Condensed ring compound and application thereof

Abstract

The invention relates to the technical field of display, in particular to a fused ring compound and application thereof. The condensed ring compound provided by the invention has the following structure: the organic electroluminescent device containing the condensed ring compound can have lower driving voltage, higher luminous efficiency and longer service life.

Description

TECHNICAL FIELD

[0001] The present application relates to the technical field of display, in particular to a fused ring compound and application thereof. BACKGROUND

[0002] Organic electroluminescent material is a new type of functional material, which has rich luminescent color and wide application background. According to the function, it can be roughly divided into luminescent material, hole injection material, hole transport material, electron transport material, electron injection material and the like. Organic electroluminescent device (Organic Light Emitting Diode, OLED) prepared by using organic electroluminescent material has a basic structure including anode, organic layer and cathode, and the efficiency and service life are closely related to the device structure. It is a device driven by current to achieve the purpose of light emission, which has the advantages of lightness, flexibility, high contrast, wide color gamut, high plasticity, low cost and the like. From the structure, it can be divided into single-layer OLED and stacked OLED. The stacked OLED is to connect two or more light-emitting units together through a charge generation layer (connecting layer), so as to improve the current efficiency, prolong the service life of the device, meet the brightness of the lighting use, and gradually become the research direction. The main part includes the first light-emitting stack, the second light-emitting stack and the charge generation layer (CGL) arranged between the first light-emitting stack and the second light-emitting stack, so as to ensure that the charges are effectively distributed to the light-emitting stack and improve the current efficiency in each light-emitting layer.

[0003] However, the existing charge generation layer material has low stability and low matching degree with other stack materials, which causes the problem of unbalanced carrier mobility, and further causes the problems of high driving voltage, low luminous efficiency and short service life of the organic electroluminescent device containing the organic electroluminescent material, which seriously limits the application of the organic electroluminescent device. SUMMARY

[0004] The present application aims to overcome the problem of low matching degree between the existing charge generation layer and the stack material in the prior art, which causes the problem of unbalanced carrier mobility, and further provides a fused ring compound and application thereof.

[0005] In the present application, represents a connecting bond.

[0006] In the present application, the term "single bond" refers to a connecting bond between two adjacent groups.

[0007] In the present application, the term "substituent" has the usual meaning known in the art, which refers to a chemical moiety covalently attached to or, where appropriate, fused to the parent nucleus group.

[0008] In the present application, the term "substituted or unsubstituted" means that the functional group recited after the term can or can not have a substituent (hereinafter, the substituent will be collectively referred to as Rcfor convenience of description). For example, "substituted or unsubstituted aryl" means aryl having a substituent Rc, or non-substituted aryl. The substituent Rc, i.e., the above-mentioned substituent, for example, can be one or a combination of at least two of deuterium, a halogen, a cyano group, a C1-C12 alkyl group, a C3-C12 cycloalkyl group, a C6-C30 aryl group, a C3-C30 heteroaryl group, a C6-C60 arylamine group, and a C3-C60 heteroarylamine group, and optionally, for example, deuterium, a halogen group, a cyano group, an alkyl group, a haloalkyl group, a trialkylsilyl group, a deuterated alkyl group, an aryl group, a heteroaryl group, and the like. Of course, the number of substituents Rc can be one or more. When two substituents Rc are connected 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 substituents Rc exist adjacent to each other on a functional group, the adjacent substituents Rc can exist independently or be fused with the functional group to which they are connected to form a ring.

[0009] In the present application, the term "halogen" means an atom selected from the group consisting of fluorine, chlorine, bromine, and iodine.

[0010] In the present application, the term "alkyl" whether used as part of another term or alone, means a saturated hydrocarbon group, which can be straight-chained or branched. The term "C1-C60 alkyl" is derived from a monovalent substituent of a straight-chained or branched saturated hydrocarbon having 1 to 60 carbon atoms, preferably 1 to 40 carbon atoms, and more preferably 1 to 20 carbon atoms, and of course, examples thereof include, but are not limited to, methyl, ethyl, propyl, isobutyl, sec-butyl, t-butyl, pentyl, isopentyl, and hexyl.

[0011] In the present application, the term "cycloalkyl" means a cyclic system alkyl group consisting of at least 3 atoms, and further means a mononuclear or polynuclear hydrocarbon derived from a monocyclic or polycyclic hydrocarbon having 3 to 60 ring backbone carbon atoms, preferably 3 to 40 carbon atoms, and more preferably 3 to 20 carbon atoms, and of course, the cycloalkyl group includes, but is not limited to, cyclopropyl, cyclobutyl, adamantyl, and the like.

[0012] In the present application, the term "heterocycloalkyl" includes one or more of O, S, Se, N, and Si as a heteroatom, and has a monocyclic or polycyclic ring having 1 to 60 carbon atoms, preferably 1 to 40 carbon atoms, and more preferably 1 to 20 carbon atoms, and here, the polycyclic ring means a group in which the heterocycloalkyl group is directly connected to another ring group or fused with another ring group. Here, the other ring group can also be a heterocycloalkyl group, but can also be another ring group, such as a cycloalkyl group, an aryl group, a heteroaryl group, and the like.

[0013] In the present invention, the term "aryl" and "arylene" includes monocyclic, polycyclic or fused ring aryl, which can be interrupted by short non-aromatic units between the rings, and can contain a spiro structure, aryl includes but is not limited to phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, anthryl, fluorenyl, spirobifluorenyl, etc., arylene includes but is not limited to phenylene, biphenylene, terphenylene, naphthylene, phenanthrylene, anthrylene, fluorenylene, spirobifluorenylene, etc., wherein arylene refers to a divalent or multivalent group formed by further losing one or more hydrogen atoms from aryl.

[0014] In the present invention, the term "heteroaryl" and "heteroarylene" includes monocyclic, polycyclic or fused ring heteroaryl, which can be interrupted by short non-aromatic units between the rings, and the heteroatom includes nitrogen, oxygen, sulfur. Heteroaryl includes but is not limited to furanyl, thiophenyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetrazinyl, triazolyl, tetrazolyl, furazanyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, benzofuranyl, benzothiophenyl, isobenzofuranyl, dibenzofuranyl, dibenzothiophenyl, benzimidazolyl, benzothiazolyl, benzoisothiazolyl, benzoisoxazolyl, benzoaxazolyl, isoindolyl, indolyl, indazolyl, benzothiadiazolyl, quinolinyl, isoquinolinyl, cinnolinyl, quinazolinyl, quinoxalinyl, carbazolyl, phenoxazinyl, phenothiazinyl, phenanthridinyl, benzodioxolyl, dihydroacridinyl, and derivatives thereof, etc.; heteroarylene includes but is not limited to furanylene, thiophenylene, pyrrolylene, imidazolylene, pyrazolylene, thiazolylene, thiadiazolylene, isothiazolylene, isoxazolylene, oxazolylene, oxadiazolylene, triazinylene, tetrazinylene, triazolylene, tetrazolylene, furazanylene, pyridylene, pyrazinylyene, pyrimidinylyene, pyridazinylyene, benzofuranylene, benzothiophenylene, isobenzofuranylene, dibenzofuranylene, dibenzothiophenylene, benzimidazolylene, benzothiazolylene, benzoisothiazolylene, benzoisoxazolylene, benzoaxazolylene, isoindolylene, indolylene, indazolylene, benzothiadiazolylene, quinolinylene, isoquinolinylene, cinnolinylene, quinazolinylene, quinoxalinylene, carbazolylene, phenoxazinylene, phenothiazinylene, phenanthridinylene, benzodioxolylyene, dihydroacridinylene, and derivatives thereof, etc. As used in the present invention, the term "substituted" means that a hydrogen atom in the compound is substituted by another substituent. The position is not limited to a specific position, as long as the hydrogen at that position can be substituted by a substituent. When two or more substituents appear, the two or more substituents can be the same or different.

[0015] In the present invention, "C1-C60, C3-C60, C6-C60" defines the range of the number of carbon atoms, which means any integer within the defined range, for example, C6-C60 aryl, the number of carbon atoms of aryl can be any integer within the range of 6-60, for example, 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 scheme employed in the present invention is as follows:

[0017] The present invention provides a fused ring compound, having the structure shown in the following formula (1):

[0018]

[0019] In formula (1),

[0020] L is selected from a 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 are each 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 each independently exists, or two adjacent ones can be connected into a substituted or unsubstituted C6-C60 aryl ring, a substituted or unsubstituted C3-C60 heteroaryl ring;

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

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

[0028]

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

[0030]

[0031] wherein R 1 ~R 31 each independently is 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 is selected from any integer from 0 to 2, and it is understood that n 23 should be selected from any one of 0, 1, 2;

[0033] n6, n 10 , n 11 , n 16 , n 17 each independently is selected from any integer from 0 to 3, and it is understood that n6, n 10 , n 11 , n 16 , n 17 should each independently be selected from any one of 0, 1, 2, 3;

[0034] n3, n4, n5, n7, n8, n9, n 15 , n 21 , n 22each independently selected from any integer between 0 and 4, and it is understood that n3, n4, n5, n7, n8, n9, n 15 , n 21 , n 22 , should each independently be selected from any integer between 0, 1, 2, 3, 4;

[0035] n 14 is selected from any integer between 0 and 5, and it is understood that n 14 should be selected from any integer between 0, 1, 2, 3, 4, 5;

[0036] n1, n 12 , n 13 each independently selected from any integer between 0 and 6, and it is understood that n1, n 12 , n 13 should each independently be selected from any integer between 0, 1, 2, 3, 4, 5, 6;

[0037] n2, n 18 , n 19 , n 20 each independently selected from any integer between 0 and 7, and it is understood that n2, n 18 , n 19 , n 20 should each independently be selected from any integer between 0, 1, 2, 3, 4, 5, 6, 7.

[0038] Preferably, L is selected from a single bond, a substituted or unsubstituted C6-C30arylene, or a substituted or unsubstituted C3-C30heteroarylene;

[0039] R 1 ~ R 31 each independently selected from hydrogen, deuterium, halogen, cyano, a substituted or unsubstituted C1-C30alkyl, a substituted or unsubstituted C3-C30cycloalkyl, a substituted or unsubstituted C6-C30aryl, a substituted or unsubstituted C3-C30heteroaryl;

[0040] wherein the substituents of the substituted C6-C30arylene, the substituted C3-C30heteroarylene, the substituted C1-C30alkyl, the substituted C3-C30cycloalkyl, the substituted C6-C30aryl, the substituted C3-C30heteroaryl are selected from one or a combination of two or more of deuterium, cyano, halogen, halide, amino, acyl, carboxyl, silyl, trifluoromethyl, methylthio, methoxy, C1-C60alkyl, C3-C60cycloalkyl, C1-C60heterocycloalkyl, C6-C60aryl, C3-C60heteroaryl.

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

[0042] R 1 ~R 31 each 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] wherein the substituents of the substituted C6-C25 arylene, substituted C3-C25 heteroarylene, substituted C1-C25 alkyl, substituted C3-C25 cycloalkyl, substituted C6-C25 aryl, substituted C3-C25 heteroaryl are selected from one or a combination of at least two of deuterium, cyano, halogen, halide, amino, acyl, carboxyl, silyl, trifluoromethyl, methylthio, methoxy, C1-C60 alkyl, C3-C60 cycloalkyl, C1-C60 heterocycloalkyl, C6-C60 aryl, C3-C60 heteroaryl.

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

[0045] R 1 ~R 31 each 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] wherein the substituents of the substituted C6-C20 arylene, substituted C3-C20 heteroarylene, substituted C1-C20 alkyl, substituted C3-C20 cycloalkyl, substituted C6-C20 aryl, substituted C3-C20 heteroaryl are selected from one or a combination of at least two of deuterium, cyano, halogen, halide, amino, acyl, carboxyl, silyl, trifluoromethyl, methylthio, methoxy, C1-C60 alkyl, C3-C60 cycloalkyl, C1-C60 heterocycloalkyl, C6-C60 aryl, C3-C60 heteroaryl.

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

[0048] R 1 ~R 31each 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] wherein the substituents of substituted C6-C15 aryl, substituted C3-C15 heteroaryl, substituted C1-C15 alkyl, substituted C3-C15 cycloalkyl, substituted C6-C15 aryl, substituted C3-C15 heteroaryl are selected from one or a combination of at least two of deuterium, cyano, halogen, halide, amino, acyl, carboxyl, silyl, trifluoromethyl, methylthio, methoxy, C1-C60 alkyl, C3-C60 cycloalkyl, C1-C60 heterocycloalkyl, C6-C60 aryl, C3-C60 heteroaryl.

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

[0051] R 1 ~R 31 each 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] wherein the substituents of substituted C6-C10 aryl, substituted C3-C10 heteroaryl, substituted C1-C10 alkyl, substituted C3-C10 cycloalkyl, substituted C6-C10 aryl, substituted C3-C10 heteroaryl are selected from one or a combination of at least two of deuterium, cyano, halogen, halide, amino, acyl, carboxyl, silyl, trifluoromethyl, methylthio, methoxy, C1-C60 alkyl, C3-C60 cycloalkyl, C1-C60 heterocycloalkyl, C6-C60 aryl, C3-C60 heteroaryl.

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

[0054] wherein the A group is selected from phenylene, naphthylene, phenanthrylene, biphenylene, binaphthylene, dibenzofuranylene, dibenzothiophenylene, benzophenanthrolylene, benzobinaphthylene, spirofluorenylene, pyridylene, phenanthrolinylene, quinolinylene, isoquinolinylene, quinoxalinylene, quinazolinylene, pyridazinylene, pyrimidinylene, pyrazinylene, triazinylene, 4,5-diazafluorenylene-9-ketonylene, fluoranthrylene;

[0055] R 1 ~R 31each independently selected from the group consisting of hydrogen, deuterium, halogen, cyano, a substituted or unsubstituted B group;

[0056] wherein the B group is selected from the group consisting of phenyl, naphthyl, phenanthryl, anthryl, fluoranthenyl, pyrenyl, biphenyl, binaphthyl, terphenyl, phenylnaphthyl, naphthylphenyl, triphenylenyl, fluorenyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, spirobifluorenyl, 9,9-dimethylbenzofluorenyl, 9,9-diphenylbenzofluorenyl, cyclohexylfluorenyl, cyclopentylfluorenyl, benzospirofluorenyl, benzofuranyl, dibenzofuranyl, naphthobenzofuranyl, dinaphthofuranyl, benzothiophenyl, dibenzothiophenyl, naphthobenzothiophenyl, carbazolyl, N-phenylcarbazolyl, benzocarbazolyl, N-phenylbenzocarbazolyl, dibenzocarbazolyl, N-biphenylcarbazolyl, benzoxazolyl, naphthoxazolyl, phenanthroxazolyl, phenanthrobenzofuranyl, benzofurobenzofuranyl, N-phenylbenzofurocarbazolyl, pyridyl, phenanthrolinyl, quinolyl, isoquinolyl, quinoxalyl, quinazolyl, pyridazinyl, pyrimidinyl, pyrazinyl, triazinyl, 4,5-diazanphthoxen-9-one, fluoranthenyl;

[0057] wherein the substituents of the substituted A group, the substituted B group are each independently selected from one or a combination of at least two of deuterium, halogen, cyano, C1-C60 alkyl, C3-C60 cycloalkyl, C6-C60 aryl, C3-C60 heteroaryl, C6-C60 arylamine, C3-C60 heteroarylamine;

[0058] Preferably, the substituents of the substituted A group, the substituted B group are each independently selected from one or a combination of at least two of deuterium, halogen, cyano, methyl, ethyl, propyl, adamantyl, cyclopropanyl, cyclohexyl, cyclopentyl, phenyl, naphthyl, phenanthryl, anthryl, fluoranthenyl, pyrenyl, biphenyl, binaphthyl, terphenyl, phenylnaphthyl, naphthylphenyl, triphenylenyl, fluorenyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, spirobifluorenyl, 9,9-dimethylbenzofluorenyl, 9,9-diphenylbenzofluorenyl, benzospirofluorenyl, benzofuranyl, dibenzofuranyl, naphthobenzofuranyl, dinaphthofuranyl, benzothiophenyl, dibenzothiophenyl, naphthobenzothiophenyl, carbazolyl, N-phenylcarbazolyl, benzocarbazolyl, N-phenylbenzocarbazolyl, dibenzocarbazolyl, N-biphenylcarbazolyl, benzoxazolyl, naphthoxazolyl, phenanthroxazolyl, phenanthrobenzofuranyl, benzofurobenzofuranyl, N-phenylbenzofurocarbazolyl, pyridyl, phenanthrolinyl, quinolyl, isoquinolyl, quinoxalyl, quinazolyl, pyridazinyl, pyrimidinyl, pyrazinyl, triazinyl, 4,5-diazanphthoxen-9-one, fluoranthenyl;

[0059] More preferably, the substituted A group can be selected from one or a combination of at least two of phenyl, naphthyl, fluorenyl, spirobifluorenyl, terphenyl, phenyl naphthyl; and the substituted B group can be selected from one or a combination of at least two of deuterium, phenyl, naphthyl, biphenyl, pyridyl, pyrimidyl, quinolyl, 4,5-diazofluorene-9-ketone.

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

[0061]

[0062]

[0063]

[0064] The present application also provides a synthesis method of the compound shown in formula (1), and the specific synthesis route is shown as follows.

[0065]

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

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

[0068] The present application 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 application also provides an organic electroluminescent device, wherein the organic electroluminescent device comprises a cathode, an anode, and an organic layer between the cathode and the anode, and the organic layer comprises one or a combination of at least two of the above-mentioned fused ring compounds.

[0070] Preferably, the organic layer comprises the above-mentioned n-type charge generation layer.

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

[0072] And / or, the organic layer comprises the above-mentioned electron transport layer.

[0073] And / or, the organic layer comprises the above-mentioned hole blocking layer.

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

[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 first electron blocking layer material is selected from the conventional setting in the art, the electron blocking layer means a layer arranged between the light-emitting auxiliary layer and the light-emitting layer to prevent the electrons injected from the cathode from being transferred to the light-emitting auxiliary layer without recombination in the light-emitting layer, which can also be called an electron stopping layer or an electron inhibiting layer. The electron blocking layer is preferably a material having a smaller electron affinity than the electron transport layer. The present application does not make special restrictions thereon.

[0084] Preferably, the first organic light-emitting layer can include a blue light-emitting layer, a red light-emitting layer, or a green light-emitting layer, preferably a blue light-emitting layer. The present application does not make special restrictions on the blue light-emitting layer, and the conventional blue light-emitting layer material in the art can be used, for example, the blue light-emitting host material can be selected from anthracene derivatives, and the guest material can be selected from B-N resonance type fluorescent materials.

[0085] Preferably, the material of the first hole blocking layer is selected from the conventional setting in the art, the hole blocking layer is a layer arranged between the electron transport layer and the light-emitting layer to prevent the holes injected from the anode from being transferred to the electron transport layer without recombination in the light-emitting layer, which can also be called a hole inhibiting layer or a hole stopping layer. The hole blocking layer is preferably a material having a high ionization energy. The present application does not make special restrictions thereon.

[0086] Preferably, the first electron transport layer can be a single-layer structure or a multi-layer structure, and can include one or more electron transport materials, which can be selected from, but not limited to, benzimidazole derivatives, oxadiazole derivatives, quinoxaline derivatives, or other electron transport materials, and the present application does not make special restrictions thereon.

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

[0088] Preferably, the p-type charge generation layer is not specially limited, and the conventional setting in the art can be used and matched with the above-mentioned n-type charge generation layer.

[0089] More preferably, the p-type charge generation layer can be composed of HAT-CN and TCTA, and the present application does not make special settings for the proportion thereof.

[0090] Preferably, the second hole transport layer is not specially limited, and the conventional setting in the art can be used, for example, it can be set with reference to the first hole transport layer.

[0091] Preferably, the second electron blocking layer is not specially limited, and the conventional setting in the art can be used, for example, it can be set with reference to the first electron blocking layer.

[0092] Preferably, the second organic light-emitting layer can comprise a blue light-emitting layer, a red light-emitting layer, or a green light-emitting layer, preferably a blue light-emitting layer. The present application does not make special restrictions on the blue light-emitting layer, and a conventional blue light-emitting layer material in the art can be used, for example, which can be set with reference to the first organic light-emitting layer.

[0093] Preferably, the second hole-blocking layer does not make special restrictions, and a conventional setting in the art can be used, for example, which can be set with reference to the first hole-blocking layer.

[0094] Preferably, the second electron-transporting layer does not make special restrictions, and a conventional setting in the art can be used, for example, which can be set with reference to the first electron-transporting layer.

[0095] Preferably, the electron-injecting layer is used to enhance the ability of injecting electrons into the second electron-transporting layer. The electron-injecting layer can comprise inorganic materials such as alkali metal sulfides and alkali metal halides, or can comprise complexes of alkali metals and organic substances.

[0096] More preferably, the electron-injecting layer can comprise ytterbium (Yb).

[0097] Preferably, the cathode can comprise a cathode material, which is a material with small work function that is helpful for electron injection into the functional layer. Specific examples of the cathode material include, but are not limited to, metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead or their alloys; or multi-layer materials such as LiF / Al, Liq / Al, LiO2 / Al, LiF / Ca, LiF / Al, and BaF2 / Ca.

[0098] More preferably, the cathode can comprise a metal electrode comprising magnesium and silver as the cathode, and the present application does not make special settings for the proportion thereof.

[0099] It should be noted that the above-mentioned organic electroluminescent device is prepared by conventional means in the art, for example, each layer can be deposited on the substrate.

[0100] The present application also provides an organic electroluminescent product comprising the above-mentioned organic electroluminescent device.

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

[0102] Preferably, the electronic device comprises a perovskite photovoltaic device, a perovskite light-emitting device, a display device, an organic integrated circuit, an organic field effect transistor, an organic thin film transistor, an organic light-emitting transistor, an organic solar cell, an organic photodetector, an organic photoreceptor, an organic quenching device, a light-emitting electrochemical cell, and an organic laser diode.

[0103] The above can be freely combined.

[0104] The beneficial effects of the present application are as follows:

[0105] The organic compound containing a fused ring provided by the present application has a structure based on formula (1), and further has a specific structure of formula A for Ar, so that the stability of the compound is improved, and the charge generation layer of the organic compound containing a fused ring has a higher matching degree, so that the carrier mobility of the organic compound containing a fused ring is more balanced, and thus the organic electroluminescent device containing the organic compound containing a fused ring has a lower driving voltage, a higher luminous efficiency and a longer service life.

[0106] Further, the organic compound containing a fused ring provided by the present application 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] Further, the organic electroluminescent device provided by the present application comprises an organic compound containing a fused ring based on formula (1), and thus the organic electroluminescent device has a lower driving voltage, a higher luminous efficiency and a longer service life. BRIEF DESCRIPTION OF DRAWINGS

[0108] In order to more clearly illustrate the specific embodiments of the present application or the technical solutions in the prior art, the drawings needed in the following specific embodiments or prior art description will be briefly introduced. Obviously, the drawings in the following description are some embodiments of the present application, and other drawings can also be obtained by those skilled in the art without creative labor.

[0109] FIG. 1 Structure diagram of the stacked organic electroluminescent device in the device embodiment of the present application;

[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 DESCRIPTION

[0111] The following embodiments are provided to better further understand the present application, and are not limited to the best embodiments, and do not limit the content and protection scope of the present application. Any person who obtains any product the same as or similar to the present application under the inspiration of the present application or by combining the present application with other prior art features falls within the protection scope of the present application.

[0112] The specific experimental procedures or conditions are not mentioned in the examples, according to the operation or conditions of the conventional experimental procedures described in the literature in the field. The reagents or instruments used are not specified by the manufacturer, which are conventional reagent products that can be obtained by purchase.

[0113] Preparation of intermediate sub-1:

[0114]

[0115] Synthesis of intermediate sub-1: In a 10 liter single neck flask, under heating and refluxing conditions, add raw material S-1 (0.78 mol), and potassium hydroxide (2.31 mol), water (1.20 L), stir at 100°C for 6 hours, add potassium permanganate aqueous solution (0.22 mmol, dissolved in 1.20 L water), stir at 100°C overnight, after the reaction is completed, cool to room temperature, add dichloromethane (1.00 L), filter the reaction solution with diatomite, remove the insoluble solid, extract the organic layer with dichloromethane, dry with anhydrous sodium sulfate, and spin dry 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 raw material S-1 is replaced by raw material S-2, i.e. compound sub-2 (yield: 73.8%) is obtained.

[0119] Synthesis example:

[0120] Synthesis of compound N-1:

[0121]

[0122] Synthesis of compound N-1: In a 250 ml three-neck flask, under nitrogen protection, add sub-1 (55.75 mmol), and raw material a-1 (24.24 mmol), dioxane: water = 4:1 (120 mL:30 mL), 1,1'-bis(diphenylphosphino)ferrocene palladium dichloride (2.42 mmol), potassium carbonate (121.20 mmol), 95°C reaction overnight, after the reaction is completed, add enough water to quench, filter the crude product solid, and recrystallize the column liquid to obtain compound N-1 (yield 69.1%).

[0123] Elemental analysis: C 28 H 14N4O2; Calc: C, 76.70; H, 3.22; N, 12.78; O, 7.30; Found: C, 76.72; H, 3.23; N, 12.76; HRMS (ESI) m / z [M+H]+: Calc: 438.45; Found: 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 by starting material a-43, to obtain compound N-43 (yield 64.6%).

[0127] Elemental analysis: C 47 H 24 N4O2; Calc: C, 76.70; H, 3.22; N, 12.78; O, 7.30; Found: C, 76.72; H, 3.23; N, 12.76; HRMS (ESI) m / z [M+H]+: Calc: 438.45; Found: 439.13.

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

[0129]

[0130] Synthesis of compound N-3: In a 250 mL three-necked flask, sub-1 (38.30 mmol) and starting material a-3 (40.22 mmol) were added under nitrogen protection, and dioxane: water = 4: 1 (120 mL: 30 mL), 1,1'-bis(diphenylphosphino)ferrocene palladium dichloride (1.92 mmol), potassium carbonate (95.75 mmol), 95°C, reaction overnight, after the reaction was completed, enough water was added to quench, and the crude product solid was obtained by filtration, and the solid was quickly columned with o-dichlorobenzene, and the columned liquid was recrystallized to obtain compound N-3 (yield 66.1%).

[0131] Elemental analysis: C 35 H 20 N4O2; Calc: C, 76.70; H, 3.22; N, 12.78; O, 7.30; Found: C, 76.72; H, 3.23; N, 12.76; HRMS (ESI) m / z [M+H]+: Calc: 438.45; Found: 439.13.

[0132] Using the intermediate sub-x, the series of compounds listed in Table 1 can be obtained by changing the starting material a-n, referring to the synthetic method used in Synthetic Example 3.

[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 prepare the following device examples or device comparative examples are shown in Table 3 below.

[0144] Table 3

[0145]

[0146] Device Example 1-1

[0147] This example provides an organic electroluminescent device, such as FIG. 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, thickness 10 nm);

[0155] The material of the hole injection layer (HIL) is HAT-CN:TCTA (thickness 10 nm); wherein the mass ratio of HAT-CN to TCTA is 3:97,

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

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

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

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

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

[0161] The material of the n-type charge generation layer (CGL-n) is composed of the compound N-1 in Synthesis Example 1 and Yb, and the specific ratio and thickness are shown in Table 4;

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

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

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

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

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

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

[0168] The material of the electron injection layer (EIL) is Yb (thickness 1 nm);

[0169] The material of the cathode is Mg and Ag, mass ratio 1:9 (thickness 11 nm).

[0170] Device Example 1-2

[0171] Similar to Device Example 1-1, except that Compound N-1 in the n-type charge layer in Device Example 1-1 is changed to Compound N-43.

[0172] Device Example 1-3

[0173] Similar to Device Example 1-1, except that Compound N-1 in the n-type charge layer in Device Example 1-1 is changed to Compound N-3.

[0174] Device Example 1-4

[0175] Similar to Device Example 1-1, except that Compound N-1 in the n-type charge layer in Device Example 1-1 is changed to Compound N-4.

[0176] Device Example 1-5

[0177] Similar to Device Example 1-1, except that Compound N-1 in the n-type charge layer in Device Example 1-1 is changed to Compound N-7.

[0178] Device Example 1-6

[0179] Similar to Device Example 1-1, except that Compound N-1 in the n-type charge layer in Device Example 1-1 is changed to Compound N-34.

[0180] Device Example 1-7

[0181] Similar to Device Example 1-1, except that Compound N-1 in the n-type charge layer in Device Example 1-1 is changed to Compound N-5.

[0182] Device Example 1-8

[0183] Similar to Device Example 1-1, except that Compound N-1 in the n-type charge layer in Device Example 1-1 is changed to Compound N-9.

[0184] Device Example 1-9

[0185] Similar to Device Example 1-1, except that Compound N-1 in the n-type charge layer in Device Example 1-1 is changed to Compound N-15.

[0186] Device Example 1-10

[0187] Similar to Device Example 1-1, except that Compound N-1 in the n-type charge layer in Device Example 1-1 is changed to Compound N-20.

[0188] Device Example 1-11

[0189] Similar to Device Example 1-1, except that Compound N-1 in the n-type charge layer in Device Example 1-1 is changed to Compound N-28.

[0190] Device Example 1-12

[0191] Similar to Device Example 1-1, except that Compound N-1 in the n-type charge layer in Device Example 1-1 is changed to Compound N-33.

[0192] Device Example 1-13

[0193] Similar to Device Example 1-1, except that Compound N-1 in the n-type charge layer in Device Example 1-1 is changed to Compound N-36.

[0194] Device Example 1-14

[0195] Similar to Device Example 1-1, except that Compound N-1 in the n-type charge layer in Device Example 1-1 is changed to Compound N-39.

[0196] Device Example 1-15

[0197] Similar to Device Example 1-1, except that Compound N-1 in the n-type charge layer in Device Example 1-1 is changed to Compound N-45.

[0198] Device Example 1-16

[0199] Similar to Device Example 1-1, except that Compound N-1 in the n-type charge layer in Device Example 1-1 is changed to Compound N-64.

[0200] Device Example 1-17

[0201] Similar to Device Example 1-1, except that Compound N-1 in the n-type charge layer in Device Example 1-1 is changed to Compound N-65.

[0202] Device Example 1-18

[0203] Similar to Device Example 1-1, except that Compound N-1 in the n-type charge layer in Device Example 1-1 is changed to Compound N-66.

[0204] Device Example 1-19

[0205] Similar to Device Example 1-1, except that Compound N-1 in the n-type charge layer in Device Example 1-1 is changed to Compound N-67.

[0206] Device Example 1-20

[0207] Similar to device example 1-1, except that compound N-1 in the n-type charge layer in device example 1-1 is replaced by compound N-68.

[0208] Device example 1-21

[0209] Similar to device example 1-1, except that compound N-1 in the n-type charge layer in device example 1-1 is replaced by compound N-74.

[0210] Device example 1-22

[0211] Similar to device example 1-1, except that compound N-1 in the n-type charge layer in device example 1-1 is replaced by compound N-76.

[0212] Device example 1-23

[0213] Similar to device example 1-1, except that compound N-1 in the n-type charge layer in device example 1-1 is replaced by compound N-77.

[0214] Device comparative example 1-1

[0215] Similar to device example 1-1, except that compound N-1 in the n-type charge layer in device example 1-1 is replaced by compound REF-1.

[0216] Table 4 n-type charge generation layer composition and thickness table

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

[0218] Test example

[0219] The organic electroluminescent devices obtained for device example 1-1 to device example 1-23 and device comparative example 1-1 were tested.

[0220] Instrument: the current, voltage, brightness, and luminescence spectrum of the device were tested simultaneously using a PR 650 spectrum scanning brightness meter and a Keithley K2400 digital source meter system;

[0221] Photoelectric property test conditions: the current density was 10 mA / cm 2 at room temperature.

[0222] Lifetime test: the time (in hours) was recorded when the brightness of the device decreased to 95% of the original brightness under the condition of a current density of 10 mA / cm 2 .

[0223] wherein the lifetime T95 and current efficiency of device comparative example 1-1 in table 5 are set to 100, and the lifetime T95 and current efficiency of the remaining device examples in table 5 are the relative values thereof.

[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 material of the hole transport layer (HTL) is TCTA (thickness 20 nm);

[0238] The material of the electron blocking layer (EBL) is mCP (thickness 5 nm);

[0239] The material of the light emitting layer (EML) is D and E, mass ratio 95:5 (thickness 20 nm);

[0240] The material of the hole blocking layer (HBL) is compound N-1 in synthetic example 1 (thickness 5 nm);

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

[0242] The material of the electron injection layer (EIL) is Yb (thickness 1 nm);

[0243] The material of the cathode is Mg and Ag, mass ratio 1:9 (thickness 11 nm).

[0244] Device example 2-2

[0245] Similar to device example 2-1, except that compound N-1 in the hole blocking layer in device example 2-1 is replaced by compound N-3.

[0246] Device example 2-3

[0247] Similar to device example 2-1, except that compound N-1 in the hole blocking layer in device example 2-1 is replaced by compound N-4.

[0248] Device example 2-4

[0249] Similar to device example 2-1, except that compound N-1 in the hole blocking layer in device example 2-1 is replaced by compound N-5.

[0250] Device example 2-5

[0251] Similar to device example 2-1, except that compound N-1 in the hole blocking layer in device example 2-1 is replaced by compound N-20.

[0252] Device example 2-6

[0253] Similar to device example 2-1, except that compound N-1 in the hole blocking layer in device example 2-1 is replaced by compound N-36.

[0254] Device example 2-7

[0255] Similar to device example 2-1, except that compound N-1 in the hole blocking layer in device example 2-1 is replaced by compound N-65.

[0256] Device example 2-8

[0257] Similar to device example 2-1, except that compound N-1 in the hole blocking layer in device example 2-1 is replaced by compound N-74.

[0258] Device example 2-9

[0259] Similar to device example 2-1, except that compound N-1 in the hole blocking layer in device example 2-1 is replaced by compound N-76.

[0260] Device example 2-10

[0261] Similar to device example 2-1, except that compound N-1 in the hole blocking layer in device example 2-1 is replaced by compound N-77.

[0262] Device comparative example 2-1

[0263] Similar to device example 2-1, except that compound N-1 in the hole blocking layer in device example 2-1 is replaced by compound REF-1.

[0264] The organic electroluminescent devices obtained according to device example 2-1 to device example 2-10 and device comparative example 2-1 were tested.

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

[0266] Photoelectric property test conditions: the current density was 10 mA / cm 2 at room temperature.

[0267] Lifetime test: the time (in hours) was recorded when the brightness of the device decreased to 95% of the original brightness under the condition of a current density of 10 mA / cm 2 .

[0268] wherein the lifetime T95 and current efficiency of device comparative example 2-1 in Table 6 are set as 100, and the lifetime T95 and current efficiency of the remaining device examples in Table 6 are the relative values thereof.

[0269] Table 6: Device performance parameter table of device example 2-1 to device example 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 material of the light-emitting layer (EML) is D and E, the mass ratio is 95:5 (thickness 20 nm);

[0285] The material of the hole-blocking layer (HBL) is BCP (thickness 5 nm);

[0286] The material of the electron-transporting layer (ETL) is N-1 and LiQ in Synthetic Example 1, the mass ratio is 9:1 (thickness 25 nm);

[0287] The material of the electron-injecting layer (EIL) is Yb (thickness 1 nm);

[0288] The material of the cathode is Mg and Ag, the mass ratio is 1:9 (thickness 11 nm).

[0289] Device Example 3-2

[0290] Similar to Device Example 3-1, except that the compound N-1 in the electron-transporting layer in Device Example 3-1 is replaced by compound N-3.

[0291] Device Example 3-3

[0292] Similar to Device Example 3-1, except that the compound N-1 in the electron-transporting layer in Device Example 3-1 is replaced by compound N-34.

[0293] Device Example 3-4

[0294] Similar to Device Example 3-1, except that the compound N-1 in the electron-transporting layer in Device Example 3-1 is replaced by compound N-9.

[0295] Device Example 3-5

[0296] Similar to Device Example 3-1, except that the compound N-1 in the electron-transporting layer in Device Example 3-1 is replaced by compound N-36.

[0297] Device Example 3-6

[0298] Similar to Device Example 3-1, except that the compound N-1 in the electron-transporting layer in Device Example 3-1 is replaced by compound N-45.

[0299] Device Example 3-7

[0300] Similar to Device Example 3-1, except that the compound N-1 in the electron-transporting layer in Device Example 3-1 is replaced by compound N-65.

[0301] Device Example 3-8

[0302] Similar to device example 3-1, except that compound N-1 in the electron transport layer in device example 3-1 is replaced by compound N-74.

[0303] Device example 3-9

[0304] Similar to device example 3-1, except that compound N-1 in the electron transport layer in device example 3-1 is replaced by compound N-76.

[0305] Device example 3-10

[0306] Similar to device example 3-1, except that compound N-1 in the electron transport layer in device example 3-1 is replaced by compound N-77.

[0307] Device comparative example 3-1

[0308] Similar to device example 3-1, except that compound N-1 in the electron transport layer in device example 3-1 is replaced by compound REF-1.

[0309] The organic electroluminescent devices obtained for device example 3-1 to device example 3-10 and device comparative example 3-1 were tested.

[0310] Instrument: the current, voltage, brightness, and emission spectrum of the device were tested simultaneously using a PR 650 spectrum scanning luminance meter and a Keithley K 2400 digital source meter system.

[0311] Photoelectric property test conditions: the current density was 10 mA / cm 2 at room temperature.

[0312] Lifetime test: the current density was 10 mA / cm 2 , and the time (in hours) was recorded when the brightness of the device decreased to 95% of the original brightness.

[0313] wherein the lifetime T95 and current efficiency of device comparative example 3-1 in Table 7 are set to 100, and the lifetime T95 and current efficiency of the remaining device examples in Table 7 are the relative values thereof.

[0314] Table 7 Performance parameter table of device example 3-1 to device example 3-10 and device comparative example 3-1

[0315] Example Driving voltage (V) Current efficiency Relative lifetime T95 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 Example 3-4 3.48 113.81 115.2 Device Example 3-5 3.46 114.10 115.6 Device Example 3-6 3.58 109.61 111.3 Device Example 3-7 3.58 109.03 111.5 Device Example 3-8 3.46 115.3 115.7 Device Example 3-9 3.98 105.2 105.3 Device Example 3-10 4.11 102.3 103.1 Device Comparative Example 3-1 4.53 100 100

[0316] Obviously, the above embodiments are merely example for clearly illustrating but not limitation to the embodiments. Based on the above description, other different forms of changes or variations can be made by those skilled in the art. Here, all the embodiments need not and can not be enumerated. The obvious changes or variations derived from the above description are still within the protection scope of the present application.

Claims

1. A fused ring compound, characterized by, having the structure of formula (1) as follows: In formula (1), L is selected from a single bond, a substituted or unsubstituted C6-C60 arylene group, or a substituted or unsubstituted C3-C60 heteroarylene group; Ar is selected from the structure of formula A: In formula A, X1is selected from N or CR 1 , X2is selected from N or CR 2 , X3is selected from N or CR 3 , X3is selected from N or CR 4 , X5is selected from N or CR 5 , X6is selected from N or CR 6 ; R 1 , R 2 , R 3 , R 4 , R 5 , R 6 are each independently selected from the group consisting of hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C60alkyl, substituted or unsubstituted C3-C60cycloalkyl, substituted or unsubstituted C6-C60aryl, substituted or unsubstituted C3-C60heteroaryl; R 1 , R 2 , R 3 , R 4 , R 5 , R 6 each independently exists or the two adjacent ones can be linked to form a substituted or unsubstituted C6-C60aromatic ring, a substituted or unsubstituted C3-C60heteroaromatic ring; wherein the substituents of the substituted C6-C60 arylene group, the substituted C1-C60 alkyl group, the substituted C3-C60 cycloalkyl group, the substituted C6-C60 aryl group, the substituted C3-C60 heteroaryl group, the substituted C6-C60 aryl ring, and the substituted C3-C60 heteroaryl ring are selected from one or a combination of at least two of 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.

2. The fused ring compound according to claim 1, characterized by The structure of formula A is selected from the following structures: wherein R 1 ~R 31 each independently selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C60alkyl, substituted or unsubstituted C3-C60cycloalkyl, substituted or unsubstituted C6-C60aryl, substituted or unsubstituted C3-C60heteroaryl; wherein n1-n4are each independently selected from zero to the maximum integer value. 23 each independently selected from zero to the maximum integer value.

3. The fused ring compound according to claim 1 or 2, characterized by L is selected from a single bond, a substituted or unsubstituted C6-C30 arylene group, or a substituted or unsubstituted C3-C30 heteroarylene group; R 1 ~R 31 each independently is selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C30alkyl, substituted or unsubstituted C3-C30cycloalkyl, substituted or unsubstituted C6-C30aryl, substituted or unsubstituted C3-C30heteroaryl; wherein the substituents of the substituted C6-C30 arylene group, the substituted C3-C30 heteroarylene group, the substituted C1-C30 alkyl group, the substituted C3-C30 cycloalkyl group, the substituted C6-C30 aryl group, and the substituted C3-C30 heteroaryl group are selected from one or a combination of at least two of 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.

4. The fused ring compound according to claim 2 or 3, characterized by L is selected from a single bond, a substituted or unsubstituted A group; wherein the A group is selected from phenylene, naphthylene, phenanthrylene, biphenylene, binaphthylene, dibenzofurylene, dibenzothiophenylene, benzophenanthrolinylene, benzophenanthrolinylene, spirofluorenylene, pyridylene, phenanthrolinylene, quinolinylene, isoquinolinylene, quinoxalinylene, quinazolinylene, pyridazinylene, pyrimidinylene, pyrazinylene, triazinylene, 4,5-diazafluorenylene-9-ketylene, fluoranthrylene; R 1 ~R 31 each independently is selected from hydrogen, deuterium, halogen, cyano, a substituted or unsubstituted B group; wherein the B group is selected from the group consisting of phenyl, naphthyl, phenanthryl, anthryl, fluoranthenyl, pyrenyl, biphenyl, binaphthyl, terphenyl, phenylnaphthyl, naphthylphenyl, triphenylenyl, fluorenyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, spirobifluorenyl, 9,9-dimethylbenzofluorenyl, 9,9-diphenylbenzofluorenyl, benzosprio-bifluorenyl, cyclohexylfluorenyl, cyclopentylfluorenyl, benzofuranyl, dibenzofuranyl, naphthobenzofuranyl, dinaphthofuranyl, benzothiophenyl, dibenzothiophenyl, naphthobenzothiophenyl, carbazolyl, N-phenylcarbazolyl, benzocarbazolyl, N-phenylbenzocarbazolyl, dibenzocarbazolyl, N-biphenylcarbazolyl, benzoxazolyl, naphthoxazolyl, phenanthroxazolyl, phenanthrobenzofuranyl, benzofurobenzofuranyl, N-phenylbenzofurocarbazolyl, pyridyl, phenanthrolinyl, quinolyl, isoquinolyl, quinoxalyl, quinazolyl, pyridazinyl, pyrimidinyl, pyrazinyl, triazinyl, 4,5-diazanphthacene-9-one, fluoranthenyl; wherein each of the substituents in the substituted A group, the substituted B group is independently selected from one or a combination of at least two of deuterium, halogen, cyano, C1-C60 alkyl, C3-C60 cycloalkyl, C6-C60 aryl, C3-C60 heteroaryl, C6-C60 arylamine, C3-C60 heteroarylamine; Preferably, each of the substituents in the substituted A group, the substituted B group is independently selected from one or a combination of at least two of deuterium, halogen, cyano, methyl, ethyl, propyl, adamantyl, cyclopropanyl, cyclohexyl, cyclopentyl, phenyl, naphthyl, phenanthryl, anthryl, fluoranthenyl, pyrenyl, biphenyl, binaphthyl, terphenyl, phenylnaphthyl, naphthylphenyl, triphenylenyl, fluorenyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, spirobifluorenyl, 9,9-dimethylbenzofluorenyl, 9,9-diphenylbenzofluorenyl, benzosprio-bifluorenyl, benzofuranyl, dibenzofuranyl, naphthobenzofuranyl, dinaphthofuranyl, benzothiophenyl, dibenzothiophenyl, naphthobenzothiophenyl, carbazolyl, N-phenylcarbazolyl, benzocarbazolyl, N-phenylbenzocarbazolyl, dibenzocarbazolyl, N-biphenylcarbazolyl, benzoxazolyl, naphthoxazolyl, phenanthroxazolyl, phenanthrobenzofuranyl, benzofurobenzofuranyl, N-phenylbenzofurocarbazolyl, pyridyl, phenanthrolinyl, quinolyl, isoquinolyl, quinoxalyl, quinazolyl, pyridazinyl, pyrimidinyl, pyrazinyl, triazinyl, 4,5-diazanphthacene-9-one, fluoranthenyl.

5. The fused ring compound according to any one of claims 1 to 4, characterized by, The fused ring compound is selected from any of the following structures:

6. An n-type charge generation material characterized by, The n-type charge generation material includes any one or a combination of at least two of the fused ring compounds of any one of claims 1-5.

7. An electron transport material, characterized in that, The electron transport material includes any one or a combination of at least two of the fused ring compounds of any one of claims 1-5.

8. A hole-blocking material, characterized by, The hole blocking material includes any one or a combination of at least two of the fused ring compounds of any one of claims 1-5.

9. An organic electroluminescent device, characterized by The organic electroluminescent device comprises a cathode, an anode, and an organic layer between the cathode and the anode, the organic layer comprising any one or a combination of at least two of the fused ring compounds according to any one of claims 1-5; Preferably, the organic layer comprises an n-type charge generation layer, the n-type charge generation layer comprising the n-type charge generation material according to claim 6; and / or, the organic layer comprises an electron transport layer, the electron transport layer comprising the electron transport material according to claim 7; and / or, the organic layer comprises a hole blocking layer, the hole blocking layer comprising the hole blocking material according to claim 8.

10. Use of the organic electroluminescent device according to claim 9 in an optical fiber device, a lighting device, an electrophotographic photoreceptor device, a photoelectric converter, an organic solar cell, a switching element device, an organic light emitting field effect transistor, an image sensor, or a dye laser.

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