An oxazole organic compound containing benzonaphthofuran and its application

Abstract

The present invention relates to the field of display technology, and in particular to an oxazole organic compound containing benzonaphthofuran and its application. The present invention provides an oxazole organic compound containing benzonaphthofuran, which has the following structure: an organic electroluminescent device containing the oxazole organic compound containing benzonaphthofuran can have a lower driving voltage, higher luminous efficiency and longer life.

Description

Technical Field

[0001] The present invention relates to the field of display technology, and in particular to an oxazole organic compound containing benzonaphthofuran and application thereof. Background Art

[0002] An organic electroluminescent device (OLED) is a device that changes electrical energy into light by applying electricity to an organic electroluminescent material, and generally has a structure comprising an anode, a cathode, and an organic layer between the anode and the cathode. The organic layer of the organic EL device can be composed of a hole injection layer, a hole transport layer, an electron blocking layer, a light-emitting layer (which comprises a host material and a doping material), an electron buffer layer, a hole blocking layer, an electron transport layer, an electron injection layer, etc., and the materials used for the organic layer are classified into hole injection materials, hole transport materials, electron blocking materials, light-emitting materials, electron buffer materials, hole blocking materials, electron transport materials, electron injection materials, etc. by their functions. In the organic EL device, due to the application of voltage, holes are injected from the anode into the light-emitting layer, electrons are injected from the cathode into the light-emitting layer, and high-energy excitons are formed by the recombination of holes and electrons. Through this energy, the organic light-emitting compound reaches an excited state, and luminescence is generated by emitting light due to the energy generated by the excited state of the organic light-emitting compound returning to the ground state.

[0003] The most important factor that determines the luminous efficiency in an organic EL device is the luminescent material. The luminescent material must have high quantum efficiency, high electron and hole mobility, and the luminescent material layer formed must be uniform and stable. The luminescent material is divided into blue luminescent material, green luminescent material, and red luminescent material according to the color of the luminescent light, and additionally yellow luminescent material or orange luminescent material. In addition, the luminescent material can also be divided into a host material and a doping material according to its function.

[0004] However, the existing organic electroluminescent materials have low stability, and the HOMO and LUMO energy levels have poor matching with adjacent energy levels, which leads to the problem of unbalanced carrier mobility, which in turn causes the organic electroluminescent devices containing the organic electroluminescent materials to have high driving voltage, low luminous efficiency and short life, which seriously limits the application of organic electroluminescent devices. Summary of the invention

[0005] The purpose of the present invention is to overcome the problem that the existing organic electroluminescent materials have low stability, poor matching between HOMO and LUMO energy levels and adjacent energy levels, resulting in unbalanced carrier mobility, resulting in a high driving voltage, low luminous efficiency and short life of an organic electroluminescent device containing the organic electroluminescent material, and further provide an oxazole organic compound containing benzonaphthofuran and its application.

[0006] Definitions of substituent terms in this invention:

[0007] As used in the present invention, the term "halogen" may include fluorine, chlorine, bromine or iodine.

[0008] 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.

[0009] 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.

[0010] 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.

[0011] 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.

[0012] 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.

[0013] As used herein, unless otherwise specified, hydrogen atoms include protium, deuterium and tritium.

[0014] 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.

[0015] In the present invention, Indicates a connection key.

[0016] The scheme adopted by the present invention is as follows:

[0017] The present invention provides an oxazole organic compound containing benzonaphthofuran, which has a structure shown in the following formula (1):

[0018]

[0019] In the formula (1), ring A is a benzene ring;

[0020] 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;

[0021] L is selected from a substituted or unsubstituted C6-C30 arylene group, a substituted or unsubstituted C3-C30 heteroarylene group;

[0022] The substituents in the substituted C6-C60 aryl group, substituted C6-C60 aromatic amine group, substituted C3-C60 heteroaromatic amine group, substituted C3-C30 heteroaryl group, substituted C6-C30 arylene group and substituted C3-C30 heteroarylene 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 aromatic amine group and C3-C60 heteroaromatic amine group.

[0023] 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.

[0024] Preferably, Ar is selected from substituted or unsubstituted C6-C25 aryl, substituted or unsubstituted C6-C25 arylamine, substituted or unsubstituted C3-C25 heteroarylamine, substituted or unsubstituted C3-C20 heteroaryl;

[0025] 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;

[0026] 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;

[0027] 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, C3-C60 heteroarylamine;

[0028] Preferably, Ar is selected from phenyl, naphthyl, biphenyl, phenyl, phenanthrenyl, terphenyl, phenylnaphthyl, naphthylphenyl, dimethylfluorenyl, diphenylfluorenyl, spirobifluorenyl, phenanthrenyl, dibenzofuranyl, benzonaphthofuranyl, N,N-diphenylanilino.

[0029] 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;

[0030] Preferably, L is selected from phenylene, biphenylene, naphthylene;

[0031] Preferably, L is selected from phenylene and naphthylene.

[0032] Preferably, the formula (1) is selected from one of the structures shown in the following formulas 1-1 to 1-6:

[0033]

[0034] Wherein, Ar has the same definition as above.

[0035] Optionally, the formula (1) is selected from one of the structures shown in the following formulas 1-7 to 1-12:

[0036]

[0037]

[0038] Wherein, Ar has the same definition as above.

[0039] Preferably, the oxazole organic compound containing benzonaphthofuran is selected from any one of the following N-1 to N-208:

[0040]

[0041]

[0042]

[0043]

[0044]

[0045]

[0046]

[0047]

[0048]

[0049] The present invention provides a luminescent host material, comprising the above-mentioned oxazole organic compound containing benzonaphthofuran.

[0050] Preferably, the light-emitting host material comprises a first host material and a second host material, wherein the first host material is the above-mentioned oxazole organic compound containing benzonaphthofuran; and the second host material is an organic electroluminescent compound having the following structure (2):

[0051]

[0052] In the formula (2), Ar1 is selected from substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl;

[0053] The substituents in the substituted C6-C60 aryl group and the substituted C3-C630 heteroaryl group 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 aromatic amine, and C3-C60 heteroaromatic amine.

[0054] Preferably, Ar1 is selected from substituted or unsubstituted C6-C60 non-condensed aryl, substituted or unsubstituted C3-C60 non-condensed heteroaryl;

[0055] The substituents in the substituted C6-C60 non-fused aromatic group and the substituted C3-C60 non-fused heteroaromatic group 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 aromatic group, C3-C30 heteroaromatic group, C6-C60 aromatic amine group, and C3-C60 heteroaromatic amine group.

[0056] Preferably, Ar1 is selected from substituted or unsubstituted C6-C20 non-condensed aryl, substituted or unsubstituted C3-C20 non-condensed heteroaryl;

[0057] The substituents in the substituted C6-C20 non-fused aromatic group and the substituted C3-C20 non-fused heteroaromatic group 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 aromatic group, C3-C30 heteroaromatic group, C6-C60 aromatic amine group, and C3-C60 heteroaromatic amine group.

[0058] Preferably, Ar1 is selected from a substituted or unsubstituted A group, and the A group is selected from one of the following groups: phenyl, biphenyl, terphenyl;

[0059] wherein the substituent in the substituted A group is selected from deuterium, phenyl, and naphthyl;

[0060] Preferably, Ar1 is selected from phenyl, biphenyl, terphenyl, naphthylphenyl.

[0061] Preferably, the organic electroluminescent compound having the structure of the following formula (2) is selected from any one of the following M-1 to M-104:

[0062]

[0063]

[0064]

[0065]

[0066]

[0067] Preferably, the mass ratio of the first main material to the second main material is 9:1-1:9;

[0068] Preferably, the mass ratio of the first main material to the second main material is 2:8-8:2;

[0069] More preferably, the mass ratio of the first main material to the second main material is 3:7-7:3;

[0070] Further preferably, the mass ratio of the first main material to the second main material is 4:6-6:4.

[0071] The present invention also provides an organic electroluminescent material, comprising the above-mentioned oxazole organic compound containing benzonaphthofuran or the above-mentioned luminescent host material.

[0072] The present invention provides an organic electroluminescent device, comprising a cathode, an anode and an organic layer between the cathode and the anode, wherein the organic layer comprises the above-mentioned oxazole organic compound containing benzonaphthofuran or the above-mentioned luminescent host material or the above-mentioned organic electroluminescent material;

[0073] Preferably, the organic layer comprises one or more of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer.

[0074] Preferably, the hole transport layer comprises the above-mentioned oxazole organic compound containing benzonaphthofuran or the above-mentioned luminescent host material or the above-mentioned organic electroluminescent material;

[0075] Preferably, the light-emitting layer comprises the above-mentioned oxazole organic compound containing benzonaphthofuran or the above-mentioned light-emitting host material or the above-mentioned organic electroluminescent material.

[0076] The present invention provides the use of the above-mentioned organic electroluminescent device in optical fiber equipment, lighting equipment, electronic photographic photosensitive body equipment, photoelectric converter, organic solar cell, switch element equipment, organic light-emitting field effect transistor, image sensor or dye laser.

[0077] Beneficial effects of the present invention:

[0078] The oxazole organic compound containing benzonaphthofuran provided by the present invention is based on the structure of formula (1), and further limiting the types of substituents can improve the structural stability of the compound, and the HOMO and LUMO energy levels of the oxazole organic compound containing benzonaphthofuran have a high matching degree with the adjacent energy levels, so that the carrier mobility of the oxazole organic compound containing benzonaphthofuran is relatively balanced, and thus the organic electroluminescent device containing the oxazole organic compound containing benzonaphthofuran has a lower driving voltage, a higher luminous efficiency and a longer life;

[0079] Furthermore, the oxazole organic compound containing benzonaphthofuran provided by the present invention has good electron transport performance and can be used as an electron transport material or a luminescent material;

[0080] Furthermore, the present invention provides an organic electroluminescent material, comprising an oxazole organic compound containing benzonaphthofuran based on the structure of formula (1), so that an organic electroluminescent device comprising the organic electroluminescent material has a lower driving voltage, a higher luminous efficiency and a longer life. BRIEF DESCRIPTION OF THE DRAWINGS

[0081] 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.

[0082] Figure 1 A structural diagram of an organic electroluminescent device in an embodiment of the device of the present invention;

[0083] 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

[0084] 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 inspiration 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.

[0085] 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.

[0086] The term "organic electroluminescent material" in the present disclosure means a material that can be used in an organic electroluminescent device and can contain at least one compound. If necessary, the organic electroluminescent material can be contained in any layer constituting the organic electroluminescent device. For example, the organic electroluminescent material can be a hole injection material, a hole transport material, a hole auxiliary material, a luminescence auxiliary material, an electron blocking material, a luminescent material (containing a host material and a dopant material), an electron buffer material, a hole blocking material, an electron transport material, an electron injection material, etc.

[0087] The term "multiple organic electroluminescent materials" in the present disclosure means one or more organic electroluminescent materials comprising a combination of at least two compounds, which may be included in any layer constituting an organic electroluminescent device. It may mean both 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). For example, a plurality of organic electroluminescent materials may be a combination of at least two compounds, which may be included in at least one of the following: a hole injection layer, a hole transport layer, a hole auxiliary layer, a luminescent auxiliary layer, an electron blocking layer, a luminescent layer, an electron buffer layer, a hole blocking layer, an electron transport layer, and an electron injection layer. At least two compounds may be included in the same layer or in different layers, and may be mixed-evaporated or co-evaporated, or may be evaporated individually.

[0088] In the present invention, the oxazole organic compound containing benzonaphthofuran having the structure of formula (1) is prepared by the following synthetic route:

[0089] 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:

[0090]

[0091] 2. Synthesis of compound Nn: Intermediates Nn-A and Nn-B undergo Buchwald-Hartwig cross-coupling reaction, and the reaction formula is as follows:

[0092]

[0093] In the present invention, the compound represented by the structure of formula (2) is prepared by the following synthetic route:

[0094]

[0095] The intermediate raw materials An, Bn and Cn can be directly purchased or synthesized by conventional reaction pathways and conditions according to methods reported in existing literature.

[0096] The specific structure of the intermediate raw materials used in the embodiments provided by the present invention is as follows:

[0097] The specific structure of Bn is:

[0098]

[0099] The specific structure of Cn is:

[0100]

[0101] Example 1

[0102] 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:

[0103]

[0104] Synthesis of intermediate N1-A

[0105] 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%).

[0106] Synthesis of intermediate N1-B

[0107] 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%).

[0108] Synthesis of Compound N-1

[0109] 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%).

[0110] 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.

[0111] Example 2

[0112] 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:

[0113]

[0114] 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%).

[0115] 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%).

[0116] 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.

[0117] Example 3

[0118] 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:

[0119]

[0120] 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%).

[0121] 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%).

[0122] 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.

[0123] Example 4

[0124] 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:

[0125]

[0126] 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%).

[0127] 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%).

[0128] 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.

[0129] Example 5

[0130] 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:

[0131]

[0132] 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%).

[0133] 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%).

[0134] 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.

[0135] Example 6

[0136] 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:

[0137]

[0138] Synthesis of intermediate N72-A

[0139] 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%).

[0140] Synthesis of intermediate N72-B

[0141] 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%).

[0142] 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%).

[0143] 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.

[0144] Example 7

[0145] 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:

[0146]

[0147] 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%).

[0148] 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%).

[0149] 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%).

[0150] 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.

[0151] Example 8

[0152] 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:

[0153]

[0154] 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%).

[0155] 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.

[0156] Example 9

[0157] 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:

[0158]

[0159] 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%).

[0160] 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%).

[0161] 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.

[0162] Example 10

[0163] This embodiment provides an organic electroluminescent compound N-173. The synthesis of the organic electroluminescent compound N-173 specifically includes the following steps:

[0164]

[0165] 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%).

[0166] 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%).

[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, 85.96; H, 4.48; N, 4.48; HRMS (ESI) m / z [M+H] +: theoretical value: 628.22; found value: 629.24.

[0168] Embodiment 11

[0169] This embodiment provides an organic electroluminescent compound N-182. The synthesis of the organic electroluminescent compound N-182 specifically includes the following steps:

[0170]

[0171] 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%).

[0172] 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%).

[0173] 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%).

[0174] 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.

[0175] Example 12

[0176]

[0177] After nitrogen replacement of a three-mouth reaction bottle equipped with mechanical stirring, a thermometer, and a condenser, intermediate 8.94g N182-A (29.31mmol), 4.96g N173-3 (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%).

[0178] 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%).

[0179] 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.

[0180] 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.

[0181] Table 1

[0182]

[0183]

[0184] The characterization data of the products prepared in Examples 13-21 are shown in Table 2:

[0185] Table 2

[0186]

[0187] Embodiment 22

[0188] This embodiment provides an organic electroluminescent compound M-3 in a luminescent host material. The synthesis of the organic electroluminescent compound M-3 specifically includes the following steps:

[0189]

[0190] Take a 100 ml three-necked round-bottom flask and put in a stirring bar and a reflux tube. Under nitrogen protection, add raw material A-3 (1 mmol), 2,4-dichloro-6-phenyl-1,3,5-triazine (1.2 mmol), Pd(dppf)Cl2 (0.03 mmol), potassium carbonate (2.5 mmol), 1,4-dioxane / water (10 mL / 2 mL) in sequence, heat to 60 degrees Celsius and react for 5 hours. After the reaction is completed, cool to room temperature, quench with saturated ammonium chloride aqueous solution, extract with ethyl acetate, dry the organic phase with anhydrous magnesium sulfate, use a rotary evaporator to remove the solvent, and separate the crude product by column chromatography (ethyl acetate: n-hexane = 1:50) to obtain intermediate M-3-1 (yield 61%).

[0191] Take a 100 ml three-necked round-bottom flask and put in a stirring bar and a reflux tube. Under nitrogen protection, add the intermediate M-3-1 (1 mmol), 4,4,5,5-tetramethyl-2-(naphtho[2,1-b]benzofuran-1-yl)-1,3,2-dioxaborane, i.e. C-1 (1.2 mmol), Pd(dppf)Cl2 (0.03 mmol), potassium carbonate (2.5 mmol), 1,4-dioxane / water (10 mL / 2 mL) in sequence, heat to 90 degrees Celsius and react for 5 hours. After the reaction is completed, cool to room temperature, filter, rinse the filter cake twice with deionized water and twice with ethanol, and the crude product is purified twice by recrystallization with o-dichlorobenzene to obtain the organic electroluminescent compound M-3 (yield 42%).

[0192] Elemental analysis: C 41 H 25 N3. Theoretical value: C, 85.54; H, 4.38; N, 7.30; O, 2.78; Found value: C, 85.48; H, 4.50; N, 7.24; HRMS (ESI) m / z [M+H] + : Theoretical value: 575.20; measured value: 576.20.

[0193] Embodiment 23

[0194] This embodiment provides an organic electroluminescent compound M-54 in a luminescent host material. The synthesis of the organic electroluminescent compound M-54 specifically includes the following steps:

[0195]

[0196] Take a 100 ml three-necked round-bottom flask and put in a stirring bar and a reflux tube. Under nitrogen protection, add raw material A-54 (1 mmol), 2,4-dichloro-6-phenyl-1,3,5-triazine (1.2 mmol), Pd(dppf)Cl2 (0.03 mmol), potassium carbonate (2.5 mmol), 1,4-dioxane / water (10 mL / 2 mL) in sequence, heat to 60 degrees Celsius and react for 5 hours. After the reaction is completed, cool to room temperature, quench with saturated ammonium chloride aqueous solution, extract with ethyl acetate, dry the organic phase with anhydrous magnesium sulfate, use a rotary evaporator to remove the solvent, and separate the crude product by column chromatography (ethyl acetate: n-hexane = 1:50) to obtain intermediate M-54-1 (yield 45%).

[0197] Take a 100 ml three-necked round-bottom flask and put in a stirring bar and a reflux tube. Under nitrogen protection, add intermediate M-54-1 (1 mmol), 4,4,5,5-tetramethyl-2-(naphtho[2,1-b]benzofuran-5-yl)-1,3,2-dioxaborane, i.e. C-4 (1.2 mmol), Pd(dppf)Cl2 (0.03 mmol), potassium carbonate (2.5 mmol), 1,4-dioxane / water (10 mL / 2 mL) in sequence, heat to 90 degrees Celsius and react for 5 hours. After the reaction is completed, cool to room temperature, filter, rinse the filter cake twice with deionized water and twice with ethanol, and then purify the crude product twice by recrystallization with o-dichlorobenzene to obtain organic electroluminescent compound 54 (yield 46%).

[0198] Elemental analysis: C 41 H 25 N3. Theoretical value: C, 85.54; H, 4.38; N, 7.30; O, 2.78; Found: C, 85.44; H, 4.54; N, 7.24; HRMS (ESI) m / z [M+H] +: Theoretical value: 575.20; measured value: 576.20.

[0199] Embodiment 24

[0200] This embodiment provides an organic electroluminescent compound M-58 in a light-emitting host material. The synthesis of the organic electroluminescent compound M-58 specifically includes the following steps:

[0201]

[0202] Take a 100 ml three-necked round-bottom flask and put in a stirring bar and a reflux tube. Under nitrogen protection, add raw material A-58 (1mmol), 2-([1,1'-biphenyl]-3-yl)-4,6-dichloro-1,3,5-triazine, i.e. B-2 (1.2mmol), Pd(dppf)Cl2 (0.03mmol), potassium carbonate (2.5mmol), 1,4-dioxane / water (10mL / 2mL) in sequence, heat to 60 degrees Celsius and react for 5 hours. After the reaction is completed, cool to room temperature, quench with saturated ammonium chloride aqueous solution, extract with ethyl acetate, dry the organic phase with anhydrous magnesium sulfate, use a rotary evaporator to remove the solvent, and separate the crude product by column chromatography (ethyl acetate: n-hexane = 1:50) to obtain intermediate M-59-1 (yield 54%).

[0203] Take a 100 ml three-necked round-bottom flask and put in a stirring bar and a reflux tube. Under nitrogen protection, add the intermediate M-59-1 (1 mmol), 4,4,5,5-tetramethyl-2-(naphtho[2,1-b]benzofuran-2-yl)-1,3,2-dioxaborane, i.e. C-3 (1.2 mmol), Pd(dppf)Cl2 (0.03 mmol), potassium carbonate (2.5 mmol), 1,4-dioxane / water (10 mL / 2 mL) in sequence, heat to 90 degrees Celsius and react for 5 hours. After the reaction is completed, cool to room temperature, filter, rinse the filter cake twice with deionized water and twice with ethanol, and then purify the crude product twice by recrystallization with o-dichlorobenzene to obtain the organic electroluminescent compound M-58 (yield 71%).

[0204] Elemental analysis: C 47 H 29 N3. Theoretical value: C, 86.61; H, 4.49; N, 6.45; O, 2.45; Found: C, 86.53; H, 4.59; N, 6.41; HRMS (ESI) m / z [M+H] + : Theoretical value: 651.23; measured value: 652.24.

[0205] Embodiment 25

[0206] This embodiment provides an organic electroluminescent compound M-66 in a luminescent host material. The synthesis of the organic electroluminescent compound M-66 specifically includes the following steps:

[0207]

[0208] Take a 100 ml three-necked round-bottom flask and put in a stirring bar and a reflux tube. Under nitrogen protection, add raw material A-66 (1 mmol), 2-([1,1':2',1'-triphenyl]-3-yl)-4,6-dichloro-1,3,5-triazine, i.e. B-5 (1.2 mmol), Pd(dppf)Cl2 (0.03 mmol), potassium carbonate (2.5 mmol), 1,4-dioxane / water (10 mL / 2 mL) in sequence, heat to 60 degrees Celsius and react for 5 hours. After the reaction is completed, cool to room temperature, quench with saturated ammonium chloride aqueous solution, extract with ethyl acetate, dry the organic phase with anhydrous magnesium sulfate, use a rotary evaporator to remove the solvent, and separate the crude product by column chromatography (ethyl acetate: n-hexane = 1:50) to obtain intermediate M-66-1 (yield 49%).

[0209] Take a 100 ml three-necked round-bottom flask and put in a stirring bar and a reflux tube. Under nitrogen protection, add intermediate M-66-1 (1 mmol), 4,4,5,5-tetramethyl-2-(naphtho[2,1-b]benzofuran-2-yl)-1,3,2-dioxaborane, i.e. C-1 (1.2 mmol), Pd(dppf)Cl2 (0.03 mmol), potassium carbonate (2.5 mmol), 1,4-dioxane / water (10 mL / 2 mL) in sequence, heat to 90 degrees Celsius and react for 5 hours. After the reaction is completed, cool to room temperature, filter, rinse the filter cake twice with deionized water and twice with ethanol, and the crude product is purified twice by recrystallization from o-dichlorobenzene to obtain compound M-66 (yield 57%).

[0210] Elemental analysis: C 53 H 33 N3O. Theoretical value: C, 87.46; H, 4.57; N, 5.77; O, 2.20; Found value: C, 87.33; H, 4.79; N, 5.68; HRMS (ESI) m / z [M+H] + : Theoretical value: 727.26; measured value: 728.24.

[0211] The preparation methods of Examples 26-33 are similar to that of Example 22. Specifically, the raw materials used in Examples 26-33 and the products obtained are shown in Table 3 below.

[0212] Table 3

[0213]

[0214]

[0215]

[0216] The product characterization data obtained in Examples 26-33 are shown in Table 4:

[0217] Table 4

[0218]

[0219] Device Embodiment

[0220] 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).

[0221] The materials for manufacturing the organic electroluminescent device are as follows:

[0222]

[0223]

[0224] The preparation method of compound B is the same as that of the oxazole organic compound N-1 containing benzonaphthofuran, except that By replacing intermediate N1-A, compound B was obtained (yield 64%).

[0225] Elemental analysis: C 35 H 22 N2O2; theoretical value: C, 83.65; H, 4.41; N, 5.57; O, 6.37; found value: C, 83.62; H, 4.41; N, 5.61; HRMS (ESI) m / z [M+H] +: theoretical value: 502.17; found value: 503.32.

[0226] The preparation method of compound C is the same as that of electroluminescent compound N-1, except that Substitute raw material N1-3, Substituting raw material N1-4, compound C was obtained (yield 60%).

[0227] Elemental analysis: C 57 H 35N3O2; theoretical value: C, 86.23; H, 4.44; N, 5.29; O, 4.03; found value: C, 86.28; H, 4.47; N, 5.21; HRMS (ESI) m / z [M+H] +: theoretical value: 793.27; found value: 794.25.

[0228] The preparation of the organic electroluminescent device comprises the following steps:

[0229] 1) Substrate cleaning:

[0230] 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.

[0231] 2) Preparation of organic layer:

[0232] Transfer the ITO transparent substrate to the evaporation equipment and evacuate to 1×10 -6 Up to 2×10 -4 Pa, hole injection layer (HIL) / hole transport layer (HTL) / light emitting layer (EML) / electron transport layer (ETL) / electron injection layer (EIL) / thick cathode (Al) are sequentially deposited on the anode film.

[0233] in:

[0234] 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;

[0235] The materials of the hole transport layer (HTL) are shown in Table 5;

[0236] 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;

[0237] The materials of the electron transport layer (ETL) are shown in Table 5;

[0238] The material of the electron injection layer (EIL) is LiQ;

[0239] The cathode is aluminum;

[0240] The materials and thicknesses of some layers of the organic electroluminescent device are shown in Table 5

[0241] Table 5

[0242]

[0243]

[0244]

[0245]

[0246]

[0247] The embodiments in the table represent device embodiments, and the comparative examples in the table are device comparative examples.

[0248] Test Case

[0249] The organic electroluminescent devices obtained from device examples 1 to 24 and comparative examples 1 to 6 in the device examples were tested.

[0250] Instruments: The device's current, voltage, brightness, luminous spectrum and other characteristics are tested synchronously using a PR 650 spectrum scanning luminance meter and a Keithley K2400 digital source meter system;

[0251] Test conditions: Photoelectric characteristics test conditions: Current density is 10mA / cm2.

[0252] 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.

[0253] The device performance test results are shown in Table 6:

[0254] Table 6

[0255]

[0256]

[0257] The embodiments in the table represent device embodiments, and the comparative examples in the table are device comparative examples.

[0258] 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 oxazole organic compound containing benzonaphthofuran, characterized in that: It has the structure shown in the following formula (1): In the formula (1), ring A is a benzene ring; Ar is selected from substituted or unsubstituted C6-C60 aryl; L is selected from substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene; Wherein, the substituent in the substituted phenylene and substituted naphthylene is selected from deuterium; The substituent in the substituted C6-C60 aromatic group is selected from one or a combination of at least two of deuterium, phenyl and diphenylamine.

2. The oxazole organic compound containing benzonaphthofuran according to claim 1, characterized in that: Ar is selected from substituted or unsubstituted C6-C25 aryl; The substituent in the substituted C6-C25 aromatic group is selected from one or a combination of at least two of deuterium, phenyl and diphenylamine.

3. The oxazole organic compound containing benzonaphthofuran 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, 1,2-diphenylfluorenyl, 1,2-diphenylfluorenyl, 1,2-diphenylfluorenyl, 1,2-diphenylfluorenyl, 1,2-diphenylfluorenyl, 1,2-diphenylspirobifluorenyl; The substituent of the substituted B group is selected from one or a combination of at least two of deuterium, phenyl, and diphenylamine.

4. The oxazole organic compound containing benzonaphthofuran according to claim 1, characterized in that: Ar is selected from phenyl, naphthyl, biphenyl, phenyl, phenanthrenyl, terphenyl, phenylnaphthyl, naphthylphenyl, diphenylfluorenyl, spirobifluorenyl.

5. The benzonaphthofuran-containing oxazole organic compound according to claim 1, characterized in that: L is selected from phenylene and naphthylene.

6. The oxazole organic compound containing benzonaphthofuran according to claim 1, characterized in that: The formula (1) is selected from one of the structures shown in the following formulas 1-1 to 1-6: Wherein, Ar is defined as in claim 1.

7. An oxazole organic compound containing benzonaphthofuran, characterized in that: The oxazole organic compound containing benzonaphthofuran is selected from any one of the following N-1 to N-208:

8. A light-emitting host material, characterized in that: The invention comprises the oxazole organic compound containing benzonaphthofuran as described in any one of claims 1 to 7.

9. The light-emitting host material according to claim 8, characterized in that: The light-emitting host material comprises a first host material and a second host material, wherein the first host material is an oxazole organic compound containing benzonaphthofuran according to any one of claims 1 to 7; and the second host material is an organic electroluminescent compound having the following structure (2): In the formula (2), Ar1 is selected from substituted or unsubstituted C6-C60 aryl groups; The substituents in the substituted C6-C60 aromatic group 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 aromatic group, C3-C30 heteroaromatic group, C6-C60 aromatic amine group, and C3-C60 heteroaromatic amine group.

10. The light-emitting host material according to claim 9, characterized in that: Ar1 is selected from substituted or unsubstituted C6-C60 non-fused aromatic groups; The substituents in the substituted C6-C60 non-fused aromatic group 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 aromatic amine, and C3-C60 heteroaromatic amine.

11. The light-emitting host material according to claim 9, characterized in that: Ar1 is selected from substituted or unsubstituted C6-C20 non-fused aromatic groups; The substituents in the substituted C6-C20 non-fused aromatic group 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 aromatic amine, and C3-C60 heteroaromatic amine.

12. The light-emitting host material according to claim 9, characterized in that: Ar1 is selected from a substituted or unsubstituted A group, and the A group is selected from one of the following groups: phenyl, biphenyl, terphenyl; The substituent in the substituted A group is selected from deuterium, phenyl and naphthyl.

13. The light-emitting host material according to claim 9, characterized in that: Ar1 is selected from phenyl, biphenyl, terphenyl, naphthylphenyl.

14. The light-emitting host material according to claim 9, characterized in that: The mass ratio of the first main material to the second main material is 9:1-1:

9.

15. The light-emitting host material according to claim 9, characterized in that: The mass ratio of the first main material to the second main material is 2:8-8:

2.

16. The light-emitting host material according to claim 9, characterized in that: The mass ratio of the first main material to the second main material is 3:7-7:

3.

17. The light-emitting host material according to claim 9, characterized in that: The mass ratio of the first main material to the second main material is 4:6-6:

4.

18. An organic electroluminescent material, characterized in that: The invention comprises an oxazole organic compound containing benzonaphthofuran as described in any one of claims 1 to 7 or a light-emitting host material as described in any one of claims 8 to 17.

19. An organic electroluminescent device, characterized in that: The organic electroluminescent device comprises a cathode, an anode and an organic layer located between the cathode and the anode, wherein the organic layer comprises a light-emitting layer, and the light-emitting layer comprises the benzonaphthofuran-containing oxazole organic compound according to any one of claims 1 to 7 or the light-emitting host material according to any one of claims 8 to 17 or the organic electroluminescent material according to claim 18.

20. Use of the organic electroluminescent device according to claim 19 in optical fiber equipment, lighting equipment, electrophotographic photosensitive body equipment, photoelectric converter, organic solar cell, switching element equipment, organic light emitting field effect transistor, image sensor or dye laser.

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