A fused ring compound and use thereof

Abstract

The application belongs to the technical field of display, and particularly relates to a fused ring compound and application thereof. The fused ring compound provided by the application is based on the structure of formula (1), and the type of substituent group is further limited, so that the structural stability of the compound is improved. The HOMO and LUMO energy levels of the fused ring compound have higher matching degrees with adjacent energy levels, so that the carrier mobility of the fused ring compound is relatively balanced, and further, the organic electroluminescent device containing the fused ring compound has lower driving voltage, higher luminous efficiency and longer service life.

Description

Technical Field

[0001] This invention belongs to the field of display technology, specifically relating to a fused ring compound and its applications. Background Technology

[0002] Organic light-emitting diodes (OLEDs) are semiconductor devices that achieve photoelectric conversion based on a charge injection excitation mechanism. Their typical structure consists of an anode, a cathode, and a sandwich functional system: the anode is a metal oxide layer with hole transport characteristics, the cathode is a low work function metal material, and the sandwich functional layer system usually consists of a carrier injection layer, a transport layer, an exciton confinement layer, and a bipolar light-emitting dielectric layer.

[0003] In operation, holes migrate to the luminescent region through the hole injection layer, while electrons are transported to the region through the electron injection layer. When these two types of charge carriers recombine in the luminescent medium, they form excitons in an excited state. These excited excitons release energy through radiative transitions, and their energy conversion efficiency directly determines the luminescent performance of the device.

[0004] The choice of material system is a core factor affecting device performance. An ideal light-emitting material needs to possess high stability, an energy level structure that matches adjacent functional layers, and balanced carrier mobility characteristics. However, the performance of existing organic electroluminescent materials is poor, resulting in high device driving voltage, low current efficiency, and short operating lifetime. These technical bottlenecks severely restrict the industrial application of OLEDs. Summary of the Invention

[0005] The purpose of this invention is to overcome the problems of high driving voltage, low current efficiency and short device life caused by the poor performance of existing organic electroluminescent materials, and to provide a fused ring compound and its application.

[0006] In the definition of substituent terms in this invention:

[0007] The term "organic electroluminescent material" in this invention disclosure refers to a material that can be used in organic electroluminescent devices and may contain at least one compound. If desired, the organic electroluminescent material may be contained in any layer constituting the organic electroluminescent device. For example, the organic electroluminescent material may be a hole injection material, a hole transport material, a hole assist material, a light-emitting assist material, an electron blocking material, a light-emitting material (containing a host material and a dopant material), an electron buffer material, a hole blocking material, an electron transport material, an electron injection material, etc.

[0008] The term "multiple organic electroluminescent materials" in this invention disclosure refers to one or more organic electroluminescent materials comprising a combination of at least two compounds, said materials may be contained in any layer constituting an organic electroluminescent device. It may mean both materials contained before (e.g., before vapor deposition) and materials contained after (e.g., after vapor deposition) the organic electroluminescent device. For example, multiple organic electroluminescent materials may be a combination of at least two compounds, said materials may contain at least one of the following: a hole injection layer, a hole transport layer, a hole auxiliary layer, a light-emitting auxiliary layer, a light-emitting layer, an electron buffer layer, a hole blocking layer, an electron transport layer, and an electron injection layer. The at least two compounds may be contained in the same layer or different layers, and may be mixed-evaporated or co-evaporated, or may be evaporated individually.

[0009] In this invention, the descriptive terms “each…independently selected”, “each…independently constitute”, and “each…independently constitute” are interchangeable and should be interpreted broadly. They can mean that the specific options expressed by the same symbols in different groups do not affect each other, or that the specific options expressed by the same symbols in the same group do not affect each other.

[0010] In this invention, the term "substituent" has its usual meaning as known in the art, referring to a chemical moiety covalently attached to or, where appropriate, fused to a parent nucleus group.

[0011] In this invention, the term "substituted or unsubstituted" means that the functional group described after the term may or may not have substituents (hereinafter, for ease of description, substituents are 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 mentioned above can be, for example, deuterium, halogen, cyano, C1-C60 alkyl, C3-C60 cycloalkyl, C6-C60 aryl, or C1-C60 heteroaryl. Optionally, it can be, for example, deuterium, halogen group, cyano, alkyl, haloalkyl, trialkylsilyl, deuterated alkyl, aryl, heteroaryl, etc. Of course, the number of substituents Rc can be one or more. When two substituents Rc are attached to the same atom, the two substituents Rc can exist independently or be connected to each other to form a ring with the atom; when two adjacent substituents Rc exist on a functional group, the two adjacent substituents Rc can exist independently or fused with the functional group to which they are attached to form a ring.

[0012] In this invention, C1-C60, C3-C60, and C6-C60 define the range of carbon atoms, where the number of carbon atoms is any integer within the defined range. For example, C6-C60 aryl means that the number of carbon atoms representing the aryl group can be any integer within the range of 6-60, such as 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39, 40, 41, 42, 43, 44, 45, 46, 47, 48, 49, 50, 51, 52, 53, 54, 55, 56, 57, 58, 59, and 60.

[0013] In this invention, the term "alkyl" refers, whether as part of other terms or used alone, to a saturated hydrocarbon group, which may be straight-chain or branched. The term "C1-C60 alkyl" is derived from a monovalent substituent of a straight-chain or branched saturated hydrocarbon having 1 to 60 carbon atoms, preferably 1 to 40 carbon atoms, and more preferably 1 to 20 carbon atoms. Examples of such substituents include, but are not limited to, methyl, ethyl, propyl, isobutyl, sec-butyl, tert-butyl, pentyl, isopentyl, and hexyl.

[0014] In this invention, the term "cycloalkyl" refers to a cyclic alkyl group consisting of at least 3 carbon atoms. Further, C3-C60 cycloalkyl refers to a monocyclic or polycyclic hydrocarbon derived from a main cyclic chain of 3 to 60 carbon atoms, preferably 3 to 40 carbon atoms, and even more preferably 3 to 20 carbon atoms. The cycloalkyl group includes, but is not limited to, cyclopropyl, cyclobutyl, adamantyl, etc.

[0015] In this invention, the term "heterocyclic alkyl" includes one or more of O, S, Se, N, and Si as heteroatoms. C1-C60 cycloalkyl refers to a monocyclic or polycyclic hydrocarbon derived from a main chain of 1 to 60 carbon atoms, preferably 3 to 40 carbon atoms, and even more preferably 3 to 20 carbon atoms. Here, "polycyclic" refers to a group in which a heterocyclic alkyl group is directly attached to or fused with another cyclic group. Here, the other cyclic group can also be a heterocyclic alkyl group, or another type of cyclic group, such as cycloalkyl, aryl, heteroaryl, etc.

[0016] In this invention, the term "alkoxy group" refers to a monovalent functional group attached to the parent molecule via an oxygen atom (-O-), and its general formula is optionally -OR, where R represents an alkyl group, including straight-chain, branched, or cyclic structures. For example, R can be methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, etc.

[0017] In this invention, the term "alkylthio" refers to a monovalent functional group in which a sulfur atom (-S-) is attached to a parent molecule. Its general formula is optionally -SR, where R represents an alkyl group, including straight-chain, branched, or cyclic structures. For example, R can be methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, etc.

[0018] In this invention, the term "aryloxy group" refers to a monovalent functional group in which an oxygen atom (-O-) bridges to the parent molecule. Its general formula can be -O-Ar, where Ar represents an aryl group, which can be a carbocyclic aromatic group, including monocyclic, polycyclic, or fused-ring aryl groups. For example, Ar can be phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, anthracene, fluorene, spirodifluorene, etc. Aleurones include, but are not limited to, phenylene, biphenylene, terphenylene, naphthylene, phenanthrylene, anthracene, fluorene, spirodifluorene, etc.

[0019] In this invention, the term "alkylamine" refers to a monovalent or divalent functional group that is attached to the parent molecule through a nitrogen atom. Its general formula can be expressed as -NHR, -NRR', or -NR- (divalent form), where R and R' independently represent alkyl groups, including straight-chain, branched, or cyclic structures. For example, R can be methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, etc.

[0020] In this invention, the terms "aryl" and "arylene" include monocyclic, polycyclic, or fused-ring aryl groups, wherein the rings may be interrupted by short non-aromatic units, and may contain a spirostructure. Aryl groups include, but are not limited to, phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, anthracene, fluorene, and spirodifluorene. Arylene groups include, but are not limited to, phenylene, biphenylene, terphenylene, naphthylene, phenanthrylene, anthraceneene, fluorene, and spirodifluorene. Arylene refers to a divalent or polyvalent group formed by the further loss of one or more hydrogen atoms from an aryl group.

[0021] In this invention, the term "heteroaryl" includes monocyclic, polycyclic, or fused-ring heteroaryl groups, wherein the rings may be interrupted by short non-aromatic units, and the heteroatoms include nitrogen, oxygen, sulfur, and selenium. Heteroaryl groups in this invention include, but are not limited to, furanyl, phenylthio, pyrroleyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetraazinyl, triazolyl, tetraazolyl, pyridinyl, pyrazinyl, and pyrimidinyl. Pyridyl, benzofuranyl, benzothiophene, isobenzofuranyl, dibenzofuranyl, dibenzothiophene, benzimidazolyl, benzothiazolyl, benzoisothiazolyl, benzoisooxazolyl, benzooxazolyl, isoindolyl, indolyl, indazole, benzothiadiazolyl, quinolinyl, isoquinolinyl, cenolinyl, quinazolinyl, quinoxalolinyl, carbazole, phenoxazinyl, phenthiazinyl, phenanthidyl, benzo-m-dioxacyclopentenyl, dihydroazolyl Pyridyl groups and their derivatives, etc.; heteroaryl groups include, but are not limited to, pyridinethioyl, pyridinepyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetrazinyl, triazolyl, tetrazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridinyl, pyridazinyl, benzofuranyl, benzothiopheneyl, isobenzofuranyl, and dibenzofuranyl. The group includes, but is not limited to, dibenzothiophene, benzimidazolyl, benzithiazolyl, benzisisothiazolyl, benzisisooxazolyl, benzisoxazolyl, isoindolyl, indolyl, indazolyl, benzisthiadiazolyl, quinolinyl, isoquinolinyl, cenolinyl, quinoxolinyl, quinoxalinyl, carbazolyl, phenoxazinyl, phenthiazinyl, phenanthridineyl, benzism-dioxacyclopentenyl, dihydroacridyl, and their derivatives.

[0022] In this invention, the term "single bond" refers to the connection between two adjacent groups.

[0023] In this invention, unless otherwise specified, the substituents do not fuse with the group to which they belong.

[0024] In this invention, if the group is not specified as substituted or unsubstituted, it means that it has not been substituted.

[0025] In this invention, It refers to the chemical bond that connects with other groups.

[0026] In this invention, the non-positioning connecting key involves a single bond extending from the ring system. "This means that one end of the linking bond can be connected to any position in the ring system that the bond passes through, and the other end is connected to the rest of the compound molecule."

[0027] The solution adopted in this invention is as follows: This invention provides a fused-ring compound having the structure shown in formula (1):

[0028] In equation (1), Ra is selected from the structure shown in equation (A); L is selected from substituted or unsubstituted C6-C60 arylene, substituted or unsubstituted C3-C60 heteroarylene; Ar 1 and Ar 2 Each is independently selected from substituted or unsubstituted C3-C60 heteroaryl groups;

[0029] In formula (A), Indicates a connection key; X1 and X2 are each independently selected from CRb or N, and at least one of X1 and X2 is selected from N. Rb is selected from hydrogen, deuterium, cyano, halogen, amino, acyl, carboxyl, silyl, trifluoromethyl, substituted or unsubstituted C1-C60 alkathio, substituted or unsubstituted C1-C60 alkoxy, substituted or unsubstituted C6-C60 aryloxy, substituted or unsubstituted C6-C60 arylthio, substituted or unsubstituted C1-C60 alkylamino, substituted or unsubstituted C1-C60 alkyl, substituted or unsubstituted C3-C60 cycloalkyl, substituted or unsubstituted C1-C60 heterocycloalkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl. Among them, substituted C1-C60 alkathioyl, substituted C1-C60 alkoxy, substituted C6-C60 aryloxy, substituted C6-C60 arylthio, substituted C1-C60 alkylamino, substituted C1-C60 alkyl, substituted C3-C60 cycloalkyl, substituted C1-C60 heterocycloalkyl, substituted C6-C60 aryl, substituted C3-C60 heteroaryl, substituted C6-C60 arylene, substituted The substituents in C3-C60 heteroaryl groups are selected from one or more of the following: deuterium, cyano, halogen, amino, acyl, carboxyl, silyl, trifluoromethyl, C1-C60 alkylthio, C1-C60 alkoxy, C6-C60 aryloxy, C6-C60 arylthio, C1-C60 alkylamino, C1-C60 alkyl, C3-C60 cycloalkyl, C1-C60 heterocycloalkyl, C6-C60 aryl, and C3-C60 aryl.

[0030] Preferably, the fused ring compound has the structure shown in formulas (2) to (5);

[0031]

[0032] In the formula, Ar 1 Ar2 The definitions of L, X1, and X2 are as described above.

[0033] Optionally, X1 is N, X2 is selected from CRb, and Rb is selected from hydrogen, deuterium, cyano, halogen, amino, acyl, carboxyl, silyl, trifluoromethyl, substituted or unsubstituted C1-C60 alkathio, substituted or unsubstituted C1-C60 alkoxy, substituted or unsubstituted C6-C60 aryloxy, substituted or unsubstituted C6-C60 arylthio, substituted or unsubstituted C1-C60 alkylamino, substituted or unsubstituted C1-C60 alkyl, substituted or unsubstituted C3-C60 cycloalkyl, substituted or unsubstituted C1-C60 heterocycloalkyl, substituted or unsubstituted C6-C60 aryl, and substituted or unsubstituted C3-C60 heteroaryl. Optionally, X2 is N, X1 is selected from CRb, and Rb is selected from hydrogen, deuterium, cyano, halogen, amino, acyl, carboxyl, silyl, trifluoromethyl, substituted or unsubstituted C1-C60 alkathio, substituted or unsubstituted C1-C60 alkoxy, substituted or unsubstituted C6-C60 aryloxy, substituted or unsubstituted C6-C60 arylthio, substituted or unsubstituted C1-C60 alkylamino, substituted or unsubstituted C1-C60 alkyl, substituted or unsubstituted C3-C60 cycloalkyl, substituted or unsubstituted C1-C60 heterocycloalkyl, substituted or unsubstituted C6-C60 aryl, and substituted or unsubstituted C3-C60 heteroaryl. Preferably, Rb is selected from hydrogen, deuterium, cyano, halogen, amino, acyl, carboxyl, silyl, trifluoromethyl, substituted or unsubstituted C1-C50 alkathio, substituted or unsubstituted C1-C50 alkoxy, substituted or unsubstituted C6-C50 aryloxy, substituted or unsubstituted C6-C50 arylthio, substituted or unsubstituted C1-C50 alkylamino, substituted or unsubstituted C1-C50 alkyl, substituted or unsubstituted C3-C50 cycloalkyl, substituted or unsubstituted C1-C50 heterocycloalkyl, substituted or unsubstituted C6-C50 aryl, and substituted or unsubstituted C3-C50 heteroaryl. The substituents in the substituted C1-C50 alkylthio, substituted C1-C50 alkoxy, substituted C6-C50 aryloxy, substituted C6-C50 arylthio, substituted C1-C50 alkylamino, substituted C1-C50 alkyl, substituted C3-C50 cycloalkyl, substituted C1-C50 heterocyclic alkyl, substituted C6-C50 aryl, and substituted C1-C50 heteroaryl are selected from one or more of deuterium, cyano, halogen, amino, acyl, carboxyl, silyl, trifluoromethyl, C1-C50 alkylthio, C1-C50 alkoxy, C6-C50 aryloxy, C6-C50 arylthio, C1-C50 alkylamino, C1-C50 alkyl, C3-C50 cycloalkyl, C1-C50 heterocyclic alkyl, C6-C50 aryl, and C3-C50 aryl.

[0034] Preferably, Rb is selected from hydrogen, deuterium, cyano, halogen, amino, acyl, carboxyl, silyl, trifluoromethyl, substituted or unsubstituted C1-C25 alkathio, substituted or unsubstituted C1-C25 alkoxy, substituted or unsubstituted C6-C25 aryloxy, substituted or unsubstituted C6-C25 arylthio, substituted or unsubstituted C1-C25 alkylamino, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C25 cycloalkyl, substituted or unsubstituted C1-C25 heterocycloalkyl, substituted or unsubstituted C6-C25 aryl, and substituted or unsubstituted C3-C25 heteroaryl. The substituents in the substituted C1-C25 alkylthio, substituted C1-C25 alkoxy, substituted C6-C25 aryloxy, substituted C6-C25 arylthio, substituted C1-C25 alkylamino, substituted C1-C25 alkyl, substituted C3-C25 cycloalkyl, substituted C1-C25 heterocyclic alkyl, substituted C6-C25 aryl, and substituted C1-C25 heteroaryl are selected from one or more of deuterium, cyano, halogen, amino, acyl, carboxyl, silyl, trifluoromethyl, C1-C25 alkylthio, C1-C25 alkoxy, C6-C25 aryloxy, C6-C25 arylthio, C1-C25 alkylamino, C1-C25 alkyl, C3-C25 cycloalkyl, C1-C25 heterocyclic alkyl, C6-C25 aryl, and C3-C25 aryl.

[0035] Preferably, Rb is selected from hydrogen, deuterium, cyano, halogen, amino, acyl, carboxyl, silyl, trifluoromethyl, substituted or unsubstituted C1-C12 alkathio, substituted or unsubstituted C1-C12 alkoxy, substituted or unsubstituted C6-C12 aryloxy, substituted or unsubstituted C6-C12 arylthio, substituted or unsubstituted C1-C12 alkylamino, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C1-C12 heterocycloalkyl, substituted or unsubstituted C6-C12 aryl, and substituted or unsubstituted C3-C12 heteroaryl. The substituents in the substituted C1-C12 alkylthio, substituted C1-C12 alkoxy, substituted C6-C12 aryloxy, substituted C6-C12 arylthio, substituted C1-C12 alkylamino, substituted C1-C12 alkyl, substituted C3-C12 cycloalkyl, substituted C1-C12 heterocyclic alkyl, substituted C6-C12 aryl, and substituted C1-C12 heteroaryl are selected from one or more of deuterium, cyano, halogen, amino, acyl, carboxyl, silyl, trifluoromethyl, C1-C12 alkylthio, C1-C12 alkoxy, C6-C12 aryloxy, C6-C12 arylthio, C1-C12 alkylamino, C1-C12 alkyl, C3-C12 cycloalkyl, C1-C12 heterocyclic alkyl, C6-C12 aryl, and C3-C12 aryl.

[0036] Preferably, Rb is selected from one or more of hydrogen, deuterium, cyano, halogen, amino, acyl, carboxyl, silyl, trifluoromethyl, methyl, ethyl, tert-butyl, phenyl, naphthyl, biphenyl, phenylnaphthyl, naphthylphenyl, terphenyl, binaphthyl, pyridyl, pyrimidinyl, dibenzofuranyl, and dibenzothiopheneyl. Preferably, Rb is selected from hydrogen; Optionally, X1 and X2 are N; Preferably, the fused ring compound has the structure shown in formula (6) to (7);

[0037] In the formula, Ar 1 Ar 2 The definitions of L are as described above.

[0038] Preferably, L is selected from substituted or unsubstituted C6-C50 arylene and substituted or unsubstituted C3-C50 heteroarylene; wherein the substituents in the substituted C6-C50 arylene and substituted C3-C50 heteroarylene are selected from one or more of deuterium, cyano, halogen, amino, acyl, carboxyl, silyl, trifluoromethyl, C1-C50 alkylthio, C1-C50 alkoxy, C6-C50 aryloxy, C6-C50 arylthio, C1-C50 alkylamino, C1-C50 alkyl, C3-C50 cycloalkyl, C1-C50 heterocycloalkyl, C6-C50 aryl, and C3-C50 aryl.

[0039] Preferably, L is selected from substituted or unsubstituted C6-C25 arylene or substituted or unsubstituted C3-C25 heteroarylene; The substituents in the substituted C6-C25 arylene and substituted C3-C25 heteroarylene are selected from one or more of the following: deuterium, cyano, halogen, amino, acyl, carboxyl, silyl, trifluoromethyl, C1-C25 alkylthio, C1-C25 alkoxy, C6-C25 aryloxy, C6-C25 arylthio, C1-C25 alkylamino, C1-C25 alkyl, C3-C25 cycloalkyl, C1-C25 heterocycloalkyl, C6-C25 aryl, and C3-C25 aryl.

[0040] Preferably, L is selected from substituted or unsubstituted C6-C12 arylene or substituted or unsubstituted C3-C12 heteroarylene; The substituents in the substituted C6-C12 arylene and substituted C3-C12 heteroarylene are selected from one or more of the following: deuterium, cyano, halogen, amino, acyl, carboxyl, silyl, trifluoromethyl, C1-C12 alkylthio, C1-C12 alkoxy, C6-C12 aryloxy, C6-C12 arylthio, C1-C12 alkylamino, C1-C12 alkyl, C3-C12 cycloalkyl, C1-C12 heterocycloalkyl, C6-C12 aryl, and C3-C12 aryl.

[0041] Preferably, L is selected from substituted or unsubstituted group D, wherein group D is selected from one of phenylene, naphthylene, biphenylene, binatylene, naphthylphenylene, phenylenenaphthylene, pyridylene, pyrimidinylene, dibenzofuranylene, and dibenzothiopheneylene; Wherein, the substituent in the substituted group D is selected from one or more of the following: deuterium, cyano, halogen, amino, acyl, carboxyl, silyl, trifluoromethyl, tert-butyl, methoxy, phenoxy, phenyl, naphthyl, biphenyl, pyridyl, and pyrimidinyl.

[0042] Preferred, Ar 1 and Ar 2 Each is independently selected from substituted or unsubstituted C3-C50 heteroaryl groups; The substituents in the substituted C3-C50 heteroaryl groups are selected from one or more of the following: deuterium, cyano, halogen, amino, acyl, carboxyl, silyl, trifluoromethyl, C1-C50 alkylthio, C1-C50 alkoxy, C6-C50 aryloxy, C6-C50 arylthio, C1-C50 alkylamino, C1-C50 alkyl, C3-C50 cycloalkyl, C1-C50 heterocycloalkyl, C6-C50 aryl, and C3-C50 aryl.

[0043] Preferred, Ar 1 and Ar 2 Each is independently selected from substituted or unsubstituted C3-C25 heteroaryl groups; The substituents in the substituted C3-C25 heteroaryl groups are selected from one or more of the following: deuterium, cyano, halogen, amino, acyl, carboxyl, silyl, trifluoromethyl, C1-C25 alkylthio, C1-C25 alkoxy, C6-C25 aryloxy, C6-C25 arylthio, C1-C25 alkylamino, C1-C25 alkyl, C3-C25 cycloalkyl, C1-C25 heterocycloalkyl, C6-C25 aryl, and C3-C25 aryl.

[0044] Preferred, Ar 1 and Ar 2 Each is independently selected from substituted or unsubstituted C3-C12 heteroaryl groups; The substituents in the substituted C6-C12 aryl and substituted C3-C12 heteroaryl are selected from one or more of the following: deuterium, cyano, halogen, amino, acyl, carboxyl, silyl, trifluoromethyl, C1-C12 alkylthio, C1-C12 alkoxy, C6-C12 aryloxy, C6-C12 arylthio, C1-C12 alkylamino, C1-C12 alkyl, C3-C12 cycloalkyl, C1-C12 heterocycloalkyl, C6-C12 aryl, and C3-C12 aryl.

[0045] Preferred, Ar 1 and Ar 2 Each substituted or unsubstituted group E is independently selected from:

[0046]

[0047] ; Wherein, the substituent in the substituted group E is selected from one or more of the following: deuterium, cyano, halogen, amino, acyl, carboxyl, silyl, trifluoromethyl, pyridine, naphthyl, biphenyl, terphenyl, phenylnaphthyl, naphthylphenyl, pyridyl, pyrimidinyl, dibenzofuranyl, and dibenzothiophene.

[0048] Preferred, Ar 1 and Ar 2 Pyridyl groups that are not substituted with phenyl groups.

[0049] It is understandable that in this invention, Indicates the connection location.

[0050] It is understood that the number of substituents is not limited in this invention, and the number of substituents can be 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, etc. For example, when the substituent is deuterium, it can be fully deuterated, semi-deuterated, or 1, 2, 3, 4... deuterium substitutions.

[0051] Preferably, the fused-ring compound has the following structure:

[0052]

[0053]

[0054] .

[0055] This invention also provides a method for synthesizing the compound shown, the specific synthetic route of which is shown in the following reaction formula: The synthesis method of the structure shown in Equation (5), Ar 1 and Ar 2 When the results are the same, the synthetic route is as follows:

[0056] or The synthesis method of the structure shown in Equation (6) is Ar 1 and Ar 2 When the results are the same, the synthetic route is as follows: or .

[0057] The present invention also provides an n-type charge generating material, which includes any one or a combination of at least two of the fused ring compounds described above.

[0058] The present invention also provides an electron transport material, which includes any one or a combination of at least two of the fused ring compounds described above.

[0059] The present invention also provides a hole-blocking material, which includes any one or a combination of at least two of the fused ring compounds described above.

[0060] The present invention also provides an organic electroluminescent device, the organic electroluminescent device comprising a cathode, an anode, and an organic layer located between the cathode and the anode, the organic layer comprising a structure as shown in formula (1):

[0061] In equation (1), Ra is selected from the structure shown in equation (A); L is selected from substituted or unsubstituted C6-C60 arylene, substituted or unsubstituted C3-C60 heteroarylene; Ar 1 and Ar 2 Each is independently selected from substituted or unsubstituted C6-C60 aryl or substituted or unsubstituted C3-C60 heteroaryl;

[0062] In formula (A), Indicates a connection key; X1 and X2 are each independently selected from CRb or N, and at least one of X1 and X2 is selected from N. Rb is selected from hydrogen, deuterium, cyano, halogen, amino, acyl, carboxyl, silyl, trifluoromethyl, substituted or unsubstituted C1-C60 alkathio, substituted or unsubstituted C1-C60 alkoxy, substituted or unsubstituted C6-C60 aryloxy, substituted or unsubstituted C6-C60 arylthio, substituted or unsubstituted C1-C60 alkylamino, substituted or unsubstituted C1-C60 alkyl, substituted or unsubstituted C3-C60 cycloalkyl, substituted or unsubstituted C1-C60 heterocycloalkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl. The substituents in the substituted C1-C60 alkylthio, substituted C1-C60 alkoxy, substituted C6-C60 aryloxy, substituted C6-C60 arylthio, substituted C1-C60 alkylamino, substituted C1-C60 alkyl, substituted C3-C60 cycloalkyl, substituted C1-C60 heterocycloalkyl, substituted C6-C60 aryl, and substituted C3-C60 heteroaryl are selected from one or more of deuterium, cyano, halogen, amino, acyl, carboxyl, silyl, trifluoromethyl, C1-C60 alkylthio, C1-C60 alkoxy, C6-C60 aryloxy, C6-C60 arylthio, C1-C60 alkylamino, C1-C60 alkyl, C3-C60 cycloalkyl, C1-C60 heterocycloalkyl, C6-C60 aryl, and C3-C60 aryl.

[0063] Preferably, the fused ring compound has the structure shown in formulas (2) to (5);

[0064] In the formula, Ar 1 Ar 2 The definitions of L, X1, and X2 are as described above; Optionally, X1 is N, X2 is selected from CRb, and Rb is selected from hydrogen, deuterium, cyano, halogen, amino, acyl, carboxyl, silyl, trifluoromethyl, substituted or unsubstituted C1-C60 alkathio, substituted or unsubstituted C1-C60 alkoxy, substituted or unsubstituted C6-C60 aryloxy, substituted or unsubstituted C6-C60 arylthio, substituted or unsubstituted C1-C60 alkylamino, substituted or unsubstituted C1-C60 alkyl, substituted or unsubstituted C3-C60 cycloalkyl, substituted or unsubstituted C1-C60 heterocycloalkyl, substituted or unsubstituted C6-C60 aryl, and substituted or unsubstituted C3-C60 heteroaryl. Optionally, X2 is N, X1 is selected from CRb, and Rb is selected from hydrogen, deuterium, cyano, halogen, amino, acyl, carboxyl, silyl, trifluoromethyl, substituted or unsubstituted C1-C60 alkathio, substituted or unsubstituted C1-C60 alkoxy, substituted or unsubstituted C6-C60 aryloxy, substituted or unsubstituted C6-C60 arylthio, substituted or unsubstituted C1-C60 alkylamino, substituted or unsubstituted C1-C60 alkyl, substituted or unsubstituted C3-C60 cycloalkyl, substituted or unsubstituted C1-C60 heterocycloalkyl, substituted or unsubstituted C6-C60 aryl, and substituted or unsubstituted C3-C60 heteroaryl. Optionally, X1 and X2 are N; Preferably, Rb is selected from hydrogen, deuterium, cyano, halogen, amino, acyl, carboxyl, silyl, trifluoromethyl, substituted or unsubstituted C1-C50 alkathio, substituted or unsubstituted C1-C50 alkoxy, substituted or unsubstituted C6-C50 aryloxy, substituted or unsubstituted C6-C50 arylthio, substituted or unsubstituted C1-C50 alkylamino, substituted or unsubstituted C1-C50 alkyl, substituted or unsubstituted C3-C50 cycloalkyl, substituted or unsubstituted C1-C50 heterocycloalkyl, substituted or unsubstituted C6-C50 aryl, and substituted or unsubstituted C3-C50 heteroaryl. The substituents in the substituted C1-C50 alkylthio, substituted C1-C50 alkoxy, substituted C6-C50 aryloxy, substituted C6-C50 arylthio, substituted C1-C50 alkylamino, substituted C1-C50 alkyl, substituted C3-C50 cycloalkyl, substituted C1-C50 heterocyclic alkyl, substituted C6-C50 aryl, and substituted C1-C50 heteroaryl are selected from one or more of deuterium, cyano, halogen, amino, acyl, carboxyl, silyl, trifluoromethyl, C1-C50 alkylthio, C1-C50 alkoxy, C6-C50 aryloxy, C6-C50 arylthio, C1-C50 alkylamino, C1-C50 alkyl, C3-C50 cycloalkyl, C1-C50 heterocyclic alkyl, C6-C50 aryl, and C3-C50 aryl.

[0065] Preferably, Rb is selected from hydrogen, deuterium, cyano, halogen, amino, acyl, carboxyl, silyl, trifluoromethyl, substituted or unsubstituted C1-C25 alkathio, substituted or unsubstituted C1-C25 alkoxy, substituted or unsubstituted C6-C25 aryloxy, substituted or unsubstituted C6-C25 arylthio, substituted or unsubstituted C1-C25 alkylamino, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C25 cycloalkyl, substituted or unsubstituted C1-C25 heterocycloalkyl, substituted or unsubstituted C6-C25 aryl, and substituted or unsubstituted C3-C25 heteroaryl. The substituents in the substituted C1-C25 alkylthio, substituted C1-C25 alkoxy, substituted C6-C25 aryloxy, substituted C6-C25 arylthio, substituted C1-C25 alkylamino, substituted C1-C25 alkyl, substituted C3-C25 cycloalkyl, substituted C1-C25 heterocyclic alkyl, substituted C6-C25 aryl, and substituted C1-C25 heteroaryl are selected from one or more of deuterium, cyano, halogen, amino, acyl, carboxyl, silyl, trifluoromethyl, C1-C25 alkylthio, C1-C25 alkoxy, C6-C25 aryloxy, C6-C25 arylthio, C1-C25 alkylamino, C1-C25 alkyl, C3-C25 cycloalkyl, C1-C25 heterocyclic alkyl, C6-C25 aryl, and C3-C25 aryl.

[0066] Preferably, Rb is selected from hydrogen, deuterium, cyano, halogen, amino, acyl, carboxyl, silyl, trifluoromethyl, substituted or unsubstituted C1-C12 alkathio, substituted or unsubstituted C1-C12 alkoxy, substituted or unsubstituted C6-C12 aryloxy, substituted or unsubstituted C6-C12 arylthio, substituted or unsubstituted C1-C12 alkylamino, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C1-C12 heterocycloalkyl, substituted or unsubstituted C6-C12 aryl, and substituted or unsubstituted C3-C12 heteroaryl. The substituents in the substituted C1-C12 alkylthio, substituted C1-C12 alkoxy, substituted C6-C12 aryloxy, substituted C6-C12 arylthio, substituted C1-C12 alkylamino, substituted C1-C12 alkyl, substituted C3-C12 cycloalkyl, substituted C1-C12 heterocyclic alkyl, substituted C6-C12 aryl, and substituted C1-C12 heteroaryl are selected from one or more of deuterium, cyano, halogen, amino, acyl, carboxyl, silyl, trifluoromethyl, C1-C12 alkylthio, C1-C12 alkoxy, C6-C12 aryloxy, C6-C12 arylthio, C1-C12 alkylamino, C1-C12 alkyl, C3-C12 cycloalkyl, C1-C12 heterocyclic alkyl, C6-C12 aryl, and C3-C12 aryl.

[0067] Preferably, Rb is selected from one or more of hydrogen, deuterium, cyano, halogen, amino, acyl, carboxyl, silyl, trifluoromethyl, methyl, ethyl, tert-butyl, phenyl, naphthyl, biphenyl, phenylnaphthyl, naphthylphenyl, terphenyl, binaphthyl, pyridyl, pyrimidinyl, dibenzofuranyl, and dibenzothiopheneyl. Preferably, Rb is selected from hydrogen; Preferably, the fused ring compound has the structure shown in formula (6) to (7);

[0068] In the formula, Ar 1 Ar 2 The definition of L is as described above; Preferably, L is selected from substituted or unsubstituted C6-C50 arylene or substituted or unsubstituted C3-C50 heteroarylene; The substituents in the substituted C6-C50 arylene and substituted C3-C50 heteroarylene are selected from one or more of the following: deuterium, cyano, halogen, amino, acyl, carboxyl, silyl, trifluoromethyl, C1-C50 alkylthio, C1-C50 alkoxy, C6-C50 aryloxy, C6-C50 arylthio, C1-C50 alkylamino, C1-C50 alkyl, C3-C50 cycloalkyl, C1-C50 heterocycloalkyl, C6-C50 aryl, and C3-C50 aryl.

[0069] Preferably, L is selected from substituted or unsubstituted C6-C25 arylene or substituted or unsubstituted C3-C25 heteroarylene; The substituents in the substituted C6-C25 arylene and substituted C3-C25 heteroarylene are selected from one or more of the following: deuterium, cyano, halogen, amino, acyl, carboxyl, silyl, trifluoromethyl, C1-C25 alkylthio, C1-C25 alkoxy, C6-C25 aryloxy, C6-C25 arylthio, C1-C25 alkylamino, C1-C25 alkyl, C3-C25 cycloalkyl, C1-C25 heterocycloalkyl, C6-C25 aryl, and C3-C25 aryl.

[0070] Preferably, L is selected from substituted or unsubstituted C6-C12 arylene or substituted or unsubstituted C3-C12 heteroarylene; The substituents in the substituted C6-C12 arylene and substituted C3-C12 heteroarylene are selected from one or more of the following: deuterium, cyano, halogen, amino, acyl, carboxyl, silyl, trifluoromethyl, C1-C12 alkylthio, C1-C12 alkoxy, C6-C12 aryloxy, C6-C12 arylthio, C1-C12 alkylamino, C1-C12 alkyl, C3-C12 cycloalkyl, C1-C12 heterocycloalkyl, C6-C12 aryl, and C3-C12 aryl.

[0071] Preferably, L is selected from substituted or unsubstituted group D, wherein group D is selected from one of phenylene, naphthylene, biphenylene, binatylene, naphthylphenylene, phenylenenaphthylene, pyridylene, pyrimidinylene, dibenzofuranylene, and dibenzothiopheneylene; Wherein, the substituent in the substituted group D is selected from one or more of the following: deuterium, cyano, halogen, amino, acyl, carboxyl, silyl, trifluoromethyl, tert-butyl, methoxy, phenoxy, phenyl, naphthyl, biphenyl, pyridyl, and pyrimidinyl. Preferred, Ar 1 and Ar 2 Each is independently selected from substituted or unsubstituted C6-C50 aryl or substituted or unsubstituted C3-C50 heteroaryl; The substituents in the substituted C6-C50 aryl and substituted C3-C50 heteroaryl are selected from one or more of the following: deuterium, cyano, halogen, amino, acyl, carboxyl, silyl, trifluoromethyl, C1-C50 alkylthio, C1-C50 alkoxy, C6-C50 aryloxy, C6-C50 arylthio, C1-C50 alkylamino, C1-C50 alkyl, C3-C50 cycloalkyl, C1-C50 heterocycloalkyl, C6-C50 aryl, and C3-C50 aryl.

[0072] Preferred, Ar 1 and Ar 2 Each is independently selected from substituted or unsubstituted C6-C25 aryl or substituted or unsubstituted C3-C25 heteroaryl; The substituents in the substituted C6-C25 aryl and substituted C3-C25 heteroaryl are selected from one or more of the following: deuterium, cyano, halogen, amino, acyl, carboxyl, silyl, trifluoromethyl, C1-C25 alkylthio, C1-C25 alkoxy, C6-C25 aryloxy, C6-C25 arylthio, C1-C25 alkylamino, C1-C25 alkyl, C3-C25 cycloalkyl, C1-C25 heterocycloalkyl, C6-C25 aryl, and C3-C25 aryl.

[0073] Preferred, Ar 1 and Ar 2 Each is independently selected from substituted or unsubstituted C6-C12 aryl or substituted or unsubstituted C3-C12 heteroaryl; The substituents in the substituted C6-C12 aryl and substituted C3-C12 heteroaryl are selected from one or more of the following: deuterium, cyano, halogen, amino, acyl, carboxyl, silyl, trifluoromethyl, C1-C12 alkylthio, C1-C12 alkoxy, C6-C12 aryloxy, C6-C12 arylthio, C1-C12 alkylamino, C1-C12 alkyl, C3-C12 cycloalkyl, C1-C12 heterocycloalkyl, C6-C12 aryl, and C3-C12 aryl.

[0074] Preferred, Ar 1 and Ar 2 Each substituted or unsubstituted group E is independently selected from:

[0075]

[0076] ; Wherein, the substituent in the substituted group E is selected from one or more of the following: deuterium, cyano, halogen, amino, acyl, carboxyl, silyl, trifluoromethyl, pyridine, naphthyl, biphenyl, terphenyl, phenylnaphthyl, naphthylphenyl, pyridyl, pyrimidinyl, dibenzofuranyl, and dibenzothiophene.

[0077] Preferred, Ar 1 and Ar 2 Pyridyl groups that are not substituted with phenyl groups.

[0078] Preferably, the organic layer includes an n-type charge-generating layer.

[0079] Preferably, the charge generation layer comprises the n-type charge generation material described above or the structure shown in formula (1).

[0080] Preferably, the organic layer comprises one or more of a hole injection layer, a first organic light-emitting layer, a second organic light-emitting layer, and an electron injection layer; Preferably, the charge-generating layer is located between the first organic light-emitting layer and the second organic light-emitting layer.

[0081] Preferably, the charge generation layer comprises an n-type charge generation layer and a p-type charge generation layer, wherein the n-type charge generation layer comprises a structure as shown in formula (1).

[0082] Preferably, the n-type charge generation layer further comprises a metal dopant; the metal dopant is one or more of alkali metals, alkaline earth metals and rare earth metals, or one or more of metal alloys containing alkali metals, alkaline earth metals and rare earth metals.

[0083] Preferably, the metal dopant is selected from Li, Mg, or Yb, or any combination thereof.

[0084] Preferably, the p-type charge generation layer is not subject to any special restrictions and can be set in a conventional manner in the art and matched with the above-mentioned n-type charge generation layer.

[0085] More preferably, the p-type charge generation layer may be composed of HAT-CN and TCTA, and the present invention does not make any special setting on their ratio.

[0086] Preferably, the organic electroluminescent device may include a stacked anode, a hole injection layer, a first hole transport layer, a first electron blocking layer, a first organic light-emitting layer, a first hole blocking layer, a first electron transport layer, an n-type charge generation layer, a p-type charge generation layer, a second hole transport layer, a second electron blocking layer, a second organic light-emitting layer, a second hole blocking layer, a second electron transport layer, an electron injection layer, and a cathode.

[0087] Preferably, the organic layer comprises an electron transport layer, which has a structure as shown in formula (1).

[0088] Preferably, the organic electroluminescent device may include an anode, a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, and a cathode stacked together.

[0089] Preferably, the organic layer includes a hole-blocking layer, which has a structure as shown in formula (1).

[0090] Preferably, the organic electroluminescent device may include an anode, a hole injection layer, a hole transport layer, an electron blocking layer, a light-emitting layer, a hole blocking layer, an electron transport layer, an electron injection layer, and a cathode stacked together.

[0091] Preferably, the organic layer comprises an electron transport layer, which has a structure as shown in formula (1).

[0092] Preferably, the organic electroluminescent device may include an anode, a hole injection layer, a hole transport layer, an electron blocking layer, a light-emitting layer, a hole blocking layer, an electron transport layer, an electron injection layer, and a cathode stacked together.

[0093] Preferably, the anode comprises an anode material, preferably a material with a large work function that facilitates hole injection into the first hole transport layer. For example, the anode material may include: metals such as nickel, platinum, vanadium, chromium, copper, zinc, and gold, or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); combinations of metals and oxides such as ZnO:Al or SnO2:Sb; or conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDT), polypyrrole, and polyaniline, but is not limited thereto.

[0094] More preferably, the anode is selected as indium tin oxide (ITO).

[0095] Preferably, the hole injection layer is used to enhance the ability to inject holes into the first hole transport layer. The hole injection layer can be selected from benzidine derivatives, starburst-like aryl amine compounds, phthalocyanine derivatives, or other materials; the present invention does not impose any special limitations on this. The material of the hole injection layer can, for example, be selected from the following compounds or any combination thereof:

[0096] .

[0097] Optionally, the first hole transport layer / hole transport layer may include one or more hole transport materials. The first hole transport layer is a layer that receives holes from the first hole injection layer and transports the holes to the light-emitting layer. The hole transport layer material may be selected from carbazole polymers, carbazole-linked triarylamine compounds, or other types of compounds. This invention does not impose any special limitations on this. The material of the first hole transport layer may, for example, be selected from the following compounds or any combination thereof:

[0098] .

[0099] More preferably, the first hole transport layer may be composed of HT-1.

[0100] Preferably, the material of the first electron blocking layer is selected from conventional materials used in the art. An electron blocking layer refers to a layer disposed between the light-emitting auxiliary layer and the light-emitting layer to prevent electrons injected from the cathode from transferring to the light-emitting auxiliary layer and recombinating in the light-emitting layer; it can also be called an electron blocking layer or an electron suppression layer. The electron blocking layer is preferably made of a material with a lower electron affinity than the electron transport layer. This invention does not impose any special limitations in this regard.

[0101] More preferably, the first electron blocking layer / electron blocking layer may be composed of mCP.

[0102]

[0103] Preferably, the first organic light-emitting layer / light-emitting layer may include a blue light-emitting layer, a red light-emitting layer, or a green light-emitting layer, with a blue light-emitting layer being the most preferred. This invention does not impose any special limitations on the blue light-emitting layer; conventional blue light-emitting layer materials in the art can be used. For example, the host material for blue light emission can be an anthracene derivative, and the guest material can be a boron nitride (BN) resonant fluorescent material.

[0104] More preferably, the first organic light-emitting layer is composed of the following materials: .

[0105] Preferably, the material of the first hole blocking layer / hole blocking layer is selected from conventional materials in the art. The hole blocking layer is a layer disposed between the electron transport layer and the light-emitting layer to prevent holes injected by the anode from being transferred to the electron transport layer and recombination in the light-emitting layer; it can also be referred to as a hole suppression layer or hole blocking layer. The hole blocking layer is preferably made of a material with high ionization energy. The present invention does not impose any particular limitations in this regard.

[0106] More preferably, the material of the first hole-blocking layer shown is selected from BCP.

[0107] .

[0108] Preferably, the first electron transport layer / electron transport layer can be a single-layer structure or a multi-layer structure, and it can include one or more electron transport materials. The first electron transport layer can be selected from, but is not limited to, benzimidazole derivatives, oxadiazole derivatives, quinoxaline derivatives or other electron transport materials. The present invention does not impose any special limitations on this.

[0109] More preferably, the first electron transport layer is composed of 1,3,5-tris(1-phenyl-1H-benzimidazol-2-yl)benzene (TPBI) and lithium octahydroxyquinoline (LiQ).

[0110] .

[0111] Preferably, the second hole transport layer is not subject to any special restrictions and can adopt conventional settings in the field, such as referring to the settings of the first hole transport layer.

[0112] Preferably, the second electron blocking layer is not subject to any special restrictions and can be set in a conventional manner in the art, such as referring to the setting of the first electron blocking layer.

[0113] Preferably, the second organic light-emitting layer may include a blue light-emitting layer, a red light-emitting layer, or a green light-emitting layer, with a blue light-emitting layer being the most preferred. This invention does not impose any special limitations on the blue light-emitting layer; conventional blue light-emitting layer materials in the art can be used, for example, it can be configured similarly to the first organic light-emitting layer.

[0114] Preferably, the second hole blocking layer is not subject to any special restrictions and can adopt conventional settings in the field, such as referring to the settings of the first hole blocking layer.

[0115] Preferably, the second electron transport layer is not subject to any special restrictions and can adopt conventional settings in the field, such as referring to the settings of the first electron transport layer.

[0116] Preferably, the electron injection layer is used to enhance the ability to inject electrons into the second electron transport layer. The electron injection layer may include inorganic materials such as alkali metal sulfides and alkali metals, or may include complexes of alkali metals and organic materials.

[0117] More preferably, the electron-injected layer may include ytterbium (Yb).

[0118] Preferably, the cathode may comprise a cathode material that has a small work function and facilitates electron injection into the functional layers. Specific examples of cathode materials include, but are not limited to, metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead or alloys thereof; or multilayer materials such as LiF / Al, Liq / Al, LiO2 / Al, LiF / Ca, LiF / Al, and BaF2 / Ca.

[0119] The present invention also provides an organic electroluminescent device, the organic electroluminescent device comprising a cathode, an anode, and an organic layer located between the cathode and the anode, the organic layer comprising an electron transport layer comprising a fused ring compound as described above.

[0120] The present invention also provides an organic electroluminescent device, the organic electroluminescent device comprising a cathode, an anode, and an organic layer located between the cathode and the anode, the organic layer comprising a hole blocking layer comprising a fused ring compound as described above.

[0121] It should be noted that the above-mentioned organic electroluminescent devices are fabricated using conventional methods in the art, such as depositing layers on a substrate.

[0122] The present invention also provides an application of the above-described fused ring compound, or the above-described n-type charge generating layer, or the above-described electron transport layer, or the above-described hole blocking layer, or the above-described organic electroluminescent device in optical fiber equipment, lighting equipment, electrophotographic photosensitive equipment, photoelectric converters, organic solar cells, switching element equipment, organic light-emitting field-effect transistors, image sensors, or dye lasers.

[0123] The present invention also provides an organic electroluminescent product, which includes the above-described organic electroluminescent device.

[0124] The present invention also provides an electronic device comprising the above-described fused ring compound.

[0125] Preferably, the electronic devices include perovskite photovoltaic devices, perovskite light-emitting devices, display devices, organic integrated circuits, organic field-effect transistors, organic thin-film transistors, organic light-emitting transistors, organic solar cells, organic photodetectors, organic photoreceptors, organic field quenching devices, luminescent electrochemical cells, and organic laser diodes.

[0126] The above can be combined freely.

[0127] The beneficial effects of this invention are: The fused ring compound provided by the present invention, based on the structure of formula (1), further limits the types of substituents to improve the structural stability of the fused ring compound, and the HOMO and LUMO energy levels of the fused ring compound have a high degree of matching with the adjacent energy levels, so that the carrier mobility of the fused ring compound is more balanced, thereby enabling the organic electroluminescent device containing the fused ring compound to have a lower driving voltage, higher luminous efficiency and longer lifetime. The fused-ring compound provided by this invention is based on the structure of formula (1), and further, Ar 1 and Ar 2 The presence of heteroaryl groups can assist in coordination, thereby suppressing metal migration in the n-type charge generation layer of the multilayer organic light-emitting diode (OLED) and preventing metal from entering the p-type charge generation layer and affecting device stability. Therefore, the Ar1 and Ar2 coordination system based on heteroaryl groups can effectively improve the stability of the n-type charge generation layer. Simultaneously, the heteroatoms introduced into Ar1 and Ar2 can further lower the molecular energy level, resulting in a lower driving voltage for the multilayer organic light-emitting diode containing this fused-ring compound. Attached Figure Description

[0128] To more clearly illustrate the specific embodiments of the present invention or the technical solutions in the prior art, the drawings used in the description of the specific embodiments or the prior art will be briefly introduced below. Obviously, the drawings described below are some embodiments of the present invention. For those skilled in the art, other drawings can be obtained from these drawings without creative effort.

[0129] Figure 1 This is a structural diagram of the stacked organic electroluminescent device in the device embodiment of the present invention; 1-Anode, 2-Hole injection layer, 3-First hole transport layer, 4-First electron blocking layer, 5-First organic light-emitting layer, 6-First hole blocking layer, 7-First electron transport layer, 8-n-type charge generation layer, 9-p-type charge generation layer, 10-Second hole transport layer, 11-Second electron blocking layer, 12-Second organic light-emitting layer, 13-Second hole blocking layer, 14-Second electron transport layer, 15-Electron injection layer, 16-Cathode. Detailed Implementation

[0130] The following embodiments are provided to better understand the present invention and are not limited to the preferred embodiments described. They do not constitute a limitation on the content and scope of protection of the present invention. Any product that is the same as or similar to the present invention, derived by any person under the guidance of the present invention or by combining the features of the present invention with other prior art, falls within the protection scope of the present invention.

[0131] For experiments not specifically described in the examples, the procedures or conditions should be followed according to the conventional experimental procedures described in the literature in this field. Reagents or instruments whose manufacturers are not specified are all commercially available conventional reagent products.

[0132] When referring to material ratios, unless otherwise specified, the ratio refers to volume ratio.

[0133] Synthesis Example 1 This embodiment provides a method for synthesizing compound C-1, and the synthetic route is shown in the following reaction formula:

[0134] In a 2-liter three-necked flask, under nitrogen protection, add raw material CA-1 (0.30 mol), raw material CB-1 (0.14 mol), dioxane:water = 4:1 (600 mL:150 mL), tetraphenylphosphine palladium (1.44 mmol), potassium carbonate (0.43 mol), and 90... The reaction was carried out overnight at C. After the reaction was completed, water was added to quench the reaction, and the product was extracted with dichloromethane. The organic layer was dried with anhydrous magnesium sulfate to remove the organic solvent. The crude product was purified by slurry mixing with n-hexane:ethyl acetate = 2:1 (400 mL: 200 mL) to obtain intermediate C1-1 (yield 89.0%).

[0135] In a 500 mL three-necked flask, under nitrogen protection, intermediate C1-1 (37.38 mmol), starting material CC-1 (82.23 mmol), 200 mL of anhydrous toluene, and tetraphenylphosphine palladium (0.75 mmol) were added. The reaction was carried out overnight at C. After the reaction was completed, the product was directly filtered, and the filter cake was washed with water and ethanol to obtain the crude product. The crude product was then passed through a fast column in a mixed solvent (dichloromethane: n-hexane = 4:1) and recrystallized to give compound C-1 (yield 60.3%).

[0136] Elemental analysis: C 34 H 22N4, theoretical values: C, 83.93; H, 4.56; N, 11.51; measured values: C, 83.95; H, 4.55; N, 11.50; HRMS (ESI) m / z (M+): theoretical value: 486.18, measured value: 485.49.

[0137] Synthesis Example 2 This embodiment provides a method for synthesizing compound C-6, and the synthetic route is shown in the following reaction formula:

[0138] In a 2-liter three-necked flask, under nitrogen protection, add raw material CA-1 (0.25 mol), raw material CC-1 (0.24 mol), anhydrous toluene (500 mL), tetraphenylphosphine palladium (2.52 mmol), and 110... The reaction was carried out overnight at C. After the reaction was completed, water was added to quench the reaction, and the product was extracted with dichloromethane. The organic layer was dried with anhydrous magnesium sulfate to remove the organic solvent. The crude product was purified by column chromatography (dichloromethane: n-hexane = 2: 1) to obtain intermediate C6-1.

[0139] In a 500 mL three-necked flask, under nitrogen protection, intermediate C6-1 (83.09 mmol), and starting material CB-6 (37.77 mmol), dioxane:water = 4:1 (200 mL:40 mL), 1,1'-bis(diphenylphosphine)ferrocene palladium dichloride (30.529 mmol), potassium carbonate (0.11 mol), and 90 mL of other reagents were added. The reaction was carried out overnight at C. After the reaction was completed, water was added to quench the reaction, and the mixture was filtered. The filter cake was washed with ethanol, and the crude product was passed through a fast column chromatography with o-dichlorobenzene and recrystallized to give compound C-6 (yield 61.0%).

[0140] Elemental analysis: C 38 H 24 N4, theoretical values: C, 85.05; H, 4.51; N, 10.44; measured values: C, 85.07; H, 4.50; N, 10.43; HRMS (ESI) m / z (M+): theoretical value: 536.20, measured value: 535.45.

[0141] Synthesis Example 3 This embodiment provides a method for synthesizing compound C-15, and the synthetic route is shown in the following reaction formula:

[0142] In a 2-liter three-necked flask, under nitrogen protection, add 0.25 mol of CA-15 and 0.24 mol of CC-1, 500 mL of anhydrous toluene, and 2.52 mmol of tetraphenylphosphine palladium. The reaction was carried out overnight at C. After the reaction was completed, water was added to quench the reaction, and the product was extracted with dichloromethane. The organic layer was dried with anhydrous magnesium sulfate to remove the organic solvent. The crude product was purified by column chromatography (dichloromethane: n-hexane = 1: 1) to give intermediate C15-1 (yield 88.3%).

[0143] In a 500 mL three-necked flask, under nitrogen protection, intermediate C15-1 (83.09 mmol), starting material CB-1 (37.77 mmol), dioxane:water = 4:1 (200 mL:40 mL), 1,1'-bis(diphenylphosphine)ferrocene palladium dichloride (30.529 mmol), potassium carbonate (0.11 mol), and 90 mL of other reagents were added. The reaction was carried out overnight at C. After the reaction was completed, water was added to quench the reaction, and the mixture was filtered. The filter cake was washed with ethanol, and the crude product was passed through a fast column chromatography with o-dichlorobenzene and recrystallized to give compound C-15 (yield 65.0%).

[0144] Elemental analysis: C 34 H 22 N4, theoretical values: C, 83.93; H, 4.56; N, 11.51; measured values: C, 83.96; H, 4.54; N, 11.50; HRMS (ESI) m / z (M+): theoretical value: 486.18, measured value: 487.14.

[0145] Synthesis Example 4 This embodiment provides a method for synthesizing compound C-22, and the synthetic route is shown in the following reaction formula:

[0146] In a 2-liter three-necked flask, under nitrogen protection, add raw material CA-15 (0.25 mol), raw material CC-22 (0.24 mol), anhydrous toluene (500 mL), tetraphenylphosphine palladium (2.52 mmol), and 110 mL of other reagents. The reaction was carried out overnight at C. After the reaction was completed, water was added to quench the reaction, and the product was extracted with dichloromethane. The organic layer was dried with anhydrous magnesium sulfate to remove the organic solvent. The crude product was purified by column chromatography (dichloromethane: n-hexane = 1: 1) to give intermediate C22-1 (yield 84.5%).

[0147] In a 500 mL three-necked flask, under nitrogen protection, intermediate C22-1 (83.09 mmol), starting material CB-1 (37.77 mmol), dioxane:water = 4:1 (200 mL:40 mL), 1,1'-bis(diphenylphosphine)ferrocene palladium dichloride (30.529 mmol), potassium carbonate (0.11 mol), and 90 mL of other reagents were added. The reaction was carried out overnight at C. After the reaction was completed, water was added to quench the reaction, and the mixture was filtered. The filter cake was washed with ethanol, and the crude product was passed through a fast column chromatography with o-dichlorobenzene and recrystallized to give compound C-22 (yield 63.6%).

[0148] Elemental analysis: C 54 H 34 N4, theoretical value: C, 87.78; H, 4.64; N, 7.58; measured value: C, 87.79; H, 4.65; N, 7.56; HRMS (ESI) m / z (M+): theoretical value: 738.28, measured value: 739.22.

[0149] Synthesis Example 5 This embodiment provides a method for synthesizing compound C-27, and the synthetic route is shown in the following reaction formula:

[0150] In a 2-liter three-necked flask, under nitrogen protection, add raw material CA-15 (0.25 mol), raw material CC-27 (0.24 mol), anhydrous toluene (500 mL), tetraphenylphosphine palladium (2.52 mmol), and 110 mL of other reagents. The reaction was carried out overnight at C. After the reaction was completed, water was added to quench the reaction, and the product was extracted with dichloromethane. The organic layer was dried with anhydrous magnesium sulfate to remove the organic solvent. The crude product was purified by column chromatography (dichloromethane: n-hexane = 1: 1) to obtain intermediate C27-1.

[0151] In a 500 mL three-necked flask, under nitrogen protection, intermediate C27-1 (83.09 mmol), and starting material CB-1 (37.77 mmol), dioxane:water = 4:1 (200 mL:40 mL), 1,1'-bis(diphenylphosphine)ferrocene palladium dichloride (30.529 mmol), and potassium carbonate (0.11 mol) were added. The reaction was carried out overnight at C. After the reaction was completed, water was added to quench the reaction, and the mixture was filtered. The filter cake was washed with ethanol, and the crude product was passed through a fast column chromatography with o-dichlorobenzene and recrystallized to give compound C-27 (yield 64.3%).

[0152] Elemental analysis: C48 H 28 N6, theoretical values: C, 83.70; H, 4.10; N, 12.20; measured values: C, 83.72; H, 4.09; N, 12.19; HRMS (ESI) m / z (M+): theoretical value: 688.24, measured value: 689.22.

[0153] Synthesis Example 6 This embodiment provides a method for synthesizing compound C-34, and the synthetic route is shown in the following reaction formula:

[0154] In a 2-liter three-necked flask, under nitrogen protection, add 0.25 mol of CA-15 and 0.24 mol of CC-1, 500 mL of anhydrous toluene, and 2.52 mmol of tetraphenylphosphine palladium. The reaction was carried out overnight at C. After the reaction was completed, water was added to quench the reaction, and the product was extracted with dichloromethane. The organic layer was dried with anhydrous magnesium sulfate to remove the organic solvent. The crude product was purified by column chromatography (dichloromethane: n-hexane = 1: 1) to obtain intermediate C15-1.

[0155] In a 500 mL three-necked flask, under nitrogen protection, intermediate C15-1 (74.78 mmol), starting material CC-34 (33.99 mmol), 180 mL of anhydrous toluene, and tetraphenylphosphine palladium (275 mg, 0.24 mmol) were added. The reaction was carried out overnight at C. After the reaction was completed, the mixture was directly filtered, and the filter cake was washed with water and ethanol to obtain the crude product. The crude product was then passed through a fast column chromatography with o-dichlorobenzene and recrystallized to give intermediate C-34 (yield 74.3%).

[0156] Elemental analysis: C 33 H 21 N5, theoretical value: C, 81.29; H, 4.34; N, 14.36; measured value: C, 81.31; H, 4.33; N, 14.35; HRMS (ESI) m / z (M+): theoretical value: 487.18, measured value: 488.11.

[0157] Component example: Device Example 1 This embodiment provides an organic electroluminescent device, such as... Figure 1As shown, it includes, in sequence, an anode 1, a hole injection layer 2, a first hole transport layer 3, a first electron blocking layer 4, a first organic light-emitting layer 5, a first hole blocking layer 6, a first electron transport layer 7, an n-type charge generation layer 8, a p-type charge generation layer 9, a second hole transport layer 10, a second electron blocking layer 11, a second organic light-emitting layer 12, a second hole blocking layer 13, a second electron transport layer 14, an electron injection layer 15, and a cathode 16. Its device structure is as follows: anode (indium tin oxide (ITO)), hole injection layer (HIL), first hole transport layer (HTL-1), first electron blocking layer (EBL-1), first organic light-emitting layer (EML-1), first hole blocking layer (HBL-1), first electron transport layer (ETL-1), n-type charge generation layer (CGL-n), p-type charge generation layer (CGL-p), second hole transport layer (HTL-2), second electron blocking layer (EBL-2), second organic light-emitting layer (EML-2), second hole blocking layer (HBL-2), second electron transport layer (ETL-2), electron injection layer (EIL), and cathode.

[0158] The fabrication of the above-mentioned organic electroluminescent device includes the following steps: 1) Substrate cleaning: The glass substrate coated with transparent ITO was ultrasonically treated in an aqueous cleaning agent (the composition and concentration of the aqueous cleaning agent: ethylene glycol solvent ≤10wt%, triethanolamine ≤1wt%), then rinsed in deionized water, ultrasonically degreased in a mixed solvent of acetone and ethanol (volume ratio of acetone and ethanol 1:1), baked in a clean environment until all moisture was removed, and then cleaned with ultraviolet light and ozone.

[0159] 2) Preparation of the organic layer: The ITO transparent substrate was transferred to an evaporation equipment and vacuumed to 1×10⁻⁶. -6 Up to 2×10 -4 Pa, hole injection layer (HIL) / first hole transport layer (HTL-1) / first electron blocking layer (EBL-1) / first organic light-emitting layer (EML-1) / first hole blocking layer (HBL-1) / first electron transport layer (ETL-1) / n-type charge generation layer (CGL-n) / p-type charge generation layer (CGL-p) / second hole transport layer (HTL-2) / second electron blocking layer (EBL-2) / second organic light-emitting layer (EML-2) / second hole blocking layer (HBL-2) / second electron transport layer (ETL-2) / electron injection layer (EIL) / cathode (Mg:Ag mass ratio is 1:9) are deposited sequentially on the ITO anode film.

[0160] in: The anode is indium tin oxide (ITO, 10 nm thick); The hole injection layer (HIL) is made of HAT-CN:TCTA (10 nm thick); the mass ratio of HAT-CN to TCTA is 3:97. The material of the first hole transport layer (HTL-1) is TCTA (20 nm thick); The material of the first electron blocking layer (EBL-1) is mCP (thickness 5 nm); The first organic light-emitting layer (EML-1) is made of D and E in a mass ratio of 95:5 (thickness 20 nm); The material of the first hole blocking layer (HBL-1) is BCP (5 nm thick); The first electron transport layer (ETL-1) is made of TPBI and LiQ in a mass ratio of 9:1 (thickness 25 nm); The material of the n-type charge generation layer (CGL-n) is composed of compound C-1 and Yb from synthesis example 1, and its specific ratio and thickness are shown in Table 1. The p-type charge generation layer (CGL-p) is made of HAT-CN and TCTA in a mass ratio of 8:2 (thickness 10 nm). The material of the second hole transport layer (HTL-2) is TCTA (20 nm thick); The material of the second electron blocking layer (EBL-2) is mCP (thickness 5 nm); The second organic light-emitting layer (EML-2) is made of D and E in a mass ratio of 95:5 (thickness 20 nm); The material of the second hole blocking layer (HBL-2) is BCP (5 nm thick); The second electron transport layer (ETL-2) is made of TPBI and LiQ in a mass ratio of 9:1 (thickness 25 nm); The electron injection layer (EIL) is made of Yb (1 nm thick); The cathode is made of Mg and Ag in a mass ratio of 1:9 (thickness 11 nm).

[0161] Device Examples 2 to Device Examples 6 Device Examples 2 to 6 each provide an organic electroluminescent device, differing from Device Example 1 only in that compound C-1 in the n-type charge generation layer of Device Example 1 is replaced with the compounds obtained in Synthesis Examples 2 to 6. The composition and proportion of the compounds in the n-type charge generation layer of Device Examples 2 to 6 are detailed in Table 1.

[0162] Device Comparison Example 1 This comparative example provides an organic electroluminescent device, which differs from device example 1 only in that the compound C-1 in the n-type charge generation layer of device example 1 is replaced with compound REF-1 as shown below.

[0163]

[0164] Device Comparison Example 2 This comparative example provides an organic electroluminescent device, which differs from device example 1 only in that the compound C-1 in the n-type charge generation layer of device example 1 is replaced with compound REF-2 as shown below.

[0165]

[0166] REF-2 Device Comparison Example 3 This comparative example provides an organic electroluminescent device, which differs from device example 1 only in that the compound C-1 in the n-type charge generation layer of device example 1 is replaced with compound REF-3 as shown below.

[0167]

[0168] Table 1. Composition and thickness of n-type charge generation layer

[0169] The organic electroluminescent devices obtained in Device Examples 1-6 and Device Comparative Examples 1-3 in the device examples were tested.

[0170] Instruments: The current, voltage, brightness, emission spectrum and other characteristics of the device were tested simultaneously using a PR 625 spectral scanning luminance meter and a Keithley K 2400 digital source meter system; Test conditions: Photoelectric property test conditions: current density 10 mA / cm² 2 , room temperature.

[0171] Lifetime test: current density 10 mA / cm² 2 The recording time (in hours) is when the device brightness drops to 95% of its original brightness.

[0172] Among them, the lifetime and current efficiency of device comparison example 1 are set to 100. The test results of the lifetime and current efficiency of device examples 1 to 6, device comparison examples 2 and 3 relative to device comparison example 1 are shown in Table 2. The test results of the driving voltage of device examples 1 to 6 and device comparison examples 1-3 are shown in Table 2.

[0173] Table 2. Device performance parameters for Device Examples 1-6 and Device Comparative Examples 1-3

[0174] Device Example 7 This embodiment provides an organic electroluminescent device, comprising, in sequence, an anode, a hole injection layer, a hole transport layer, an electron blocking layer, an emissive layer, a hole blocking layer, an electron transport layer, an electron injection layer, and a cathode. The device structure is as follows: anode (indium tin oxide (ITO)), hole injection layer (HIL), hole transport layer (HTL), electron blocking layer (EBL), emissive layer (EML), hole blocking layer (HBL), electron transport layer (ETL), electron injection layer (EIL), and cathode.

[0175] The fabrication of the above-mentioned organic electroluminescent device includes the following steps: 1) Substrate cleaning: The glass substrate coated with transparent ITO was ultrasonically treated in an aqueous cleaning agent (the composition and concentration of the aqueous cleaning agent: ethylene glycol solvent ≤10wt%, triethanolamine ≤1wt%), then rinsed in deionized water, ultrasonically degreased in a mixed solvent of acetone and ethanol (volume ratio of acetone and ethanol 1:1), baked in a clean environment until all moisture was removed, and then cleaned with ultraviolet light and ozone.

[0176] 2) Preparation of the organic layer: The ITO transparent substrate was transferred to an evaporation equipment and vacuumed to 1×10⁻⁶. -6 Up to 2×10 -4 Pa, hole injection layer (HIL) / hole transport layer (HTL-1) / electron blocking layer (EBL-1) / light emitting layer (EML-1) / hole blocking layer (HBL-1) / electron transport layer (ETL-1) / electron injection layer (EIL) / cathode are sequentially deposited on the ITO anode film.

[0177] in: The anode is indium tin oxide (ITO, 10 nm thick). The hole injection layer (HIL) is made of HAT-CN:TCTA (10 nm thick); the mass ratio of HAT-CN to TCTA is 3:97. The hole transport layer (HTL) is made of TCTA (20 nm thick); The electron blocking layer (EBL) is made of mCP (5 nm thick); The light-emitting layer (EML) is made of D and E in a mass ratio of 95:5 (thickness 20 nm); The hole blocking layer (HBL) is made of compound C-1 (5 nm thick) from synthesis example 1; The electron transport layer (ETL) is made of TPBI and LiQ in a mass ratio of 9:1 (thickness 25 nm). The electron injection layer (EIL) is made of Yb (1 nm thick); The cathode is made of Mg and Ag in a mass ratio of 1:9 (thickness 11 nm).

[0178] Device Examples 8 to Device Examples 12 This embodiment provides an organic electroluminescent device, which differs from device embodiment 7 only in that compound C-1 in the hole blocking layer of device embodiment 7 is replaced with compounds from synthesis embodiments 2 to 6.

[0179] Device Comparison Example 4 This comparative example provides an organic electroluminescent device, which differs from device example 7 only in that the compound C-1 in the hole blocking layer of device example 7, synthesized in example 1, is replaced with compound REF-1 as shown below.

[0180]

[0181] The organic electroluminescent devices obtained in Device Examples 7-12 and Device Comparative Example 4 were tested.

[0182] Instruments: The current, voltage, brightness, emission spectrum and other characteristics of the device were tested simultaneously using a PR 625 spectral scanning luminance meter and a Keithley K 2400 digital source meter system; Test conditions: Photoelectric property test conditions: current density 10 mA / cm² 2 , room temperature.

[0183] Lifetime test: current density 10 mA / cm² 2 The recording time (in hours) is when the device brightness drops to 95% of its original brightness.

[0184] Among them, the lifetime and current efficiency of device comparison example 4 are set to 100. The test results of the lifetime and current efficiency of device examples 7 to 12 relative to device comparison example 4 are shown in Table 3. The test results of the driving voltage of device examples 7 to 12 and device comparison example 4 are also shown in Table 3.

[0185] Table 3. Device performance parameters of Device Examples 7-12 and Device Comparative Example 2

[0186] Device Example 13 This embodiment provides an organic electroluminescent device, comprising, in sequence, an anode, a hole injection layer, a hole transport layer, an electron blocking layer, an emissive layer, a hole blocking layer, an electron transport layer, an electron injection layer, and a cathode. The device structure is as follows: anode (indium tin oxide (ITO)), hole injection layer (HIL), hole transport layer (HTL), electron blocking layer (EBL), emissive layer (EML), hole blocking layer (HBL), electron transport layer (ETL), electron injection layer (EIL), and cathode.

[0187] The fabrication of the above-mentioned organic electroluminescent device includes the following steps: 1) Substrate cleaning: The glass substrate coated with transparent ITO was ultrasonically treated in an aqueous cleaning agent (the composition and concentration of the aqueous cleaning agent: ethylene glycol solvent ≤10wt%, triethanolamine ≤1wt%), then rinsed in deionized water, ultrasonically degreased in a mixed solvent of acetone and ethanol (volume ratio of acetone and ethanol 1:1), baked in a clean environment until all moisture was removed, and then cleaned with ultraviolet light and ozone.

[0188] 2) Preparation of the organic layer: The ITO transparent substrate was transferred to an evaporation equipment and vacuumed to 1×10⁻⁶. -6 Up to 2×10 -4 Pa, hole injection layer (HIL) / hole transport layer (HTL-1) / electron blocking layer (EBL-1) / light emitting layer (EML-1) / hole blocking layer (HBL-1) / electron transport layer (ETL-1) / electron injection layer (EIL) / cathode are sequentially deposited on the ITO anode film.

[0189] in: The anode is indium tin oxide (ITO, 10 nm thick); The hole injection layer (HIL) is made of HAT-CN:TCTA (10 nm thick); the mass ratio of HAT-CN to TCTA is 3:97. The hole transport layer (HTL) is made of TCTA (20 nm thick); The electron blocking layer (EBL) is made of mCP (5 nm thick); The light-emitting layer (EML) is made of D and E in a mass ratio of 95:5 (thickness 20 nm); The hole blocking layer (HBL) is made of BCP (5 nm thick); The electron transport layer (ETL) is made of C-1 and LiQ in synthesis example 1, with a mass ratio of 9:1 (thickness 25 nm); The electron injection layer (EIL) is made of Yb (1 nm thick); The cathode is made of Mg and Ag in a mass ratio of 1:9 (thickness 11 nm).

[0190] Device Examples 14 to 18 This embodiment provides an organic electroluminescent device, which differs from device embodiment 13 only in that compound C-1 in the electron transport layer of device embodiment 13 is replaced with compounds from synthesis embodiments 2 to 6.

[0191] Device Comparison Example 5 This comparative example provides an organic electroluminescent device, which differs from device example 13 only in that compound C-1 in the electron transport layer of device example 13 is replaced with compound REF-1.

[0192]

[0193] The organic electroluminescent devices obtained in Device Examples 13-18 and Device Comparative Example 5 were tested.

[0194] Instruments: The current, voltage, brightness, emission spectrum and other characteristics of the device were tested simultaneously using a PR 625 spectral scanning luminance meter and a Keithley K 2400 digital source meter system; Test conditions: Photoelectric property test conditions: current density 10 mA / cm² 2 The current density is 10 mA / cm². 2 , room temperature.

[0195] Lifetime test: current density 10 mA / cm² 2 The recording time (in hours) is when the device brightness drops to 95% of its original brightness.

[0196] The lifetime and current efficiency of device comparison example 5 are set to 100. The test results of the lifetime and current efficiency of device examples 13 to 18 relative to device comparison example 5 are shown in Table 4. The test results of the drive voltage of device examples 13 to 18 and device comparison example 5 are also shown in Table 4.

[0197] Table 4. Device performance parameters for Device Examples 13-18 and Device Comparative Example 5

[0198] Obviously, the above embodiments are merely illustrative examples for clear explanation and are not intended to limit the implementation. Those skilled in the art will recognize that other variations or modifications can be made based on the above description. It is neither necessary nor possible to exhaustively list all possible implementations here. However, obvious variations or modifications derived therefrom are still within the scope of protection of this invention.

Claims

1. A fused-ring compound, characterized in that, It has the structure shown in equation (1): In equation (1), Ra is selected from the structure shown in equation (A); L is selected from substituted or unsubstituted C6-C60 arylene, substituted or unsubstituted C3-C60 heteroarylene; Ar 1 and Ar 2 Each is independently selected from substituted or unsubstituted C3-C60 heteroaryl groups; In formula (A), Indicates a connection key; X1 and X2 are each independently selected from CRb or N, and at least one of X1 and X2 is selected from N; Rb is selected from hydrogen, deuterium, cyano, halogen, amino, acyl, carboxyl, silyl, trifluoromethyl, substituted or unsubstituted C1-C60 alkathio, substituted or unsubstituted C1-C60 alkoxy, substituted or unsubstituted C6-C60 aryloxy, substituted or unsubstituted C6-C60 arylthio, substituted or unsubstituted C1-C60 alkylamino, substituted or unsubstituted C1-C60 alkyl, substituted or unsubstituted C3-C60 cycloalkyl, substituted or unsubstituted C1-C60 heterocycloalkyl, substituted or unsubstituted C6-C60 aryl, and substituted or unsubstituted C3-C60 heteroaryl. Among them, substituted C1-C60 alkathioyl, substituted C1-C60 alkoxy, substituted C6-C60 aryloxy, substituted C6-C60 arylthio, substituted C1-C60 alkylamino, substituted C1-C60 alkyl, substituted C3-C60 cycloalkyl, substituted C1-C60 heterocycloalkyl, substituted C6-C60 aryl, substituted C3-C60 heteroaryl, substituted C6-C60 arylene, substituted The substituents in C3-C60 heteroaryl groups are selected from one or more of the following: deuterium, cyano, halogen, amino, acyl, carboxyl, silyl, trifluoromethyl, C1-C60 alkylthio, C1-C60 alkoxy, C6-C60 aryloxy, C6-C60 arylthio, C1-C60 alkylamino, C1-C60 alkyl, C3-C60 cycloalkyl, C1-C60 heterocycloalkyl, C6-C60 aryl, and C3-C60 aryl.

2. The fused-ring compound according to claim 1, characterized in that, The fused ring compound has the structures shown in formulas (2) to (4); In the formula, Ar 1 Ar 2 L, X1, and X2 are defined as described in claim 1.

3. A fused-ring compound according to claim 1 or 2, characterized in that, The fused ring compound has the structures shown in formulas (6) and (7); In the formula, Ar 1 Ar 2 L is defined as described in claim 1.

4. A fused-ring compound according to claim 1, 2, or 3, characterized in that, L is selected from substituted or unsubstituted C6-C12 arylene or substituted or unsubstituted C3-C12 heteroarylene; Wherein, the substituents in the substituted C6-C12 arylene and the substituted C3-C12 heteroarylene are selected from one or more of the following: deuterium, cyano, halogen, amino, acyl, carboxyl, silyl, trifluoromethyl, C1-C12 alkylthio, C1-C12 alkoxy, C6-C12 aryloxy, C6-C12 arylthio, C1-C12 alkylamino, C1-C12 alkyl, C3-C12 cycloalkyl, C1-C12 heterocycloalkyl, C6-C12 aryl, and C3-C12 aryl. Preferably, L is selected from substituted or unsubstituted group D, wherein group D is selected from one of phenylene, naphthylene, biphenylene, binatylene, naphthylphenylene, phenylenenaphthylene, pyridylene, pyrimidinylene, dibenzofuranylene, and dibenzothiopheneylene; Wherein, the substituent in the substituted group D is selected from one or more of the following: deuterium, cyano, halogen, amino, acyl, carboxyl, silyl, trifluoromethyl, tert-butyl, methoxy, phenoxy, phenyl, naphthyl, biphenyl, pyridyl, and pyrimidinyl.

5. A fused-ring compound according to any one of claims 1-4, characterized in that, Ar 1 and Ar 2 Each is independently selected from substituted or unsubstituted C3-C50 heteroaryl groups; The substituents in the substituted C3-C50 heteroaryl groups are selected from one or more of the following: deuterium, cyano, halogen, amino, acyl, carboxyl, silyl, trifluoromethyl, C1-C50 alkylthio, C1-C50 alkoxy, C6-C50 aryloxy, C6-C50 arylthio, C1-C50 alkylamino, C1-C50 alkyl, C3-C50 cycloalkyl, C1-C50 heterocycloalkyl, C6-C50 aryl, and C3-C50 aryl. Preferred, Ar 1 and Ar 2 Each is independently selected from substituted or unsubstituted C3-C25 heteroaryl groups; Wherein, the substituents in the substituted C3-C25 heteroaryl group are selected from one or more of the following: deuterium, cyano, halogen, amino, acyl, carboxyl, silyl, trifluoromethyl, C1-C25 alkylthio, C1-C25 alkoxy, C6-C25 aryloxy, C6-C25 arylthio, C1-C25 alkylamino, C1-C25 alkyl, C3-C25 cycloalkyl, C1-C25 heterocycloalkyl, C6-C25 aryl, and C3-C25 aryl. Preferred, Ar 1 and Ar 2 Each is independently selected from substituted or unsubstituted C3-C12 heteroaryl groups; The substituents in the substituted C3-C12 heteroaryl groups are selected from one or more of the following: deuterium, cyano, halogen, amino, acyl, carboxyl, silyl, trifluoromethyl, C1-C12 alkylthio, C1-C12 alkoxy, C6-C12 aryloxy, C6-C12 arylthio, C1-C12 alkylamino, C1-C12 alkyl, C3-C12 cycloalkyl, C1-C12 heterocycloalkyl, C6-C12 aryl, and C3-C12 aryl. Preferred, Ar 1 and Ar 2 Each substituted or unsubstituted group E is independently selected from: ； Wherein, the substituent in the substituted group E is selected from one or more of the following: deuterium, cyano, halogen, amino, acyl, carboxyl, silyl, trifluoromethyl, pyridine, naphthyl, biphenyl, terphenyl, phenylnaphthyl, naphthylphenyl, pyridyl, pyrimidinyl, dibenzofuranyl, and dibenzothiophene.

6. A fused-ring compound according to any one of claims 1-5, characterized in that, The fused-ring compound has the following structure: 。 7. An n-type charge-generating material, characterized in that, The n-type charge-generating material includes any one or a combination of at least two of the fused-ring compounds as described in any one of claims 1-6.

8. An electron transport material, characterized in that, The electron transport material comprises any one or a combination of at least two of the fused ring compounds as described in any one of claims 1-6.

9. A hole-blocking material, characterized in that, The hole-blocking material comprises any one or a combination of at least two of the fused ring compounds as described in any one of claims 1-6.

10. An organic electroluminescent device, characterized in that, The organic electroluminescent device includes a cathode, an anode, and an organic layer located between the cathode and the anode, the organic layer comprising a fused ring compound as described in any one of claims 1-6.

11. An organic electroluminescent device according to claim 10, characterized in that, The organic layer includes a charge-generating layer, the charge-generating layer comprising a fused-ring compound as described in any one of claims 1-6; Preferably, the organic layer comprises a hole-blocking layer, the hole-blocking layer comprising a fused ring compound as described in any one of claims 1-6; Preferably, the organic layer comprises an electron transport layer, the electron transport layer comprising a fused ring compound as described in any one of claims 1-6.

12. The application of a fused ring compound as described in any one of claims 1-6, an n-type charge-generating material as described in claim 7, an electron transport material as described in claim 8, a hole-blocking material as described in claim 9, or an organic electroluminescent device as described in claim 10 in optical fiber equipment, lighting equipment, electrophotographic photosensitive equipment, photoelectric converters, organic solar cells, switching element equipment, organic light-emitting field-effect transistors, image sensors, or dye lasers.

Images