A fused ring compound and use thereof

Abstract

The present application relates to the technical field of display, in particular to a fused ring compound and application thereof. The present application provides a fused ring compound, which has the following structure: 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 relates to the field of display technology, and more specifically to a fused ring compound and its applications. Background Technology

[0002] Organic electroluminescent materials are a new type of functional material with a rich variety of luminescent colors and a wide range of applications. They can be broadly categorized by function into luminescent materials, hole injection materials, hole transport materials, electron transport materials, and electron injection materials. Organic light-emitting diodes (OLEDs) fabricated using organic electroluminescent materials have a basic structure consisting of an anode, an organic layer, and a cathode. Their efficiency and lifetime are closely related to the device structure. OLEDs are devices that emit light through current-driven illumination and offer advantages such as thinness, flexibility, high contrast, wide color gamut, high plasticity, and low cost. Structurally, they can be classified into single-layer OLEDs and multilayer OLEDs. Stacked OLEDs connect two or more light-emitting units in series through a charge generation layer (connecting layer), thereby improving current efficiency, extending device lifespan, and meeting the brightness requirements for lighting applications. Stacked OLEDs are gradually becoming a research direction. They mainly consist of a first light-emitting stack, a second light-emitting stack, and a charge generation layer (CGL) placed between the first and second light-emitting stacks to ensure that the charge is effectively distributed to the light-emitting stacks while improving the current efficiency in each light-emitting layer.

[0003] However, existing charge generation layer materials have low stability and poor matching with other stacked materials, resulting in an imbalance in carrier mobility. This leads to problems such as high driving voltage, low luminous efficiency, and short lifetime in organic electroluminescent devices containing such organic electroluminescent materials, which severely limits the application of organic electroluminescent devices. Summary of the Invention

[0004] The purpose of this invention is to overcome the problem in the prior art that the matching degree between the existing charge generation layer and the stacked material is low, resulting in an imbalance of carrier mobility, which in turn causes the organic electroluminescent device containing the organic electroluminescent material to have a high driving voltage, low luminous efficiency and short lifetime. In this way, a fused ring compound and its application are provided.

[0005] In this invention, Indicates a connection key.

[0006] In this invention, the term "single bond" refers to the connection between two adjacent groups.

[0007] 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.

[0008] 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, one or a combination of at least two of the following: deuterium, halogen, cyano, C1-C12 alkyl, C3-C12 cycloalkyl, C6-C30 aryl, C3-C30 heteroaryl, C6-C60 arylamine, and C3-C60 heteroarylamine. 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 adjacent substituents Rc can exist independently or fuse with the functional group to which they are attached to form a ring.

[0009] In this invention, the term "halogen" refers to an atom selected from fluorine, chlorine, bromine, and iodine.

[0010] 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.

[0011] In this invention, the term "cycloalkyl" refers to a cyclic alkyl group consisting of at least 3 atoms. More specifically, it refers to a monocyclic or polycyclic hydrocarbon derived from a main chain of 3 to 60 carbon atoms, preferably 3 to 40 carbon atoms, and even more preferably 3 to 20 carbon atoms. Of course, the cycloalkyl group includes, but is not limited to, cyclopropyl, cyclobutyl, adamantyl, etc.

[0012] In this invention, the term "heterocyclic alkyl" includes one or more of O, S, Se, N, and Si as heteroatoms, and is a monocyclic or polycyclic ring having 1 to 60 carbon atoms, preferably 1 to 40 carbon atoms, and even more preferably 1 to 20 carbon atoms. Here, the 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, but it can also be another type of cyclic group, such as cycloalkyl, aryl, heteroaryl, etc.

[0013] 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 spiro structures. 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.

[0014] In this invention, the terms "heteroaryl" and "hybridoaryl" include monocyclic, polycyclic, or fused-ring heteroaryl groups, wherein the rings may be interrupted by short non-aromatic units, and the heteroatoms include nitrogen, oxygen, and sulfur. Heteroaryl groups include, but are not limited to, furanyl, phenylthio, pyrroleyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetraazinyl, triazolyl, tetraazolyl, furazolidyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, benzofuranyl, benzothiopheneyl, isobenzofuranyl, dibenzofuranyl, dibenzothiopheneyl, benzimidazolyl, and benzyl. Benzothiazolyl, benzoisothiazolyl, benzoisoxazolyl, benzoxazolyl, isoindolyl, indolyl, indazoleyl, benzothiadiazolyl, quinolinyl, isoquinolinyl, cenolinyl, quinazolinyl, quinoxalinyl, carbazoleyl, phenoxazinyl, phenthiazinyl, phenanthidyl, benzo[m]dioxacyclopentenyl, dihydroacridyl, and their derivatives; heteroaryl groups include, but are not limited to, furanyl, phenylthio, and pyrroleyl. Imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetrazinyl, triazolyl, tetrazolyl, furazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, benzofuranyl, benzothiophenyl, isobenzofuranyl, dibenzofuranyl, dibenzothiophenyl, benzimidazolyl Azolyl, benzothiazolyl, benzoisothiazolyl, benzoisoxazolyl, benzoxazolyl, isoindolyl, indolyl, ininazole, benzothiadiazolyl, quinolinyl, isoquinolinyl, cenolinyl, quinazolinyl, quinoxolinyl, carbazolyl, phenoxazinyl, phenthiazinyl, phenanthridyl, phenanthridyl, benzo[m]dioxacyclopentenyl, dihydroacridyl, and their derivatives, etc. As used herein, the term "substituted" means that a hydrogen atom in the compound is replaced by another substituent. This position is not limited to a specific position, as long as the hydrogen at that position can be replaced by a substituent. When two or more substituents are present, the two or more substituents can be the same or different.

[0015] In this invention, "C1-C60, C3-C60, C6-C60" defines the range of carbon atoms, indicating that the number of carbon atoms is any integer within the defined range. For example, C6-C60 aryl means that the number of carbon atoms in 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, 60.

[0016] The solution adopted in this invention is as follows:

[0017] This invention provides a fused-ring compound having the structure shown in formula (1):

[0018]

[0019] In equation (1),

[0020] L is selected from single bond, substituted or unsubstituted C6-C60 arylene, or substituted or unsubstituted C3-C60 heteroarylene;

[0021] Ar is selected from the structure shown in formula A:

[0022]

[0023] In formula A, X1 is selected from N or CR 1 X2 is selected from N or CR 2 X3 is selected from N or CR 3 X3 is selected from N or CR 4 X5 is selected from N or CR 5 X6 is selected from N or CR 6 ;

[0024] R 1 R 2 R 3 R 4 R 5 R 6 Each is independently selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C60 alkyl, substituted or unsubstituted C3-C60 cycloalkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl;

[0025] R 1 R 2 R 3 R4 R 5 R 6 They exist independently, or adjacent pairs can be connected to form substituted or unsubstituted C6-C60 aromatic rings or substituted or unsubstituted C3-C60 heteroaromatic rings;

[0026] The substituents of the substituted C6-C60 arylene, substituted C1-C60 heteroarylene, substituted C1-C60 alkyl, substituted C3-C60 cycloalkyl, substituted C6-C60 aryl, substituted C3-C60 heteroarylene, substituted C6-C60 aromatic ring, and substituted C3-C60 heteroarylene ring are selected from one or a combination of at least two of the following: deuterium, cyano, halogen, halide, amino, acyl, carboxyl, silyl, trifluoromethyl, methylthio, methoxy, C1-C60 alkyl, C3-C60 cycloalkyl, C1-C60 heterocycloalkyl, C6-C60 aryl, and C3-C60 heteroarylene.

[0027] Preferably, formula (1) is selected from the following structures:

[0028]

[0029] Preferably, formula A is selected from the following structures:

[0030]

[0031] Among them, R 1 ~R 31 Each is independently selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C60 alkyl, substituted or unsubstituted C3-C60 cycloalkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl;

[0032] n 23 Any integer selected from 0 to 2, which is understandable, n 23 It should be selected from any one of 0, 1, and 2;

[0033] n6、n 10 n 11 n 16 n 17 Each integer is independently selected from any integer between 0 and 3, which is understandable. n6, n 10 n 11 n 16 n 17 Each should be independently selected from 0, 1, 2, or 3;

[0034] n3, n4, n5, n7, n8, n9, n 15 n 21 n 22Each integer is independently selected from any integer between 0 and 4, which is understandable. n3, n4, n5, n7, n8, n9, n 15 n 21 n 22 Each of the numbers should be independently selected from 0, 1, 2, 3, and 4.

[0035] n 14 Any integer selected from 0 to 5, which is understandable, n 14 It should be selected from any one of 0, 1, 2, 3, 4, and 5;

[0036] n1、n 12 n 13 Each is independently selected from any integer between 0 and 6, which is understandable; n1, n 12 n 13 Each should be independently selected from any one of 0, 1, 2, 3, 4, 5, or 6;

[0037] n2、n 18 n 19 n 20 Each is independently selected from any integer between 0 and 7, which is understandable; n², n 18 n 19 n 20 Each should be independently selected from any one of 0, 1, 2, 3, 4, 5, 6, or 7.

[0038] Preferably, L is selected from single bond, substituted or unsubstituted C6-C30 arylene, or substituted or unsubstituted C3-C30 heteroarylene;

[0039] R 1 ~R 31 Each is independently selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl;

[0040] The substituents of the substituted C6-C30 arylene, substituted C3-C30 heteroarylene, substituted C1-C30 alkyl, substituted C3-C30 cycloalkyl, substituted C6-C30 aryl, and substituted C3-C30 heteroarylene are selected from one or a combination of at least two of the following: deuterium, cyano, halogen, halide, amino, acyl, carboxyl, silyl, trifluoromethyl, methylthio, methoxy, C1-C60 alkyl, C3-C60 cycloalkyl, C1-C60 heterocycloalkyl, C6-C60 aryl, and C3-C60 heteroarylene.

[0041] Preferably, L is selected from single bond, substituted or unsubstituted C6-C25 arylene, or substituted or unsubstituted C3-C25 heteroarylene;

[0042] R 1 ~R 31 Each is independently selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C25 cycloalkyl, substituted or unsubstituted C6-C25 aryl, substituted or unsubstituted C3-C25 heteroaryl;

[0043] The substituents of the substituted C6-C25 arylene, substituted C3-C25 heteroarylene, substituted C1-C25 alkyl, substituted C3-C25 cycloalkyl, substituted C6-C25 aryl, and substituted C3-C25 heteroaryl are selected from one or a combination of at least two of the following: deuterium, cyano, halogen, halide, amino, acyl, carboxyl, silyl, trifluoromethyl, methylthio, methoxy, C1-C60 alkyl, C3-C60 cycloalkyl, C1-C60 heterocycloalkyl, C6-C60 aryl, and C3-C60 heteroaryl.

[0044] Preferably, L is selected from single bonds, substituted or unsubstituted C6-C20 arylene groups, or substituted or unsubstituted C3-C20 heteroarylene groups;

[0045] R 1 ~R 31 Each is independently selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C20 aryl, substituted or unsubstituted C3-C20 heteroaryl;

[0046] The substituents of the substituted C6-C20 arylene, substituted C3-C20 heteroarylene, substituted C1-C20 alkyl, substituted C3-C20 cycloalkyl, substituted C6-C20 aryl, and substituted C3-C20 heteroaryl are selected from one or a combination of at least two of the following: deuterium, cyano, halogen, halide, amino, acyl, carboxyl, silyl, trifluoromethyl, methylthio, methoxy, C1-C60 alkyl, C3-C60 cycloalkyl, C1-C60 heterocycloalkyl, C6-C60 aryl, and C3-C60 heteroaryl.

[0047] Preferably, L is selected from single bond, substituted or unsubstituted C6-C15 arylene, or substituted or unsubstituted C3-C15 heteroarylene;

[0048] R 1 ~R 31Each is independently selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C15 aryl, substituted or unsubstituted C3-C15 heteroaryl.

[0049] The substituents of the substituted C6-C15 arylene, substituted C3-C15 heteroarylene, substituted C1-C15 alkyl, substituted C3-C15 cycloalkyl, substituted C6-C15 aryl, and substituted C3-C15 heteroaryl are selected from one or a combination of at least two of the following: deuterium, cyano, halogen, halide, amino, acyl, carboxyl, silyl, trifluoromethyl, methylthio, methoxy, C1-C60 alkyl, C3-C60 cycloalkyl, C1-C60 heterocycloalkyl, C6-C60 aryl, and C3-C60 heteroaryl.

[0050] Preferably, L is selected from single bonds, substituted or unsubstituted C6-C10 arylene groups, or substituted or unsubstituted C3-C10 heteroarylene groups;

[0051] R 1 ~R 31 Each is independently selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C6-C10 aryl, substituted or unsubstituted C3-C10 heteroaryl;

[0052] The substituents of the substituted C6-C10 arylene, substituted C3-C10 heteroarylene, substituted C1-C10 alkyl, substituted C3-C10 cycloalkyl, substituted C6-C10 aryl, and substituted C3-C10 heteroaryl are selected from one or a combination of at least two of the following: deuterium, cyano, halogen, halide, amino, acyl, carboxyl, silyl, trifluoromethyl, methylthio, methoxy, C1-C60 alkyl, C3-C60 cycloalkyl, C1-C60 heterocycloalkyl, C6-C60 aryl, and C3-C60 heteroaryl.

[0053] Preferably, L is selected from a single bond, a substituted or unsubstituted A group;

[0054] Wherein group A is selected from phenylene, naphthylene, phenanthrene, biphenylene, binatrimethylene, dibenzofuranyl, dibenzothiophene, benzonaphthiophene, benzonaphthiophene, spirofluorene, pyridinyl, phenanthrolinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, pyridinyl, pyridinyl, triazinyl, 4,5-diazonyl-9-one, and fluorenylene.

[0055] R 1 ~R 31Each group is independently selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted B groups;

[0056] The B group is selected from phenyl, naphthyl, phenanthryl, anthracene, fluoranthyl, pyrene, biphenyl, binatyl, terphenyl, phenylnaphthyl, naphthylphenyl, triphenylene, fluorenyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, spirodifluorenyl, 9,9-dimethylbenzofluorenyl, 9,9-diphenylbenzofluorenyl, cyclohexylfluorenyl, cyclopentylfluorenyl, benzospirodifluorenyl, benzofuranyl, dibenzofuranyl, naphthobenzofuranyl, dinaphthofuranyl, benzothiophene, dibenzothiophene. Naphthobenzothiophene, carbazolyl, N-phenylcarbazolyl, benzocarbazolyl, N-phenylbenzocarbazolyl, dibenzocarbazolyl, N-biphenylcarbazolyl, benzoxazolyl, naphthoxazolyl, phenanthrenexazolyl, phenanthrenebenzofuranyl, benzofuranobenzofuranyl, N-phenylbenzofuranocarbazolyl, pyridinyl, phenanthrolinel, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, pyridazinyl, pyrazinyl, pyrazinyl, triazinyl, 4,5-diazonyl-9-one, fluoranyl;

[0057] Wherein, the substituents in the substituted A group and the substituted B group are each independently selected from one or a combination of at least two of the following: deuterium, halogen, cyano, C1-C60 alkyl, C3-C60 cycloalkyl, C6-C60 aryl, C3-C60 heteroaryl, C6-C60 aromatic amino, and C3-C60 heteroarylamine.

[0058] Preferably, the substituents in the substituted A group and the substituted B group are each independently selected from deuterium, halogen, cyano, methyl, ethyl, propyl, adamantyl, cyclopropane, cyclohexyl, cyclopentyl, phenyl, naphthyl, phenanthrene, anthracene, fluoranyl, pyrene, biphenyl, binatyl, terphenyl, phenylnaphthyl, naphthylphenyl, triphenylene, fluorenyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, spirodifluorenyl, 9,9-dimethylbenzofluorenyl, 9,9-diphenylbenzofluorenyl, benzospirodifluorenyl, benzofuranyl, dibenzofuranyl, naphthobenzofuranyl. Dinaphthofuranyl, benzothiophenyl, dibenzothiophenyl, naphthobenzothiophenyl, carbazoyl, N-phenylcarbazoyl, benzocarbazoyl, N-phenylbenzocarbazoyl, dibenzocarbazoyl, N-biphenylcarbazoyl, benzoxazoleyl, naphthoxazoleyl, phenanthrenexazoleyl, phenanthrenebenzofuranyl, benzofuranobenzofuranyl, N-phenylbenzofuranocarbazoyl, pyridyl, phenanthrolinel, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, pyridazinyl, pyrazinyl, pyrazinyl, triazinyl, 4,5-diazonyl-9-one, fluoranyl, or a combination of at least two of these groups;

[0059] More preferably, the substituted A group may be selected from one or a combination of at least two of phenyl, naphthyl, fluorenyl, spirodifluorenyl, triphenyl, and phenylnaphthyl; the substituted B group may be selected from one or a combination of at least two of deuterium, phenyl, naphthyl, biphenyl, pyridyl, pyrimidinyl, quinolinyl, and 4,5-diazonyl-9-one.

[0060] Preferably, the fused-ring compound has the following structure:

[0061]

[0062]

[0063]

[0064] The present invention also provides a method for synthesizing the compound shown in formula (1), and the specific synthetic route is shown below.

[0065]

[0066] The present invention also provides an n-type charge generating material, wherein the n-type charge generating layer comprises one or a combination of at least two of the above-mentioned fused ring compounds.

[0067] The present invention also provides an electron transport material comprising one or a combination of at least two of the above-mentioned fused ring compounds.

[0068] The present invention also provides a hole-blocking material, wherein the hole-blocking material comprises one or a combination of at least two of the above-mentioned fused ring compounds.

[0069] 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 one or a combination of at least two of the above-mentioned fused ring compounds.

[0070] Preferably, the organic layer includes the above-described n-type charge generation layer;

[0071] Preferably, the n-type charge generation layer comprises the n-type charge generation material described above or one or a combination of at least two of the fused ring compounds described above.

[0072] And / or, the organic layer includes an electron transport layer as described above;

[0073] And / or, the organic layer includes a hole-blocking layer as described above.

[0074] Preferably, the electron transport layer comprises the electron transport material described above or one or a combination of at least two of the fused ring compounds described above.

[0075] Preferably, the hole-blocking layer comprises the hole-blocking material described above or one or a combination of at least two of the fused ring compounds described above.

[0076] 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;

[0077] Wherein, when the organic electroluminescent device includes an n-type charge generation layer, the n-type charge generation layer is located between the first organic light-emitting layer and the second organic light-emitting layer.

[0078] Preferably, the organic electroluminescent device may include an 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, all stacked together.

[0079] 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.

[0080] More preferably, the anode is selected as indium tin oxide (ITO).

[0081] 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 arylamine compounds, phthalocyanine derivatives or other materials. This application does not impose any special restrictions on this.

[0082] Optionally, the first 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 application does not impose any special limitations in this regard.

[0083] Preferably, the material of the first electron blocking layer is selected from conventional materials used in the art. An electron blocking layer is 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 a material with a lower electron affinity than the electron transport layer. This application does not impose any special limitations in this regard.

[0084] Preferably, the first 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 application 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.

[0085] Preferably, the material of the first 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 a hole blocking layer. The hole blocking layer is preferably made of a material with high ionization energy. This application does not impose any special limitations in this regard.

[0086] Preferably, the first 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. This application does not impose any special restrictions on this.

[0087] Preferably, the n-type charge generation layer may be composed of one or more of the compounds shown in formula (1) and the compounds shown in N-1 to N-87.

[0088] 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.

[0089] More preferably, the p-type charge generation layer may be composed of HAT-CN and TCTA, and the ratio of them is not specially set in this application.

[0090] 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.

[0091] 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.

[0092] 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 application 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.

[0093] 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.

[0094] 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.

[0095] 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 metal halides, or may include complexes of alkali metals and organic materials.

[0096] More preferably, the electron-injected layer may include ytterbium (Yb).

[0097] 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.

[0098] More preferably, the cathode may include a metal electrode containing magnesium and silver as the cathode, and the ratio of these components is not specifically set in this application.

[0099] 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.

[0100] The present invention also provides an organic electroluminescent product, which includes the above-described organic electroluminescent device.

[0101] The present invention also provides an electronic device comprising the above-described fused ring compound.

[0102] 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.

[0103] The above can be combined freely.

[0104] The beneficial effects of this invention are:

[0105] The organic compound containing fused rings provided by the present invention is based on the structure of formula (1). Further limiting Ar to have a specific structure of formula A can improve the structural stability of the compound. Moreover, the charge generation layer of the organic compound containing fused rings has a high degree of matching, so that the carrier mobility of the organic compound containing fused rings is more balanced. In this way, the organic electroluminescent device containing the organic compound containing fused rings has a lower driving voltage, higher luminous efficiency and longer lifetime.

[0106] Furthermore, the fused-ring compound provided by the present invention has good electron transport performance and can be used as an n-type charge generation material, an electron transport material, or a hole blocking material.

[0107] Furthermore, the present invention provides an organic electroluminescent device comprising a compound containing fused rings based on the structure of formula (1), thereby the organic electroluminescent device having a lower driving voltage, higher luminous efficiency and longer lifetime. Attached Figure Description

[0108] 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.

[0109] Figure 1 This is a structural diagram of the stacked organic electroluminescent device in the device embodiment of the present invention;

[0110] 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

[0111] 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.

[0112] 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.

[0113] Preparation of intermediate sub-1:

[0114]

[0115] Synthesis of intermediate sub-1: In a 10-liter single-necked flask, under reflux, starting material S-1 (0.78 mol), potassium hydroxide (2.31 mol), and water (1.20 L) were added. The mixture was stirred at 100 °C for 6 hours. Then, potassium permanganate aqueous solution (0.22 mmol, dissolved in 1.20 L of water) was added, and the mixture was stirred at 100 °C overnight. After the reaction was completed, the mixture was cooled to room temperature, and dichloromethane (1.00 L) was added. The reaction solution was filtered through diatomaceous earth to remove insoluble solids. The crude product was extracted with dichloromethane to remove the organic layer, dried with anhydrous sodium sulfate, and then evaporated to dryness to obtain intermediate sub-1 (yield 75.3%).

[0116] Preparation of intermediate sub-2:

[0117]

[0118] Synthesis of intermediate sub-2: The synthesis steps of intermediate sub-2 are the same as those of intermediate sub-1, except that the starting material S-1 is replaced with the starting material S-2, thus obtaining compound sub-2 (yield: 73.8%).

[0119] Synthesis example:

[0120] Synthesis Example 1: Synthesis of Compound N-1

[0121]

[0122] Synthesis of compound N-1: In a 250 mL three-necked flask under nitrogen protection, sub-1 (55.75 mmol), starting material a-1 (24.24 mmol), dioxane:water = 4:1 (120 mL:30 mL), 1,1'-bis(diphenylphosphine)ferrocene palladium dichloride (2.42 mmol), and potassium carbonate (121.20 mmol) were added. The reaction was carried out overnight at 95 °C. After the reaction was completed, sufficient water was added to quench the reaction. The crude product solid was filtered and passed through a fast column chromatography with o-dichlorobenzene. The recrystallization solution was used to obtain compound N-1 (yield 69.1%).

[0123] Elemental analysis: C 28 H 14N4O2; Theoretical values: C, 76.70; H, 3.22; N, 12.78; O, 7.30; Measured values: C, 76.72; H, 3.23; N, 12.76; HRMS(ESI) m / z [M+H]+: Theoretical value: 438.45; Measured value: 439.13.

[0124] Synthesis Example 2: Synthesis of Compound N-43:

[0125]

[0126] Synthesis of compound N-43: The synthesis method of compound N-43 is the same as that of compound N-1, except that the starting material a-1 is replaced with the starting material a-43, thus obtaining compound N-43 (yield 64.6%).

[0127] Elemental analysis: C 47 H 24 N4O2; Theoretical values: C, 83.42; H, 3.57; N, 8.28; O, 4.73; Measured values: C, 83.40; H, 3.56; N, 8.30; HRMS(ESI) m / z [M+H]+: Theoretical value: 676.74; Measured value: 677.89.

[0128] Synthesis Example 3: Synthesis of Compound N-3

[0129]

[0130] Synthesis of compound N-3: In a 250 mL three-necked flask under nitrogen protection, sub-1 (38.30 mmol), starting material a-3 (40.22 mmol), dioxane:water = 4:1 (120 mL:30 mL), 1,1'-bis(diphenylphosphine)ferrocene palladium dichloride (1.92 mmol), and potassium carbonate (95.75 mmol) were added. The reaction was carried out overnight at 95 °C. After the reaction was completed, sufficient water was added to quench the reaction. The crude product solid was filtered and passed through a fast column chromatography with o-dichlorobenzene. The recrystallization solution was used to obtain compound N-3 (yield 66.1%).

[0131] Elemental analysis: C 35 H 20 N4O; Theoretical values: C, 82.01; H, 3.93; N, 10.93; O, 3.12; Measured values: C, 82.00; H, 3.92; N, 10.95; HRMS(ESI) m / z [M+H]+: Theoretical value: 512.57; Measured value: 513.63.

[0132] Using intermediate sub-x, by changing the starting material an, and referring to the synthesis method used in synthesis example 3, the series of compounds listed in Table 1 can be obtained:

[0133] Table 1

[0134]

[0135]

[0136]

[0137]

[0138] The elemental analysis results of the compounds in Table 1 are shown in Table 2:

[0139] Table 2

[0140]

[0141]

[0142] Device Example

[0143] The materials used to fabricate the following device embodiments or device comparative examples are shown in Table 3 below:

[0144] Table 3

[0145]

[0146] Device Example 1-1

[0147] 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.

[0148] The fabrication of the above-mentioned organic electroluminescent device includes the following steps:

[0149] 1) Substrate cleaning:

[0150] 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.

[0151] 2) Preparation of organic layer:

[0152] The ITO transparent substrate was transferred to an evaporation equipment and vacuumed to 1×10⁻⁶. -6 Up to 2×10 -4 Pa, in sequence, deposited on the ITO anode film the following layers: 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).

[0153] in:

[0154] The anode is indium tin oxide (ITO, 10 nm thick);

[0155] 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.

[0156] The material of the first hole transport layer (HTL-1) is TCTA (20nm thick);

[0157] The material of the first electron blocking layer (EBL-1) is mCP (5nm thick);

[0158] The first organic light-emitting layer (EML-1) is made of D and E in a mass ratio of 95:5 (thickness 20nm);

[0159] The material of the first hole blocking layer (HBL-1) is BCP (5nm thick);

[0160] The first electron transport layer (ETL-1) is made of TPBI and LiQ in a mass ratio of 9:1 (thickness 25nm);

[0161] The material of the n-type charge generation layer (CGL-n) is composed of compounds N-1 and Yb from synthesis example 1, and the specific ratio and thickness are shown in Table 4.

[0162] The p-type charge generation layer (CGL-p) is made of HAT-CN and TCTA in a mass ratio of 8:2 (thickness 10nm);

[0163] The material of the second hole transport layer (HTL-2) is TCTA (20nm thick);

[0164] The material of the second electron blocking layer (EBL-2) is mCP (5nm thick);

[0165] The second organic light-emitting layer (EML-2) is made of D and E in a mass ratio of 95:5 (thickness 20nm);

[0166] The material of the second hole blocking layer (HBL-2) is BCP (5nm thick);

[0167] The second electron transport layer (ETL-2) is made of TPBI and LiQ in a mass ratio of 9:1 (thickness 25nm);

[0168] The electron injection layer (EIL) is made of Yb (1 nm thick);

[0169] The cathode is made of Mg and Ag in a mass ratio of 1:9 (thickness 11 nm).

[0170] Device Examples 1-2

[0171] Similar to Device Example 1-1, the difference is that compound N-1 in the n-type charge layer of Device Example 1-1 is replaced with compound N-43.

[0172] Device Examples 1-3

[0173] Similar to Device Example 1-1, the difference is that compound N-1 in the n-type charge layer of Device Example 1-1 is replaced with compound N-3.

[0174] Device Examples 1-4

[0175] Similar to Device Example 1-1, the difference is that compound N-1 in the n-type charge layer of Device Example 1-1 is replaced with compound N-4.

[0176] Device Examples 1-5

[0177] Similar to Device Example 1-1, the difference is that compound N-1 in the n-type charge layer of Device Example 1-1 is replaced with compound N-7.

[0178] Device Examples 1-6

[0179] Similar to Device Example 1-1, the difference is that compound N-1 in the n-type charge layer of Device Example 1-1 is replaced with compound N-34.

[0180] Device Examples 1-7

[0181] Similar to Device Example 1-1, the difference is that compound N-1 in the n-type charge layer of Device Example 1-1 is replaced with compound N-5.

[0182] Device Examples 1-8

[0183] Similar to Device Example 1-1, the difference is that compound N-1 in the n-type charge layer of Device Example 1-1 is replaced with compound N-9.

[0184] Device Examples 1-9

[0185] Similar to Device Example 1-1, the difference is that compound N-1 in the n-type charge layer of Device Example 1-1 is replaced with compound N-15.

[0186] Device Examples 1-10

[0187] Similar to Device Example 1-1, the difference is that compound N-1 in the n-type charge layer of Device Example 1-1 is replaced with compound N-20.

[0188] Device Examples 1-11

[0189] Similar to Device Example 1-1, the difference is that compound N-1 in the n-type charge layer of Device Example 1-1 is replaced with compound N-28.

[0190] Device Examples 1-12

[0191] Similar to Device Example 1-1, the difference is that compound N-1 in the n-type charge layer of Device Example 1-1 is replaced with compound N-33.

[0192] Device Examples 1-13

[0193] Similar to Device Example 1-1, the difference is that compound N-1 in the n-type charge layer of Device Example 1-1 is replaced with compound N-36.

[0194] Device Examples 1-14

[0195] Similar to Device Example 1-1, the difference is that compound N-1 in the n-type charge layer of Device Example 1-1 is replaced with compound N-39.

[0196] Device Examples 1-15

[0197] Similar to Device Example 1-1, the difference is that compound N-1 in the n-type charge layer of Device Example 1-1 is replaced with compound N-45.

[0198] Device Examples 1-16

[0199] Similar to Device Example 1-1, the difference is that compound N-1 in the n-type charge layer of Device Example 1-1 is replaced with compound N-64.

[0200] Device Examples 1-17

[0201] Similar to Device Example 1-1, the difference is that compound N-1 in the n-type charge layer of Device Example 1-1 is replaced with compound N-65.

[0202] Device Examples 1-18

[0203] Similar to Device Example 1-1, the difference is that compound N-1 in the n-type charge layer of Device Example 1-1 is replaced with compound N-66.

[0204] Device Examples 1-19

[0205] Similar to Device Example 1-1, the difference is that compound N-1 in the n-type charge layer of Device Example 1-1 is replaced with compound N-67.

[0206] Device Examples 1-20

[0207] Similar to Device Example 1-1, the difference is that compound N-1 in the n-type charge layer of Device Example 1-1 is replaced with compound N-68.

[0208] Device Examples 1-21

[0209] Similar to Device Example 1-1, the difference is that compound N-1 in the n-type charge layer of Device Example 1-1 is replaced with compound N-74.

[0210] Device Examples 1-22

[0211] Similar to Device Example 1-1, the difference is that compound N-1 in the n-type charge layer of Device Example 1-1 is replaced with compound N-76.

[0212] Device Examples 1-23

[0213] Similar to Device Example 1-1, the difference is that compound N-1 in the n-type charge layer of Device Example 1-1 is replaced with compound N-77.

[0214] Device Comparison Example 1-1

[0215] Similar to Device Example 1-1, the difference is that the compound N-1 in the n-type charge layer of Device Example 1-1 is replaced with compound REF-1.

[0216] Table 4. Composition and thickness of n-type charge generation layer

[0217] Device Example 1-1 N-1:Yb (mass ratio 95:5) / 10nm Device Examples 1-2 N-43:Yb (mass ratio 95:5) / 10nm Device Examples 1-3 N-3:Yb (mass ratio 95:5) / 10nm Device Examples 1-4 N-4:Yb (mass ratio 95:5) / 10nm Device Examples 1-5 N-7:Yb (mass ratio 95:5) / 10nm Device Examples 1-6 N-34: Yb (mass ratio 95:5) / 10nm Device Examples 1-7 N-5:Yb (mass ratio 95:5) / 10nm Device Examples 1-8 N-9:Yb (mass ratio 95:5) / 10nm Device Examples 1-9 N-15: Yb (mass ratio 95:5) / 10nm Device Examples 1-10 N-20: Yb (mass ratio 95:5) / 10nm Device Examples 1-11 N-28:Yb (mass ratio 95:5) / 10nm Device Examples 1-12 N-33:Yb (mass ratio 95:5) / 10nm Device Examples 1-13 N-36:Yb (mass ratio 95:5) / 10nm Device Examples 1-14 N-39:Yb (mass ratio 95:5) / 10nm Device Examples 1-15 N-45: Yb (mass ratio 95:5) / 10nm Device Examples 1-16 N-64: Yb (mass ratio 95:5) / 10nm Device Examples 1-17 N-65: Yb (mass ratio 95:5) / 10nm Device Examples 1-18 N-66:Yb (mass ratio 95:5) / 10nm Device Examples 1-19 N-67: Yb (mass ratio 95:5) / 10nm Device Examples 1-20 N-68: Yb (mass ratio 95:5) / 10nm Device Examples 1-21 N-74: Yb (mass ratio 95:5) / 10nm Device Examples 1-22 N-76: Yb (mass ratio 95:5) / 10nm Device Examples 1-23 N-77: Yb (mass ratio 95:5) / 10nm Device Comparison Example 1-1 REF-1: Yb (mass ratio 95:5) / 10nm

[0218] Test case

[0219] The organic electroluminescent devices obtained in Device Examples 1-1 to 1-23 and Device Comparative Example 1-1 were tested.

[0220] Instruments: The current, voltage, brightness, emission spectrum and other characteristics of the device were tested simultaneously using a PR 650 spectral scanning luminance meter and a Keithley K2400 digital source meter system;

[0221] Photoelectric property test conditions: current density 10 mA / cm² 2 , room temperature.

[0222] Lifetime test: current density 10mA / cm 2 Under the condition that the device brightness drops to 95% of the original brightness, the recording time (in hours) is recorded.

[0223] In Table 5, the lifetime T95 and current efficiency of the device comparative example 1-1 are set to 100. The lifetime T95 and current efficiency of the other device examples in Table 5 are relative values ​​to these values.

[0224] Table 5 Performance parameters of Device Examples 1-1 to 1-23 and Device Comparative Example 1-1

[0225]

[0226]

[0227] Device Example 2-1

[0228] 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.

[0229] The fabrication of the above-mentioned organic electroluminescent device includes the following steps:

[0230] 1) Substrate cleaning:

[0231] 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.

[0232] 2) Preparation of organic layer:

[0233] 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.

[0234] in:

[0235] The anode is indium tin oxide (ITO, 10 nm thick);

[0236] 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.

[0237] The hole transport layer (HTL) is made of TCTA (20 nm thick);

[0238] The electron blocking layer (EBL) is made of mCP (5 nm thick);

[0239] The materials of the light-emitting layer (EML) are D and E, with a mass ratio of 95:5 (thickness 20nm);

[0240] The hole blocking layer (HBL) is made of compound N-1 (5 nm thick) from synthesis example 1;

[0241] The electron transport layer (ETL) is made of TPBI and LiQ in a mass ratio of 9:1 (thickness 25nm);

[0242] The electron injection layer (EIL) is made of Yb (1 nm thick);

[0243] The cathode is made of Mg and Ag in a mass ratio of 1:9 (thickness 11 nm).

[0244] Device Example 2-2

[0245] Similar to Device Example 2-1, the difference is that compound N-1 in the hole blocking layer of Device Example 2-1 is replaced with compound N-3.

[0246] Device Examples 2-3

[0247] Similar to Device Example 2-1, the difference is that compound N-1 in the hole blocking layer of Device Example 2-1 is replaced with compound N-4.

[0248] Device Examples 2-4

[0249] Similar to Device Example 2-1, the difference is that compound N-1 in the hole blocking layer of Device Example 2-1 is replaced with compound N-5.

[0250] Device Examples 2-5

[0251] Similar to Device Example 2-1, the difference is that compound N-1 in the hole blocking layer of Device Example 2-1 is replaced with compound N-20.

[0252] Device Examples 2-6

[0253] Similar to Device Example 2-1, the difference is that compound N-1 in the hole blocking layer of Device Example 2-1 is replaced with compound N-36.

[0254] Device Examples 2-7

[0255] Similar to Device Example 2-1, the difference is that compound N-1 in the hole blocking layer of Device Example 2-1 is replaced with compound N-65.

[0256] Device Examples 2-8

[0257] Similar to Device Example 2-1, the difference is that compound N-1 in the hole blocking layer of Device Example 2-1 is replaced with compound N-74.

[0258] Device Examples 2-9

[0259] Similar to Device Example 2-1, the difference is that compound N-1 in the hole blocking layer of Device Example 2-1 is replaced with compound N-76.

[0260] Device Examples 2-10

[0261] Similar to Device Example 2-1, the difference is that compound N-1 in the hole blocking layer of Device Example 2-1 is replaced with compound N-77.

[0262] Device Comparison Example 2-1

[0263] Similar to Device Example 2-1, the difference is that compound N-1 in the hole blocking layer of Device Example 2-1 is replaced with compound REF-1.

[0264] The organic electroluminescent devices obtained in Device Examples 2-1 to 2-10 and Device Comparative Example 2-1 were tested.

[0265] Instruments: The current, voltage, brightness, emission spectrum and other characteristics of the device were tested simultaneously using a PR 650 spectral scanning luminance meter and a Keithley K2400 digital source meter system;

[0266] Photoelectric property test conditions: current density 10 mA / cm² 2 , room temperature.

[0267] Lifetime test: current density 10mA / cm 2 Under the condition that the device brightness drops to 95% of the original brightness, the recording time (in hours) is recorded.

[0268] In Table 6, the lifetime T95 and current efficiency of the device comparative example 2-1 are set to 100, and the lifetime T95 and current efficiency of the other device examples in Table 6 are relative values ​​of it.

[0269] Table 6. Device performance parameters of Device Examples 2-1 to 2-10 and Device Comparative Example 2-1

[0270]

[0271]

[0272] Device Example 3-1

[0273] 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.

[0274] The fabrication of the above-mentioned organic electroluminescent device includes the following steps:

[0275] 1) Substrate cleaning:

[0276] 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.

[0277] 2) Preparation of organic layer:

[0278] 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.

[0279] in:

[0280] The anode is indium tin oxide (ITO, 10 nm thick);

[0281] 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.

[0282] The hole transport layer (HTL) is made of TCTA (20 nm thick);

[0283] The electron blocking layer (EBL) is made of mCP (5 nm thick);

[0284] The materials of the light-emitting layer (EML) are D and E, with a mass ratio of 95:5 (thickness 20nm);

[0285] The hole blocking layer (HBL) is made of BCP (5nm thick);

[0286] The electron transport layer (ETL) is made of N-1 and LiQ in synthesis example 1, with a mass ratio of 9:1 (thickness 25 nm);

[0287] The electron injection layer (EIL) is made of Yb (1 nm thick);

[0288] The cathode is made of Mg and Ag in a mass ratio of 1:9 (thickness 11 nm).

[0289] Device Example 3-2

[0290] Similar to Device Example 3-1, the difference is that compound N-1 in the electron transport layer of Device Example 3-1 is replaced with compound N-3.

[0291] Device Example 3-3

[0292] Similar to Device Example 3-1, the difference is that compound N-1 in the electron transport layer of Device Example 3-1 is replaced with compound N-34.

[0293] Device Examples 3-4

[0294] Similar to Device Example 3-1, the difference is that compound N-1 in the electron transport layer of Device Example 3-1 is replaced with compound N-9.

[0295] Device Examples 3-5

[0296] Similar to Device Example 3-1, the difference is that compound N-1 in the electron transport layer of Device Example 3-1 is replaced with compound N-36.

[0297] Device Examples 3-6

[0298] Similar to Device Example 3-1, the difference is that compound N-1 in the electron transport layer of Device Example 3-1 is replaced with compound N-45.

[0299] Device Examples 3-7

[0300] Similar to Device Example 3-1, the difference is that compound N-1 in the electron transport layer of Device Example 3-1 is replaced with compound N-65.

[0301] Device Examples 3-8

[0302] Similar to Device Example 3-1, the difference is that compound N-1 in the electron transport layer of Device Example 3-1 is replaced with compound N-74.

[0303] Device Examples 3-9

[0304] Similar to Device Example 3-1, the difference is that compound N-1 in the electron transport layer of Device Example 3-1 is replaced with compound N-76.

[0305] Device Examples 3-10

[0306] Similar to Device Example 3-1, the difference is that compound N-1 in the electron transport layer of Device Example 3-1 is replaced with compound N-77.

[0307] Device Comparison Example 3-1

[0308] Similar to Device Example 3-1, the difference is that compound N-1 in the electron transport layer of Device Example 3-1 is replaced with compound REF-1.

[0309] The organic electroluminescent devices obtained in Device Examples 3-1 to 3-10 and Device Comparative Example 3-1 were tested.

[0310] Instruments: The current, voltage, brightness, emission spectrum and other characteristics of the device were tested simultaneously using a PR 650 spectral scanning luminance meter and a Keithley K 2400 digital source meter system;

[0311] Photoelectric property test conditions: current density 10 mA / cm² 2 , room temperature.

[0312] Lifetime test: current density 10mA / cm 2 Under the condition that the device brightness drops to 95% of the original brightness, the recording time (in hours) is recorded.

[0313] In Table 7, the lifetime T95 and current efficiency of the device comparative example 3-1 are set to 100. The lifetime T95 and current efficiency of the other device examples in Table 7 are relative values ​​to it.

[0314] Table 7 Performance parameters of Device Examples 3-1 to 3-10 and Device Comparative Example 3-1

[0315] Device Example 3-1 3.47 113.60 115.3 Device Example 3-2 3.49 112.98 113.9 Device Example 3-3 3.51 112.21 114.3 Device Examples 3-4 3.48 113.81 115.2 Device Examples 3-5 3.46 114.10 115.6 Device Examples 3-6 3.58 109.61 111.3 Device Examples 3-7 3.58 109.03 111.5 Device Examples 3-8 3.46 115.3 115.7 Device Examples 3-9 3.98 105.2 105.3 Device Examples 3-10 4.11 102.3 103.1 Device Comparison Example 3-1 4.53 100 100

[0316] 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 (1-1): In equation (1-1), L is selected from substituted or unsubstituted C6-C30 arylene groups; The substituents of the substituted C6-C30 arylene groups are selected from deuterium. Ar can be selected from any of the following structures: R 1 ~R 5 R 7 ~R 31 Each is independently selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C6-C30 aryl, or substituted or unsubstituted C3-C30 heteroaryl; n1~n 23 Each value is independently selected from zero to the largest possible integer value; The substituents of the substituted C1-C30 alkyl, substituted C6-C30 aryl, and substituted C3-C30 heteroaryl are selected from one or a combination of at least two of deuterium, C6-C60 aryl, and C3-C60 heteroaryl.

2. The fused-ring compound according to claim 1, characterized in that, L is selected from substituted or unsubstituted A groups; Wherein group A is selected from phenylene, naphthylene, phenanthrene, biphenylene, and binatylene; In this case, the substituent of the substituted A group is selected from deuterium; R 1 ~R 5 R 7 ~R 31 Each group is independently selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted B groups; The B group is selected from phenyl, naphthyl, phenanthryl, anthracene, fluoranthyl, pyrene, biphenyl, binatyl, terphenyl, phenylnaphthyl, naphthylphenyl, triphenylene, fluorenyl, 9,9-diphenylfluorenyl, spirodifluorenyl, 9,9-diphenylbenzofluorenyl, benzospirodifluorenyl, benzofuranyl, dibenzofuranyl, naphthobenzofuranyl, dinaphthofuranyl, benzothiophene, dibenzothiophene, naphthobenzothiophene. Carbazolyl, N-phenylcarbazolyl, benzo[carbazolyl], N-phenylbenzo[carbazolyl], dibenzo[carbazolyl], N-biphenylcarbazolyl, benzo[oxazolyl], naphtho[oxazolyl], phenanthrene[oxazolyl], phenanthrenebenzofuranyl, benzofuran[benzofuranyl], N-phenylbenzofuran[carbazolyl], pyridyl, phenanthrolinel, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, pyridazinyl, pyrazinyl, triazinyl; In this case, the substituents in the substituted B group are each independently selected from one or a combination of at least two of the following: deuterium, C6-C60 aryl, and C3-C60 heteroaryl.

3. The fused-ring compound according to claim 2, characterized in that, The substituents in the substituted B group are each independently selected from deuterium, phenyl, naphthyl, phenanthryl, anthracene, fluoranyl, pyrene, biphenyl, naphthyl, terphenyl, phenylnaphthyl, naphthylphenyl, triphenylene, fluorenyl, 9,9-diphenylfluorenyl, spirodifluorenyl, 9,9-diphenylbenzofluorenyl, benzospirodifluorenyl, benzofuranyl, dibenzofuranyl, naphthobenzofuranyl, dinaphthofuranyl, benzothiophene, dibenzothiophene, naphthobenzothiophene The group consisting of one or more of the following: α-carbazolyl, N-phenylcarbazolyl, benzo[a]carbazolyl, N-phenylbenzo[a]carbazolyl, dibenzo[a]carbazolyl, N-biphenylcarbazolyl, benzo[a]oxazolyl, naphtho[a]oxazolyl, phenanthrene[a]oxazolyl, phenanthrenebenzofuranyl, benzofuran[a]benzofuranyl, N-phenylbenzofuran[a]carbazolyl, pyridyl, phenanthrolinel, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, pyridazinyl, pyrazinyl, pyrimidinyl, and triazinyl.

4. The fused-ring compound according to any one of claims 1-3, characterized in that, The fused ring compound is selected from any of the following structures: 。 5. 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 1-4.

6. 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 1-4.

7. 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 1-4.

8. 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, wherein the organic layer includes any one or a combination of at least two of the fused-ring compounds according to any one of claims 1-4.

9. The organic electroluminescent device according to claim 8, characterized in that, The organic layer includes an n-type charge generation layer, which includes the n-type charge generation material as described in claim 5.

10. The organic electroluminescent device according to claim 8, characterized in that, The organic layer includes an electron transport layer, which includes the electron transport material as described in claim 6.

11. The organic electroluminescent device according to claim 8, characterized in that, The organic layer includes a hole-blocking layer, which includes the hole-blocking material as described in claim 7.

12. The application of the organic electroluminescent device according to any one of claims 8-11 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.

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