, R₁、R₂、R₃The same or different, and each is independently selected from deuterium, fluorine, cyano, trialkylsilyl having 3 to 7 carbon atoms, triphenylsilyl, alkyl having 1 to 4 carbon atoms, cycloalkyl having 5 to 10 carbon atoms (e.g., cyclopentyl, cyclohexyl), aryl having 6 to 15 carbon atoms, and heteroaryl having 3 to 18 carbon atoms.

Optionally, any two adjacent R_iForm 5-15 membered saturated or unsaturated ring, preferably form benzene ring or naphthalene ring.

Alternatively, R₁、R₂、R₃Identical or different and are each independently selected from deuterium, fluoro, cyano, methyl, ethyl, isopropyl, tert-butyl, cyclohexyl, phenyl, naphthyl, biphenyl, pyridyl.

Alternatively, n₁、n₂、n₃Are the same or different and are each independently selected from 0, 1 or 2.

Alternatively, R₄～R₈The same or different, each independently selected from alkyl with 1-5 carbon atoms (such as methyl), aryl with 6-18 carbon atoms (such as phenyl, biphenyl, naphthyl).

In the application, Ad can be 1-adamantyl or 2-adamantyl; preferably 1-adamantyl.

In this application, R₆May be selected from hydrogen, phenyl, naphthyl, biphenyl.

In one embodiment, the organic compound has the structure wherein Y is₂Is connected with an Ad; l is₃Is connected at Y₁The above.

In another embodiment, the organic compound has a structure wherein no Ad is attached to the structure of formula II and is attached to Ar₁、Ar₂、L₁、L₂Or Y₁The above.

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

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

A second aspect of the present application provides an electronic component including an anode and a cathode disposed opposite to each other, and a functional layer disposed between the anode and the cathode; the functional layer comprises an organic compound according to the first aspect of the present application. The organic compounds provided herein can be used to form at least one organic film layer in a functional layer to improve efficiency and lifetime characteristics of an electronic component.

Optionally, the functional layer comprises an organic light emitting layer comprising the organic compound. The organic light-emitting layer may be composed of the organic compound provided herein, or may be composed of the organic compound provided herein together with other materials. The organic light emitting layer may be one layer or two or more layers.

Optionally, the electronic element is an organic electroluminescent device.

Optionally, the organic electroluminescent device is a green device.

According to an embodiment, as shown in fig. 1, the organic electroluminescent device may include an anode 100, a hole transport layer 320, an organic light emitting layer 330 as an energy conversion layer, an electron transport layer 340, and a cathode 200, which are sequentially stacked. The hole transport layer 320 may have one or more layers.

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

Optionally, the hole transport layer 320 includes a first hole transport layer 321 and a second hole transport layer 322 stacked in sequence, and the first hole transport layer 321 is closer to the anode 100 than the second hole transport layer 322.

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

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. The host material and/or guest material of the organic light emitting layer may contain the organic compound of the present application. Alternatively, the organic light emitting layer 330 is composed of a host material and a guest material, and a hole injected into the organic light emitting layer 330 and an electron injected into the organic light emitting layer 330 may be combined in the organic light emitting layer 330 to form an exciton, which transfers energy to the host material, and the host material transfers energy to the guest material, thereby enabling the guest material to emit light.

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

In the present application, the cathode 200 may include a cathode material, which is a material having a small work function that facilitates electron injection into the functional layer. Specific examples of the cathode material include, but are not limited to, metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead or alloys thereof; or a multilayer material such as LiF/Al, Liq/Al, LiO₂Al, LiF/Ca, LiF/Al and BaF₂and/Ca. Preferably, a metal electrode comprising magnesium and silver is included as a cathode.

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

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

A third aspect of the present application provides an electronic device comprising the electronic component according to the second aspect of the present application.

According to one embodiment, as shown in fig. 2, the electronic device is an electronic device 400 including the organic electroluminescent device described above. 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.

Compounds for which no synthetic process is mentioned in this application are all commercially available starting products.

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

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

Preparation example 1 preparation of Compound 1

1) Synthesis of intermediate IM 1-1

Adding 1-adamantanol (50.0g, 328.4mmol), bromobenzene (51.6g, 328.4mmol) and dichloromethane (DCM, 500mL) into a round-bottom flask, cooling to-5-0 ℃ under the protection of nitrogen, dropwise adding trifluoromethanesulfonic acid (73.9g, 492.6mmol) at-5-0 ℃, and stirring for 3 hours under heat preservation; adding deionized water (300mL) to the reaction solution, washing with water to pH 7, adding dichloromethane (100mL) to extract, combining the organic phases, drying over anhydrous magnesium sulfate, filtering, and removing the solvent under reduced pressure; the crude product was purified by silica gel column chromatography using n-heptane as a mobile phase to obtain intermediate IM 1-1(52.6g, yield 55%) as a white solid.

Intermediates IM 1-2 to IM 1-3 were prepared in the same manner as intermediate IM 1-1, except that the starting material bromobenzene in the preparation of intermediate IM 1-1 was replaced by starting material A in Table 1.

TABLE 1

2) Preparation of intermediate IM A-1

Reacting 5, 7-dihydro-indolo [2,3-B ]]Carbazole (20.0g, 78.03mmol), IM 1-1(22.72g, 78.03mmol), cuprous iodide (CuI) (2.97g, 15.60mmol), 1, 10-phenanthroline (5.62g, 31.18mmol), potassium carbonate K₂CO₃(23.72g, 171.67mmol) and 18-crown-6 (2.06g, 7.80mmol) are added into a three-neck flask, dried DMF (200mL) solvent is added, the temperature is raised to 150 ℃ under the protection of nitrogen, and the mixture is kept at the temperature and stirred for 18 hours; cooling to room temperature, stopping stirring, washing the reaction solution with water, separating an organic phase, drying with anhydrous magnesium sulfate, and removing the solvent under reduced pressure to obtain a crude product; purification by column chromatography on silica gel using dichloromethane/n-heptane as mobile phase gave the product, intermediate IM A-1, as a white solid (19.6g, 54% yield).

3) Preparation of Compound 1

A degassed nitrogen-substituted three-necked flask was charged with 55% sodium hydride NaH (0.92g, 21.4mmol), 100mL of dehydrated DMF, stirred under a stream of nitrogen and cooled to 0 ℃ and a solution of intermediate IM A-1(10.0g, 21.4mmol) in dehydrated DMF was added dropwise beginning at 0 ℃. Stirring for 1h after the dropwise addition is finished, and then dropwise adding 2-bromo-4, 6-diphenyl- [1,3,5] after the stirring is finished]Triazine (6.6g, 21.4mmol) in DMF. After the dropwise addition, stirring for 3h, adding water, and filteringWashing the precipitated crystal with ethanol, and filtering; the crude product was purified by silica gel column chromatography using dichloromethane/n-heptane as the mobile phase to give compound 1(6.4g, yield 43%) as a white solid, M/z-698.32 [ M + H ═]⁺。

Preparation examples 2 to 6

The following compounds were prepared in the same synthetic method as in preparation example 1 except that raw material B in table 2 was used instead of 2-bromo-4, 6-diphenyl- [1,3,5] triazine in preparation example 1 and intermediate C was used instead of intermediate IM 1-1 in preparation example 1. The main raw materials used, the compounds synthesized and their yields and mass spectrometry results are shown in table 2.

TABLE 2

Nuclear magnetic data for compound 11:

¹H-NMR(400MHZ,CD₂Cl₂):9.25(s,1H),8.95(s,1H),8.53-8.51(m,2H),8.30(d,1H),8.11(d,1H),7.98(d,1H),7.95(s,1H),7.72(d,1H),7.64-7.50(m,13H),7.45-7.40(m,4H),7.35-7.28(m,6H),2.20(s,3H),1.96(s,6H),1.84-1.74(m,6H).

preparation example 7 preparation of Compound 28

Compound 28 was prepared by the synthetic method described in preparation example 1, except that the starting material indolo [2,3-A ] was used]Carbazole (20g, 78.03mmol) was substituted for 5, 7-dihydro-indolo [2,3-B ] in preparation example 1]Carbazole to obtain compound 28(14.4g, 51% yield), M/z ═ 698.32[ M + H ═ 698.32]⁺。

¹H-NMR(400MHZ,CD₂Cl₂):8.93(d,1H),8.67-8.58(m,5H),8.13(d,1H),8.09(d,1H),7.95(d,1H),7.71(d,2H),7.58(m,6H),7.49(m,2H),7.34(m,3H),7.15(d,2H),2.19(s,3H),1.97(s,6H),1.81-1.75(m,6H).

Preparation examples 8 to 12

The following compounds were prepared in the same synthetic method as in preparation example 7, except that 2-bromo-4, 6-diphenyl- [1,3,5] triazine in preparation example 7 was replaced with the raw material D in table 3. The main raw materials used, the compounds synthesized and their yields and mass spectrometry results are shown in table 3.

TABLE 3

Nuclear magnetic data for compound 34:

¹H-NMR(400MHz,CD₂Cl₂):8.59-8.53(m,3H),8.35-8.31(m,3H),8.14(d,1H),8.09(d,1H),7.95-7.90(m,3H),7.58-7.44(m,11H),7.42-7.31(m,4H),7.26(d,2H),2.13(s,3H),1.94(s,6H),1.82-1.77(m,6H).

preparation examples 14 to 16

The following compounds were prepared in the same synthetic method as in preparation example 7 except that raw material E in table 4 was used instead of indolo [2,3-a ] carbazole in preparation example 7. The main raw materials used, the compounds synthesized and their yields and mass spectrometry results are shown in table 4.

TABLE 4

Nuclear magnetic data for compound 67:

¹H-NMR(400MHz,CD₂Cl₂):8.81-8.76(d,4H),8.53(d,1H),8.21(d,1H),8.14(d,1H),7.94-7.87(m,2H),7.68(d,2H),7.58-7.56(m,6H),7.41-7.33(m,4H),7.24(t,1H),7.18(d,2H),2.12(s,3H),1.93(s,6H),1.86-1.78(m,6H).

PREPARATION EXAMPLE 17 preparation of Compound 214

1. Preparation of intermediate IM B-1

1) Preparation of intermediate IM 1-a

2-bromocarbazole (30.0g, 121.8mmol), iodobenzene (24.8g, 78.03mmol), CuI (4.6g, 24.3mmol), and K₂CO₃Adding (37.0g, 268.1mmol), 1, 10-phenanthroline (8.7g, 48.72mmol) and 18-crown ether-6 (3.2g, 12.1mmol) into a three-neck flask, adding a dried DMF (300mL) solvent, heating to 150 ℃ under the protection of nitrogen, keeping the temperature and stirring for 17 hours; cooling to room temperature, stopping stirring, washing the reaction solution with water, separating an organic phase, drying with anhydrous magnesium sulfate, and removing the solvent under reduced pressure to obtain a crude product; purification by column chromatography on silica gel using dichloromethane/n-heptane as mobile phase gave the product intermediate IM 1-a as a white solid (26.3g, yield 67%).

2) Preparation of intermediate IM 1-b

Intermediate IM 1-a (26.0g, 80.6mmol), 2-chloroaniline (11.3g, 88.7mmol), Pd₂(dba)₃(0.73g, 0.8mmol), 2-dicyclohexyl phosphonium-2, 4, 6-triisopropyl biphenyl x-phos (0.76g, 1.6mmol) and sodium tert-butoxide (11.6g, 121.0mmol) are added into a three-neck flask, and toluene (300mL) solvent is added, and the temperature is raised to 110 ℃ under the protection of nitrogen, and the mixture is stirred for 15 hours while keeping the temperature; cooling to room temperature, stopping stirring, washing the reaction solution with water, separating an organic phase, drying with anhydrous magnesium sulfate, and removing the solvent under reduced pressure to obtain a crude product; purification by column chromatography on silica gel using dichloromethane/n-heptane as mobile phase gave the product intermediate IM 1-b as a white solid (15.7g, 53% yield).

3) Preparation of intermediate IM B-1

Intermediate IM 1-b (15.0g, 46.5mmol), cesium carbonate (37.9g, 116.3mmol), tricyclohexylfluorophosphoborate (8.5g, 23.2mmol), Pd (OAc)₂(0.5g, 2.3mmol), adding the mixture into a three-neck flask, adding a toluene (150mL) solvent, heating to 110 ℃ under the protection of nitrogen, keeping the temperature and stirring for 10 hours; cooling to room temperature, stopping stirring, washing the reaction solution with water, separating an organic phase, drying with anhydrous magnesium sulfate, and removing the solvent under reduced pressure to obtain a crude product; purification by column chromatography on silica gel using dichloromethane/n-heptane as the mobile phase gave the product, intermediate IM B-1, as a white solid (9.43g, yield)61％)。

2. Preparation of intermediate IM 2-1

1) Preparation of intermediate IM 2-a

2,4, 6-tribromo-1, 3, 5-triazine (30.0g, 94.4mmol), phenylboronic acid (13.8g, 113.2mmol), tetrakis (triphenylphosphine) palladium (5.4g, 4.7mmol), potassium carbonate (26.0g, 188.8mmol), tetrabutylammonium bromide (0.6g, 1.8mmol) were added to a three-necked flask, toluene (240mL), ethanol (120mL) and deionized water (60mL) were added to the three-necked flask, and the mixture was heated to 76 ℃ under nitrogen protection, heated to reflux and stirred for 18 h. Cooling to room temperature, stopping stirring, washing the reaction solution with water, separating an organic phase, drying with anhydrous magnesium sulfate, and removing the solvent under reduced pressure to obtain a crude product; purification by column chromatography on silica gel using dichloromethane/n-heptane as mobile phase gave the white intermediate IM 2-a (17.5g, 59% yield).

2) Preparation of intermediate IM 2-b:

adding the intermediate IM 1-1(35.0g, 120.1mmol) into a round-bottom flask, adding 630mL of THF into the flask after removing water, cooling the system to-80 to-90 ℃ by using liquid nitrogen, starting to dropwise add n-butyllithium (8.46g, 132.1mmol), and preserving heat for 1h after dropwise adding. Dropwise adding trimethyl borate (13.7g, 132.1mmol), keeping the temperature at-80 to-90 ℃, keeping the temperature for 1h, naturally heating to room temperature, adding HCl aqueous solution, and stirring for 0.5 h. Adding dichloromethane and water for liquid separation and extraction, washing the organic phase until the pH value is neutral to 7, combining the organic phases, and anhydrous MgSO₄After drying for 10min, filtration, spin-drying of the filtrate and beating with n-heptane 2 times gave intermediate IM 2-b as a white solid (20.9g, yield 68%).

3) Preparation of intermediate IM 2-1

IM 2-a (17.0g, 53.9mmol), IM 2-b (13.8g, 53.9mmol), tetrakis (triphenylphosphine) palladium (0.62g, 0.53mmol), potassium carbonate (14.9g, 107.9mmol), tetrabutylammonium bromide (0.34g, 1.1mmol) were added to a three-necked flask, toluene (140mL), ethanol (70mL) and deionized water (35mL) were added to the three-necked flask, the temperature was raised to 76 ℃ under nitrogen, and the mixture was stirred under reflux for 18 h. Cooling to room temperature, stopping stirring, washing the reaction solution with water, separating an organic phase, drying with anhydrous magnesium sulfate, and removing the solvent under reduced pressure to obtain a crude product; purification by column chromatography on silica gel using methylene chloride/n-heptane as a mobile phase gave the product IM 2-1 as a solid (14.9g, yield 62%).

An intermediate IM 2-I shown in the following table (I represents a variable and is an integer of 2-6) was synthesized in a similar manner to IM 2-1, except that the raw material F in Table 5 was used in place of the raw material phenylboronic acid in the synthesis method of IM 2-1. The starting materials used, the intermediate structures synthesized and the yield results are shown in table 5:

TABLE 5

4) Preparation of Compound 214

A degassed nitrogen-substituted three-necked flask was charged with 55% sodium hydride NaH (1.16g, 27.1mmol) and 100mL of dehydrated DMF, stirred under a stream of nitrogen, and cooled to 0 ℃ to begin dropping a solution of IM B-1(9.0g, 27.1mmol) in dehydrated DMF at 0 ℃. After the end of the addition, stirring was carried out for 1h, and after completion of the stirring, the addition of a DMF solution of IM 2-1(12.0g, 27.1mmol) was started. After the dropwise addition is finished, stirring for 3h, adding water, filtering to obtain precipitated crystals, washing with ethanol, and filtering; the crude product was purified by silica gel column chromatography using dichloromethane/n-heptane as the mobile phase to give compound 214(9.2g, yield 50%) as a white solid. 698.32[ M + H ] M/z]⁺。

¹H-NMR(400MHZ,CD₂Cl₂):9.05(s,1H),8.90(d,1H),8.82(m,2H),8.78(m,2H),8.11(d,1H),7.98(d,1H),7.95(s,1H),7.58-7.40(m,12H),7.32-7.24(m,3H),2.22(s,3H),1.93(s,6H),1.83-1.74(m,6H).

Preparation examples 18 to 30

Intermediates IM B-2 to IM B-15 shown in Table 6 below were synthesized in a similar manner to IM B-1 except that in the following table, raw material G was used instead of 2-bromocarbazole, raw material H was used instead of iodobenzene, and raw material I was used instead of 2-chloroaniline. The starting materials used, the intermediate structures synthesized and the yield results are shown in table 6:

TABLE 6

The compounds shown in Table 7 below were synthesized in a similar manner to preparation example 17 except that intermediates IM B-2 through IM B-15 (collectively referred to as "IM B-X") were used instead of intermediate IM B-1 and intermediate IM 2-X was used instead of intermediate IM 2-1. The intermediates, compound structures and their yields, mass spectrometry results used are shown in table 7:

TABLE 7

Nuclear magnetic data for compound 231:

¹H-NMR(400MHz,CD₂Cl₂):8.58-8.51(m,3H),8.36(d,1H),8.19(d,2H),8.15(d,1H),8.08(d,1H),7.95(d,1H),7.60-7.55(m,5H),7.53-7.31(m,10H),2.12(s,3H),1.95(s,6H),1.83-1.78(m,6H).

PREPARATION EXAMPLE 32 preparation of Compound 310

Compound 310 was prepared by the same synthetic method as in preparation example 1, except that 7H-benzofuran [2,3-B ] as a starting material was used]Carbazole (20.1g, 78.03mmol) was substituted for 5, 7-dihydro-indolo [2,3-B ] in preparation example 1]Carbazole to give compound 310(23.2g, 48% yield), M/z ═ 623.27[ M + H [ ]]⁺。

Preparation examples 33 to 39

The following compounds were prepared in the same synthetic method as in preparation example 32, except that raw material J of table 8 below was used instead of raw material 7H-benzofuran [2,3-B ] carbazole in preparation example 32. The raw materials used, the structures of the synthesized compounds and their yields, and the mass spectrometry results are shown in table 8:

TABLE 8

Preparation and evaluation of organic electroluminescent device

Example 1: green organic electroluminescent device

The anode was prepared by the following procedure: the thickness of ITO is set asThe ITO substrate of (1) was cut into a size of 40mm (length) × 40mm (width) × 0.7mm (thickness), prepared into an experimental substrate having an anode, a cathode overlapping region and an insulating layer pattern by a photolithography process, and used with ultraviolet ozone and O₂:N₂Plasma surface treatmentTo increase the work function of the anode. The surface of the ITO substrate can also be cleaned by adopting an organic solvent so as to remove impurities and oil stains on the surface of the ITO substrate.

A HAT-CN layer was vacuum-deposited on an experimental substrate (anode) to a thickness ofAnd NPB is vacuum-evaporated on the hole injection layer to form a layer having a thickness ofThe first hole transport layer of (1).

Vacuum evaporating TCBPA on the first hole transport layer to form a layer with a thickness ofThe second hole transport layer of (1).

Then, on the second hole transporting layer, Ir (npy) containing Compound 1 as a host₂acac as dopant. According to the proportion of 90%: co-evaporation is carried out at a ratio of 10% to form a film having a thickness ofGreen emitting layer (EML).

Then TPyQB and LiQ are mixed and evaporated to form the catalyst in a weight ratio of 1:1A thick Electron Transport Layer (ETL) formed by depositing Yb on the electron transport layerThen magnesium (Mg) and silver (Ag) were mixed at a rate of 1:9, and vacuum-evaporated on the electron injection layer to form an Electron Injection Layer (EIL) having a thickness ofThe cathode of (1).

The thickness of the vacuum deposition on the cathode is set toThereby completing the fabrication of the organic electroluminescent device.

Examples 2 to 39

An organic electroluminescent device was produced in the same manner as in example 1, except that the mixed components shown in table 9 were used instead of the mixed components in example 1 in forming the light-emitting layer.

Comparative examples 1 to 3

An organic electroluminescent device was fabricated by the same method as example 1, except that the mixed component of compound A, B, C shown in the following table was substituted for the mixed component in example 1 in forming the light-emitting layer.

When the organic electroluminescent device is prepared, the material structures used in comparative examples 1 to 3 and examples 1 to 39 are as follows:

performance tests were performed on the green organic electroluminescent devices prepared in examples 1 to 39 and comparative examples 1 to 3, specifically at 10mA/cm²The IVL performance of the device is tested under the condition of (1), and the service life of the T95 device is 20mA/cm²The test was performed under the conditions of (1), and the test results are shown in table 9.

Table 9 performance test results of green organic electroluminescent device

As shown in the results of device performance tests in Table 9, the compounds of the present invention used as the host materials of the green light emitting layers in examples 1-39 showed improved device efficiencies and T95 lifetimes compared to comparative examples 1-3, with substantially equivalent driving voltages; the device efficiency is improved by at least 19.6%, and the service life is improved by at least 14.1%.

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

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

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

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

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