阅读说明：本技术 有机化合物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 陈志伟 薛震 王金平 于 2021-09-17 设计创作，主要内容包括：本申请涉及有机材料技术领域,具体涉及一种有机化合物,该有机化合物以氮杂菲环为母核,在母核上引入共轭连接的不对称的芳香性基团,使化合物偶极矩提高,分子极性提高,进而电子传输性能提高。该化合物可用作电子传输层或有机发光层主体材料,能够显著提升有机电致发光器件的效率和使用寿命。(The application relates to the technical field of organic materials, in particular to an organic compound, wherein an azaphenanthrene ring is used as a mother nucleus, and asymmetric aromatic groups in conjugate connection are introduced into the mother nucleus, so that the dipole moment of the compound is improved, the molecular polarity is improved, and the electron transmission performance is improved. The compound can be used as a main body material of an electron transport layer or an organic light-emitting layer, and can remarkably improve the efficiency and the service life of an organic electroluminescent device.)

1. An organic compound having a structure represented by the following formula 1:

wherein, X₁、X₂、X₃And X₄Each independently selected from C, C (H) or N, and X₁、X₂、X₃And X₄One or two of them are N;

R₁selected from substituted or unsubstituted aryl with 6-30 carbon atoms and substituted or unsubstituted 5-13 membered heteroaryl;

R₂and R₃The same or different, and each is independently selected from hydrogen, substituted or unsubstituted aryl with 6-30 carbon atoms, substituted or unsubstituted 5-13 membered heteroaryl or a group shown in a formula 2; and R is₂And R₃At least one of them is selected from the structures represented by formula 2;

and isAnd R₃Different;

L₁selected from substituted or unsubstituted arylene groups having 6 to 30 carbon atoms, and substituted or unsubstituted 5-to 13-membered heteroarylene groups;

L₀and L₂Each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, a substituted or unsubstituted 5-13 membered heteroarylene group;

Z₁selected from substituted or unsubstituted aryl with 6-30 carbon atoms, substituted or unsubstituted 5-13 membered heteroaryl, triphenyl silyl and diaryl phosphonyl;

R₁、R₂、R₃、L₀、L₁、L₂and Z₁Wherein the substituents are the same or different and are each independently selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, a carbon atomAlkoxy with a sub-number of 1-10, cycloalkyl with a sub-number of 3-10, aryl with a sub-number of 6-20 optionally substituted by alkyl with a sub-number of 1-4, heteroaryl with a sub-number of 5-13, trialkylsilyl with a sub-number of 3-12;

optionally, at R₁、R₂、R₃、L₀、L₁、L₂And Z₁Wherein any two adjacent substituents are linked to each other to form a 5-to 10-membered alicyclic ring.

2. The organic compound according to claim 1, wherein the organic compound has a structure represented by any one of the following formulas 1-1 to 1-6:

3. the organic compound of claim 1, wherein R₁Selected from substituted or unsubstituted aryl with 6-18 carbon atoms and substituted or unsubstituted 6-13 membered heteroaryl;

alternatively, R₁Wherein the substituent is selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 5 carbon atoms, a cycloalkyl group having 5 to 10 carbon atoms, an aryl group having 6 to 12 carbon atoms or a 5-to 10-membered heteroaryl group; optionally, R₁Any two adjacent substituents of which are linked to each other to form a 5-6 membered alicyclic ring.

4. The organic compound of claim 1, wherein R₁Selected from the group consisting of substituted or unsubstituted groups X, the unsubstituted groups X being selected from the group consisting of:

wherein the content of the first and second substances,represents a chemical bond; said substituted group X having one or more substituents thereon, each of said substituents being independently selected from deuterium, fluoro, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, cyclopentyl, phenyl, trifluoromethyl, naphthyl or pyridyl; when there are multiple substituents on the substituted group X, the substituents may be the same or different.

5. The organic compound of claim 1, wherein R is₂And R₃The same or different, and each is independently selected from hydrogen, substituted or unsubstituted aryl with 6-18 carbon atoms, substituted or unsubstituted 6-13 membered heteroaryl or a group shown in a formula 2; and R is₂And R₃At least one of them is selected from the group represented by formula 2;

alternatively, the R is₂And R₃Wherein the substituents are independently selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 5 carbon atoms, a cycloalkyl group having 5 to 10 carbon atoms, an aryl group having 6 to 12 carbon atoms, a 6-to 13-membered heteroaryl group, a haloalkyl group having 1 to 5 carbon atoms, and a trialkylsilyl group having 3 to 7 carbon atoms.

6. The organic compound of claim 1, wherein R is₂And R₃Are identical or different and are each independently selected from hydrogen, substituted or unsubstituted radicals Y or radicals of the formula 2, and R₂And R₃At least one of them is selected from the group represented by formula 2; wherein the unsubstituted group Y is selected from the group consisting of:

wherein the content of the first and second substances,represents a chemical bond; one or more substituents on the substituted group Y;

the substituents on the group Y are each independently selected from deuterium, fluorine, cyano, alkyl having 1 to 5 carbon atoms, cycloalkyl having 5 to 10 carbon atoms, aryl having 6 to 12 carbon atoms, 6-13 membered heteroaryl, trifluoromethyl or trimethylsilyl;

alternatively, the substituents on the group Y are each independently selected from deuterium, fluoro, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, cyclopentyl, phenyl, naphthyl, pyridyl, trifluoromethyl, trimethylsilyl, quinazolinyl, pyrimidinyl, dibenzothienyl, dibenzofuranyl, or benzoxazolyl; when there are multiple substituents on the substituted group Y, the substituents may be the same or different.

7. The organic compound of claim 1, wherein said L₁Selected from substituted or unsubstituted groups V₁Unsubstituted radicals V₁Selected from the group consisting of:

wherein the content of the first and second substances,represents a chemical bond; the substituted group V₁Having one or more substituents thereon, each of said substituents being independently selected from deuterium, fluoro, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, cyclopentyl, phenyl, naphthyl, biphenyl, dibenzofuranyl, dibenzothiophenyl, 9-dimethylfluorenyl; when said substituted group V₁When there are a plurality of substituents, the substituents may be the same or different.

8. The organic compound of claim 1, wherein said L₀And L₂Each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, a substituted or unsubstituted 5-13 membered heteroarylene group;

optionally, said L₀And L₂Wherein the substituents are independently selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 5 carbon atoms, a cycloalkyl group having 5 to 10 carbon atoms, and an aryl group having 6 to 12 carbon atoms.

9. The organic compound of claim 1, wherein said L₀Selected from single bonds, substituted or unsubstituted groups V₂Unsubstituted radicals V₂Selected from the group consisting of:

wherein the content of the first and second substances,represents a chemical bond; the substituted group V₂Having one or more substituents thereon, each of said substituents being independently selected from deuterium, fluoro, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, cyclopentyl, phenyl or naphthyl; when said substituted group V₂When there are a plurality of substituents, the substituents may be the same or different.

10. The organic compound of claim 1, wherein said L₂Selected from single bonds, substituted or unsubstituted groups V₃Unsubstituted radicals V₃Selected from the group consisting of:

wherein the content of the first and second substances,represents a chemical bond; the substituted group V₃Having one or more substituents thereon, each of said substituents being independently selected from deuterium, fluoro, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, cyclopentyl, biphenyl, phenyl, naphthyl; when said substituted group V₃When there are a plurality of substituents, the substituents may be the same or different.

11. The organic compound of claim 1, wherein Z is₁Selected from substituted or unsubstituted aryl with 6-18 carbon atoms, substituted or unsubstituted 5-13 membered heteroaryl, diaryl phosphonyl and triphenyl silicon base;

optionally, Z is₁Wherein the substituents are independently selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 5 carbon atoms, a cycloalkyl group having 5 to 10 carbon atoms, and an aryl group having 6 to 12 carbon atoms.

12. The organic compound of claim 1, wherein Z is₁Selected 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,represents a chemical bond; said substituted group W having one or more substituents thereon, each of said substituents being independently selected from deuterium, fluoro, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, cyclopentyl, phenyl; when there are a plurality of substituents on the substituted group W, the substituents may be the same or different.

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

14. 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 an organic compound according to any one of claims 1 to 13;

optionally, the functional layer comprises an electron transport layer comprising the organic compound;

optionally, the functional layer comprises an organic light emitting layer comprising the organic compound.

15. The electronic element according to claim 14, wherein the electronic element is an organic electroluminescent device;

optionally, the organic electroluminescent device is a blue organic electroluminescent device or a red organic electroluminescent device.

16. An electronic device, characterized by comprising the electronic component of claim 14 or 15.

Technical Field

The present disclosure relates to the field of organic electroluminescence technologies, and in particular, to an organic compound, and an electronic element and an electronic device using the organic compound.

Background

An organic light-emitting diode (OLED), which is abbreviated as OLED, is based on the principle that when an electric field is applied between a cathode and an anode, a hole on an anode side and an electron on a cathode side move to a light-emitting layer, and combine to form an exciton in the light-emitting layer, the exciton is in an excited state and releases energy outwards, and the process of releasing energy from the excited state to a ground state releases energy emits light outwards. Since Kodak corporation reports electroluminescence of organic molecules in 1987 and Cambridge university in England reports electroluminescence of polymers in 1990, various countries in the world have developed research and development. The material has the advantages of simple structure, high yield, low cost, active luminescence, high response speed, high fraction and the like, has the performances of low working voltage, all solid state, no vacuum, oscillation resistance, low temperature resistance (-40 ℃) and the like, is considered as a new technology which is most likely to replace a liquid crystal display in the future, and draws great attention.

In the conventional organic electroluminescent device, the most important problems are lifetime and efficiency, and as the area of the display increases, the operating voltage increases and the luminous efficiency and current efficiency also increase, so that it is necessary to continuously develop a more stable host material with high performance to further improve the performance of the organic electroluminescent device.

Disclosure of Invention

An object of the present application is to provide an organic compound, and an electronic component and an electronic device using the same, which have high luminous efficiency and long life.

In order to achieve the above object, a first aspect of the present disclosure provides an organic compound having a group represented by the following formula 1:

wherein, X₁、X₂、X₃And X₄Each independently selected from C, C (H) or N, and X₁、X₂、X₃And X₄One or two of them are N;

R₁selected from substituted or unsubstituted aryl with 6-30 carbon atoms and substituted or unsubstituted 5-13 membered heteroaryl;

R₂and R₃The same or different, and each is independently selected from hydrogen, substituted or unsubstituted aryl with 6-30 carbon atoms, and substituted or unsubstituted arylA 5-13 membered heteroaryl group or a group of formula 2; and R is₂And R₃At least one of them is selected from the group represented by formula 2;

and isAnd R₃Different;

L₁selected from substituted or unsubstituted arylene groups having 6 to 30 carbon atoms, and substituted or unsubstituted 5-to 13-membered heteroarylene groups;

L₀and L₂Each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, a substituted or unsubstituted 5-to 13-membered heteroarylene group;

Z₁selected from substituted or unsubstituted aryl with 6-30 carbon atoms, substituted or unsubstituted 5-13 membered heteroaryl, triphenyl silyl and diaryl phosphonyl;

R₁、R₂、R₃、L₀、L₁、L₂and Z₁Wherein the substituents are the same or different and are each independently selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms optionally substituted with an alkyl group having 1 to 4 carbon atoms, a 5-13 membered heteroaryl group, a trialkylsilyl group having 3 to 12 carbon atoms;

optionally, at R₁、R₂、R₃、L₀、L₁、L₂And Z₁Wherein any two adjacent substituents are linked to each other to form a 5-to 10-membered alicyclic ring.

A second aspect of the present disclosure 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 disclosure;

optionally, the functional layer comprises an electron transport layer comprising the organic compound;

optionally, the functional layer comprises an organic light emitting layer comprising the organic compound.

A third aspect of the present disclosure provides an electronic device including the electronic component according to the second aspect of the present disclosure.

By adopting the technical scheme, the organic compound provided by the disclosure takes the nitrogen-containing heteroaryl of benzene rings on two sides as a mother nucleus, and at least two asymmetric aromatic groups in conjugate connection are introduced into the mother nucleus, so that the dipole moment of the compound is improved, the molecular polarity is improved, the electron mobility is improved, the 2-bit aromatic group is connected to the mother nucleus, the electron mobility is further improved, and the triplet state energy level of the compound can be adjusted, so that the electron mobility is improved; meanwhile, the aromatic group connected by the delta bond has high rotational freedom degree, and the compound has good three-dimensional property and good film forming property. At least two groups of aromatic groups connected with the parent nucleus expand a carrier transmission area and improve the carrier migration of the compound. The compound structure is asymmetric, has an obvious bipolar structure, has high triplet state energy level, can be used as a main body material of an electron transport layer or an organic light-emitting layer, and can remarkably improve the efficiency and prolong the service life of an organic electroluminescent device.

Additional features and advantages of the disclosure will be set forth in the detailed description which follows.

Drawings

The accompanying drawings, which are included to provide a further understanding of the disclosure and are incorporated in and constitute a part of this specification, illustrate embodiments of the disclosure and together with the description serve to explain the disclosure without limiting the disclosure. In the drawings:

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

Fig. 2 is a schematic structural view of a photoelectric conversion device according to an embodiment of the present application.

Fig. 3 is a schematic structural diagram of a first electronic device according to an embodiment of the present application.

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

Description of the reference numerals

100. An anode; 200. a cathode; 300. a functional layer; 310. a hole injection layer; 320: a hole transport layer; 321. a first hole transport layer; 322. a second hole transport layer; 330. an organic light emitting layer; 340. an electron transport layer; 350. an electron injection layer; 360. a photoelectric conversion layer; 400. a first electronic device; 500. a second 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.

The present disclosure provides, in a first aspect, an organic compound having a group represented by formula 1 below:

wherein, X₁、X₂、X₃And X₄Each independently selected from C, C (H) or N, and X₁、X₂、X₃And X₄One or two of them are N;

R₁selected from substituted or unsubstituted aryl with 6-30 carbon atoms and substituted or unsubstituted 5-13 membered heteroaryl;

R₂and R₃The same or different, and each is independently selected from hydrogen, substituted or unsubstituted aryl with 6-30 carbon atoms, substituted or unsubstituted 5-13 membered heteroaryl or a group shown in a formula 2; and R is₂And R₃At least one of them is selected from the structures represented by formula 2;

and isAnd R₃Different;

L₁selected from substituted or unsubstituted arylene groups having 6 to 30 carbon atoms, and substituted or unsubstituted 5-to 13-membered heteroarylene groups;

L₀and L₂Each independently selected fromA bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, a substituted or unsubstituted 5-to 13-membered heteroarylene group;

Z₁selected from substituted or unsubstituted aryl with 6-30 carbon atoms, substituted or unsubstituted 5-13 membered heteroaryl, triphenyl silyl and diaryl phosphonyl;

R₁、R₂、R₃、L₀、L₁、L₂and Z₁Wherein the substituents are the same or different and are each independently selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms optionally substituted with an alkyl group having 1 to 4 carbon atoms, a 5-13 membered heteroaryl group, a trialkylsilyl group having 3 to 12 carbon atoms;

optionally, at R₁、R₂、R₃、L₀、L₁、L₂And Z₁Wherein any two adjacent substituents are linked to each other to form a 5-to 10-membered alicyclic ring.

In the formula 1, ` X `₁、X₂、X₃And X₄Is selected from the group consisting of C "and the C atom is R₃The carbon atom to which it is attached.

In this application, R₁、R₂、R₃、L₀、L₁、L₂And Z₁The number of carbon atoms selected from the group consisting of "substituted or unsubstituted aryl (ene) groups having 6 to 30 carbon atoms" means all the number of carbon atoms. For example, if L₁Selected from substituted arylene groups having 10 carbon atoms, the sum of all carbon atoms of the arylene group and the substituents thereon is 10. For example, if R₁Is 9, 9-dimethylfluorenyl, then R₁Is a substituted fluorenyl group having 15 carbon atoms, R₁The number of ring-forming carbon atoms of (2) is 13.

The descriptions used in this application that "… … independently" and "… … independently" and "… … independently selected from" are interchangeable and should be understood in a broad sense to mean that the particular items expressed between the same symbols do not interfere with each other in different groups or that the particular items expressed between the same symbols do not interfere with each other in the same groups.

For example: in "Wherein each q is independently 0, 1,2 or 3, and each R "is independently selected from the group consisting of hydrogen, 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, when a specific definition is not otherwise provided, "hetero" means that at least 1 hetero atom of B, N, O, S, Se, Si, or P, etc. is included in one functional group and the remaining atoms are carbon and hydrogen.

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. For example, "substituted or unsubstituted aryl" refers to an aryl group having a substituent or an unsubstituted aryl group. "substituted" means that it may be substituted with a substituent selected from the group consisting of: deuterium, a halogen group, a cyano group, an alkyl group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms optionally substituted with an alkyl group having 1 to 4 carbon atoms, a 5-13 membered heteroaryl group, a trialkylsilyl group having 3 to 12 carbon atoms, and the like.

The terms "optional" or "optionally" mean that the subsequently described event or circumstance may or may not occur. For example, "aryl optionally substituted with alkyl"means that an alkyl group may or may not be present, and the description includes the case where an aryl group is substituted with an alkyl group and the case where an aryl group is not substituted with an alkyl group. "optionally, R is attached to the same atom_v2And R_v3Linked to each other to form a saturated or unsaturated ring ", meaning that R is attached to the same atom_v2And R_v3Can form a ring but does not have to form a ring, and the scheme comprises R_v2And R_v3The scenario of interconnecting to form a ring, also including R_v2And R_v3Scenarios that exist independently of each other.

The "ring" in the present application includes saturated rings as well as unsaturated rings; saturated rings, i.e., cycloalkyl, heterocycloalkyl; unsaturated rings, i.e., cycloalkenyl, heterocycloalkenyl, aryl, and heteroaryl. In the present application, an aliphatic ring refers to a cycloalkyl group.

In the present application, "any two adjacent substituents are linked to each other to form a 5-to 10-membered alicyclic ring", means: two substituents attached to the same atom are attached to each other to form a 5-to 10-membered alicyclic ring together with the atom to which they are attached in common, or two substituents attached to two adjacent atoms are attached to each other to form a 5-to 10-membered alicyclic ring together with the atom to which they are attached respectively.

In the present application, "alkyl" may include straight chain alkyl or branched alkyl. Alkyl groups may have 1 to 10 carbon atoms, and numerical ranges such as "1 to 10" refer herein to each integer in the given range; for example, "1 to 10 carbon atoms" refers to an alkyl group that may contain 1,2, 3,4, 5, 6, 7, 8, 9, 10. In some embodiments, the alkyl group contains 1 to 5 carbon atoms; in still other embodiments, the alkyl group contains 1 to 3 carbon atoms. The alkyl group may be optionally substituted with one or more substituents described herein. Examples of alkyl groups having 1 to 5 carbon atoms include, but are not limited to, methyl (Me, -CH)₃) Ethyl group (Et, -CH)₂CH₃) N-propyl (n-Pr, -CH)₂CH₂CH₃) Isopropyl group (i-Pr, -CH (CH)₃)₂) N-butyl (n-Bu, -CH)₂CH₂CH₂CH₃)，Isobutyl (i-Bu, -CH)₂CH(CH₃)₂) Sec-butyl (s-Bu, -CH (CH)₃)CH₂CH₃) Tert-butyl (t-Bu, -C (CH)₃)₃) And a pentyl group. Further, the alkyl group may be substituted or unsubstituted.

In this application, cycloalkyl refers to cyclic saturated hydrocarbons, including monocyclic and polycyclic structures. Cycloalkyl groups may have 3-10 carbon atoms, for example, "3 to 10 carbon atoms" refers to cycloalkyl groups that may contain 3,4, 5, 6, 7, 8, 9,10 carbon atoms. In addition, cycloalkyl groups may be substituted or unsubstituted. In some embodiments, cycloalkyl is a cycloalkyl group having 5 to 10 carbon atoms, in other embodiments, a cycloalkyl group having 5 to 8 carbon atoms, and examples of cycloalkyl groups may be, but are not limited to: 5-membered cycloalkyl (cyclopentyl), 6-membered cycloalkyl (cyclohexyl), 10-membered polycycloalkyl (e.g., adamantyl), and the like.

In the present application, aryl refers to an optional functional group or substituent derived from an aromatic hydrocarbon ring. The aryl group may be a monocyclic aryl group or a polycyclic aryl group, in other words, the aryl group may be a monocyclic aryl group, a fused ring aryl group, two or more monocyclic aryl groups connected by carbon-carbon bond conjugation, a monocyclic aryl group and a fused ring aryl group connected by carbon-carbon bond conjugation, two or more fused ring aryl groups connected by carbon-carbon bond conjugation. That is, two or more aromatic groups conjugated through a carbon-carbon bond may also be considered as an aryl group in the present application. Wherein the aryl group does not contain a hetero atom such as B, N, O, S, Se, Si or P. Examples of the aryl group may include phenyl, naphthyl, fluorenyl, anthracenyl, phenanthrenyl, biphenyl, terphenyl, quaterphenyl, benzo [9,10 ]]Phenanthryl, pyrenyl, perylenyl, benzofluoranthenyl, pyrenyl, perylene,A group, 9 dimethylfluorenyl group, 9 diphenylfluorenyl group, spirobifluorenyl group, indenyl group, etc., without being limited thereto. As used herein, a "substituted or unsubstituted aryl" group may contain from 6 to 30 carbon atoms, and in some embodiments the number of carbon atoms in a substituted or unsubstituted aryl group may be from 6 to 25, and in other embodiments, substitutedOr unsubstituted aryl groups may have from 6 to 18 carbon atoms, and in other embodiments, substituted or unsubstituted aryl groups may have from 6 to 13 carbon atoms. In the present application, the number of carbon atoms of the substituted or unsubstituted aryl group may be 6, 10, 12, 13, 14, 15, 16, 18, 20, 25, 26 or 30, and of course, the number of carbon atoms may be other numbers, which are not listed herein.

In this application, substituted aryl refers to an aryl group in which one or more hydrogen atoms are replaced with another group. For example, at least one hydrogen atom is substituted with a deuterium atom, F, Cl, I, -CN, hydroxyl, branched alkyl, linear alkyl, haloalkyl, deuterated alkyl, trialkylsilyl, cycloalkyl, alkoxy, aryl, heteroaryl, trialkylsilyl, or other group. It is understood that the number of carbon atoms of the substituted aryl group refers to the total number of carbon atoms of the aryl group and the substituents on the aryl group. For example, a substituted aryl group having 18 carbon atoms means that the total number of carbon atoms of the aryl group and the substituent on the aryl group is 18. For example, 9, 9-dimethylfluorenyl is a substituted aryl group having 15 carbon atoms.

In the present application, the fluorenyl group as the aryl group may be substituted, and when two substituents are present on the fluorenyl group, optionally, the two substituents may be combined with each other to form a spiro structure, and specific examples include, but are not limited to, the following structures:

in the present application, "an aryl group having 6 to 20 carbon atoms optionally substituted with an alkyl group having 1 to 4 carbon atoms" means an aryl group having 6 to 20 carbon atoms in total substituted with an alkyl group having 1 to 4 carbon atoms or an unsubstituted aryl group having 6 to 20 carbon atoms.

Examples of the aryl group as a substituent in the present application include, but are not limited to, phenyl, naphthyl, anthryl, phenanthryl, biphenyl, fluorenyl and dimethylfluorenyl.

In this application, heteroaryl refers to a monocyclic or polycyclic ring system containing 1,2, 3,4, 5, 6, or 7 heteroatoms in the ring independently selected from O, N, P, Si, Se, B, and S, and wherein at least one ring system is aromatic. 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, any one of the aromatic ring systems is an aromatic monocyclic ring or an aromatic fused ring, and any one of the aromatic ring systems contains the heteroatom. Illustratively, heteroaryl groups may include thienyl, furyl, pyrrolyl, imidazolyl, thiazolyl, oxazolyl, isothiazolyl, oxadiazolyl, triazolyl, oxazolyl, furazanyl, pyridyl, bipyridyl, phenanthridinyl, pyrimidinyl, triazinyl, acridinyl, pyridazinyl, pyrazinyl, quinolyl, quinazolinyl, quinoxalinyl, phenoxazinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, isoquinolyl, indolyl, carbazolyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothienyl, dibenzothienyl, thienothienyl, benzofuranyl, phenanthrolinyl, isoxazolyl, thiadiazolyl, benzothiazolyl, phenothiazinyl, silafluorenyl, dibenzofuranyl, N-phenylcarbazolyl, N-pyridylcarbazolyl, N-methylcarbazolyl, and the like, and is not limited thereto.

In this application, the ring system formed by n atoms is an n-membered ring. For example, phenyl is a 6-membered aryl. Pyridyl is 6-membered heteroaryl.

In the present application, substituted or unsubstituted heteroaryl refers to substituted or unsubstituted heteroaryl having 5 to 13 ring atoms. In some embodiments, substituted or unsubstituted heteroaryl is substituted or unsubstituted 5-13 membered heteroaryl, and in other embodiments, substituted or unsubstituted heteroaryl is substituted or unsubstituted 6-13 membered heteroaryl.

In the present application, 5-13 membered heteroaryl means heteroaryl having 5-13 ring atoms. For example, but not limited to, furyl, thienyl, imidazolyl, pyridyl, pyrimidinyl, triazinyl, pyridazinyl, pyrazinyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, quinolinyl, quinazolinyl, quinoxalinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, isoquinolinyl, benzimidazolyl, benzothiazolyl, dibenzothienyl, dibenzofuryl, carbazolyl, azabicycloheptanyl, azabenzothienyl, oxadiazolyl, and the like. Further, the 5-13 membered heteroaryl group includes a 5-membered heteroaryl group, a 6-membered heteroaryl group, a 7-membered heteroaryl group, an 8-membered heteroaryl group, a 9-membered heteroaryl group, a 10-membered heteroaryl group, an 11-membered heteroaryl group, a 12-membered heteroaryl group and a 13-membered heteroaryl group.

In the present application, "substituted or unsubstituted 5-13 membered heteroaryl" refers to 5-13 membered heteroaryl having a substituent or unsubstituted 5-13 membered heteroaryl; the substituent on the 5-13 membered heteroaryl is selected from deuterium, a halogen group, a cyano group, an alkyl group having 1-10 carbon atoms, a haloalkyl group having 1-10 carbon atoms, an alkoxy group having 1-10 carbon atoms, a cycloalkyl group having 3-10 carbon atoms, an aryl group having 6-20 carbon atoms optionally substituted with an alkyl group having 1-4 carbon atoms, a 5-13 membered heteroaryl group, and a trialkylsilyl group having 3-12 carbon atoms.

In the present application, heteroaryl as a substituent is exemplified by, but not limited to, pyridyl, pyrimidinyl, quinolyl, dibenzothienyl, dibenzofuranyl, benzopyrimidinyl, isoquinolyl, carbazolyl, quinolyl, benzothiazolyl, benzoxazolyl.

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

In the present application, trialkylsilyl meansWherein R is^G1、R^G2、R^G3Specific examples of the trialkylsilyl group, each independently an alkyl group, include, but are not limited to, trimethylsilyl, triethylsilyl, t-butyldimethylsilyl, and propyldimethylsilyl.

An delocalized bond in the present application 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 the 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) comprises any possible connecting mode shown in the formula (f-10).

As another example, as shown in the following formula (X '), the carbazolyl group represented by formula (X') is bonded to another position of the molecule through an delocalized bond extending from the middle of the benzene ring on one side, and the meaning thereof includes any of the possible bonding modes as shown in formulas (X '-1) to (X' -5).

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, in the following formula (Y), the substituent R group 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 shown by the formulas (Y-1) to (Y-7).

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

In the present application, the number of carbon atoms of the haloalkyl group having 1 to 10 carbon atoms may be, for example, 1,2, 3,4, 5, 6, 7, 8, 9,10, including but not limited to trifluoromethyl and the like.

In the present application, the alkoxy group having 1 to 10 carbon atoms may be a chain, cyclic or branched alkoxy group. The number of carbon atoms can be, for example, 1,2, 3,4, 5, 6, 7, 8, 9,10, including but not limited to methoxy, isopropoxy, and the like.

In the present application, the number of carbon atoms of the trialkylsilyl group having 3 to 12 carbon atoms may be, for example, 3,4, 5, 6, 7, 8, 9,10, 11, 12 carbon atoms, including but not limited to trimethylsilyl and the like.

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

In the present application, the substituted or unsubstituted aryl group having 6 to 30 carbon atoms may be selected from, for example, the following substituted or unsubstituted groups: phenyl, naphthyl, biphenyl, terphenyl, fluorenyl, anthracenyl, phenanthrenyl, perylenyl, pyrenyl, and the like.

In some embodiments of the present application, formula 1 is selected from the group consisting of structures represented by any one of formulae 1-1 to formulae 1-6 below:

in some embodiments of the present application, R₁Selected from substituted or unsubstituted aryl with 6-18 carbon atoms and substituted or unsubstituted 6-13 membered heteroaryl.

Alternatively, R₁Wherein the substituent is selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 5 carbon atoms, a cycloalkyl group having 5 to 10 carbon atoms, an aryl group having 6 to 12 carbon atoms or a 5-to 10-membered heteroaryl group; optionally, R₁Any two adjacent substituents of which are linked to each other to form a 5-6 membered alicyclic ring.

In some embodiments of the present application, R₁Selected from substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstitutedSubstituted terphenyl group, substituted or unsubstituted naphthyl group, substituted or unsubstituted phenanthryl group, substituted or unsubstituted dibenzothienyl group, substituted or unsubstituted dibenzofuranyl group, substituted or unsubstituted benzoxazolyl group, substituted or unsubstituted benzothiazolyl group, substituted or unsubstituted triphenylene group, substituted or unsubstituted fluorenyl group, substituted or unsubstituted carbazolyl group, substituted or unsubstituted pyridyl group, substituted or unsubstituted benzothiophenyl group, substituted or unsubstituted pyrimidyl group, substituted or unsubstituted quinolyl group, substituted or unsubstituted spiro [ cyclopentane-1, 9' -fluorenyl group]。

Alternatively, R₁Each substituent in (a) is independently selected from deuterium, fluoro, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, cyclopentyl, phenyl, trifluoromethyl, naphthyl or pyridyl.

In some embodiments of the present application, R₁Selected from the group consisting of substituted or unsubstituted groups X, the unsubstituted groups X being selected from the group consisting of:

wherein the content of the first and second substances,represents a chemical bond; said substituted group X having one or more substituents thereon, each of said substituents being independently selected from deuterium, fluoro, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, cyclopentyl, phenyl, trifluoromethyl, naphthyl or pyridyl; when there are multiple substituents on the substituted group X, the substituents may be the same or different.

In some embodiments of the present application, R₁Selected from the group consisting of:

in some embodiments of the present application, R₂And R₃The same or different, and each is independently selected from hydrogen, substituted or unsubstituted aryl with 6-18 carbon atoms, substituted or unsubstituted 6-13 membered heteroaryl or a group shown in a formula 2; and R is₂And R₃At least one of them is selected from the group represented by formula 2.

Alternatively, the R is₂And R₃Wherein the substituents are independently selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 5 carbon atoms, a cycloalkyl group having 5 to 10 carbon atoms, an aryl group having 6 to 12 carbon atoms, a 6-to 13-membered heteroaryl group, a haloalkyl group having 1 to 5 carbon atoms, and a trialkylsilyl group having 3 to 7 carbon atoms.

In some embodiments of the present application, R₂And R₃The substituents are the same or different and are each independently selected from hydrogen, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted quinolyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted pyridyl, substituted or unsubstituted dibenzothienyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted group of formula A, group of formula 2; and R is₂And R₃At least one of them is selected from the group represented by formula 2;

alternatively, R₂And R₃Wherein the substituents are independently selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 5 carbon atoms, a cycloalkyl group having 5 to 10 carbon atoms, an aryl group having 6 to 12 carbon atoms, a 6-to 13-membered heteroaryl group, a haloalkyl group having 1 to 5 carbon atoms, and a trialkylsilyl group having 3 to 12 carbon atoms.

In one embodiment, R₃Is not hydrogen.

In one embodiment, R₂Is hydrogen.

In some embodiments of the present application, R₂And R₃The same or different, and the like,and each is independently selected from hydrogen, a substituted or unsubstituted group Y or a group of formula 2, and R₂And R₃At least one of them is selected from the group represented by formula 2; the unsubstituted group Y is selected from the group consisting of:

wherein the content of the first and second substances,represents a chemical bond; one or more substituents on the substituted group Y;

alternatively, the substituents on the group Y are each independently selected from deuterium, fluoro, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, cyclopentyl, phenyl, naphthyl, pyridyl, trifluoromethyl, trimethylsilyl, quinazolinyl, pyrimidinyl, dibenzothienyl, dibenzofuranyl, or benzoxazolyl; when there are multiple substituents on the substituted group Y, the substituents may be the same or different.

Alternatively, the substituents on the group Y are each independently selected from deuterium, fluorine, cyano, alkyl of 1 to 5 carbon atoms, cycloalkyl of 5 to 10 carbon atoms, aryl of 6 to 12 carbon atoms, 6-13 membered heteroaryl, trifluoromethyl or trimethylsilyl.

In some embodiments of the present application, R₂And R₃Are the same or different and are each independently selected from hydrogen, a group represented by formula 2, or a group consisting of:

in some embodiments of the present application, R₂And R₃Are not identical.

In some embodiments of the present application, L₁Selected from substituted or unsubstituted arylene with 6-26 carbon atoms and substituted or unsubstituted 5-13 membered heteroarylene.

Optionally, said L₁Wherein the substituents are each independently selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 5 carbon atoms, a cycloalkyl group having 3 to 5 carbon atoms, an aryl group having 6 to 15 carbon atoms optionally substituted with an alkyl group having 1 to 4 carbon atoms, and a 6-to 13-membered heteroaryl group.

In some embodiments of the present application, L₁Selected from the group consisting of substituted or unsubstituted phenylene, substituted or unsubstituted biphenylene, substituted or unsubstituted anthrylene, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzothiophenylene, substituted or unsubstituted dibenzofuranylene, substituted or unsubstituted phenanthrylene, substituted or unsubstituted triazinylene, substituted or unsubstituted pyrimidinylene, substituted or unsubstituted benzothiazolyl, substituted or unsubstituted quinazolinylene, and substituted or unsubstituted group of formula B;

alternatively, L₁The substituents in (a) are each independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, cyclopentyl, naphthyl, phenyl, biphenyl, dibenzofuranyl, dibenzothiophenyl, 9-dimethylfluorenyl.

In some embodiments of the present application, L₁Selected from substituted or unsubstituted groups V₁Unsubstituted radicals V₁Selected from the group consisting of:

wherein the content of the first and second substances,represents a chemical bond; the substituted group V₁Having one or more substituents thereon, each of said substituents being independently selected from deuterium, fluoro, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, cyclopentyl, phenyl, naphthyl, biphenyl, dibenzofuranyl, dibenzothiophenyl, 9-dimethylfluorenyl; when said substituted group V₁When there are a plurality of substituents, the substituents may be the same or different.

In some embodiments of the present application, L₁Selected from the group consisting of:

in some embodiments of the present application, L₀And L₂Each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, and a substituted or unsubstituted 5-to 13-membered heteroarylene group.

Alternatively, L₀And L₂Wherein the substituents are independently selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 5 carbon atoms, a cycloalkyl group having 5 to 10 carbon atoms, and an aryl group having 6 to 12 carbon atoms.

In some embodiments of the present application, L₀Selected from single bonds, substituted or unsubstituted groups V₂Unsubstituted radicals V₂Selected from the group consisting of:

wherein the content of the first and second substances,represents a chemical bond; the substituted group V₂Having one or more substituents thereon, each of said substituents being independently selected from deuterium, fluoro, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, cyclopentyl, phenyl or naphthyl; when said substituted group V₂When there are a plurality of substituents, the substituents may be the same or different.

In some embodiments of the present application, L₀Selected from the group consisting of single bonds or the following groups:

in some embodiments of the present application, L₂Selected from single bonds, substituted or unsubstituted groups V₃Unsubstituted radicals V₃Selected from the group consisting of:

wherein the content of the first and second substances,represents a chemical bond; the substituted group V₃Having one or more substituents thereon, each of said substituents being independently selected from deuterium, fluoro, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, cyclopentyl, biphenyl, phenyl, naphthyl; when said substituted group V₃When there are a plurality of substituents, the substituents may be the same or different.

In some embodiments of the present application, L₂Selected from the group consisting of single bonds or the following groups:

in some embodiments of the present application, Z₁Selected from substituted or unsubstituted aryl with 6-18 carbon atoms, substituted or unsubstituted 5-13 membered heteroaryl, diaryl phosphonyl and triphenyl silicon base.

Optionally, Z is₁Wherein the substituents are independently selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 5 carbon atoms, a cycloalkyl group having 5 to 10 carbon atoms, and an aryl group having 6 to 12 carbon atoms.

In some embodiments of the present application, Z₁Selected from the group consisting of substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted dibenzothienyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted benzoxazolyl, substituted or unsubstituted benzothiazolyl, substituted or unsubstituted triphenylene, substituted or unsubstituted fluorenyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted pyridyl, substituted or unsubstituted benzothiophenyl, diphenylphosphinyl, substituted or unsubstituted quinolyl, substituted or unsubstituted pyrimidyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted spiro [ cyclopentane-1, 9' -fluorenyl]Substituted or unsubstituted spiro [ cyclohexane-1, 9' -fluorenyl group]A substituted or unsubstituted group of formula C;

optionally, Z is₁Each substituent in (1) is independently selected from deuterium, fluoro, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, cyclopentyl, phenyl, naphthyl.

In some embodiments of the present application, Z₁Selected 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,represents a chemical bond; said substituted group W having one or more substituents thereon, each of said substituents being independently selected from deuterium, fluoro, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, cyclopentyl, phenyl; when there are a plurality of substituents on the substituted group W, the substituents may be the same or different.

In some embodiments of the present application, Z₁Selected from the group consisting of:

in one embodiment of the present application, the group represented by formula 2 is selected from the group consisting of:

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

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.

According to one embodiment, the electronic component is an organic electroluminescent device. The organic electroluminescent device may be, for example, a red organic electroluminescent device, a green organic electroluminescent device, or a blue organic electroluminescent device.

Optionally, the organic electroluminescent device is a red organic electroluminescent device or a blue organic electroluminescent device.

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 as provided in the first aspect of the present application.

In one embodiment of the present application, the functional layer 300 includes an electron transport layer 340, and the electron transport layer 340 includes the organic compound.

In one embodiment of the present application, the functional layer 300 includes an organic light emitting layer 330, and the organic light emitting layer 330 includes the organic compound.

In one embodiment, 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 includes a first hole transport layer 321 and a second hole transport layer 322.

In one embodiment, the anode 100 comprises an anode material, preferably a material with a large work function that facilitates hole injection into the functional layer. The anode material specifically includes: 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 and SnO₂: sb; conductive polymers such as poly (3-methylthiophene), poly [3,4- (ethylene-1, 2-dioxy) thiophene](PEDT), polypyrrole, and polyaniline, but are not limited thereto. Preferably, a transparent electrode comprising Indium Tin Oxide (ITO) as an anode is included.

In one embodiment, the first hole transport layer 321 may include one or more hole transport materials, and the first hole transport layer material may be selected from carbazole multimers, carbazole-linked triarylamine compounds, or other types of compounds, which are not specifically limited herein. Specifically, the first hole transport layer 321 is composed of the compound NPBAPF or Spiro-TPD.

In one embodiment, the second hole transport layer 322 may include one or more hole transport materials, and the second hole transport layer material may be selected from carbazole polymers or other types of compounds, which are not particularly limited in this application. In one embodiment, the second hole transport layer 322 is comprised of the compound TTP or α -NPD.

In the present application, the electron transport layer 340 may have a single-layer structure or a multi-layer structure, and may include one or more electron transport materials, and the electron transport materials further include one or more electron transport materials selected from benzimidazole derivatives, oxadiazole derivatives, quinoxaline derivatives, or other electron transport materials. In one embodiment of the present application, the electron transport layer 340 comprises an organic compound of the present application, and may be composed of the organic compound of the present application and LiQ, for example. In another embodiment of the present application, the electron transport layer 340 is composed of both BTB and LiQ.

In one embodiment, the organic light emitting layer 330 may be composed of a single light emitting material, or may be composed of a host material and a guest material. Preferably, 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 electrons injected into the organic light emitting layer 330 may be combined in the organic light emitting layer 330 to form excitons, which transfer energy to the host material, and the host material transfers energy to the guest material, thereby enabling the guest material to emit light.

The host material of the organic light emitting layer 330 may be the organic compound of the present application, or may be composed of the organic compound of the present application and other light emitting host materials, such as metal chelate compounds, bisstyryl derivatives, aromatic amine derivatives, dibenzofuran derivatives, or other types of materials, which are not limited in this application. In a specific embodiment, the host material of the organic light emitting layer 330 comprises a compound of the present application. Optionally, the host material is comprised of EFIN or an organic compound of the present application.

The guest material of the organic light emitting layer 330 may be a compound having a condensed aryl ring or a derivative thereof, a compound having a heteroaryl ring or a derivative thereof, an aromatic amine derivative, or other materials, which is not particularly limited in the present application. In one embodiment, the guest material of the organic light emitting layer 330 is PCAN or Ir (piq)₂(acac)。

Optionally, cathode 200 includes a cathode material that facilitates electron injection into the functional layerOf a material having a small work function. Specifically, 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; multilayer materials such as LiF/Al, Liq/Al, LiO₂Al, LiF/Ca, LiF/Al and BaF₂But not limited thereto,/Ca. Preferably, a metal electrode comprising silver and magnesium is included as a cathode.

In the present application, 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 PPDN or m-MTDATA.

In one embodiment, 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.

In one embodiment, the electronic component is a photoelectric conversion device. As shown in fig. 2, the photoelectric conversion device may include an anode 100, a hole transport layer 320, a photoelectric conversion layer 360, an electron transport layer 340, and a cathode 200, which are sequentially stacked.

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

A third aspect of the present disclosure provides an electronic device including the electronic element provided in the second aspect of the present disclosure. Since the electronic device has any one of the electronic elements described in the above embodiments of the electronic element, the electronic device has the same beneficial effects, and the details of the electronic device are not repeated herein.

As shown in fig. 3, one embodiment of the present application provides a first electronic device 400. The electronic device comprises the organic electroluminescent device. The first electronic device 400 may be a display device, a lighting device, an optical communication device or other types of electronic devices, and may include, but is not limited to, a computer screen, a mobile phone screen, a television, electronic paper, an emergency light, an optical module, and the like.

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

The present disclosure is further illustrated by the following examples, but is not to be construed as being limited thereby.

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 methods provided in the preparation examples section. 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.

In the synthesis examples described below, all temperatures are in degrees celsius unless otherwise stated. Some of the reagents were purchased from commercial suppliers such as Aldrich Chemical Company, and some of the intermediates that could not be purchased directly were prepared by simple reactions from commercially available starting materials and were used without further purification unless otherwise stated. The rest of conventional reagents are purchased from Nanjing Congralin chemical industry and industry Co., Ltd, Qingdao Tenglong chemical reagent Co., Ltd, Qingdao ocean chemical plant, etc.

In purification, the column was silica gel column, silica gel (80-120 mesh) was purchased from Qingdao oceanic plant.

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

Hydrogen nuclear magnetic resonance spectroscopy: bruker 400MHz NMR instrument in CDCl at room temperature₃Or CD₂Cl₂TMS (0ppm) was used as a reference standard for the solvent (in ppm).

Synthesis of intermediates of the following Structure

Synthesis of intermediate I

(1) Introducing nitrogen (0.100L/min) into a sealed reaction vessel for replacement for 2min, heating raw material I-1(100mmol,31.6g), raw material I-2(105mmol), triethylamine (200mmol,28mL), palladium acetate (1mmol) and 100mL of toluene to 100-105 ℃ for reaction for 12h, adding 50mL of water, separating, and extracting the aqueous phase with 50mL of toluene for 1 time. The combined organic phases were washed 2 times with water, the organic phases were dried over 5g of anhydrous sodium sulfate, filtered, the organic phases were concentrated (50 ℃ C. -60 ℃ C., -0.09 to-0.08 MPa) until no droplets were drained, 50mL of ethanol was added with stirring, and filtered to give 70.3mmol of intermediate I-3 with a yield of 70.3%.

(2) Introducing nitrogen into a three-neck flask provided with a mechanical stirrer, a thermometer and a condenser for 10min (2000mL/min), adding the intermediate I-3(60mmol), the raw material 1-4(66mmol), potassium carbonate (90mmol), 80.0mL of methanol and 40.0mL of acetonitrile, starting stirring, heating to 40-45 ℃, adding palladium acetate (1.2mmol), continuously heating to 60-65 ℃ for reaction for 3h, cooling the reaction solution to 25 ℃, filtering, leaching the solid with ethanol to obtain 50mmol of the intermediate I-5, wherein the yield is 83.3%.

(3) A three-necked flask equipped with a mechanical stirrer, a thermometer and a condenser was purged with nitrogen (0.100L/min) for 15min, and then, 60mL of intermediate I-5(40mmol), triphenylphosphine rhodium chloride (0.4mmol) and 1, 4-dioxane were sequentially added thereto. Heating to 85-90 ℃ for reaction for 5h, adding 120mL of water, filtering, pulping a filter cake for 1 time by using 50mL of ethanol, and filtering to obtain 7.33g of an intermediate I with the yield of 85%.

Intermediate II-intermediate V were synthesized with reference to the synthesis of intermediate I except that starting material Y1 in table 1 below was used instead of starting material I-4 in step (2) above.

TABLE 1

Synthesis example 1 Synthesis of Compound 2

(1) Introducing nitrogen (0.100L/min) into a three-neck flask provided with a mechanical stirring device, a thermometer and a spherical condenser for replacement for 15min, sequentially adding raw material 2a (50mmol, 12.46g), raw material 2b (CAS:1100754-73-1,55mmol, 17.83g), potassium carbonate (100mmol, 13.8g), tetrabutylammonium bromide (5mmol, 1.61g), 120mL of toluene, 40.0mL of ethanol and 40.0mL of water, starting stirring, heating to 40-45 ℃, adding tetrakistriphenylphosphine palladium (5mmol, 5.78g), continuously heating to 60-65 ℃ for reaction for 8h, adding 50mL of water, separating, and extracting the aqueous phase with 50mL of toluene for 1 time. The combined organic phases were washed 2 times with water, the organic phase was dried over 5g of anhydrous sodium sulfate, filtered, and the organic phase was concentrated (50 ℃ C. -60 ℃ C., -0.09 to-0.08 MPa) to 30mL for recrystallization to give intermediate 2c (30mmol, 14.8g) in 60% yield.

(2) Introducing nitrogen (0.100L/min) into a three-neck flask provided with a mechanical stirring device, a thermometer and a spherical condenser for replacement for 15min, sequentially adding an intermediate 2c (20mmol, 9.86g), a raw material 2d (22mmol, 4.36g), potassium carbonate (40mmol, 5.52g), tetrabutylammonium bromide (2mmol, 0.65g), 60mL of toluene, 20.0mL of ethanol and 20.0mL of water, starting stirring, heating to 40-45 ℃, adding dichloro-di-tert-butyl- (4-dimethylaminophenyl) phosphine palladium (1mmol, 0.71g), continuously heating to 60-65 ℃ for reaction for 1h, adding 20mL of water, separating, and extracting an aqueous phase with 20mL of toluene for 1 time. The combined organic phases were washed 2 times with water, the organic phases were dried over 2g of anhydrous sodium sulfate, filtered, the organic phases were concentrated (50 ℃ C. -60 ℃ C., -0.09 to-0.08 MPa) until no liquid flowed out, 10mL of ethanol was added, and filtration was carried out to give 10.02g of Compound 2, yield 82%. LC-MS (ESI, pos.ion) M/z 611.2[ M + H ═ M]⁺。¹H NMR(CDCl₃,400MHz):9.03-8.99(d,1H),8.79-8.73(m,4H),8.55-8.52(d,1H),8.47(s,2H),8.24-8.21(d,1H)，8.15-8.11(m,2H),8.06(s,1H),7.88-7.79(m,7H),7.69-7.66(d,1H),7.53-7.44(m,8H),7.31-7.29(m,2H).

Synthesis examples 2 to 28

The compounds in table 2 were synthesized with reference to the synthesis of compound 2, except that starting material Y2 was used instead of starting material 2b and starting material Y3 was used instead of starting material 2d, and the numbering, structure, yield and mass spectral data are listed in table 2.

TABLE 2

Synthesis example 29 Synthesis of Compound 114

(1) Introducing nitrogen (0.100L/min) into a three-neck flask provided with a mechanical stirrer, a thermometer and a spherical condenser for replacement for 15min, sequentially adding an intermediate I (30mmol, 6.47g), a raw material 114a (30mmol, 9.73g), potassium carbonate (60mmol, 8.28g), tetrabutylammonium bromide (6mmol, 1.93g), 100mL of toluene, 20.0mL of ethanol and 20.0mL of water, starting stirring, heating to 40-45 ℃, adding dichlorodi-tert-butyl- (4-dimethylaminophenyl) phosphine palladium (0.3mmol, 0.22g), continuously heating to 60-65 ℃ for reaction for 1h, adding 30mL of water, separating, and extracting an aqueous phase for 1 time by using 45mL of toluene. The combined organic phases were washed 2 times with water, dried over 2g of anhydrous sodium sulfate, filtered, the organic phase concentrated (50-60 ℃ C., -0.09 to-0.08 MPa) to no droplets, filtered by addition of 25mL of ethanol to give intermediate 114b (28.6mmol, 12.53g) in 95.3% yield.

(2) Introducing nitrogen (0.100L/min) into a three-neck flask provided with a mechanical stirrer, a thermometer and a spherical condenser for replacement for 15min, sequentially adding an intermediate 114b (20mmol, 9.19g) and 60mL of tetrahydrofuran, starting stirring, cooling to-65 ℃ to-60 ℃, dropwise adding LDA (24mmol, 12mL), continuously preserving heat for 1h after dropwise adding, dropwise adding a solution of a raw material 114c (24mmol, 6.80g) and 20mL of tetrahydrofuran, continuously preserving heat for 1h after dropwise adding, adding 50mL of water, extracting with 50mL of dichloromethane, extracting an aqueous phase with 30mL of dichloromethane, combining organic phases, washing with water for 2 times, drying the organic phase with 2g of anhydrous sodium sulfate, filtering, concentrating the organic phase (40 ℃ -45 ℃ and-0.06 MPa) until no liquid flows out, adding 10mL of petroleum ether, filtering to obtain 9.6g of a compound 114, the yield is 72.5%, LC-MS (ESI, io isn)m/z＝662.2[M+H]⁺。

Synthesis examples 30 to 63

The compounds in table 3 were synthesized with reference to the synthesis method of compound 114, except that raw material Y4 was used instead of raw material 114a and raw material Y5 was used instead of raw material 114c, and the number, structure, yield and mass spectrum data of the synthesized compounds are shown in table 3.

TABLE 3

Reference synthesis of compound 2 the following intermediates were synthesized with the difference that starting material Y6 was used instead of starting material 2a and starting material Y7 was used instead of 2d, and the numbering, structure and yields are given in table 4.

TABLE 4

Synthesis example 64 Synthesis of Compound 219

(1) Introducing nitrogen (0.100L/min) into a three-neck flask with a mechanical stirring thermometer for replacement for 15min, sequentially adding an intermediate 219m (20mmol, 8.17g) and 60mL of dichloroethane, starting stirring, cooling to-5-0 ℃, dropwise adding liquid bromine (21mmol, 3.34g), continuing heat preservation for 5h after dropwise adding is finished, adding 50mL of water, separating, extracting the aqueous phase with 30mL of dichloroethane, combining the organic phases, washing with water for 2 times, drying the organic phase with 2g of anhydrous sodium sulfate, filtering, concentrating the organic phase (40-45 ℃, from-0.06 to-0.05 Mpa) to dryness, and using ethyl acetate to obtain a product: column chromatography in 18mL petroleum ether (1 mL) afforded intermediate 219a (10mmol, 4.87g) in 50% yield.

(2) Introducing N into a three-mouth bottle provided with a mechanical stirring tube, a thermometer and a condenser tube₂(0.100L/min) for 15min, successively adding intermediate 219a (10mmol, 4.87g), raw material 219b (10.5mmol, 2.08g), potassium carbonate (20mmol, 2.76g), tetrabutylammonium bromide (1mmol, 0.33g), 30mL of toluene, 15mL of ethanol, and 10.0mL of water, stirring and heating to 40-45 ℃, adding dichloro-di-tert-butyl- (4-dimethylaminophenyl) phosphine palladium (0.2mmol, 0.14g), reacting at 60-65 ℃ for 2h, adding 10mL of water, separating, and extracting the aqueous phase with 10mL of toluene. The combined organic phases were washed 2 times with water, dried over 2g of anhydrous sodium sulfate, filtered, the organic phase was concentrated (50-60 ℃ C., -0.09 to-0.08 MPa) to dryness, 15mL of ethanol was added, and filtered to give compound 219(5.2g, 93% yield).

LC-MS(ESI,pos.ion)m/z＝561.2[M+H]⁺；

¹HNMR(CDCl₃,400MHz):8.83-8.79(m,2H),8.37-8.32(m,4H),8.01(s,1H),7.79-7.73(m,6H),7.57(s,1H)，7.52-7.47(m,5H),7.43-7.35(m,7H),7.31-7.29(d,1H),7.19-7.16(d,1H).

Synthesis examples 65 to 74

Reference synthesis of compound 219 the following compounds were synthesized with the difference that starting material Y8 was used instead of intermediate 219m and starting material Y9 was used instead of 219b, and the compound numbers, structures, yields and mass spectral data are listed in table 5.

TABLE 5

Synthesis example 75 Synthesis of Compound 293

(1) Introducing nitrogen (0.100L/min) into a three-neck flask provided with a mechanical stirrer, a thermometer and a spherical condenser for replacement for 15min, sequentially adding an intermediate I (30mmol, 6.45g), a raw material phenylboronic acid (33mmol, 4.03g), potassium carbonate (60mmol, 8.28g), tetrabutylammonium bromide (3mmol), 100mL of toluene, 20.0mL of ethanol and 20.0mL of water, starting stirring, heating to 40-45 ℃, adding dichloro-di-tert-butyl- (4-dimethylaminophenyl) phosphine palladium (0.3mmol), continuously heating to 60-65 ℃, reacting for 1h, adding 20mL of water, separating, and extracting the aqueous phase for 1 time by using 50mL of toluene. The combined organic phases were washed 2 times with water, dried over 2g of anhydrous sodium sulfate, filtered, the organic phase was concentrated (50-60 ℃ C., -0.09 to-0.08 MPa) until no droplets were formed, and filtered by adding 20mL of ethanol to give 7.35g of intermediate 293b, with a yield of 95.3%.

(2) Introducing nitrogen (0.100L/min) into a three-neck flask with a mechanical stirrer and a thermometer for replacement for 15min, sequentially adding an intermediate 293b (20mmol, 5.14g) and 60mL of dichloroethane, starting stirring, cooling to-5-0 ℃, dropwise adding liquid bromine (21mmol), continuing to preserve heat for 8h after dropwise addition, adding 40mL of water, separating, extracting the aqueous phase with 30mL of dichloroethane, combining the organic phases, washing with water for 2 times, drying the organic phase with 2g of anhydrous sodium sulfate, filtering, concentrating the organic phase (40-45 ℃, minus 0.06-0.05 Mpa) to dryness, and recrystallizing the obtained solid with toluene to obtain 2.68g of the intermediate 293c with the yield of 40%.

(3) Introducing nitrogen (0.100L/min) into a three-neck flask provided with a mechanical stirrer, a thermometer and a spherical condenser for replacement for 15min, sequentially adding an intermediate 293c (10mmol, 3.35g), a raw material 293d (11mmol, 3.16g), potassium carbonate (20mmol, 2.76g), tetrabutylammonium bromide (1mmol), 30mL of toluene, 10.0mL of ethanol and 10.0mL of water, starting stirring, heating to 40-45 ℃, adding dichlorodi-tert-butyl- (4-dimethylaminophenyl) phosphine palladium (0.1mmol), continuously heating to 60-65 ℃, reacting for 2h, adding 10mL of water, separating, and extracting the aqueous phase for 1 time by using 10mL of toluene. The combined organic phases were washed 2 times with water, dried over 2g of anhydrous sodium sulfate, filtered, the organic phase was concentrated (50-60 ℃ C., -0.09 to-0.08 MPa) until no droplets were formed, 15mL of ethanol was added, and filtered to give 4.70g of intermediate 293e, yield 94.2%.

(4) Introducing nitrogen (0.100L/min) into a three-neck flask provided with a mechanical stirring device, a thermometer and a spherical condenser tube for replacement for 15min, sequentially adding an intermediate 293e (5mmol, 2.49g) and 30mL of tetrahydrofuran, starting stirring, cooling to-65 to-60 ℃, dropwise adding LDA (13mmol, 6.5mL), continuously preserving heat for 1h after dropwise adding, dropwise adding raw materials 293f (12mmol, 3.02g) and 10mL of tetrahydrofuran solution, continuously preserving heat for 1h after dropwise adding, adding 30mL of water, extracting with 20mL of dichloromethane, extracting an aqueous phase with 20mL of dichloromethane, washing an organic phase with water for 2 times, drying an organic phase with 2g of anhydrous sodium sulfate, filtering, concentrating the organic phase (40-45 ℃, 0.06 to-0.05 Mpa) until no liquid flows out, adding 8mL of petroleum ether, filtering to obtain a compound 293(2.33g, yield 69.8%)，LC-MS(ESI,pos.ion)m/z＝669.2[M+H]⁺。

Reference compound 293 synthesis method the following compounds were synthesized with the difference that raw material Y10 was used instead of phenylboronic acid, raw material Y11 was used instead of 293d, raw material Y12 was used instead of 293f, and the numbers, structures, yields and mass spectral data are listed in table 6.

TABLE 6

Synthesis examples 90 to 97

Referring to the synthesis of compound 2, compounds in table 7 were synthesized using Y13 instead of 2b and Y14 instead of 2d, with the numbers, structures, yields and mass spectral data set forth in table 7.

TABLE 7

Synthesis examples 96 to 101

Referring to the synthesis of compound 114, intermediate II was used instead of intermediate I, starting material V was used instead of starting material 114a, and starting material VI was used instead of starting material 114c, the compounds in table 8 were synthesized, and the compound numbers, structures, yields, and mass spectral data are listed in table 8.

TABLE 8

Synthesis example 102-

Referring to the complete synthesis of compound 219, the following compounds were synthesized. Wherein intermediates were first prepared by reference to the synthesis of compound 2, intermediate III or intermediate V in table 9 below was used instead of starting material 2a, starting material Y15 was used instead of 2b, starting material Y16 was used instead of 2d to prepare intermediate xxxm (xxx stands for compound number), and then the following compounds were synthesized with reference to the last two-step preparation of compound 219, starting material Y17 was used instead of 219b, with the numbers, structures, yields and mass spectral data listed in table 9.

TABLE 9

Examples preparation and evaluation of Properties of blue organic electroluminescent device

Example 1

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), and prepared into an experimental substrate having a cathode, an anode and an insulating layer pattern by using a photolithography process, and UV ozone and O were used₂:N₂Plasma surface treatment to increase the work function of the anode, and organic solventThe agent is used for cleaning the surface of the ITO substrate so as to remove impurities and oil stains on the surface of the ITO substrate.

PPDN (CAS:215611-93-1) was vacuum evaporated onto the experimental substrate (anode) to a thickness ofAnd NPBAPF (CAS:510775-24-3) is vacuum-evaporated on the Hole Injection Layer (HIL) to form a layer having a thickness ofA first Hole Transport Layer (HTL).

TTP (CAS:80223-29-6) is evaporated on the first Hole Transport Layer (HTL) to a thickness ofThe second hole transport layer (EBL).

EFIN (CAS:1705571-72-7) as a main body was doped with PCAN (CAS:1261580-75-9) at a film thickness ratio of 97:3 to form a film having a thickness ofThe organic light emitting layer (EML).

Compound 2 and LiQ are mixed in a weight ratio of 1:1 and may be formed by an evaporation processA thick Electron Transport Layer (ETL). Subsequently, LiQ was evaporated on the electron transport layer to form a thickness ofThen, magnesium (Mg) and silver (Ag) were mixed at a rate of 1:9, and vacuum-evaporated on the Electron Injection Layer (EIL) to a thickness ofThe cathode of (1).

The thickness of the vapor deposition on the cathode is set toForming a capping layer (CPL), thereby completing the fabrication of the blue organic electroluminescent device.

Examples 2 to 84

In examples 2 to 84, organic electroluminescent devices were produced in the same manner as in example 1, except that the compounds in Table 11 were respectively used in place of compound 2.

Comparative examples 1 to 3

In comparative examples 1 to 3, organic electroluminescent devices were fabricated in the same manner as in example 1, except that compound a, compound B, and compound C, the structural formulae of which are shown in table 10 below, were used instead of compound 2, respectively:

table 10:

organic electroluminescent devices obtained in examples 1 to 84 and comparative examples 1 to 3 were each controlled at 15mA/cm²The service life of the T95 device is tested under the condition that the data working voltage, the efficiency and the color coordinate are 10mA/cm at constant current density²The following tests were carried out and the results are shown in Table 11.

TABLE 11

As can be seen from the data in Table 11, the organic electroluminescent devices prepared in examples 1 to 84, which have the compound of the present application as an electron transport material, have improved current efficiency (Cd/A) by at least 10.3% and improved lifetime by at least 15% while ensuring lower operating voltage, as compared with the devices prepared in comparative examples 1 to 3, which have compound A, B, C as an electron transport material.

Example 85 Red organic electroluminescent device

The anode was prepared by the following procedure: will have a thickness ofThe ITO substrate (manufactured by Corning) of (1) was cut into a size of 40mm × 40mm × 0.7mm, prepared into an experimental substrate having a cathode, an anode and an insulating layer pattern using a photolithography process, using ultraviolet ozone and O₂:N₂The plasma was surface treated to increase the work function of the anode (experimental substrate) and to remove scum. And organic solvent can be adopted to clean the surface of the ITO substrate so as to remove impurities and oil stains on the surface of the ITO substrate.

The m-MTDATA (CAS:124729-98-2) was vacuum evaporated on the experimental substrate (anode) to a thickness ofAnd a layer (HIL) of Spiro-TPD (CAS:1033035-83-4) is formed to a thickness ofThe first hole transport layer of (1).

Vacuum evaporating alpha-NPD (CAS:495416-60-9) on the hole transport layer to form a layer with a thickness ofThe second hole transport layer of (1).

Compound 277: ir (piq)₂(acac) at 97%: co-evaporation is carried out at a film thickness ratio of 3% to form a film having a thickness ofThe red organic light emitting layer (R-EML).

BTB (CAS:266349-83-1) and LiQ are mixed and evaporated at a weight ratio of 1:1A thick Electron Transport Layer (ETL), and depositing LiQ on the electron transport layer to form a layer with a thickness ofAnd then magnesium (Mg) and silver (Ag) are mixed in a ratio of 1:9 is vacuum-evaporated on the electron injection layer to a thickness ofThe cathode of (1).

The thickness of the vapor deposition on the cathode is set toThe organic capping layer (CPL) is formed to complete the fabrication of the organic light emitting device, and the structure is as follows.

Examples 86 to 113

In examples 86 to 113, organic electroluminescent devices were produced in the same manner as in example 85 except that the compounds in Table 12 were used in place of the compound 277, respectively.

Comparative examples 4 to 7

In comparative examples 4 to 7, organic electroluminescent elements were fabricated in the same manner as in example 85, except that compound D, compound E, compound F, compound G, each having the following structural formula, was used instead of compound 277:

organic electroluminescent devices prepared in examples 85 to 113 and comparative examples 4 to 7 were operated at 15mA/cm²The service life of the T95 device is tested under the condition that the data working voltage, the efficiency and the color coordinate are 10mA/cm at constant current density²The following tests were carried out and the results are shown in Table 12.

TABLE 12

From the data in Table 12, it can be seen that the organic electroluminescent devices prepared in examples 85 to 113, which have the compound of the present application as the host material of the organic light-emitting layer, have at least 11% higher current efficiency (Cd/A) and at least 19% higher lifetime while ensuring lower operating voltage than the organic electroluminescent devices prepared in comparative examples 4 to 7, which have compound D, E, F, G as the host material.

Some representative 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.