Aromatic amine compound and organic electroluminescent device containing aromatic amine compound

Abstract

The invention provides an aromatic amine 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. An aromatic amine compound is characterized in that the compound has a structure shown in a formula (1): # imgabs0 #, an organic electroluminescent element comprises a substrate, an anode, a hole transport region, a luminescent layer, an electron transport region and a cathode, the luminescent layer is located between the anode and the cathode, the hole transport region is located between the anode and the luminescent layer, and the electron transport region is located between the cathode and the luminescent layer. The electron transport region is located between the light-emitting layer and the cathode, and the hole transport region contains the compound provided by the invention. The organic electroluminescent element provided by the invention can realize the technical effects of high luminous efficiency, low driving voltage and long service life.

Description

Technical Field

[0001] The invention belongs to the technical field of photoelectric materials, and in particular relates to an aromatic amine compound and application of the compound in an organic electroluminescent device. 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, and is a technology suitable for flexible device devices (flexible light-emitting display devices). An organic electroluminescent device that utilizes the organic light-emitting phenomenon usually has a structure including an anode, a cathode, and an organic layer therebetween. In order to improve the efficiency and stability of the organic electroluminescent device, the organic layer is usually composed of a multilayer structure composed of various substances, including a cathode, an anode, and an organic layer placed therebetween. The organic layer is divided into a hole transport region, an electron transport region, and a light-emitting region according to different functions.

[0003] The hole transport region mainly plays the role of hole injection and transport, and can be subdivided into a hole injection layer and a hole transport layer. Hole transport materials used in the hole transport region should generally have high hole mobility, good thermal stability, good film-forming properties, and appropriate energy levels. Aromatic amine compounds are currently one of the most widely used hole transport materials in the OLED field. Since the properties of aromatic amine compounds with different structures are different, their specific applications are also different. For example, based on the differences in the hole injection ability and hole transport ability of aromatic amine compounds, the organic layers used for aromatic amine compounds with different structures are different. Some can be used in hole transport layers, some can be used in hole injection layers, and some can be used in multiple organic layers.

[0004] Many aromatic amine compounds can be used as hole transport materials in the hole transport layer. At present, although a large number of aromatic amine derivative materials with excellent performance have been developed, this technology still has many problems. How to design materials with better performance so that the device can achieve low voltage, high efficiency and long life is a major challenge facing OLED workers. Summary of the invention

[0005] The purpose of the present invention is to provide an aromatic amine compound and the application of the compound in an organic electroluminescent device, which can achieve the technical effects of high luminous efficiency, low driving voltage and long service life of the organic electroluminescent device.

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

[0007]

[0008] Wherein, X is selected from O, S, NR 2 ,

[0009] L 1 -L 2 Each is independently selected from a single bond, a substituted or unsubstituted C6-C60 arylene group, a substituted or unsubstituted C3-C60 heteroarylene group, and a substituted or unsubstituted C3-C20 cycloalkenylene group,

[0010] Ar 1- Ar 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 C2-C10 alkenyl, substituted or unsubstituted C3-C20 cycloalkenyl, substituted or unsubstituted C1-C10 alkoxy, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl,

[0011] The Ar 3 ,Ar 4 Each is independently connected to the benzene ring by a single bond or Ar 3 ,Ar 4 Each independently connects to the C at the adjacent position of the C to which it is connected to form a condensed ring,

[0012] R 1 -R 2 are each independently selected from hydrogen, substituted or unsubstituted C6-C60 aryl, and substituted or unsubstituted C3-C60 heteroaryl,

[0013] n is selected from 0 or 1,

[0014] The substituents in the "substituted or unsubstituted" are each independently selected from one or a combination of deuterium, halogen, cyano, C1-C10 alkyl, C3-C10 cycloalkyl, C6-C30 aryl, C3-C30 heteroaryl,

[0015] The heteroatom of the heteroaryl group is selected from one or more of oxygen, sulfur and nitrogen.

[0016] Preferably, X is selected from O or NR 2 .

[0017] Preferably, the compound has a structure shown in formula (2) or formula (3):

[0018]

[0019] More preferably, the compound has a structure shown in formula (4) to formula (7):

[0020]

[0021] Preferably, the L 1 -L 2 each independently selected from a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted anthrylene group, a substituted or unsubstituted phenanthrylene group, a substituted or unsubstituted fluoranthenylene group, a substituted or unsubstituted pyrenylene group, a substituted or unsubstituted perylene group, a substituted or unsubstituted triphenyl ... substituted or unsubstituted fluorenylene, substituted or unsubstituted 9,9-dimethylfluorenylene, substituted or unsubstituted 9,9-diphenylfluorenylene, substituted or unsubstituted spirobifluorenylene, substituted or unsubstituted dibenzofuranylene, substituted or unsubstituted dibenzothiophenylene, substituted or unsubstituted carbazolylene, substituted or unsubstituted benzonaphthofuranylene, substituted or unsubstituted benzonaphthothiophenylene, substituted or unsubstituted tetrahydropyrenylene.

[0022] As more preferably, the L 1 -L 2 Each is independently selected from a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted phenylene naphthyl group, a substituted or unsubstituted fluorenylene group, a substituted or unsubstituted 9,9-dimethylfluorenylene group, a substituted or unsubstituted 9,9-diphenylfluorenylene group, a substituted or unsubstituted spirobifluorenylene group, a substituted or unsubstituted dibenzofuranylene group, a substituted or unsubstituted dibenzothiophenylene group, a substituted or unsubstituted benzonaphthofuranylene group, and a substituted or unsubstituted tetrahydropyrenylene group.

[0023] Preferably, Ar 1 -Ar 4 each independently selected from hydrogen, substituted or unsubstituted methyl, substituted or unsubstituted tert-butyl, substituted or unsubstituted 1,3-butadienyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenylnaphthyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted fluoranthenyl, substituted or unsubstituted pyrenyl, substituted or unsubstituted peryl, substituted or unsubstituted triphenylene, substituted or unsubstituted substituted or unsubstituted fluorenyl, substituted or unsubstituted 9,9-dimethylfluorenyl, substituted or unsubstituted 9,9-diphenylfluorenyl, substituted or unsubstituted spirobifluorenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted benzonaphthofuranyl, substituted or unsubstituted benzonaphthothiophenyl, substituted or unsubstituted tetrahydropyrenyl.

[0024] As more preferably, the Ar 1 ,Ar 2 Each is independently selected from hydrogen, substituted or unsubstituted methyl, substituted or unsubstituted tert-butyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenylnaphthyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted 9,9-dimethylfluorenyl, substituted or unsubstituted 9,9-diphenylfluorenyl, substituted or unsubstituted spirobifluorenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted benzonaphthofuranyl, substituted or unsubstituted tetrahydropyrenyl.

[0025] As more preferably, the Ar 3 ,Ar 4 Each is independently selected from hydrogen, substituted or unsubstituted 1,3-butadienyl, and substituted or unsubstituted phenyl.

[0026] Preferably, the -L 1 -Ar 1 , -L 2 -Ar 2 Each is independently selected from the following substituted or unsubstituted groups:

[0027]

[0028]

[0029] in Indicates the connection site.

[0030] Preferably, the R 1 -R 2 Each is independently selected from hydrogen, substituted or unsubstituted phenyl, and substituted or unsubstituted biphenyl.

[0031] Most preferably, the R 1 Selected from hydrogen.

[0032] More preferably, the R 2 is selected from substituted or unsubstituted phenyl and substituted or unsubstituted biphenyl.

[0033] Preferably, the substituents in the "substituted or unsubstituted" are each independently selected from deuterium, halogen, cyano, methyl, ethyl, tert-butyl, cyclohexyl, phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthrenyl, pyrene, fluoranthenyl, triphenylene, A combination of one or more of dibenzothiophene, dibenzofuranyl and dibenzothiophene.

[0034] In a specific embodiment of the present invention, the aromatic amine compound is selected from any one of the following compounds Nos. 1-1 to 1-84, 2-1 to 2-84, 3-1 to 3-21:

[0035]

[0036]

[0037]

[0038]

[0039]

[0040]

[0041]

[0042]

[0043]

[0044]

[0045]

[0046]

[0047]

[0048] A use of the compound of the invention as an organic electroluminescent material.

[0049] An organic electroluminescent element comprises a substrate, an anode, a hole transport region, a light-emitting layer, an electron transport region, and a cathode, wherein the light-emitting layer is located between the anode and the cathode, the hole transport region is located between the anode and the light-emitting layer, the electron transport region is located between the light-emitting layer and the cathode, and the hole transport region contains the compound described in the present invention.

[0050] Preferably, the hole transport region comprises at least one of a hole injection layer and a hole transport layer, and the hole transport layer comprises the aromatic amine compound of the present invention.

[0051] An electronic device comprises: one or more of a display, a monitor and a lighting device, including the organic electroluminescent element of the present invention; and a control unit for driving the display device.

[0052] The beneficial effects of the present invention are:

[0053] The aromatic amine compound provided by the present invention can be used as a material for an organic material layer of an organic light-emitting device. The aromatic amine compound has good electron donation and high hole mobility, and has excellent hole transport efficiency and electron blocking ability. When used as a hole transport material in an organic electroluminescent device, the luminous efficiency of the device is improved, the life is extended, the driving voltage is reduced, and the device has more excellent comprehensive performance. BRIEF DESCRIPTION OF THE DRAWINGS

[0054] Figure 1 It is a schematic diagram of the structure 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. cathode. DETAILED DESCRIPTION

[0055] 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.

[0056] By reference to the following specific embodiments and the examples contained therein, the 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, because this can be varied. 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 in the present invention can be used in this practice or test, exemplary methods and materials are now described.

[0057] 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.

[0058] As used herein, the term "halogen" may include fluorine, chlorine, bromine or iodine.

[0059] 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.

[0060] 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, adamantyl, and the like.

[0061] As used in the present invention, the term "C3-C20 cycloalkenyl" refers to an unsaturated carbon ring derived from 3 to 20 carbon atoms, including monocyclic alkenyl, bicyclic alkenyl and condensed cyclic alkenyl, etc. Examples of such cycloalkenyl include, but are not limited to, cyclopropenyl, cyclobutadienyl, hydrophenanthrenyl, tetrahydropyrenyl, etc.

[0062] As used in the present invention, the term "cycloalkenylene" refers to a divalent cycloalkenyl group derived from a "cycloalkenyl" group by removing a hydrogen atom. For example, tetrahydropyrenyl is derived from tetrahydropyrenyl by removing a hydrogen atom.

[0063] 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.

[0064] 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.

[0065] 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.

[0066] 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.

[0067] 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.

[0068] 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.

[0069] As used in the present invention, the "carbon number is AA-BB" in the expression "Z group having carbon atoms AA-BB" or "Z group having C(AA-BB)" 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-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.

[0070] As used in the present invention, the term "single bond" refers to a direct connection of groups, for example, in formula (1), Medium 1 is a single bond, which means

[0071] As used in the present invention, "Ar 3 ,Ar 4 Each independently connects to the C at the adjacent position of the C to which it is connected to form a condensed ring", which means Ar 3 When selected from 1,3-butadienyl, the 1,3-butadienyl may be connected to the C at the adjacent position of the connected C to form a benzene ring such as As shown, where “—*” indicates the connection site; Ar 4 When selected from 1,3-butadienyl, the 1,3-butadienyl may be connected to the C at the adjacent position of the connected C to form a benzene ring such as As shown, where “-*” indicates the connection site.

[0072] 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,

[0073]

[0074] Indicates the position of substitution. "Unsubstituted" means that hydrogen atoms remain, in this case, hydrogen atoms include protium, deuterium, tritium.

[0075] As used herein, the term "phenylene naphthyl" refers to

[0076] As used herein, the term "phenylnaphthyl" includes

[0077] Refers to the replacement position.

[0078] When two or more substituents are present, the two or more substituents may be the same or different.

[0079] 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.

[0080] 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.

[0081] Organic electroluminescent element

[0082] 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.

[0083] 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.

[0084] 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.

[0085] As simple light emitting elements, the following may be cited, but are not limited thereto:

[0086] (1) hole transport layer / fluorescent light emitting layer / electron transport layer;

[0087] (2) hole transport layer / phosphorescent light emitting layer / electron transport layer;

[0088] (3) hole transport layer / first fluorescent light-emitting layer / second fluorescent light-emitting layer / electron transport layer;

[0089] (4) hole transport layer / first phosphorescent light-emitting layer / second phosphorescent light-emitting layer / electron transport layer;

[0090] (5) hole transport layer / fluorescent emitting layer / spacer layer / phosphorescent emitting layer / electron transport layer;

[0091] (6) hole transport layer / luminescence auxiliary layer / fluorescent light emitting layer / electron transport layer;

[0092] (7) hole transport layer / luminescence auxiliary layer / fluorescent light-emitting layer / hole blocking layer / electron transport layer;

[0093] (8) hole transport layer / luminescence auxiliary layer / phosphorescent light emitting layer / electron transport layer;

[0094] (9) hole transport layer / luminescence auxiliary layer / phosphorescent light emitting layer / hole blocking layer / electron transport layer;

[0095] (10) hole injection layer / hole transport layer / phosphorescent light emitting layer / electron transport layer / electron injection layer;

[0096] (11) hole injection layer / hole transport layer / fluorescent light emitting layer / electron transport layer / electron injection layer;

[0097] (12) hole injection layer / hole transport layer / luminescence auxiliary layer / phosphorescent light emitting layer / electron transport layer / electron injection layer;

[0099] (13) hole injection layer / hole transport layer / luminescence auxiliary 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, or the like may be used.

[0105] 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.

[0106] The hole injection layer is a layer that injects holes from the electrodes 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 other materials with hole transport ability can also be used.

[0107] The hole transport layer is a layer that receives holes from the hole injection layer and transports the holes to the light emitting layer, and the hole transport material 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.

[0108] 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, facilitate holes to enter the luminescent layer, and reduce the probability of electrons entering the hole transport region from the luminescent layer. Aromatic amine derivatives are commonly used.

[0109] 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.

[0110] 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. 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.

[0111] The electron injection layer is a layer that injects electrons from the electrode.

[0112] 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.

[0113] Synthesis formula: The following general formula is only one method for synthesizing the compounds of the present invention. The compounds of the present invention can also be synthesized by other methods.

[0114]

[0115] The same synthesis method can be used for different substitution positions, X, L 1 , L 2 , R 1 ,Ar 1 -Ar 4 The same meaning as in claim 1.

[0116] Compound Preparation Examples

[0117] The present invention is specifically described through Examples 1-29.

[0118] Example 1: Preparation of Compound 1-1

[0119]

[0120] Under a nitrogen atmosphere, 1-1-1 (77.0 g, 400.00 mmol), 1-1-2 (245.00 g, 120.00 mmol), copper powder (18.00 g, 280.00 mmol), potassium carbonate (111.00 g, 800.00 mmol) and 600 mL of nitrobenzene were mixed. After stirring at 200 °C for 12 hours, nitrobenzene was removed and the organic layer was separated with dichloromethane. The organic layer was purified by column chromatography to obtain compound 1-1-2 (90.00 g, yield 84%).

[0121] LC-MS (APCI) (M+H) + :268.67

[0122]

[0123] 1-1-3 (37.00 g, 139.00 mmol), palladium carbon (10%) (6.00 g) were mixed with a mixed solution of 500 mL methanol and 500 mL dichloromethane. Then, after stirring for about 15 hours under 60 psi of hydrogen, the solvent and catalyst were removed. The mixture was separated and purified by column chromatography to obtain compound 1-1-4 (35.20 g, yield 94%).

[0124] LC-MS (APCI) (M+H) + :269.86

[0125]

[0126] 1-1-4 (20.00 g, 74.30 mmol), N-bromosuccinimide (28.80 g, 162.00 mmol) and p-toluenesulfonic acid (4.30 g, 25.00 mmol) were added to a 300 mL reactor, and acetonitrile was added. After stirring at 50 °C for about 12 hours, it was cooled to room temperature, filtered and washed with methanol to obtain compound 1-1-5 (15.70 g, yield 61%).

[0127] LC-MS (APCI) (M+H) + :348.51

[0128]

[0129] Under a nitrogen atmosphere, compounds 1-1-5 (14.98 g, 43.00 mmol) and 1-1-6 (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 to dissolve, 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 1-1-7 (10.79 g, yield 66%).

[0130] LC-MS (APCI) (M+H) + :380.34

[0131]

[0132] Under nitrogen atmosphere, compound 1-1-7 (9.00 g, 23.64 mmol) and compound 1-1-8 (5.92 g, 28.36 mmol) were added to a three-necked flask, and a mixed solution of 150 mL tetrahydrofuran and 50 mL water was added to dissolve, and potassium carbonate (4.90 g, 35.46 mmol) and tetrakis (triphenylphosphine) palladium (0.55 g, 0.47 mmol) were added to reflux and stir for 3 hours. After the reaction was completed, the temperature was lowered, ethanol was added to the reaction solution, a solid was precipitated, and the precipitate was washed with pure water and ethanol in sequence. The solid was purified by column chromatography to obtain compound 1-1-9 (5.10 g, yield 39%).

[0133] LC-MS (APCI) (M+H) + :553.27

[0134]

[0135] Under a nitrogen atmosphere, compounds 1-1-9 (8.00 g, 14.49 mmol) and 1-1-10 (3.50 g, 15.03 mmol) were added to a three-necked flask, 50 mL of xylene was added, NaOt-Bu (1.67 g, 17.39 mmol), bis(tri-tert-butylphosphine)palladium(0) (0.15 g, 0.29 mmol) was added, and then heated and stirred for 4 hours, cooled to room temperature, filtered and concentrated, and recrystallized with 30 mL of ethyl acetate to obtain compound 1-1 (5.50 g, yield 54%).

[0136] LC-MS (APCI) (M+H) + :705.32

[0137] Example 2: Preparation of Compound 1-9

[0138]

[0139] Prepared according to the same synthesis method as in Example 1 above, replacing compound 1-1-6 with compound 1-9-6, compound 1-1-8 with compound 1-9-8, and compound 1-1-10 with compound 1-9-10, compound 1-9 (6.71 g, yield 56%, the yield being the synthesis yield of the reaction of 1-9-9 and 1-9-10) can be synthesized according to the above synthesis route.

[0140] LC-MS (APCI) (M+H) + :827.54

[0141] Example 3: Preparation of Compound 1-13

[0142]

[0143] Prepared according to the same synthesis method as in Example 1 above, replacing compound 1-1-10 with compound 1-13-10, compound 1-13 (7.54 g, 60% yield, which is the synthesis yield of the reaction of 1-1-9 and 1-13-10) can be synthesized according to the above synthesis route.

[0144] LC-MS (APCI) (M+H) + :867.52

[0145] Example 4: Preparation of Compound 1-19

[0146]

[0147] Prepared according to the same synthesis method as in Example 1 above, replacing compound 1-1-8 with compound 1-9-8, and compound 1-1-10 with compound 1-19-11, compound 1-19 (7.00 g, yield 55%, the yield being the synthesis yield of the reaction of 1-19-9 and 1-19-11) can be synthesized according to the above synthesis route.

[0148] LC-MS (APCI) (M+H) + :879.54

[0149] Example 5: Preparation of Compound 1-29

[0150]

[0151] Prepared according to the same synthesis method as in Example 1 above, replacing compound 1-1-8 with compound 1-29-8, and compound 1-1-10 with compound 1-29-10, compound 1-29 (7.90 g, yield 58%, the yield being the synthesis yield of the reaction of 1-29-9 and 1-29-10) can be synthesized according to the above synthesis route.

[0152] LC-MS (APCI) (M+H) + :939.78

[0153] Example 6: Preparation of Compound 1-32

[0154]

[0155] Prepared according to the same synthesis method as in Example 1 above, replacing compound 1-1-8 with compound 1-32-8, and compound 1-1-10 with compound 1-32-10, compound 1-32 (7.31 g, yield 60%, the yield being the synthesis yield of the reaction of 1-32-9 and 1-32-10) can be synthesized according to the above synthesis route.

[0156] LC-MS (APCI) (M+H) + :841.33

[0157] Example 7: Preparation of Compound 1-40

[0158]

[0159] Prepared according to the same synthesis method as in Example 1 above, replacing compound 1-1-8 with compound 1-40-8, and compound 1-1-10 with compound 1-40-10, compound 1-40 (6.20 g, yield 57%, the yield being the synthesis yield of the reaction of 1-40-9 and 1-40-10) can be synthesized according to the above synthesis route.

[0160] LC-MS (APCI) (M+H) + :843.19

[0161] Example 8: Preparation of Compound 1-45

[0162]

[0163] Prepared according to the same synthesis method as in Example 1 above, replacing compound 1-1-2 with compound 1-45-2, compound 1-1-8 with compound 1-29-8, and compound 1-1-10 with compound 1-45-10, compound 1-45 (7.00 g, yield 57%, the yield being the synthesis yield of the reaction of 1-45-9 and 1-45-10) can be synthesized according to the above synthesis route.

[0164] LC-MS (APCI) (M+H) + :847.68

[0165] Example 9: Preparation of Compound 1-52

[0166]

[0167] Prepared according to the same synthesis method as in Example 8 above, replacing compound 1-1-8 with compound 1-52-8, and compound 1-1-10 with compound 1-52-10, compound 1-52 (8.00 g, yield 60%, the yield being the synthesis yield of the reaction of 1-52-9 and 1-52-10) can be synthesized according to the above synthesis route.

[0168] LC-MS (APCI) (M+H) + :920.98

[0169] Example 10: Preparation of Compound 1-59

[0170]

[0171] Prepared according to the same synthesis method as in Example 7 above, replacing compound 1-40-10 with compound 1-59-10, compound 1-59 (6.13 g, 58% yield, which is the synthesis yield of the reaction of 1-40-9 and 1-59-10) can be synthesized according to the above synthesis route.

[0172] LC-MS (APCI) (M+H) + :729.13

[0173] Example 11: Preparation of Compound 1-64

[0174]

[0175] Prepared according to the same synthesis method as in Example 5 above, replacing compound 1-19-10 with compound 1-40-10, compound 1-64 (5.55 g, yield 58%, the yield being the synthesis yield of the reaction of 1-19-9 and 1-40-10) can be synthesized according to the above synthesis route.

[0176] LC-MS (APCI) (M+H) + :828.99

[0177] Example 12: Preparation of Compound 1-73

[0178]

[0179] Prepared according to the same synthesis method as in Example 2 above, replacing compound 1-9-8 with compound 1-73-8, and compound 1-9-10 with compound 1-40-10, compound 1-73 (6.97 g, 56% yield, which is the synthesis yield of the reaction of 1-73-9 and 1-40-10) can be synthesized according to the above synthesis route.

[0180] LC-MS (APCI) (M+H) + :860.11

[0181] Example 13: Preparation of Compound 1-76

[0182]

[0183] Prepared according to the same synthesis method as in Example 2 above, replacing compound 1-9-8 with compound 1-76-8, and compound 1-9-10 with compound 1-76-10, compound 1-76 (7.17 g, 55% yield, which is the synthesis yield of the reaction of 1-76-9 and 1-76-10) can be synthesized according to the above synthesis route.

[0184] LC-MS (APCI) (M+H) + :893.47

[0185] Example 14: Preparation of Compound 1-82

[0186]

[0187] Prepared according to the same synthesis method as in Example 1 above, replacing compound 1-1-8 with compound 1-76-8, and compound 1-1-10 with compound 1-52-10, compound 1-82 (7.86 g, yield 59%, the yield being the synthesis yield of the reaction of 1-76-9 and 1-52-10) can be synthesized according to the above synthesis route.

[0188] LC-MS (APCI) (M+H) + :919.45

[0189] Example 15: Preparation of Compound 2-1

[0190]

[0191] 2-1-2 (16.70 g, 61.85 mmol) was dissolved in 250 mL of ethyl acetate, and then Raney nickel (10 g) was added and reacted at room temperature for 48 hours. After the reaction was completed, a diatomaceous earth column was used to remove the catalyst, pd / C (5 g) catalyst was added, and hydrogen reaction was performed again at room temperature under a hydrogen pressure of about 100 psi for 72 hours. After the reaction was completed, the solvent was removed under reduced pressure, and compound 2-1-3 (14.80 g, 88% yield) was obtained by column chromatography.

[0192] LC-MS (APCI) (M+H) + :272.76

[0193]

[0194] Under a nitrogen atmosphere, compounds 2-1-3 (14.8 g, 54.39 mmol) and 1-1-6 (9.30 g, 59.62 mmol) were added to a three-necked flask, and a mixed solution of 70 mL of toluene, 30 mL of ethanol and 30 mL of water was added, followed by potassium carbonate (11.61 g, 84.16 mmol) and tetrakistriphenylphosphine palladium (0) (0.97 g, 0.84 mmol). After heating and stirring for 3 hours, the mixture was cooled to room temperature, washed with water, and the organic layer was concentrated and purified by column chromatography to obtain compound 2-1-4 (13.26 g, yield 80%).

[0195] LC-MS (APCI) (M+H) + :305.12

[0196]

[0197] Compounds 2-1-4 (13.20 g, 43.28 mmol) and 1-29-8 (7.33 g, 43.37 mmol) were completely dissolved in 200 mL of xylene, and NaOt-Bu (8.34 g, 86.87 mmol) and bis(tri-tert-butylphosphine)palladium(0) (0.32 g, 0.63 mmol) were added. After heating and stirring for 3 hours, the mixture was cooled to room temperature and extracted with distilled water and ethyl acetate. The organic layer was purified by MgSO 4 The residue was dried, filtered and concentrated. Using ethyl acetate and hexane as developing solvents, column chromatography was performed to obtain compound 2-1-5 (12.13 g, yield 64%).

[0198] LC-MS (APCI) (M+H) + :437.63

[0199]

[0200] After 2-1-5 (18.95 g, 43.36 mmol) and 2.1-6 (11.83 g, 43.33 mmol) were completely dissolved in 200 mL of xylene, NaOt-Bu (8.34 g, 86.87 mmol) was added, and bis(tri-tert-butylphosphine)palladium(0) (0.32 g, 0.63 mmol) was added. After heating and stirring for 3 hours, the mixture was cooled to room temperature and extracted with distilled water and ethyl acetate. The organic layer was purified by MgSO 4 The residue was dried, filtered and concentrated. Using ethyl acetate and hexane as developing solvents, the compound 2-1 (19.66 g, yield 72%) was obtained by column chromatography.

[0201] LC-MS (APCI) (M+H) + :630.17

[0202] Example 16: Synthesis of Compound 2-5

[0203]

[0204] Prepared according to the same synthesis method as in Example 15 above, replacing compound 1-29-8 with compound 2-1-5, and compound 2-1-6 with compound 1-13-10, compound 2-5 (26.08 g, yield 80%, the yield being the synthesis yield of the reaction of 2-5-6 and 1-13-10) can be synthesized according to the above synthesis route.

[0205] LC-MS (APCI) (M+H) + :752.25

[0206] Example 17: Preparation of Compound 2-15

[0207]

[0208] Prepared according to the same synthesis method as in Example 15 above, replacing compound 1-1-6 with compound 2-15-4, compound 1-29-8 with compound 1-1-8, and compound 2-1-6 with compound 1-13-10, compound 2-15 (28.50 g, yield 83%, the yield being the synthesis yield of the reaction of 2-15-6 and 1-13-10) can be synthesized according to the above synthesis route.

[0209] LC-MS (APCI) (M+H) + :751.95

[0210] Example 18: Preparation of Compound 2-23

[0211]

[0212] Prepared according to the same synthesis method as in Example 15 above, replacing compound 2-1-6 with compound 2-23-1, compound 2-23 (25.12 g, yield 70%, the yield being the synthesis yield of the reaction of 2-1-5 and 2-23-1) can be synthesized according to the above synthesis route.

[0213] LC-MS (APCI) (M+H) + :828.33

[0214] Example 19: Preparation of Compound 2-32

[0215]

[0216] Prepared according to the same synthesis method as in Example 15 above, replacing compound 1-29-8 with compound 1-32-8, and compound 2-1-6 with compound 1-32-10, compound 2-32 (24.34 g, 73% yield, which is the synthesis yield of the reaction of 2-32-5 and 1-32-10) can be synthesized according to the above synthesis route.

[0217] LC-MS (APCI) (M+H) + :766.08

[0218] Example 20: Preparation of Compound 2-41

[0219]

[0220] Prepared according to the same synthesis method as in Example 19 above, replacing compound 1-32-10 with compound 1-40-10, compound 2-41 (25.49 g, yield 77%, the yield being the synthesis yield of the reaction of 2-32-5 and 1-40-10) can be synthesized according to the above synthesis route.

[0221] LC-MS (APCI) (M+H) + :768.11

[0222] Example 21: Preparation of Compound 2-47

[0223]

[0224] Prepared according to the same synthesis method as in Example 15 above, replacing compound 1-29-8 with compound 2-47-1, and compound 2-1-6 with compound 1-19-11, compound 2-47 (24.31 g, yield 76%, the yield being the synthesis yield of the reaction of 2-47-2 and 1-19-11) can be synthesized according to the above synthesis route.

[0225] LC-MS (APCI) (M+H) + :732.20

[0226] Example 22: Preparation of Compound 2-53

[0227]

[0228] Prepared according to the same synthesis method as the above-mentioned Example 21, replacing compound 1-19-11 with compound 1-52-10, compound 2-53 (24.33 g, yield 73%, the yield is the synthesis yield of the reaction of 2-47-2 and 1-53-1) can be synthesized according to the above-mentioned synthesis route.

[0229] LC-MS (APCI) (M+H) + :770.18

[0230] Example 23: Preparation of Compound 2-60

[0231]

[0232] Prepared according to the same synthesis method as in Example 15 above, replacing compound 1-29-8 with compound 2-60-1, and compound 2-1-6 with compound 2-60-3, compound 2-60 (21.80 g, yield 77%, the yield being the synthesis yield of the reaction of 2-60-2 and 2-60-3) can be synthesized according to the above synthesis route.

[0233] LC-MS (APCI) (M+H) + :654.09

[0234] Example 24: Preparation of Compound 2-65

[0235]

[0236] Prepared according to the same synthesis method as the above-mentioned Example 16, replacing compound 1-13-10 with compound 1-40-10, compound 2-65 (26.42 g, yield 81%, the yield is the synthesis yield of the reaction of 2-65-2 and 1-40-10) can be synthesized according to the above-mentioned synthesis route.

[0237] LC-MS (APCI) (M+H) + :754.11

[0238] Example 25: Preparation of Compound 2-72

[0239]

[0240] Prepared according to the same synthesis method as in Example 15 above, replacing compound 1-1-6 with compound 1-9-6, compound 1-29-8 with compound 2-72-2, and compound 2-1-6 with compound 1-40-10, compound 2-72 (25.94 g, yield 78%, the yield being the synthesis yield of the reaction of 2-72-2 and 1-40-10) can be synthesized according to the above synthesis route.

[0241] LC-MS (APCI) (M+H) + :768.28

[0242] Example 26: Preparation of Compound 2-77

[0243]

[0244] Prepared according to the same synthesis method as in Example 25 above, replacing compound 2-27-2 with compound 1-76-8, and compound 2-1-6 with compound 1-76-10, compound 2-77 (26.57 g, 75% yield, which is the synthesis yield of the reaction of 2-77-1 and 1-76-10) can be synthesized according to the above synthesis route.

[0245] LC-MS (APCI) (M+H) + :818.32

[0246] Example 27: Preparation of Compound 2-83

[0247]

[0248] Prepared according to the same synthesis method as in Example 15 above, replacing compound 1-29-8 with compound 2-83-1, and compound 2-1-6 with compound 1-40-10, compound 2-83 (28.32 g, yield 76%, the yield being the synthesis yield of the reaction of 2-83-2 and 1-40-10) can be synthesized according to the above synthesis route.

[0249] LC-MS (APCI) (M+H) + :860.47

[0250] Example 28: Preparation of Compound 3-2

[0251]

[0252] Prepared according to the same synthesis method as in Example 1 above, replacing compound 1-1-6 with compound 3-2-1, compound 1-1-8 with compound 1-29-8, and compound 1-1-10 with compound 3-2-4, compound 3-2 (5.82 g, yield 53%, which is the synthesis yield of the reaction of 3-2-3 and 3-2-4) can be synthesized according to the above synthesis route.

[0253] LC-MS (APCI) (M+H) + :755.28

[0254] Example 29: Preparation of Compound 3-17

[0255]

[0256] Prepared according to the same synthesis method as in Example 15 above, replacing compound 1-1-6 with compound 3-17-4, and compound 2-1-6 with compound 3-17-7, compound 3-17 (26.14 g, yield 76%, which is the synthesis yield of the reaction of 3-17-3 and 3-17-4) can be synthesized according to the above synthesis route.

[0257] LC-MS (APCI) (M+H) + :792.26

[0258] Device Preparation Example

[0259] Application Example 1 illustrates the application effect of the compound of the present invention as a hole transport layer in a device.

[0260] Application Example 1

[0261] 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 and 7, a cathode, which are stacked from bottom to top.

[0262] The specific device structure is:

[0263] ITO / HATCN(5nm) / HT(60nm) / EB(5nm) / BH+BD(3wt%)(20nm) / ET(15nm) / Al(100nm).

[0264] Device preparation process:

[0265] HATCN was evaporated on the ITO substrate to form a A hole injection layer (HIL) is formed by evaporating HT on the hole injection layer to form a layer with a thickness of A hole transport layer (HTL) is formed by evaporating BP on the hole transport layer to form a layer with a thickness of The light-emitting auxiliary layer (EBL) is formed by evaporating BH+BD (3 wt %) on the light-emitting auxiliary layer to form a layer with a thickness of The light-emitting layer (EML) is deposited in the following order: The electron transport layer (ETL) of ) to form a cathode, thereby manufacturing an organic electroluminescent device. This is recorded as Comparative Example 1.

[0266]

[0267] Device Comparison Example 2

[0268] The hole transport layer 3 was prepared by using HT-1 instead of HT material, and the organic electroluminescent device was prepared by the same method as the embodiment of the comparative example 1 above.

[0269] Device Comparison Example 3

[0270] The hole transport layer 3 was prepared by using HT-2 instead of HT material, and the organic electroluminescent device was prepared by the same method as the embodiment of the comparative example 1 above.

[0271] Device Comparison Example 4

[0272] The hole transport layer 3 was prepared by using HT-3 instead of HT material, and the organic electroluminescent device was prepared by the same method as the embodiment of the comparative example 1 above.

[0273] Device Example 1

[0274] The hole transport layer 3 was prepared by using compound 1-1 instead of HT material, and the organic electroluminescent device was prepared by the same method as that of the embodiment of Comparative Example 1.

[0275] Device Example 2

[0276] The hole transport layer 3 was prepared by using compound 1-9 instead of HT material, and the organic electroluminescent device was prepared by the same method as the embodiment of the comparative example 1 above.

[0277] Device Example 3

[0278] The hole transport layer 3 was prepared by using compound 1-13 instead of HT material, and the organic electroluminescent device was prepared by the same method as the embodiment of the comparative example 1 above.

[0279] Device Example 4

[0280] The hole transport layer 3 was prepared by using compound 1-19 instead of HT material, and the organic electroluminescent device was prepared by the same method as the embodiment of the comparative example 1 above.

[0281] Device Example 5

[0282] The hole transport layer 3 was prepared by using compound 1-29 instead of HT material, and the organic electroluminescent device was prepared by the same method as that of the embodiment of Comparative Example 1 above.

[0283] Device Example 6

[0284] The hole transport layer 3 was prepared by using compound 1-32 instead of HT material, and the organic electroluminescent device was prepared by the same method as that of the embodiment of Comparative Example 1 above.

[0285] Device Example 7

[0286] The hole transport layer 3 was prepared by using compound 1-40 instead of HT material, and the organic electroluminescent device was prepared by the same method as that of the embodiment of Comparative Example 1 above.

[0287] Device Example 8

[0288] The hole transport layer 3 was prepared by using compound 1-45 instead of HT material, and the organic electroluminescent device was prepared by the same method as that of the embodiment of Comparative Example 1 above.

[0289] Device Example 9

[0290] The hole transport layer 3 was prepared by using compound 1-52 instead of HT material, and the organic electroluminescent device was prepared by the same method as that of the embodiment of Comparative Example 1 above.

[0291] Device Example 10

[0292] The hole transport layer 3 was prepared by using compound 1-59 instead of HT material, and the organic electroluminescent device was prepared by the same method as that of the embodiment of Comparative Example 1 above.

[0293] Device Example 11

[0294] The hole transport layer 3 was prepared by using compound 1-64 instead of HT material, and the organic electroluminescent device was prepared by the same method as that of the embodiment of Comparative Example 1 above.

[0295] Device Example 12

[0296] The hole transport layer 3 was prepared by using compound 1-73 instead of HT material, and the organic electroluminescent device was prepared by the same method as the implementation scheme of the above-mentioned comparative example 1.

[0297] Device Example 13

[0298] The hole transport layer 3 was prepared by using compound 1-76 instead of HT material, and the organic electroluminescent device was prepared by the same method as that of the embodiment of Comparative Example 1 above.

[0299] Device Example 14

[0300] The hole transport layer 3 was prepared by using compound 1-82 instead of HT material, and the organic electroluminescent device was prepared by the same method as the implementation scheme of the above-mentioned comparative example 1.

[0301] Device Example 15

[0302] The hole transport layer 3 was prepared by using compound 2-1 instead of HT material, and the organic electroluminescent device was prepared by the same method as that of the embodiment of Comparative Example 1.

[0303] Device Example 16

[0304] The hole transport layer 3 was prepared by using compound 2-5 instead of HT material, and the organic electroluminescent device was prepared by the same method as that of the embodiment of Comparative Example 1.

[0305] Device Example 17

[0306] The hole transport layer 3 was prepared by using compound 2-15 instead of HT material, and the organic electroluminescent device was prepared by the same method as that of the embodiment of Comparative Example 1 above.

[0307] Device Example 18

[0308] The hole transport layer 3 was prepared by using compound 2-23 instead of HT material, and the organic electroluminescent device was prepared by the same method as that of the embodiment of Comparative Example 1 above.

[0309] Device Example 19

[0310] The hole transport layer 3 was prepared by using compound 2-32 instead of HT material, and the organic electroluminescent device was prepared by the same method as that of the embodiment of Comparative Example 1 above.

[0311] Device Example 20

[0312] The hole transport layer 3 was prepared by using compound 2-41 instead of HT material, and the organic electroluminescent device was prepared by the same method as that of the embodiment of Comparative Example 1 above.

[0313] Device Example 21

[0314] The hole transport layer 3 was prepared by using compound 2-47 instead of HT material, and the organic electroluminescent device was prepared by the same method as that of the embodiment of Comparative Example 1 above.

[0315] Device Example 22

[0316] The hole transport layer 3 was prepared by using compound 2-53 instead of HT material, and the organic electroluminescent device was prepared by the same method as that of the embodiment of Comparative Example 1.

[0317] Device Example 23

[0318] The hole transport layer 3 was prepared by using compound 2-60 instead of HT material, and the organic electroluminescent device was prepared by the same method as that of the embodiment of Comparative Example 1 above.

[0319] Device Example 24

[0320] The hole transport layer 3 was prepared by using compound 2-65 instead of HT material, and the organic electroluminescent device was prepared by the same method as that of the embodiment of Comparative Example 1 above.

[0321] Device Example 25

[0322] The hole transport layer 3 was prepared by using compound 2-72 instead of HT material, and the organic electroluminescent device was prepared by the same method as that of the embodiment of Comparative Example 1 above.

[0323] Device Example 26

[0324] The hole transport layer 3 was prepared by using compound 2-77 instead of HT material, and the organic electroluminescent device was prepared by the same method as the implementation scheme of the above-mentioned comparative example 1.

[0325] Device Example 27

[0326] The hole transport layer 3 was prepared by using compound 2-83 instead of HT material, and the organic electroluminescent device was prepared by the same method as the implementation scheme of the above-mentioned comparative example 1.

[0327] Device Example 28

[0328] The hole transport layer 3 was prepared by using compound 3-2 instead of HT material, and the organic electroluminescent device was prepared by the same method as that of the embodiment of Comparative Example 1.

[0329] Device Example 29

[0330] The hole transport layer 3 was prepared by using compound 3-17 instead of HT material, and the organic electroluminescent device was prepared by the same method as the implementation scheme of Comparative Example 1 above.

[0331] Test Results

[0332] 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 taken as 100%, and the relative life values ​​of each Comparative Example and Example were obtained.

[0333] 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 embodiments.

[0334] Current efficiency at current density 15mA / cm 2The following test was conducted, with the current efficiency of Comparative Example 1 being 100%, to obtain the relative values ​​of the current efficiency of each Comparative Example and the Example. The test results are shown in Table 1.

[0335] Table 1

[0336]

[0337]

[0338] From the results shown in Table 1 above, it can be seen that compared with the comparative example, the aromatic amine compound of the present invention is used in the hole transport layer, the driving voltage is reduced, the luminous efficiency and life are improved, and the performance of the organic electroluminescent device is significantly improved. Therefore, the compound of the present invention is suitable for use as a hole transport layer material.

[0339] 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.

Claims

1. An aromatic amine compound, Features The compound has the structure shown in formula (1): Wherein, X is selected from O, S, NR 2 , L 1 -L 2 Each is independently selected from a single bond, a substituted or unsubstituted C6-C60 arylene group, a substituted or unsubstituted C3-C60 heteroarylene group, and a substituted or unsubstituted C3-C20 cycloalkenylene group, Ar 1- Ar 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 C2-C10 alkenyl, substituted or unsubstituted C3-C20 cycloalkenyl, substituted or unsubstituted C1-C10 alkoxy, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl, The Ar 3 ,Ar 4 Each is independently connected to the benzene ring by a single bond or Ar 3 ,Ar 4 Each independently connects to the C at the adjacent position of the C to which it is connected to form a condensed ring, R 1 -R 2 are each independently selected from hydrogen, substituted or unsubstituted C6-C60 aryl, and substituted or unsubstituted C3-C60 heteroaryl, n is selected from 0 or 1, The substituents in the "substituted or unsubstituted" are independently selected from one or a combination of deuterium, halogen, cyano, C1-C10 alkyl, C3-C10 cycloalkyl, C6-C30 aryl, C3-C30 heteroaryl, and the heteroatom of the heteroaryl is selected from one or more of oxygen, sulfur and nitrogen.

2. The aromatic amine compound according to claim 1, Features: The compound has the structure shown in formula (2) and formula (3):

3. The aromatic amine compound according to claim 1, Features: The L 1 -L 2 each independently selected from a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted anthrylene group, a substituted or unsubstituted phenanthrylene group, a substituted or unsubstituted fluoranthenylene group, a substituted or unsubstituted pyrenylene group, a substituted or unsubstituted perylene group, a substituted or unsubstituted triphenyl ... pyrenylene group, a substituted or unsubstituted pyrenylene group, a substituted or unsubstituted fluorenylene, substituted or unsubstituted 9,9-dimethylfluorenylene, substituted or unsubstituted 9,9-diphenylfluorenylene, substituted or unsubstituted spirobifluorenylene, substituted or unsubstituted dibenzofuranylene, substituted or unsubstituted dibenzothiophenylene, substituted or unsubstituted carbazolylene, substituted or unsubstituted benzonaphthofuranylene, substituted or unsubstituted benzonaphthothiophenylene, substituted or unsubstituted tetrahydropyrenylene.

4. The aromatic amine compound according to claim 1, Features: The Ar 1 -Ar 4 each independently selected from hydrogen, substituted or unsubstituted methyl, substituted or unsubstituted tert-butyl, substituted or unsubstituted 1,3-butadienyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenylnaphthyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted fluoranthenyl, substituted or unsubstituted pyrenyl, substituted or unsubstituted peryl, substituted or unsubstituted triphenylene, substituted or unsubstituted substituted or unsubstituted fluorenyl, substituted or unsubstituted 9,9-dimethylfluorenyl, substituted or unsubstituted 9,9-diphenylfluorenyl, substituted or unsubstituted spirobifluorenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted benzonaphthofuranyl, substituted or unsubstituted benzonaphthothiophenyl, substituted or unsubstituted tetrahydropyrenyl.

5. The aromatic amine compound according to claim 1, Features: The R 1 -R 2 Each is independently selected from hydrogen, substituted or unsubstituted phenyl, and substituted or unsubstituted biphenyl.

6. The aromatic amine compound according to claim 1, Features The compound is selected from any one of the following compounds Nos. 1-1 to 1-84, 2-1 to 2-84, 3-1 to 3-21:

7. Use of the compound according to claims 1 to 6 as an organic electroluminescent material.

8. An organic electroluminescent element comprising a substrate, an anode, a hole transport region, a light emitting layer, an electron transport region, and a cathode, Features: The light-emitting layer is located between the anode and the cathode, 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 contains the compound according to claims 1-6.

9. The organic electroluminescent element according to claim 8, Features: The hole transport region comprises at least one of a hole injection layer and a hole transport layer; The hole transport layer comprises the aromatic amine compound according to any one of claims 1 to 6.

10. An electronic device, include: One or more of a display, a monitor, and a lighting device, comprising the organic electroluminescent element according to claim 8 or 9; and a control unit for driving the display device.

Images