Organic compound and application thereof

Abstract

According to the organic compound and the application thereof, the organic compound serves as an organic electroluminescent material, and an organic electroluminescent device can have low driving voltage, high current efficiency and long service life.

Description

Technical Field

[0001] The invention belongs to the technical field of organic electroluminescent materials and relates to an organic compound and application thereof. Background Art

[0002] Organic light-emitting diodes (OLEDs) that utilize organic light-emitting diodes (OLEDs) have the characteristics of wide viewing angle, excellent contrast, fast response time, excellent brightness, driving voltage, and response speed. Therefore, research on organic electroluminescent devices has been rapidly developed and commercialized.

[0003] Organic electroluminescent devices (OLEDs) convert electrical energy into light by applying power to organic electroluminescent materials, and generally include an anode, a cathode, and an organic layer formed between the two electrodes. The organic layer of the organic electroluminescent device may include a hole injection layer, a hole transport layer, a hole auxiliary layer, a luminescent auxiliary layer, an electron blocking layer, a luminescent layer (containing a host material and a dopant material), an electron buffer layer, a hole blocking layer, an electron transport layer, an electron injection layer, etc. The materials used in the organic layer can be divided into hole injection materials, hole transport materials, hole auxiliary materials, luminescent auxiliary materials, electron blocking materials, luminescent materials, electron buffer materials, hole blocking materials, electron transport materials, electron injection materials, etc. according to their functions. In an organic electroluminescent device, holes from the anode and electrons from the cathode are injected into the luminescent layer by applying a voltage, and excitons with high energy are generated by the recombination of holes and electrons. The organic light-emitting compound moves to an excited state by energy and emits light by the energy when the organic light-emitting compound returns to the ground state from the excited state.

[0004] At present, the low luminous efficiency and short life of organic light-emitting diodes are seriously restricted by the low stability of organic functional materials and unbalanced carrier mobility, which requires the continuous development of organic light-emitting devices with improved driving voltage, luminous efficiency and life. Summary of the invention

[0005] In view of the deficiencies in the prior art, the present invention aims to provide an organic compound and application thereof.

[0006] In order to achieve the purpose of the invention, the present invention adopts the following technical solutions:

[0007] In one aspect, the present invention provides an organic compound having a structure as shown in Formula 1

[0008]

[0009] Among them, R 3 -R 10One of them and R in the structure shown in formula 2 11 -R 14 Connect any one of them,

[0010] X is selected from O or S; X1 is selected from O or S; X2 is selected from C or N;

[0011] R 3 -R 10 Any one of the groups not connected to Formula 2 is connected to the structure shown in Formula 3,

[0012] in is the connection site,

[0013] R 3 -R 10 The groups not connected to Formula 2 or Formula 3 are independently selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl or substituted or unsubstituted C3-C30 cycloalkyl,

[0014] R 11 -R 14 The groups not connected to Formula 1 are each independently selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl or substituted or unsubstituted C3-C30 cycloalkyl,

[0015] R 1 , R 2 Each is independently selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C30 alkyl, a group obtained by replacing one or at least two methylene groups in the substituted or unsubstituted C1-C30 alkyl with -O- or -S- in a non-adjacent O atom or S atom, a substituted or unsubstituted C2-C30 alkenyl, a group obtained by replacing one or at least two methylene groups in the substituted or unsubstituted C2-C30 alkenyl with -O- or -S- in a non-adjacent O atom or S atom, a substituted or unsubstituted C7-C30 aralkyl, a substituted or unsubstituted C6-C30 aryl, a substituted or unsubstituted C3-C30 heteroaryl, a substituted or unsubstituted C4-C30 heteroaralkyl, a substituted or unsubstituted C3-C30 cycloalkyl, a substituted or unsubstituted C3-C30 heterocycloalkyl, and a substituted or unsubstituted C3-C30 cycloalkenyl.

[0016] Due to its structural characteristics, the organic compound of the present invention can enable an organic electroluminescent device using the organic compound as a light-emitting material to have a low driving voltage, a high current efficiency and a long lifespan.

[0017] In the present invention, Formula 2 can also be expressed as

[0018] Preferably, R 3 -R 10 The groups not connected to Formula 2 or Formula 3 are each independently selected from hydrogen or deuterium.

[0019] Preferably, R 11 -R 14 The groups not connected to Formula 1 are each independently selected from hydrogen or deuterium.

[0020] Preferably, R 1 , R 2 Each independently selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, anthracenyl, phenyl substituted naphthyl, naphthyl substituted phenyl, pyridyl, pyridyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl (including ), dimethylfluorenyl (preferably selected from ), diphenylfluorenyl (preferably selected from ), spirobifluorenyl, dibenzofuranyl substituted phenyl, dibenzothiophene substituted phenyl, dimethylfluorenyl substituted phenyl, benzocarbazolyl, benzonaphthofuranyl or benzonaphthothiophene.

[0021] Preferably, the substituted substituents are each independently selected from any one or a combination of at least two of deuterium, halogen, cyano, C1-C30 straight or branched alkyl, C3-C30 cycloalkyl, C6-C60 aryl or C3-C60 heteroaryl.

[0022] Preferably, the substituted substituents are each independently selected from any one or a combination of at least two of deuterium, halogen, cyano, methyl, phenyl, naphthyl, dibenzofuranyl, dibenzothienyl or dimethylfluorenyl.

[0023] Preferably, R 7 With R 11 -R 14 Any connection;

[0024] Preferably, R 8 -R 10 Any one of them is connected with Formula 3;

[0025] More preferably, R 7 With R 13 connect;

[0026] More preferably, R 9 Connect with formula 3;

[0027] Preferably, R 8 With R 11 -R 14Any connection;

[0028] Preferably, R 7 , R 9 -R 10 Any one of them is connected with Formula 3;

[0029] More preferably, R 8 With R 13 connect;

[0030] Preferably, R 9 With R 11 -R 14 Any connection;

[0031] Preferably, R 7 -R 8 , R 10 Any one of them is connected with Formula 3;

[0032] More preferably, R 9 With R 13 connect;

[0033] More preferably, R 7 Connect with formula 3;

[0034] Preferably, R 10 With R 11 -R 14 Any connection;

[0035] Preferably, R 7 -R 9 Any one of them is connected with Formula 3;

[0036] More preferably, R 10 With R 13 connect.

[0037] Preferably, the compound is selected from any one of the following compounds:

[0038]

[0039]

[0040]

[0041]

[0042]

[0043]

[0044]

[0045]

[0046]

[0047]

[0048]

[0049]

[0050]

[0051]

[0052] In the present invention, the synthesis path of the organic compound as described above comprises the following steps:

[0053] 1. Synthesis of:

[0054] It is prepared by Suzuki coupling reaction of starting material A and starting material B. The general synthesis formula is as follows:

[0055]

[0056] 2. Synthesis of:

[0057] The first step is to prepare the synthesis formula of intermediate C as follows:

[0058]

[0059] In the second step, the starting material A and the starting material C are subjected to Suzuki coupling reaction to obtain the product. The general synthesis formula is as follows:

[0060]

[0061] 3. Synthesis of:

[0062] The first step is to prepare the general synthesis formula of intermediate D as follows:

[0063]

[0064] In the second step, the starting material A and the intermediate D are subjected to a Suzuki coupling reaction to obtain the product. The general synthesis formula is as follows:

[0065]

[0066] In another aspect, the present invention provides an organic electroluminescent material, which comprises the organic compound as described above.

[0067] In another aspect, the present invention provides an organic electroluminescent device, comprising a first electrode, a second electrode, and an organic layer disposed between the first electrode and the second electrode, wherein a material of the organic layer comprises at least one of the organic compounds described above.

[0068] Preferably, the organic layer comprises at least one of a hole injection layer, a first hole transport layer, a second hole transport layer, an electron blocking layer, a light emitting layer, an electron buffer layer, an electron transport layer or an electron injection layer.

[0069] Preferably, the organic layer comprises an electron buffer layer, and the electron buffer layer comprises at least one of the organic compounds described above.

[0070] Preferably, the organic layer comprises an electron transport layer, and the electron transport layer comprises at least one of the organic compounds described above.

[0071] Preferably, the organic layer comprises a light-emitting layer, and the light-emitting layer comprises at least one of the organic compounds described above.

[0072] Preferably, the light-emitting layer further comprises an iridium-containing complex.

[0073] In another aspect, the present invention provides a product comprising the organic electroluminescent device as described above.

[0074] Preferably, the product is used in optoelectronics, medicine, biotechnology, optical fiber, lighting equipment, electronic photographic photoreceptor, photoelectric converter, organic solar cell, switching element, organic light emitting field effect transistor, image sensor or dye laser.

[0075] The term "organic electroluminescent material" in the present invention means a material that can be used in an organic electroluminescent device and can contain at least one compound. If necessary, the organic electroluminescent material can be contained in any layer constituting the organic electroluminescent device. For example, the organic electroluminescent material can be a hole injection material, a hole transport material, a hole auxiliary material, a luminescence auxiliary material, an electron blocking material, a luminescent material (containing a host material and a dopant material), an electron buffer material, a hole blocking material, an electron transport material, an electron injection material, etc.

[0076] The term "multiple organic electroluminescent materials" in the present invention means one or more organic electroluminescent materials comprising a combination of at least two compounds, which may be included in any layer constituting an organic electroluminescent device. It may mean both the material contained in the organic electroluminescent device before (e.g., before vapor deposition) and the material contained in the organic electroluminescent device after (e.g., after vapor deposition). For example, a variety of organic electroluminescent materials may be a combination of at least two compounds, which may be included in at least one of the following: a hole injection layer, a hole transport layer, a hole auxiliary layer, a luminescent auxiliary layer, an electron blocking layer, a luminescent layer, an electron buffer layer, a hole blocking layer, an electron transport layer, and an electron injection layer. At least two compounds may be included in the same layer or in different layers, and may be mixed-evaporated or co-evaporated, or may be evaporated individually.

[0077] The term "multiple host materials" in the present invention means an organic electroluminescent material comprising a combination of at least two host materials. It may mean both a material contained in an organic electroluminescent device before (e.g., before vapor deposition) and a material contained in an organic electroluminescent device after (e.g., after vapor deposition). The multiple host materials of the present disclosure may be contained in any light-emitting layer constituting an organic electroluminescent device. Two or more compounds contained in the multiple host materials of the present disclosure may be contained in one light-emitting layer, or may be contained in different light-emitting layers, respectively. For example, when two or more host materials are contained in one layer, the layer may be formed by mixed evaporation, or may be formed by separate co-evaporation at the same time.

[0078] Definition of Substituent Terms

[0079] As used in the present invention, the term "halogen" may include fluorine, chlorine, bromine or iodine.

[0080] As used in the present invention, the term "C1-C30 alkyl" refers to a monovalent substituent derived from a straight or branched chain saturated hydrocarbon having 1 to 30 carbon atoms, examples of which include but are not limited to methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, isopentyl and hexyl.

[0081] As used in the present invention, the term "C3-C30 cycloalkyl" refers to a monocyclic hydrocarbon or a polycyclic hydrocarbon derived from a ring having 1 to 30 main chain carbon atoms, and the cycloalkane may include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopentylmethyl, cyclohexylmethyl, adamantyl, and the like.

[0082] In the present invention, aryl and arylene include monocyclic, polycyclic or condensed ring aromatic groups, the rings may be interrupted by short non-aromatic units, and may contain spiro structures, including but not limited to phenyl, biphenyl, terphenyl, naphthyl, phenanthrenyl, phenylphenanthrenyl, binaphthyl, phenylnaphthyl, naphthylphenyl, anthracenyl, indenyl, triphenylene, naphthylene, pyrenyl, peryl, fluorenyl, phenylfluorenyl, diphenylfluorenyl, benzofluorenyl, spirobifluorenyl, Base, naphthacetyl, fluoranthenyl, etc.

[0083] In the present invention, the heteroaryl and heteroarylene group include monocyclic, polycyclic or condensed-ring heteroaryl groups. The rings may be interrupted by short non-aromatic units. The heteroatoms include nitrogen, oxygen and sulfur. Including but not limited to furanyl, phenylthio, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetrazinyl, triazolyl, tetrazolyl, furazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, benzofuranyl, benzothiophenyl, isobenzofuranyl, dibenzofuranyl, dibenzothiophenyl, benzimidazolyl, benzothiazolyl, benzisothiazolyl, benzisoxazolyl, benzoxazolyl, isoindolyl, indolyl, indazolyl, benzothiadiazolyl, quinolyl, isoquinolyl, cinnolinyl, quinazolinyl, quinoxalinyl, carbazolyl, phenoxazinyl, phenothiazinyl, phenanthridinyl, benzodioxolyl, dihydroacridinyl, and derivatives thereof.

[0084] As used in the present invention, the term "substituted" refers to a hydrogen atom in a compound being replaced by another substituent. The position is not limited to a specific position, as long as the hydrogen at the position can be replaced by a substituent. It also includes a hydrogen atom being replaced by a group formed by the connection of two or more substituents. When two or more substituents appear, the two or more substituents may be the same or different. For example, the group formed by the connection of two or more substituents may be pyridine-triazine. That is, pyridine-triazine may be interpreted as a heteroaryl substituent, or a substituent in which two heteroaryl substituents are connected.

[0085] As used herein, unless otherwise specified, hydrogen atoms include protium, deuterium and tritium.

[0086] In the present invention, the range of the number of carbon atoms is defined in the definition of the group, and the number of carbon atoms is any integer within the defined range. For example, C6-C30 aromatic group, the number of carbon atoms representing the aromatic group can be any integer within the range of 6-60, such as 6, 8, 10, 13, 15, 17, 20, 22, 25 or 30, etc.

[0087] Compared with the prior art, the present invention has the following beneficial effects:

[0088] The organic compound of the present invention is used as an organic electroluminescent material, which can make the organic electroluminescent device have a low driving voltage (below 3.54V), a high current efficiency (above 18Cd / A) and a long life (above 270h). BRIEF DESCRIPTION OF THE DRAWINGS

[0089] Figure 1 is a schematic structural diagram of the organic electroluminescent device of the present invention;

[0090] Among them, 1 is a substrate, 2 is an anode, 3 is a hole injection layer, 4 is a hole transport layer, 5 is a light emitting layer, 6 is an electron transport layer, 7 is an electron injection layer, and 8 is a cathode. DETAILED DESCRIPTION

[0091] The technical solution of the present invention is further described below by specific implementation methods. It should be understood by those skilled in the art that the embodiments are only to help understand the present invention and should not be regarded as specific limitations of the present invention.

[0092] Example 1, Synthesis of Compound 1

[0093]

[0094] Synthesis of compound 1: Take a 100 ml three-necked round-bottom flask and put in a stirrer and a reflux tube. After drying, fill with nitrogen, add raw material 1-A (10 mmol), raw material 1-B (10 mmol), sodium bicarbonate (23 mmol), tetrakistriphenylphosphine palladium (0.5 mmol), dichlorodi-tert-butyl-(4-dimethylaminophenyl)phosphine palladium (0.5 mmol), toluene (25 ml), ethanol (7 ml) and water (7 ml), and replace with nitrogen three times. Under nitrogen protection, heat to 80 ° C for 8 hours. After the reaction, extract with ethyl acetate, add magnesium sulfate to dry, filter and spin dry in sequence; the crude product is purified by chromatography (ethyl acetate: n-hexane (volume ratio 1:10)) to obtain compound 1 (4.19 g, yield 63%).

[0095] Elemental analysis: C 47 H 27 Theoretical value of N3O2: C, 84.79; H, 4.09; N, 6.31; O, 4.81; Found value: C, 84.83; H, 4.12; N, 6.24; HRMS (ESI) m / z [M+H]+: Theoretical value: 665.21; Found value: 666.17.

[0096] Wherein nA and nB are raw materials obtained from commercial channels. The preparation methods of the compounds described in Examples 2-8 are the same as those in Example 1, except that nA replaces 1-A and nB replaces 1-B. The reaction raw materials and products are shown in Table 1, and the elemental analysis results are shown in Table 2.

[0097] Table 1

[0098]

[0099]

[0100] Table 2

[0101]

[0102] Example 10

[0103] Synthesis of compound 9

[0104]

[0105] Synthesis of intermediate 9-c: In a 50 ml three-necked flask, raw material 9-a (10 mmol), raw material 9-b (10 mmol), sodium bicarbonate (20 mmol), tetrakistriphenylphosphine palladium (0.2 mmol), tetrahydrofuran (20 ml), water (10 ml), nitrogen replacement, heating to 60 ° C overnight reaction under nitrogen protection. After the reaction is completed, water is added to quench, dichloromethane is extracted, and the organic solvent is removed by rotary evaporation. The crude product is separated by column chromatography (ethyl acetate: n-hexane (volume ratio 1:50)) to obtain intermediate 9-c (2.70 g, yield 84%).

[0106] Synthesis of intermediate 9-d: In a 50 ml three-necked flask, intermediate 9-c (10 mmol), (methoxymethyl) triphenylphosphine chloride (20 mmol), tetrahydrofuran (10 ml), the temperature was lowered to 0°C, potassium tert-butoxide (2 mmol) was dissolved in 5 ml tetrahydrofuran, nitrogen was replaced, and potassium tert-butoxide solution was added dropwise at 0°C under nitrogen protection. After the addition was completed, the reaction was stirred for half an hour. After the reaction was completed, water was added to quench, dichloromethane was extracted, and the organic solvent was removed by rotary evaporation. The crude product was separated by column chromatography (ethyl acetate: n-hexane (volume ratio 1:50)) to obtain intermediate 9-d (1.86 g, yield 53%).

[0107] Synthesis of intermediate 9-e: In a 25 ml three-necked flask, add intermediate 9-d (1 mmol) and hexafluoroisopropanol (5 ml), cool to 0°C, replace with nitrogen, add trifluoromethanesulfonic acid (1 ml) dropwise under nitrogen protection, continue stirring and react for half an hour, and separate the crude product by column chromatography (ethyl acetate: n-hexane (volume ratio 1:50)) to obtain intermediate 9-e (0.22 g, yield 68%).

[0108] Synthesis of intermediate 9-C: In a 50 ml three-necked round-bottom flask, intermediate 9-e (10 mmol), biboric acid pinacol ester (12 mmol), sodium acetate (20 mmol), tris (dibenzylideneacetone) dipalladium (0.5 mmol) and 2-dicyclohexylphosphine-2',6'-dimethoxybiphenyl (1.5 mmol) were added, and 1,4-dioxane (20 ml) was added, and nitrogen was replaced three times. Under nitrogen protection, the reaction was heated to 100 ° C. After the reaction was completed, water was added to quench, dichloromethane was extracted, and the organic solvent was removed by rotary evaporation. The crude product was separated by column chromatography (ethyl acetate: n-hexane (volume ratio 1:50)) to obtain intermediate 9-C (3.16 g, yield 77%).

[0109] Synthesis of compound 9: Take a 100 ml three-necked round-bottom flask and put in a stirrer and a reflux tube. After drying, fill with nitrogen, add intermediate 9-C (10 mmol), raw material 1-A (10 mmol), sodium bicarbonate (23 mmol), tetrakistriphenylphosphine palladium (0.5 mmol), dichlorodi-tert-butyl-(4-dimethylaminophenyl)phosphine palladium (0.5 mmol), toluene (25 ml), ethanol (7 ml) and water (7 ml), and replace with nitrogen three times. Under nitrogen protection, heat to 80 ° C for 8 hours. After the reaction, extract with ethyl acetate, add magnesium sulfate to dry, filter and spin dry; the crude product is purified by chromatography (ethyl acetate: n-hexane (volume ratio 1:10)) to obtain compound 9 (4.49 g, yield 66%).

[0110] Elemental analysis: C 47 H 27 N3OS theoretical value: C, 82.80; H, 3.99; N, 6.16; O, 2.35; S, 4.70; found value: C, 82.85; H, 4.01; N, 6.09; S, 4.71; HRMS (ESI) m / z [M+H]+: theoretical value: 681.19; found value: 682.14.

[0111] Embodiment 11

[0112] Synthesis of compound 157

[0113]

[0114] Synthesis of intermediate 157-c: Take a 100 ml three-necked round-bottom flask and put in a stirring bar and a reflux tube, add intermediate 157-a (1 mmol), raw material 157-b (1 mmol), toluene (9 ml), ethanol (3 ml), water (3 ml), add tetrakistriphenylphosphine palladium (0.05 mmol), potassium carbonate (2 mmol), heat to 90°C, react for 12 hours, after the reaction is completed, cool to room temperature, extract with water and ethyl acetate, dry the organic phase with anhydrous magnesium sulfate, use a rotary evaporator to remove the solvent, and separate the crude product by column chromatography (DCM: n-hexane = 1:50) to obtain intermediate 157-c (0.25 g, yield 78%).

[0115] Synthesis of intermediate 157-d: Take a 100 ml three-necked round-bottom flask and put in a stirrer and a reflux tube, add intermediate 157-c (1 mmol), (methoxymethyl) triphenylphosphine chloride (1.8 mmol), THF (10 ml), cool to -5 to -10 ° C, and slowly add a solution of t-BuOK (27 g) in tetrahydrofuran (150 mL) using a constant pressure dropping funnel, and the temperature is always maintained below -5 ° C. After the addition is complete, react at this temperature for 20 minutes. Then slowly warm to room temperature, and after the reaction liquid reaches room temperature, continue to react for 1 hour, and stop the reaction. The reaction liquid is extracted with water and ethyl acetate, the organic phase is dried with anhydrous magnesium sulfate, and the solvent is removed using a rotary evaporator. The crude product is separated by column chromatography (DCM: n-hexane = 1:50) to obtain intermediate 157-d (0.29 g, yield 83%).

[0116] Synthesis of intermediate 157-e: Take a 100 ml three-necked round-bottom flask and put in a stirrer and a reflux tube, add intermediate 157-d (1 mmol) and hexafluoroisopropanol (14 mL). Under nitrogen protection, the temperature was lowered to -5 to -10 ° C. After reaching this temperature, trifluoromethanesulfonic acid (3 mmol) was slowly added dropwise using a constant pressure dropping funnel, and the temperature was always maintained below -5 ° C. After the addition was completed, the reaction was carried out at this temperature for 20 minutes. Then the temperature was slowly raised to room temperature. After the reaction liquid reached room temperature, the reaction was continued for 1 hour, and the reaction was stopped. The reaction liquid was extracted with water and ethyl acetate, the organic phase was dried with anhydrous magnesium sulfate, the solvent was removed using a rotary evaporator, and the crude product was separated by column chromatography (DCM: n-hexane = 1:50) to obtain intermediate 157-e (0.26 g, yield 81%).

[0117] Synthesis of intermediate 157-D: The same synthesis as intermediate 9-4, except that intermediate 157-e was used instead of intermediate 9-e to obtain intermediate 157-D (0.34 g, yield 82%)

[0118] Synthesis of compound 157: The synthesis was the same as that of compound 1, except that intermediate 157-D was used instead of intermediate 1-B, and raw material 21-A was used instead of raw material 1-A, to obtain compound 157 (4.60 g, yield 66%).

[0119] Elemental analysis: C 46 H 26 Theoretical value of N4S2: C, 79.06; H, 3.75; N, 8.02; S, 9.17; Found value: C, 79.06; H, 3.75; N, 8.02; S, 9.17; HRMS (ESI) m / z [M+H]+: Theoretical value: 698.16; Found value: 699.33.

[0120] In the preparation of the compounds of Examples 12-22, nA is a raw material product obtained from commercial channels, and the preparation methods of the intermediates nC and nD are the same as those of 9-C and 157-D, respectively, except that as the starting materials, na replaces 9-a, nb replaces 9-b, or na replaces 157-a, and nb replaces 157-b. The preparation of the compounds is the same as the synthesis of compound 1, except that intermediate nC or nD replaces intermediate 1-B, and raw material nA replaces raw material 1-A. The reaction raw materials, intermediates nC / D and products are shown in Table 3, and the elemental analysis results are shown in Table 4.

[0121] Table 3

[0122]

[0123]

[0124]

[0125] Table 4

[0126]

[0127]

[0128] Device Embodiment

[0129] An organic electroluminescent device is provided, which has the following layer structure: substrate (indium tin oxide (ITO) coated glass substrate) / hole injection layer (HIL) / hole transport layer (HTL) / electron blocking layer (EBL) / luminescent layer (EML) / hole blocking layer (HBL) electron transport layer (ETL) / electron injection layer (EIL), and finally a cathode.

[0130] The materials needed to make OLEDs are as follows:

[0131]

[0132]

[0133] The preparation of the organic electroluminescent device comprises the following steps:

[0134] (1) Substrate cleaning: The glass substrate coated with transparent ITO is ultrasonically treated in an aqueous cleaning agent (the composition and concentration of the aqueous cleaning agent: ethylene glycol solvent ≤ 10wt%, triethanolamine ≤ 1wt%), rinsed in deionized water, ultrasonically degreased in an acetone: ethanol mixed solvent (volume ratio 1:1), baked in a clean environment until the water is completely removed, and then cleaned with ultraviolet light and ozone.

[0135] (2) Evaporation of organic light-emitting functional layer:

[0136] The glass substrate with the anode layer is placed in a vacuum chamber and evacuated to 1×10 -6 Up to 2×10 -4 Pa, vacuum evaporating a mixture of HATCN and HT on the above anode layer film, wherein the mass ratio of HATCN to HT is 3:97, as a hole injection layer, and the evaporation thickness is 10 nm;

[0137] A hole transport layer (made of HT) is evaporated on the hole injection layer, with a thickness of 80 nm.

[0138] The light-emitting layer is deposited on the hole transport layer. The specific preparation method is: vacuum-deposit the light-emitting host material (the materials are shown in Table 1) and the guest material (piq)2Ir(acac) in a co-evaporation manner, and the total film thickness of the deposition is 30 nm;

[0139] An electronic buffer layer (optional) is evaporated on the light-emitting layer with a thickness of 10 nm;

[0140] An electron transport layer is evaporated on the electron buffer layer. The specific preparation method is: vacuum evaporation of ET and LiQ in a co-evaporation manner, and the total evaporation film thickness is 30nm;

[0141] An electron injection layer (made of LiQ) is vacuum-deposited on the electron transport layer, with a total film thickness of 1 nm.

[0142] Al was evaporated on the electron injection layer, and the total film thickness of the evaporated layer was 90 nm.

[0143] The parameters of each layer in the device, its material, thickness, etc. are shown in Table 5 below:

[0144] Table 5

[0145]

[0146]

[0147]

[0148] Device performance test:

[0149] Test samples: organic electroluminescent devices provided in device examples 1-11 and comparative example 1;

[0150] Test instruments: The device's current, voltage, brightness, luminous spectrum and other characteristics are tested synchronously using a PR 650 spectrum scanning luminance meter and a Keithley K 2400 digital source meter system;

[0151] Test conditions: Photoelectric properties Test conditions: Current density is 10mA / cm 2 ;

[0152] Life test: current density is 50mA / cm 2 , record the time (in hours) when the device brightness drops to 95% of the original brightness;

[0153] The test results are shown in Table 6 below:

[0154] Table 6

[0155] project Driving voltage(V) Current efficiency (Cd / A) Lifespan T95(hrs) Device Example 1 3.42 22.14 331.7 Device Example 2 3.41 22.54 325.8 Device Example 3 3.44 21.24 324.5 Device Example 4 3.42 22.36 335.4 Device Example 5 3.43 21.86 326.3 Device Example 6 3.44 21.26 321.1 Device Example 7 3.43 21.50 322.6 Device Example 8 3.44 21.32 320.5 Device Example 9 3.45 19.45 310.2 Device Example 10 3.44 21.29 312.8 Device Example 11 3.43 22.03 320.1 Device Example 12 3.43 21.06 306.4 Device Example 13 3.47 19.56 314.5 Device Example 14 3.51 18.57 301.6 Device Example 15 3.54 18.29 271.5 Device Example 16 3.44 21.47 315.8 Device Example 17 3.42 22.06 321.5 Device Example 18 3.44 20.65 306.7 Device Example 19 3.45 19.83 306.4 Device Example 20 3.52 18.65 285.4 Device Example 21 3.43 19.68 312.7 Device Example 22 3.53 18.69 288.1 Comparative Example 1 5.40 12.36 75.0 Comparative Example 2 3.61 17.94 152.6

[0156] It can be seen from the data in Table 6 that the organic compound of the present invention, as a light-emitting layer material, can enable the organic electroluminescent device to have a low driving voltage (below 3.54 V), a high current efficiency (above 18 Cd / A) and a long life (above 270 h).

[0157] The applicant declares that the present invention illustrates the organic compounds and applications of the present invention through the above-mentioned embodiments, but the present invention is not limited to the above-mentioned embodiments, that is, it does not mean that the present invention must rely on the above-mentioned embodiments to be implemented. Those skilled in the art should understand that any improvement of the present invention, equivalent replacement of the raw materials selected by the present invention, addition of auxiliary components, selection of specific methods, etc., all fall within the protection scope and disclosure scope of the present invention.

Claims

1. An organic compound, characterized in that The organic compound has a structure shown in Formula 1 Among them, R 3 -R 10 One of them and R in the structure shown in formula 2 11 -R 14 Connect any one of them, X is selected from O or S; X1 is selected from O or S; X2 is selected from C or N; R 3 -R 10 Any one of the groups not connected to Formula 2 is connected to the structure shown in Formula 3, in is the connection site, R 3 -R 10 The groups not connected to Formula 2 or Formula 3 are independently selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl or substituted or unsubstituted C3-C30 cycloalkyl, R 11 -R 14 The groups not connected to Formula 1 are each independently selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl or substituted or unsubstituted C3-C30 cycloalkyl, R 1 , R 2 Each is independently selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C30 alkyl, a group obtained by replacing one or at least two methylene groups in the substituted or unsubstituted C1-C30 alkyl with -O- or -S- in a non-adjacent O atom or S atom, a substituted or unsubstituted C2-C30 alkenyl, a group obtained by replacing one or at least two methylene groups in the substituted or unsubstituted C2-C30 alkenyl with -O- or -S- in a non-adjacent O atom or S atom, a substituted or unsubstituted C7-C30 aralkyl, a substituted or unsubstituted C6-C30 aryl, a substituted or unsubstituted C3-C30 heteroaryl, a substituted or unsubstituted C4-C30 heteroaralkyl, a substituted or unsubstituted C3-C30 cycloalkyl, a substituted or unsubstituted C3-C30 heterocycloalkyl, and a substituted or unsubstituted C3-C30 cycloalkenyl.

2. The organic compound according to claim 1, characterized in that R 3 -R 10 The groups not connected to Formula 2 or Formula 3 are each independently selected from hydrogen or deuterium.

3. The organic compound according to claim 1 or 2, characterized in that R 11 -R 14 The groups not connected to Formula 1 are each independently selected from hydrogen or deuterium.

4. The organic compound according to any one of claims 1 to 3, characterized in that R 1 , R 2 Each is independently selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, anthracenyl, phenyl-substituted naphthyl, naphthyl-substituted phenyl, pyridyl, pyridyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, dimethylfluorenyl, diphenylfluorenyl, spirobifluorenyl, dibenzofuran-substituted phenyl, dibenzothiophene-substituted phenyl, dimethylfluorenyl-substituted phenyl, benzocarbazolyl, benzonaphthofuranyl or benzonaphthothiophenyl.

5. The organic compound according to any one of claims 1 to 4, characterized in that The substituted substituents are each independently selected from any one or a combination of at least two of deuterium, halogen, cyano, C1-C30 straight or branched alkyl, C3-C30 cycloalkyl, C6-C60 aryl or C3-C60 heteroaryl; Preferably, the substituted substituents are each independently selected from any one or a combination of at least two of deuterium, halogen, cyano, methyl, phenyl, naphthyl, dibenzofuranyl, dibenzothienyl or dimethylfluorenyl.

6. The organic compound according to any one of claims 1 to 5, characterized in that R 7 With R 11 -R 14 Any connection; Preferably, R 8 -R 10 Any one of them is connected with Formula 3; More preferably, R 7 With R 13 connect; More preferably, R 9 Connect with formula 3; Preferably, R 8 With R 11 -R 14 Any connection; Preferably, R 7 , R 9 -R 10 Any one of them is connected with Formula 3; More preferably, R 8 With R 13 connect; Preferably, R 9 With R 11 -R 14 Any connection; Preferably, R 7 -R 8 , R 10 Any one of them is connected with Formula 3; More preferably, R 9 With R 13 connect; More preferably, R 7 Connect with formula 3; Preferably, R 10 With R 11 -R 14 Any connection; Preferably, R 7 -R 9 Any one of them is connected with Formula 3; More preferably, R 10 With R 13 connect.

7. The organic compound according to any one of claims 1 to 6, characterized in that The organic compound is selected from any one of the following compounds:

8. An organic electroluminescent device, characterized in that: The organic electroluminescent device comprises a first electrode, a second electrode, and an organic layer disposed between the first electrode and the second electrode, wherein a material of the organic layer comprises at least one of the organic compounds according to any one of claims 1 to 7.

9. The organic electroluminescent device according to claim 8, characterized in that: The organic layer comprises at least one of a hole injection layer, a first hole transport layer, a second hole transport layer, an electron blocking layer, a light emitting layer, an electron buffer layer, an electron transport layer or an electron injection layer; Preferably, the organic layer comprises an electron buffer layer, and the electron buffer layer comprises at least one of the organic compounds described above; Preferably, the organic layer comprises an electron transport layer, and the electron transport layer comprises at least one of the organic compounds described above; Preferably, the organic layer comprises a light-emitting layer, and the light-emitting layer comprises at least one of the organic compounds described above; Preferably, the light-emitting layer further comprises an iridium-containing complex.

10. A product, characterized in that It comprises the organic electroluminescent device according to claim 8 or 9.

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