Organic electroluminescent element and electronic equipment comprising same

Abstract

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

Description

An organic electroluminescent element and an electronic device comprising the same.

[0001] Cross-references to related applications

[0002] This application claims priority and benefits to the following Chinese patent application filed with the China National Intellectual Property Administration, the entire contents of which are incorporated herein by reference:

[0003] Chinese patent application filed on April 24, 2024, with application number CN202410496269.7 and application title "An organic electroluminescent element and an electronic device including the same".

[0004] Chinese patent application filed on April 23, 2025, with application number CN202510515832.5 and application title "An organic electroluminescent element and an electronic device including the same". Technical Field

[0005] This invention relates to the field of organic electroluminescence technology, and more specifically, to an organic electroluminescent element and an electronic device. Background Technology

[0006] Organic light-emitting diodes (OLEDs) consist of an anode, a cathode, and one or more organic thin film layers sandwiched between the anode and cathode. When a voltage is applied between the two electrodes, electrons are injected into the light-emitting region from the cathode side, and holes are injected into the light-emitting region from the anode side. The injected electrons and holes recombine in the light-emitting region to generate an excited state, which emits light when it returns to the ground state. In recent years, with the increasing popularity of smartphones, televisions, and lighting using OLEDs, there is a demand for materials that can meet the requirements of device lifespan while reducing the driving voltage. Summary of the Invention

[0007] The purpose of this invention is to provide an organic electroluminescent element with improved driving voltage and lifetime.

[0008] Technical solution

[0009] This invention provides an organic electroluminescent element comprising an anode, a cathode, and a light-emitting layer located between the anode and the cathode, characterized in that a first organic layer is included between the anode and the light-emitting layer, the first organic layer comprising a compound represented by structural formula (1).

[0010] L 1 L 2 Each is independently selected from single-bonded, substituted or unsubstituted C6-C30 arylene groups, or substituted or unsubstituted C3-C30 N-free heteroarylene groups.

[0011] Ar1 Ar 2 Each is independently selected from hydrogen, substituted or unsubstituted C6-C30 aryl groups, or substituted or unsubstituted C3-C30 non-N heteroaryl groups.

[0012] The substituents in the substituted or unsubstituted form do not contain N;

[0013] Preferably, the compound represented by the structural formula (1) may not contain or may contain at least one substituent selected from deuterium, fluorine, or cyano; more preferably, the compound represented by the structural formula (1) may not contain or may contain at least one substituent selected from deuterium or fluorine; more preferably, the compound represented by the structural formula (1) may not contain or may contain at least one deuterium.

[0014] Preferably, the substituted or unsubstituted C6-C30 aryl group does not contain phenanthrene, and the substituted or unsubstituted C6-C30 aryl group does not contain phenanthrene;

[0015] Preferably, the substituents in the substituted or unsubstituted form do not contain phenanthrene groups.

[0016] One embodiment of the present invention is that formula (1) is selected from formula (2), (3) or (4).

[0017] L 1 L 2 Ar 1 Ar 2 Define the same as equation (1);

[0018] Preferably, the compound may not contain or may contain at least one substituent selected from deuterium, fluorine, or cyano; more preferably, the compound may not contain or may contain at least one substituent selected from deuterium or fluorine; more preferably, the compound may not contain or may contain at least one deuterium.

[0019] One embodiment of the present invention is that formula (1) is selected from formulas (2-1), (2-2), (2-3), (3-1), (3-2), (3-3), (4-1), (4-2), and (4-3).

[0020] L 1 L 2 Ar 1 Ar 2 Define the same as equation (1);

[0021] Preferably, the compound may not contain or may contain at least one substituent selected from deuterium, fluorine, or cyano; more preferably, the compound may not contain or may contain at least one substituent selected from deuterium or fluorine; more preferably, the compound may not contain or may contain at least one deuterium.

[0022] One embodiment of the present invention is that formula (1) is selected from formulas (2-2), (2-3), (3-2), (3-3), (4-2), and (4-3).

[0023] L 1 L 2 、Ar 1 、Ar 2 Define the same as equation (1);

[0024] Preferably, the compound may not contain or may contain at least one substituent selected from deuterium, fluorine, or cyano; more preferably, the compound may not contain or may contain at least one substituent selected from deuterium or fluorine; more preferably, the compound may not contain or may contain at least one deuterium.

[0025] One embodiment of the present invention is that formula (1) is selected from formulas (2-2) and (2-3).

[0026] L 1 L 2 、Ar 1 、Ar 2 Define the same as equation (1);

[0027] Preferably, the compound may not contain or may contain at least one substituent selected from deuterium, fluorine, or cyano; more preferably, the compound may not contain or may contain at least one substituent selected from deuterium or fluorine; more preferably, the compound may not contain or may contain at least one deuterium.

[0028] One embodiment of the present invention is that formula (1) is selected from formula (2-3).

[0029] L 1 L 2 、Ar 1 、Ar 2 Define the same as equation (1);

[0030] Preferably, the compound may not contain or may contain at least one substituent selected from deuterium, fluorine, or cyano; more preferably, the compound may not contain or may contain at least one substituent selected from deuterium or fluorine; more preferably, the compound may not contain or may contain at least one deuterium.

[0031] In one embodiment of the present invention, L in formulas (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 is independently selected from single bonds, substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted anthracene, substituted or unsubstituted phenanthylene, substituted or unsubstituted biphenylene, substituted or unsubstituted terphenylene, substituted or unsubstituted phenylnaphthylene, substituted or unsubstituted dibenzofuranylene, substituted or unsubstituted dibenzothiopheneylene, substituted or unsubstituted 9,9'-dimethylfluoreneylene, substituted or unsubstituted 9,9'-diphenylfluoreneylene, substituted or unsubstituted spirodifluoreneylene.

[0032] In one embodiment of the present invention, Ar in formulas (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 is independently selected from hydrogen, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthraquinone, substituted or unsubstituted phenanthrene, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted phenylnaphthyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted 9,9'-dimethylfluorenyl, substituted or unsubstituted 9,9'-diphenylfluorenyl, substituted or unsubstituted spirodifluorenyl; preferably Ar 1 Ar 2 Fiki that is neither replaced nor substituted.

[0033] In one embodiment of the present invention, L in formulas (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 of the following groups, independently selected from single bonds, substituted or unsubstituted groups:

[0034] dotted line It represents replacing a position.

[0035] In one embodiment of the present invention, Ar in formulas (1), (2), (3), (2-1), (2-2), (2-3), (3-1), (3-2), (3-3), (4-1), (4-2), (4-3) 1 Ar 2Each of the following groups, independently selected from hydrogen, substituted or unsubstituted, is selected:

[0036] dotted line Represents replacing a position;

[0037] Preferably, the above groups do not contain

[0038] In one embodiment of the present invention, -L in formulas (1), (2), (3), (2-1), (2-2), (2-3), (3-1), (3-2), (3-3), (4-1), (4-2), (4-3) 1 -Ar 1 -L 2 -Ar 2 Each is independently selected from hydrogen,

[0039] dotted line Represents replacing a position;

[0040] Preferably, the above-mentioned groups are unsubstituted or substituted with one or more substituents selected from deuterium, fluorine, and cyano; more preferably, the above-mentioned groups are unsubstituted or substituted with one or more substituents selected from deuterium and fluorine; more preferably, the above-mentioned groups are unsubstituted or substituted with one or more deuterium groups; even more preferably, the above-mentioned groups are unsubstituted or substituted with one or more deuterium groups; most preferably, the above-mentioned groups are unsubstituted.

[0041] Preferably, the above-L 1 -Ar 1 -L 2 -Ar 2 None of the groups are

[0042] In the "substituted or unsubstituted" of this invention, the substituents are independently selected from deuterium, halogen, cyano, C1-C10 alkyl, C3-C10 cycloalkyl, C1-C10 alkoxy, C2-C10 alkenyl, C2-C10 alkynyl, C6-C60 aryl, C3-C60 heteroaryl, and C3-C60 heterocyclic, wherein the heteroatom in the heterocyclic group or heteroaryl group is selected from at least one of O and S;

[0043] Preferably, the substituents used in the "substituted or unsubstituted" designation of this invention are independently selected from deuterium, halogen, cyano, methyl, ethyl, propyl, n-butyl, tert-butyl, cyclopentyl, cyclohexyl, adamantyl, fluorenyl, spirofluorenyl, phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthryl, pyrene, fluoranyl, triphenylene, etc. The group is selected from one or more combinations of the following: alkyl, dibenzofuranyl, dibenzothiophenyl, furanyl, triazine, thiophenyl, benzothiophenyl, benzofuranyl, methoxy, ethoxy, propoxy, n-butoxy, tert-butoxy, and phenylnaphthyl; preferably selected from deuterium, halogen, cyano, methyl, ethyl, tert-butyl, cyclopentyl, cyclohexyl, adamantyl, fluorenyl, spirofluorenyl, phenyl, biphenyl, terphenyl, naphthyl, anthraceneyl, and dibenzofuranyl. The compound is selected from one or more combinations of alkyl, dibenzothiophenyl, furanyl, benzothiophenyl, benzofuranyl, methoxy, tert-butoxy, thiophenyl, and phenylnaphthyl; more preferably selected from one or more combinations of deuterium, halogen, cyano, methyl, ethyl, tert-butyl, cyclopentyl, adamantyl, fluorenyl, spirofluorenyl, phenyl, biphenyl, terphenyl, naphthyl, anthraceneyl, dibenzofuranyl, dibenzothiophenyl, benzothiophenyl, benzofuranyl, and methoxy. A variety of combinations; particularly preferably selected from one or more of deuterium, halogen, cyano, methyl, ethyl, tert-butyl, fluorenyl, spirofluorenyl, phenyl, biphenyl, terphenyl, naphthyl, anthracene, dibenzofuranyl, dibenzothiophene, and phenylnaphthyl; especially preferably selected from one or more of deuterium, halogen, cyano, methyl, ethyl, tert-butyl, phenyl, naphthyl, biphenyl, and phenylnaphthyl; particularly preferably selected from one or more of deuterium, fluorine, cyano, phenyl, naphthyl, biphenyl, and phenylnaphthyl; particularly preferably selected from one or more of deuterium, fluorine, phenyl, naphthyl, and biphenyl; particularly preferably selected from one or more of deuterium, phenyl, and biphenyl; particularly preferably selected from one or more of deuterium and phenyl; most preferably deuterium;

[0044] Examples of the various combinations include deuterated phenyl, deuterated methyl, methyl-substituted phenyl, deuterated methyl-substituted phenyl, etc.

[0045] In one embodiment of the present invention, formula (1) is selected from the structures shown by the following compounds.

[0046] In one embodiment of the present invention, formula (1) is used It means that X n Selected from any of the following groups X1-X9,

[0047] When X nSelected from group X1, -L 1 -Ar 1 -L 2 -Ar 2 The compounds selected from the table below are numbered X1-1 to X1-3321.

[0048] X2 replaces X1, -L 1 -Ar 1 -L 2 -Ar 2 Selecting from the table above, the compounds are numbered X2-1 to X2-3321.

[0049] X3 replaces X1, -L 1 -Ar 1 -L 2 -Ar 2 Selecting from the table above, the compounds are numbered X3-1 to X3-3321.

[0050] X4 replaces X1, -L 1-Ar 1 -L 2 -Ar 2 Selecting from the table above, the compounds are numbered X4-1 to X4-3321.

[0051] X5 replaces X1, -L 1 -Ar 1 -L 2 -Ar 2 Selecting from the table above, the compounds are numbered X5-1 to X5-3321.

[0052] X6 replaces X1, -L 1 -Ar 1 -L 2 -Ar 2 Selecting from the table above, the compounds are numbered X6-1 to X6-3321.

[0053] X7 replaces X1, -L 1 -Ar 1 -L 2 -Ar 2 Selected from the table above, the compounds are numbered X7-1 to X7-3321.

[0054] X8 replaces X1, -L 1 -Ar 1 -L 2 -Ar 2 Selecting from the table above, the compounds are numbered X8-1 to X8-3321.

[0055] X9 replaces X1, -L 1 -Ar 1 -L 2 -Ar 2 Selected from the table above, the compounds are numbered X9-1 to X9-3321.

[0056] In another embodiment of the present invention, the first organic layer is a light-emitting auxiliary 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 light-emitting auxiliary layer, an electron blocking layer, a P-type charge generation layer, or a hole transport layer; more preferably, the first organic layer is a light-emitting auxiliary layer, an electron blocking layer, or a hole transport layer; more preferably, the first organic layer is a light-emitting auxiliary layer, an electron blocking layer, or a second hole transport layer; most preferably, the first organic layer is a light-emitting auxiliary 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.

[0057] In another embodiment of the present invention, the organic electroluminescent element is a single-layer element or a multilayer element.

[0058] 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 adjacent to the light-emitting layer.

[0059] In another embodiment of the present invention, the organic electroluminescent element is a stacked element, the stacked element comprising two or more light-emitting units, each light-emitting unit comprising a light-emitting layer, each light-emitting unit comprising a first organic layer, the first organic layer being located between the anode and each light-emitting unit, the plurality of first organic layers being made of the same or different materials, wherein at least one 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, particularly preferably a light-emitting auxiliary layer, an electron blocking layer, or a second hole transport layer, and especially preferably a light-emitting auxiliary layer or an electron blocking layer.

[0060] In another embodiment of the present invention, the organic electroluminescent element is a stacked element, the stacked element 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 first organic layer is an electron blocking layer, adjacent to the light-emitting layer in each light-emitting unit, the multiple electron blocking layers are made of the same or different materials, and at least one of the electron blocking layers is selected from the compound represented by the above formula (1).

[0061] A second object of the present invention is to provide an electronic device comprising the organic electroluminescent element described herein.

[0062] In summary, compared with the prior art, the above-described technical solutions conceived by this invention can achieve the following beneficial effects:

[0063] 1. The organic electroluminescent element of the present invention uses a specific material (structure: benzocarbazole-phenylene-naphthylene-substituted amine), especially when the electron blocking layer uses this material. By introducing the rigid structure of benzocarbazole-phenylene-naphthylene, molecular stacking can be effectively controlled, avoiding excessive disordered arrangement, giving the material better film-forming properties and thermal stability, which is beneficial to improving the service life of organic electroluminescent devices. The prepared element exhibits excellent performance. Attached Figure Description

[0064] Figure 1 is a schematic diagram of the structure of the organic electroluminescent element described in Application Example 1; wherein: the labels in Figure 1 represent: 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.

[0065] Figure 2 is the mass spectrum of compound X3-10 prepared in synthesis example 7 of the compound preparation examples.

[0066] Figure 3 is the NMR spectrum of compound X3-10 prepared in synthesis example 7 in the compound preparation examples.

[0067] Figure 4 is the mass spectrum of compound X3-17 prepared in synthesis example 9 of the compound preparation examples.

[0068] Figure 5 is the NMR spectrum of compound X3-17 prepared in synthesis example 9 of the compound preparation examples.

[0069] Figure 6 is the mass spectrum of compound X3-264 prepared in synthesis example 10 in the compound preparation examples. Detailed Implementation

[0070] Exemplary embodiments will now be described in detail, examples of which are illustrated in the accompanying drawings, wherein the same reference numerals always refer to the same elements. In this respect, the exemplary embodiments may take different forms and should not be construed as limited to the description set forth herein. Therefore, the exemplary embodiments are described below only with reference to the accompanying drawings to illustrate the invention. As used herein, the term “and / or” includes any and all combinations of one or more of the associated enumerated items. Expressions such as “at least one of” modify the entire list of elements when preceding or following the list of elements, but do not modify individual elements of the list.

[0071] It will be understood that when an element is referred to as being "on" another element, it may be in direct contact with the other element or there may be an intermediate element between them. Conversely, when an element is referred to as being "directly on" another element, there is no intermediate element.

[0072] It will be further understood that the terms “comprising” or “including” as used in this specification indicate the presence of the stated features, regions, integrals, steps, operations, elements, and / or components, but do not preclude the presence or addition of one or more additional features, regions, integrals, steps, operations, elements, components, and / or sets thereof.

[0073] Unless otherwise defined, all terms used herein (including technical and scientific terms) have the same meaning as commonly understood by one of ordinary skill in the art to which this general inventive concept pertains. It will be further understood that terms, such as those defined in commonly used dictionaries, should be interpreted as having meanings consistent with their meanings in the relevant field and in the context of this disclosure, and will not be interpreted in an idealized or overly formal sense unless clearly defined herein.

[0074] The present invention will be further illustrated below with reference to specific embodiments. It should be understood that these embodiments are for illustrative purposes only and are not intended to limit the scope of protection of the present invention. Furthermore, it should be understood that after reading the disclosure of this invention, those skilled in the art can make various modifications or alterations to the present invention, and these equivalent forms also fall within the scope of protection defined by this invention.

[0075] Unless otherwise specified, the experimental methods used in the following examples are conventional methods; unless otherwise specified, the reagents and materials used in the following examples are commercially available.

[0076] Terminology Explanation

[0077] As used in this invention, the term "halogen" may include fluorine, chlorine, bromine, or iodine.

[0078] As used in this invention, the term "C1-C10 alkyl" refers to a monovalent substituent derived from a straight-chain or branched saturated hydrocarbon having 1 to 10 carbon atoms, examples of which include, but are not limited to, methyl, ethyl, propyl, isobutyl, sec-butyl, tert-butyl, pentyl, isopentyl, and hexyl.

[0079] As used herein, the term "C3-C10 cycloalkyl" refers to a monovalent substituent derived from a monocyclic or polycyclic nonaromatic hydrocarbon having 3 to 10 carbon atoms. Examples of such cycloalkyl groups include, but are not limited to, cyclopropane, cyclobutane, cyclopentane, cyclohexane, norbornyl, adamantane, etc.

[0080] As used in this invention, the term "C2-C10 alkenyl" refers to a monovalent substituent derived from a straight-chain or branched unsaturated hydrocarbon having one or more carbon-carbon double bonds and having 2 to 10 carbon atoms. Examples include, but are not limited to, vinyl, propenyl, isopropenyl, 2-butenyl, etc.

[0081] As used in this invention, the term "C2-C10 alkynyl" refers to a monovalent substituent derived from a straight-chain or branched unsaturated hydrocarbon having one or more carbon-carbon triple bonds and having 2 to 10 carbon atoms. Examples include, but are not limited to, ethynyl, 2-propynyl, etc.

[0082] As used in this invention, the term "C3-C60 heterocyclic group" refers to a monovalent substituent derived from a monocyclic or polycyclic ring having 3 to 60 carbon atoms, wherein the ring contains at least one heteroatom selected from O and S.

[0083] As used herein, the term "alkoxy" refers to a straight-chain, branched, or cyclic chain. The number of carbon atoms in an alkoxy group is not particularly limited herein, but it is preferred to have 1 to 10 carbon atoms. Specific examples include, but are not limited to, methoxy, ethoxy, n-propoxy, isopropoxy, isopropoxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentoxy, neopentoxy, isopentoxy, n-hexyloxy, and benzyloxy.

[0084] 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 6 to 60 carbon atoms. Further, such an aryl group may have two or more rings simply side-attached to or fused together with each other. Examples of such aryl groups include, but are not limited to, phenyl, biphenyl, naphthyl, phenanthryl, anthracene, pyrene, triphenylene, fluoranthyl, dimethyl-9,9-dimethylfluorene, 9,9-diphenylfluorene, spirodifluorene, etc.

[0085] As used in this invention, the term "arylene" refers to a divalent aryl group derived by removing one hydrogen atom from an "aryl" group, for example, a phenyl group by removing one hydrogen atom to form a phenylene group, and a naphthyl group by removing one hydrogen atom to form a naphthylene group.

[0086] As used herein, the term "C3-C60 heteroaryl" refers to a monovalent substituent derived from a monoheterocyclic or polyheterocyclic aromatic hydrocarbon having 3 to 60 carbon atoms. In this connection, at least one carbon atom, preferably 1 to 3 carbons, in the ring is substituted with a heteroatom, such as O or S. Furthermore, such heteroaryl can be in the form where two or more rings are simply side-attached to each other, fused together, or fused with an aryl group. Examples of such heteroaryl include, but are not limited to, furanyl, thiopheneyl, benzofuranyl, benzothiopheneyl, dibenzofuranyl, and dibenzothiopheneyl.

[0087] As used in this invention, the term "hybrid aryl" refers to a divalent heteroaryl derived by removing a hydrogen atom from a "heteroaryl".

[0088] As used in this invention, the expression "K group with MN carbon atoms" or "K group with C(MN)" means that the K group has no carbon atoms when it is unsubstituted, excluding the number of carbon atoms of the substituents when substituted. For example, an aryl group with C6-C60 means that when it is unsubstituted, the number of carbon atoms in the aryl group is any integer from 6 to 60. That is, when it is unsubstituted, the number of carbon atoms can be 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20...60.

[0089] As used in this invention, the term "substituted" means that a hydrogen atom in a compound is replaced by another substituent. The substitution can occur at any position where the hydrogen atom is substituted. That is, the position is not limited to a specific position, as long as the hydrogen at that position can be replaced by a substituent. "Unsubstituted" means that the hydrogen atom is retained, in which case the hydrogen atom includes protium, deuterium, and tritium, and substitution may also include deuterium and tritium substitution.

[0090] When two or more substituents are present, the two or more substituents can be the same or different.

[0091] As used in this invention, the term "terphenyl" includes

[0092] As used in this invention, the term "phenylnaphthyl" includes, but is not limited to, […].

[0093] As used in this invention, the term "phenylenenaphthyl" includes, but is not limited to, […].

[0094] As used in this invention, hydrogen atoms include protium, deuterium, and tritium. The compounds of this invention may contain naturally occurring deuterium atoms, or deuterium atoms may be introduced by deuterating part or all of the starting material compound. If deuterium atoms are introduced from the starting material, the deuteration rate may be 100%, less than 100%, less than 95%, less than 90%, or less than 80%, or may be more than 1%, more than 5%, or more than 10%. If the deuteration rate is not 100%, it represents a mixture of deuterated and undeuterated compounds, or a mixture of fully deuterated and incompletely deuterated compounds, or a mixture of fully deuterated, undeuterated, and incompletely deuterated compounds.

[0095] As used in this invention, terms such as 1, 2, A, B, etc. are used. These terms are only used to distinguish constituent elements and do not limit the nature or order of the constituent elements corresponding to the terms.

[0096] Organic electroluminescent elements

[0097] The organic electroluminescent element of the present invention uses a previously disclosed structure, comprising an anode, a cathode, and an organic layer located between the anode and the cathode, the organic layer comprising a light-emitting layer.

[0098] The organic layer also includes, but is not limited to, one or more of the following: hole injection layer, hole transport layer, electron blocking layer, hole blocking layer, electron transport layer, and electron injection layer.

[0099] The light-emitting element of the present invention can be fluorescent, phosphorescent, or a combination thereof. The light-emitting element can be a single light-emitting element or a series connection of multiple light-emitting units.

[0100] The following are examples of simple light-emitting elements, but are not limited to them.

[0101] (1) Hole transport layer / fluorescent layer / electron transport layer;

[0102] (2) Hole transport layer / phosphorescent emissive layer / electron transport layer;

[0103] (3) Hole transport layer / first fluorescent luminescent layer / second fluorescent luminescent layer / electron transport layer;

[0104] (4) Hole transport layer / first phosphorescent layer / second phosphorescent layer / electron transport layer;

[0105] (5) Hole transport layer / fluorescent layer / spacer layer / phosphorescent layer / electron transport layer;

[0106] (6) Hole transport layer / electron blocking layer / fluorescent layer / electron transport layer;

[0107] (7) Hole transport layer / electron blocking layer / fluorescent layer / hole blocking layer / electron transport layer;

[0108] (8) Hole transport layer / electron blocking layer / phosphorescent layer / electron transport layer;

[0109] (9) Hole transport layer / electron blocking layer / phosphorescent layer / hole blocking layer / electron transport layer;

[0110] (10) Hole injection layer / hole transport layer / phosphorescent layer / electron transport layer / electron injection layer;

[0111] (11) Hole injection layer / hole transport layer / fluorescent layer / electron transport layer / electron injection layer;

[0112] (12) Hole injection layer / hole transport layer / electron blocking layer / phosphorescent layer / electron transport layer / electron injection layer;

[0113] (13) Hole injection layer / hole transport layer / electron blocking layer / fluorescent layer / electron transport layer / electron injection layer;

[0114] Each of the aforementioned phosphorescent / fluorescent emitting layers can emit light in a different color.

[0115] As a series-connected organic electroluminescent element, it can be an anode / first light-emitting unit / intermediate layer / second light-emitting unit / cathode. The intermediate layer can also be called a charge generation layer, electron extraction layer, or connecting layer. For example, when stacking fluorescent and phosphorescent light-emitting layers, an intermediate layer is placed between the fluorescent and phosphorescent light-emitting layers to prevent excitons generated by the phosphorescent light-emitting layer from diffusing to the fluorescent light-emitting layer, or to adjust the balance of charge carriers.

[0116] When an organic light-emitting device comprises multiple layers of organic materials, the organic material layers can be formed from the same material or different materials.

[0117] The organic electroluminescent element described in this specification can be manufactured using materials and methods known in the art, except that one or more layers of organic material are made by using compounds comprising the present invention.

[0118] As anode materials, materials with relatively large work functions can be used, and transparent conductive oxides, metals, conductive polymers, etc., can be used. Specific examples of anode materials include: metals, such as vanadium, chromium, copper, zinc, and gold, or their alloys; 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; conductive polymers, such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), polypyrrole, and polyaniline, etc., but not limited to these.

[0119] As cathode materials, materials with low work functions are typically used to facilitate electron injection into the organic layer. Metals, metal oxides, conductive polymers, etc., can be used. Specific examples of cathode materials include: metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof; multilayer structure materials such as LiF / Al or LiO2 / Al, but not limited to these.

[0120] The hole injection layer is a layer that injects holes from the electrodes and has the ability to transport holes. To reduce the energy level difference between electrodes, the hole injection layer is mainly prepared based on aromatic amine compounds. It can also be prepared using materials such as copper phthalocyanine in metal complexes and HATCN (2,3,6,7,10,11-hexacyano-1,4,5,8,9,12-hexaazatriphenylene) with a phenylene structure in the lowest unoccupied molecular orbital energy level. When used as a light-emitting host and dopant, an F4-TCNQ (22,3,5,6-tetrafluoro-7,7',8,8'-tetracyanodimethyl-p-benzoquinone) inducer with the lowest unoccupied molecular orbital energy level can be doped into the aromatic amine compound.

[0121] The hole transport layer is a layer that receives holes from the hole injection layer and transports the holes to the light-emitting layer. The hole transport material is a material with high hole mobility that can receive holes from the anode or hole injection layer and transfer the holes to the light-emitting layer. Arylamine derivatives, triphenyldiamine derivatives, etc., can be used, and low molecular weight or high molecular weight materials can also be used.

[0122] Electron blocking layers can adjust the energy difference between the hole transport region and the light-emitting layer, which facilitates the entry of holes into the light-emitting layer and reduces the probability of electrons entering the hole transport region from the light-emitting layer. Aromatic amine derivatives are commonly used.

[0123] A luminescent material is a material that can receive holes and electrons from the hole transport layer and electron transport layer, respectively, and combine the holes and electrons to emit light in the visible light region. The luminescent layer material comprises a host material and dopant materials. Red, green, or blue luminescent materials can be used, and two or more luminescent materials can be mixed as needed. Fluorescent materials or phosphorescent materials can be used as luminescent materials. Single-component materials or multi-component materials can be used as luminescent materials.

[0124] The electron transport layer is a layer that receives electrons from the electron injection layer and transports them to the light-emitting layer. The electron transport material is a material with high electron mobility that can receive electrons from the cathode and transfer them to the light-emitting layer. Metal complexes of triazine derivatives, oxadiazole derivatives, benzoquinone and its derivatives, naphthoquinone and its derivatives, anthraquinone and its derivatives, fluorenone derivatives, diphenyl dicyanoethylene and its derivatives, 8-hydroxyquinoline and its derivatives, etc. can also be used, as well as polymeric materials and small molecule materials.

[0125] An electron injection layer is a layer into which electrons from the electrodes are injected.

[0126] Depending on the materials used, the organic light-emitting device described in this specification can be a top-emitting device, a bottom-emitting device, or a dual-emitting device.

[0127] The charge generation layer is the intermediate layer located between the anode and cathode in a series-connected device, and it is the layer that generates holes and electrons by utilizing charge separation. The charge generation layer is usually formed by a P-type layer on the cathode side and an N-type layer on the anode side, which can effectively separate charges and efficiently transport charge carriers.

[0128] In one embodiment of the present invention, the method for forming each layer is not particularly limited. Conventionally known forming methods based on vacuum evaporation, spin coating, etc., can be used. Each layer, such as the light-emitting layer, can be formed by known methods such as vacuum evaporation, molecular beam evaporation (MBE), or coating methods based on solutions dissolved in solvents, such as immersion coating, spin coating, casting, rod coating, and roll coating.

[0129] In one embodiment of the present invention, the film thickness of each layer is not particularly limited, and can generally be from a few nanometers to several hundred nanometers.

[0130] Those skilled in the art can synthesize the compounds of the present invention by referring to the following synthesis methods and known synthetic methods. There are various synthetic methods for the compounds of the present invention; the following methods are merely illustrative examples.

[0131] LC-MS Brand: Waters, Model: SQ Detector 2

[0132] MRI brand: Bruker, model: AVANCE NEO 400

[0133] Those skilled in the art can synthesize the compounds of the present invention by referring to the following compounds and known synthetic methods. An exemplary synthetic formula of the present invention is as follows:

[0134] Each R is independently selected from halogens (fluorine, chlorine, bromine, iodine), and multiple Rs may be the same or different. The definitions of the remaining groups are the same as in structural formula (1).

[0135] Synthesis Example 1: Synthesis of Compound X3-241

[0136] (1) Synthesis of intermediate X3-241-1

[0137] Under a nitrogen atmosphere, 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. The mixture was then heated at 150 °C and stirred for 12 hours. After the reaction was complete, 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 to remove the solvent. Purification was performed by silica gel chromatography (developing solvent: n-hexane: EA = 100:1 v / v) to give a pale yellow intermediate X3-241-1 (29 g, 85%).

[0138] LC-MS (APCI): 372.21 (M+H) + ).Calcd for C 22 H 11 BrN

[0139] (2) Synthesis of intermediate X3-241-2

[0140] Under a nitrogen atmosphere, 10 g (26.8 mmol) of intermediate X3-241-1, 5.8 g (18.2 mmol) of 4-chloro-1-naphthoic acid, 5.0 g (36.4 mmol) of potassium carbonate, 70 ml of toluene, 30 ml of ethanol, 30 ml of water, and 0.63 g (0.55 mmol) of tetrakis(triphenylphosphine) palladium were added to a four-necked reaction flask. The mixture was heated to 85 °C and reacted. After the reaction was complete, 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 to remove the solvent. The solution was purified by silica gel chromatography (developing solvent: n-hexane:DCM = 20:1 v / v) to obtain a white intermediate X3-241-2 (10.8 g, 88%).

[0141] LC-MS (APCI): 454.34 (M+H) + ).Calcd for C 32 H 20 ClN

[0142] Under a nitrogen atmosphere, 6 g (13.2 mmol) of intermediate X3-241-2, 4.5 g (13.9 mmol) of di(4-biphenyl)amine, 0.24 g (0.26 mmol) of Pd2dba3, 0.22 g (0.52 mmol) of Sphos, and 2.5 g (26.4 mmol) of sodium tert-butoxide were added to a four-necked reaction flask, followed by 50 mL of toluene. The mixture was heated to 110 °C and reacted. After the reaction was complete, the reaction solution was cooled to room temperature and extracted with dichloromethane. The organic phase was dried over anhydrous sodium sulfate to remove the solvent. Purification was performed by silica gel chromatography (developing solvent: n-hexane:DCM = 3:1, v / v). Compound X3-241 (9.2 g, 94%) was obtained as a white solid.

[0143] LC-MS (APCI): 739.57 (M+H) + ).Calcd for C 56 H 38 N2

[0144] 1 H NMR(400MHz,Methylene Chloride-d2)δ8.61(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).

[0145] Synthesis Example 2: Synthesis of Compound X3-27

[0146] Under a nitrogen atmosphere, 4-(naphthyl-1-yl)-N-phenylaniline (5.47 g, 18.54 mmol), intermediate X3-241-2 (8.0 g, 17.66 mmol), 2-dicyclohexylphosphine-2′,6′-dimethoxy-biphenyl (776 mg, 1.84 mmol), tris(dibenzylacetone)dipalladium (810 mg, 0.92 mmol), and sodium tert-butoxide (3.4 g, 35.32 mmol) were added to a four-necked reaction flask, followed by 200 mL of toluene. The mixture was heated to reflux and reacted for 4 hours. After the reaction was complete, the mixture was filtered, the filter cake was washed with water, and then refluxed with 100 mL of ethyl acetate for 30 minutes before filtration to obtain 10.3 g of compound X3-27 (yield 82%).

[0147] LC-MS(APCI): 713.57(M+H+).Calcd for C54H36N2

[0148] 1H NMR(400MHz,DMSO-d6)δ8.53(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).

[0149] Synthesis Example 3: Synthesis of Compound X3-29

[0150] Under a nitrogen atmosphere, intermediate X3-241-2 (7.0 g, 15.4 mmol), 4-(naphthyl-2-yl)-N-phenylaniline (4.6 g, 15.4 mmol), sodium tert-butoxide (3.0 g, 30.8 mmol), 2-dicyclohexylphosphine-2′,6′-dimethoxy-biphenyl (633 mg, 1.5 mmol), and tris(dibenzylacetone)dipalladium (705 mg, 0.8 mmol) were added to a four-necked reaction flask, followed by 100 mL of toluene. The mixture was heated to 110 °C and reacted for 2 h. After purification by column chromatography, the mixture was slurried with n-hexane:dichloromethane at a volume ratio of 1:1 to obtain 5.9 g of compound X3-29 as a white solid, with a yield of 54%.

[0151] LC-MS(APCI): 713.57(M+H+).Calcd for:C54H36N2

[0152] 1H NMR(400MHz,Methylene Chloride-d2)δ8.41(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),7.5 5–7.39(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).

[0153] Synthesis Example 4: Synthesis of Compound X5-241

[0154] (1) Synthesis of intermediate X5-2

[0155] Under a nitrogen atmosphere, X5-1 (12.00 g, 32.34 mmol), 4-chloro-1-naphthoboric acid (6.66 g, 32.34 mmol), potassium carbonate (8.94 g, 64.68 mmol), and palladium dichloride (0.45 g, 0.65 mmol) were placed in a four-necked reaction flask, along with 90 mL of THF and 30 mL of H2O. The mixture was heated to 70 °C and reacted for 2 h. After the reaction was complete, the temperature of the reaction solution was lowered to 25 °C, and 200 mL of water was added. The reaction solution was extracted with ethyl acetate, separated, and the organic phase was evaporated to dryness. The organic phase was then dried over anhydrous sodium sulfate. The crude product was purified by silica gel chromatography (developing solvent: n-hexane: dichloromethane = 10:1, v / v) to give a white solid intermediate X5-2 (10.5 g, yield 72%).

[0156] (2) Synthesis of compound X5-241

[0157] Under a nitrogen atmosphere, intermediate X5-2 (6 g, 13.2 mmol), di(4-biphenyl)amine (4.5 g, 13.9 mmol), tris(dibenzylacetone)palladium (0.24 g, 0.26 mmol), 2-dicyclohexylphosphine-2',6'-dimethoxybiphenyl (0.22 g, 0.52 mmol), sodium tert-butoxide (2.54 g, 26.4 mmol), and 50 mL of toluene were added to a reaction flask, and the mixture was heated to 110 °C and reacted for 5 hours. After the reaction was complete, the reaction solution was cooled to room temperature, and 150 mL of water was added. The reaction solution was extracted with dichloromethane and separated. The organic phase was dried over anhydrous sodium sulfate and then evaporated to dryness to obtain the crude product. The crude product was purified by silica gel chromatography (developing solvent: n-hexane:dichloromethane = 4:1, v / v) to obtain compound X5-241 (7.9 g, yield 81%) as a white solid.

[0158] LC-MS (APCI): 739.44 [M+H] + .Calcd for:C 56 H 38 N2,738.30

[0159] 1H NMR(400MHz,Methylene Chloride-d2)δ8.69(s,1H),8.34(dt,J=7.7,1.0Hz,1H),8.24–8.19(m,1H),8.14(ddd,J=16.4,8.5,1.3Hz,2H),7.97–7.91(m,3H),7.90–7.82(m,2H) ),7.76(dt,J=7.4,1.6Hz,1H),7.66(d,J=7.5Hz,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).

[0160] Synthesis Example 5: Synthesis of Compound X3-163

[0161] Under a nitrogen atmosphere, intermediate X3-241-2 (6 g, 13.2 mmol), N-(3-biphenyl)-N-(4-biphenyl)amine (4.5 g, 13.9 mmol), tris(dibenzylacetone)palladium (0.24 g, 0.26 mmol), 2-bicyclohexylphosphine-2',6'-dimethoxybiphenyl (0.22 g, 0.52 mmol), sodium tert-butoxide (2.54 g, 26.4 mmol), and 50 mL of toluene were added to a reaction flask, and the mixture was heated to 110 °C and reacted for 4 hours. After the reaction was complete, the reaction solution was cooled to room temperature, 100 mL of water was added, and the reaction solution was extracted with dichloromethane and separated. The organic phase was dried over anhydrous sodium sulfate and then evaporated to dryness to obtain the crude product. The crude product was purified by silica gel chromatography (developing solvent: n-hexane: dichloromethane = volume ratio 3:1) to obtain compound X3-163 (8.8 g, yield 90%) as a white solid.

[0162] LC-MS (APCI): 739.41 [M+H] + .Calcd for:C 56 H 38 N2 738.30.

[0163] 1H NMR(400MHz,Methylene Chloride-d2)δ8.77–8.68(m,1H),8.55–8.50(m,1H),8.38(d,J=8.0Hz,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=9.5,7.2,2.0Hz,1 H),7.20–7.08(m,5H),6.91(dd,J=7.6,4.7Hz,1H),6.77(d,J=7.7Hz,1H).

[0164] Synthesis Example 6: Synthesis of Compound X3-4

[0165] Under a nitrogen atmosphere, intermediate X3-241-2 (6.6 g, 14.5 mmol), N-phenyl-4-benzidine (3.7 g, 15.3 mmol), tris(dibenzylacetone)palladium (0.26 g, 0.29 mmol), 2-dicyclohexylphosphine-2',6'-dimethoxybiphenyl (0.24 g, 0.57 mmol), sodium tert-butoxide (2.8 g, 29 mmol), and 70 mL of toluene were added to a reaction flask, and the mixture was heated to 110 °C and reacted for 4 hours. After the reaction was complete, the reaction solution was cooled to room temperature, and 150 mL of water was added to the reaction solution. The reaction solution was extracted with dichloromethane, separated, and the organic phase was dried over anhydrous sodium sulfate. The organic phase was then evaporated to dryness to obtain the crude product. The crude product was purified by silica gel chromatography (developing solvent: n-hexane: dichloromethane = volume ratio 4:1) to obtain compound X3-4 as a white solid (7.2 g, yield 72%).

[0166] LC-MS (APCI): 663.47 [M+H] + Calculated for:C 50 H 34 N2 662.27.

[0167] 1 H NMR(400MHz,Methylene Chloride-d2)δ8.72(ddd,J=10.4,8.4,1.0Hz,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).

[0168] Synthesis Example 7: Synthesis of Compound X3-10

[0169] Under a 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(dibenzylacetone)palladium (0.24 g, 0.26 mmol), 2-bicyclohexylphosphine-2',6'-dimethoxybiphenyl (0.22 g, 0.52 mmol), sodium tert-butoxide (2.54 g, 26.4 mmol), 5 0 ml of toluene was added to the reaction flask, and the mixture was heated to 110 °C and reacted for 4 hours. After the reaction was complete, the reaction solution was cooled to room temperature, and 150 ml of water was added. The reaction solution was extracted with dichloromethane and separated. The organic phase was dried over anhydrous sodium sulfate and then evaporated to dryness to obtain the crude product. The crude product was purified by silica gel chromatography (developing solvent: n-hexane:dichloromethane = v / v 4:1) to obtain compound X3-10 (7.6 g, yield 78%) as a white solid.

[0170] LC-MS (APCI): 739.39 [M+H] + .Calcd for:C 56 H 38 For the mass spectrum corresponding to N2 738.30, please refer to Appendix 2 in the instruction manual.

[0171] 1 ¹H NMR (400MHz, DMSO-d⁶) δ 8.69 (dd, J=16.3, 8.4Hz, 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 NMR spectra are shown in Figure 3 of the specification.

[0172] Synthesis Example 8: Synthesis of Compound X3-186

[0173] Under a nitrogen atmosphere, 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(dibenzylacetone)dipalladium (0.24 g, 0.26 mmol), 2-bicyclohexylphosphine-2',6'-dimethoxybiphenyl (0.22 g, 0.52 mmol), sodium tert-butoxide (2.54 g, 26.4 mmol), and 50 mL of toluene were added to a reaction flask, and the mixture was heated to 110 °C and reacted for 4 hours. After the reaction was complete, the reaction solution was cooled to room temperature, and 150 mL of water was added. The reaction solution was extracted with dichloromethane, separated, and the organic phase was dried over anhydrous sodium sulfate. The organic phase was then evaporated to dryness to obtain the 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.

[0174] LC-MS (APCI): 789.47 [M+H] + Calculated for:C 60 H 40 N2 788.32.

[0175] 1 H NMR(400MHz,Methylene Chloride-d2)δ8.67(dd,J=8.4,5.5Hz,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).

[0176] Synthesis Example 9: Synthesis of Compound X3-17

[0177] Under a 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-bicyclohexylphosphine-2',6'-dimethoxybiphenyl (0.22 g, 0.52 mmol), sodium tert-butoxide (2.54 g, 26.4 mmol), 5 0 ml of toluene was added to the reaction flask, and the mixture was heated to 110 °C and reacted for 5 hours. After the reaction was complete, the reaction solution was cooled to room temperature, and 150 ml of water was added. The reaction solution was extracted with dichloromethane and separated. The organic phase was dried over anhydrous sodium sulfate and then evaporated to dryness to obtain the crude product. The crude product was purified by silica gel chromatography (developing solvent: n-hexane:dichloromethane = 3:1, v / v) to obtain compound X3-17 (8.3 g, yield 85%) as a white solid.

[0178] LC-MS (APCI): 739.46 [M+H] + .Calcd for:C 56 H 38 For the mass spectrum corresponding to N2 738.30, please refer to Appendix 4 in the instruction manual.

[0179] 1 ¹H NMR (400MHz, Methylene Chloride-d²) δ 8.74 (dd, J = 11.3, 8.4Hz, 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 = 7.7Hz, 2H), 6.81–6.29 (m, 4H). The corresponding NMR spectra are shown in Figure 5 of the specification.

[0180] Synthesis Example 10: Synthesis of Compound X3-264

[0181] Under a nitrogen atmosphere, intermediate X3-241-2 (6 g, 13.2 mmol), N-(4-(-1-naphthyl)phenyl)-4-benzidine (5.2 g, 13.9 mmol), tris(dibenzylacetone)palladium (0.24 g, 0.26 mmol), 2-dicyclohexylphosphine-2',6'-dimethoxybiphenyl (0.22 g, 0.52 mmol), sodium tert-butoxide (2.54 g, 26.4 mmol), and 60 mL of toluene were added to a reaction flask, and the mixture was heated to 110 °C and reacted for 4 hours. After the reaction was complete, the reaction solution was cooled to room temperature, and 200 mL of water was added. The reaction solution was extracted with dichloromethane, separated, and the organic phase was dried over anhydrous sodium sulfate. The organic phase was then evaporated to dryness to obtain the 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.

[0182] LC-MS (APCI): 789.48 [M+H] + .Calcd for:C 60 H 40 For the mass spectrum corresponding to N2 788.32, please refer to Appendix 6 in the instruction manual.

[0183] 1 H NMR (400MHz, DMSO-d6) δ8.69 (dd, J=15.6, 8.4Hz, 1H), 8.49 (dd, J=52.0, 7.7Hz, 1H), 8.07–7.80 (m, 9H), 7.74–7. 64(m,1H),7.61–7.27(m,17H),7.09(dddd,J=57.3,28.9,14.7,7.1Hz,7H),6.84(d,J=7.6Hz,1H),6.63(s,3H).

[0184] Synthesis Example 11: Synthesis of Compound X3-1891

[0185] Under a 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(dibenzylacetone)palladium (0.24 g, 0.26 mmol), 2-bicyclohexylphosphine-2',6'-dimethoxybiphenyl (0.22 g, 0.52 mmol), sodium tert-butoxide (2.54 g, 26.4 mmol), and 60 mL of toluene were added to a reaction flask, and the mixture was heated to 110 °C and reacted for 4 hours. After the reaction was complete, the reaction solution was cooled to room temperature, 200 mL of water was added, and the reaction solution was extracted with dichloromethane and separated. The organic phase was dried over anhydrous sodium sulfate and then evaporated to dryness to obtain the 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.

[0186] LC-MS (APCI): 839.49 [M+H] + .Calcd for:C 64 H 42 N2,838.33.

[0187] 1 H NMR(400MHz,Methylene Chloride-d2)δ8.77(ddd,J=18.4,8.5,1.1Hz,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).

[0188] Synthesis Example 12: Synthesis of Compound X3-254

[0189] Under a nitrogen atmosphere, 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(dibenzylacetone)dipalladium (0.24 g, 0.26 mmol), 2-bicyclohexylphosphine-2',6'-dimethoxybiphenyl (0.22 g, 0.52 mmol), sodium tert-butoxide (2.54 g, 26.4 mmol), and 60 mL of toluene were added to a reaction flask, and the mixture was heated to 110 °C and reacted for 5 hours. After the reaction was complete, the reaction solution was cooled to room temperature, 200 mL of water was added, and the reaction solution was extracted with dichloromethane and separated. The organic phase was dried over anhydrous sodium sulfate and then evaporated to dryness to obtain the crude product. The crude product was purified by silica gel chromatography (developing solvent: n-hexane: dichloromethane = volume ratio 3:1) to obtain compound X3-254 (9.1 g, yield 85%) as a white solid.

[0190] LC-MS (APCI): 815.51 [M+H] + Calculated for:C 62 H 42 N2 814.33.

[0191] 1 H NMR(400MHz,Methylene Chloride-d2)δ8.62(dd,J=16.5,8.3Hz,1H),8.42(dd,J=7.3,1.4Hz,1H),8.29(d,J=8.0Hz,1H),7.98(d,J=8.5Hz,1H),7.90(dd,J=8.2,1.3Hz,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=7.6Hz,1H),6.76(d,J=7.6Hz,1H),6.61(d,J=7.7Hz,1H).

[0192] Synthesis Example 13: Synthesis of Compound X1-241

[0193] Under a nitrogen atmosphere, intermediate X-1-1 (6 g, 13.2 mmol), di(4-biphenyl)amine (4.5 g, 13.9 mmol), tris(dibenzylacetone)palladium (0.24 g, 0.26 mmol), 2-dicyclohexylphosphine-2',6'-dimethoxybiphenyl (0.22 g, 0.52 mmol), sodium tert-butoxide (2.54 g, 26.4 mmol), and 50 mL of toluene were added to a reaction flask, and the mixture was heated to 110 °C and reacted for 3 hours. After the reaction was complete, the reaction solution was cooled to room temperature, and 100 mL of water was added. The reaction solution was extracted with dichloromethane, separated, and the organic phase was dried over anhydrous sodium sulfate. The organic phase was then evaporated to dryness to obtain the crude product. The crude product was purified by silica gel chromatography (developing solvent: n-hexane:dichloromethane = 4:1 v / v) to obtain compound X1-241 (7.3 g, yield 75%) as a white solid.

[0194] LC-MS (APCI): 739.40 [M+H] + .Calcd for:C 56 H 38 N2.

[0195] 1 H NMR(400MHz,Methylene Chloride-d2)δ8.59(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).

[0196] The following application examples further illustrate the organic electroluminescent element described in this invention.

[0197] Application Example 1:

[0198] This embodiment provides an organic electroluminescent element, as shown in FIG1, comprising 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 stacked from bottom to top.

[0199] The specific device structure is as follows:

[0200] ITO / HT1-PD3%(10nm) / HT1(60nm) / HT2(5nm) / BH-BD3%(20nm) / HB(5nm) / ET-LiQ50%(30nm) / Mg:Ag 1:9(100nm)

[0201] Device fabrication process:

[0202] The bottom-emitting glass substrate 1 used in this embodiment was purchased from Guangdong Xinli Display Technology Co., Ltd., and ITO was used as the anode 2. First, the bottom-emitting glass substrate was cleaned sequentially with ITO cleaning agent, deionized water, and isopropanol. Then, the bottom-emitting glass substrate was baked at 180 degrees Celsius for 30 minutes to dry it.

[0203] Then, the bottom-emitting glass substrate is placed in the evaporation chamber, under a vacuum of approximately 10... -8 Under the condition of Turbo evaporation, organic layers were sequentially deposited on the ITO anode by thermal vacuum evaporation at a rate of 0.2-2 Å / s. Specifically, 3% PD was doped onto HT1 to form a 10 nm thick hole injection layer 3; HT1 was formed to a 60 nm thick hole transport layer 4; HT2 was deposited onto HT1 to a 5 nm thick electron blocking layer 5; 3% BD was doped onto the anthracene substrate BH to form a 20 nm thick blue emitting layer 6; HB was formed to a 5 nm thick hole blocking layer 7; ET was doped with 50% LiQ to form a 30 nm thick electron transport layer 8; and Mg:Ag (1:9) was formed to a 100 nm thick cathode 9. Finally, the device was transferred back to the glove box and encapsulated with a glass cover and desiccant to complete the device, denoted as Organic Electronic Component 1. In this embodiment of the device, the same layer is deposited using different materials in a specific volume ratio, such as 50% LiQ (ET 50% and LiQ 50% by volume). The materials used to prepare the device in this invention are purified by sublimation, achieving a purity of over 99.9%.

[0204] The synthesis method of HT2 is the same as that of X3-241, except that di(4-biphenyl)amine is replaced by CAS: 1592944-27-8, and X3-241-2 is replaced by CAS: 1464824-91-6 (LC-MS (APCI): 739.51 (M+H+)). The vapor deposition temperature of HT2 is 420℃.

[0205] Examples and Comparative Examples

[0206] The electron blocking layer was prepared using compound X3-241, which was synthesized in Example 1 of this invention, instead of HT2. Organic electronic component 2 was then fabricated using the same method. The deposition temperature of X3-241 was 353°C.

[0207] In this invention, compound HT-3 is used instead of HT2 to prepare the electron blocking layer, and organic electronic components 5 are fabricated using the same method. The vapor deposition temperature of HT-3 is 345℃.

[0208] In this invention, compound HT-4 is used instead of HT2 to prepare the electron blocking layer, and organic electronic components 6 are fabricated using the same method. The vapor deposition temperature of HT-4 is 419°C.

[0209] In this invention, compound HT-5 is used instead of HT2 to prepare the electron blocking layer, and organic electronic components 7 are fabricated using the same method. The vapor deposition temperature of HT-5 is 397°C.

[0210] In this invention, compound HT-6 is used instead of HT2 to prepare the electron blocking layer, and organic electronic component 8 is fabricated using the same method. The vapor deposition temperature of HT-6 is 403°C. Compound X3-27, obtained in Synthesis Example 2 of this invention, is used instead of HT2 to prepare the electron blocking layer, and organic electronic component 3 is fabricated using the same method. The vapor deposition temperature of X3-27 is 336°C.

[0211] The electron blocking layer was prepared using compound X3-29, obtained in Example 3 of this invention, instead of HT2, and organic electronic component 4 was fabricated using the same method. The deposition temperature of X3-29 was 347°C.

[0212] The electron blocking layer was prepared using compound X5-241, obtained in Example 4 of this invention, instead of HT2, and organic electronic components 9 were fabricated using the same method. The deposition temperature of X5-241 was 389°C.

[0213] The electron blocking layer was prepared by using compound X3-163, obtained in Synthesis Example 5 of this invention, instead of HT2, and organic electronic component 10 was fabricated using the same method. The deposition temperature of X3-163 was 348°C.

[0214] The electron blocking layer was prepared by using compound X3-4, obtained in Example 6 of this invention, instead of HT2, and organic electronic component 11 was fabricated using the same method. The deposition temperature of X3-4 was 320°C.

[0215] The electron blocking layer was prepared by replacing HT2 with compound X3-10 obtained in Example 7 of this invention, and organic electronic component 12 was fabricated using the same method. The deposition temperature of X3-10 was 352°C.

[0216] The electron blocking layer was prepared by using compound X3-186, obtained in Example 8 of this invention, instead of HT2, and organic electronic component 13 was fabricated using the same method. The deposition temperature of X3-186 was 350°C.

[0217] The electron blocking layer was prepared by using compound X3-17, obtained in Example 9 of this invention, instead of HT2, and organic electronic components 14 were fabricated using the same method. The X3-17 was deposited at a temperature of 355°C.

[0218] The electron blocking layer was prepared using compound X3-264, obtained in Synthesis Example 10 of this invention, instead of HT2, and organic electronic components 15 were fabricated using the same method. The deposition temperature of X3-264 was 355°C.

[0219] The electron blocking layer was prepared using compound X3-1891, obtained in Synthesis Example 11 of this invention, instead of HT2, and organic electronic components 16 were fabricated using the same method. The deposition temperature of X3-1891 was 391°C.

[0220] The electron blocking layer was prepared using compound X3-254, obtained in Synthesis Example 12 of this invention, instead of HT2, and organic electronic components 17 were fabricated using the same method. The deposition temperature of X3-254 was 361°C.

[0221] The electron blocking layer was prepared using compound X1-241, obtained in Synthesis Example 13 of this invention, instead of HT2, and organic electronic components 18 were fabricated using the same method. The deposition temperature of X1-241 was 391°C.

[0222] Evaluation of organic electroluminescent devices

[0223] Drive voltage at current density of 15mA / cm 2 Next test.

[0224] Lifetime testing method: A voltage is applied to the obtained organic electroluminescent device to achieve a current density of 60 mA / cm². 2 The time it takes for the brightness to become 95% of the initial brightness is measured (LT95 (unit: hours)).

[0225] The organic electroluminescent elements 2-4 and 9-18 and organic electronic elements 1 and 5-8 prepared by the compounds of this application have lower driving voltages and longer lifespans. Therefore, the compounds of this invention are suitable for preparing high-performance organic electroluminescent elements. Compounds X3-241, X3-27, X3-29, X5-241, X3-163, X3-4, X3-10, X3-186, X3-17, X3-264, X3-1891, and X3-254 have significantly lower vapor deposition temperatures than HT2, HT-3, HT-4, HT-5, HT-6, and HT-7, and can withstand longer heating times, which is beneficial for industrial use.

[0226] Those skilled in the art will readily understand that the above description is merely a preferred embodiment of the present invention and is not intended to limit the present invention. Any modifications, equivalent substitutions, and improvements made within the spirit and principles of the present invention should be included within the scope of protection of the present invention.

Claims

1. An organic electroluminescent element, comprising an anode, a cathode, and a light-emitting layer located 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 is independently selected from single-bonded, substituted or unsubstituted C6-C30 arylene groups, or substituted or unsubstituted C3-C30 N-free heteroarylene groups. Ar 1 Ar 2 Each is independently selected from hydrogen, substituted or unsubstituted C6-C30 aryl groups, or substituted or unsubstituted C3-C30 non-N heteroaryl groups. The substituents in the substituted or unsubstituted form do not contain N.

2. The organic electroluminescent element according to claim 1, characterized in that... Equation (1) is selected from equations (2), (3) or (4). L 1 L 2 Ar 1 Ar 2 The definition is the same as in claim 1.

3. The organic electroluminescent element according to claim 1, characterized in that... Equation (1) is selected from equations (2-1), (2-2), (2-3), (3-1), (3-2), (3-3), (4-1), (4-2), and (4-3). L 1 L 2 Ar 1 Ar 2 The definition is the same as in claim 1.

4. The organic electroluminescent element according to claim 1, characterized in that... Equation (1) is selected from equations (2-2) and (2-3). L 1 L 2 Ar 1 Ar 2 Define the same as equation (1); Preferably, formula (1) is selected from formula (2-3). L 1 L 2 Ar 1 Ar 2 Define the same as equation (1).

5. The organic electroluminescent element according to any one of claims 1-4, characterized in that... L 1 L 2 Each is independently selected from single bonds, substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted anthracene, substituted or unsubstituted phenanthylene, substituted or unsubstituted biphenylene, substituted or unsubstituted terphenylene, substituted or unsubstituted phenylnaphthylene, substituted or unsubstituted dibenzofuranylene, substituted or unsubstituted dibenzothiopheneylene, substituted or unsubstituted 9,9'-dimethylfluoreneylene, substituted or unsubstituted 9,9'-diphenylfluoreneylene, substituted or unsubstituted spirodifluoreneylene.

6. The organic electroluminescent element according to any one of claims 1-4, characterized in that... Ar 1 Ar 2 Each of the following is independently selected from hydrogen, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthraquinone, substituted or unsubstituted phenanthrene, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted phenylnaphthyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted 9,9'-dimethylfluorenyl, substituted or unsubstituted 9,9'-diphenylfluorenyl, and substituted or unsubstituted spirodifluorenyl.

7. The organic electroluminescent element according to any one of claims 1-4, characterized in that... The L 1 L 2 Each of the following groups, independently selected from single bonds, substituted or unsubstituted groups: dotted line It represents replacing a position.

8. The organic electroluminescent element according to any one of claims 1-4, characterized in that... The Ar 1 Ar 2 Each of the following groups, independently selected from hydrogen, substituted or unsubstituted, is selected: dotted line It represents replacing a position.

9. The organic electroluminescent element according to any one of claims 1-4, characterized in that... -L 1 -Ar 1 -L 2 -Ar 2 Each is independently selected from hydrogen, or one of Y1 to Y81. dotted line It represents replacing a position.

10. The compound according to claim 1, characterized in that, The compound is selected from the structure shown below.

11. The first organic layer according to any one of claims 1-10 is a light-emitting auxiliary layer, an electron blocking layer, a hole transport layer, a charge generation layer, or a hole injection layer.

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

13. The organic electroluminescent element according to claims 1-10 is a single-layer element or a multilayer element.

14. An electronic device comprising the organic electroluminescent element as described in claims 1-13.

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