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. The present invention provides an organic material composition, the organic material composition comprises a first compound and a second compound, and the first compound and the second compound have the following structures: a formula (1) and a formula (2), the first compound with the structure as shown in the formula (1) and the second compound with the structure as shown in the formula (2) are matched with each other, so that HOMO and LUMO energy levels can be matched with adjacent energy levels, and the organic material composition has relatively high stability and relatively balanced carrier mobility; 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 technology, and in particular to an organic material composition and application thereof. Background Art

[0002] 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 EL device may include a hole injection layer, a hole transport layer, a hole auxiliary layer, a luminescence 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, luminescence auxiliary materials, electron blocking materials, luminescent materials, electron buffer materials, hole blocking materials, electron transport materials, electron injection materials, etc. depending on their functions. In an organic EL 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.

[0003] At present, the functional materials composed of existing organic light-emitting compounds have low stability and unbalanced carrier mobility, which causes the driving voltage of organic electroluminescent diodes to be high and the lifespan to be short, seriously limiting the application of organic electroluminescent diodes. Summary of the Invention

[0004] The purpose of the present invention is to overcome the problems of low stability and unbalanced carrier mobility of functional materials composed of existing organic light-emitting compounds, which cause high driving voltage and short life of organic electroluminescent diodes and seriously limit the application of organic electroluminescent diodes, and further provide an organic electroluminescent material and its application.

[0005] Definitions of substituent terms in this invention:

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

[0007] As used herein, the term "C1-C30 alkyl" refers to a monovalent substituent derived from a straight-chain or branched saturated hydrocarbon having 1 to 30 carbon atoms, examples of which 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 group derived from a monocyclic hydrocarbon or a polycyclic hydrocarbon having 1 to 30 ring main chain carbon atoms, and the cycloalkane may include cyclopropyl, cyclobutyl, adamantyl, and the like.

[0009] In the present invention, aryl and arylene groups include monocyclic, polycyclic or condensed ring aromatic groups, and the rings may be interrupted by short non-aromatic units and may contain spiro structures. Aryl groups include but are not limited to phenyl, biphenyl, terphenyl, naphthyl, phenanthrenyl, anthracenyl, fluorenyl, spirobifluorenyl, etc., and arylene groups include but are not limited to phenylene, biphenylene, terphenylene, naphthylene, phenanthrenyl, anthracenyl, fluorenyl, spirobifluorenyl, etc.

[0010] The heteroaryl and heteroarylene groups in the present invention include monocyclic, polycyclic or condensed ring heteroaryl groups, wherein the rings may be interrupted by short non-aromatic units, and the heteroatoms include nitrogen, oxygen and sulfur. Heteroaryl groups include, but are not limited to, furyl, 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, benzo thiazolyl, benzisothiazolyl, benzisoxazolyl, benzoxazolyl, isoindolyl, indolyl, indazolyl, benzothiadiazolyl, quinolyl, isoquinolyl, cinnolinyl, quinazolinyl, quinoxalinyl, carbazolyl, phenoxazinyl, phenothiazinyl, phenanthridinyl, benzodioxolyl, dihydroacridinyl, and derivatives thereof; heteroarylene groups include but are not limited to furylene, phenylenethio, pyrroleene, thiophene ... yl, imidazolylene, pyrazolylene, thiazolylene, thiadiazolylene, isothiazolylene, isoxazolylene, oxazolylene, oxadiazolylene, triazinylene, tetrazinylene, triazolylene, tetrazolylene, furazolylene, pyridylene, pyrazinylene, pyrimidylene, pyridazinylene, benzofuranylene, benzothiophenylene, isobenzofuranylene, dibenzofuranylene, dibenzothiophenylene, benzimidazolylene oxazolyl, benzothiazolylene, benzoisothiazolylene, benzoisoxazolylene, benzoxazolylene, isoindolyl, indolyl, indazolylene, benzothiadiazolylene, quinolinylene, isoquinolinylene, cinnolinylene, quinazolinylene, quinoxalinylene, carbazolylene, phenoxazinylene, phenothiazinylene, phenanthridinylene, benzodioxolylene, dihydroacridinylene, and derivatives thereof.

[0011] As used herein, 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 that position can be replaced by a substituent. When two or more substituents are present, the two or more substituents may be the same or different.

[0012] As used herein, unless otherwise specified, hydrogen atoms include protium, deuterium, and tritium.

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

[0014] The scheme adopted by the present invention is as follows:

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

[0016]

[0017] Wherein, ring A is a benzene ring;

[0018] Ar is selected from a substituted or unsubstituted C6-C60 aryl group, a substituted or unsubstituted C6-C60 arylamine group, a substituted or unsubstituted C3-C60 heteroarylamine group, or a substituted or unsubstituted C3-C30 heteroaryl group;

[0019] L' is selected from a substituted or unsubstituted C6-C30 arylene group, a substituted or unsubstituted C3-C30 heteroarylene group;

[0020] The second compound has a structure shown in formula (2):

[0021]

[0022] Among them, X 1 -X 12 Each is independently selected from N or CR, and R is selected from hydrogen or deuterium;

[0023] L is selected from a connecting bond, a substituted or unsubstituted C6-C30 arylene group, and a substituted or unsubstituted C3-C30 heteroarylene group;

[0024] R1 and R2 are each independently selected from a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C3-C30 heteroaryl group, a substituted or unsubstituted C6-C60 arylamine group, or a substituted or unsubstituted C3-C60 heteroarylamine group;

[0025] The substituents in the substituted C6-C60 aryl group, substituted C6-C60 arylamine group, substituted C3-C60 heteroarylamine group, substituted C3-C30 heteroaryl group, substituted C6-C30 arylene group, substituted C3-C30 heteroarylene group, substituted C6-C30 aryl group, and substituted C3-C30 heteroaryl group are selected from one or a combination of two of deuterium, halogen, cyano, C1-C6 alkyl group, C3-C30 cycloalkyl group, C6-C30 aryl group, and C3-C30 heteroaryl group.

[0026] Understandably, Ring A in formula (1) can be fused to ring C through positions 1, 2; 2, 3; 3, 4; N can be directly connected to any substitutable position in ring A, ring C, and ring D; L can be connected to any substitutable position in ring B.

[0027] Preferably, in the formula (1), Ar, R1, and R2 are selected from substituted or unsubstituted C6-C25 aryl groups, substituted or unsubstituted C6-C25 arylamine groups, substituted or unsubstituted C3-C25 heteroarylamine groups, and substituted or unsubstituted C3-C20 heteroaryl groups;

[0028] wherein the substituents in the substituted C6-C25 aryl group, the substituted C6-C25 arylamine group, the substituted C3-C25 heteroarylamine group, and the substituted C3-C20 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 arylamine group, and C3-C60 heteroarylamine group;

[0029] Preferably, Ar is selected from substituted or unsubstituted B groups, and B groups are selected from the following groups: phenyl, naphthyl, biphenyl, phenanthrenyl, fluoranthene, phenyl, terphenyl, triphenylene, phenalenyl, phenylnaphthyl, naphthylphenyl, dimethylfluorenyl, phenylmethylfluorenyl, diphenylfluorenyl, pyridyl, pyridylphenyl, phenylpyridyl, spirobifluorenyl, benzodimethylfluorenyl, benzodiphenylfluorenyl, benzospirobifluorenyl, dibenzofuranyl, benzonaphthofuranyl, benzonaphthothienyl, spiro[fluorene-9,9'-xanthenyl]yl, phenylmethylfluorenyl, dinaphthofuranyl, dinaphthothienyl, dibenzothienyl, N,N-diphenylanilinoyl;

[0030] wherein the substituent of the substituted B group is 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 arylamine, and C3-C60 heteroarylamine;

[0031] Preferably, in the formula (2), R1 and R2 are each independently selected from a substituted or unsubstituted A group, and the A group is selected from the following groups: phenyl, naphthyl, biphenyl, terphenyl, phenanthrenyl, triphenylene, fluorenyl, dimethylfluorenyl, spirobifluorenyl, fluoranthenyl, diphenylfluorenyl, benzodimethylfluorenyl, benzodiphenylfluorenyl, benzospirobifluorenyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, phenylcarbazolyl, bipyridyl, pyrimidinyl, triazinyl;

[0032] Wherein, the substituent of the substituted A group is 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 aromatic amine, and C3-C60 heteroaromatic amine.

[0033] Preferably, in the formula (1), Ar is selected from phenyl, naphthyl, biphenyl, phenyl, phenanthrenyl, terphenyl, phenylnaphthyl, naphthylphenyl, dimethylfluorenyl, diphenylfluorenyl, spirobifluorenyl, phenanthrenyl, dibenzofuranyl, benzonaphthofuranyl, N,N-diphenylanilino;

[0034] Preferably, in the formula (2), R1 and R2 are each independently selected from phenyl, naphthyl, biphenyl, terphenyl, phenanthrenyl, triphenylene, fluorenyl, dimethylfluorenyl, spirobifluorenyl, fluoranthenyl, diphenylfluorenyl, benzodimethylfluorenyl, benzodiphenylfluorenyl, benzospirobifluorenyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, phenylcarbazolyl, bipyridyl, pyrimidinyl, triazine.

[0035] Preferably, L' is selected from substituted or unsubstituted C6-C15 arylene;

[0036] wherein the substituents in the substituted C6-C15 arylene group are independently selected from one or a combination of at least two of deuterium, halogen, and C1-C62 alkyl;

[0037] Preferably, L' is selected from phenylene, biphenylene, naphthylene;

[0038] Preferably, L' is selected from phenylene and naphthylene;

[0039] Preferably, in the formula (2), L is a single bond;

[0040] Preferably, X1-X 12 Each independently selected from CR;

[0041] or, X1-X 12 Wherein X2 is selected from N, and the others are independently selected from CR;

[0042] or, X1-X 12 wherein X5 is selected from N, and the others are independently selected from CR;

[0043] or, X1-X 12 wherein X8 is selected from N, and the others are independently selected from CR;

[0044] or, X1-X 12 wherein X9 is selected from N, and the others are independently selected from CR.

[0045] Preferably, the first compound has the structure shown in any one of N-1 to N-208 below:

[0046]

[0047]

[0048]

[0049]

[0050]

[0051]

[0052]

[0053]

[0054] Preferably, the second compound has the structure shown in any one of M-1 to M-348 below:

[0055]

[0056]

[0057]

[0058]

[0059]

[0060]

[0061]

[0062] Preferably, in the material composition, the mass ratio of the first compound to the second compound is 1:9-9:1;

[0063] Preferably, in the material composition, the mass ratio of the first compound to the second compound is 2:8-8:2;

[0064] More preferably, in the material composition, the mass ratio of the first compound to the second compound is 3:7-7:3;

[0065] Further preferably, in the material composition, the mass ratio of the first compound to the second compound is 4:6-6:4.

[0066] The present invention provides an organic electroluminescent host material composition, comprising the organic material composition described above.

[0067] The present invention provides the use of the above-mentioned organic material composition or the above-mentioned organic electroluminescent host material composition in an optical device;

[0068] Preferably, the optical device comprises an organic electroluminescent device.

[0069] The present invention provides an organic electroluminescent device, comprising an anode and a cathode, and an organic layer disposed between the anode and the cathode, wherein the organic layer comprises the organic material composition or the organic electroluminescent host material composition described above;

[0070] Preferably, the organic layer includes a light-emitting layer, and the light-emitting layer includes the above-mentioned organic material composition or the above-mentioned organic electroluminescent host material composition.

[0071] Preferably, the organic layer comprises 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 stacked in sequence from the anode side to the cathode side;

[0072] Preferably, the material of the light-emitting layer comprises a host material and a guest material, and the host material comprises the organic material composition described above or the organic electroluminescent host material composition described above.

[0073] Preferably, the guest material includes a phosphorescent dopant, and the phosphorescent dopant includes a complex containing a transition metal.

[0074] The present invention provides an organic electroluminescent device, comprising the organic electroluminescent device described above.

[0075] The term "organic electroluminescent material" disclosed in the present invention means a material that can be used in an organic electroluminescent device and can include 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 assist material, a luminescence assist material, an electron blocking material, a luminescent material (containing 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.

[0076] An organic electroluminescent material disclosed in the present invention may include one organic electroluminescent material, or may include multiple organic electroluminescent materials, wherein multiple organic electroluminescent materials mean a material comprising a combination of at least two organic electroluminescent materials, and the material may be included in any layer constituting an organic electroluminescent device. It may mean both a material included before (e.g., before vapor deposition) an organic electroluminescent device and a material included after (e.g., after vapor deposition) an organic electroluminescent device. For example, a material may be a combination of at least two compositions, and the composition 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. Two compositions in a plurality of organic electroluminescent materials 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 "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 being included in an organic electroluminescent device (for example, before vapor deposition) and a material after being included in an organic electroluminescent device (for example, after vapor deposition). The composition disclosed in the present invention may be included in any light-emitting layer constituting an organic electroluminescent device. Two or more compounds of the multiple host materials included in the composition disclosed in the present invention may be included in one light-emitting layer, or may be respectively 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 simultaneously by separate co-evaporation.

[0078] In the present invention, the first compound can be prepared by the following synthetic route, comprising the following steps:

[0079] 1. Synthesis of intermediate Nn-A: The reaction materials Nn-1 and Nn-2 were subjected to Suzuki cross-coupling reaction, and the reaction formula is as follows:

[0080]

[0081] 2. Synthesis of Compound Nn: Intermediates Nn-A and Nn-B were subjected to a Buchwald-Hartwig cross-coupling reaction, as shown in the following reaction formula:

[0082]

[0083] Beneficial effects of the present invention:

[0084] The organic material composition of the present invention comprises a first compound and a second compound, wherein the first compound has a structure represented by formula (1) and the second compound has a structure represented by formula (2); the first compound having a structure represented by formula (1) and the second compound having a structure represented by formula (2) cooperate with each other to facilitate matching of HOMO and LUMO energy levels with adjacent energy levels, thereby enabling the organic material composition to obtain higher stability and more balanced carrier mobility, thereby enabling an organic electroluminescent device comprising the material to have a more excellent lifespan, as well as a lower driving voltage and higher efficiency. BRIEF DESCRIPTION OF THE DRAWINGS

[0085] In order to more clearly illustrate the specific embodiments of the present invention or the technical solutions in the prior art, the following briefly introduces the drawings required for use in the specific embodiments or the description of the prior art. Obviously, the drawings described below are some embodiments of the present invention. For ordinary technicians in this field, other drawings can be obtained based on these drawings without paying any creative work.

[0086] Figure 1 This is a structural diagram of an organic electroluminescent device in an embodiment of the device of the present invention;

[0087] 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. DETAILED DESCRIPTION

[0088] The following examples are provided for a better understanding of the present invention and are not intended to limit the best mode of implementation. They do not limit the content and scope of protection of the present invention. Any product identical or similar to the present invention obtained by anyone under the guidance of the present invention or by combining the features of the present invention with other prior arts shall fall within the scope of protection of the present invention.

[0089] If no specific experimental steps or conditions are specified in the examples, the conventional experimental steps or conditions described in the literature in this field can be used. If the manufacturer of the reagents or instruments is not specified, they are all commercially available conventional reagents.

[0090] Example 1

[0091] This embodiment provides an oxazole organic compound N-1 containing benzonaphthofuran. The synthesis of the oxazole organic compound N-1 containing benzonaphthofuran specifically includes the following steps:

[0092]

[0093] Synthesis of intermediate N1-A

[0094] After nitrogen replacement to a three-mouth reaction flask equipped with mechanical stirring, a thermometer, and a condenser tube, raw material 10gN1-1 (36.63mmol), 5.72g N1-2 (36.63mmol), 0.85g tetrakis triphenylphosphine palladium (0.73mmol), 10.11g potassium carbonate (73.27mmol), 70mL toluene, 30mL ethanol, and 30mL water were added sequentially. The mixture was stirred at 65°C for 2 hours. After the reaction was complete, the organic layer was extracted with ethyl acetate (EA), and residual moisture was removed by using anhydrous sodium sulfate, the residue was dried, and purified by column chromatography to obtain 10.06g of compound N1-A (90% yield).

[0095] Synthesis of intermediate N1-B

[0096] After nitrogen replacement of a three-necked reaction flask equipped with a mechanical stirrer, a thermometer, and a condenser, intermediate 10 g N1-A (32.78 mmol), 3.1 g N1-3 (32.78 mmol), 0.6 g tris (dibenzylideneacetone) dipalladium (0.66 mmol), 0.67 g 2-dicyclohexylphosphine-2', 6'-dimethoxybiphenyl (1.64 mmol), 6.3 g sodium tert-butoxide (65.56 mmol), 100 mL of toluene were added sequentially, and the mixture was stirred at reflux for 3 hours at 110 ° C. After the reaction was completed, the organic layer was extracted with ethyl acetate (EA), and residual moisture was removed by using anhydrous sodium sulfate, the residue was dried and purified by column chromatography to obtain 8.31 g of compound N1-B (yield 82%).

[0097] Synthesis of compound N-1

[0098] After nitrogen replacement of a three-necked reaction flask equipped with a mechanical stirrer, a thermometer, and a condenser, intermediate 8.30 g N1-B (26.85 mmol), 7.95 g N1-4 (26.85 mmol), 0.49 g tris (dibenzylideneacetone) dipalladium (0.54 mmol), 0.55 g 2-dicyclohexylphosphine-2', 6'-dimethoxybiphenyl (1.34 mmol), 5.16 g sodium tert-butoxide (53.70 mmol), 100 mL of toluene were added sequentially, and the mixture was refluxed at 110 ° C for 3 hours. After the reaction was completed, the organic layer was extracted with ethyl acetate (EA), and residual moisture was removed by using anhydrous sodium sulfate, the residue was dried and purified by column chromatography to obtain 11.80 g of oxazole organic compound N-1 containing benzonaphthofuran (yield 76%).

[0099] Elemental analysis: C 41 H 26 N2O2; theoretical value: C, 85.10; H, 4.53; N, 4.84; O, 5.53; found value: C, 85.12; H, 4.52; N, 4.83; HRMS (ESI) m / z [M+H] +: theoretical value: 578.20; found value: 579.21.

[0100] Example 2

[0101] This embodiment provides an oxazole organic compound N-6 containing benzonaphthofuran. The synthesis of the oxazole organic compound N-6 containing benzonaphthofuran specifically includes the following steps:

[0102]

[0103] After nitrogen replacement to a three-necked reaction flask equipped with mechanical stirring, a thermometer, and a condenser, intermediate 10gN1-A (32.78mmol), 10.92g N6-3 (32.78mmol), 0.6g tris (dibenzylideneacetone) dipalladium (0.66mmol), 0.67g2-dicyclohexylphosphine-2', 6'-dimethoxybiphenyl (1.64mmol), 6.3g sodium tert-butoxide (65.56mmol), 100mL of toluene were added sequentially, and the mixture was refluxed at 110°C for 3 hours. After the reaction was complete, the organic layer was extracted with ethyl acetate (EA), and residual moisture was removed by using anhydrous sodium sulfate, the residue was dried, and purified by column chromatography to obtain 14.41g of compound N6-B (yield 73%).

[0104] After nitrogen substitution in a three-necked reaction flask equipped with a mechanical stirrer, a thermometer, and a condenser, 10 g of intermediate N6-B (16.60 mmol), 4.91 g of N1-4 (16.60 mmol), 0.30 g of tris (dibenzylideneacetone) dipalladium (0.33 mmol), 0.34 g of 2-dicyclohexylphosphine-2', 6'-dimethoxybiphenyl (0.83 mmol), 3.19 g of sodium tert-butoxide (33.21 mmol), and 100 mL of toluene were added sequentially, and the mixture was refluxed at 110 ° C for 3 hours. After the reaction was completed, the organic layer was extracted with ethyl acetate (EA), and residual moisture was removed by using anhydrous sodium sulfate, the residue was dried, and purified by column chromatography to obtain 9.24 g of oxazole organic compound N-6 containing benzonaphthofuran (yield 68%).

[0105] Elemental analysis: C 60 H 38 N2O2; theoretical value: C, 88.00; H, 4.68; N, 3.42; O, 3.91; found value: C, 88.01; H, 4.68; N, 3.41; HRMS (ESI) m / z [M+H] +: theoretical value: 818.29; found value: 819.28.

[0106] Example 3

[0107] This embodiment provides an oxazole organic compound N-18 containing benzonaphthofuran. The synthesis of the oxazole organic compound N-18 containing benzonaphthofuran specifically includes the following steps:

[0108]

[0109] After nitrogen replacement of a three-necked reaction flask equipped with mechanical stirring, a thermometer, and a condenser, intermediate 10gN1-A (32.78mmol), 8.53gN18-3 (32.78mmol), 0.60g tris (dibenzylideneacetone) dipalladium (0.66mmol), 0.67g 2-dicyclohexylphosphine-2', 6'-dimethoxybiphenyl (1.64mmol), 6.3g sodium tert-butoxide (65.56mmol), 100mL of toluene were added sequentially, and the mixture was refluxed at 110°C for 3 hours. After the reaction was completed, the organic layer was extracted with ethyl acetate (EA), and residual moisture was removed by using anhydrous sodium sulfate, the residue was dried and purified by column chromatography to obtain 13.19g of compound N18-B (yield 76%).

[0110] After nitrogen replacement of a three-necked reaction flask equipped with a mechanical stirrer, a thermometer, and a condenser, 10 g of N18-B (18.90 mmol) was added, followed by 5.59 g of N18-4 (18.90 mmol), 0.35 g of tris (dibenzylideneacetone) dipalladium (0.38 mmol), 0.39 g of 2-dicyclohexylphosphine-2', 6'-dimethoxybiphenyl (0.94 mmol), 3.63 g of sodium tert-butoxide (37.79 mmol), and 100 mL of toluene, and the mixture was stirred at reflux for 3 hours at 110 ° C. After the reaction was completed, the organic layer was extracted with ethyl acetate (EA), and residual moisture was removed by using anhydrous sodium sulfate, the residue was dried, and purified by column chromatography to obtain 10.70 g of an organic electroluminescent compound N-18 (yield 76%).

[0111] Elemental analysis: C 53 H 35 N3O2; theoretical value: C, 85.35; H, 4.73; N, 5.63; O, 4.29; found value: C, 85.37; H, 4.72; N, 5.62; HRMS (ESI) m / z [M+H] +: theoretical value: 745.27; found value: 746.26.

[0112] Example 4

[0113] This embodiment provides an oxazole organic compound N-30 containing benzonaphthofuran. The synthesis of the oxazole organic compound N-30 containing benzonaphthofuran specifically includes the following steps:

[0114]

[0115] After nitrogen substitution in a three-necked reaction flask equipped with a mechanical stirrer, a thermometer, and a condenser, intermediate 10 g of N1-A (32.78 mmol), 5.54 g of N30-3 (32.78 mmol), 0.60 g of tris (dibenzylideneacetone) dipalladium (0.66 mmol), 0.67 g of 2-dicyclohexylphosphine-2', 6'-dimethoxybiphenyl (1.64 mmol), 6.30 g of sodium tert-butoxide (65.56 mmol), and 100 mL of toluene were added sequentially, and the mixture was stirred at reflux for 3 hours at 110 ° C. After the reaction was completed, the organic layer was extracted with ethyl acetate (EA), and residual moisture was removed by using anhydrous sodium sulfate, the residue was dried, and purified by column chromatography to obtain 11.49 g of compound N30-B (yield 80%).

[0116] After nitrogen substitution in a three-necked reaction flask equipped with a mechanical stirrer, a thermometer, and a condenser, 10 g of intermediate N30-B (22.82 mmol), 6.75 g of N30-4 (22.82 mmol), 0.42 g of tris (dibenzylideneacetone) dipalladium (0.46 mmol), 0.47 g of 2-dicyclohexylphosphine-2', 6'-dimethoxybiphenyl (1.14 mmol), 4.39 g of sodium tert-butoxide (45.64 mmol), and 100 mL of toluene were added sequentially, and the mixture was refluxed at 110 ° C for 3 hours. After the reaction was completed, the organic layer was extracted with ethyl acetate (EA), and residual moisture was removed by using anhydrous sodium sulfate, the residue was dried, and purified by column chromatography to obtain 10.75 g of oxazole organic compound N-30 containing benzonaphthofuran (yield 72%).

[0117] Elemental analysis: C 47 H 30 N2O2; theoretical value: C, 86.22; H, 4.62; N, 4.28; O, 4.89; found value: C, 86.20; H, 4.63; N, 4.29; HRMS (ESI) m / z [M+H] +: theoretical value: 654.23; found value: 654.24.

[0118] Example 5

[0119] This embodiment provides an oxazole organic compound N-45 containing benzonaphthofuran. The synthesis of the oxazole organic compound N-45 containing benzonaphthofuran specifically includes the following steps:

[0120]

[0121] After nitrogen replacement of a three-necked reaction flask equipped with a mechanical stirrer, a thermometer, and a condenser, intermediate 10gN1-A (32.78mmol), 7.18gN45-3 (32.78mmol), 0.60g tris (dibenzylideneacetone) dipalladium (0.66mmol), 0.67g 2-dicyclohexylphosphine-2', 6'-dimethoxybiphenyl (1.64mmol), 6.30g sodium tert-butoxide (65.56mmol), 100mL of toluene were added sequentially, and the mixture was refluxed at 110°C for 3 hours. After the reaction was completed, the organic layer was extracted with ethyl acetate (EA), and residual moisture was removed by using anhydrous sodium sulfate, the residue was dried and purified by column chromatography to obtain 12.16g of compound N45-B (yield 76%).

[0122] After nitrogen substitution in a three-necked reaction flask equipped with a mechanical stirrer, a thermometer, and a condenser, intermediate 7.50 g N45-B (15.36 mmol), 3.87 g N45-4 (15.36 mmol), 0.28 g tris (dibenzylideneacetone) dipalladium (0.31 mmol), 0.31 g 2-dicyclohexylphosphine-2', 6'-dimethoxybiphenyl (0.77 mmol), 2.95 g sodium tert-butoxide (30.73 mmol), 80 mL of toluene were added sequentially, and the mixture was refluxed at 110 ° C for 3 hours. After the reaction was completed, the organic layer was extracted with ethyl acetate (EA), and residual moisture was removed by using anhydrous sodium sulfate, the residue was dried, and purified by column chromatography to obtain 8.22 g of benzonaphthofuran-containing oxazole organic compound N-45 (yield 76%).

[0123] Elemental analysis: C 51 H 32 N2O2; theoretical value: C, 86.91; H, 4.58; N, 3.97; O, 4.54; found value: C, 86.93; H, 4.57; N, 3.96; HRMS (ESI) m / z [M+H] +: theoretical value: 704.25; found value: 705.26.

[0124] Example 6

[0125] This embodiment provides an oxazole organic compound N-72 containing benzonaphthofuran. The synthesis of the oxazole organic compound N-72 containing benzonaphthofuran specifically includes the following steps:

[0126]

[0127] Synthesis of intermediate N72-A

[0128] After nitrogen replacement to a three-mouth reaction flask equipped with mechanical stirring, a thermometer, and a condenser tube, raw material 10gN1-1 (36.63mmol), 5.72gN72-2 (36.63mmol), 0.85g tetrakis triphenylphosphine palladium (0.73mmol), 10.11g potassium carbonate (73.27mmol), 70mL toluene, 30mL ethanol, and 30mL water were added sequentially. The mixture was stirred at 65°C for 2 hours. After the reaction was complete, the organic layer was extracted with ethyl acetate (EA), and residual moisture was removed by using anhydrous sodium sulfate, the residue was dried, and purified by column chromatography to obtain 9.50g of compound N72-A (yield 85%).

[0129] Synthesis of intermediate N72-B

[0130] After nitrogen substitution in a three-necked reaction flask equipped with a mechanical stirrer, a thermometer, and a condenser, 9.50 g of intermediate N72-A (31.14 mmol), 6.82 g of N73-3 (31.14 mmol), 0.57 g of tris (dibenzylideneacetone) palladium (0.62 mmol), 0.64 g of 2-dicyclohexylphosphine-2', 6'-dimethoxybiphenyl (1.56 mmol), 5.99 g of sodium tert-butoxide (62.28 mmol), and 100 mL of toluene were added sequentially, and the mixture was refluxed at 110 ° C for 3 hours. After the reaction was completed, the organic layer was extracted with ethyl acetate (EA), and residual moisture was removed by using anhydrous sodium sulfate, the residue was dried, and purified by column chromatography to obtain 11.10 g of compound N72-B (yield 73%).

[0131] After nitrogen substitution in a three-necked reaction flask equipped with a mechanical stirrer, a thermometer, and a condenser, 10 g of intermediate N72-B (20.48 mmol), 6.06 g of N72-4 (20.48 mmol), 0.37 g of tris (dibenzylideneacetone) dipalladium (0.41 mmol), 0.42 g of 2-dicyclohexylphosphine-2', 6'-dimethoxybiphenyl (1.02 mmol), 3.94 g of sodium tert-butoxide (40.97 mmol), and 100 mL of toluene were added sequentially, and the mixture was refluxed at 110 ° C for 3 hours. After the reaction was completed, the organic layer was extracted with ethyl acetate (EA), and residual moisture was removed by using anhydrous sodium sulfate, the residue was dried, and purified by column chromatography to obtain 10.82 g of oxazole organic compound N-72 containing benzonaphthofuran (yield 75%).

[0132] Elemental analysis: C51H32N2O2; theoretical value: C, 86.91; H, 4.58; N, 3.97; O, 4.54; found value: C, 86.93; H, 4.57; N, 3.96; HRMS (ESI) m / z [M+H] +: theoretical value: 704.25; found value: 705.26.

[0133] Example 7

[0134] This embodiment provides an oxazole organic compound N-95 containing benzonaphthofuran. The synthesis of the oxazole organic compound N-95 containing benzonaphthofuran specifically includes the following steps:

[0135]

[0136] After nitrogen replacement to a three-mouth reaction flask equipped with mechanical stirring, a thermometer, and a condenser, raw material 10gN1-1 (36.63mmol), 5.72gN95-2 (36.63mmol), 0.85g tetrakis triphenylphosphine palladium (0.73mmol), 10.11g potassium carbonate (73.27mmol), 70mL toluene, 30mL ethanol, and 30mL water were added sequentially. The mixture was stirred at 65 ° C for 2 hours. After the reaction was completed, the organic layer was extracted with ethyl acetate (EA), and residual moisture was removed by using anhydrous sodium sulfate, the residue was dried and purified by column chromatography to obtain 9.28g of compound N95-A (yield 83%).

[0137] After nitrogen substitution in a three-necked reaction flask equipped with a mechanical stirrer, a thermometer, and a condenser, 9.28 g of intermediate N95-A (30.42 mmol), 6.67 g of N72-3 (30.42 mmol), 0.56 g of tris (dibenzylideneacetone) palladium (0.61 mmol), 0.62 g of 2-dicyclohexylphosphine-2', 6'-dimethoxybiphenyl (1.52 mmol), 5.85 g of sodium tert-butoxide (60.84 mmol), and 100 mL of toluene were added sequentially, and the mixture was refluxed at 110 ° C for 3 hours. After the reaction was completed, the organic layer was extracted with ethyl acetate (EA), and residual moisture was removed by using anhydrous sodium sulfate, the residue was dried, and purified by column chromatography to obtain 10.69 g of compound N95-B (yield 72%).

[0138] After nitrogen substitution in a three-necked reaction flask equipped with a mechanical stirrer, a thermometer, and a condenser, 10 g of intermediate N95-B (20.48 mmol), 6.06 g of N95-4 (20.48 mmol), 0.37 g of tris (dibenzylideneacetone) dipalladium (0.41 mmol), 0.42 g of 2-dicyclohexylphosphine-2', 6'-dimethoxybiphenyl (1.02 mmol), 3.94 g of sodium tert-butoxide (40.97 mmol), and 100 mL of toluene were added sequentially, and the mixture was refluxed at 110 ° C for 3 hours. After the reaction was completed, the organic layer was extracted with ethyl acetate (EA), and residual moisture was removed by using anhydrous sodium sulfate, the residue was dried, and purified by column chromatography to obtain 10.10 g of oxazole organic compound N-95 containing benzonaphthofuran (yield 70%).

[0139] Elemental analysis: C 51 H 32N2O2; theoretical value: C, 86.91; H, 4.58; N, 3.97; O, 4.54; found value: C, 86.90; H, 4.58; N, 3.98; HRMS (ESI) m / z [M+H] +: theoretical value: 704.25; found value: 705.26.

[0140] Example 8

[0141] This embodiment provides an oxazole organic compound N-134 containing benzonaphthofuran. The synthesis of the oxazole organic compound N-134 containing benzonaphthofuran specifically includes the following steps:

[0142]

[0143] After nitrogen substitution in a three-necked reaction flask equipped with a mechanical stirrer, a thermometer, and a condenser, 8.60 g of intermediate N18-B (16.25 mmol), 4.10 g of N134-4 (16.25 mmol), 0.30 g of tris (dibenzylideneacetone) dipalladium (0.33 mmol), 0.33 g of 2-dicyclohexylphosphine-2', 6'-dimethoxybiphenyl (0.81 mmol), 3.12 g of sodium tert-butoxide (32.50 mmol), and 100 mL of toluene were added sequentially, and the mixture was refluxed at 110 ° C for 3 hours. After the reaction was completed, the organic layer was extracted with ethyl acetate (EA), and residual moisture was removed by using anhydrous sodium sulfate, the residue was dried, and purified by column chromatography to obtain 9.20 g of benzonaphthofuran-containing oxazole organic compound N-134 (yield 76%).

[0144] Elemental analysis: C 53 H 35 N3O2; theoretical value: C, 85.35; H, 4.73; N, 5.63; O, 4.29; found value: C, 85.33; H, 4.74; N, 5.64; HRMS (ESI) m / z [M+H] +: theoretical value: 745.27; found value: 746.29.

[0145] Example 9

[0146] This embodiment provides an oxazole organic compound N-148 containing benzonaphthofuran. The synthesis of the oxazole organic compound N-148 containing benzonaphthofuran specifically includes the following steps:

[0147]

[0148] After nitrogen replacement of a three-necked reaction flask equipped with a mechanical stirrer, a thermometer, and a condenser, intermediate 10gN73-A (32.78mmol), 5.54g N30-3 (32.78mmol), 0.60g tris (dibenzylideneacetone) dipalladium (0.66mmol), 0.67g 2-dicyclohexylphosphine-2', 6'-dimethoxybiphenyl (1.64mmol), 6.3g sodium tert-butoxide (65.56mmol), 100mL of toluene were added sequentially, and the mixture was refluxed at 110°C for 3 hours. After the reaction was completed, the organic layer was extracted with ethyl acetate (EA), and residual moisture was removed by using anhydrous sodium sulfate, the residue was dried, and purified by column chromatography to obtain 11.34g of compound N148-B (yield 79%).

[0149] After nitrogen substitution in a three-necked reaction flask equipped with a mechanical stirrer, a thermometer, and a condenser, 10 g of intermediate N148-B (22.82 mmol), 6.57 g of N18-4 (22.82 mmol), 0.42 g of tris (dibenzylideneacetone) dipalladium (0.46 mmol), 0.47 g of 2-dicyclohexylphosphine-2', 6'-dimethoxybiphenyl (1.14 mmol), 4.39 g of sodium tert-butoxide (45.64 mmol), and 100 mL of toluene were added sequentially, and the mixture was refluxed at 110 ° C for 3 hours. After the reaction was completed, the organic layer was extracted with ethyl acetate (EA), and residual moisture was removed by using anhydrous sodium sulfate, the residue was dried, and purified by column chromatography to obtain 11.20 g of oxazole organic compound N-148 containing benzonaphthofuran (yield 75%).

[0150] Elemental analysis: C 47 H 30 N2O2; theoretical value: C, 86.22; H, 4.62; N, 4.28; O, 4.89; found value: C, 86.22; H, 4.62; N, 4.28; HRMS (ESI) m / z [M+H] +: theoretical value: 654.23; found value: 655.21.

[0151] Example 10

[0152] This embodiment provides an organic electroluminescent compound N-173. The synthesis of the organic electroluminescent compound N-173 specifically includes the following steps:

[0153]

[0154] After nitrogen replacement of a three-necked reaction flask equipped with a mechanical stirrer, a thermometer, and a condenser, intermediate 10gN73-A (32.78mmol), 4.69g N173-3 (32.78mmol), 0.60g tris (dibenzylideneacetone) dipalladium (0.66mmol), 0.67g 2-dicyclohexylphosphine-2', 6'-dimethoxybiphenyl (1.64mmol), 6.30g sodium tert-butoxide (65.56mmol), 100mL of toluene were added sequentially, and the mixture was refluxed at 110°C for 3 hours. After the reaction was completed, the organic layer was extracted with ethyl acetate (EA), and residual moisture was removed by using anhydrous sodium sulfate, the residue was dried, and purified by column chromatography to obtain 9.73g of compound N173-B (yield 72%).

[0155] After nitrogen substitution in a three-necked reaction flask equipped with a mechanical stirrer, a thermometer, and a condenser, 9.70 g of intermediate N173-B (23.53 mmol), 6.97 g of N173-4 (23.53 mmol), 0.43 g of tris (dibenzylideneacetone) dipalladium (0.47 mmol), 0.48 g of 2-dicyclohexylphosphine-2', 6'-dimethoxybiphenyl (1.18 mmol), 4.52 g of sodium tert-butoxide (47.07 mmol), and 100 mL of toluene were added sequentially, and the mixture was refluxed at 110 ° C for 3 hours. After the reaction was completed, the organic layer was extracted with ethyl acetate (EA), and residual moisture was removed by using anhydrous sodium sulfate, the residue was dried, and purified by column chromatography to obtain 10.35 g of compound N-173 (yield 70%).

[0156] Elemental analysis: C 45 H 28 N2O2; theoretical value: C, 85.97; H, 4.49; N, 4.46; O, 5.09; found value: C, 85.96; H, 4.48; N, 4.48; HRMS (ESI) m / z [M+H] +: theoretical value: 628.22; found value: 629.24.

[0157] Example 11

[0158] This embodiment provides an organic electroluminescent compound N-182. The synthesis of the organic electroluminescent compound N-182 specifically includes the following steps:

[0159] After nitrogen replacement to a three-mouth reaction flask equipped with mechanical stirring, a thermometer, and a condenser tube, raw material 10gN182-1 (36.63mmol), 5.72g N182-2 (36.63mmol), 0.85g tetrakis triphenylphosphine palladium (0.73mmol), 10.11g potassium carbonate (73.27mmol), 70mL toluene, 30mL ethanol, and 30mL water were added sequentially. The mixture was stirred at 65°C for 2 hours. After the reaction was complete, the organic layer was extracted with ethyl acetate (EA), and residual moisture was removed by using anhydrous sodium sulfate, the residue was dried, and purified by column chromatography to obtain 8.94g of compound N182-A (80% yield).

[0160] After nitrogen replacement of a three-necked reaction flask equipped with a mechanical stirrer, a thermometer, and a condenser, intermediate 8.94gN182-A (29.31mmol), 4.96gN30-3 (29.31mmol), 0.54g tris (dibenzylideneacetone) palladium (0.59mmol), 0.60g 2-dicyclohexylphosphine-2', 6'-dimethoxybiphenyl (1.47mmol), 5.63g sodium tert-butoxide (58.61mmol), 100mL of toluene were added sequentially, and the mixture was refluxed at 110°C for 3 hours. After the reaction was completed, the organic layer was extracted with ethyl acetate (EA), and residual moisture was removed by using anhydrous sodium sulfate, the residue was dried and purified by column chromatography to obtain 10.01g of compound N182-B (yield 78%).

[0161] After nitrogen substitution in a three-necked reaction flask equipped with a mechanical stirrer, a thermometer, and a condenser, intermediate 10.01 g N182-B (22.85 mmol), 6.76 g N1-4 (22.85 mmol), 0.42 g tris (dibenzylideneacetone) dipalladium (0.46 mmol), 0.47 g 2-dicyclohexylphosphine-2', 6'-dimethoxybiphenyl (1.14 mmol), 4.39 g sodium tert-butoxide (45.69 mmol), and 100 mL of toluene were added sequentially, and the mixture was refluxed at 110 ° C for 3 hours. After the reaction was completed, the organic layer was extracted with ethyl acetate (EA), and residual moisture was removed by using anhydrous sodium sulfate, the residue was dried, and purified by column chromatography to obtain 11.21 g of compound N-182 (yield 75%).

[0162] Elemental analysis: C 47 H 30 N2O2; theoretical value: C, 86.22; H, 4.62; N, 4.28; O, 4.89; found value: C, 86.24; H, 4.61; N, 4.27; HRMS (ESI) m / z [M+H] +: theoretical value: 654.23; found value: 654.21.

[0163] Example 12

[0164]

[0165] After nitrogen substitution in a three-necked reaction flask equipped with a mechanical stirrer, a thermometer, and a condenser, intermediate 8.94gN182-A (29.31mmol), 4.96gN173-3 (29.31mmol), 0.54g tris (dibenzylideneacetone) palladium (0.59mmol), 0.60g 2-dicyclohexylphosphine-2', 6'-dimethoxybiphenyl (1.47mmol), 5.63g sodium tert-butoxide (58.61mmol), 100mL of toluene were added sequentially, and the mixture was refluxed at 110°C for 3 hours. After the reaction was completed, the organic layer was extracted with ethyl acetate (EA), and residual moisture was removed by using anhydrous sodium sulfate, the residue was dried, and purified by column chromatography to obtain 10.01g of compound N207-B (yield 78%).

[0166] After nitrogen substitution in a three-necked reaction flask equipped with a mechanical stirrer, a thermometer, and a condenser, intermediate 10 g N207-B (24.26 mmol), 7.18 g N72-4 (24.26 mmol), 0.44 g tris (dibenzylideneacetone) palladium (0.49 mmol), 0.50 g 2-dicyclohexylphosphine-2', 6'-dimethoxybiphenyl (1.21 mmol), 4.66 g sodium tert-butoxide (48.52 mmol), and 100 mL of toluene were added sequentially, and the mixture was refluxed at 110 ° C for 3 hours. After the reaction was completed, the organic layer was extracted with ethyl acetate (EA), and residual moisture was removed by using anhydrous sodium sulfate, the residue was dried, and purified by column chromatography to obtain 10.97 g of compound N-207 (yield 72%).

[0167] Elemental analysis: C 45 H 28 N2O2; theoretical value: C, 85.97; H, 4.49; N, 4.46; O, 5.09; found value: C, 85.95; H, 4.49; N, 4.48; HRMS (ESI) m / z [M+H] +: theoretical value: 628.22; found value: 628.21.

[0168] The preparation methods of Examples 13-21 are similar to those of Example 1. Specifically, the raw materials used in Examples 13-21 and the products obtained are shown in Table 1 below.

[0169] Table 1

[0170]

[0171]

[0172]

[0173] The characterization data of the products prepared in Examples 13-21 are shown in Table 2:

[0174] Table 2

[0175]

[0176]

[0177] Example 22

[0178] This embodiment provides a method for preparing a compound having an M-17 structure in an organic electroluminescent material, comprising the following steps:

[0179]

[0180] Synthesis of M-17: A 50 ml two-necked round-bottom flask was placed with a stirrer and a reflux tube. After drying, the mixture was filled with nitrogen and compound M17-A (14.1 mmol, CAS 2095370-50-4), M17-B (18.3 mmol), tetrakis(triphenylphosphine)palladium (0.7 mmol), potassium carbonate (28.2 mmol), 42 ml of toluene, 10 ml of ethanol, and 14 ml of distilled water were added. The mixture was stirred at 140 degrees Celsius for 8 hours. After the reaction was complete, the mixture was added dropwise to methanol and the resulting solid was filtered. The resulting solid was purified by column chromatography to give compound M-17 (5.8 g, yield: 75%).

[0181] Elemental analysis: C 39 H 23 N3O theoretical value: C, 85.23; H, 4.22; N, 7.65; O, 2.91; found value: C, 85.21; H, 4.22; N, 7.66; HRMS (ESI) m / z (M+): theoretical value: 549.18; found value: 550.57.

[0182] Example 23

[0183] This embodiment provides a method for preparing a compound having an M-281 structure in an organic electroluminescent material, comprising the following steps:

[0184]

[0185] Synthesis of intermediate M281-A

[0186] To a 250mL three-necked flask equipped with a thermometer and magnetic stirring, add intermediate M281-1 (20g) and 200mL of anhydrous tetrahydrofuran. Under nitrogen protection, cool to -78°C, control the temperature and add n-butyl lithium (1.6M 45.2mL) dropwise. Stir for 1h after the addition is complete, then control the temperature and add triisopropyl borate (19.52g) dropwise at -78°C. After the addition is complete, transfer to room temperature and react for 12h. Add hydrochloric acid solution (36% concentration hydrochloric acid 6.5mL + 24mL water) dropwise, add 50mL of ethyl acetate to the reaction solution, extract with 25mL of water, spin dry the organic phase and add 50mL of n-hexane, reflux and slurry for 1h, filter at room temperature, and dry to obtain intermediate M281-2, 15g.

[0187] To a 250 mL three-necked flask equipped with a thermometer and magnetic stirring, add intermediate M281-2 (15 g), intermediate 3-bromopyridine-4-aldehyde (11.2 g), potassium carbonate (16.6 g) and tetrakistriphenylphosphine palladium (2.0 g), and add toluene (80 mL), ethanol (35 mL) and water (35 mL). Under nitrogen protection, the temperature was raised to 85 ° C and the reaction was reacted for 6 h. 50 mL of ethyl acetate was added to the reaction solution, and 25 mL of water was used for extraction and separation. The organic phase was mixed and passed through a column to obtain intermediate M281-3, 15.2 g.

[0188] To a 250 mL three-necked flask equipped with a thermometer and magnetic stirring, add intermediate M281-3 (15.2 g) and (methoxymethyl)triphenylphosphonium chloride (23.5 g) and 75 mL of anhydrous tetrahydrofuran. Under nitrogen protection, the temperature is controlled to -5°C, and a tetrahydrofuran solution of potassium tert-butoxide (10.2 g, 76 mL) is added dropwise. The reaction is allowed to proceed for 1 h. 50 mL of ethyl acetate is added to the reaction solution, and the solution is extracted with 25 mL of water. The organic phase is mixed and passed through a column to obtain 14 g of intermediate M281-4.

[0189] To a 250 mL three-necked flask equipped with a thermometer and magnetic stirring, add intermediate M281-4 (14 g) and 70 mL of hexafluoroisopropanol. Under nitrogen protection, control the temperature to 0°C, add trifluoromethanesulfonic acid (11 mL) dropwise, and react for 1 hour. Add 30 mL of dichloromethane to the reaction solution, extract with 25 mL of water, and separate the liquids. Mix the organic phase and pass it through a column to obtain 11 g of intermediate M281-5.

[0190] To a 250 mL three-necked flask equipped with a thermometer and magnetic stirring, add intermediate M281-5 (11 g), pinacol diboron (10.9 g), potassium acetate (8.8 g) and Pd(dppf)Cl2 (0.56 g), add 1,4-dioxane (110 mL) and under nitrogen protection, heat to 110 ° C and react for 4 h. Add 100 mL of toluene to the reaction solution, extract with 100 mL of water, and separate the liquid. The organic phase is mixed and passed through a column to obtain intermediate M281-A11 g.

[0191] Synthesis of compound M-281

[0192]

[0193] To a 250 mL three-necked flask equipped with a thermometer and a magnetic stirrer, intermediate M281-A (11 g), intermediate M281-B (10 g), potassium carbonate (9.9 g) and tetrakistriphenylphosphine palladium (1.2 g) were added, and toluene (60 mL), ethanol (20 mL) and water (20 mL) were added. Under nitrogen protection, the temperature was raised to 85 ° C and the reaction was reacted for 6 h. Water and ethanol were added to the reaction solution at room temperature and filtered. After drying, the product M-281, 12 g (yield 86.7%) was obtained.

[0194] Elemental analysis: C 32 H 20 N4 theoretical value: C, 83.46; H, 4.38; N, 12.17; found value: C, 83.44; H, 4.38; N, 12.18; HRMS (ESI) m / z (M+): theoretical value: 460.17; found value: 461.04.

[0195] Examples 24-31 The preparation of Examples 24-31 is similar to that of the above examples. Specifically, the raw materials used in Examples 24-31 and the products obtained are shown in Table 3 below:

[0196] Table 3

[0197]

[0198]

[0199]

[0200] The product characterization data are shown in Table 4 below:

[0201] Table 4

[0202]

[0203]

[0204] Device Examples

[0205] This embodiment provides an organic electroluminescent device, such as Figure 1 As shown, it includes 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 stacked in sequence on a substrate 1, and 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).

[0206] The materials used to manufacture the organic electroluminescent device are as follows:

[0207]

[0208] The preparation of the organic electroluminescent device comprises the following steps:

[0209] 1) Substrate cleaning:

[0210] A glass substrate coated with transparent ITO was ultrasonically treated in an aqueous detergent (the composition and concentration of the aqueous detergent: ethylene glycol solvent ≤ 10wt%, triethanolamine ≤ 1wt%), then rinsed in deionized water, ultrasonically degreased in a mixed solvent of acetone and ethanol (acetone and ethanol volume ratio of 1:1), baked in a clean environment to completely remove moisture, and then cleaned with ultraviolet light and ozone.

[0211] 2) Preparation of organic layer:

[0212] The ITO transparent substrate was transferred to the evaporation equipment and vacuumed to 1×10 -6 to 2×10 -4 Pa, the hole injection layer (HIL) / hole transport layer (HTL) / luminescent layer (EML) / electron transport layer (ETL) / electron injection layer (EIL) / thick cathode (Al) are sequentially deposited on the anode film.

[0213] in:

[0214] 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;

[0215] The materials of the hole transport layer (HTL) are shown in Table 5;

[0216] The light-emitting layer (EML) was vacuum-deposited by co-evaporation. The materials of the light-emitting layer included a host material and a guest material, wherein the guest material was (piq)2Ir(acac). The specific materials of the host material and the ratio of the host material to the guest material are shown in Table 5.

[0217] The materials of the electron transport layer (ETL) are shown in Table 5;

[0218] The material of the electron injection layer (EIL) is LiQ;

[0219] The cathode is aluminum;

[0220] The materials and thicknesses of some layers of the organic electroluminescent device are shown in Table 5

[0221] Table 5

[0222]

[0223]

[0224]

[0225] The examples in the table represent device examples, and the comparative examples in the table are device comparative examples.

[0226] Test Case

[0227] The organic electroluminescent devices obtained from device examples 1 to 16 and comparative examples 1 to 10 in the device examples were tested.

[0228] Instruments: The device's current, voltage, brightness and other characteristics are tested synchronously using a PR 650 spectrum scanning luminance meter and a Keithley K2400 digital source meter system.

[0229] Test conditions: Photoelectric characteristics test conditions: current density is 10mA / cm2.

[0230] Life test: The current density is 50 mA / cm2, and the time (in hours) when the device brightness drops to 95% of the original brightness is recorded.

[0231] The device performance test results are shown in Table 6:

[0232] Table 6

[0233]

[0234]

[0235] By comparing the data corresponding to the examples and comparative examples in Table 6, it can be seen that the organic material composition developed by the present invention has significantly better performance than the combination of compounds A, B, and C disclosed in the prior art, and can have a lower turn-on voltage after being prepared into a device.

[0236] Obviously, the above embodiments are merely examples for clarity of explanation and are not intended to limit the implementation methods. Those skilled in the art will readily appreciate that other variations or modifications based on the above descriptions are possible. It is not necessary and impossible to enumerate all implementation methods here. Obvious variations or modifications arising therefrom remain within the scope of protection of the present invention.

Claims

1. An organic material composition, characterized in that The organic material composition comprises a first compound and a second compound, wherein the first compound has a structure represented by formula (1): Wherein, ring A is a benzene ring; Ar is selected from a substituted or unsubstituted C6-C60 aryl group, a substituted or unsubstituted C6-C60 arylamine group, a substituted or unsubstituted C3-C60 heteroarylamine group, or a substituted or unsubstituted C3-C30 heteroaryl group; L' is selected from a substituted or unsubstituted C6-C30 arylene group, a substituted or unsubstituted C3-C30 heteroarylene group; The second compound has a structure shown in formula (2): Among them, X 1 -X 12 Each is independently selected from N or CR, and R is selected from hydrogen or deuterium; L is selected from a connecting bond, a substituted or unsubstituted C6-C30 arylene group, and a substituted or unsubstituted C3-C30 heteroarylene group; R1 and R2 are each independently selected from a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C3-C30 heteroaryl group, a substituted or unsubstituted C6-C60 arylamine group, or a substituted or unsubstituted C3-C60 heteroarylamine group; The substituents in the substituted C6-C60 aryl group, substituted C6-C60 arylamine group, substituted C3-C60 heteroarylamine group, substituted C3-C30 heteroaryl group, substituted C6-C30 arylene group, substituted C3-C30 heteroarylene group, substituted C6-C30 aryl group, and substituted C3-C30 heteroaryl group are selected from one or a combination of two of deuterium, halogen, cyano, C1-C6 alkyl group, C3-C30 cycloalkyl group, C6-C30 aryl group, and C3-C30 heteroaryl group.

2. The organic material composition according to claim 1, characterized in that In the formula (1), Ar, R1, and R2 are selected from substituted or unsubstituted C6-C25 aryl groups, substituted or unsubstituted C6-C25 arylamine groups, substituted or unsubstituted C3-C25 heteroarylamine groups, and substituted or unsubstituted C3-C20 heteroaryl groups; wherein the substituents in the substituted C6-C25 aryl group, the substituted C6-C25 arylamine group, the substituted C3-C25 heteroarylamine group, and the substituted C3-C20 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 arylamine group, and C3-C60 heteroarylamine group; Preferably, Ar is selected from substituted or unsubstituted B groups, and B groups are selected from the following groups: phenyl, naphthyl, biphenyl, phenanthrenyl, fluoranthene, phenyl, terphenyl, triphenylene, phenalenyl, phenylnaphthyl, naphthylphenyl, dimethylfluorenyl, phenylmethylfluorenyl, diphenylfluorenyl, pyridyl, pyridylphenyl, phenylpyridyl, spirobifluorenyl, benzodimethylfluorenyl, benzodiphenylfluorenyl, benzospirobifluorenyl, dibenzofuranyl, benzonaphthofuranyl, benzonaphthothienyl, spiro[fluorene-9,9'-xanthenyl]yl, phenylmethylfluorenyl, dinaphthofuranyl, dinaphthothienyl, dibenzothienyl, N,N-diphenylanilinoyl; wherein the substituent of the substituted B group is 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 arylamine, and C3-C60 heteroarylamine; Preferably, in the formula (2), R1 and R2 are each independently selected from a substituted or unsubstituted A group, and the A group is selected from the following groups: phenyl, naphthyl, biphenyl, terphenyl, phenanthrenyl, triphenylene, fluorenyl, dimethylfluorenyl, spirobifluorenyl, fluoranthenyl, diphenylfluorenyl, benzodimethylfluorenyl, benzodiphenylfluorenyl, benzospirobifluorenyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, phenylcarbazolyl, bipyridyl, pyrimidinyl, triazinyl; Wherein, the substituent of the substituted A group is 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 aromatic amine, and C3-C60 heteroaromatic amine.

3. The organic material composition according to claim 1 or 2, characterized in that In the formula (1), Ar is selected from phenyl, naphthyl, biphenyl, phenyl, phenanthrenyl, terphenyl, phenylnaphthyl, naphthylphenyl, dimethylfluorenyl, diphenylfluorenyl, spirobifluorenyl, phenanthrenyl, dibenzofuranyl, benzonaphthofuranyl, N,N-diphenylanilino; Preferably, in the formula (2), R1 and R2 are each independently selected from phenyl, naphthyl, biphenyl, terphenyl, phenanthrenyl, triphenylene, fluorenyl, dimethylfluorenyl, spirobifluorenyl, fluoranthenyl, diphenylfluorenyl, benzodimethylfluorenyl, benzodiphenylfluorenyl, benzospirobifluorenyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, phenylcarbazolyl, bipyridyl, pyrimidinyl, triazine.

4. The organic material composition according to any one of claims 1 to 3, characterized in that: L' is selected from substituted or unsubstituted C6-C15 arylene; wherein the substituents in the substituted C6-C15 arylene group are independently selected from one or a combination of at least two of deuterium, halogen, and C1-C62 alkyl; Preferably, L' is selected from phenylene, biphenylene, naphthylene; Preferably, L' is selected from phenylene and naphthylene; Preferably, in the formula (2), L is a single bond; Preferably, X1-X 12 Each independently selected from CR; or, X1-X 12 Wherein X2 is selected from N, and the others are independently selected from CR; or, X1-X 12 wherein X5 is selected from N, and the others are independently selected from CR; or, X1-X 12 wherein X8 is selected from N, and the others are independently selected from CR; or, X1-X 12 wherein X9 is selected from N, and the others are independently selected from CR.

5. The organic material composition according to any one of claims 1 to 4, characterized in that: The first compound has the structure shown in any one of N-1 to N-208 below:

6. The organic material composition according to any one of claims 1 to 5, characterized in that: The second compound has a structure shown in any one of the following M-1 to M-348:

7. The organic material composition according to any one of claims 1 to 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; Further 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: The organic material composition comprises the organic material composition according to any one of claims 1 to 7.

9. Use of the organic material composition according to any one of claims 1 to 7 or the organic electroluminescent host material composition 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, wherein the organic layer comprises the organic material composition according to any one of claims 1 to 7 or the organic electroluminescent host material composition according to claim 8; Preferably, the organic layer includes a light-emitting layer, and the light-emitting layer includes the organic material composition according to any one of claims 1 to 7 or the organic electroluminescent host material composition according to claim 8.

11. An organic electroluminescent device, characterized in that: The organic electroluminescent device according to claim 10 is included.

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