An organic material composition and its application

Abstract

The present invention relates to the field of display technology, and in particular to an organic material composition and its application. The present invention provides an organic material composition, the organic material composition comprises a first compound and a second compound, the first compound and the second compound having the following structures: Formula (1), Formula (2), the first compound having the structure shown in Formula (1) and the second compound having the structure shown in Formula (2) cooperate with each other to facilitate the matching of HOMO and LUMO energy levels with adjacent energy levels, so that the organic material composition obtains higher stability and more balanced carrier mobility, thereby making the organic electroluminescent device containing the material have a better lifespan, and also have a 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 an organic EL device may include a hole injection layer, a hole transport layer, a hole auxiliary layer, a luminescent auxiliary layer, an electron blocking layer, a luminescent layer (containing a host material and a dopant material), an electron buffer layer, a hole blocking layer, an electron transport layer, an electron injection layer, etc. The materials used in the organic layer may be divided into hole injection materials, hole transport materials, hole auxiliary materials, luminescent auxiliary materials, electron blocking materials, luminescent materials, electron buffer materials, hole blocking materials, electron transport materials, electron injection materials, etc. 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 organic electroluminescent diodes to have high driving voltage and short life, 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, unbalanced carrier mobility and the like of functional materials composed of existing organic light-emitting compounds, which result in 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 in the present invention, the term "C1-C30 alkyl" refers to a monovalent substituent derived from a straight or branched chain saturated hydrocarbon having 1 to 30 carbon atoms, examples of which include but are not limited to methyl, ethyl, 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, 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, phenanthryl, anthracenyl, fluorenyl, spirobifluorenyl, etc., and arylene groups include but are not limited to phenylene, biphenylene, terphenylene, naphthyl, phenanthryl, anthracenyl, fluorenyl, spirobifluorenyl, etc.

[0010] In the present invention, heteroaryl and heteroarylide include monocyclic, polycyclic or condensed ring heteroaryl, and the rings may be interrupted by short non-aromatic units, and the heteroatoms include nitrogen, oxygen and sulfur. Heteroaryl includes, but is not limited to, furanyl, phenylthio, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetrazinyl, triazolyl, tetrazolyl, furazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, benzofuranyl, benzothiophenyl, isobenzofuranyl, dibenzofuranyl, dibenzothiophenyl, benzimidazolyl, benzo thiazolyl, benzisothiazolyl, benzisoxazolyl, benzoxazolyl, isoindolyl, indolyl, indazolyl, benzothiadiazolyl, quinolyl, isoquinolyl, cinnolinyl, quinazolinyl, quinoxalinyl, carbazolyl, phenoxazinyl, phenothiazinyl, phenanthridinyl, benzodioxolyl, dihydroacridinyl, and derivatives thereof; heteroarylene includes but is not limited to furanyl, phenylene thio, pyrroleyl yl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetrazinyl, triazolyl, tetrazolyl, furazolyl, pyridyl, pyrazinyl, pyrimidyl, pyridazinyl, benzofuranyl, benzothiophenylene, isobenzofuranyl, dibenzofuranyl, dibenzothiophenylene, benzimidazolyl, oxazolyl, benzothiazolyl, benzoisothiazolyl, benzoisoxazolyl, benzoxazolyl, isoindolyl, indolyl, indazolyl, benzothiadiazolyl, quinolyl, isoquinolyl, cinnolinyl, quinazolinyl, quinoxalinyl, carbazolyl, phenoxazinyl, phenothiazinyl, phenanthridinyl, benzodioxolyl, acridinyl, and derivatives thereof.

[0011] As used in the present invention, the term "substituted" refers to a hydrogen atom in a compound being replaced by another substituent. The position is not limited to a specific position, as long as the hydrogen at the position can be replaced by a substituent. 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 range of the number of carbon atoms is defined in the definition of the group, and the number of carbon atoms is any integer within the defined range. For example, C6-C30 aromatic group, the number of carbon atoms representing the aromatic group can be any integer within the range of 6-60, such as 6, 8, 10, 13, 15, 17, 20, 22, 25 or 30, etc.

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

[0015] The present invention provides an organic material composition, which comprises 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 substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C6-C60 arylamine, substituted or unsubstituted C3-C60 heteroarylamine, substituted or unsubstituted C3-C30 heteroaryl;

[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 14 Each is independently selected from N or CR, and R is selected from hydrogen, deuterium, and C6-C30 aryl;

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

[0024] Ar1 and Ar2 are each independently selected from substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl;

[0025] The substituents in the substituted C6-C30 arylene group, substituted C3-C30 heteroarylene group, substituted C6-C60 aryl group, substituted C6-C60 aromatic amine group, substituted C3-C60 heteroaromatic amine group, substituted C3-C60 heteroaryl group, substituted C3-C30 heteroaryl group and substituted C3-C30 heteroaromatic group are selected from one or a combination of two of deuterium, halogen, cyano, C1-C12 alkyl group, C3-C30 cycloalkyl group, C6-C30 aryl group, C3-C30 heteroaryl group, C6-C60 aromatic amine group and C3-C60 heteroaromatic amine group.

[0026] Understandably, Ring A in formula (1) can be fused with ring C at 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, Ar1, Ar2 are selected from substituted or unsubstituted C6-C25 aryl groups, substituted or unsubstituted C6-C25 arylamine groups, substituted or unsubstituted C3-C25 heteroarylamine groups, substituted or unsubstituted C3-C20 heteroaryl groups;

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

[0029] Preferably, Ar is selected from a substituted or unsubstituted B group, and the B group is selected from the following groups: phenyl, naphthyl, biphenyl, phenanthryl, fluoranthene, yl, 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 aromatic amine, and C3-C60 heteroaromatic amine.

[0031] Preferably, Ar is selected from phenyl, naphthyl, biphenyl, phenyl, phenanthrenyl, terphenyl, phenylnaphthyl, naphthylphenyl, dimethylfluorenyl, diphenylfluorenyl, spirobifluorenyl, phenanthrenyl, dibenzofuranyl, benzonaphthofuranyl, N,N-diphenylanilino.

[0032] Preferably, L' is selected from substituted or unsubstituted C6-C15 arylene groups; wherein the substituents in the substituted C6-C15 arylene groups are each independently selected from one or a combination of at least two of deuterium, halogen, and C1-C62 alkyl groups;

[0033] Preferably, L' is selected from phenylene, biphenylene, naphthylene;

[0034] Preferably, L' is selected from phenylene and naphthylene.

[0035] Preferably, the first compound has a structure shown in any one of the following N-1 to N-208:

[0036]

[0037]

[0038]

[0039]

[0040]

[0041]

[0042]

[0043]

[0044]

[0045] Preferably, in the formula (2), X 1 -X 14 All are selected from CR, R is defined as above;

[0046] Preferably, X 1 -X 6 Any one of them is selected from N, the others are CR, and R is defined as above;

[0047] Preferably, X 1 -X 6 Any one of them is selected from N, and the rest are CR; X 7 -X 14Any one of them is selected from N, the others are CR, and R is defined as above;

[0048] Preferably, R is selected from hydrogen, deuterium, phenyl, naphthyl;

[0049] Ar1 and Ar2 are each independently selected from substituted or unsubstituted C6-C15 aryl, substituted or unsubstituted C3-C20 heteroaryl;

[0050] The substituents in the substituted C6-C15 aryl group and the substituted C3-C20 heteroaryl group are selected from one or a combination of two of deuterium, halogen, cyano, C1-C6 alkyl, C3-C30 cycloalkyl, C6-C30 aryl, C3-C30 heteroaryl, C6-C60 arylamine, and C3-C60 heteroarylamine;

[0051] Preferably, Ar1 and Ar2 are each independently selected from a substituted or unsubstituted A group;

[0052] The A group includes: phenyl, naphthyl, biphenyl, terphenyl, phenanthryl, fluoranthene, triphenylene, fluorenyl, dimethylfluorenyl, diphenylfluorenyl, spirobifluorenyl, benzodimethylfluorenyl, benzodiphenylfluorenyl, benzospirobifluorenyl, benzofuranyl, dibenzofuranyl, naphthobenzofuranyl, dinaphthofuranyl, benzothienyl, dibenzothienyl, naphthobenzothienyl, carbazolyl, phenylcarbazolyl, benzophenylcarbazolyl, dibenzophenylcarbazolyl, biphenylcarbazolyl, phenanthrenylbenzofuranyl, dibenzofuranofuranyl, phenylcarbazolylbenzofuranyl;

[0053] Wherein, the substituent of the substituted A group is selected from one or a combination of two of deuterium, halogen, cyano, C1-C6 alkyl, C3-C30 cycloalkyl, C6-C30 aryl, C3-C30 heteroaryl, C6-C60 arylamine, C3-C60 heteroarylamine;

[0054] Preferably, Ar1 and Ar2 are each independently selected from phenyl, naphthyl, biphenyl, terphenyl, phenanthryl, fluoranthene, triphenylene, fluorenyl, dimethylfluorenyl, diphenylfluorenyl, spirobifluorenyl, benzodimethylfluorenyl, benzodiphenylfluorenyl, benzospirobifluorenyl, dibenzofuranyl, naphthiobenzofuranyl, dibenzothiophenyl, naphthiobenzothiophenyl, carbazolyl, phenylcarbazolyl, benzocarbazolyl, dibenzocarbazolyl;

[0055] Preferably, L is independently selected from a linker, a substituted or unsubstituted C6-C18 arylene group;

[0056] Preferably, L is selected from a linker and a phenylene group.

[0057] Preferably, the second compound has a structure as shown in any one of the following formulas 2-1 to 2-28:

[0058]

[0059]

[0060]

[0061] Preferably, X 1 -X 14 , Ar1, Ar2 are as defined above;

[0062] Preferably, the second compound has a structure shown in Formula 2-4 or Formula 2-5;

[0063] Preferably, the second compound has any structure of Formula 2-6, Formula 2-22, Formula 2-25, Formula 2-26, Formula 2-27, Formula 2-28, Formula 2-8 to Formula 2-20.

[0064] Preferably, the second compound has a structure shown in any one of M-1 to M-723:

[0065]

[0066]

[0067]

[0068]

[0069]

[0070]

[0071]

[0072]

[0073]

[0074]

[0075]

[0076]

[0077]

[0078]

[0079]

[0080]

[0081]

[0082]

[0083] Preferably, in the material composition, the mass ratio of the first compound to the second compound is 1:9-9:1;

[0084] Preferably, in the material composition, the mass ratio of the first compound to the second compound is 2:8-8:2;

[0085] More preferably, in the material composition, the mass ratio of the first compound to the second compound is 3:7-7:3;

[0086] Further preferably, in the material composition, the mass ratio of the first compound to the second compound is 4:6-6:4.

[0087] The present invention provides an organic electroluminescent host material composition, comprising the organic material composition described above.

[0088] 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;

[0089] Preferably, the optical device comprises an organic electroluminescent device.

[0090] 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 described above or the organic electroluminescent host material composition described above;

[0091] 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.

[0092] 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;

[0093] 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 as described above or the organic electroluminescent host material composition as described above.

[0094] Preferably, the guest material comprises a phosphorescent dopant, and the phosphorescent dopant comprises a complex containing a transition metal.

[0095] The present invention provides an organic electroluminescent device, comprising the organic electroluminescent device described above.

[0096] The term "organic electroluminescent material" disclosed in the present invention means a material that can be used in an organic electroluminescent device and can contain at least one compound. If necessary, the organic electroluminescent material can be contained in any layer constituting the organic electroluminescent device. For example, the organic electroluminescent material can be a hole injection material, a hole transport material, a hole auxiliary material, a luminescence auxiliary material, an electron blocking material, a luminescent material (containing 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.

[0097] An organic electroluminescent material disclosed in the present invention may include an organic electroluminescent material, or may include a plurality of organic electroluminescent materials, wherein a 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 an organic electroluminescent device. It may mean both a material contained before the organic electroluminescent device (e.g., before vapor deposition) and a material contained after the organic electroluminescent device (e.g., after vapor deposition). 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.

[0098] 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 contained in an organic electroluminescent device before (e.g., before vapor deposition) and a material contained in an organic electroluminescent device after (e.g., after vapor deposition). The composition disclosed in the present invention may be contained in any light-emitting layer constituting an organic electroluminescent device. Two or more compounds of the multiple host materials contained in the composition disclosed in the present invention may be contained in one light-emitting layer, or may be contained in different light-emitting layers, respectively. For example: when two or more host materials are contained in one layer, the layer may be formed by mixed evaporation, or may be formed simultaneously by separate co-evaporation.

[0099] In the present invention, the first compound can be prepared by the following synthetic route, comprising the following steps:

[0100] 1. Synthesis of intermediate Nn-A: The reaction raw materials Nn-1 and Nn-2 are subjected to Suzuki cross-coupling reaction, and the reaction formula is as follows:

[0101]

[0102] 2. Synthesis of compound Nn: Intermediates Nn-A and Nn-B undergo Buchwald-Hartwig cross-coupling reaction, and the reaction formula is as follows:

[0103]

[0104] Beneficial effects of the present invention:

[0105] The organic material composition of the present invention comprises a first compound and a second compound, wherein the first compound has a structure as shown in formula (1), and the second compound has a structure as shown in formula (2); the first compound having a structure as shown in formula (1) and the second compound having a structure as shown in formula (2) cooperate with each other, which is beneficial for matching HOMO and LUMO energy levels with adjacent energy levels, so that the organic material composition obtains higher stability and more balanced carrier mobility, thereby making the organic electroluminescent device containing the material have a better lifespan, and also has a lower driving voltage and higher efficiency. BRIEF DESCRIPTION OF THE DRAWINGS

[0106] In order to more clearly illustrate the specific implementation methods of the present invention or the technical solutions in the prior art, the drawings required for use in the specific implementation methods or the description of the prior art will be briefly introduced below. Obviously, the drawings described below are some implementation methods of the present invention. For ordinary technicians in this field, other drawings can be obtained based on these drawings without paying creative work.

[0107] Figure 1 A structural diagram of an organic electroluminescent device in an embodiment of the device of the present invention;

[0108] 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

[0109] The following examples are provided for a better understanding of the present invention, but are not intended to limit the best mode of implementation, nor to limit the content and protection scope 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 protection scope of the present invention.

[0110] If no specific experimental steps or conditions are specified in the examples, the conventional experimental steps or conditions described in the literature in the field can be used. If no manufacturer is specified for the reagents or instruments used, they are all conventional reagent products that can be obtained commercially.

[0111] Example 1

[0112] 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:

[0113]

[0114] Synthesis of intermediate N1-A

[0115] After nitrogen replacement to a three-mouth reaction bottle equipped with mechanical stirring, a thermometer, and a condenser, 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, 30mL water were added in sequence. And 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 10.06g of compound N1-A (yield 90%).

[0116] Synthesis of intermediate N1-B

[0117] After nitrogen replacement of a three-mouth reaction bottle equipped with mechanical stirring, a thermometer, and a condenser, intermediate 10gN1-A (32.78mmol), 3.1gN1-3 (32.78mmol), 0.6g tris (dibenzylideneacetone) palladium (0.66mmol), 0.67g 2-dicyclohexylphosphine-2', 6'-dimethoxybiphenyl (1.64mmol), 6.3g sodium tert-butoxide (65.56mmol), 100mL of toluene were added in sequence, and the mixture was refluxed and stirred 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 8.31g of compound N1-B (yield 82%).

[0118] Synthesis of Compound N-1

[0119] After nitrogen replacement in a three-mouth reaction bottle equipped with mechanical stirring, a thermometer, and a condenser, 8.30 g of intermediate N1-B (26.85 mmol), 7.95 g of N1-4 (26.85 mmol), 0.49 g of tris (dibenzylideneacetone) dipalladium (0.54 mmol), 0.55 g of 2-dicyclohexylphosphine-2', 6'-dimethoxybiphenyl (1.34 mmol), 5.16 g of sodium tert-butoxide (53.70 mmol), and 100 mL of toluene were added in sequence, and the mixture was stirred under reflux 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%).

[0120] 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.

[0121] Example 2

[0122] 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:

[0123]

[0124] After nitrogen replacement of a three-mouth reaction bottle 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 in sequence, and the mixture was refluxed and stirred 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 14.41g of compound N6-B (yield 73%).

[0125] After nitrogen replacement in a three-mouth reaction bottle equipped with mechanical stirring, a thermometer, and a condenser, an intermediate 10gN6-B (16.60mmol), 4.91gN1-4 (16.60mmol), 0.30g tris (dibenzylideneacetone) palladium (0.33mmol), 0.34g2-dicyclohexylphosphine-2', 6'-dimethoxybiphenyl (0.83mmol), 3.19g sodium tert-butoxide (33.21mmol), 100mL of toluene were added in sequence, and the mixture was refluxed and stirred 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 9.24g of oxazole organic compound N-6 containing benzonaphthofuran (yield 68%).

[0126] 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.

[0127] Example 3

[0128] 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:

[0129]

[0130] After nitrogen replacement of a three-mouth reaction bottle equipped with mechanical stirring, a thermometer, and a condenser, intermediate 10gN1-A (32.78mmol), 8.53gN18-3 (32.78mmol), 0.60g tris (dibenzylideneacetone) palladium (0.66mmol), 0.67g 2-dicyclohexylphosphine-2', 6'-dimethoxybiphenyl (1.64mmol), 6.3g sodium tert-butoxide (65.56mmol), 100mL of toluene were added in sequence, and the mixture was refluxed and stirred 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%).

[0131] After nitrogen replacement in a three-mouth reaction bottle equipped with mechanical stirring, a thermometer, and a condenser, 10 g N18-B (18.90 mmol), 5.59 g N18-4 (18.90 mmol), 0.35 g tris (dibenzylideneacetone) dipalladium (0.38 mmol), 0.39 g 2-dicyclohexylphosphine-2', 6'-dimethoxybiphenyl (0.94 mmol), 3.63 g sodium tert-butoxide (37.79 mmol), 100 mL of toluene were added in sequence, and the mixture was stirred under reflux 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 10.70 g of organic electroluminescent compound N-18 (yield 76%).

[0132] 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.

[0133] Example 4

[0134] 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:

[0135]

[0136] After nitrogen replacement of a three-mouth reaction bottle equipped with mechanical stirring, a thermometer, and a condenser, intermediate 10gN1-A (32.78mmol), 5.54gN30-3 (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 in sequence, and the mixture was refluxed and stirred 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 11.49g of compound N30-B (yield 80%).

[0137] After nitrogen replacement in a three-mouth reaction bottle equipped with mechanical stirring, a thermometer, and a condenser, an intermediate 10gN30-B (22.82mmol), 6.75gN30-4 (22.82mmol), 0.42g tris (dibenzylideneacetone) dipalladium (0.46mmol), 0.47g 2-dicyclohexylphosphine-2', 6'-dimethoxybiphenyl (1.14mmol), 4.39g sodium tert-butoxide (45.64mmol), 100mL of toluene were added in sequence, 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 10.75g of oxazole organic compound N-30 containing benzonaphthofuran (yield 72%).

[0138] 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.

[0139] Example 5

[0140] 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:

[0141]

[0142] After nitrogen replacement of a three-mouth reaction bottle equipped with mechanical stirring, 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 in sequence, and the mixture was refluxed and stirred 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%).

[0143] After nitrogen replacement in a three-mouth reaction bottle equipped with mechanical stirring, a thermometer, and a condenser, 7.50 g of intermediate N45-B (15.36 mmol), 3.87 g of N45-4 (15.36 mmol), 0.28 g of tris (dibenzylideneacetone) palladium (0.31 mmol), 0.31 g of 2-dicyclohexylphosphine-2', 6'-dimethoxybiphenyl (0.77 mmol), 2.95 g of sodium tert-butoxide (30.73 mmol), 80 mL of toluene were added in sequence, and the mixture was stirred under reflux 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%).

[0144] 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.

[0145] Example 6

[0146] 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:

[0147]

[0148] Synthesis of intermediate N72-A

[0149] After nitrogen replacement to a three-mouth reaction bottle equipped with mechanical stirring, a thermometer, and a condenser, 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, 30mL water were added sequentially. And 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 9.50g of compound N72-A (yield 85%).

[0150] Synthesis of intermediate N72-B

[0151] After nitrogen replacement in a three-mouth reaction bottle equipped with mechanical stirring, 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 in sequence, and the mixture was stirred at 110 ° C for 3 hours under reflux. 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%).

[0152] After nitrogen replacement in a three-mouth reaction bottle equipped with mechanical stirring, a thermometer, and a condenser, an intermediate 10g N72-B (20.48mmol), 6.06g N72-4 (20.48mmol), 0.37g tris (dibenzylideneacetone) palladium (0.41mmol), 0.42g 2-dicyclohexylphosphine-2', 6'-dimethoxybiphenyl (1.02mmol), 3.94g sodium tert-butoxide (40.97mmol), 100mL of toluene were added in sequence, 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 10.82g of oxazole organic compound N-72 containing benzonaphthofuran (yield 75%).

[0153] 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.

[0154] Example 7

[0155] 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:

[0156]

[0157] After nitrogen replacement to a three-mouth reaction bottle equipped with mechanical stirring, a thermometer, and a condenser, raw materials 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, 30mL water were added in sequence. And 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%).

[0158] After nitrogen replacement in a three-mouth reaction bottle equipped with mechanical stirring, 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 in sequence, 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 10.69 g of compound N95-B (yield 72%).

[0159] After nitrogen replacement in a three-mouth reaction bottle equipped with mechanical stirring, a thermometer, and a condenser, an intermediate 10gN95-B (20.48mmol), 6.06gN95-4 (20.48mmol), 0.37g tris (dibenzylideneacetone) dipalladium (0.41mmol), 0.42g 2-dicyclohexylphosphine-2', 6'-dimethoxybiphenyl (1.02mmol), 3.94g sodium tert-butoxide (40.97mmol), 100mL of toluene were added in sequence, 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 10.10g of oxazole organic compound N-95 containing benzonaphthofuran (yield 70%).

[0160] 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.

[0161] Example 8

[0162] 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:

[0163]

[0164] After nitrogen substitution in a three-mouth reaction bottle equipped with mechanical stirring, 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) palladium (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 in sequence, and the mixture was stirred under reflux 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%).

[0165] 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.

[0166] Example 9

[0167] 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:

[0168]

[0169] After nitrogen replacement of a three-mouth reaction bottle equipped with mechanical stirring, a thermometer, and a condenser, an intermediate 10gN73-A (32.78mmol), 5.54g N30-3 (32.78mmol), 0.60g tris (dibenzylideneacetone) palladium (0.66mmol), 0.67g 2-dicyclohexylphosphine-2', 6'-dimethoxybiphenyl (1.64mmol), 6.3g sodium tert-butoxide (65.56mmol), 100mL of toluene were added in sequence, and the mixture was refluxed and stirred 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%).

[0170] After nitrogen substitution in a three-mouth reaction bottle equipped with mechanical stirring, a thermometer, and a condenser, an intermediate 10gN148-B (22.82mmol), 6.57g N18-4 (22.82mmol), 0.42g tris (dibenzylideneacetone) dipalladium (0.46mmol), 0.47g 2-dicyclohexylphosphine-2', 6'-dimethoxybiphenyl (1.14mmol), 4.39g sodium tert-butoxide (45.64mmol), 100mL of toluene were added in sequence, and the mixture was refluxed and stirred 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 11.20g of oxazole organic compound N-148 containing benzonaphthofuran (yield 75%).

[0171] 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.

[0172] Example 10

[0173] This embodiment provides an organic electroluminescent compound N-173. The synthesis of the organic electroluminescent compound N-173 specifically includes the following steps:

[0174]

[0175] After nitrogen replacement of a three-mouth reaction bottle equipped with mechanical stirring, a thermometer, and a condenser, an intermediate 10gN73-A (32.78mmol), 4.69g N173-3 (32.78mmol), 0.60g tris (dibenzylideneacetone) palladium (0.66mmol), 0.67g 2-dicyclohexylphosphine-2', 6'-dimethoxybiphenyl (1.64mmol), 6.30g sodium tert-butoxide (65.56mmol), 100mL of toluene were added in sequence, and the mixture was refluxed and stirred 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%).

[0176] After nitrogen substitution in a three-mouth reaction bottle 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) palladium (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 in sequence, and the mixture was stirred under reflux 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%).

[0177] 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.

[0178] Embodiment 11

[0179] This embodiment provides an organic electroluminescent compound N-182. The synthesis of the organic electroluminescent compound N-182 specifically includes the following steps:

[0180]

[0181] After nitrogen replacement to a three-mouth reaction bottle 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, 30mL water were added in sequence. And 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 8.94g of compound N182-A (yield 80%).

[0182] After nitrogen replacement of a three-mouth reaction bottle equipped with mechanical stirring, a thermometer, and a condenser, an intermediate 8.94g N182-A (29.31mmol), 4.96g N30-3 (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 in sequence, and the mixture was refluxed and stirred 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%).

[0183] After nitrogen replacement in a three-mouth reaction bottle equipped with mechanical stirring, a thermometer, and a condenser, an 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), 100 mL of toluene were added in sequence, and the mixture was stirred under reflux 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%).

[0184] Elemental analysis: C 47 H 30N2O2; 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.

[0185] Example 12

[0186]

[0187] After nitrogen replacement of a three-mouth reaction bottle equipped with mechanical stirring, a thermometer, and a condenser, an 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 in sequence, and the mixture was refluxed and stirred 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%).

[0188] After nitrogen replacement in a three-mouth reaction bottle equipped with mechanical stirring, a thermometer, and a condenser, 10 g of intermediate N207-B (24.26 mmol), 7.18 g of N72-4 (24.26 mmol), 0.44 g of tris (dibenzylideneacetone) palladium (0.49 mmol), 0.50 g of 2-dicyclohexylphosphine-2', 6'-dimethoxybiphenyl (1.21 mmol), 4.66 g of sodium tert-butoxide (48.52 mmol), and 100 mL of toluene were added in sequence, and the mixture was refluxed and stirred 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%).

[0189] 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.

[0190] 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.

[0191] Table 1

[0192]

[0193]

[0194] The characterization data of the products prepared in Examples 13-21 are shown in Table 2:

[0195] Table 2

[0196]

[0197]

[0198] Embodiment 22

[0199] This embodiment provides a compound M-17 in an organic material composition, and its preparation method comprises the following steps:

[0200]

[0201] Take 50 ml of double-necked round-bottom flask and put in a stirrer and a reflux tube, fill with nitrogen after drying, add compound M17-A (19.8mmol, CAS: 1884145-03-2), M17-B (20.75mmol, CAS: 1883265-32-4), tetrakis triphenylphosphine palladium (0.396mmol), potassium carbonate (39.6mmol), 35 ml of toluene, 15 ml of ethanol and 15 ml of distilled water, and stir the mixture at 90 degrees Celsius for 8 hours. After the reaction is complete, the mixture is added dropwise to methanol, and the solid is filtered. The solid is purified by column chromatography to obtain compound M-17 (8.5g, yield: 75%).

[0202] Elemental analysis: C 41 H 25 N3O; theoretical value: C, 85.54; H, 4.38; N, 7.30; O, 2.78; found value: C, 85.52; H, 4.38; N, 7.32; HRMS (ESI) m / z (M+): theoretical value: 575.20; found value: 576.34.

[0203] Embodiment 23

[0204] This embodiment provides a compound M-296 in an organic material composition, and its preparation method comprises the following steps:

[0205] The synthesis route of intermediate M296-A is as follows:

[0206]

[0207] To a 250mL three-necked flask equipped with a thermometer and magnetic stirring, add intermediate M296-1 (2-bromoquinoline, CAS: 2005-43-8, 20g) and 200mL 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, then control the temperature to -78°C and add triisopropyl borate (19.52g), transfer to room temperature and react for 12h, add hydrochloric acid solution (6.5mL of 36% hydrochloric acid + 24mL of water), 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 M296-2, 15g.

[0208] To a 250 mL three-necked flask equipped with a thermometer and magnetic stirring, add intermediate M296-2 (15 g), intermediate 7-bromo-1-chloronaphthalene (21.9 g), potassium carbonate (16.6 g) and tetrakistriphenylphosphine palladium (2.0 g), add toluene (80 mL), ethanol (35 mL) and water (35 mL) and heat to 85 ° C under nitrogen protection for 6 h. Add 50 mL of ethyl acetate and 25 mL of water to the reaction solution for extraction and separation. The organic phase is mixed and passed through a column to obtain intermediate M296-3, 15 g.

[0209] To a 250mL three-necked flask equipped with a thermometer and magnetic stirring, add intermediate M296-3 (15g), diboronic acid pinacol ester (15.8g), potassium acetate (10g) and Pd(dppf)Cl2 (0.64g), add 1,4-dioxane (150mL) and under nitrogen protection, heat to 110℃ and react for 4h. Add 100mL of toluene and 100mL of water to the reaction solution for extraction and separation. Mix the organic phase and pass it through a column to obtain intermediate M296-A, 16g.

[0210] The synthesis route of compound M-296 is as follows:

[0211]

[0212] To a 250 mL three-necked flask equipped with a thermometer and magnetic stirring, add intermediate M296-A (16 g), intermediate M296-B (2-chloro-4,6-diphenyl-1,3,5-triazine, CAS: 3842-55-5, 11.2 g), potassium carbonate (11.6 g) and tetrakistriphenylphosphine palladium (1.3 g), add toluene (110 mL), ethanol (50 mL) and water (50 mL) under nitrogen protection, heat to 85 ° C and react for 6 hours, add water and ethanol at room temperature, filter the reaction solution, and dry to obtain the product M-296, 16 g (yield 78%).

[0213] Elemental analysis: C 34 H 22 N4 theoretical value: C, 83.93; H, 4.56; N, 11.51; found value: C, 83.95; H, 4.56; N, 11.49; HRMS (ESI) m / z (M+): theoretical value: 486.18; found value: 487.12.

[0214] Examples 24-27

[0215] Examples 24-27 provide methods for preparing compounds M-76, M-253, M-394 or M-480. The specific preparation methods are as follows:

[0216] Raw materials Mn-B, raw materials Mn-A, potassium carbonate and tetrakistriphenylphosphine palladium are added toluene, ethanol and water under nitrogen protection conditions, and the temperature is raised to react. After the reaction is completed, the final product is purified; the amount of the substances used and the experimental parameters are the same as those in Example 1.

[0217] The structures and yields of the raw material Mn-B, raw material Mn-A and the product are shown in Table 3. The elemental analysis results of the prepared compound are shown in Table 4; the amounts of the substances used and the experimental parameters are the same as those in Example 22.

[0218] Table 3

[0219]

[0220]

[0221] The product characterization data are shown in Table 4:

[0222] Table 4

[0223]

[0224] Embodiment 28

[0225] This embodiment provides a compound M-620 in an organic material composition, and its preparation method comprises the following steps:

[0226]

[0227] To a 250mL three-necked flask equipped with a thermometer and magnetic stirring, add the raw material SubM3-Bb (42mmol), the raw material deuterated 1-naphthaleneboronic acid (42.5mmol), potassium carbonate (84mmol) and tetrakistriphenylphosphine palladium (2mmol), add toluene (80mL), ethanol (35mL) and water (35mL), and under nitrogen protection, heat to 85℃ and react for 6h. Add 50mL of ethyl acetate and 25mL of water to the reaction solution for extraction and separation. Mix the organic phase and pass it through a column to obtain the intermediate M620-A-1, 10g.

[0228] To a 250mL three-necked flask equipped with a thermometer and magnetic stirring, add intermediate M620-A-1 (34mmol), bipyraclostrobin (40mmol), potassium acetate (68mmol) and Pd(dppf)Cl2 (1.7mmol), add 1,4-dioxane (150mL) and under nitrogen protection, heat to 110℃ and react for 4h. Add 100mL of toluene and 100mL of water to the reaction solution for extraction and separation. Mix the organic phase and pass it through a column to obtain intermediate M620-A-2, 8g.

[0229]

[0230] After nitrogen replacement, M620-Ba (10 mmol), M-1-a (1.05 mmol), 1,4-dioxane 100 mL, water 30 mL, sodium carbonate (20 mmol), Pd (PPh3) 4 (0.05 mmol) were added to a three-mouth reaction bottle equipped with a mechanical stirrer, a thermometer, and a condenser tube, and then heated to 70-80°C and reacted for 3 hours. The temperature was lowered to 25-30°C, 100 mL of water and 100 mL of toluene were added to stir and separate the liquids, the aqueous phase was extracted once with 100 mL of toluene, the liquids were separated, the organic phases were combined, 7 g of anhydrous sodium sulfate was added to the organic phase, stirred and dried, filtered, the organic phase was concentrated (-0.08-0.09 MPa, 55-60°C) until no liquid flowed out, 50 mL of a mixed solvent of dichloromethane and petroleum ether was added with stirring, the temperature was lowered by 0-5°C, and filtered to obtain the intermediate M620-B-1 with a yield of 46%.

[0231] After nitrogen replacement, add intermediate M620-B-1 (10 mmol), intermediate 1-A (10 mmol), potassium carbonate (20 mmol), Pd (PPh3) 4 (0.05 mmol), 100 mL of 1,4-dioxane, 30 mL of water, start stirring, and heat to 70-75 ° C for 3 h. Cool down to 25-30 ° C, add 100 mL of water, 100 mL of dichloromethane, stir and separate, extract the aqueous phase with 100 mL of dichloromethane once, separate, combine the organic phases, add 7 g of anhydrous sodium sulfate to the organic phase, stir and dry, filter, concentrate the organic phase (-0.08-0.09 MPa, 55-60 ° C) until no liquid flows out, stir and add 20 mL of petroleum ether, cool down 0-5 ° C, filter to obtain a crude product, and recrystallize the crude product from toluene to obtain the product M-620 with a yield of 54%.

[0232] Elemental analysis: C 41 H 13 D 12 N3O theoretical value: C, 83.79; H, 6.34; N, 7.15; O, 2.72; found value: C, 83.77; H, 6.33; N, 7.18; HRMS (ESI) m / z [M+H]+: theoretical value: 587.28; found value: 588.27.

[0233] Embodiment 29

[0234] This embodiment provides a compound M-624 in an organic material composition, and its preparation method comprises the following steps:

[0235]

[0236] 1) After nitrogen replacement, add SubM3-A (10mmol), M-1-a (1.05mmol), 1,4-dioxane 100mL, water 30mL, sodium carbonate (20mmol), Pd(PPh3)4 (0.05mmol) in sequence to a three-necked reaction flask equipped with a mechanical stirrer, a thermometer, and a condenser, heat to 70-80°C, and react for 3h. Cool to 25-30°C, add 100mL of water, 100mL of toluene, stir and separate, extract the aqueous phase with 100mL of toluene once, separate, combine the organic phases, add 7g of anhydrous sodium sulfate to the organic phase, stir and dry, filter, concentrate the organic phase (-0.08-0.09MPa, 55-60°C) until no liquid flows out, stir and add 50mL of a mixed solvent of dichloromethane and petroleum ether, cool 0-5°C, filter, and obtain the intermediate IntM-1-a with a yield of 43%.

[0237] 2) After nitrogen replacement, add intermediate IntM-1-a (10 mmol), intermediate 1-A (10 mmol), potassium carbonate (20 mmol), Pd(PPh3)4 (0.05 mmol), 100 mL of 1,4-dioxane, 30 mL of water, start stirring, and heat to 70-75 ° C for 3 h. Cool down to 25-30 ° C, add 100 mL of water, 100 mL of dichloromethane, stir and separate, extract the aqueous phase with 100 mL of dichloromethane once, separate, combine the organic phases, add 7 g of anhydrous sodium sulfate to the organic phase, stir and dry, filter, concentrate the organic phase (-0.08-0.09 MPa, 55-60 ° C) until no liquid flows out, stir and add 20 mL of petroleum ether, cool 0-5 ° C, filter to obtain a crude product, and recrystallize the crude product from toluene to obtain product M-624 with a yield of 54%.

[0238] Elemental analysis: C 41 H 24 DN3O theoretical value: C, 85.39; H, 4.54; N, 7.29; O, 2.77; found value: C, 85.42; H, 4.55; N, 7.24; HRMS (ESI) m / z [M+H]+: theoretical value: 576.21; found value: 577.32.

[0239] Device Embodiment

[0240] 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).

[0241] The materials for manufacturing the organic electroluminescent device are as follows:

[0242]

[0243]

[0244] The preparation of the organic electroluminescent device comprises the following steps:

[0245] 1) Substrate cleaning:

[0246] The glass substrate coated with transparent ITO is ultrasonically treated in an aqueous cleaning agent (the composition and concentration of the aqueous cleaning agent: ethylene glycol solvent ≤ 10wt%, triethanolamine ≤ 1wt%), 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 the moisture is completely removed, and then cleaned with ultraviolet light and ozone.

[0247] 2) Preparation of organic layer:

[0248] Transfer the ITO transparent substrate to the evaporation equipment and evacuate to 1×10 -6 Up to 2×10 -4 Pa, sequentially deposit hole injection layer (HIL) / hole transport layer (HTL) / luminescent layer (EML) / electron transport layer (ETL) / electron injection layer (EIL) / thick cathode (Al) on the anode film;

[0249] in:

[0250] 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;

[0251] The materials of the hole transport layer (HTL) are shown in Table 5;

[0252] The light-emitting layer (EML) is vacuum evaporated in a co-evaporation manner, and the material of the light-emitting layer includes a host material and a guest material, wherein the guest material is (piq)2Ir(acac), and the specific material of the host material and the ratio of the host material to the guest material are shown in Table 5;

[0253] The materials of the electron transport layer (ETL) are shown in Table 5;

[0254] The material of the electron injection layer (EIL) is LiQ;

[0255] The cathode is aluminum;

[0256] Some layers of the organic electroluminescent device and their materials and thicknesses are shown in Table 5:

[0257] Table 5

[0258]

[0259]

[0260]

[0261]

[0262]

[0263] The embodiments in the table represent device embodiments, and the comparative examples in the table are device comparative examples.

[0264] Test Case

[0265] The organic electroluminescent devices obtained from device examples 1 to 16 and comparative examples 1 to 11 in the device examples were tested.

[0266] Instruments: The current, voltage, brightness and other characteristics of the device are tested synchronously using a PR 650 spectrum scanning brightness meter and a Keithley K2400 digital source meter system;

[0267] Test conditions: Photoelectric characteristics test conditions: Current density is 10mA / cm2.

[0268] 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.

[0269] The device performance test results are shown in Table 6:

[0270] Table 6

[0271]

[0272]

[0273] 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, C disclosed in the prior art, and can have a lower turn-on voltage after being prepared into a device.

[0274] Obviously, the above embodiments are merely examples for the purpose of clear explanation, and are not intended to limit the implementation methods. For those skilled 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 the implementation methods here. The obvious changes or modifications derived therefrom are still within the scope of protection of the 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 shown in formula (1): Wherein, ring A is a benzene ring; Ar is selected from substituted or unsubstituted C6-C25 aryl; L' is selected from phenylene; The second compound has a structure shown in formula (2): Among them, X 1 -X 14 Each is independently selected from N or CR, and R is selected from hydrogen and deuterium; L is independently selected from the linking bond; Ar1 and Ar2 are each independently selected from unsubstituted C6-C25 aryl and unsubstituted C3-C20 heteroaryl; The substituent in the substituted C6-C25 aryl group is selected from deuterium and diphenylamine.

2. The organic material composition according to claim 1, characterized in that: 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, phenalkenyl, phenylnaphthyl, naphthylphenyl, diphenylfluorenyl, spirobifluorenyl.

3. The organic material composition according to claim 1, characterized in that: Ar is selected from phenyl, naphthyl, biphenyl, phenanthrenyl, terphenyl, phenylnaphthyl, naphthylphenyl, diphenylfluorenyl, spirobifluorenyl, phenanthrenyl.

4. The organic material composition according to claim 1, characterized in that: The first compound has any of the following structures:

5. The organic material composition according to any one of claims 1 to 4, characterized in that: In the formula (2), X 1 -X 14 All are selected from CR, and R is defined as in claim 1.

6. The organic material composition according to claim 1, characterized in that: X 1 -X 6 Any one of them is selected from N, the others are CR, and R is defined as in claim 1.

7. The organic material composition according to claim 1, characterized in that: X 1 -X 6 Any one of them is selected from N, and the rest are CR; X 7 -X 14 Any one of them is selected from N, the others are CR, and R is defined as in claim 1.

8. The organic material composition according to claim 1, characterized in that: Ar1 and Ar2 are each independently selected from unsubstituted C6-C15 aryl and unsubstituted C3-C20 heteroaryl.

9. The organic material composition according to claim 1, characterized in that: Ar1 and Ar2 are each independently selected from unsubstituted A groups; The A group includes: phenyl, naphthyl, biphenyl, terphenyl, phenanthryl, fluoranthene, triphenylene, fluorenyl, diphenylfluorenyl, spirobifluorenyl, benzofuranyl, dibenzofuranyl, naphthobenzofuranyl, dinaphthofuranyl, benzothienyl, dibenzothienyl, naphthobenzothienyl, carbazolyl, phenylcarbazolyl, benzophenylcarbazolyl, phenanthrobenzofuranyl.

10. The organic material composition according to claim 1, characterized in that: Ar1 and Ar2 are each independently selected from phenyl, naphthyl, biphenyl, terphenyl, phenanthryl, fluoranthene, triphenylene, fluorenyl, diphenylfluorenyl, spirobifluorenyl, dibenzofuranyl, naphthiobenzofuranyl, dibenzothiophenyl, naphthiobenzothiophenyl, carbazolyl, phenylcarbazolyl, benzocarbazolyl, and dibenzocarbazolyl.

11. The organic material composition according to claim 1, characterized in that: The second compound has a structure as shown in any one of the following formulas 2-1 to 2-28: X 1 -X 14 , Ar1, Ar2 are defined as the same as in claim 1.

12. The organic material composition according to claim 11, characterized in that: The second compound has a structure shown in Formula 2-4 or Formula 2-5.

13. The organic material composition according to claim 11, characterized in that: The second compound has any structure of Formula 2-6, Formula 2-22, Formula 2-25, Formula 2-26, Formula 2-27, Formula 2-28, Formula 2-8 to Formula 2-20.

14. The organic material composition according to claim 1, characterized in that: The second compound has any of the following structures:

15. The organic material composition according to claim 1, characterized in that: In the material composition, the mass ratio of the first compound to the second compound is 1:9-9:

1.

16. The organic material composition according to claim 1, characterized in that: In the material composition, the mass ratio of the first compound to the second compound is 2:8-8:

2.

17. The organic material composition according to claim 1, characterized in that: In the material composition, the mass ratio of the first compound to the second compound is 3:7-7:

3.

18. The organic material composition according to claim 1, characterized in that: In the material composition, the mass ratio of the first compound to the second compound is 4:6-6:

4.

19. An organic electroluminescent host material composition, characterized in that: An organic material composition comprising any one of claims 1 to 18.

20. Use of the organic material composition according to any one of claims 1 to 18 or the organic electroluminescent host material composition according to claim 19 in an optical device.

21. The use according to claim 20, characterized in that The optical device includes an organic electroluminescent device.

22. 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 18 or the organic electroluminescent host material composition according to claim 19.

23. The organic electroluminescent device according to claim 22, characterized in that: The organic layer comprises a light-emitting layer, and the light-emitting layer comprises the organic material composition according to any one of claims 1 to 18 or the organic electroluminescent host material composition according to claim 19.

24. An organic electroluminescent device, characterized in that: Comprising the organic electroluminescent device as claimed in claim 22.

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