Organic electroluminescent element and electronic equipment comprising same

Abstract

The invention relates to an organic electroluminescent element and electronic equipment comprising the same. The organic electroluminescent element according to the present invention comprises an anode, a cathode, and a light-emitting layer between the anode and the cathode, a first organic layer is included between the anode and the light-emitting layer, and the first organic layer comprises a compound represented by structural formula (1). The organic electroluminescent element according to the present invention has a reduced driving voltage and a long lifespan.

Description

TECHNICAL FIELD

[0001] The present application relates to the technical field of organic electroluminescence, and more particularly, to an organic electroluminescent element and an electronic device. BACKGROUND

[0002] An organic electroluminescent element is composed of an anode, a cathode, and one or more organic thin film layers interposed between the anode and the cathode. If a voltage is applied between the two electrodes, electrons are injected from the cathode side to the light emitting region, and holes are injected from the anode side to the light emitting region. The injected electrons and holes recombine in the light emitting region to generate an excited state, and light is emitted when the excited state returns to the ground state. In recent years, as smartphones, televisions, lighting, and the like using organic electroluminescent elements have become more widespread, there is a demand for materials that can satisfy the element lifetime while reducing the driving voltage. SUMMARY

[0003] An object of the present application is to provide an organic electroluminescent element having improved driving voltage and lifetime.

[0004] TECHNICAL SOLUTION

[0005] The present application provides an organic electroluminescent element comprising an anode, a cathode, and a light emitting layer interposed between the anode and the cathode, characterized in that a first organic layer is contained between the anode and the light emitting layer, the first organic layer comprising a compound represented by structural formula (1),

[0006]

[0007] L 1 , L 2 each independently selected from a single bond, a substituted or unsubstituted C6-C30 arylene group, a substituted or unsubstituted C3-C30 N-free heteroarylene group,

[0008] Ar 1 , Ar 2 each independently selected from hydrogen, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C3-C30 N-free heteroaryl group,

[0009] the substituents in the substituted or unsubstituted are free of N;

[0010] Preferably, the compound represented by structural formula (1) can not contain or contain at least one substituent selected from deuterium, a fluoro group, a cyano group; more preferably, the compound represented by structural formula (1) can not contain or contain at least one substituent selected from deuterium, a fluoro group; more preferably, the compound represented by structural formula (1) can not contain or contain at least one deuterium;

[0011] Preferably, the substituted or unsubstituted C6-C30 arylene group does not contain a phenanthrylene group, and the substituted or unsubstituted C6-C30 aryl group does not contain a phenanthryl group.

[0012] Preferably, the substituent in the substituted group does not contain a phenanthryl group.

[0013] One embodiment of the present application is that the formula (1) is selected from formula (2), (3) or (4),

[0014]

[0015] L 1 , L 2 , Ar 1 , Ar 2 The definition is the same as formula (1);

[0016] Preferably, the above-mentioned compound can not contain or contain at least one substituent selected from deuterium, fluorine group, cyano group; more preferably, the above-mentioned compound can not contain or contain at least one substituent selected from deuterium, fluorine group; more preferably, the above-mentioned compound can not contain or contain at least one deuterium.

[0017] One embodiment of the present application is that the formula (1) is selected from formula (2-1), (2-2), (2-3), (3-1), (3-2), (3-3), (4-1), (4-2), (4-3),

[0018]

[0019] L 1 , L 2 , Ar 1 , Ar 2 The definition is the same as formula (1);

[0020] Preferably, the above-mentioned compound can not contain or contain at least one substituent selected from deuterium, fluorine group, cyano group; more preferably, the above-mentioned compound can not contain or contain at least one substituent selected from deuterium, fluorine group; more preferably, the above-mentioned compound can not contain or contain at least one deuterium.

[0021] One embodiment of the present application is that the formula (1) is selected from formula (2-2), (2-3), (3-2), (3-3), (4-2), (4-3),

[0022]

[0023] L 1 , L 2 , Ar 1 , Ar 2 The definition is the same as formula (1);

[0024] Preferably, the above-mentioned compound can comprise or not at least one substituent selected from deuterium, fluoro, cyano; more preferably, the above-mentioned compound can comprise or not at least one substituent selected from deuterium, fluoro; more preferably, the above-mentioned compound can comprise or not at least one deuterium.

[0025] One embodiment of the present application is a compound of formula (1) selected from formulae (2-2), (2-3),

[0026]

[0027] L 1 , L 2 , Ar 1 , Ar 2 as defined for formula (1);

[0028] Preferably, the above-mentioned compound can comprise or not at least one substituent selected from deuterium, fluoro, cyano; more preferably, the above-mentioned compound can comprise or not at least one substituent selected from deuterium, fluoro; more preferably, the above-mentioned compound can comprise or not at least one deuterium.

[0029] One embodiment of the present application is a compound of formula (1) selected from formula (2-3),

[0030]

[0031] L 1 , L 2 , Ar 1 , Ar 2 as defined for formula (1);

[0032] Preferably, the above-mentioned compound can comprise or not at least one substituent selected from deuterium, fluoro, cyano; more preferably, the above-mentioned compound can comprise or not at least one substituent selected from deuterium, fluoro; more preferably, the above-mentioned compound can comprise or not at least one deuterium.

[0033] In one embodiment of the present application, L in formulae (1), (2), (3), (2-1), (2-2), (2-3), (3-1), (3-2), (3-3), (4-1), (4-2), (4-3) 1 , L 2each independently selected from a single bond, substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted anthrylene, substituted or unsubstituted phenanthrylene, substituted or unsubstituted biphenylene, substituted or unsubstituted terphenylene, substituted or unsubstituted phenylnaphthylene, substituted or unsubstituted dibenzofuranylene, substituted or unsubstituted dibenzothiophenylene, substituted or unsubstituted 9,9'-dimethylfluorenylene, substituted or unsubstituted 9,9'-diphenylfluorenylene, substituted or unsubstituted spirobifluorenylene.

[0034] In one embodiment of the present application, Ar in formulae (1), (2), (3), (2-1), (2-2), (2-3), (3-1), (3-2), (3-3), (4-1), (4-2), (4-3) 1 , Ar 2 each independently selected from hydrogen, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthryl, substituted or unsubstituted phenanthryl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted phenylnaphthyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted 9,9'-dimethylfluorenyl, substituted or unsubstituted 9,9'-diphenylfluorenyl, substituted or unsubstituted spirobifluorenyl; preferably Ar 1 , Ar 2 is not substituted or unsubstituted phenanthryl.

[0035] In one embodiment of the present application, L in formulae (1), (2), (3), (2-1), (2-2), (2-3), (3-1), (3-2), (3-3), (4-1), (4-2), (4-3) 1 , L 2 each independently selected from a single bond, substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted anthrylene, substituted or unsubstituted phenanthrylene, substituted or unsubstituted biphenylene, substituted or unsubstituted terphenylene, substituted or unsubstituted phenylnaphthylene, substituted or unsubstituted dibenzofuranylene, substituted or unsubstituted dibenzothiophenylene, substituted or unsubstituted 9,9'-dimethylfluorenylene, substituted or unsubstituted 9,9'-diphenylfluorenylene, substituted or unsubstituted spirobifluorenylene.

[0036]

[0037] dotted line represents a substitution position.

[0038] In one embodiment of the present application, Ar in formulae (1), (2), (3), (2-1), (2-2), (2-3), (3-1), (3-2), (3-3), (4-1), (4-2), (4-3) 1 , Ar 2 each independently selected from hydrogen, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthryl, substituted or unsubstituted phenanthryl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted phenylnaphthyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted 9,9'-dimethylfluorenyl, substituted or unsubstituted 9,9'-diphenylfluorenyl, substituted or unsubstituted spirobifluorenyl; preferably Ar

[0039]

[0040] dotted line represents a substitution position;

[0041] Preferably, the above groups are unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, fluorine, cyano; more preferably, the above groups are unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, fluorine; more preferably, the above groups are unsubstituted or substituted with one or more deuterium; more preferably, the above groups are unsubstituted or substituted with one or more deuterium; most preferably, the above groups are unsubstituted;

[0042] In one embodiment of the present application, -L in formula (1), (2), (3), (2-1), (2-2), (2-3), (3-1), (3-2), (3-3), (4-1), (4-2), (4-3) is independently selected from the group consisting of hydrogen, halogen, cyano, C1-C10 alkyl, C3-C10 cycloalkyl, C1-C10 alkoxy, C2-C10 alkenyl, C2-C10 alkynyl, C6-C60 aryl, C3-C60 heteroaryl, C3-C60 heterocyclyl, wherein the heteroatoms in the heterocyclyl, heteroaryl are selected from at least one of O, S; 1 -Ar 1 , -L 2 -Ar 2 are each independently selected from the group consisting of hydrogen, halogen, cyano, C1-C10 alkyl, C3-C10 cycloalkyl, C1-C10 alkoxy, C2-C10 alkenyl, C2-C10 alkynyl, C6-C60 aryl, C3-C60 heteroaryl, C3-C60 heterocyclyl, wherein the heteroatoms in the heterocyclyl, heteroaryl are selected from at least one of O, S;

[0043]

[0044]

[0045]

[0046] dashed line represents a substitution position;

[0047] Preferably, the above groups are unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, fluorine, cyano; more preferably, the above groups are unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, fluorine; more preferably, the above groups are unsubstituted or substituted with one or more deuterium; more preferably, the above groups are unsubstituted or substituted with one or more deuterium; most preferably, the above groups are unsubstituted;

[0048] Preferably, the above -L 1 -Ar 1 , -L 2 -Ar 2 are each independently selected from the group consisting of hydrogen, halogen, cyano, C1-C10 alkyl, C3-C10 cycloalkyl, C1-C10 alkoxy, C2-C10 alkenyl, C2-C10 alkynyl, C6-C60 aryl, C3-C60 heteroaryl, C3-C60 heterocyclyl, wherein the heteroatoms in the heterocyclyl, heteroaryl are selected from at least one of O, S;

[0049] In the present application, the substituents in the case of substitution in “substituted or unsubstituted” are independently selected from the group consisting of deuterium, halogen, cyano, C1-C10 alkyl, C3-C10 cycloalkyl, C1-C10 alkoxy, C2-C10 alkenyl, C2-C10 alkynyl, C6-C60 aryl, C3-C60 heteroaryl, C3-C60 heterocyclyl, wherein the heteroatoms in the heterocyclyl, heteroaryl are selected from at least one of O, S;

[0050] Preferably, in the present application, the substituents in the case of substitution in “substituted or unsubstituted” are independently selected from the group consisting of deuterium, halogen, cyano, methyl, ethyl, propyl, n-butyl, t-butyl, cyclopentyl, cyclohexyl, adamantyl, fluorenyl, spiro fluorenyl, phenyl, biphenyl, terphenyl, naphthyl, anthryl, phenanthryl, pyrenyl, fluoranthenyl, triphenylenyl, one or more of deuterium, halogen, cyano, methyl, ethyl, tert-butyl, cyclopentyl, adamantyl, fluorenyl, spiro fluorenyl, phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, dibenzofuranyl, dibenzothiophenyl, furanyl, benzothiophenyl, benzofuranyl, methoxy, tert-butoxy, thienyl, phenylnaphthyl; more preferably one or more of deuterium, halogen, cyano, methyl, ethyl, tert-butyl, cyclopentyl, adamantyl, fluorenyl, spiro fluorenyl, phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, dibenzofuranyl, dibenzothiophenyl, benzothiophenyl, benzofuranyl, methoxy; even more preferably one or more of deuterium, halogen, cyano, methyl, ethyl, tert-butyl, fluorenyl, spiro fluorenyl, phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, dibenzofuranyl, dibenzothiophenyl, phenylnaphthyl; in particular one or more of deuterium, halogen, cyano, methyl, ethyl, tert-butyl, phenyl, naphthyl, biphenyl, phenylnaphthyl; in particular one or more of deuterium, fluoro, cyano, phenyl, naphthyl, biphenyl, phenylnaphthyl; in particular one or more of deuterium, fluoro, phenyl, naphthyl, biphenyl; in particular one or more of deuterium, phenyl, naphthyl, biphenyl; in particular one or more of deuterium, phenyl, biphenyl; in particular one or more of deuterium, phenyl; most preferably deuterium;

[0051] Examples of the combination of the plurality are deuterated phenyl, deuterated methyl, methyl-substituted phenyl, deuterated methyl-substituted phenyl, and the like. In one embodiment of the present application, the formula (1) is selected from the structures represented by the following compounds,

[0052]

[0053]

[0054]

[0055]

[0056]

[0057]

[0058]

[0059]

[0060]

[0061]

[0062]

[0063] In one embodiment of the present application, formula (1) is represented by X1is selected from any one of the following groups X1-X9, n

[0064]

[0065] When formula X n is selected from the group X1, -L 1 -Ar 1 , -L 2 -Ar 2 is selected from the following table, the compound is numbered X1-1 to X1-3321,

[0066]

[0067]

[0068]

[0069]

[0070]

[0071]

[0072]

[0073]

[0074]

[0075]

[0076]

[0077]

[0078]

[0079]

[0080]

[0081] ​

[0082]

[0083]

[0084]

[0085]

[0086]

[0087]

[0088]

[0089]

[0090]

[0091]

[0092]

[0093]

[0094]

[0095]

[0096]

[0097]

[0098]

[0099]

[0100]

[0101]

[0102]

[0103]

[0104]

[0105]

[0106]

[0107]

[0108]

[0109]

[0110] X2 replaces X1, -L 1 -Ar 1 , -L 2 -Ar 2 is selected from the above table, the compounds are numbered X2-1 to X2-3321,

[0111] X3 replaces X1, -L 1 -Ar 1 , -L 2 -Ar 2 is selected from the above table, the compounds are numbered X3-1 to X3-3321,

[0112] X4 replaces X1, -L 1 -Ar 1 , -L 2 -Ar 2 is selected from the above table, the compounds are numbered X4-1 to X4-3321,

[0113] X5 replaces X1, -L 1 -Ar 1 , -L 2 -Ar 2 is selected from the above table, the compounds are numbered X5-1 to X5-3321,

[0114] X6 replaces X1, -L 1 -Ar 1 , -L 2 -Ar 2 is selected from the above table, the compounds are numbered X6-1 to X6-3321,

[0115] X7 replaces X1, -L 1 -Ar 1 , -L 2 -Ar 2 is selected from the above table, the compounds are numbered X7-1 to X7-3321,

[0116] X8 replaces X1, -L 1 -Ar 1 , -L 2 -Ar 2 is selected from the above table, the compounds are numbered X8-1 to X8-3321,

[0117] X9 replaces X1, -L 1 -Ar 1 , -L 2-Ar 2 Selected from the above table, the compounds are numbered X9-1 to X9-3321.

[0118] In another embodiment of the present invention, the first organic layer is a luminescence-assisting layer, an electron blocking layer, a hole transport layer, a charge generation layer, or a hole injection layer; preferably, the first organic layer is a luminescence-assisting layer, an electron blocking layer, a p-type charge generation layer, or a hole transport layer; more preferably, the first organic layer is a luminescence-assisting layer, an electron blocking layer, or a hole transport layer; more preferably, the first organic layer is a luminescence-assisting layer, an electron blocking layer, or a second hole transport layer; most preferably, the first organic layer is a luminescence-assisting layer or an electron blocking layer. In another embodiment of the present invention, the first organic layer is an electron blocking layer, adjacent to the light-emitting layer.

[0119] In another embodiment of the present invention, the organic electroluminescent element is a single-layer element or a stacked-layer element.

[0120] In another embodiment of the present invention, the organic electroluminescent element is a single-layer element, and the first organic layer between the anode and the light-emitting layer is an electron blocking layer, which is adjacent to the light-emitting layer.

[0121] In another embodiment of the present invention, the organic electroluminescent element is a stacked element, which includes two or more light-emitting units, each light-emitting unit includes a light-emitting layer, each light-emitting unit contains a first organic layer, the first organic layer is located between the anode and each light-emitting unit, the multiple first organic layer materials are the same or different, and at least one of them is selected from the compound represented by the above formula (1); the first organic layer is preferably a light-emitting auxiliary layer, an electron blocking layer, a hole transport layer, a charge generation layer, or a hole injection layer, more preferably a light-emitting auxiliary layer, an electron blocking layer, a P-type charge generation layer, or a hole transport layer, more preferably a light-emitting auxiliary layer, an electron blocking layer, or a hole transport layer, especially preferably a light-emitting auxiliary layer, an electron blocking layer, or a second hole transport layer, and particularly preferably a light-emitting auxiliary layer or an electron blocking layer.

[0122] In another embodiment of the present invention, the organic electroluminescent element is a stacked element, which includes two or more light-emitting units, each of which includes a light-emitting layer, and each light-emitting unit contains a first organic layer, which is located between the anode and each light-emitting unit, and the first organic layer is an electron blocking layer, which is adjacent to the light-emitting layer in each light-emitting unit. The materials of the multiple electron blocking layers are the same or different, and at least one of the electron blocking layers is selected from the compound represented by the above formula (1).

[0123] A second object of the present invention is to provide an electronic device comprising the organic electroluminescent element of the present invention.

[0124] Overall, compared with the prior art, the above technical solutions conceived by the present application can achieve the following beneficial effects:

[0125] 1. The organic electroluminescent element of the present application adopts a specific material (structure: benzo carbazole-phenylene-naphthalene-substituted amine), especially when the electron blocking layer adopts the material, by introducing benzo carbazole-phenylene-naphthalene with a rigid structure, the molecular packing can be effectively regulated, and excessive disordered arrangement can be avoided, so that the material has better film-forming property and thermal stability, which is beneficial to improve the service life of the organic electroluminescent device, and the prepared element shows excellent performance. BRIEF DESCRIPTION OF DRAWINGS

[0126] Figure 1 is a structural schematic diagram of the organic electroluminescent element described in application example 1; wherein: Figure 1 Each mark in the above formula (I) represents: 1, substrate, 2, anode, 3, hole injection layer, 4, hole transport layer, 5, electron blocking layer, 6, light-emitting layer, 7, hole blocking layer, 8, electron transport layer, 9, cathode.

[0127] Figure 2 is a mass spectrum of the compound X3-10 prepared in the compound preparation example.

[0128] Figure 3 is a nuclear magnetic spectrum of the compound X3-10 prepared in the compound preparation example.

[0129] Figure 4 is a mass spectrum of the compound X3-17 prepared in the compound preparation example.

[0130] Figure 5 is a nuclear magnetic spectrum of the compound X3-17 prepared in the compound preparation example.

[0131] Figure 6 is a mass spectrum of the compound X3-264 prepared in the compound preparation example. DETAILED DESCRIPTION

[0132] Example embodiments now will be described in detail with reference to the drawings, wherein like reference numerals represent like elements throughout the various figures. In this regard, the present example embodiments can have different forms and should not be construed as limited to the description set forth herein. Rather, the example embodiments are described throughout so that this disclosure will convey the scope of the present example embodiments to those skilled in the art. Accordingly, the example embodiments are described below, by reference to the drawings, to illustrate the present example embodiments. As used herein, the term "and / or" includes any and all combinations of one or more of the associated listed items. Expressions such as "at least one of," when preceding the

[0133] It will be understood that when an element is referred to as being "on" another element, it can be directly on the other element or intervening elements can be present therebetween. In contrast, when an element is referred to as being "directly on" another element, there are no intervening elements present.

[0134] It will be understood that the terms "comprises" and "comprising," when used in this specification, set out that there are presence of stated features, regions, integers, steps, operations, elements, and / or components, but do not preclude the presence or addition of one or more other features, regions, integers, steps, operations, elements, components, and / or groups thereof.

[0135] Unless otherwise defined, all terms (including technical and scientific terms) used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this general inventive concept belongs. It will be further understood that terms, such as those defined in commonly used dictionaries, should be interpreted as having a meaning that is consistent with their meaning in the context of the relevant art and the present disclosure and will not be interpreted in an idealized or overly formal sense unless expressly so defined herein.

[0136] The present application is further described in detail by way of specific examples. The examples are provided for illustration purposes only and are not intended to limit the scope of the present application. Furthermore, it is understood that various modifications and changes can be made to the present application by those skilled in the art in light of the teachings herein without departing from the scope of the present application.

[0137] The experimental methods used in the following examples are routine methods unless otherwise specified; the reagents, materials, etc. used in the following examples are commercially available unless otherwise specified.

[0138] Terminology

[0139] As used herein, the term "halogen" can include fluorine, chlorine, bromine, or iodine.

[0140] As used herein, the term "C1-C10 alkyl" refers to a monovalent substituent derived from a straight-chain or branched-chain saturated hydrocarbon having from 1 to 10 carbon atoms. Examples thereof include, but are not limited to, methyl, ethyl, propyl, isobutyl, sec-butyl, t-butyl, pentyl, isopentyl, and hexyl.

[0141] As used herein, the term "C3-C10 cycloalkyl" refers to a monovalent substituent derived from a monocyclic or polycyclic non-aromatic hydrocarbon having from 3 to 10 carbon atoms. Examples of such cycloalkyl groups include, but are not limited to, cyclopropane, cyclobutane, cyclopentane, cyclohexane, norbornyl, adamantane, and the like.

[0142] As used herein, the term "C2-C10 alkenyl" refers to a monovalent substituent derived from a straight-chain or branched-chain unsaturated hydrocarbon having one or more carbon-carbon double bonds and having from 2 to 10 carbon atoms. Examples thereof include, but are not limited to, ethenyl, propenyl, isopropenyl, 2-butenyl, and the like.

[0143] As used herein, the term "C2-C10 alkynyl" refers to a monovalent substituent derived from a straight-chain or branched-chain unsaturated hydrocarbon having one or more carbon-carbon triple bonds and having from 2 to 10 carbon atoms. Examples thereof include, but are not limited to, ethynyl, 2-propynyl, and the like.

[0144] As used herein, the term "C3-C60 heterocyclyl" refers to a monovalent substituent derived from a monocyclic or polycyclic ring having from 3 to 60 carbon atoms, and at least one heteroatom in the ring selected from O, S.

[0145] As used herein, the term "alkoxy" refers to a straight-chain, branched, or cyclic chain. The number of carbon atoms of the alkoxy group is not particularly limited herein, but the alkoxy group preferably has from 1 to 10 carbon atoms. Specific examples thereof include, but are not limited to, methoxy, ethoxy, n-propoxy, isopropoxy, isopropoxy, n-butoxy, isobutoxy, t-butoxy, sec-butoxy, n-pentoxy, neopentoxy, isopentoxy, n-hexoxy, benzyloxy.

[0146] As used herein, the term "C6-C60 aryl" refers to a monovalent substituent derived from an aromatic hydrocarbon having a single ring or a combination of two or more rings and having from 6 to 60 carbon atoms. Further, such aryl group can have a form in which two or more rings are simply flanked to each other or fused to each other. Examples of such aryl group include, but are not limited to, phenyl, biphenyl, naphthyl, phenanthryl, anthryl, pyrenyl, triphenylenyl, fluoranthenyl, dimethyl 9,9-dimethylfluorene, 9,9-diphenylfluorene, spirobifluorenyl, and the like.

[0147] As used herein, the term "arylene" refers to a divalent aryl group derived by removing one hydrogen atom from an "aryl group", for example, phenyl removing one hydrogen atom to form phenylene, naphthyl removing one hydrogen atom to form naphthylene.

[0148] As used herein, the term "C3-C60heteroaryl group" refers to a monovalent substituent derived from a mono- or polyheterocyclic aromatic hydrocarbon having 3 to 60 carbon atoms. In the linkage, at least one of the carbons in the ring, preferably 1 to 3 carbons, is substituted with a heteroatom such as O, S. Further, such a heteroaryl group can have a form in which two or more rings are simply flanked to each other or fused to each other or fused to an aryl group. Examples of such a heteroaryl group include, but are not limited to, furanyl, thienyl, benzofuranyl, benzothienyl, dibenzofuranyl, dibenzothienyl, and the like, and the present application is not limited thereto.

[0149] As used herein, the term "heteroarylene" refers to a divalent heteroaryl group derived by removing one hydrogen atom from a "heteroaryl group".

[0150] As used herein, "carbon number of M-N of K group" or "C(M-N) of K group" in the expression means the carbon number of K group when it is unsubstituted, and does not include the carbon number of the substituent when it is substituted, for example, C6-C60 of aryl group means that the carbon number of aryl group is any one of integers from 6 to 60 when it is unsubstituted, i.e., the carbon number can be 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20,..., 60 when it is unsubstituted.

[0151] As used herein, the term "substituted" means that a hydrogen atom in a compound is substituted with another substituent. The position where substitution occurs can be a position where a hydrogen atom is substituted. That is, the position is not limited to a specific position, as long as the hydrogen at the position can be substituted with a substituent. "Unsubstituted" means that a hydrogen atom is retained, and in this case, the hydrogen atom includes protium, deuterium, tritium, and the case of substitution can include the case of substitution with deuterium, tritium.

[0152] When two or more substituents are present, the two or more substituents can be the same or different.

[0153] As used herein, the term "terphenyl" includes

[0154] As used herein, the term "phenylnaphthyl" includes, but is not limited to

[0155]

[0156] As used herein, the term "phenylnaphthyl" includes, but is not limited to

[0157]

[0158] As used in the present application, a hydrogen atom includes protium, deuterium and tritium. The compound of the present application can contain deuterium atoms of natural origin, or deuterium atoms can be introduced by deuterium substitution of a part or all of the starting compound. If deuterium atoms are introduced from the starting material, the deuterium substitution rate can be 100%, or less than 100%, or less than 95%, or less than 90%, or less than 80%, or more than 1%, or more than 5%, or more than 10%. If the deuterium substitution rate is not 100%, it means a mixture of deuterium-substituted compound and non-deuterium-substituted compound, or a mixture of completely deuterium-substituted compound and incompletely deuterium-substituted compound, or a mixture of completely deuterium-substituted compound and non-deuterium-substituted compound and incompletely deuterium-substituted compound.

[0159] As used in the present application, the terms 1st, 2nd, A, B, etc. are used. The above terms are used only to distinguish the constituent elements, and do not limit the nature or order of the terms corresponding to the constituent elements.

[0160] Organic electroluminescent element

[0161] The structure used in the organic electroluminescent element of the present application is a publicly known structure, and includes an anode, a cathode, and an organic layer between the anode and the cathode, the organic layer including a light-emitting layer.

[0162] The organic layer further includes one or more of a hole injection layer, a hole transport layer, an electron blocking layer, a hole blocking layer, an electron transport layer, an electron injection layer, but is not limited thereto.

[0163] The light-emitting element of the present application can be fluorescent light emission or phosphorescent light emission or a combination thereof, and can be a single light-emitting element or a series of multiple light-emitting units.

[0164] As a simple light-emitting element, the following can be cited, but is not limited thereto,

[0165] (1) a hole transport layer / a fluorescent light-emitting layer / an electron transport layer;

[0166] (2) a hole transport layer / a phosphorescent light-emitting layer / an electron transport layer;

[0167] (3) a hole transport layer / a first fluorescent light-emitting layer / a second fluorescent light-emitting layer / an electron transport layer;

[0168] (4) a hole transport layer / a first phosphorescent light-emitting layer / a second phosphorescent light-emitting layer / an electron transport layer;

[0169] (5) a hole transport layer / a fluorescent light-emitting layer / a spacer layer / a phosphorescent light-emitting layer / an electron transport layer;

[0170] (6) a hole transport layer / an electron blocking layer / a fluorescent light-emitting layer / an electron transport layer;

[0171] (7) hole transport layer / electron blocking layer / phosphorescent emission layer / hole blocking layer / electron transport layer;

[0172] (8) hole transport layer / electron blocking layer / phosphorescent emission layer / electron transport layer;

[0173] (9) hole transport layer / electron blocking layer / phosphorescent emission layer / hole blocking layer / electron transport layer;

[0174] (10) hole injection layer / hole transport layer / phosphorescent emission layer / electron transport layer / electron injection layer;

[0175] (11) hole injection layer / hole transport layer / phosphorescent emission layer / electron transport layer / electron injection layer;

[0176] (12) hole injection layer / hole transport layer / electron blocking layer / phosphorescent emission layer / electron transport layer / electron injection layer;

[0177] (13) hole injection layer / hole transport layer / electron blocking layer / phosphorescent emission layer / electron transport layer / electron injection layer;

[0178] Each of the above phosphorescent / emission layers can be a different color of emission.

[0179] As a tandem type organic electroluminescent device, it can be anode / first emission unit / intermediate layer / second emission unit / cathode, and the intermediate layer can also be generally referred to as a charge generation layer, an electron extraction layer, a connecting layer, etc., for example, when a phosphorescent emission layer and a fluorescent emission layer are stacked, in order to prevent excitons generated in the phosphorescent emission layer from diffusing to the fluorescent emission layer, or to adjust the balance of carriers, an intermediate layer is placed between the fluorescent emission layer and the phosphorescent emission layer.

[0180] When the organic light emitting device includes a plurality of organic material layers, the organic material layers can be formed of the same material or different materials.

[0181] The organic electroluminescent device of the present specification can be manufactured by materials and methods known in the art, except that one or more organic material layers are formed by using a compound comprising the compound described in the present invention.

[0182] As the anode material, a material having a relatively large work function can be used, and a transparent conductive oxide, a metal, a conductive polymer, or the like can be used. Specific examples of the anode material include: a metal such as vanadium, chromium, copper, zinc, and gold, or an alloy thereof; a metal oxide such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); a combination of a metal and an oxide such as ZnO:Al or SnO2:Sb; a conductive polymer such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), polypyrrole, and polyaniline, but is not limited thereto.

[0183] As the cathode material, a material having a low work function is generally used to facilitate electron injection into the organic layer, and a metal, a metal oxide, a conductive polymer, or the like can be used. Specific examples of the cathode material include: a metal such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or an alloy thereof; a multilayered structure material such as LiF / Al or LiO2 / Al, but is not limited thereto.

[0184] The hole injection layer is a layer that injects holes from the electrode, and has a capability of transporting holes. In order to reduce the energy level difference between the electrodes, the hole injection layer is mainly prepared based on an aromatic amine compound, and can also be prepared using a material having a lowest unoccupied molecular orbital energy level selected from a copper phthalocyanine complex, HATCN (2,3,6,7,10,11-hexacyano-1,4,5,8,9,12-hexaazatriphenylene) having a phenylene structure, or the like. When used as a light-emitting host and a dopant, F4-TCNQ (2,2,3,5,6-tetrafluoro-7,7',8,8'-tetracyanoquinodimethane) can be doped in the aromatic amine compound as a lowest unoccupied molecular orbital energy level inducing body.

[0185] The hole transport layer is a layer that receives holes from the hole injection layer and transports the holes to the light-emitting layer, and the hole transport material can be appropriately a material having a high hole mobility that receives holes from the anode or the hole injection layer and transports the holes to the light-emitting layer, and an arylamine derivative, a triphenyl diamine derivative, or the like can be used, and a low molecular or a high molecular material can also be used.

[0186] The electron blocking layer can adjust the energy level difference between the hole transport region and the light-emitting layer, facilitate the entry of holes into the light-emitting layer, and at the same time, reduce the probability of the entry of electrons from the light-emitting layer into the hole transport region, and an aromatic amine derivative is commonly used.

[0187] The light emitting material can be a material that receives holes and electrons from the hole transport layer and the electron transport layer, respectively, and combines the holes and the electrons to emit light in the visible light region. The light emitting layer material includes a host material and a dopant material. A red, green, or blue light emitting material can be used, and two or more kinds of light emitting materials can be mixed as needed. As the light emitting material, a fluorescent material can be used, and a phosphorescent material can be used. As the light emitting material, a single component material can be used, and a multi-component material can be used.

[0188] The electron transport layer is a layer that receives electrons from the electron injection layer and transports the electrons to the light emitting layer, and the electron transport material can be a material that receives electrons from the cathode and transports the electrons to the light emitting layer with high electron mobility. Metal complexes of triazine derivatives, oxadiazole derivatives, benzoquinone and derivatives thereof, naphthoquinone and derivatives thereof, anthraquinone and derivatives thereof, fluorenone derivatives, diphenyldicyanoethylene and derivatives thereof, 8-hydroxyquinoline and derivatives thereof, and the like can be used, and a high molecular material and a small molecular material can also be used.

[0189] The electron injection layer is a layer that injects electrons from the electrode.

[0190] The organic light emitting device of the present specification can be a top emission type device, a bottom emission type device, or a dual emission type device, depending on the materials used.

[0191] The charge generation layer refers to an intermediate layer between the anode and the cathode in a tandem structure type device, and is a layer that generates holes and electrons by charge separation. The charge generation layer is usually formed of a P-type layer on the cathode side and an N-type layer on the anode side, and can effectively separate charges and effectively transport carriers.

[0192] In one embodiment of the present application, the method of forming each layer is not particularly limited. The formation method based on a vacuum evaporation method, a spin coating method, or the like, which has been known in the past, can be used. Each layer such as the light emitting layer can be formed by a known method such as a vacuum evaporation method, a molecular beam evaporation method (MBE method), or a coating method based on an immersion method, a spin coating method, a casting method, a bar coating method, a roll coating method, or the like, of a solution dissolved in a solvent.

[0193] In one embodiment of the present application, the film thickness of each layer is not particularly limited, and generally several nanometers to several hundred nanometers can be used.

[0194] A person skilled in the art can synthesize the compounds of the present application by referring to the synthesis of the following compounds and known synthesis methods. There are various synthesis methods for the compounds of the present application, and the following methods are merely illustrative.

[0195] LC-MS brand: Waters, model: SQ Detector 2

[0196] NMR brand: Bruker, model: AVANCE NEO 400

[0197] The compounds of the present application can be synthesized by those skilled in the art with reference to the synthesis of the following compounds and known synthetic methods. An exemplary synthesis of the present application is as follows:

[0198]

[0199] R is each independently selected from halogen (fluorine, chlorine, bromine, iodine), and a plurality of R is the same or different, and the remaining groups are as defined in structural formula (1).

[0200] Synthesis Example 1: Synthesis of compound X3-241

[0201] (1) Synthesis of intermediate X3-241-1

[0202]

[0203] Under N2atmosphere, 20 g (92 mmol) of 7H-benzo[C]carbazole, 16.9 g (97 mmol) of o-bromofluorobenzene, 25.4 g (184 mmol) of potassium carbonate, and 150 ml of DMF were added to a four-necked reaction flask, and then heated at 150°C with stirring for 12 hours. After the reaction was completed, the mixture was cooled to room temperature. The solution was extracted with ethyl acetate and water, and the organic phase was dried over anhydrous sodium sulfate and then the solvent was removed. Purification was performed by silica gel chromatography (developing solvent: n-hexane: EA = volume ratio 100:1) to obtain a light yellow intermediate X3-241-1 (29 g, 85%).

[0204] LC-MS (APCI): 372.21 (M+H + ). Calcd for C 22 H 11 BrN

[0205] (2) Synthesis of intermediate X3-241-2

[0206]

[0207] Under N2atmosphere, 10 g (26.8 mmol) of intermediate X3-241-1, 5.8 g (18.2 mmol) of 4-chloro-1-naphthaleneboronic acid, 5.0 g (36.4 mmol) of potassium carbonate, 70 ml of toluene, 30 ml of ethanol, 30 ml of water, 0.63 g (0.55 mmol) of tetrakis(triphenylphosphine)palladium were added to a four-necked flask, and the reaction was carried out by heating to 85°C. After the reaction was completed, the reaction solution was cooled to room temperature. The reaction solution was extracted with dichloromethane, and the organic phase was dried over anhydrous sodium sulfate and then the solvent was removed. Purification was performed by silica gel chromatography (developing solvent: n-hexane: DCM = 20: 1 by volume), to obtain white intermediate X3-241-2 (10.8 g, 88%).

[0208] LC-MS (APCI): 454.34 (M+H + ). Calcd for C 32 H 20 ClN

[0209]

[0210] Under N2atmosphere, 6 g (13.2 mmol) of intermediate X3-241-2, 4.5 g (13.9 mmol) of bis(4-biphenyl)amine, 0.24 g (0.26 mmol) of Pd2dba3, 0.22 g (0.52 mmol) of Sphos, 2.5 g (26.4 mmol) of sodium tert-butoxide were added to a four-necked flask, and then 50 ml of toluene was added, and the reaction was carried out by heating to 110°C. After the reaction was completed, the reaction solution was cooled to room temperature, and the reaction solution was extracted with dichloromethane, and the organic phase was dried over anhydrous sodium sulfate and then the solvent was removed. Purification was performed by silica gel chromatography (developing solvent: n-hexane: DCM = 3: 1 by volume). Thus, compound X3-241 was obtained as a white solid (9.2 g, 94%).

[0211] LC-MS (APCI): 739.57 (M+H + ). Calcd for C 56 H 38 N2

[0212] 1H NMR (400 MHz, Methylene Chloride-d2) δ 8.61 (dd, 1H), 8.43 - 8.38 (m, 1H), 8.28 (d, 1H), 8.01 - 7.95 (m, 1H), 7.90 (d, 1H), 7.86 - 7.52 (m, 8H), 7.44 - 7.25 (m, 12H), 7.24 - 7.13 (m, 4H), 7.12 - 6.92 (m, 6H), 6.82 (d, 1H), 6.76 (d, 1H), 6.61 (d, 1H).

[0213] Synthesis Example 2: Synthesis of compound X3-27

[0214]

[0215] Synthesis Example 2: Synthesis of compound X3-27

[0216] LC-MS (APCI): 713.57 (M+H+). Calcd for C54H36N2

[0217] 1H NMR (400 MHz, DMSO-d6) δ 8.53 (d, 1H), 8.19 - 8.14 (m, 1H), 8.12 - 8.07 (m, 1H), 8.04 - 7.70 (m, 8H), 7.63 - 7.49 (m, 4H), 7.48 - 7.40 (m, 1H), 7.39 - 7.16 (m, 7H), 7.14 - 6.99 (m, 6H), 6.96 - 6.81 (m, 2H), 6.53 (s, 5H).

[0218] Synthesis Example 3: Synthesis of compound X3-29

[0219]

[0220] Intermediate X3-241-2 (7.0 g, 15.4 mmol), 4-(naphthalen-2-yl)-N- phenylaniline (4.6 g, 15.4 mmol), sodium tert-butoxide (3.0 g, 30.8 mmol), 2- dicyclohexylphosphino-2',6'-dimethoxy-biphenyl (633 mg, 1.5 mmol), tris(dibenzylideneacetone)dipalladium (705 mg, 0.8 mmol) were added into a four-necked flask under nitrogen atmosphere, 100 mL of toluene was added, and the temperature was raised to 110 °C for 2 h. The reaction was completed, and the product was purified by column chromatography (eluent: n-hexane: dichloromethane = 1:1, volume ratio) to give compound X3-29 (5.9 g, 54% yield) as a white solid.

[0221] LC-MS (APCI): 713.57 (M+H+). Calcd for: C54H36N2

[0222] 1H NMR (400 MHz, Methylene Chloride-d2) δ 8.41 (d, 1H), 8.14 - 8.11 (m, 1H), 8.07 - 7.93 (m, 3H), 7.93 - 7.82 (m, 6H), 7.81 - 7.74 (m, 2H), 7.72 - 7.63 (m, 2H), 7.55 - 7.39 (m, 4H), 7.38 - 7.23 (m, 5H), 7.21 - 7.10 (m, 3H), 7.09 - 6.99 (m, 3H), 6.95 (d, 1H), 6.87 (td, 1H), 6.78 (dd, 1H), 6.60 (s, 3H).

[0223] Synthesis Example 4: Synthesis of compound X5-241

[0224] (1) Synthesis of intermediate X5-2

[0225]

[0226] X5-1 (12.00 g, 32.34 mmol), 4-chloro-1-naphthalenylboronic acid (6.66 g, 32.34 mmol), potassium carbonate (8.94 g, 64.68 mmol) and bis(triphenylphosphine)palladium(II) chloride (0.45 g, 0.65 mmol) were added into a four-necked flask under nitrogen atmosphere, 90 mL of THF and 30 mL of H2O were added, and the temperature was raised to 70 °C for 2 h. After the reaction was completed, the temperature of the reaction solution was lowered to 25 °C, 200 mL of water was added to the reaction solution, and the reaction solution was extracted with ethyl acetate, separated, and the organic phase was dried. The crude product was purified by silica gel chromatography (eluent: n-hexane: dichloromethane = 10:1, volume ratio) to give intermediate X5-2 (10.5 g, 72% yield) as a white solid.

[0227] (2) Synthesis of compound X5-241

[0228]

[0229] Under nitrogen atmosphere, intermediate X5-2 (6 g, 13.2 mmol), bis(4- biphenyl)amine (4.5 g, 13.9 mmol), tris(dibenzylideneacetone)dipalladium (0.24 g, 0.26 mmol), 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl (0.22 g, 0.52 mmol), sodium tert-butoxide (2.54 g, 26.4 mmol), 50 ml of toluene were added into a reaction flask, heated to 110°C for 5 hours. After the reaction was completed, the reaction solution was cooled to room temperature, 150 ml of water was added to the reaction solution, and the reaction solution was extracted with dichloromethane, separated, and the organic phase was dried with anhydrous sodium sulfate, and the organic phase was rotary evaporated to obtain a crude product. The crude product was purified by silica gel chromatography (developing solvent: n-hexane: dichloromethane = volume ratio 4:1) to obtain compound X5-241 (7.9 g, yield 81%) as a white solid.

[0230] LC-MS (APCI): 739.44 [M+H] + .Calcd for: C 56 H 38 N2, 738.30

[0231] 1 H NMR (400 MHz, Methylene Chloride-d2) δ 8.69 (s, 1H), 8.34 (dt, J = 7.7, 1.0 Hz, 1H), 8.24 - 8.19 (m, 1H), 8.14 (ddd, J = 16.4, 8.5, 1.3 Hz, 2H), 7.97 - 7.91 (m, 3H), 7.90 - 7.82 (m, 2H), 7.76 (dt, J = 7.4, 1.6 Hz, 1H), 7.66 (d, J = 7.5 Hz, 1H), 7.62 - 7.59 (m, 5H), 7.59 - 7.51 (m, 8H), 7.50 - 7.41 (m, 6H), 7.40 - 7.31 (m, 3H), 7.25 - 7.19 (m, 4H).

[0232] Synthesis Example 5: Synthesis of compound X3-163

[0233]

[0234] Intermediate X3-241-2 (6 g, 13.2 mmol), N-(3-biphenyl)-N-(4-biphenyl) amine (4.5 g, 13.9 mmol), tris(dibenzylideneacetone)dipalladium (0.24 g, 0.26 mmol), 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl (0.22 g, 0.52 mmol), sodium tert-butoxide (2.54 g, 26.4 mmol), 50 ml of toluene were charged into a reaction flask under nitrogen atmosphere, and the reaction was carried out at 110°C for 4 hours. After completion of the reaction, the reaction solution was cooled to room temperature, 100 ml of water was added to the reaction solution, and the reaction solution was extracted with dichloromethane, and separated. The organic phase was dried over anhydrous sodium sulfate, and the organic phase was distilled off to obtain a crude product. The crude product was purified by silica gel chromatography (developing solvent: n-hexane:dichloromethane = 3:1 by volume) to obtain compound X3-163 (8.8 g, yield 90%) as a white solid.

[0235] LC-MS (APCI): 739.41 [M+H] + .Calcd for: C 56 H 38 N2 738.30.

[0236] 1 H NMR (400 MHz, Methylene Chloride-d2) δ 8.77 - 8.68 (m, 1H), 8.55 - 8.50 (m, 1H), 8.38 (d, J = 8.0 Hz, 1H), 8.09 - 8.00 (m, 1H), 7.96 - 7.88 (m, 2H), 7.88 - 7.77 (m, 6H), 7.75 - 7.69 (m, 2H), 7.55 - 7.43 (m, 9H), 7.42 - 7.30 (m, 7H), 7.26 (ddt, J = 9.5, 7.2, 2.0 Hz, 1H), 7.20 - 7.08 (m, 5H), 6.91 (dd, J = 7.6, 4.7 Hz, 1H), 6.77 (d, J = 7.7 Hz, 1H).

[0237] Synthesis Example 6: Synthesis of compound X3-4

[0238]

[0239] Intermediate X3-241-2 (6.6 g, 14.5 mmol), N-phenyl-4-phenylaminoaniline (3.7 g, 15.3 mmol), tris(dibenzylideneacetone)dipalladium (0.26 g, 0.29 mmol), 2-bis(cyclohexylphosphino)-2',6'-dimethoxybiphenyl (0.24 g, 0.57 mmol), sodium tert-butoxide (2.8 g, 29 mmol), 70 ml of toluene were charged into a reaction flask under nitrogen atmosphere, and the reaction was allowed to proceed at 110°C for 4 hours. After completion of the reaction, the reaction solution was cooled to room temperature, 150 ml of water was added to the reaction solution, and the reaction solution was extracted with dichloromethane, and separated. The organic layer was dried over anhydrous sodium sulfate, and the organic layer was distilled off under reduced pressure to obtain a crude product. The crude product was purified by silica gel chromatography (developing solvent: n-hexane:dichloromethane = 4:1 by volume) to obtain compound X3-4 (7.2 g, yield 72%) as a white solid.

[0240] LC-MS (APCI): 663.47 [M+H] + Calcd for: C 50 H 34 N2 662.27.

[0241] 1 H NMR (400 MHz, Methylene Chloride-d2) δ 8.72 (ddd, J = 10.4, 8.4, 1.0 Hz, 1H), 8.55 - 8.36 (m, 1H), 8.08 - 7.99 (m, 1H), 7.97 - 7.58 (m, 8H), 7.53 - 7.23 (m, 11H), 7.15 - 6.85 (m, 8H), 6.73 - 6.36 (m, 4H).

[0242]

[0243] Under nitrogen atmosphere, intermediate X3-241-2 (6 g, 13.2 mmol), N-phenyl-[1,1':3',1"-terphenyl]-4-amine (4.5 g, 13.9 mmol), tris(dibenzylideneacetone)dipalladium (0.24 g, 0.26 mmol), 2-biscyclohexylphosphino-2',6'-dimethoxybiphenyl (0.22 g, 0.52 mmol), sodium tert-butoxide (2.54 g, 26.4 mmol), 50 ml of toluene were added into a reaction flask, heated to 110 °C for 4 hours. After the reaction was completed, the reaction liquid was cooled to room temperature, 150 ml of water was added to the reaction liquid, and the reaction liquid was extracted with dichloromethane, separated, and the organic phase was dried with anhydrous sodium sulfate, and the organic phase was rotary evaporated to obtain a crude product. The crude product was purified by silica gel chromatography (developing solvent: n-hexane: dichloromethane = volume ratio 4:1) to obtain compound X3-10 (7.6 g, yield 78%) as a white solid.

[0244] LC-MS (APCI): 739.39 [M+H] + .Calcd for: C 56 H 38 N2 738.30. The corresponding mass spectrum is shown in the description accompanying Figure 2 .

[0245] 1 H NMR (400 MHz, DMSO-d6) δ 8.69 (dd, J = 16.3, 8.4 Hz, 1H), 8.59 - 8.41 (m, 1H), 8.06 - 7.73 (m, 8H), 7.71 - 7.67 (m, 1H), 7.66 - 7.28 (m, 14H), 7.28 - 6.83 (m, 9H), 6.75 - 6.24 (m, 4H). The corresponding nuclear magnetic resonance spectrum is shown in the description accompanying Figure 3 .

[0246] Synthesis Example 8: Synthesis of compound X3-186

[0247]

[0248] Intermediate X3-241-2 (6 g, 13.2 mmol), N-(4-(1-naphthyl)phenyl)-1,1'- biphenyl-3-amine (5.2 g, 13.9 mmol), tris(dibenzylideneacetone)dipalladium (0.24 g, 0.26 mmol), 2-biscyclohexylphosphino-2',6'-dimethoxybiphenyl (0.22 g, 0.52 mmol), sodium tert-butoxide (2.54 g, 26.4 mmol), 50 ml of toluene were added into a reaction flask under nitrogen atmosphere, and the reaction was heated to 110°C for 4 hours. After the reaction was completed, the reaction solution was cooled to room temperature, 150 ml of water was added to the reaction solution, and the reaction solution was extracted with dichloromethane, and separated. The organic phase was dried with anhydrous sodium sulfate, and the organic phase was rotary evaporated to obtain a crude product. The crude product was purified by silica gel chromatography (developing solvent: n-hexane: dichloromethane = volume ratio 4:1) to obtain compound X3-186 (7.4 g, yield 71%) as a white solid.

[0249] LC-MS (APCI): 789.47 [M+H] + Calcd for: C 60 H 40 N2 788.32.

[0250] 1 H NMR (400 MHz, Methylene Chloride-d2) δ 8.67 (dd, J = 8.4, 5.5 Hz, 1H), 8.53 - 8.32 (m, 1H), 8.16 - 7.66 (m, 11H), 7.64 - 7.03 (m, 22H), 7.00 - 6.44 (m, 5H).

[0251] Synthesis Example 9: Synthesis of compound X3-17

[0252]

[0253] Under nitrogen atmosphere, intermediate X3-241-2 (6 g, 13.2 mmol), N-phenyl-[1,1':4',1"-terphenyl]-4-amine (4.5 g, 13.9 mmol), tris(dibenzylideneacetone)dipalladium (0.24 g, 0.26 mmol), 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl (0.22 g, 0.52 mmol), sodium tert-butoxide (2.54 g, 26.4 mmol), 50 ml of toluene were added into a reaction flask, heated to 110 °C for 5 hours. After the reaction was completed, the reaction liquid was cooled to room temperature, 150 ml of water was added to the reaction liquid, and the reaction liquid was extracted with dichloromethane, separated, and the organic phase was dried with anhydrous sodium sulfate, and the organic phase was rotary evaporated to obtain a crude product. The crude product was purified by silica gel chromatography (developing solvent: n-hexane: dichloromethane = volume ratio 3:1) to obtain compound X3-17 (8.3 g, yield 85%) as a white solid.

[0254] LC-MS (APCI): 739.46 [M+H] + .Calcd for: C 56 H 38 N2 738.30. The corresponding mass spectrum is shown in the description accompanying Figure 4 .

[0255] 1 H NMR (400 MHz, Methylene Chloride-d2) δ 8.74 (dd, J = 11.3, 8.4 Hz, 1H), 8.58 - 8.35 (m, 1H), 8.12 - 8.00 (m, 1H), 7.96 - 7.56 (m, 14H), 7.55 - 7.23 (m, 9H), 7.23 - 6.95 (m, 6H), 6.88 (t, J = 7.7 Hz, 2H), 6.81 - 6.29 (m, 4H). The corresponding nuclear magnetic resonance spectrum is shown in the description accompanying Figure 5 .

[0256] Synthesis Example 10: Synthesis of compound X3-264

[0257]

[0258] Under nitrogen atmosphere, intermediate X3-241-2 (6 g, 13.2 mmol), N-(4-(-1- naphthyl)phenyl)-4-benzenamine (5.2 g, 13.9 mmol), tris(dibenzylideneacetone)dipalladium (0.24 g, 0.26 mmol), 2-biscyclohexylphosphino-2',6'-dimethoxybiphenyl (0.22 g, 0.52 mmol), sodium tert-butoxide (2.54 g, 26.4 mmol), 60 ml of toluene were added into a reaction flask, heated to 110 °C for 4 hours. After the reaction was completed, the reaction solution was cooled to room temperature, 200 ml of water was added to the reaction solution, and the reaction solution was extracted with dichloromethane, separated, and the organic phase was dried with anhydrous sodium sulfate, and the organic phase was rotary evaporated to obtain a crude product. The crude product was purified by silica gel chromatography (developing solvent: n-hexane: dichloromethane = volume ratio 3:1) to obtain compound X3-264 (8.8 g, yield 85%) as a white solid.

[0259] LC-MS (APCI): 789.48 [M+H] + .Calcd for: C 60 H 40 N2 788.32. The corresponding mass spectrum is shown in the description attached Figure 6 .

[0260] 1 H NMR (400 MHz, DMSO-d6) δ 8.69 (dd, J = 15.6, 8.4 Hz, 1H), 8.49 (dd, J = 52.0, 7.7 Hz, 1H), 8.07 - 7.80 (m, 9H), 7.74 - 7.64 (m, 1H), 7.61 - 7.27 (m, 17H), 7.09 (dddd, J = 57.3, 28.9, 14.7, 7.1 Hz, 7H), 6.84 (d, J = 7.6 Hz, 1H), 6.63 (s, 3H).

[0261] Synthesis Example 11: Synthesis of compound X3-1891

[0262]

[0263] Under nitrogen atmosphere, intermediate X3-241-2 (6 g, 13.2 mmol), 4-(2-naphthyl)-N-[4-(2-naphthyl)phenyl]aniline (5.9 g, 13.9 mmol), tris(dibenzylideneacetone)dipalladium (0.24 g, 0.26 mmol), 2-bis(cyclohexylphosphino)-2',6'-dimethoxybiphenyl (0.22 g, 0.52 mmol), sodium tert-butoxide (2.54 g, 26.4 mmol), 60 ml of toluene were added into a reaction flask, heated to 110 °C for 4 hours. After the reaction was completed, the reaction solution was cooled to room temperature, 200 ml of water was added to the reaction solution, and the reaction solution was extracted with dichloromethane, separated, and the organic phase was dried with anhydrous sodium sulfate, and the organic phase was rotary evaporated to obtain a crude product. The crude product was purified by silica gel chromatography (developing solvent: n-hexane: dichloromethane = volume ratio 3:1) to obtain compound X3-1891 (7.2 g, yield 65%) as a white solid.

[0264] LC-MS (APCI): 839.49 [M+H] + .Calcd for: C 64 H 42 N2, 838.33.

[0265] 1 H NMR (400 MHz, Methylene Chloride-d2) δ 8.77 (ddd, J = 18.4, 8.5, 1.1 Hz, 1H), 8.57 - 8.41 (m, 1H), 8.15 - 8.03 (m, 1H), 8.02 - 7.88 (m, 10H), 7.87 - 7.79 (m, 4H), 7.78 - 7.67 (m, 4H), 7.57 - 7.49 (m, 6H), 7.47 - 7.41 (m, 2H), 7.41 - 7.16 (m, 6H), 7.16 - 7.03 (m, 2H), 7.03 - 6.32 (m, 5H).

[0266] Synthesis Example 12: Synthesis of compound X3-254

[0267]

[0268] Intermediate X3-241-2 (6 g, 13.2 mmol), N-(1,1-biphenyl)-1,1”.4”- triphenyl)amine (5.5 g, 13.9 mmol), tris(dibenzylideneacetone)dipalladium (0.24 g, 0.26 mmol), 2-biscyclohexylphosphino-2',6'-dimethoxybiphenyl (0.22 g, 0.52 mmol), sodium tert-butoxide (2.54 g, 26.4 mmol), 60 ml of toluene were added into a reaction flask under nitrogen atmosphere, and the reaction was allowed to proceed at 110°C for 5 hours. After completion of the reaction, the reaction solution was cooled to room temperature, 200 ml of water was added to the reaction solution, and the reaction solution was extracted with dichloromethane, and separated. The organic phase was dried over anhydrous sodium sulfate, and the organic phase was concentrated under reduced pressure to obtain a crude product. The crude product was purified by silica gel chromatography (developing solvent: n-hexane:dichloromethane = 3:1 by volume) to obtain compound X3-254 (9.1 g, yield 85%) as a white solid.

[0269] LC-MS (APCI): 815.51 [M+H] + Calcd for: C 62 H 42 N2 814.33.

[0270] 1 H NMR (400 MHz, Methylene Chloride-d2) δ 8.62 (dd, J = 16.5, 8.3 Hz, 1H), 8.42 (dd, J = 7.3, 1.4 Hz, 1H), 8.29 (d, J = 8.0 Hz, 1H), 7.98 (d, J = 8.5 Hz, 1H), 7.90 (dd, J = 8.2, 1.3 Hz, 1H), 7.84 – 7.53 (m, 13H), 7.51 – 7.45 (m, 2H), 7.44 – 7.24 (m, 11H), 7.24 – 6.93 (m, 8H), 6.83 (d, J = 7.6 Hz, 1H), 6.76 (d, J = 7.6 Hz, 1H), 6.61 (d, J = 7.7 Hz, 1H).

[0271] Synthesis Example 13: Synthesis of compound X1-241

[0272]

[0273] Under nitrogen atmosphere, intermediate X-1-1 (6 g, 13.2 mmol), bis(4-biphenyl)amine (4.5 g, 13.9 mmol), tris(dibenzylideneacetone)dipalladium (0.24 g, 0.26 mmol), 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl (0.22 g, 0.52 mmol), sodium tert-butoxide (2.54 g, 26.4 mmol), 50 ml of toluene were added into a reaction flask, heated to 110°C for 3 hours. After the reaction was completed, the reaction liquid was cooled to room temperature, 100 ml of water was added to the reaction liquid, the reaction liquid was extracted with dichloromethane, the organic phase was dried with anhydrous sodium sulfate, and the organic phase was rotary evaporated to obtain a crude product. The crude product was purified by silica gel chromatography (developing solvent: n-hexane: dichloromethane = volume ratio 4:1) to obtain compound X1-241 (7.3 g, yield 75%) as a white solid.

[0274] LC-MS (APCI): 739.40 [M+H] + .Calcd for: C 56 H 38 N2.

[0275] 1 H NMR (400 MHz, Methylene Chloride-d2) δ 8.59 (dd, 1H), 8.40-8.35 (m, 1H), 8.26 (d, 1H), 8.00-7.96 (m, 1H), 7.86 (d, 1H), 7.86-7.52 (m, 8H), 7.44-7.25 (m, 12H), 7.20-7.11 (m, 4H), 7.09-6.87 (m, 6H), 6.79 (d, 1H), 6.73 (d, 1H), 6.58 (d, 1H).

[0276] The following application examples further illustrate the organic electroluminescent element described in the present application.

[0277] Application Example 1:

[0278] The present embodiment provides an organic electroluminescent element, as shown in the following structure, comprising, from bottom to top, a substrate 1, an anode 2, a hole injection layer 3, a hole transport layer 4, an electron blocking layer 5, a light-emitting layer 6, a hole blocking layer 7, an electron transport layer 8, and a cathode 9. Figure 1

[0279] The specific device structure is as follows:

[0280] ​ITO / HT1-PD 3% (10 nm) / HT1 (60 nm) / HT2 (5 nm) / BH-BD 3% (20 nm) / HB (5 nm) / ET-LiQ 50% (30 nm) / Mg:Ag 1:9 (100 nm)

[0281] Device preparation process:

[0282] The bottom-emitting glass substrate 1 used in this embodiment was purchased from Guangdong Xingli Display Technology Co., Ltd., and ITO was used as the anode 2. First, the bottom-emitting glass substrate was cleaned with ITO cleaning agent, deionized water, and isopropanol in sequence, and then the bottom-emitting glass substrate was baked at 180 degrees Celsius for 30 minutes to dry it.

[0283] Then the bottom-emitting glass substrate was placed into an evaporation chamber, and each organic layer was deposited on the ITO anode by thermal vacuum evaporation at a rate of 0.2-2 angstroms per second under a vacuum degree of about 10 -8 angstroms per second. Among them, 3% PD was doped on HT1 to form a thickness of 10 nm as a hole injection layer 3, HT1 was formed to a thickness of 60 nm as a hole transport layer 4, HT2 was evaporated on HT1 to a thickness of 5 nm as an electron blocking layer 5, 3% BD was doped on the anthracene host BH to form a blue light-emitting layer 6 with a thickness of 20 nm, HB was formed to a thickness of 5 nm as a hole blocking layer 7, ET doped with 50% LiQ was formed to an electron transport layer 8 with a thickness of 30 nm, Mg:Ag (1:9) was formed to a thickness of 100 nm as a cathode 9. Finally, the device was transferred back to the glove box and packaged with a glass cover and a moisture absorbent to complete the device, which is denoted as organic electronic element 1. In this device embodiment, different materials are co-evaporated for the same layer, which exists in the layer in a certain volume ratio, for example, 50% LiQ, which is ET 50%, LiQ 50% in volume ratio. The materials for preparing the device of the present application are purified by sublimation, and the purity is above 99.9%.

[0284] The synthesis method of HT2 is the same as X3-241, wherein bis(4-biphenyl)amine is replaced with CAS: 1592944-27-8, and X3-241-2 is replaced with CAS: 1464824-91-6, (LC-MS (APCI): 739.51 (M+H+)). The evaporation temperature of HT2 is 420 degrees Celsius.

[0285]

[0286]

[0287] Examples and comparative examples

[0288] An organic electronic element 2 was produced in the same manner as in Example 1, except that the compound X3-241 prepared in the synthesis example of the present application was used instead of HT2 for the electron blocking layer. The evaporation temperature of X3-241 was 353°C.

[0289] An organic electronic element 5 was produced in the same manner as in Example 1, except that the compound HT-3 was used instead of HT2 for the electron blocking layer. The evaporation temperature of HT-3 was 345°C.

[0290] An organic electronic element 6 was produced in the same manner as in Example 1, except that the compound HT-4 was used instead of HT2 for the electron blocking layer. The evaporation temperature of HT-4 was 419°C.

[0291] An organic electronic element 7 was produced in the same manner as in Example 1, except that the compound HT-5 was used instead of HT2 for the electron blocking layer. The evaporation temperature of HT-5 was 397°C.

[0292] An organic electronic element 8 was produced in the same manner as in Example 1, except that the compound HT-6 was used instead of HT2 for the electron blocking layer. The evaporation temperature of HT-6 was 403°C. An organic electronic element 3 was produced in the same manner as in Example 1, except that the compound X3-27 prepared in the synthesis example of the present application was used instead of HT2 for the electron blocking layer. The evaporation temperature of X3-27 was 336°C.

[0293] An organic electronic element 4 was produced in the same manner as in Example 1, except that the compound X3-29 prepared in the synthesis example of the present application was used instead of HT2 for the electron blocking layer. The evaporation temperature of X3-29 was 347°C.

[0294] An organic electronic element 9 was produced in the same manner as in Example 1, except that the compound X5-241 prepared in the synthesis example of the present application was used instead of HT2 for the electron blocking layer. The evaporation temperature of X5-241 was 389°C.

[0295] An organic electronic element 10 was produced in the same manner as in Example 1, except that the compound X3-163 prepared in the synthesis example of the present application was used instead of HT2 for the electron blocking layer. The evaporation temperature of X3-163 was 348°C.

[0296] An organic electronic element 11 was produced in the same manner as in Example 1, except that the compound X3-4 prepared in the synthesis example of the present application was used instead of HT2 for the electron blocking layer. The evaporation temperature of X3-4 was 320°C.

[0297] An organic electronic element 12 was produced in the same manner as in Example 1, except that the compound X3-10 prepared in the synthesis example of the present application was used instead of HT2 for the electron blocking layer. The evaporation temperature of X3-10 was 352°C.

[0298] The compound X3-186 obtained by the synthesis of Example 8 of the present application was used instead of HT2 to prepare the electron blocking layer, and an organic electronic device 13 was produced in the same manner. The evaporation temperature of X3-186 was 350°C.

[0299] The compound X3-17 obtained by the synthesis of Example 9 of the present application was used instead of HT2 to prepare the electron blocking layer, and an organic electronic device 14 was produced in the same manner. The evaporation temperature of X3-17 was 355°C.

[0300] The compound X3-264 obtained by the synthesis of Example 10 of the present application was used instead of HT2 to prepare the electron blocking layer, and an organic electronic device 15 was produced in the same manner. The evaporation temperature of X3-264 was 355°C.

[0301] The compound X3-1891 obtained by the synthesis of Example 11 of the present application was used instead of HT2 to prepare the electron blocking layer, and an organic electronic device 16 was produced in the same manner. The evaporation temperature of X3-1891 was 391°C.

[0302] The compound X3-254 obtained by the synthesis of Example 12 of the present application was used instead of HT2 to prepare the electron blocking layer, and an organic electronic device 17 was produced in the same manner. The evaporation temperature of X3-254 was 361°C.

[0303] The compound X1-241 obtained by the synthesis of Example 13 of the present application was used instead of HT2 to prepare the electron blocking layer, and an organic electronic device 18 was produced in the same manner. The evaporation temperature of X1-241 was 391°C.

[0304] Evaluation of Organic Electroluminescent Device

[0305] The driving voltage was 2.8 V at a current density of 15 mA / cm 2 The test was performed under the following conditions.

[0306] Method for Life Test: A voltage was applied to the obtained organic electroluminescent device so that the current density reached 60 mA / cm 2 , and the time until the luminance became 95% of the initial luminance (LT95 (unit: hours)) was measured.

[0307] Electronic barrier layer Driving voltage, V LT 95 / hour Organic electronic element 1 (device comparative example 1) HT-2 3.99 44 Organic electronic element 5 (device comparative example 2) HT-3 3.99 45 Organic electronic element 6 (device comparative example 3) HT-4 3.97 41 Organic electronic element 7 (device comparative example 4) HT-5 4.01 35 Organic electronic element 8 (device comparative example 5) HT-6 4.03 26 Organic electronic element 2 (synthesis example 1) X3-241 3.97 62 Organic electronic element 3 (synthesis example 2) X3-27 3.92 48 Organic electronic element 4 (synthesis example 3) X3-29 3.91 50 Organic electronic element 9 (synthesis example 4) X5-241 3.90 67 Organic electronic element 10 (synthesis example 5) X3-163 3.94 65 Organic electronic element 11 (synthesis example 6) X3-4 3.92 61 Organic electronic element 12 (synthesis example 7) X3-10 3.89 63 Organic electronic element 13 (synthesis example 8) X3-186 3.91 60 Organic electronic element 14 (synthesis example 9) X3-17 3.94 66 Organic electronic element 15 (synthesis example 10) X3-264 3.93 62 Organic electronic element 16 (synthesis example 11) X3-1891 3.96 63 Organic electronic element 17 (synthesis example 12) X3-254 3.93 70 Organic electronic element 18 (synthesis example 13) X1-241 3.98 46

[0308] The organic electroluminescent devices 2-4, 9-18 and the organic electronic devices 1, 5-8 prepared from the compounds of the present application have lower driving voltage and longer lifetime, thus the compounds of the present application are suitable for preparing high performance organic electroluminescent devices. The compounds X3-241, X3-27, X3-29, X5-241, X3-163, X3-4, X3-10, X3-186, X3-17, X3-264, X3-1891, X3-254 have significantly lower evaporation temperature than HT2, HT-3, HT-4, HT-5, HT-6, HT-7, can withstand longer heating, and are beneficial to industrial use.

[0309] Those skilled in the art will readily understand that the above description is only preferred embodiments of the present application, and is not intended to limit the present application, and any modifications, equivalent replacements and improvements made within the spirit and principle of the present application shall be included in the protection scope of the present application.

Claims

1. An organic electroluminescent element comprising an anode, a cathode, and a light-emitting layer between the anode and the cathode, characterized in that a first organic layer is contained between the anode and the light-emitting layer, the first organic layer containing a compound represented by Structural Formula (1), L 1 , L 2 each independently is selected from a single bond, substituted or unsubstituted C6-C30 arylene, substituted or unsubstituted C3-C30 N-free heteroarylene, Ar 1 , Ar 2 each independently is selected from the group consisting of hydrogen, substituted or unsubstituted C6-C30aryl, substituted or unsubstituted C3-C30N-free heteroaryl, the substituent in the substituted or unsubstituted is free from N.

2. The organic electroluminescent element according to claim 1, wherein Formula (1) is selected from Formula (2), (3), or (4), L 1 、L 2 、Ar 1 、Ar 2 as defined in claim 1.

3. The organic electroluminescent element according to claim 1, wherein Formula (1) is selected from Formula (2-1), (2-2), (2-3), (3-1), (3-2), (3-3), (4-1), (4-2), (4-3), L 1 、L 2 、Ar 1 、Ar 2 as defined in claim 1.

4. The organic electroluminescent element according to claim 1, wherein Formula (1) is selected from Formula (2-2), (2-3), L 1 , L 2 , Ar 1 , Ar 2 as defined in formula (1); Preferably, Formula (1) is selected from Formula (2-3), L 1 、L 2 、Ar 1 、Ar 2 as defined in formula (1).

5. The organic electroluminescence element according to any one of claims 1 to 4, wherein L 1 、L 2 each independently is selected from a single bond, substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted anthrylene, substituted or unsubstituted phenanthrylene, substituted or unsubstituted biphenylene, substituted or unsubstituted terphenylene, substituted or unsubstituted phenylnaphthylene, substituted or unsubstituted dibenzofuranylene, substituted or unsubstituted dibenzothiophenylene, substituted or unsubstituted 9,9'-dimethylfluorenylene, substituted or unsubstituted 9,9'-diphenylfluorenylene, substituted or unsubstituted spirobifluorenylene.

6. The organic electroluminescence element according to any one of claims 1 to 4, wherein Ar 1 , Ar 2 each independently is selected from hydrogen, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthryl, substituted or unsubstituted phenanthryl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted phenylnaphthyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted 9,9'-dimethylfluorenyl, substituted or unsubstituted 9,9'-diphenylfluorenyl, substituted or unsubstituted spirobifluorenyl.

7. The organic electroluminescence element according to any one of claims 1 to 4, wherein said L 1 , L 2 each independently is selected from a single bond, a substituted or unsubstituted group: dotted line represents a substitution position.

8. The organic electroluminescence element according to any one of claims 1 to 4, wherein said Ar 1 , Ar 2 each independently is selected from the group consisting of hydrogen, a substituted or unsubstituted dotted line represents a substitution position.

9. The organic electroluminescence element according to any one of claims 1 to 4, wherein -L 1 -Ar 1 , -L 2 -Ar 2 each independently is selected from the group consisting of hydrogen, one of Y1to Y81, dotted line represents a substitution position.

10. The compound of claim 1, wherein the compound is selected from the structures shown by 11. The first organic layer of any one of claims 1 to 10 is a light-emitting auxiliary layer, an electron-blocking layer, a hole-transporting layer, a charge-generating layer, or a hole-injecting layer.

12. The first organic layer of any one of claims 1 to 10 is an electron-blocking layer, adjacent to the light-emitting layer.

13. The organic electroluminescent element of any one of claims 1 to 10 is a single-layer element or a stacked-layer element.

14. An electronic device comprising the organic electroluminescent element of any one of claims 1 to 13.

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