Arylamine compound and organic electroluminescent device comprising same

Abstract

The invention provides an arylamine compound, belongs to the technical field of organic light-emitting materials, and also relates to an application of the compound in an organic light-emitting device. The arylamine compound has a structure as shown in a formula (1): the organic electroluminescent element comprises a first electrode, a second electrode and one or more organic layers between the first electrode and the second electrode, and at least one organic layer contains the arylamine compound provided by the invention. The prepared organic electroluminescent device can improve the luminous efficiency and prolong the service life of the device, and is a high-performance organic electroluminescent material.

Description

Technical Field

[0001] The present invention belongs to the technical field of photoelectric materials, and in particular relates to an organic electroluminescent device of an aromatic amine compound and a preparation method thereof. Background Art

[0002] An organic light emitting diode (OLED) is a self-luminous display device based on organic electroluminescent materials. Unlike existing liquid crystal display devices, it does not require a backlight source and is thin, making it a technology suitable for flexible devices (flexible light-emitting display devices). An organic light emitting diode (OLED) that utilizes the phenomenon of organic light emitting diodes typically has an anode, a cathode, and an organic layer therebetween. To improve the efficiency and stability of an organic light emitting diode, the organic layer typically consists of a multilayer structure composed of various substances, such as a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, and an electron injection layer.

[0003] A luminescence-assisting layer is often added between the hole transport layer and the light-emitting layer to improve lifetime and efficiency. The luminescence-assisting layer primarily assists the hole transport layer, reducing the potential barrier between the hole transport layer and the light-emitting layer, lowering the driving voltage of the organic electroluminescent device and further increasing the utilization of holes, thereby improving the device's luminous efficiency and lifetime.

[0004] Research on organic electroluminescent materials has been extensively conducted in academia and industry, but stable and efficient organic layer materials for organic electroluminescent devices have yet to be fully developed. Therefore, developing higher-performance organic functional materials to reduce driving voltage, improve device luminous efficiency, and extend device life is of great practical value. Summary of the Invention

[0005] The object of the present invention is to provide an organic electroluminescent material of an aromatic amine compound and the application of the compound in an organic electroluminescent device, so as to achieve high luminous efficiency and long life of the organic electroluminescent device.

[0006] The present invention provides an aromatic amine compound having a structure shown in formula (1):

[0007]

[0008]

[0009] Among them, Ar 1 、Ar 2 are the same or different, each independently selected from hydrogen, substituted or unsubstituted C6-C60 aryl, or substituted or unsubstituted C6-C60 heteroaryl;

[0010] L 1 -L 4 the same or different, each independently selected from a single bond, a substituted or unsubstituted C6-C60 arylene group, provided that L 1 -L 4 At least one of them is not a single bond, and L 1 , L 2 Not all are single bonds;

[0011] R 1 -R 4 is selected from substituted or unsubstituted methyl;

[0012] The substituents in the "substituted or unsubstituted" are each independently selected from one of deuterium, halogen, cyano, C1-C10 alkyl, C3-C10 cycloalkyl, C6-C30 aryl, C6-C30 aromatic ring group, C3-C30 heteroaryl, C3-C30 heteroaromatic ring group or a combination thereof,

[0013] The heteroatoms of the heteroaryl group and heteroaromatic ring group are selected from one or more of oxygen, sulfur and nitrogen.

[0014] Furthermore, in an optional embodiment of the present invention, the compound has a structure shown in formula (2) or formula (3):

[0015]

[0016] In formula (2) and formula (3), Ar 1 Selected from hydrogen, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C6-C60 heteroaryl;

[0017] L 1 -L 4 the same or different, each independently selected from a single bond, a substituted or unsubstituted C6-C60 arylene group, provided that L 1 , L 2 Not all are single bonds;

[0018] R 1 -R 4 is selected from substituted or unsubstituted methyl;

[0019] The substituents in the "substituted or unsubstituted" are each independently selected from one of deuterium, halogen, cyano, C1-C10 alkyl, C3-C10 cycloalkyl, C6-C30 aryl, C6-C30 aromatic ring group, C3-C30 heteroaryl, C3-C30 heteroaromatic ring group or a combination thereof,

[0020] The heteroatoms of the heteroaryl group and heteroaromatic ring group are selected from one or more of oxygen, sulfur and nitrogen.

[0021] Further, in an optional embodiment of the present invention, the Ar 1 is selected from hydrogen, substituted or unsubstituted groups:

[0022]

[0023] Furthermore, in an optional embodiment of the present invention, the L 1 -L 4 The same or different, each independently selected from a single bond, substituted or unsubstituted following groups:

[0024]

[0025]

[0026] , provided that L 1 、L 2 Not single bond at the same time.

[0027] Furthermore, in an optional embodiment of the present invention, -L 1 -L 2 - substituted or unsubstituted following groups:

[0028]

[0029] Furthermore, in an optional embodiment of the present invention, the L 3 Selected from single bond, phenylene, said L 1 、L 2 、L 4 Each independently selected from a single bond, a phenylene group, a biphenylene group, provided that L 1 、L 2 Not single bond at the same time.

[0030] Further, in an optional embodiment of the present invention, the compound is selected from the following structures numbered 1-1 to 1-72, 2-1 to 2-72:

[0031]

[0032]

[0033]

[0034]

[0035]

[0036]

[0037]

[0038]

[0039] On the other hand, the present invention also provides a use of the aromatic amine compound as an organic electroluminescent element material.

[0040] On the other hand, the present invention also provides an organic electroluminescent element comprising a first electrode, a second electrode and an organic material layer between the first electrode and the second electrode, wherein the organic material layer comprises a light-emitting layer, and the organic material layer has one or more, at least one organic material layer comprises the aromatic amine compound described in the present invention.

[0041] Preferably, the organic material layer includes a hole transport region, a light-emitting layer, and an electron transport region, wherein the hole transport region is located between the anode and the light-emitting layer, and the electron transport region is located between the light-emitting layer and the cathode;

[0042] The hole transport region comprises the aromatic amine compound.

[0043] More preferably, the hole transport region comprises at least one layer selected from the group consisting of a hole injection layer, a hole transport layer, and a luminescence-assisting layer; and the luminescence-assisting layer comprises the aromatic amine compound described in the present invention.

[0044] On the other hand, the present invention further provides an electronic device, characterized in that the electronic device includes one or more of a display, a monitor, and a lighting device, and the electronic device contains the organic electroluminescent element.

[0045] The beneficial effects of the present invention are:

[0046] The aromatic amine compound of the present invention can be used as a high-performance organic electroluminescent material. When used in a luminescent auxiliary layer, the efficiency and life of the compound in the device can be effectively improved, and the overall performance of the prepared device can be improved. BRIEF DESCRIPTION OF THE DRAWINGS

[0047] Figure 1 This is a schematic structural diagram of the organic electroluminescent element described in Application Example 1, wherein: 1. anode, 2. hole injection layer, 3. hole transport layer, 4. luminescence auxiliary layer, 5. luminescent layer, 6. electron transport layer, 7. electron injection layer and 8. cathode. DETAILED DESCRIPTION

[0048] 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 concept of the present invention to those skilled in the art.

[0049] By reference to the following specific embodiments and the examples contained therein, the present disclosure can be more easily understood. Before disclosing and describing the compounds, devices and / or methods of the present invention, it should be understood that, unless otherwise stated, they are not limited to specific synthetic methods or specific reagents, as these can vary. It should also be understood that the terms used in the present invention are only used to describe specific aspects and are not intended to be limiting. Although any methods and materials similar or equivalent to those described herein can be used in this practice or test, exemplary methods and materials are now described.

[0050] Unless otherwise specified, the experimental methods used in the following examples are conventional methods; the reagents, materials, etc. used in the following examples are all commercially available unless otherwise specified.

[0051] Explanation of terms

[0052] As used in the present invention, Refers to replacing a position.

[0053] As used herein, the term "halogen" may include fluorine, chlorine, bromine or iodine.

[0054] As used herein, 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.

[0055] As used herein, 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 groups include, but are not limited to, cyclopropane, cyclobutane, cyclopentane, cyclohexane, norbornyl, adamantane, and the like.

[0056] As used herein, the term "C2-C10 heterocycloalkyl" refers to a monovalent substituent having a monocyclic or polycyclic ring of 2 to 10 carbon atoms, and containing at least one heteroatom in the ring, wherein the heteroatom is selected from O, S, N, P, and Si.

[0057] As used herein, the term "alkoxy" refers to a linear, branched, or cyclic chain. The number of carbon atoms in the alkoxy group is not particularly limited, but the alkoxy group preferably has 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.

[0058] 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 group may have a form in which two or more rings are simply lateral to each other 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.

[0059] As used herein, the term "arylene" refers to a divalent aromatic group derived from an "aryl" group by removing a hydrogen atom. For example, a phenyl group can be converted to a phenylene group by removing a hydrogen atom, and a naphthyl group can be converted to a naphthylene group by removing a hydrogen atom.

[0060] As used herein, the term "C3-C60 heteroaryl" refers to a monovalent substituent derived from a monocyclic or polycyclic heterocyclic aromatic hydrocarbon having 3 to 60 carbon atoms. In this connection, at least one carbon, preferably 1 to 3 carbon atoms, in the ring is substituted with a heteroatom such as N, O, S, P, B, or Si. In addition, such a heteroaryl group may have a form in which two or more rings are simply attached to each other or fused to each other or 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.

[0061] As used herein, the term "heteroarylene" refers to a divalent heteroaryl group derived from a "heteroaryl" by removing a hydrogen atom. For example, a pyridyl group can be converted into a pyridylene group by removing a hydrogen atom from a pyridyl group.

[0062] As used in the present invention, the "carbon number of AA-BB" in the expression "Z group having AA-BB carbon atoms" or "Z group having C(AA-BB)" means the carbon number of AA-BB carbon atoms in 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-C30 aryl group means that when it is unsubstituted, the number of carbon atoms in the aryl group is any integer between 6 and 30, that is, the number of carbon atoms when it is unsubstituted can be 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20...30.

[0063] 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, unless otherwise specified in this specification:

[0064]

[0065] "Unsubstituted" means that hydrogen atoms remain, and in this case, hydrogen atoms include protium, deuterium, and tritium.

[0066] When two or more substituents are present, the two or more substituents may be the same or different.

[0067] As used in the present invention, hydrogen atoms include protium, deuterium, and tritium. The compounds of the present invention may contain deuterium atoms from natural sources, or deuterium atoms may be introduced 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 less than 100%, or less than 95%, or less than 90%, or less than 80%. The deuteration rate may also be greater than 1%, or greater than 5%, or greater than 10%. If the deuteration rate is not 100%, it represents a mixture of deuterated and undeuterated compounds, or a mixture of a fully deuterated and incompletely deuterated compound, or a mixture of a fully deuterated and undeuterated compound and an incompletely deuterated compound.

[0068] As used in the present invention, terms such as first, second, A, and B 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.

[0069] organic electroluminescent elements

[0070] 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. The organic layer comprises a light-emitting layer, and at least one layer of the organic layer comprises the compound of the present invention.

[0071] The organic layer further includes one or more of a hole injection layer, a hole transport layer, a light-emitting auxiliary layer, a hole blocking layer, an electron transport layer, and an electron injection layer, but is not limited thereto.

[0072] 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 the form of a series of multiple light-emitting units.

[0073] As simple light emitting elements, the following may be mentioned, but are not limited to these:

[0074] (1) hole transport layer / fluorescent light emitting layer / electron transport layer;

[0075] (2) hole transport layer / phosphorescent light emitting layer / electron transport layer;

[0076] (3) hole transport layer / first fluorescent light-emitting layer / second fluorescent light-emitting layer / electron transport layer;

[0077] (4) hole transport layer / first phosphorescent light-emitting layer / second phosphorescent light-emitting layer / electron transport layer;

[0078] (5) hole transport layer / fluorescent emitting layer / spacer layer / phosphorescent emitting layer / electron transport layer;

[0079] (6) hole transport layer / luminescence auxiliary layer / fluorescent light emitting layer / electron transport layer;

[0080] (7) hole transport layer / luminescence auxiliary layer / fluorescent light emitting layer / hole blocking layer / electron transport layer;

[0081] (8) hole transport layer / luminescence auxiliary layer / phosphorescent light emitting layer / electron transport layer;

[0082] (9) hole transport layer / luminescence auxiliary layer / phosphorescent light emitting layer / hole blocking layer / electron transport layer;

[0083] (10) hole injection layer / hole transport layer / phosphorescent light emitting layer / electron transport layer / electron injection layer;

[0084] (11) hole injection layer / hole transport layer / fluorescent light emitting layer / electron transport layer / electron injection layer;

[0085] (12) hole injection layer / hole transport layer / luminescence auxiliary layer / phosphorescent light emitting layer / electron transport layer / electron injection layer;

[0086] (13) hole injection layer / hole transport layer / luminescence auxiliary layer / fluorescent light emitting layer / electron transport layer / electron injection layer;

[0087] The phosphorescent / fluorescent light-emitting layers may each emit light of a different color.

[0088] As a tandem organic electroluminescent element, it can be an anode / first light-emitting unit / intermediate layer / second light-emitting unit / cathode. The intermediate layer can also generally be 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.

[0089] 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.

[0090] 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 formula (1).

[0091] 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, or the like may be used.

[0092] As the cathode material, a material having 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.

[0093] The hole injection layer (HIL) is a layer that injects holes from the electrodes and has the ability to transport holes. To reduce the energy level difference between the electrodes, the HIL is mainly prepared based on aromatic amine compounds, but other materials with hole transport capabilities can also be used.

[0094] The hole transport layer receives holes from the hole injection layer and transports the holes to the light emitting layer, and the hole transport material is suitably a material having high hole mobility that can receive holes from the anode or the hole injection layer and transfer the holes to the light emitting layer.

[0095] The luminescent auxiliary layer is a layer that blocks electrons from reaching the anode. It can adjust the energy difference between the hole transport region and the luminescent layer, which is conducive to the entry of holes into the luminescent layer, while reducing the probability of electrons entering the hole transport region from the luminescent layer. Commonly used are aromatic amine derivatives.

[0096] A luminescent material is a material that receives holes and electrons from the hole transport layer and 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 dopant material. Red, green, or blue luminescent materials can be used, and two or more luminescent materials can be mixed as needed. Both fluorescent and phosphorescent materials can be used as luminescent materials. The luminescent material can be a single-component material or a multi-component material.

[0097] The electron transport layer 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. It is a material with high electron mobility. 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. Metal complexes, and polymer materials and small molecule materials can also be used.

[0098] The electron injection layer is a layer that injects electrons from the electrode.

[0099] 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.

[0100] In one embodiment of the present invention, the method for forming each layer is not particularly limited. Conventionally known methods such as vacuum evaporation and spin coating can be used. Each layer, such as the light-emitting layer, can be formed by vacuum evaporation, molecular beam evaporation (MBE), or by a known coating method such as dipping, spin coating, casting, rod coating, or roller coating of a solution dissolved in a solvent.

[0101] 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.

[0102] Synthesis formula: The following general formula is only one method for synthesizing the compounds of the present invention. Other methods can also be used to synthesize the compounds of the present invention.

[0103]

[0104] Where X1 represents halogen, different substitution positions can be synthesized using the same method. 1 -L 4 、Ar 1 -Ar 2 , have the same meaning as in the present invention.

[0105] Synthesis Example:

[0106] Example 1: Preparation of Compound 2-11

[0107] 1. Synthesis of intermediate compound 2-11-1

[0108]

[0109] Under nitrogen, 2-bromo-9,10-phenanthrenequinone (4.35 g, 15.07 mmol) was added to anhydrous ether (300 mL). After melting, methylmagnesium bromide (7.52 g, 63.03 mmol) was slowly added at -78°C. The mixture was cooled to room temperature and stirred. After the reaction was complete, the mixture was extracted with dichloromethane, and the extract was dried over anhydrous magnesium sulfate and concentrated. 2-11-1 (4.28 g, 90%) was isolated by silica gel chromatography.

[0110] LC-MS (APCI): 316.57 [M+H] + .

[0111] 2. Synthesis of intermediate compound 2-11-2

[0112]

[0113] Under a nitrogen atmosphere, compound 2-11-1 (13.56 g, 43.00 mmol) and 4-chlorophenylboronic acid (6.72 g, 43.00 mmol) were added to a three-necked flask, and a mixed solution of 150 mL of tetrahydrofuran and 50 mL of water was added, potassium carbonate (8.95 g, 64.83 mmol) and tetrakis(triphenylphosphine)palladium (0.93 g, 0.80 mmol) were added, and the mixture was heated to 70-80°C for reaction. After the reaction was completed, the liquid was extracted and separated, and the organic phase was concentrated and purified by column chromatography to obtain compound 2-11-2 (10.29 g, yield 69%).

[0114] LC-MS (APCI): 347.16 [M+H] + .

[0115] 3. Synthesis of Compound 2-11-5

[0116]

[0117] 2-11-3 (13.50 g, 41.78 mmol) and compound 2-11-4 (7.24 g, 42.79 mmol) were completely dissolved in 200 mL of xylene. NaOt-Bu (8.30 g, 86.49 mmol) and bis(tri-tert-butylphosphine)palladium (0.32 g, 0.63 mmol) were added, and the mixture was heated and stirred for 3 hours. The mixture was cooled to room temperature and extracted with distilled water and ethyl acetate. The organic layer was dried over MgSO4, filtered, and concentrated. Compound 2-11-5 (13.41 g, 78% yield) was purified by column chromatography.

[0118] LC-MS (APCI): 412.78 [M+H] + .

[0119] 4. Synthesis of Compound 2-11

[0120]

[0121] After completely dissolving 2-11-5 (14.93 g, 36.28 mmol) and 2-11-2 (12.61 g, 36.35 mmol) in 200 mL of xylene, NaOt-Bu (8.30 g, 86.59 mmol) and bis(tri-tert-butylphosphine)palladium(0) (0.32 g, 0.63 mmol) were added, and the mixture was heated and stirred for 3 hours. The mixture was cooled to room temperature and extracted with distilled water and ethyl acetate. The organic layer was dried over MgSO4, filtered, and concentrated. Compound 2-11 (17.02 g, 65% yield) was obtained by purification by column chromatography.

[0122] LC-MS (APCI): 722.24 [M+H] + .

[0123] Example 2: Synthesis of Compounds 1-51

[0124]

[0125] Prepared according to the same synthesis method as Example 1, replacing compound 2-11-3 with compound 1-51-3, and compound 2-11-4 with compound 1-51-4, the compound 1-51 can be synthesized according to the above synthesis route (21.55 g, yield 83%, the yield is the synthesis yield of the reaction of 1-51-5 and 2-11-1).

[0126] LC-MS (APCI): 646.08 [M+H] + .

[0127] Example 3: Synthesis of Compound 1-65

[0128]

[0129] Prepared according to the same synthesis method as Example 1, replacing compound 2-11-3 with compound 1-65-3, and compound 2-11-4 with compound 1-65-4, the compound 1-65 can be synthesized according to the above synthesis route (21.55 g, yield 75%, the yield is the synthesis yield of the reaction of 1-65-5 and 2-11-1).

[0130] LC-MS (APCI): 660.17 [M+H] + .

[0131] Example 4: Synthesis of Compounds 1-72

[0132]

[0133] Prepared according to the same synthesis method as Example 1, replacing compound 2-bromo-9,10-phenanthrenequinone with compound 3-bromo-9,10-phenanthrenequinone, compound 2-11-3 with compound 1-72-3, and compound 2-11-4 with compound 1-72-4, the compound 1-72 (21.55 g, yield 77%, the yield being the synthesis yield of the reaction of 1-72-5 and 1-72-1) can be synthesized according to the above synthesis route.

[0134] LC-MS (APCI): 676.45 [M+H] + .

[0135] Example 5: Synthesis of Compounds 2-19

[0136]

[0137] Prepared according to the same synthesis method as Example 1, replacing compound 2-11-3 with compound 1-51-3, and compound 2-11-4 with compound 1-19-4, compound 1-72 (21.55 g, yield 69%, the yield being the synthesis yield of the reaction of 1-19-5 and 2-11-2) can be synthesized according to the above synthesis route.

[0138] LC-MS (APCI): 773.58 [M+H] + .

[0139] Example 6: Synthesis of Compound 2-69

[0140]

[0141] Prepared according to the same synthesis method as Example 1, replacing compound 2-11-3 with compound 2-69-3, compound 2-11-4 with compound 2-69-4, and compound 2-11-4 with compound 1-72-1. Compound 2-69 (21.55 g, yield 76%, which is the synthesis yield of the reaction of 2-69-5 and 1-72-1) can be synthesized according to the above synthesis route.

[0142] LC-MS (APCI): 752.78 [M+H] + .

[0143] Device preparation example:

[0144] Application Example 1

[0145] This embodiment provides an organic electroluminescent element, such as Figure 1 As shown, it includes 1, an anode, 2, a hole injection layer, 3, a hole transport layer, 4, a light-emitting auxiliary layer, 5, a light-emitting layer, 6, an electron transport layer, 7, an electron injection layer and 8, a cathode stacked from bottom to top.

[0146] The specific device structure is:

[0147] ITO / HT:HAT-CN(10nm,97:3) / HT(120nm) / BP(10nm) / BH-1:BD-1(97:3v / v%)(30nm) / ET:Liq(35nm,1:1) / LiF(0.2nm) / Al(150nm).

[0148] Device preparation process:

[0149] An organic electroluminescent device 1 was manufactured by vapor-depositing HT:HAT-CN (97:3) on an ITO substrate to form a 10 nm thick hole injection layer (HIL), vapor-depositing HT on the hole injection layer to form a 120 nm thick hole transport layer (HTL), vapor-depositing BP-1 on the hole transport layer to form a 10 nm thick emission-assisting layer (EBL), vapor-depositing BH:BD (97:3 v / v%) on the emission-assisting layer to form a 30 nm thick emission layer (EML), vapor-depositing ET:Liq (1:1) to form a 35 nm thick electron transport layer (ETL), vapor-depositing LiF to form a 0.2 nm thick electron injection layer, and vapor-depositing Al to form a 150 nm thick cathode. This is referred to as Comparative Example 1.

[0150]

[0151] Device Comparative Example 2

[0152] The luminescence auxiliary layer 4 was prepared by using compound BP-2 instead of BP-1, and the organic electroluminescent device 2 was manufactured by the same method as that of the embodiment of Comparative Example 1.

[0153] Device Comparative Example 3

[0154] The luminescence auxiliary layer 4 was prepared by using compound BP-3 instead of BP-1 material, and the organic electroluminescent device 3 was prepared by the same method as the embodiment of the comparative example 1 above.

[0155] Device Examples

[0156] The luminescence auxiliary layer 4 was prepared by using compound 2-11 instead of BP-1 material, and the organic electroluminescent device 4 was prepared by the same method as that of the embodiment of Comparative Example 1 above.

[0157] The luminescence auxiliary layer 4 was prepared by using compound 1-51 instead of BP-1 material, and the organic electroluminescent device 5 was prepared by the same method as that of the embodiment of Comparative Example 1 above.

[0158] The luminescence auxiliary layer 4 was prepared by using compound 1-65 instead of BP-1 material, and the organic electroluminescent device 6 was prepared by the same method as that of the embodiment of Comparative Example 1 above.

[0159] The luminescence auxiliary layer 4 was prepared by using compound 1-72 instead of BP-1 material, and the organic electroluminescent device 7 was prepared by the same method as that of the embodiment of Comparative Example 1 above.

[0160] The luminescence auxiliary layer 4 was prepared by using compound 2-19 instead of BP-1 material, and the organic electroluminescent device 8 was prepared by the same method as that of the embodiment of Comparative Example 1 above.

[0161] The luminescence auxiliary layer 4 was prepared by using compound 2-69 instead of BP-1 material, and the organic electroluminescent device 9 was prepared by the same method as that of the embodiment of Comparative Example 1 above.

[0162] Test results

[0163] Life test method: Apply voltage to the obtained organic electroluminescent element so that the current density reaches 30mA / cm 2 The time until the brightness reaches 95% of the initial brightness (LT95 (unit: hour)) was measured, and the life of Comparative Example 1 was set as 100%, and the relative life values ​​of each Comparative Example and Example were obtained.

[0164] The driving voltage is at a current density of 15 mA / cm 2 The following test was performed, with the driving voltage of Comparative Example 1 being 100%, to obtain relative values ​​of the driving voltages of the comparative examples and the embodiment.

[0165] Current efficiency at current density 15mA / cm 2 The current efficiency of Comparative Example 1 was taken as 100% to obtain the relative values ​​of the current efficiency of each comparative example and embodiment. The test results are shown in Table 1.

[0166] Table 1

[0167] Light-emitting auxiliary layer Drive voltage, V Current efficiency, % Life LT95%,% Comparative Example 1 BP-1 100 100 100 Comparative Example 2 BP-2 98 100 96 Comparative Example 3 BP-3 99 99 95 Example 1 2-11 100 109 113 Example 2 1-51 99 104 102 Example 3 1-65 98 105 103 Example 4 1-72 99 107 106 Example 5 2-19 100 111 116 Example 6 2-69 99 108 110

[0168] From the results shown in Table 1 above, it can be seen that the application of the aromatic amine compound of the present invention in the light-emitting auxiliary layer can significantly improve the luminous efficiency and life of the organic electroluminescent device, and is a high-performance organic electroluminescent material.

[0169] The basic principles, main features, and advantages of the present invention are shown and described above. Those skilled in the art should understand that the present invention is not limited to the above embodiments. The above embodiments and descriptions are merely illustrative of the principles of the present invention. Various changes and modifications may be made to the present invention without departing from the spirit and scope of the present invention. Such changes and modifications are intended to fall within the scope of the present invention. The scope of protection claimed in the present invention is defined by the appended claims and their equivalents.

Claims

1. An aromatic amine compound, characterized in that The compound has the structure shown in formula (1): Among them, Ar 1 、Ar 2 are the same or different, each independently selected from hydrogen, substituted or unsubstituted C6-C60 aryl, or substituted or unsubstituted C6-C60 heteroaryl; L 1 -L 4 the same or different, each independently selected from a single bond, a substituted or unsubstituted C6-C60 arylene group, provided that L 1 , L 2 Not all are single bonds; R 1 -R 4 is selected from substituted or unsubstituted methyl; The substituents in the "substituted or unsubstituted" are each independently selected from one of deuterium, halogen, cyano, C1-C10 alkyl, C3-C10 cycloalkyl, C6-C30 aryl, C6-C30 aromatic ring group, C3-C30 heteroaryl, C3-C30 heteroaromatic ring group or a combination thereof, The heteroatoms of the heteroaryl group and heteroaromatic ring group are selected from one or more of oxygen, sulfur and nitrogen.

2. An aromatic amine compound according to claim 1, characterized in that The compound has a structure shown in formula (2) or formula (3): In formula (2) and formula (3), Ar 1 Selected from hydrogen, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C6-C60 heteroaryl; L 1 -L 4 the same or different, each independently selected from a single bond, a substituted or unsubstituted C6-C60 arylene group, provided that L 1 、L 2 Not all are single bonds; R 1 -R 4 is selected from substituted or unsubstituted methyl; The substituents in the "substituted or unsubstituted" are each independently selected from one of deuterium, halogen, cyano, C1-C10 alkyl, C3-C10 cycloalkyl, C6-C30 aryl, C6-C30 aromatic ring group, C3-C30 heteroaryl, C3-C30 heteroaromatic ring group or a combination thereof, The heteroatoms of the heteroaryl group and heteroaromatic ring group are selected from one or more of oxygen, sulfur and nitrogen.

3. An aromatic amine compound according to claim 1 or 2, characterized in that, The Ar 1 is selected from hydrogen, substituted or unsubstituted groups:

4. An aromatic amine compound according to claim 1 or 2, characterized in that, The L 1 -L 4 The same or different, each independently selected from a single bond, substituted or unsubstituted following groups: ， The condition is L 1 、L 2 Not single bond at the same time.

5. An aromatic amine compound according to claim 1 or 2, characterized in that, The L 3 is selected from a single bond, a phenylene group, and the L 1 , L 2 , L 4 Each independently selected from a single bond, a phenylene group, a biphenylene group, provided that L 1 , L 2 Not single bond at the same time.

6. An aromatic amine compound according to claim 1 or 2, characterized in that, The compound is selected from the following structures numbered 1-1 to 1-72, 2-1 to 2-72:

7. An organic electroluminescent element, characterized in that: The organic electroluminescent element comprises: A cathode, an anode, and one or more organic material layers disposed between the cathode and the anode, at least one of the organic material layers comprising the aromatic amine compound according to any one of claims 1 to 6.

8. The organic electroluminescent element according to claim 7, wherein The organic material layer includes a hole transport region, a light-emitting layer, and an electron transport region, wherein the hole transport region is located between the anode and the light-emitting layer, and the electron transport region is located between the light-emitting layer and the cathode; The hole transport region comprises the aromatic amine compound according to any one of claims 1 to 6.

9. The organic electroluminescent element according to claim 8, wherein The hole transport region comprises at least one layer selected from the group consisting of a hole injection layer, a hole transport layer, and a light-emitting auxiliary layer; The light-emitting auxiliary layer comprises the aromatic amine compound according to any one of claims 1 to 6.

10. An electronic device, characterized in that: The electronic device comprises one or more of a display, a monitor, and a lighting device, and the electronic device comprises the organic electroluminescent element according to any one of claims 7 to 9.

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