Organic electroluminescent material and organic electroluminescent element comprising same

Abstract

The invention belongs to the technical field of photoelectric materials, and provides an organic electroluminescent material and an organic electroluminescent element containing the same. An organic electroluminescent material having a structure represented by formula (1) # imgabs0 # # imgabs1 # represents a double bond or a single bond, X1 is selected from O, S, N, and NR, X2 is selected from O, S, N, and NR, R is selected from hydrogen, a substituted or unsubstituted C6-C60 aryl group, and a substituted or unsubstituted C3-C60 heteroaryl group, and L1-L4 are independently selected from a linking bond, a substituted or unsubstituted C6-C60 arylene group, and a substituted or unsubstituted C3-C60 heteroaryl group. The organic electroluminescent element prepared by using the material can realize reduced driving voltage and durable service life. The organic electroluminescent element has better performance.

Description

Technical Field

[0001] The invention belongs to the technical field of organic electroluminescence, and in particular relates to an organic electroluminescent material and an organic electroluminescent element containing the same. Background Art

[0002] An organic light emitting diode (OLED) is a self-luminous display element based on organic electroluminescent materials. Unlike existing liquid crystal display elements, it does not require a backlight source and is thin, making it a technology suitable for flexible element devices (flexible light-emitting display devices).

[0003] The organic light-emitting device has an anode and a cathode, and a structure in which an organic thin film is placed between the two electrodes. It can be a simple element including a single light-emitting unit or a tandem element including multiple light-emitting units.

[0004] Simple components usually include a hole transport layer, a light-emitting layer, and an electron transport layer. Since the electron mobility of the electron transport layer material is much lower than the hole mobility of the hole transport layer material, the holes and electrons entering the light-emitting layer are unbalanced, affecting the light-emitting efficiency and life of the component.

[0005] A series element usually has a charge generation layer between the light-emitting units to ensure that the charge is effectively distributed to the light-emitting stack while improving the current efficiency in each light-emitting layer. Usually, the charge generation layer has a PN junction in which an N-type charge generation layer and a P-type charge generation layer are stacked in sequence.

[0006] The injection barrier of electrons from the charge generation layer to the adjacent electron transport layer is relatively large. Therefore, electrons accumulate at the interface between the N-type charge generation layer and the adjacent electron transport layer, which can easily cause degradation of the interface and shorten the life of the component.

[0007] Therefore, there is an urgent need to develop new materials to increase the life of components. Summary of the invention

[0008] The object of the present invention is to provide an organic electroluminescent material, and an organic electroluminescent element prepared using the material can achieve a reduced driving voltage and a durable service life.

[0009] The technical solution adopted by the present invention to solve its technical problem is:

[0010] An organic electroluminescent material, the compound having a structure shown in formula (1)

[0011]

[0012] represents a double bond or a single bond,

[0013] X 1 Selected from O, S, N, NR,

[0014] X 2 Selected from O, S, N, NR,

[0015] R is selected from hydrogen, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl, L 1 -L 4 are independently selected from a linking bond, a substituted or unsubstituted C6-C60 arylene group, and a substituted or unsubstituted C3-C60 heteroarylene group,

[0016] R 1 -R 4 each independently selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C2-C10 heterocycloalkyl, substituted or unsubstituted C1-C10 alkoxy, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl,

[0017] The substituent in the substituted or unsubstituted group is selected from one or a combination of halogen, cyano, C1-C10 alkyl, C6-C30 aryl, C3-C30 heteroaryl.

[0018] Preferably, the compound has a structure shown in formula (1-1) or formula (1-2):

[0019]

[0020] Preferably, X 1 is selected from O or S; preferably, X 2 Select from O or S.

[0021] Preferably, the C6-C60 arylene group is selected from the group including but not limited to the following groups: phenylene, naphthylene, biphenylene, phenylene substituted naphthylene, naphthylene substituted naphthylene, anthrylene, phenanthrenyl, fluoranthenyl, triphenylene, perylene, pyrenyl, benzopyrenyl, ... base;

[0022] The C3-C60 heteroarylene group is selected from the group including but not limited to the following groups: dibenzofuranylene, dibenzothienylene, pyridylene;

[0023] The C1-C10 alkyl group is selected from, but not limited to, the following groups: methyl, ethyl, tert-butyl;

[0024] The C3-C10 cycloalkyl group is selected from, but not limited to, the following groups: cyclopropyl, cyclohexyl, cycloadamantyl;

[0025] The C6-C60 aryl group is selected from the group including but not limited to the following groups: phenyl, biphenyl, naphthyl, anthracenyl, phenanthrenyl, fluoranthenyl, triphenylene, peryl, pyrenyl, benzopyrenyl, base;

[0026] The C3-C60 heteroaryl group is selected from the group including, but not limited to, the following groups: dibenzofuranyl, dibenzothienyl, and pyridyl.

[0027] As a preference, L 1 , L 2 , L 3 , L 4 Each independently selected from a single bond, phenylene, biphenylene, phenylene-substituted naphthylene, biphenylene, naphthylene, anthrylene, phenanthrenyl, pyrenyl, perylene, triphenylene, fluoranthenyl, dibenzofuranyl, dibenzothiophenylene,

[0028] The following groups in which one or more hydrogen atoms are replaced by substituents: phenylene, biphenylene, phenylene-substituted naphthylene, biphenylene, naphthylene, anthrylene, phenanthrenyl, pyrenyl, perylene, triphenylene, fluoranthenyl, dibenzofuranyl, dibenzothiophenylene, wherein the substituents are each independently selected from deuterium, halogen, cyano or a combination of several thereof.

[0029] As a preference, R 1 , R 2 , R 3 , R 4 Each is independently selected from hydrogen, halogen, methyl, ethyl, tert-butyl, cyclopropyl, cyclohexyl, cycloadamantyl, phenyl, naphthyl, anthracenyl, phenanthryl, phenyl-substituted anthracenyl, pyrenyl, peryl, triphenylene, fluoranthenyl, dibenzofuranyl, dibenzothienyl, carbazolyl, and the following groups in which one or more hydrogen is replaced by a substituent: methyl, ethyl, tert-butyl, cyclopropyl, cyclohexyl, cycloadamantyl, phenyl, naphthyl, anthracenyl, phenanthryl, phenyl-substituted anthracenyl, pyrenyl, peryl, triphenylene, fluoranthenyl, dibenzofuranyl, dibenzothienyl, carbazolyl, and the substituent is independently selected from one or more of deuterium, halogen, cyano, phenyl, naphthyl, anthracenyl, phenanthryl, phenyl-substituted anthracenyl, pyrenyl, triphenylene, fluoranthenyl, dibenzofuranyl, dibenzothienyl, carbazolyl.

[0030] As a preference, -L 1 R 1 Not hydrogen; -L 1 R 1 Not hydrogen means L 1 is not a single bond, and R 1 Not hydrogen.

[0031] An organic electroluminescent element comprises: a first electrode, a second electrode and an organic material layer arranged between the first electrode and the second electrode, wherein one or more layers of the organic material layer contain the organic electroluminescent material described in the present invention.

[0032] Preferably, the organic material layer comprises an electron transport layer and a hole blocking layer, and at least one of the electron transport layer and the hole blocking layer comprises the compound described in any one of the present invention.

[0033] Preferably, the organic material layer comprises at least two light-emitting units, the light-emitting units comprise electron transport layers, a charge generation layer is comprised between the light-emitting units, the charge generation layer comprises an N-type charge generation layer and a P-type charge generation layer, and the N-type charge generation layer and / or the electron transport layer comprise the organic electroluminescent material described in the present invention.

[0034] The electron transport layer comprises the electron transport layer of each light-emitting unit, and at least one of the N-type charge generation layer and the electron transport layer comprises the organic electroluminescent material of the present invention, which means that one N-type charge generation layer comprises the organic electroluminescent material of the present invention; or multiple N-type charge generation layers comprise the organic electroluminescent material of the present invention; or one electron transport layer in one light-emitting unit comprises the organic electroluminescent material of the present invention; or one N-type charge generation layer and one electron transport layer in one light-emitting unit comprise the organic electroluminescent material of the present invention; or one N-type charge generation layer and each electron transport layer in multiple light-emitting units comprise the organic electroluminescent material of the present invention; or multiple N-type charge generation layers and each electron transport layer in multiple light-emitting units comprise the organic electroluminescent material of the present invention, etc. When more than or equal to 2 layers comprise the organic electroluminescent material of the present invention, the organic electroluminescent materials are the same or different.

[0035] The stacked structure of the present invention refers to n light-emitting units, where n is greater than or equal to 2, and the number of N-type charge generation layers is n-1.

[0036] An electronic device includes one or more of a display, a monitor, and a lighting device, and contains the organic electroluminescent element of the present invention.

[0037] Compared with the prior art, the present invention has the following beneficial effects:

[0038] 1. The organic electroluminescent compound of the present invention has a quinoline benzoxazole structure, which improves the electron injection and transmission capabilities; the organic electroluminescent element prepared using the compound can achieve a reduced driving voltage and a long service life.

[0039] 2. Organic electroluminescent elements have a better lifespan. BRIEF DESCRIPTION OF THE DRAWINGS

[0040] Figure 1 It is a schematic diagram of the structure of the organic electroluminescent element described in Application Example 1, wherein the first electrode layer 1, the hole injection layer 2, the hole transport layer 3, the light-emitting layer 4, the electron transport layer 5, the N-type charge generation layer 6, the P-type charge generation layer 7, the hole transport layer 8, the light-emitting layer 9, the electron transport layer 10, the electron injection layer 11 and the second electrode layer 12, wherein 100 is the first light-emitting unit and 200 is the second light-emitting unit. DETAILED DESCRIPTION

[0041] In order to more fully describe the present invention to those skilled in the art, embodiments of the present invention are provided. The scope of the present invention is not limited to the following embodiments. These embodiments can make the present invention more thorough and complete, and fully convey the viewpoints of the present invention to those skilled in the art.

[0042] Unless otherwise specified, the experimental methods used in the following examples are all conventional methods; the reagents, materials, etc. used in the following examples, unless otherwise specified, can be obtained from commercial channels.

[0043] As used in the present invention, the term "halogen" may include fluorine, chlorine, bromine or iodine.

[0044] As used in the present invention, the term "C1-C10 alkyl" refers to a monovalent substituent derived from a straight or branched chain 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.

[0045] As used in the present invention, the term "C3-C10 cycloalkyl" refers to a monovalent substituent derived from a monocyclic or polycyclic non-aromatic hydrocarbon having 3 to 10 carbon atoms. Examples of such cycloalkyl include, but are not limited to, cyclopropane, cyclobutane, cyclopentane, cyclohexane, norbornyl, adamantane, and the like.

[0046] As used in the present invention, the term "C2-C10 heterocycloalkyl" is a monovalent substituent having a monocyclic or polycyclic ring of 2 to 10 carbon atoms, and the ring contains at least one heteroatom selected from O, S, N, P, and Si.

[0047] As used in the present invention, the term "alkoxy" refers to a straight chain, a branched chain or a cyclic chain. The number of carbon atoms of the alkoxy group is not particularly limited herein, but the alkoxy group preferably has 1 to 10 carbon atoms. Specific examples thereof include, but are not limited to, methoxy, ethoxy, n-propoxy, isopropoxy, isopropoxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentoxy, neopentoxy, isopentyloxy, n-hexyloxy, and benzyloxy.

[0048] As used in the present invention, the term "C6-C60 aryl" refers to a monovalent substituent derived from an aromatic hydrocarbon having a monocyclic ring or a combination of two or more rings and having 6 to 60 carbon atoms. Further, such an aryl may have a form in which two or more rings are simply lateral or fused to each other. Examples of such aryl groups include, but are not limited to, phenyl, biphenyl, naphthyl, phenanthrenyl, anthracenyl, pyrenyl, triphenylene, fluoranthenyl, dimethyl 9,9-dimethylfluorene, 9,9-diphenylfluorene, spirobifluorenyl, etc.

[0049] As used herein, the term "arylene group" refers to a divalent aromatic group derived from an "aryl group" by removing a hydrogen atom. For example, a phenyl group is substituted by removing a hydrogen atom to form a phenylene group, and a naphthyl group is substituted by removing a hydrogen atom to form a naphthylene group.

[0050] As used in the present invention, the term "C3-C60 heteroaryl group" refers to a monovalent substituent derived from a monocyclic heterocyclic or polycyclic aromatic hydrocarbon having 3 to 60 carbon atoms. In this connection, at least one carbon, preferably 1 to 3 carbons in the ring are substituted with a heteroatom such as N, O, S, P, B or Si. In addition, this heteroaryl group may have a form in which two or more rings are simply lateral to each other or fused to each other or fused to an aromatic group. Examples of such heteroaryl groups include pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, indolizinyl, indolyl, indolopyridinyl, purinyl, phenanthroline, quinolyl, isoquinolyl, quinazolinyl, quinoxalinyl, thiazolyl, imidazolyl, oxazolyl, furanyl, thienyl, benzofuranyl, benzothienyl, benzothiazolyl, benzimidazolyl, benzoxazolyl, carbazolyl, dibenzofuranyl, dibenzothienyl and the like, but the present invention is not limited thereto.

[0051] As used in the present invention, the term "heteroarylene" refers to a divalent heteroaryl group derived from a "heteroaryl" by removing a hydrogen atom. For example, a pyridyl group is derived from a pyridylene group by removing a hydrogen atom.

[0052] As used in the present invention, the term "phenylene-substituted naphthylene" refers to any of the following groups, but is not limited thereto, The term "naphthylene-substituted naphthylene" refers to any of the following groups, but is not limited thereto, Indicates a connection key.

[0053] As used in the present invention, the "carbon number is XY" in the expression "Z group having carbon number XY" or "Z group of C(XY)" means the carbon number of the Z group when it is unsubstituted, and does not include the carbon number of the substituent when it is substituted. For example, a C6-C60 aromatic group means that when it is unsubstituted, the carbon number of the aromatic group is any integer between 6 and 60, that is, the carbon number when unsubstituted can be 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20...60.

[0054] As used in the present invention, the term "substituted" means that a hydrogen atom in a compound is replaced by another substituent. The position where the substitution occurs can be the position where the hydrogen atom is replaced. That is, the position is not limited to a specific position, as long as the hydrogen at the position can be replaced by a substituent. For example, carbazolyl includes any of the following groups, but is not limited thereto, as long as it is not otherwise described in this specification,

[0055] Indicates the position of substitution. "Unsubstituted" means that hydrogen atoms are retained.

[0056] In this case, hydrogen atoms include protium, deuterium, and tritium.

[0057] When two or more substituents are present, the two or more substituents may be the same or different.

[0058] As used in the present invention, hydrogen atoms include protium, deuterium and tritium. The compounds of the present invention may contain deuterium atoms of natural origin, or may introduce deuterium atoms by deuterating a portion or all of the raw material compounds. If deuterium atoms are introduced from the raw materials, the deuteration rate may be 100%, or may be less than 100%, or less than 95%, or less than 90%, or less than 80%, and the deuteration rate may also be more than 1%, or more than 5%, or more than 10%. If the deuteration rate is not 100%, it means a mixture of deuterated compounds and undeuterated compounds, or a mixture of completely deuterated compounds and incompletely deuterated compounds, or a mixture of completely deuterated compounds and undeuterated compounds and incompletely deuterated compounds.

[0059] As used in the present invention, terms such as first, second, A, B, etc. are used. The above terms are only used to distinguish components, and do not limit the nature or order of the components to which the terms correspond.

[0060] The core of the present invention is an organic electroluminescent material having the structure shown in formula (1):

[0061]

[0062] represents a double bond or a single bond,

[0063] X 1 Selected from O, S, N, NR,

[0064] X 2 Selected from O, S, N, NR,

[0065] R is selected from hydrogen, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl, L 1 -L 4 are independently selected from a linking bond, a substituted or unsubstituted C6-C60 arylene group, and a substituted or unsubstituted C3-C60 heteroarylene group,

[0066] R 1 -R 4 each independently selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C2-C10 heterocycloalkyl, substituted or unsubstituted C1-C10 alkoxy, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl,

[0067] The substituent in the substituted or unsubstituted group is selected from one or a combination of halogen, cyano, C1-C10 alkyl, C6-C30 aryl, C3-C30 heteroaryl.

[0068] The preferred solution is -L 1 R 1 Not hydrogen; -L 1 R 1 Not hydrogen means L 1 is not a single bond, and R 1 Not hydrogen.

[0069] As an implementation, -L 2 R 2 , -L 3 R 3 , -L 4 R 4 At least one of them is not hydrogen; for example -L 2 R 2 Not hydrogen, i.e. L 2 is not a single bond, and R 2 Not hydrogen; -L 3 R 3 Not hydrogen, i.e. L 3 is not a single bond, and R 3 Not hydrogen; -L 4 R 4 Not hydrogen, i.e. L 4 is not a single bond, and R 4 Not hydrogen.

[0070] As an embodiment, L 2 Selected from single bonds, R 2 Selected from hydrogen.

[0071] As an embodiment, L 3 Selected from single bonds, R 3 Selected from hydrogen.

[0072] As an embodiment, L 4 Selected from single bonds, R 4 Selected from hydrogen.

[0073] The organic electroluminescent material of the present invention, that is, the compound of formula (1) is selected from any one of the following compounds No. 1-122

[0074]

[0075]

[0076]

[0077]

[0078]

[0079]

[0080]

[0081]

[0082] Organic electroluminescent element

[0083] The structure of the organic electroluminescent element of the present invention is a disclosed structure, comprising an anode, a cathode and an organic layer located between the anode and the cathode, wherein the organic layer comprises a light-emitting layer, and at least one layer of the organic layer comprises the compound of the present invention.

[0084] The organic layer may further include one or more of a hole injection layer, a hole transport layer, an electron blocking layer, a hole blocking layer, an electron transport layer, and an electron injection layer, but is not limited thereto.

[0085] The light-emitting element of the present invention may emit fluorescence or phosphorescence or a combination thereof. The light-emitting element may emit light alone or in series with multiple light-emitting units.

[0086] As simple light emitting elements, the following may be cited, but are not limited thereto:

[0087] (1) hole transport layer / fluorescent light emitting layer / electron transport layer;

[0088] (2) hole transport layer / phosphorescent light emitting layer / electron transport layer;

[0089] (3) hole transport layer / first fluorescent light-emitting layer / second fluorescent light-emitting layer / electron transport layer;

[0090] (4) hole transport layer / first phosphorescent light-emitting layer / second phosphorescent light-emitting layer / electron transport layer;

[0091] (5) hole transport layer / fluorescent emitting layer / spacer layer / phosphorescent emitting layer / electron transport layer;

[0092] (6) hole transport layer / electron blocking layer / fluorescent light emitting layer / electron transport layer;

[0093] (7) hole transport layer / electron blocking layer / fluorescent light emitting layer / hole blocking layer / electron transport layer;

[0094] (8) hole transport layer / electron blocking layer / phosphorescent light emitting layer / electron transport layer;

[0095] (9) hole transport layer / electron blocking layer / phosphorescent emitting layer / hole blocking layer / electron transport layer;

[0096] (10) hole injection layer / hole transport layer / phosphorescent light emitting layer / electron transport layer / electron injection layer;

[0097] (11) hole injection layer / hole transport layer / fluorescent light emitting layer / electron transport layer / electron injection layer;

[0098] (12) hole injection layer / hole transport layer / electron blocking layer / phosphorescent light emitting layer / electron transport layer / electron injection layer;

[0099] (13) hole injection layer / hole transport layer / electron blocking layer / fluorescent light emitting layer / electron transport layer / electron injection layer;

[0100] The phosphorescent / fluorescent light-emitting layers mentioned above can each emit light of a different color.

[0101] As a tandem type 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 generally called a charge generation layer, an electron extraction layer, a connecting layer, etc. For example, when stacking a fluorescent light-emitting layer and a phosphorescent light-emitting layer, an intermediate layer is placed between the fluorescent light-emitting layer and the phosphorescent light-emitting layer in order to prevent the excitons generated by the phosphorescent light-emitting layer from diffusing to the fluorescent light-emitting layer or to adjust the balance of carriers.

[0102] When the organic light emitting element includes a plurality of organic material layers, the organic material layers may be formed of the same material or different materials.

[0103] The organic electroluminescent element of the present specification can be manufactured by materials and methods known in the art, except that one or more of the organic material layers is prepared by using a compound comprising the formula (1).

[0104] As the anode material, a material having a relatively large work function may be used, and a transparent conductive oxide, a metal, a conductive polymer, etc. may be used. Specific examples of the anode material include: metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); combinations of metals and oxides such as ZnO:Al or SnO2:Sb; conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), polypyrrole, and polyaniline, etc., but are not limited thereto.

[0105] As the cathode material, a material with a low work function is generally used to facilitate electron injection into the organic material layer, and 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, etc., but are not limited thereto.

[0106] The hole injection layer is a layer that injects holes from the electrode and has the ability to transport holes. In order to reduce the energy level difference between the electrodes, the hole injection layer is mainly prepared based on aromatic amine compounds, and can also be prepared with the following materials, such as copper phthalocyanine in the metal complex, and HATCN (2,3,6,7,10,11-hexacyano-1,4,5,8,9,12-hexaazatriphenylene) with a phenylene structure in the material with the lowest unoccupied molecular orbital energy level. When used as a light-emitting host and dopant, 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 in the aromatic amine compound.

[0107] The hole transport material 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 appropriately receive holes from the anode or the hole injection layer and transfer the holes to the light-emitting layer. Aromatic amine derivatives, triphenyldiamine derivatives, etc. can be used, and low molecular or high molecular materials can also be used.

[0108] The luminescent material is a material that receives holes and electrons from the hole transport layer and the electron transport layer, respectively, and combines the holes and electrons to emit light in the visible light region. The luminescent layer material includes a host material and a doping material. Red, green or blue luminescent materials can be used, and two or more luminescent materials can be mixed as needed. As the luminescent material, a fluorescent material can be used, and a phosphorescent material can also be used. As the luminescent material, a single component material can be used, and a multi-component material can also be used.

[0109] The electron transport material 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 receive electrons from the cathode and transfer the electrons to the light-emitting layer. The 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 be used, and polymer materials and small molecule materials can also be used.

[0110] The electron injection layer is a layer that injects electrons from the electrode. The present application uses LiF, however, the present application is not limited thereto.

[0111] The hole blocking layer is a layer that blocks holes from reaching the cathode.

[0112] The electron blocking layer is a layer that blocks electrons from reaching the anode.

[0113] The organic light-emitting element of the present specification may be a top-emitting element, a bottom-emitting element, or a dual-emission element depending on the materials used.

[0114] The charge generation layer is an intermediate layer between the anode and cathode in a tandem structure element, and is a layer that generates holes and electrons by 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, and can effectively separate charges and effectively transport carriers.

[0115] Those skilled in the art can synthesize the compounds of the present invention by referring to the synthesis of the following compounds and known synthesis methods.

[0116] The following are specific examples of the synthesis of the compounds of the present invention, but are not limited to the compounds exemplified below.

[0117] Example 1: Synthesis of Compound 1

[0118] (1) Synthesis of intermediate 1-1

[0119]

[0120] Under nitrogen atmosphere, 2,6-dibromoaniline (20 g, 79.7 mmol), p-chlorobenzoyl chloride (16.7 g, 95.64 mmol), cuprous iodide (1.5 g, 7.94 mmol), potassium carbonate (22 g, 159.4 mmol), 1,10-phenanthroline (1.43 g, 7.94 mmol) were added to 400 mL of N,N-dimethylformamide in sequence, and reacted at 100 ° C for 6 hours. After the reaction was completed, the mixture was filtered, concentrated and purified by column chromatography to obtain intermediate 1-1 (23 g, yield 95%).

[0121] LC-MS (APCI): 308.08 [M+H] + .

[0122] (2) Synthesis of intermediate 1-2

[0123]

[0124] In a nitrogen atmosphere, under -78°C, n-butyl lithium (74.54 mmol) was added dropwise to a 300 ml tetrahydrofuran solution of intermediate 1-1 (23 g, 74.54 mmol), and the mixture was kept warm for 1 hour. Then, a 100 ml tetrahydrofuran solution of 2-bromo-3-pyridinecarboxaldehyde (14.56 g, 78.27 mmol) was added dropwise to the system, and the mixture was gradually warmed to room temperature and reacted for 2 hours. After the reaction was completed, the mixture was concentrated, washed with water, slurried with n-hexane, and dried to obtain intermediate 1-2 (24 g, yield 96%).

[0125] LC-MS (APCI): 335.15 [M+H] + .

[0126] (3) Synthesis of intermediate 1-3

[0127]

[0128] Intermediate 1-2 (24 g, 71.69 mmol) and (methoxymethyl)triphenylphosphine chloride (29.5 g, 86.03 mmol) were dissolved in 500 mL of dichloromethane, and potassium tert-butoxide (9.65 g, 86.03 mmol) was added in batches at -10°C under nitrogen protection, and the temperature was raised to room temperature for reaction for 1 hour. After the reaction was completed, the liquid was extracted and separated, and the intermediate 1-3 (27.9 g, yield 97%) was obtained after concentration and column chromatography.

[0129] LC-MS (APCI): 363.17 [M+H] + .

[0130] (4) Synthesis of Intermediates 1-4

[0131]

[0132] At -10°C, trifluoromethanesulfonic acid (20.4 mL, 230.7 mmol) was added dropwise to a solution of intermediate 1-3 (27.9 g, 69.70 mmol) in 600 mL of hexafluoroisopropanol, and the mixture was kept warm for 2 hours. After the reaction was completed, the mixture was concentrated, the pH was adjusted to neutral with saturated sodium bicarbonate solution, extracted with DCM, concentrated, and column chromatography was performed to obtain intermediate 1-4 (13.4 g, yield 58%).

[0133] LC-MS (APCI): 331.19 [M+H] + .

[0134] (4) Synthesis of Compound 1

[0135]

[0136] Intermediate 1-4 (13.4 g, 40.5 mmol), 1-pyreneboronic acid (10.96 g, 44.55 mmol), potassium carbonate (11.2 g, 81 mmol), DPPF palladium dichloride (890 mg, 1.22 mmol) were dissolved in a mixed solution of 150 mL toluene, 75 mL ethanol, and 75 mL water, and refluxed for 6 hours under nitrogen protection. After separation of water, compound 1 (18 g, yield 90%) was obtained by column chromatography.

[0137] LC-MS (APCI): 497.35 [M+H] + .

[0138] 1H NMR(400MHz,Methylene Chloride-d2)δ9.32(d,1H),8.67(d,2H),8.36–8.21(m,5H),8.18–8.02(m,8H),7.92(d,2H),7.84(d,1H),7.66(dd,1H).

[0139] The following application examples further illustrate the application of the organic electroluminescent material and the organic electroluminescent element comprising the same according to the present invention.

[0140] Example 1

[0141] This embodiment provides an organic electroluminescent element, such as Figure 1As shown, it includes a stacked first electrode layer 1, a hole injection layer 2, a hole transport layer 3, a light-emitting layer 4, an electron transport layer 5, an N-type charge generation layer 6, a P-type charge generation layer 7, a hole transport layer 8, a light-emitting layer 9, an electron transport layer 10, an electron injection layer 11 and a second electrode layer 12, wherein the hole injection layer 2, the hole transport layer 3, the light-emitting layer 4 and the electron transport layer 5 are the first light-emitting unit 100, and the hole transport layer 8, the light-emitting layer 9, the electron transport layer 10 and the electron injection layer 11 are the second light-emitting unit 200.

[0142] The specific component structure is:

[0143] ITO(100nm) / NPD:F4-TCNQ(10%)(10nm) / NPD(120nm) / BH:BD(3%)(20nm) / TmPyPB(10nm) / Bphen:Li(2%)( 10nm) / NPD:F4-TCNQ(10%)(20nm) / NPD(20nm) / BH:BD(3%)(20nm) / Alq3(10nm) / LiF(0.5nm) / Al(200nm).

[0144] Component preparation process:

[0145] The bottom-emitting glass substrate used in this embodiment was purchased from Guangdong Xinli Display Technology Co., Ltd., and 100 nm ITO was used as the first electrode layer 1. First, the bottom-emitting glass substrate was cleaned with ITO cleaning agent, deionized water, and isopropyl alcohol in sequence, and then the bottom-emitting glass substrate was baked at 180 degrees Celsius for 30 minutes to dry it.

[0146] Then put the bottom luminescent glass substrate into the evaporation chamber and place it in a vacuum chamber of about 10 -8In the case of torr, each organic layer is deposited on the ITO anode in sequence by thermal vacuum evaporation at a rate of 0.2-2 angstroms / second. Among them, F4-TCNQ (mass content 10%) is doped into NPD to form a thickness of 10nm as a hole injection layer. NPD is formed to a thickness of 120nm as a hole transport layer, and the anthracene main body ADN (9,10-di(naphtha-2-yl-)anthracene) is doped with a 3% mass content of pyrene dopant 1,6-bis(diphenylamino)pyrene to form a blue light-emitting layer with a thickness of 20nm. TmPyPB is formed to a thickness of 10nm as the first electron transport layer, and BPhen (4,7-Diphenyl-1,10-phenanthroline) is doped with 2% mass content of Li to form an N-type charge generation layer 6 with a thickness of 10nm. F4-TCNQ with a mass content of 10% is doped on NPD. A P-type charge generation layer with a thickness of 20 nm is formed, NPD with a thickness of 20 nm is formed as a hole transport layer, an anthracene main body ADN (9,10-di(naphtha-2-yl-)anthracene) is doped with a pyrene dopant 1,6-bis(diphenylamino)pyrene with a mass content of 3% to form a blue light-emitting layer with a thickness of 20 nm, Alq3 (Tris-(8-hydroxyquinolinato)aluminum) is formed with a thickness of 10 nm as a second electron transport layer, LiF is formed with a thickness of 0.5 nm as an electron injection layer, and Al is formed with a thickness of 200 nm as a cathode.

[0147] Finally, the component was transferred back to the glove box and encapsulated with a glass cover and a moisture absorbent to complete the component, which was recorded as organic electronic component 1.

[0148]

[0149] Contrast structure

[0150] Bphen(4,7-Diphenyl-1,10-phenanthroline)

[0151]

[0152] Example 2

[0153] Charge Generation Layer The N-type charge generation layer 6 is prepared by using the compound prepared in Example 1 of the present invention instead of the Bphen material, and the organic electronic element 2 is prepared by the same method.

[0154] Life test method: Apply voltage to the obtained organic electroluminescent element so that the current density reaches 30mA / cm2 The time until the brightness reaches 95% of the initial brightness (LT95 (unit: hour)) was measured.

[0155] The driving voltage is at a current density of 15 mA / cm 2 The following test results are shown in Table 1.

[0156] Table 1

[0157]

[0158]

[0159] In summary, the organic electroluminescent element prepared by the compound of the present invention has a lower driving voltage and a longer service life than the organic electroluminescent element prepared by Bphen, and is therefore suitable as a material for an organic electroluminescent element.

[0160] In this specification, each embodiment is described in a progressive manner, and each embodiment focuses on the differences from other embodiments. The same or similar parts between the embodiments can be referred to each other. For the device disclosed in the embodiment, since it corresponds to the method disclosed in the embodiment, the description is relatively simple, and the relevant parts can be referred to the method part.

[0161] The above is a detailed introduction to an organic electroluminescent material and an organic electroluminescent element comprising the same provided by the present invention. Specific examples are used herein to illustrate the principles and implementation methods of the present invention. The description of the above embodiments is only used to help understand the method of the present invention and its core idea. It should be pointed out that for ordinary technicians in this technical field, without departing from the principle of the present invention, several improvements and modifications can be made to the present invention, and these improvements and modifications also fall within the scope of protection of the claims of the present invention.

Claims

1. An organic electroluminescent material, characterized in that The compound has the structure shown in formula (1): represents a double bond or a single bond, X 1 Selected from O, S, N, NR, X 2 Selected from O, S, N, NR, R is selected from hydrogen, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl, L 1 -L 4 are independently selected from a linking bond, a substituted or unsubstituted C6-C60 arylene group, and a substituted or unsubstituted C3-C60 heteroarylene group, R 1 -R 4 each independently selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C2-C10 heterocycloalkyl, substituted or unsubstituted C1-C10 alkoxy, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl, The substituent is selected from one or a combination of halogen, cyano, C1-C10 alkyl, C6-C30 aryl, C3-C30 heteroaryl.

2. The organic electroluminescent material according to claim 1, characterized in that The compound has a structure shown in formula (1-1) or formula (1-2) 3. The organic electroluminescent material according to claim 1, characterized in that ； The C6-C60 arylene group is selected from the following groups: phenylene, naphthylene, biphenylene, phenylene-substituted naphthylene, naphthylene-substituted naphthylene, anthrylene, phenanthrenyl, fluoranthenyl, triphenylene, perylene, pyrenyl, benzopyrenyl, ... base; The C3-C60 heteroarylene group is selected from the following groups: dibenzofuranyl, dibenzothienyl, pyridylene; the C1-C10 alkyl group is selected from the following groups: methyl, ethyl, tert-butyl; The C3-C10 cycloalkyl group is selected from the following groups: cyclopropyl, cyclohexyl, cycloadamantyl; The C6-C60 aryl group is selected from the following groups: phenyl, biphenyl, naphthyl, anthracenyl, phenanthrenyl, fluoranthenyl, triphenylene, peryl, pyrenyl, benzopyrenyl, base; The C3-C60 heteroaryl group is selected from the following groups: dibenzofuranyl, dibenzothienyl, and pyridyl.

4. The organic electroluminescent material according to claim 1, characterized in that: L 1 , L 2 , L 3 , L 4 Each independently selected from a single bond, phenylene, biphenylene, phenylene-substituted naphthylene, biphenylene, naphthylene, anthrylene, phenanthrenyl, pyrenyl, perylene, triphenylene, fluoranthenyl, dibenzofuranyl, dibenzothiophenylene, The following groups in which one or more hydrogen atoms are replaced by substituents: phenylene, biphenylene, phenylene-substituted naphthylene, biphenylene, naphthylene, anthrylene, phenanthrenyl, pyrenyl, perylene, triphenylene, fluoranthenyl, dibenzofuranyl, dibenzothiophenylene, wherein the substituents are each independently selected from one or a combination of deuterium, halogen, and cyano.

5. The organic electroluminescent material according to claim 1, characterized in that: R 1 , R 2 , R 3 , R 4 Each independently selected from hydrogen, halogen, methyl, ethyl, tert-butyl, cyclopropyl, cyclohexyl, cycloadamantyl, phenyl, naphthyl, anthracenyl, phenanthryl, phenyl-substituted anthracenyl, pyrenyl, perylenyl, triphenylene, fluoranthenyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, The following groups in which one or more hydrogen atoms are replaced by substituents: methyl, ethyl, tert-butyl, cyclopropyl, cyclohexyl, cycloadamantyl, phenyl, naphthyl, anthracenyl, phenanthryl, phenyl-substituted anthracenyl, pyrenyl, peryl, triphenylene, fluoranthenyl, dibenzofuranyl, dibenzothienyl, carbazolyl, wherein the substituents are each independently selected from one or a combination of deuterium, halogen, cyano, phenyl, naphthyl, anthracenyl, phenanthryl, phenyl-substituted anthracenyl, pyrenyl, triphenylene, fluoranthenyl, dibenzofuranyl, dibenzothienyl, carbazolyl.

6. The organic electroluminescent material according to claim 1, characterized in that: -L 1 R 1 Not hydrogen.

7. The organic electroluminescent material according to claim 1, characterized in that Formula (1) is selected from any of the following compounds No. 1-122 8. An organic electroluminescent element, characterized in that The organic electroluminescent element comprises: A first electrode, a second electrode, and an organic material layer disposed between the first electrode and the second electrode, wherein one or more layers of the organic material layer comprises the organic electroluminescent material according to any one of claims 1 to 7.

9. The organic electroluminescent element according to claim 8, characterized in that The organic material layer comprises at least two light-emitting units, the light-emitting units comprise electron transport layers, a charge generation layer is comprised between the light-emitting units, the charge generation layer comprises an N-type charge generation layer and a P-type charge generation layer, and the N-type charge generation layer and / or the electron transport layer comprise the organic electroluminescent material according to any one of claims 1 to 7.

10. An electronic device comprising one or more of a display, a monitor, and a lighting device, wherein the electronic device comprises the organic electroluminescent element according to claim 8 or 9.

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