Organic material composition and application thereof

Abstract

The invention relates to the technical field of display, in particular to an organic material composition and application thereof. In the composition of the organic material, the composition of the organic material comprises a first compound and a second compound, the first compound and the second compound have the following structures: # imgabs0 # are matched with each other through the first compound with the structure as shown in a formula (1) and the second compound with the structure as shown in a formula (2), so that HOMO and LUMO energy levels can be matched with adjacent energy levels, the composition of the organic material obtains relatively high stability, and the carrier mobility is relatively balanced; therefore, the organic light-emitting device containing the material has longer service life, lower driving voltage and higher efficiency.

Description

Technical Field

[0001] The present invention relates to the field of display technologies, and particularly relates to a composition of an organic material and its applications. Background Art

[0002] An organic light-emitting device (OLED) converts electrical energy into light by applying electricity to an organic light-emitting material, and generally includes an anode, a cathode, and an organic layer formed between these two electrodes. The organic layer of the organic EL device may include a hole injection layer, a hole transport layer, a hole assisting layer, a light-emitting assisting layer, an electron blocking layer, a light-emitting 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 classified into hole injection materials, hole transport materials, hole assisting materials, light-emitting assisting materials, electron blocking materials, light-emitting materials, electron buffer materials, hole blocking materials, electron transport materials, electron injection materials, etc. depending on their functions. In the organic EL device, holes from the anode and electrons from the cathode are injected into the light-emitting layer by applying a voltage, and excitons with high energy are generated by the recombination of holes and electrons. The organic light-emitting compound emits light by the energy moving to the excited state and the energy when the organic light-emitting compound returns from the excited state to the ground state.

[0003] Currently, due to reasons such as low stability and unbalanced carrier mobility of the functional materials composed of existing organic light-emitting compounds, the problems of high driving voltage and short lifespan of organic light-emitting diodes are caused, severely limiting the applications of organic light-emitting diodes. Summary of the Invention

[0004] The object of the present invention is to overcome the defects that the functional materials composed of existing organic light-emitting compounds have low stability, unbalanced carrier mobility, etc., resulting in high driving voltage and short lifespan of organic light-emitting diodes, and thus severely limiting the applications of organic light-emitting diodes, and further provide an organic light-emitting material and its applications.

[0005] Definition of substituent terms in the present invention:

[0006] As used in the present invention, the term "halogen" may include fluorine, chlorine, bromine, or iodine.

[0007] As used in the present invention, the term "C1-C30 alkyl" refers to a monovalent substituent derived from a straight-chain or branched-chain saturated hydrocarbon having 1 to 30 carbon atoms, and its examples include but are not limited to methyl, ethyl, propyl, isobutyl, sec-butyl, tert-butyl, pentyl, isopentyl, and hexyl.

[0008] As used in the present invention, the term "C3-C30 cycloalkyl" refers to a monocyclic hydrocarbon or polycyclic hydrocarbon derived from a hydrocarbon having 1 to 30 ring backbone carbon atoms, and the cycloalkane may include cyclopropyl, cyclobutyl, adamantyl, etc.

[0009] In the present invention, aryl and arylene include monocyclic, polycyclic or fused-ring aryl, and the rings may be interrupted by short non-aromatic units and may include a spiro structure. Aryl includes but is not limited to phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, anthryl, fluorenyl, spirobifluorenyl, etc., and arylene includes but is not limited to phenylene, biphenylene, terphenylene, naphthylene, phenanthrylene, anthrylene, fluorenylene, spirobifluorenylene, etc.

[0010] In the present invention, heteroaryl and heteroarylene include monocyclic, polycyclic or fused-ring heteroaryl, and the rings may be interrupted by short non-aromatic units. The heteroatoms include nitrogen, oxygen and sulfur. Heteroaryl includes but is not limited to furyl, phenylthio, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetrazinyl, triazolyl, tetrazolyl, furazanyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, benzofuryl, benzothienyl, isobenzofuryl, dibenzofuryl, dibenzothienyl, benzimidazolyl, benzothiazolyl, benzoisothiazolyl, benzoisoxazolyl, benzoxazolyl, isoindolyl, indolyl, indazolyl, benzothiadiazolyl, quinolinyl, isoquinolinyl, cinnolinyl, quinazolinyl, quinoxalinyl, carbazolyl, phenoxazinyl, phenothiazinyl, phenanthridinyl, benzodioxolyl, dihydroacridinyl, and their derivatives, etc.; heteroarylene includes but is not limited to furylene, phenylthioylene, pyrrolylene, imidazolylene, pyrazolylene, thiazolylene, thiadiazolylene, isothiazolylene, isoxazolylene, oxazolylene, oxadiazolylene, triazinylene, tetrazinylene, triazolylene, tetrazolylene, furazanylene, pyridinylene, pyrazinylene, pyrimidinylene, pyridazinylene, benzofurylene, benzothienylene, isobenzofurylene, dibenzofurylene, dibenzothienylene, benzimidazolylene, benzothiazolylene, benzoisothiazolylene, benzoisoxazolylene, benzoxazolylene, isoindolylene, indolylene, indazolylene, benzothiadiazolylene, quinolinylene, isoquinolinylene, cinnolinylene, quinazolinylene, quinoxalinylene, carbazolylene, phenoxazinylene, phenothiazinylene, phenanthridinylene, benzodioxolylene, dihydroacridinylene, and their derivatives, etc.

[0011] As used in the present invention, the term "substituted" means that a hydrogen atom in a compound is replaced by another substituent. The position is not limited to a specific position as long as the hydrogen at that position can be replaced by a substituent. When there are two or more substituents, the two or more substituents may be the same or different.

[0012] As used in the present invention, unless otherwise specified, a hydrogen atom includes protium, deuterium, and tritium.

[0013] In the present invention, in the definition of a group, a range of the number of carbon atoms is defined, and the number of carbon atoms is any integer within the defined range. For example, C6-C30 aryl means that the number of carbon atoms of the aryl can be any integer within the range of 6-60, such as 6, 8, 10, 13, 15, 17, 20, 22, 25, or 30, etc.

[0014] The solution adopted in the present invention is as follows:

[0015] The present invention provides a composition of an organic material, and the composition of the organic material includes a first compound and a second compound. The first compound has a structure shown in formula (1):

[0016]

[0017] Wherein, in formula (1), Ar is selected from a substituted or unsubstituted C6-C60 aryl group, a substituted or unsubstituted C3-C60 heteroaryl group;

[0018] The second compound has a structure shown in formula (2):

[0019]

[0020] Formula (2)

[0021] Wherein, Ar 1 , Ar 2 are each independently selected from a substituted or unsubstituted C6-C60 aryl group, a substituted or unsubstituted C3-C60 heteroaryl group;

[0022] The substituents in the substituted C6-C60 aryl group and the substituted C3-C60 heteroaryl group are each independently selected from one or a combination of at least two of deuterium, halogen, cyano, a C1-C12 alkyl group, a C3-C12 cycloalkyl group, a C6-C30 aryl group, a C3-C30 heteroaryl group, a C6-C60 arylamino group, and a C3-C60 heteroarylamino group.

[0023] It can be understood that in formula (1), the F phenyl group can be substituted at any substitutable position on ring D or ring E; It can be substituted at any substitutable position on ring A, ring B, or ring C and at any substitutable position on ring D or ring E.

[0024] Preferably, formula (1) is selected from one of the structures shown in I-1 to I-4 below:

[0025]

[0026] Preferably, Ar is selected from substituted or unsubstituted C6-C60 non-condensed aryl groups and substituted or unsubstituted C3-C60 non-condensed heteroaryl groups;

[0027] The substituents in the substituted C6-C60 non-condensed aryl groups and substituted C3-C60 non-condensed heteroaryl groups are each independently selected from one or a combination of at least two of deuterium, halogen, cyano, C1-C12 alkyl groups, C3-C12 cycloalkyl groups, C6-C30 aryl groups, C3-C30 heteroaryl groups, C6-C60 arylamino groups, and C3-C60 heteroarylamino groups;

[0028] Preferably, Ar is selected from substituted or unsubstituted C6-C20 non-condensed aryl groups and substituted or unsubstituted C3-C20 non-condensed heteroaryl groups;

[0029] The substituents in the substituted C6-C20 non-condensed aryl groups and substituted C3-C20 non-condensed heteroaryl groups are each independently selected from one or a combination of at least two of deuterium, halogen, cyano, C1-C12 alkyl groups, C3-C12 cycloalkyl groups, C6-C30 aryl groups, C3-C30 heteroaryl groups, C6-C60 arylamino groups, and C3-C60 heteroarylamino groups;

[0030] Ar is selected from substituted or unsubstituted A groups, and the A group is selected from one of the following groups: phenyl, biphenyl, terphenyl;

[0031] The substituents in the substituted A group are selected from deuterium, phenyl, and naphthyl;

[0032] Preferably, Ar is selected from phenyl, biphenyl, terphenyl, and naphthylphenyl.

[0033] Preferably, the first compound is selected from any one of the following M-1 to M-104:

[0034]

[0035]

[0036]

[0037]

[0038] Preferably, in formula (2), Ar 1 , Ar 2 are each independently selected from substituted or unsubstituted C6-C20 aryl groups and substituted or unsubstituted C3-C20 heteroaryl groups;

[0039] Among them, the substituents in the substituted C6-C20 aryl group and the substituted C3-C230 heteroaryl group are each independently selected from one or a combination of at least two of deuterium, halogen, cyano, C1-C12 alkyl group, C3-C12 cycloalkyl group, C6-C30 aryl group, C3-C30 heteroaryl group, C6-C60 arylamino group, and C3-C60 heteroarylamino group;

[0040] Preferably, Ar 1 , Ar 2 are each independently selected from a substituted or unsubstituted A group, and the A group is selected from phenyl, biphenyl, naphthyl, dibenzofuranyl, dibenzothiophenyl, benzonaphthofuranyl, benzonaphthothiophenyl, terphenyl, and phenanthryl;

[0041] Among them, the substituents of the substituted A group are selected from C1-C6 alkyl group and C6-C12 aryl group;

[0042] Preferably, Ar 1 is selected from phenyl, dibenzofuranyl, phenyldibenzofuranyl, dibenzothiophenyl, phenyldibenzothiophenyl, benzonaphthofuranyl, and benzonaphthothiophenyl;

[0043] Ar 2 is selected from phenyl, biphenyl, terphenyl, phenanthryl, naphthyl, phenylnaphthyl, and naphthylphenyl.

[0044] Preferably, the second compound is selected from any one of the following N-1 to N-15:

[0045]

[0046] Preferably, in the material composition, the mass ratio of the first compound to the second compound is 1:9 - 9:1;

[0047] Preferably, in the material composition, the mass ratio of the first compound to the second compound is 2:8 - 8:2;

[0048] More preferably, in the material composition, the mass ratio of the first compound to the second compound is 3:7 - 7:3;

[0049] Further preferably, in the material composition, the mass ratio of the first compound to the second compound is 4:6 - 6:4.

[0050] The present invention provides an organic electroluminescent host material composition, comprising the composition of the above-mentioned organic materials.

[0051] The present invention also provides the application of the composition of the above-mentioned organic materials or the above-mentioned organic electroluminescent host material composition in optical devices;

[0052] Preferably, the optical device includes an organic electroluminescent device.

[0053] The present invention also provides an organic electroluminescent device, which includes an anode and a cathode, and an organic layer disposed between the anode and the cathode. The organic layer includes the composition of the above-mentioned organic materials or the composition of the above-mentioned organic electroluminescent host material composition. Preferably, the light-emitting layer in the organic layer includes the composition of the above-mentioned organic materials or the composition of the above-mentioned organic electroluminescent host material composition.

[0054] Preferably, the organic layer includes a hole injection layer, a hole transport layer, an electron blocking layer, a light-emitting layer, a hole blocking layer, an electron transport layer, and an electron injection layer that are sequentially stacked from the anode side to the cathode side;

[0055] Preferably, the material of the light-emitting layer includes a host material and a guest material, and the host material includes the composition of the above-mentioned organic materials or the composition of the above-mentioned organic electroluminescent host material composition;

[0056] Preferably, the guest material includes a phosphorescent dopant, and the phosphorescent dopant includes a transition metal-containing complex.

[0057] The present invention also provides an organic electroluminescent device including the above-mentioned organic electroluminescent device.

[0058] 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 included 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 light-emitting auxiliary material, an electron blocking material, a light-emitting material (including an organic electroluminescent host material and a dopant material), an electron buffer material, a hole blocking material, an electron transport material, an electron injection material, etc.

[0059] An organic electroluminescent material disclosed in the present invention may include one organic electroluminescent material or may include a plurality of organic electroluminescent materials. Herein, the plurality of organic electroluminescent materials means a material comprising a combination of at least two organic electroluminescent materials, and the material may be included in any layer constituting the organic electroluminescent device. It may mean both a material before the organic electroluminescent device (e.g., before vapor deposition) and a material after the organic electroluminescent device (e.g., after vapor deposition). For example, the material may be a combination of at least two compositions, and the compositions may be included in at least one of the following: a hole injection layer, a hole transport layer, a hole assisting layer, a light emitting assisting layer, an electron blocking layer, a light emitting layer, an electron buffer layer, a hole blocking layer, an electron transport layer, and an electron injection layer. Two compositions in the plurality of organic electroluminescent materials may be included in the same layer or different layers, and may be mixed-evaporated or co-evaporated, or may be evaporated individually.

[0060] The term "organic electroluminescent host material composition" disclosed in the present invention means an organic electroluminescent material comprising a combination of at least two host materials. It may mean both a material before in the organic electroluminescent device (e.g., before vapor deposition) and a material after in the organic electroluminescent device (e.g., after vapor deposition). The composition disclosed in the present invention may be included in any light emitting layer constituting the organic electroluminescent device. Two or more compounds among the plurality of host materials included in the composition disclosed in the present invention may be included in one light emitting layer, or may be separately included in different light emitting layers. For example: when two or more host materials are included in one layer, the layer may be formed by mixed evaporation, or may be formed by co-evaporation separately at the same time.

[0061] Advantages of the present invention:

[0062] A composition of an organic material of the present invention, the composition of the organic material comprising a first compound and a second compound, the first compound having a structure represented by formula (1), and the second compound having a structure represented by formula (2); the cooperation between the first compound having the structure represented by formula (1) and the second compound having the structure represented by formula (2) is conducive to the matching of the HOMO and LUMO energy levels with adjacent energy levels, enabling the composition of the organic material to obtain higher stability and relatively balanced carrier mobilities, thereby making the organic electroluminescent device containing this material have more excellent lifetime, and at the same time having a lower driving voltage and higher efficiency. Description of the Drawings

[0063] To more clearly illustrate the specific embodiments of the present invention or the technical solutions in the prior art, the following will briefly introduce the drawings required for the description of the specific embodiments or the prior art. Obviously, the drawings in the following description are some embodiments of the present invention. For those of ordinary skill in the art, without creative efforts, other drawings can be obtained based on these drawings.

[0064] Figure 1 It is a structural diagram of an organic electroluminescent device in an embodiment of the device of the present invention;

[0065] Among them, 1 - substrate; 2 - anode; 3 - hole injection layer; 4 - hole transport layer; 5 - light-emitting layer; 6 - electron transport layer; 7 - electron injection layer; 8 - cathode. Specific Embodiments

[0066] The following embodiments are provided to better further understand the present invention. They are not limited to the best embodiments, and do not limit the content and protection scope of the present invention. Any product obtained by anyone under the inspiration of the present invention or by combining the features of the present invention with those of other prior arts and being the same or similar to the present invention falls within the protection scope of the present invention.

[0067] For those not specifying specific experimental steps or conditions in the embodiments, the operations or conditions of the conventional experimental steps described in the literature in this field can be followed. For reagents or instruments without indicating the manufacturer, they are all conventional reagent products that can be obtained through commercial purchase.

[0068] In the present invention, the first compound shown in formula (1) is prepared through the following synthetic route:

[0069]

[0070] The intermediate raw materials A-n, B-n, and C-n can all be directly purchased or synthesized through conventional reaction paths and conditions by referring to the methods reported in the existing literature.

[0071] The specific structures of the intermediate raw materials used in the embodiments provided by the present invention are as follows:

[0072] The specific structure of B-n is:

[0073]

[0074]

[0075] The specific structure of C-n is:

[0076]

[0077] Preparation of deuterated intermediates:

[0078]

[0079] In a clean 30 mL high-pressure reactor, raw material C-2 (1 mmol), platinum dioxide (20% w / w), heavy water (5 mL), and decahydroquinoline (5 mL) were added in sequence. Nitrogen was bubbled for at least 10 minutes, and the temperature was raised to 180 °C for reaction for at least 16 hours. After the reaction was completed, the temperature was lowered to room temperature. After extraction with ethyl acetate, the organic phase was dried with anhydrous magnesium sulfate, and the solvent was removed using a rotary evaporator to obtain a crude product. The above reaction process was repeated at least 2 times for the crude product to ensure that all the hydrogens on the aromatic ring were deuterated. Finally, the crude product was separated by column chromatography (ethyl acetate:n-hexane = 1:50) to obtain intermediate C-2-D (yield 13%).

[0080] Example 1

[0081] This example provides an organic electroluminescent compound M-3 in a composition of organic materials. The synthesis of the organic electroluminescent compound M-3 specifically includes the following steps:

[0082]

[0083] A 100 mL three-necked round-bottom flask was taken and a magnetic stir bar was placed in it and a reflux tube was connected above. Under nitrogen protection, raw material A-3 (1 mmol), 2,4-dichloro-6-phenyl-1,3,5-triazine (1.2 mmol), Pd(dppf)Cl2 (0.03 mmol), potassium carbonate (2.5 mmol), 1,4-dioxane / water (10 mL / 2 mL) were added in sequence. The temperature was raised to 60 °C and the reaction was carried out for 5 hours. After the reaction was completed, the temperature was lowered to room temperature, quenched with a saturated ammonium chloride aqueous solution, extracted with 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 (ethyl acetate:n-hexane = 1:50) to obtain intermediate M-3-1 (yield 61%).

[0084] A 100 mL three-necked round-bottom flask was taken and a magnetic stir bar was placed in it and a reflux tube was connected above. Under nitrogen protection, intermediate M-3-1 (1 mmol), 4,4,5,5-tetramethyl-2-(naphtho[2,1-b]benzofuran-1-yl)-1,3,2-dioxaborolane, i.e., C-1 (1.2 mmol), Pd(dppf)Cl2 (0.03 mmol), potassium carbonate (2.5 mmol), 1,4-dioxane / water (10 mL / 2 mL) were added in sequence. The temperature was raised to 90 °C and the reaction was carried out for 5 hours. After the reaction was completed, the temperature was lowered to room temperature, filtered by suction, the filter cake was washed twice with deionized water and twice with ethanol, and the obtained crude product was recrystallized and purified twice with o-dichlorobenzene to obtain the organic electroluminescent compound M-3 (yield 42%).

[0085] Elemental analysis: C41 H 25 N3. Theoretical values: C, 85.54; H, 4.38; N, 7.30; O, 2.78; Measured values: C, 85.48; H, 4.50; N, 7.24; HRMS(ESI) m / z [M+H] + : Theoretical value: 575.20; Measured value: 576.20.

[0086] Example 2

[0087] This example provides the organic electroluminescent compound M-54 in the composition of the organic material. The synthesis of the organic electroluminescent compound M-54 specifically includes the following steps:

[0088]

[0089] Take a 100 mL three-necked round-bottom flask, place a magnetic stir bar and connect it to a reflux condenser. Under nitrogen protection, sequentially add raw material A-54 (1 mmol), 2,4-dichloro-6-phenyl-1,3,5-triazine (1.2 mmol), Pd(dppf)Cl2 (0.03 mmol), potassium carbonate (2.5 mmol), 1,4-dioxane / water (10 mL / 2 mL). Heat the mixture to 60 °C and react for 5 hours. After the reaction is completed, cool it to room temperature, quench it with saturated ammonium chloride aqueous solution, extract with ethyl acetate, dry the organic phase with anhydrous magnesium sulfate, remove the solvent using a rotary evaporator, and separate the crude product by column chromatography (ethyl acetate: n-hexane = 1:50) to obtain intermediate M-54-1 (yield 45%).

[0090] Take a 100 mL three-necked round-bottom flask, place a magnetic stir bar and connect it to a reflux condenser. Under nitrogen protection, sequentially add intermediate M-54-1 (1 mmol), 4,4,5,5-tetramethyl-2-(naphtho[2,1-b]benzofuran-5-yl)-1,3,2-dioxaborolane, i.e., C-4 (1.2 mmol), Pd(dppf)Cl2 (0.03 mmol), potassium carbonate (2.5 mmol), 1,4-dioxane / water (10 mL / 2 mL). Heat the mixture to 90 °C and react for 5 hours. After the reaction is completed, cool it to room temperature, perform suction filtration, wash the filter cake twice with deionized water and twice with ethanol. The obtained crude product is recrystallized and purified twice with o-dichlorobenzene to obtain the organic electroluminescent compound 54 (yield 46%).

[0091] Elemental analysis: C 41 H 25 N3. Theoretical values: C, 85.54; H, 4.38; N, 7.30; O, 2.78; Measured values: C, 85.44; H, 4.54; N, 7.24; HRMS(ESI) m / z [M+H] +:Theoretical value: 575.20; Measured value: 576.20.

[0092] Example 3

[0093] This example provides the organic electroluminescent compound M-58 in the composition of the organic material. The synthesis of the organic electroluminescent compound M-58 specifically includes the following steps:

[0094]

[0095] Take a 100-milliliter three-necked round-bottom flask and place a stir bar and connect a reflux tube above. Under nitrogen protection, sequentially add raw material A-58 (1 mmol), 2-([1,1'-biphenyl]-3-yl)-4,6-dichloro-1,3,5-triazine, that is, B-2 (1.2 mmol), Pd(dppf)Cl2 (0.03 mmol), potassium carbonate (2.5 mmol), 1,4-dioxane / water (10 mL / 2 mL). Heat to 60 degrees Celsius and react for 5 hours. After the reaction is completed, cool to room temperature, quench with saturated ammonium chloride aqueous solution, extract with ethyl acetate, dry the organic phase with anhydrous magnesium sulfate, remove the solvent using a rotary evaporator, and separate the crude product by column chromatography (ethyl acetate: n-hexane = 1:50) to obtain intermediate M-59-1 (yield 54%).

[0096] Take a 100-milliliter three-necked round-bottom flask and place a stir bar and connect a reflux tube above. Under nitrogen protection, sequentially add intermediate M-59-1 (1 mmol), 4,4,5,5-tetramethyl-2-(naphtho[2,1-b]benzofuran-2-yl)-1,3,2-dioxaborolane, that is, C-3 (1.2 mmol), Pd(dppf)Cl2 (0.03 mmol), potassium carbonate (2.5 mmol), 1,4-dioxane / water (10 mL / 2 mL). Heat to 90 degrees Celsius and react for 5 hours. After the reaction is completed, cool to room temperature, filter by suction, wash the filter cake twice with deionized water and twice with ethanol. The obtained crude product is recrystallized and purified twice with ortho-dichlorobenzene to obtain the organic electroluminescent compound M-58 (yield 71%).

[0097] Elemental analysis: C 47 H 29 N3. Theoretical values: C, 86.61; H, 4.49; N, 6.45; O, 2.45; Measured values: C, 86.53; H, 4.59; N, 6.41; HRMS(ESI) m / z [M+H] + : Theoretical value: 651.23; Measured value: 652.24.

[0098] Example 4

[0099] This embodiment provides an organic electroluminescent compound M-66 in a composition of organic materials. The synthesis of the organic electroluminescent compound M-66 specifically includes the following steps:

[0100]

[0101] Take a 100 mL three-necked round-bottom flask, place a magnetic stir bar in it, and connect a reflux condenser above. Under nitrogen protection, successively add raw material A-66 (1 mmol), 2-([1,1':2',1'-terphenyl]-3-yl)-4,6-dichloro-1,3,5-triazine, i.e., B-5 (1.2 mmol), Pd(dppf)Cl2 (0.03 mmol), potassium carbonate (2.5 mmol), 1,4-dioxane / water (10 mL / 2 mL). Heat the mixture to 60 °C and react for 5 hours. After the reaction is completed, cool it to room temperature, quench it with saturated ammonium chloride aqueous solution, extract with ethyl acetate, dry the organic phase with anhydrous magnesium sulfate, remove the solvent using a rotary evaporator, and separate the crude product by column chromatography (ethyl acetate:n-hexane = 1:50) to obtain intermediate M-66-1 (yield 49%).

[0102] Take a 100 mL three-necked round-bottom flask, place a magnetic stir bar in it, and connect a reflux condenser above. Under nitrogen protection, successively add intermediate M-66-1 (1 mmol), 4,4,5,5-tetramethyl-2-(naphtho[2,1-b]benzofuran-2-yl)-1,3,2-dioxaborolane, i.e., C-1 (1.2 mmol), Pd(dppf)Cl2 (0.03 mmol), potassium carbonate (2.5 mmol), 1,4-dioxane / water (10 mL / 2 mL). Heat the mixture to 90 °C and react for 5 hours. After the reaction is completed, cool it to room temperature, filter by suction, wash the filter cake twice with deionized water and twice with ethanol. The obtained crude product is recrystallized and purified twice with o-dichlorobenzene to obtain the organic electroluminescent compound M-66 (yield 57%).

[0103] Elemental analysis: C 53 H 33 N3O. Theoretical values: C, 87.46; H, 4.57; N, 5.77; O, 2.20; Measured values: C, 87.33; H, 4.79; N, 5.68; HRMS(ESI) m / z [M+H] + : Theoretical value: 727.26; Measured value: 728.24.

[0104] The preparation methods of Examples 5-12 are similar to that of Example 1. Specifically, the intermediates, raw materials, and obtained products used in Examples 5-12 are shown in Table 1 below. The preparation method of the intermediate M-n-1 used is the same as that of M-3-1 in Example 1.

[0105] Table 1

[0106]

[0107]

[0108] The characterization data of the products obtained in Examples 5-12 are shown in Table 2 as follows:

[0109] Table 2

[0110]

[0111] Example 13

[0112] This example provides an organic electroluminescent compound M-73. The synthesis of the organic electroluminescent compound M-73 specifically includes the following steps:

[0113]

[0114] Take a 100 mL three-necked round-bottom flask, place a magnetic stir bar and connect a reflux condenser. Under nitrogen protection, sequentially add raw material A-73 (1 mmol), deuterated phenylboronic acid-d5 (1.2 mmol), Pd(dppf)Cl2 (0.03 mmol), potassium carbonate (2.5 mmol), 1,4-dioxane / water (10 mL / 2 mL). Heat the mixture to 60 °C and react for 5 hours. After the reaction is completed, cool to room temperature, quench with saturated ammonium chloride aqueous solution, extract with ethyl acetate, dry the organic phase with anhydrous magnesium sulfate, remove the solvent using a rotary evaporator, and separate the crude product by column chromatography (ethyl acetate: n-hexane = 1:50) to obtain intermediate M-73-1 (yield 54%).

[0115] Take a 100 mL three-necked round-bottom flask, place a magnetic stir bar and connect a reflux condenser. Under nitrogen protection, sequentially add intermediate M-73-1 (1 mmol), 4,4,5,5-tetramethyl-2-(naphtho[2,1-b]benzofuran-2-yl)-1,3,2-dioxaborolane, namely C-1 (1.2 mmol), Pd(dppf)Cl2 (0.03 mmol), potassium carbonate (2.5 mmol), 1,4-dioxane / water (10 mL / 2 mL). Heat the mixture to 90 °C and react for 5 hours. After the reaction is completed, cool to room temperature, filter by suction, wash the filter cake twice with deionized water and twice with ethanol. The obtained crude product is recrystallized and purified twice with o-dichlorobenzene to obtain compound M-73 (yield 67%).

[0116] Elemental analysis: C 41 H 20 D5N3O. Theoretical values: C, 84.80; H, 5.21; N, 7.24; O, 2.76; Measured values: C, 84.90; H, 5.25; N, 7.10; HRMS(ESI) m / z [M+H]+ : Theoretical value: 580.23; Measured value: 581.23.

[0117] Example 14

[0118] This example provides an organic electroluminescent compound M-84. The synthesis of the organic electroluminescent compound M-84 specifically includes the following steps:

[0119]

[0120] Take a 100 mL three-necked round-bottom flask, place a magnetic stir bar in it and connect a reflux condenser above. Under nitrogen protection, sequentially add raw material A-84 (1 mmol), 2,4-dichloro-6-phenyl-1,3,5-triazine, i.e., B-1 (1.2 mmol), Pd(dppf)Cl2 (0.03 mmol), potassium carbonate (2.5 mmol), 1,4-dioxane / water (10 mL / 2 mL). Heat the mixture to 60 °C and react for 5 hours. After the reaction is completed, cool it to room temperature, quench with saturated ammonium chloride aqueous solution, extract with ethyl acetate, dry the organic phase with anhydrous magnesium sulfate, remove the solvent using a rotary evaporator, and separate the crude product by column chromatography (ethyl acetate:n-hexane = 1:50) to obtain intermediate M-84-1 (yield 71%).

[0121] Take a 100 mL three-necked round-bottom flask, place a magnetic stir bar in it and connect a reflux condenser above. Under nitrogen protection, sequentially add intermediate M-84-1 (1 mmol), 4,4,5,5-tetramethyl-2-(naphtho[2,1-b]benzofuran-2-yl-d9)-1,3,2-dioxaborolane, i.e., C-2-D (1.2 mmol), Pd(dppf)Cl2 (0.03 mmol), potassium carbonate (2.5 mmol), 1,4-dioxane / water (10 mL / 2 mL). Heat the mixture to 90 °C and react for 5 hours. After the reaction is completed, cool it to room temperature, perform suction filtration, wash the filter cake twice with deionized water and twice with ethanol. The obtained crude product is recrystallized and purified twice with o-dichlorobenzene to obtain compound M-84 (yield 72%).

[0122] Elemental analysis: C 41 H 16 D9N3O. Theoretical values: C, 84.22; H, 5.86; N, 7.19; O, 2.74; Measured values: C, 84.33; H, 5.94; N, 7.00; HRMS(ESI) m / z [M+H] + : Theoretical value: 584.25; Measured value: 585.25.

[0123] Example 15

[0124] This embodiment provides an organic electroluminescent compound M-96. The synthesis of the organic electroluminescent compound M-96 specifically includes the following steps:

[0125]

[0126] Take a 100 mL three-necked round-bottom flask, place a magnetic stir bar in it and connect a reflux tube above. Under nitrogen protection, sequentially add raw material A-96 (1 mmol), 2,4-dichloro-6-phenyl-1,3,5-triazine, i.e., B-1 (1.2 mmol), Pd(dppf)Cl2 (0.03 mmol), potassium carbonate (2.5 mmol), 1,4-dioxane / water (10 mL / 2 mL). Heat the mixture to 60 °C and react for 5 hours. After the reaction is completed, cool it to room temperature, quench it with saturated ammonium chloride aqueous solution, extract with ethyl acetate, dry the organic phase with anhydrous magnesium sulfate, remove the solvent using a rotary evaporator, and separate the crude product by column chromatography (ethyl acetate:n-hexane = 1:50) to obtain intermediate M-96-1 (yield 80%).

[0127] Take a 100 mL three-necked round-bottom flask, place a magnetic stir bar in it and connect a reflux tube above. Under nitrogen protection, sequentially add intermediate M-96-1 (1 mmol), 4,4,5,5-tetramethyl-2-(naphtho[2,1-b]benzofuran-2-yl)-1,3,2-dioxaborolane, i.e., C-3 (1.2 mmol), Pd(dppf)Cl2 (0.03 mmol), potassium carbonate (2.5 mmol), 1,4-dioxane / water (10 mL / 2 mL). Heat the mixture to 90 °C and react for 5 hours. After the reaction is completed, cool it to room temperature, perform suction filtration, wash the filter cake twice with deionized water and twice with ethanol. The obtained crude product is recrystallized and purified twice with ortho-dichlorobenzene to obtain compound M-96 (yield 72%).

[0128] Elemental analysis: C 41 H 20 D5N3O. Theoretical values: C, 84.80; H, 5.21; N, 7.24; O, 2.76; Measured values: C, 84.90; H, 5.31; N, 7.03; HRMS(ESI) m / z [M+H] + : Theoretical value: 580.23; Measured value: 581.23.

[0129] Example 16

[0130] This embodiment provides an organic electroluminescent compound N-1. The synthesis of the organic electroluminescent compound N-1 specifically includes the following steps:

[0131]

[0132] Synthesis of intermediate N-1-1

[0133] Take a 100 mL three-necked round-bottom flask, place a magnetic stir bar and connect it to a reflux condenser. Under nitrogen protection, sequentially add the raw materials 3-bromodibenzofuran (1 mmol), 3-aminobiphenyl (1.05 mmol), tris(dibenzylideneacetone)palladium (0.03 mmol), Xphos (0.05 mmol), potassium tert-butoxide (2.5 mmol), and toluene (10 mL). Heat the mixture to 110 °C and react for 5 hours. After the reaction is completed, cool it to room temperature, quench it with saturated ammonium chloride aqueous solution, extract with ethyl acetate, dry the organic phase with anhydrous magnesium sulfate, remove the solvent using a rotary evaporator, and separate the crude product by column chromatography (ethyl acetate:n-hexane = 3:50) to obtain intermediate N-1-1 (yield 85%).

[0134] Take a 100 mL three-necked round-bottom flask, place a magnetic stir bar and connect it to a reflux condenser. Under nitrogen protection, sequentially add intermediate N-1-1 (1 mmol), intermediate A (1.1 mmol), tris(dibenzylideneacetone)palladium (0.03 mmol), Sphos (0.05 mmol), potassium tert-butoxide (2.5 mmol), and toluene (10 mL). Heat the mixture to 110 °C and react for 5 hours. After the reaction is completed, cool it to room temperature, filter by suction, wash the filter cake twice with deionized water and twice with ethanol. Recrystallize and purify the obtained crude product twice with toluene and tetrahydrofuran respectively to obtain compound N-1 (yield 65%).

[0135] Elemental analysis: C 45 H 28 Theoretical values for C, H, N2O2: C, 85.97; H, 4.49; N, 4.46; O, 5.09; Measured values: C, 86.07; H, 4.59; N, 4.26; HRMS (ESI) m / z [M+H]+: Theoretical value: 628.22; Measured value: 629.22.

[0136] Example 17

[0137] This example provides an organic electroluminescent compound N-14. The synthesis of the organic electroluminescent compound N-14 specifically includes the following steps:

[0138]

[0139] Synthesis of intermediate N-14-1

[0140] Take a 100 mL three-necked round-bottom flask, place a magnetic stir bar in it and connect a reflux condenser above. Under nitrogen protection, successively add the raw materials: 10-chlorobenzo[b]naphtho[2,3-d]thiophene (1 mmol), aniline (1.05 mmol), tris(dibenzylideneacetone)palladium (0.03 mmol), Xphos (0.05 mmol), potassium tert-butoxide (2.5 mmol), and toluene (10 mL). Heat the mixture to 110 °C and react for 5 hours. After the reaction is completed, cool it to room temperature, quench it with saturated aqueous ammonium chloride solution, extract with ethyl acetate, dry the organic phase with anhydrous magnesium sulfate, remove the solvent using a rotary evaporator, and separate the crude product by column chromatography (ethyl acetate: n-hexane = 3:50) to obtain intermediate N-14-1 (yield 67%). Take a 100 mL three-necked round-bottom flask, place a magnetic stir bar in it and connect a reflux condenser above. Under nitrogen protection, successively add intermediate N-14-1 (1 mmol), intermediate A (1.1 mmol), tris(dibenzylideneacetone)palladium (0.03 mmol), Sphos (0.05 mmol), potassium tert-butoxide (2.5 mmol), and toluene (10 mL). Heat the mixture to 110 °C and react for 5 hours. After the reaction is completed, cool it to room temperature, perform suction filtration, wash the filter cake twice with deionized water and twice with ethanol. Recrystallize the obtained crude product twice with toluene and tetrahydrofuran respectively to obtain compound N-14 (yield 54%).

[0141] Elemental analysis: C 43 H 26 Theoretical values for C, H, N2OS: C, 83.47; H, 4.24; N, 4.53; O, 2.59; S, 5.18; Measured values: C, 83.57; H, 4.34; N, 4.36; S, 5.15; HRMS(ESI) m / z [M+H]+: Theoretical value: 618.18; Measured value: 619.17.

[0142] The compounds in Table 3 can all be synthesized by referring to the above synthesis method. Just change the starting materials to first synthesize intermediate N-n-1, and then carry out a coupling reaction with intermediate A.

[0143] Table 3

[0144]

[0145]

[0146]

[0147] The characterization data of the products obtained in the preparation of Examples 18 - 24 are shown in Table 4

[0148] Table 4

[0149]

[0150] Device Embodiment

[0151] This embodiment provides an organic electroluminescent device, as Figure 1 shown, including an anode 2, a hole injection layer 3, a hole transport layer 4, a light-emitting layer 5, an electron transport layer 6, an electron injection layer 7, and a cathode 8 that are sequentially stacked on a substrate 1. Its device structure is: anode (indium tin oxide (ITO) coated glass substrate) / hole injection layer (HIL) / hole transport layer (HTL) / light-emitting layer (EML) / electron transport layer (ETL) / electron injection layer (EIL) / cathode (Al).

[0152] The materials for manufacturing the organic electroluminescent device are as follows:

[0153]

[0154] The preparation of the above organic electroluminescent device includes the following steps:

[0155] 1) Substrate cleaning:

[0156] The glass substrate coated with transparent ITO is ultrasonically treated in an aqueous cleaning agent (the composition and concentration of the aqueous cleaning agent: glycol-based solvent ≤ 10 wt%, triethanolamine ≤ 1 wt%), then rinsed in deionized water, ultrasonically degreased in a mixed solvent of acetone and ethanol (the volume ratio of acetone to ethanol is 1:1), baked in a clean environment until all moisture is removed, and then cleaned with ultraviolet light and ozone.

[0157] 2) Organic layer preparation:

[0158] Transfer the ITO transparent substrate to an evaporation device and evacuate to 1×10 -6 to 2×10 -4 Pa, and sequentially evaporate a hole injection layer (HIL) / hole transport layer (HTL) / light-emitting layer (EML) / electron transport layer (ETL) / 1 nm electron injection layer (EIL) / thick cathode (Al) on the anode film.

[0159] Among them:

[0160] The material of the hole injection layer (HIL) is a mixture of NDP-9 and HT, and the specific mass ratio is shown in Table 5;

[0161] The material of the hole transport layer (HTL) is shown in Table 5;

[0162] The light-emitting layer (EML) is vacuum-evaporated by co-evaporation. The material of the light-emitting layer includes a host material and a guest material, where the guest material is (piq)2Ir(acac), and the specific material of the host material and its ratio to the guest material are shown in Table 5;

[0163] The materials of the electron transport layer (ETL) are shown in Table 5;

[0164] The material of the electron injection layer (EIL) is LiQ;

[0165] The cathode is aluminum;

[0166] The partial layers, their materials and thicknesses of the organic light-emitting device are shown in Table 5

[0167] Table 5

[0168]

[0169]

[0170]

[0171]

[0172]

[0173]

[0174]

[0175] The examples in the table represent device examples, and the comparative examples in the table are device comparative examples.

[0176] Test examples

[0177] The organic light-emitting devices obtained from Device Examples 1-18 and Comparative Examples 1-25 in the device examples were tested.

[0178] Instrument: The characteristics of the device such as current, voltage, brightness, and emission spectrum were synchronously tested using a PR 650 spectral scanning luminance meter and a Keithley K 2400 digital source meter system;

[0179] Test conditions: Photovoltaic characteristics test conditions: The current density was 10 mA / cm2.

[0180] Lifetime test: The current density was 50 mA / cm2, and the time (in hours) was recorded when the device brightness decreased to 95% of the original brightness.

[0181] The test results of the device performance are shown in Table 6:

[0182] Table 6

[0183]

[0184]

[0185] The examples in the table represent device examples, and the comparative examples in the table are device comparative examples.

[0186] Obviously, the above examples are only illustrations for clear explanation and not limitations on the implementation manners. For those of ordinary skill in the art, other different forms of changes or modifications can be made based on the above description. It is not necessary and impossible to list all implementation manners here. And the obvious changes or modifications derived therefrom are still within the protection scope of the present invention.

Claims

1. A composition of an organic material, characterized in that, The composition of the organic material comprises a first compound and a second compound, and the first compound has a structure represented by formula (1): Wherein, in formula (1), Ar is selected from substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl; The second compound has a structure represented by formula (2): Among them, Ar 1 , Ar 2 are each independently selected from a substituted or unsubstituted C6-C60 aryl group, a substituted or unsubstituted C3-C60 heteroaryl group; The substituents in the substituted C6-C60 aryl and substituted C3-C60 heteroaryl are each independently selected from one or a combination of at least two of deuterium, halogen, cyano, C1-C12 alkyl, C3-C12 cycloalkyl, C6-C30 aryl, C3-C30 heteroaryl, C6-C60 arylamino, and C3-C60 heteroarylamino.

2. The composition of the organic material according to claim 1, characterized in that, Formula (1) is selected from one of the structures shown in I-1 to I-4 below:

3. The composition of the organic material according to claim 1 or 2, characterized in that, Ar is selected from substituted or unsubstituted C6-C60 non-fused aryl, substituted or unsubstituted C3-C60 non-fused heteroaryl; The substituents in the substituted C6-C60 non-fused aryl and substituted C3-C60 non-fused heteroaryl are each independently selected from one or a combination of at least two of deuterium, halogen, cyano, C1-C12 alkyl, C3-C12 cycloalkyl, C6-C30 aryl, C3-C30 heteroaryl, C6-C60 arylamino, and C3-C60 heteroarylamino; Preferably, Ar is selected from substituted or unsubstituted C6-C20 non-fused aryl, substituted or unsubstituted C3-C20 non-fused heteroaryl; The substituents in the substituted C6-C20 non-fused aryl and substituted C3-C20 non-fused heteroaryl are each independently selected from one or a combination of at least two of deuterium, halogen, cyano, C1-C12 alkyl, C3-C12 cycloalkyl, C6-C30 aryl, C3-C30 heteroaryl, C6-C60 arylamino, and C3-C60 heteroarylamino; Ar is selected from substituted or unsubstituted A groups, and the A group is selected from one of the following groups: phenyl, biphenyl, terphenyl; Wherein the substituent in the substituted A group is selected from deuterium, phenyl, naphthyl; Preferably, Ar is selected from phenyl, biphenyl, terphenyl, naphthylphenyl.

4. The composition of the organic material according to any one of claims 1-3, characterized in that The first compound is selected from any one of M-1 to M-104 below:

5. The composition of the organic material according to any one of claims 1-4, characterized in that In formula (2), Ar 1 and Ar 2 are each independently selected from a substituted or unsubstituted C6-C20 aryl group, a substituted or unsubstituted C3-C20 heteroaryl group; Wherein, the substituents in the substituted C6-C20 aryl and substituted C3-C230 heteroaryl are each independently selected from one or a combination of at least two of deuterium, halogen, cyano, C1-C12 alkyl, C3-C12 cycloalkyl, C6-C30 aryl, C3-C30 heteroaryl, C6-C60 arylamino, and C3-C60 heteroarylamino; Preferably, Ar 1 , Ar 2 each independently selected from substituted or unsubstituted A groups, and the A group is selected from phenyl, biphenyl, naphthyl, dibenzofuranyl, dibenzothiophenyl, benzonaphthofuranyl, benzonaphthothiophenyl, terphenyl, phenanthryl; Wherein the substituent of the substituted A group is selected from C1-C6 alkyl, C6-C12 aryl; Preferably, Ar 1 is selected from phenyl, dibenzofuranyl, phenyldibenzofuranyl, dibenzothiophenyl, phenyldibenzothiophenyl, benzonaphthofuranyl, benzonaphthothiophenyl; Ar 2 Selected from phenyl, biphenyl, terphenyl, phenanthryl, naphthyl, phenylnaphthyl, naphthylphenyl.

6. The composition of the organic material according to any one of claims 1-5, characterized in that The second compound is selected from any one of N-1 to N-15 below:

7. The composition of the organic material according to any one of claims 1-6, characterized in that In the material composition, the mass ratio of the first compound to the second compound is 1:9 - 9:1; Preferably, in the material composition, the mass ratio of the first compound to the second compound is 2:8 - 8:2; More preferably, in the material composition, the mass ratio of the first compound to the second compound is 3:7 - 7:3; Even more preferably, in the material composition, the mass ratio of the first compound to the second compound is 4:6 - 6:

4.

8. An organic electroluminescent host material composition, characterized in that, A composition comprising the organic material according to any one of claims 1 - 7.

9. Use of the composition of the organic material according to any one of claims 1 - 7 or the composition of the organic electroluminescent host material according to claim 8 in an optical device; Preferably, the optical device comprises an organic electroluminescent device.

10. An organic electroluminescent device, characterized in that, The organic electroluminescent device comprises an anode and a cathode, and an organic layer disposed between the anode and the cathode. The organic layer comprises the composition of the organic material according to any one of claims 1 - 7 or the composition of the organic electroluminescent host material according to claim 8. Preferably, the light-emitting layer in the organic layer comprises the composition of the organic material according to any one of claims 1 - 7 or the composition of the organic electroluminescent host material according to claim 8.

11. An organic electroluminescent device, characterized in that, An organic electroluminescent device comprising claim 10.

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