Organic compound and application thereof

Abstract

The invention provides an organic compound and application thereof, the organic compound has a structure as shown in a formula I. The introduction of naphthylene in the organic compound can adjust the energy level and change the molecular configuration, and the structural characteristics of the organic compound are beneficial to increase of the glass transition temperature of molecules, so that the organic compound has a good application prospect. And meanwhile, the evaporation temperature of molecules can be reduced, that is, even if the molecular weight of the structure is relatively high, a relatively low evaporation temperature can be ensured, and the excellent performance is beneficial to thermal evaporation of the material and control of the thermal decomposition rate of the material, so that the stability of the material in device application is improved. Devices using the organic compound of the present invention have low driving voltage, high current efficiency and long life.

Description

Technical Field

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

[0002] Organic electroluminescent devices (OLEDs) convert electrical energy into light by applying power to organic electroluminescent materials, and generally include an anode, a cathode, and an organic layer formed between the two electrodes. The organic layer of the organic electroluminescent device may include a hole injection layer, a hole transport layer, a hole auxiliary layer, a luminescent auxiliary layer, an electron blocking layer, a luminescent layer (containing a host material and a dopant material), an electron buffer layer, a hole blocking layer, an electron transport layer, an electron injection layer, etc. Based on the functions achieved by each layer, the various materials used in the organic layer are 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. In an organic electroluminescent device, holes from the anode and electrons from the cathode are injected into the luminescent layer by applying a voltage, and excitons with high energy are generated by the recombination of holes and electrons. The organic light-emitting compound moves to an excited state by energy and emits light by the energy when the organic light-emitting compound returns to the ground state from the excited state.

[0003] As displays become larger in area, driving voltage increases, and problems such as low luminous efficiency and short lifespan emerge, severely limiting the application of organic electroluminescent devices. Therefore, organic materials must solve these efficiency or lifespan problems, and it is necessary to continuously develop new materials for organic light-emitting devices that are highly efficient, have a long lifespan, and are suitable for mass production. Summary of the invention

[0004] In view of the deficiencies in the prior art, the present invention aims to provide an organic compound and application thereof.

[0005] In order to achieve the purpose of the invention, the present invention adopts the following technical solutions:

[0006] In one aspect, the present invention provides an organic compound having a structure shown in Formula I:

[0007]

[0008] X is selected from O or S,

[0009] L is selected from naphthylene,

[0010] L 1 , L 2 is selected from a connecting bond, a substituted or unsubstituted C6-C30 arylene group, a substituted or unsubstituted C3-C30 heteroarylene group,

[0011] Ar 1 -Ar 3 are each independently selected from hydrogen, deuterium, protium, halogen, cyano, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C6-C60 arylamine, substituted or unsubstituted C3-C60 heteroarylamine and substituted or unsubstituted C3-C60 heteroaryl,

[0012] The substituents of the substituted C6-C30 arylene group, C3-C30 heteroarylene group, substituted C6-C30 aryl group, substituted C3-C30 heteroaryl group, substituted C6-C60 aromatic amine group and substituted C3-C60 heteroaromatic amine 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 heteroaromatic group, C6-C60 aromatic amine group and C3-C60 heteroaromatic amine group.

[0013] Preferably, Ar 1 and Ar 2 Each is independently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted phenyl, naphthyl, biphenyl, phenanthrenyl, fluoranthenyl, yl, terphenyl, triphenylene, phenylnaphthyl, naphthylphenyl, dimethylfluorenyl, phenylmethylfluorenyl, diphenylfluorenyl, carbazolyl, benzocarbazolyl, phenylcarbazolyl, phenylbenzocarbazolyl, phenylphenanthrocarbazolyl, 9-phenyl-9H-dibenzo[a,c]carbazolyl, spiro[fluorene-9,9'-xanthene]yl, pyridyl, pyridylphenyl, phenylpyridyl, spirobifluorenyl, benzodimethylfluorenyl, benzodiphenylfluorenyl, benzospirobifluorenyl, dibenzo furanyl, benzonaphthofuranyl, benzonaphthothiophenyl, dibenzothiophenyl, diphenylamino, diphenylamino, N-phenyl-benzidine and N-phenyl-dibenzofuranamino; the substituents are each independently selected from one or a combination of at least two of deuterium, halogen, cyano, C1-C6 alkyl, C3-C12 cycloalkyl, C6-C25 aryl, C3-C25 heteroaryl, C6-C60 arylamine, C3-C60 heteroarylamine;

[0014] Preferably, L 1 and L 2 Each is independently selected from a linker, a phenylene group or a naphthylene group.

[0015] Preferably, Ar 1 and Ar 2 Each independently selected from phenyl, fluorophenyl, cyano-substituted phenyl, naphthyl, phenanthryl, biphenyl, phenyl, terphenyl, phenylnaphthyl, naphthylphenyl, dimethylfluorenyl, diphenylfluorenyl, phenylbenzocarbazolyl, phenylphenanthrocarbazolyl, spiro[fluorene-9,9'-xanthene]yl, spirobifluorenyl, phenylmethylfluorenyl, dibenzofuranyl, benzonaphthofuranyl, diphenylamino, N-phenyl-benzidine or The wavy line represents the attachment site of the group, and D represents deuterium.

[0016] Preferably, Ar 3 Selected from phenyl or naphthyl.

[0017] Preferably, Ar 1 and Ar 2 Each independently selected from any one of the following groups (fragment of aromatic amine group):

[0018]

[0019]

[0020] Indicates a connection key.

[0021] Preferably, the organic compound is any one of M-1 to M-764:

[0022]

[0023]

[0024]

[0025]

[0026]

[0027]

[0028]

[0029]

[0030]

[0031]

[0032]

[0033]

[0034]

[0035]

[0036]

[0037]

[0038]

[0039]

[0040]

[0041]

[0042]

[0043]

[0044]

[0045]

[0046]

[0047]

[0048]

[0049] Where D stands for deuterium.

[0050] Definition of Substituent Terms

[0051] As used in the present invention, the term "halogen" may include fluorine, chlorine, bromine or iodine.

[0052] 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.

[0053] 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.

[0054] In the present invention, the 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, including but not limited to phenyl, biphenyl, terphenyl, naphthyl, phenanthrenyl, anthracenyl, fluorenyl, spirobifluorenyl, etc.

[0055] In the present invention, the heteroaryl and heteroarylene group include monocyclic, polycyclic or condensed-ring heteroaryl groups. The rings may be interrupted by short non-aromatic units. The heteroatoms include nitrogen, oxygen and sulfur. Including but not limited to furanyl, phenylthio, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetrazinyl, triazolyl, tetrazolyl, furazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, benzofuranyl, benzothiophenyl, isobenzofuranyl, dibenzofuranyl, dibenzothiophenyl, benzimidazolyl, benzothiazolyl, benzisothiazolyl, benzisoxazolyl, benzoxazolyl, isoindolyl, indolyl, indazolyl, benzothiadiazolyl, quinolyl, isoquinolyl, cinnolinyl, quinazolinyl, quinoxalinyl, carbazolyl, phenoxazinyl, phenothiazinyl, phenanthridinyl, benzodioxolyl, dihydroacridinyl, and derivatives thereof.

[0056] 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.

[0057] As used herein, unless otherwise specified, hydrogen atoms include protium, deuterium and tritium.

[0058] In the present invention, the range of carbon number is defined in the definition of the group, and the carbon number is any integer within the defined range. For example, C6-C60 aromatic group, the carbon number of aromatic group can be any integer within the range of 6-60, for example 6, 8, 10, 13, 15, 17, 20, 22, 25, 30, 35, 38, 40, 42, 44, 48, 50, 53, 55, 58 or 60, etc.

[0059] As used herein, "multiple host materials" 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 various host materials disclosed herein may be contained in any light-emitting layer constituting an organic electroluminescent device. Two or more compounds contained in the various host materials disclosed herein 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.

[0060] In the present invention, the organic compound represented by formula I can be prepared by the following synthetic route:

[0061] 1. Synthesis of intermediate nA:

[0062] The reaction raw materials Mn-Aa and Mn-Ab undergo Suzuki cross-coupling reaction:

[0063]

[0064] 2. Synthesis of Compound M

[0065] The intermediate Mn-A and Mn-B undergo Buchwald-Hartwig cross-coupling reaction:

[0066]

[0067] In another aspect, the present invention provides an organic electroluminescent material, which comprises the organic compound as described above.

[0068] On the other hand, the present invention provides a plurality of host materials, wherein the plurality of host materials include at least one organic compound as described above as a first host material and at least one second host material represented by a compound N, wherein the structure of the compound N is represented by the following formula N:

[0069]

[0070] In formula N, R is selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl,

[0071] R 1 Selected from -L 1 Ar 1 , R 2 Selected from -L 2 Ar 2 , R 3 Selected from -L 3 Ar 3 , R 4 Selected from -L 4 Ar 4 ,

[0072] L 1 -L 4 are each independently selected from a connecting bond, a substituted or unsubstituted C6-C30 arylene group, and a substituted or unsubstituted C3-C30 heteroarylene group,

[0073] Ar 1 -Ar 4Each is independently selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C6-C60 arylamine, substituted or unsubstituted C3-C60 heteroarylamine, substituted or unsubstituted C6-C60 arylC3-C60 heteroarylamine, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl;

[0074] Preferably, Ar 1 -Ar 4 Each is independently selected from the following substituted or unsubstituted groups: hydrogen, deuterium, phenyl, naphthyl, biphenyl, terphenyl, phenanthryl, fluoranthenyl, triphenylene, dimethylfluorenyl, diphenylfluorenyl, spirobifluorenyl, benzodimethylfluorenyl, benzodiphenylfluorenyl, benzospirobifluorenyl, dibenzofuranyl or dibenzothiophenyl;

[0075] Preferably, in Formula 1, the R 1 , R 2 , R 3 , R 4 At least one selected from hydrogen;

[0076] Preferably, the R 1 , R 2 , R 3 , R 4 At least two items are selected from hydrogen;

[0077] Preferably, the R 1 , R 2 , R 3 , R 4 Three of them are selected from hydrogen;

[0078] Preferably, the R 2 Selected from L 2 Ar 2 , R 1 , R 3 , R 4 are all selected from hydrogen;

[0079] Preferably, the R 3 Selected from L 3 Ar 3 , R 1 , R 2 , R 4 are all selected from hydrogen;

[0080] Preferably, R is selected from the following substituted or unsubstituted groups: phenyl, biphenyl;

[0081] Preferably, L 1 -L 4 Each is independently selected from a linking bond, a substituted or unsubstituted phenylene group, a naphthylene group or a biphenylene group, a substituted or unsubstituted terphenylene group, and a substituted or unsubstituted naphthylene group.

[0082] Preferably, the weight ratio of the first host material to the second host material is 1:99-99:1, such as 1:99, 20:80, 30:70, 40:60, 50:50, 60:40, 70:30, 80:20, 90:10, 99:1, etc., preferably about 10:90-90:10, more preferably 30:70-70:30, even more preferably 40:60-60:40, and still more preferably 50:50. When two or more materials are included in one layer, they can be mixed and evaporated to form a layer, or can be co-evaporated separately at the same time to form a layer.

[0083] On the other hand, the present invention provides an organic electroluminescent device, which includes a cathode, an anode and an organic layer located between the cathode and the anode, wherein the organic layer contains the organic compound as described above or the organic electroluminescent material as described above or the multiple host materials as described above.

[0084] Preferably, the organic layer comprises a hole transport layer, and the hole transport layer comprises the organic compound as described above or the organic electroluminescent material as described above.

[0085] Preferably, the organic layer comprises a light-emitting layer, and the light-emitting layer comprises the organic compound as described above or the organic electroluminescent material as described above or the plurality of host materials as described above.

[0086] Preferably, the organic layer further comprises one or a combination of at least two of a hole injection layer, a light emitting layer, an electron transport layer, an electron blocking layer, an electron buffer layer or an electron injection layer.

[0087] On the other hand, the present invention provides the use of the organic electroluminescent device as described above in an optical fiber device, a lighting device, an electrophotographic photoreceptor device, a photoelectric converter, an organic solar cell, a switching element device, an organic light-emitting field effect transistor, an image sensor or a dye laser.

[0088] Compared with the prior art, the present invention has the following beneficial effects:

[0089] The organic compound of the present invention adjusts the spatial configuration of the parent core by adjusting the position of the fused benzene ring in naphthoxazolyl, so that the planarity of the molecular structure is better, which is conducive to the transmission of carriers. The parent core structure has hole transport performance by connecting with aromatic amine, and the HOMO, LUMO and triplet energy levels of the structure are regulated by molecular modification, so that the series of compounds have better matching, and can effectively reduce the driving voltage of the device containing the organic compound of the present invention, improve the current efficiency and extend the life of the device.

[0090] On the other hand, the introduction of naphthylene in the organic compound of the present invention can adjust the energy level and change the molecular configuration. The structural characteristics of the organic compound of the present invention are conducive to improving the glass transition temperature of the molecule and reducing the evaporation temperature of the molecule. That is to say, even if the molecular weight of the structure is relatively high, it can ensure a lower evaporation temperature. This excellent performance is not only conducive to the thermal evaporation of the material, but also controls the thermal decomposition rate of the material, thereby improving the stability of the material in device application. The device using the organic compound of the present invention has a lower driving voltage, a higher current efficiency and a longer life. BRIEF DESCRIPTION OF THE DRAWINGS

[0091] Figure 1 is a schematic structural diagram of the organic electroluminescent device of the present invention;

[0092] Among them, 1 is a substrate, 2 is an anode, 3 is a hole injection layer, 4 is a hole transport layer, 5 is a light emitting layer, 6 is an electron transport layer, 7 is an electron injection layer, and 8 is a cathode. DETAILED DESCRIPTION

[0093] The technical solution of the present invention is further described below by specific implementation methods. It should be understood by those skilled in the art that the embodiments are only to help understand the present invention and should not be regarded as specific limitations of the present invention.

[0094] Synthesis Example

[0095] The compounds not mentioned in the following synthesis can be obtained by commercial purchase or by the operation or conditions of conventional experimental steps described in the literature in the field.

[0096] 1. Synthesis of intermediates

[0097] Synthesis of intermediate M1-A

[0098]

[0099] After nitrogen replacement, add intermediate M1-Aa (10mmol), intermediate M1-Ab (10mmol), 100mL toluene, 20mL ethanol, 20mL water, potassium carbonate (20mmol), Pd(PPh3)4 (0.05mmol) in sequence to a three-mouth reaction bottle 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 water, 100mL toluene, stir and separate, extract the aqueous phase once with 100mL toluene, separate, combine the organic phases, add 7g 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 to 0-5°C, filter, and obtain compound M1-A with a yield of 47%.

[0100] Elemental analysis: C 27 H 16 ClNO theoretical value: C, 79.90; H, 3.97; Cl, ​​8.73; N, 3.45; O, 3.94; found value: C, 79.87; H, 3.95; Cl, ​​8.72; N, 3.49; HRMS (ESI) m / z [M+H] +: theoretical value: 405.09; found value: 406.14.

[0101] The preparation of the following intermediates M2-A to M12-A is the same as that of M1-A, except that the raw materials M1-Aa substituted with bromine and chlorine at different positions and M1-Ab substituted with boronate at different positions are used:

[0102]

[0103] Example 1

[0104] Synthesis route of M-1

[0105]

[0106] After nitrogen substitution in a three-necked reaction flask equipped with a mechanical stirrer, a thermometer and a condenser, intermediate M1-B (10 mmol), intermediate M1-A (10 mmol) and 100 mL of toluene were added in sequence, heated to reflux to remove water for 0.5 h, cooled to 70-80 °C, sodium tert-butoxide (15 mmol), Pd2(dba)3 (0.05 mmol) and s-phos (0.1 mmol) were slowly added, and after the system was stabilized, it was heated to 100-110 °C and reacted for 3 h. Cool to 25-30°C, add 100 mL of water and 100 mL of toluene, stir and separate the liquids, extract the aqueous phase once with 100 mL of toluene, separate the liquids, 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 to 0-5°C, filter, and obtain compound M-1 with a yield of 74%.

[0107] Elemental analysis: C39H26N2O theoretical value: C, 86.96; H, 4.87; N, 5.20; O, 2.97; found value: C, 86.74; H, 4.93; N, 5.36; HRMS (ESI) m / z [M+H] +: theoretical value: 538.20; found value: 539.19.

[0108] Example 2

[0109] Synthesis route of M-6

[0110]

[0111] After nitrogen substitution in a three-necked reaction flask equipped with a mechanical stirrer, a thermometer and a condenser, intermediate M6-B (10 mmol), intermediate M1-A (10 mmol) and 100 mL of toluene were added in sequence, heated to reflux to remove water for 0.5 h, cooled to 70-80 °C, sodium tert-butoxide (15 mmol), Pd2(dba)3 (0.05 mmol) and s-phos (0.1 mmol) were slowly added, and after the system was stabilized, it was heated to 100-110 °C and reacted for 3 h. The temperature was lowered to 25-30°C, 100 mL of water and 100 mL of toluene were added, and the mixture was stirred and separated. The aqueous phase was extracted once with 100 mL of toluene, and the mixture was separated. The organic phases were combined, 7 g of anhydrous sodium sulfate was added to the organic phase, and the mixture was stirred and dried. The organic phase was filtered and concentrated (-0.08-0.09 MPa, 55-60°C) until no liquid flowed out. 20 mL of petroleum ether was added with stirring, the temperature was lowered to 0-5°C, and the mixture was filtered to obtain compound N-6 with a yield of 61%.

[0112] Elemental analysis: C51H32N2O2 theoretical value: C, 86.91; H, 4.58; N, 3.97; O, 4.54; found value: C, 86.86; H, 4.62; N, 4.01; HRMS (ESI) m / z [M+H] +: theoretical value: 704.25; found value: 705.26.

[0113] Example 3

[0114] Synthesis route of M-14

[0115]

[0116] After nitrogen substitution in a three-necked reaction flask equipped with mechanical stirring, thermometer and condenser, add intermediate M14-B (10 mmol), intermediate M1-A (10 mmol) and 100 mL of toluene in sequence, heat to reflux to separate water for 0.5 h, cool to 70-80 °C, slowly add sodium tert-butoxide (15 mmol), Pd2(dba)3 (0.05 mmol) and s-phos (0.1 mmol), and heat to 100-110 °C for reaction for 3 h after the system is stable. Cool to 25-30°C, add 100 mL of water and 100 mL of toluene, stir and separate the liquids, extract the aqueous phase once with 100 mL of toluene, separate the liquids, 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 to 0-5°C, filter, and obtain compound N-14 with a yield of 45%.

[0117] Elemental analysis: C63H40N3O2 theoretical value: C, 85.02; H, 4.53; F, 2.13; N, 4.72; O, 3.60; found value: C, 85.06; H, 4.54; F, 2.09; N, 4.71; HRMS (ESI) m / z [M+H] +: theoretical value: 889.31; found value: 890.28.

[0118] Example 4

[0119] Synthesis route of M-20

[0120]

[0121] After nitrogen substitution in a three-necked reaction flask equipped with mechanical stirring, thermometer and condenser, add intermediate M20-B (10 mmol), intermediate M1-A (10 mmol) and 100 mL of toluene in sequence, heat to reflux and separate water for 0.5 h, cool to 70-80 ° C, slowly add sodium tert-butoxide (15 mmol), Pd2(dba)3 (0.05 mmol), s-phos (0.1 mmol), and heat to 100-110 ° C for reaction for 3 h after the system is stable. Cool to 25-30°C, add 100 mL of water and 100 mL of toluene, stir and separate the liquids, extract the aqueous phase once with 100 mL of toluene, separate the liquids, 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 to 0-5°C, filter, and obtain compound M-20 with a yield of 61%.

[0122] Elemental analysis: C61H39N3O theoretical value: C, 88.27; H, 4.74; N, 5.06; O, 1.93; found value: C, 88.30; H, 4.71; N, 5.09; HRMS (ESI) m / z [M+H] +: theoretical value: 829.31; found value: 830.30.

[0123] Example 5

[0124] Synthesis route of M-24

[0125]

[0126] After nitrogen substitution in a three-necked reaction flask equipped with a mechanical stirrer, a thermometer and a condenser, intermediate M24-B (10 mmol), intermediate M1-A (10 mmol) and 100 mL of toluene were added in sequence, heated to reflux to separate water for 0.5 h, cooled to 70-80 °C, sodium tert-butoxide (15 mmol), Pd2(dba)3 (0.05 mmol) and s-phos (0.1 mmol) were slowly added, and after the system was stabilized, it was heated to 100-110 °C and reacted for 3 h. Cool to 25-30°C, add 100 mL of water and 100 mL of toluene, stir and separate the liquids, extract the aqueous phase once with 100 mL of toluene, separate the liquids, 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 to 0-5°C, filter, and obtain compound M-24 with a yield of 63%.

[0127] Elemental analysis: C53H29D6N3O theoretical value: C, 86.50; H, 5.61; N, 5.71; O, 2.17; found value: C, 86.56; H, 5.57; N, 5.70; HRMS (ESI) m / z [M+H] +: theoretical value: 785.33; found value: 786.33.

[0128] Example 6

[0129] Synthesis route of M-39

[0130]

[0131] After nitrogen substitution in a three-necked reaction flask equipped with a mechanical stirrer, a thermometer and a condenser, intermediate M39-B (10 mmol), intermediate M37-A (10 mmol) and 100 mL of toluene were added in sequence, heated to reflux to separate water for 0.5 h, cooled to 70-80 °C, sodium tert-butoxide (15 mmol), Pd2(dba)3 (0.05 mmol) and s-phos (0.1 mmol) were slowly added, and after the system was stabilized, it was heated to 100-110 °C and reacted for 3 h. Cool to 25-30°C, add 100 mL of water and 100 mL of toluene, stir and separate the liquids, extract the aqueous phase once with 100 mL of toluene, separate the liquids, 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 to 0-5°C, filter, and obtain compound M-39 with a yield of 54%.

[0132] Elemental analysis: C51H32N2O2 theoretical value: C, 86.91; H, 4.58; N, 3.97; O, 4.54; found value: C, 86.95; H, 4.56; N, 3.98; HRMS (ESI) m / z [M+H] +: theoretical value: 704.25; found value: 705.24.

[0133] Example 7

[0134] Synthesis route of M-52

[0135]

[0136] After nitrogen substitution in a three-necked reaction flask equipped with a mechanical stirrer, a thermometer and a condenser, intermediate M52-B (10 mmol), intermediate M2-A (10 mmol) and 100 mL of toluene were added in sequence, heated to reflux to remove water for 0.5 h, cooled to 70-80 °C, sodium tert-butoxide (15 mmol), Pd2(dba)3 (0.05 mmol) and s-phos (0.1 mmol) were slowly added, and after the system was stabilized, it was heated to 100-110 °C and reacted for 3 h. Cool to 25-30°C, add 100 mL of water and 100 mL of toluene, stir and separate the liquids, extract the aqueous phase once with 100 mL of toluene, separate the liquids, 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 to 0-5°C, filter to obtain compound M-52 with a yield of 48%.

[0137] Elemental analysis: C64H38N2O3 theoretical value: C, 86.35; H, 4.78; N, 6.43; O, 2.45; found value: C, 86.39; H, 4.75; N, 6.41; HRMS (ESI) m / z [M+H] +: theoretical value: 882.29; found value: 883.29.

[0138] Example 8

[0139] Synthesis route of M-69

[0140]

[0141] After nitrogen substitution in a three-necked reaction flask equipped with mechanical stirring, thermometer and condenser, add intermediate M69-B (10 mmol), intermediate M6-A (10 mmol) and 100 mL of toluene in sequence, heat to reflux to separate water for 0.5 h, cool to 70-80 °C, slowly add sodium tert-butoxide (15 mmol), Pd2(dba)3 (0.05 mmol) and s-phos (0.1 mmol), and after the system is stable, heat to 100-110 °C and react for 3 h. Cool to 25-30°C, add 100 mL of water and 100 mL of toluene, stir and separate the liquids, extract the aqueous phase once with 100 mL of toluene, separate the liquids, 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 to 0-5°C, filter, and obtain compound M-69 with a yield of 43%.

[0142] Elemental analysis: C51H26D6N2O2 theoretical value: C, 86.17; H, 5.39; N, 3.94; O, 4.50; found value: C, 86.21; H, 5.36; N, 3.92; HRMS (ESI) m / z [M+H] +: theoretical value: 710.28; found value: 710.38.

[0143] Example 9

[0144] Synthesis route of M-90

[0145]

[0146] After nitrogen substitution in a three-necked reaction flask equipped with a mechanical stirrer, a thermometer and a condenser, intermediate M90-B (10 mmol), intermediate M2-A (10 mmol) and 100 mL of toluene were added in sequence, heated to reflux to separate water for 0.5 h, cooled to 70-80 °C, sodium tert-butoxide (15 mmol), Pd2(dba)3 (0.05 mmol) and s-phos (0.1 mmol) were slowly added, and after the system was stabilized, it was heated to 100-110 °C and reacted for 3 h. Cool to 25-30°C, add 100 mL of water and 100 mL of toluene, stir and separate the liquids, extract the aqueous phase once with 100 mL of toluene, separate the liquids, 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 to 0-5°C, filter to obtain compound M-90 with a yield of 38%.

[0147] Elemental analysis: C63H39N3O theoretical value: C, 88.60; H, 4.60; N, 4.92; O, 1.87; found value: C, 88.65; H, 4.57; N, 4.93; HRMS (ESI) m / z [M+H] +: theoretical value: 853.31; found value: 854.29.

[0148] Example 10

[0149] Synthesis route of M-109

[0150]

[0151] After nitrogen substitution in a three-necked reaction flask equipped with a mechanical stirrer, a thermometer and a condenser, intermediate M109-B (10 mmol), intermediate M7-A (10 mmol) and 100 mL of toluene were added in sequence, heated to reflux to separate water for 0.5 h, cooled to 70-80 °C, sodium tert-butoxide (15 mmol), Pd2(dba)3 (0.05 mmol) and s-phos (0.1 mmol) were slowly added, and after the system was stabilized, it was heated to 100-110 °C and reacted for 3 h. Cool to 25-30°C, add 100 mL of water and 100 mL of toluene, stir and separate the liquids, extract the aqueous phase once with 100 mL of toluene, separate the liquids, 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 to 0-5°C, filter, and obtain compound M-109 with a yield of 60%.

[0152] Elemental analysis: C51H34N2O theoretical value: C, 88.67; H, 4.96; N, 4.06; O, 2.32; found value: C, 88.69; H, 4.95; N, 4.04; HRMS (ESI) m / z [M+H] +: theoretical value: 690.27; found value: 691.25

[0153] Embodiment 11

[0154] Synthesis route of M-120

[0155]

[0156] After nitrogen substitution in a three-necked reaction flask equipped with a mechanical stirrer, a thermometer and a condenser, intermediate M120-B (10 mmol), intermediate M7-A (10 mmol) and 100 mL of toluene were added in sequence, heated to reflux to separate water for 0.5 h, cooled to 70-80 °C, sodium tert-butoxide (15 mmol), Pd2(dba)3 (0.05 mmol) and s-phos (0.1 mmol) were slowly added, and after the system was stabilized, it was heated to 100-110 °C and reacted for 3 h. The temperature was lowered to 25-30°C, 100 mL of water and 100 mL of toluene were added, and the mixture was stirred and separated. The aqueous phase was extracted once with 100 mL of toluene, and the mixture was separated. The organic phases were combined, 7 g of anhydrous sodium sulfate was added to the organic phase, and the mixture was stirred and dried. The organic phase was filtered and concentrated (-0.08-0.09 MPa, 55-60°C) until no liquid flowed out. 20 mL of petroleum ether was added with stirring, the temperature was lowered to 0-5°C, and the mixture was filtered to obtain compound M-120 with a yield of 56%.

[0157] Elemental analysis: C57H37N3O theoretical value: C, 87.78; H, 4.78; N, 5.39; O, 2.05; found value: C, 87.84; H, 4.74; N, 5.37; HRMS (ESI) m / z [M+H] +: theoretical value: 779.29; found value: 780.28

[0158] Example 12

[0159] Synthesis route of M-148

[0160]

[0161] After nitrogen substitution in a three-necked reaction flask equipped with mechanical stirring, thermometer and condenser, intermediate M148-B (10 mmol), intermediate M8-A (10 mmol) and 100 mL of toluene were added in sequence, heated to reflux to remove water for 0.5 h, cooled to 70-80 °C, sodium tert-butoxide (15 mmol), Pd2(dba)3 (0.05 mmol) and s-phos (0.1 mmol) were slowly added, and after the system was stabilized, it was heated to 100-110 °C and reacted for 3 h. Cool to 25-30°C, add 100 mL of water and 100 mL of toluene, stir and separate the liquids, extract the aqueous phase once with 100 mL of toluene, separate the liquids, 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 to 0-5°C, filter, and obtain compound M-148 with a yield of 44%.

[0162] Elemental analysis: C53H34N2O theoretical value: C, 89.05; H, 4.79; N, 3.92; O, 2.24; found value: C, 89.08; H, 4.78; N, 3.90; HRMS (ESI) m / z [M+H] +: theoretical value: 714.27; found value: 715.26

[0163] Example 13

[0164] Synthesis route of M-178

[0165]

[0166] After nitrogen substitution in a three-necked reaction flask equipped with mechanical stirring, thermometer and condenser, intermediate M178-B (10 mmol), intermediate M18-A (10 mmol) and 100 mL of toluene were added in sequence, heated to reflux to separate water for 0.5 h, cooled to 70-80 °C, sodium tert-butoxide (15 mmol), Pd2(dba)3 (0.05 mmol) and s-phos (0.1 mmol) were slowly added, and after the system was stabilized, it was heated to 100-110 °C and reacted for 3 h. Cool to 25-30°C, add 100 mL of water and 100 mL of toluene, stir and separate the liquids, extract the aqueous phase once with 100 mL of toluene, separate the liquids, 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 to 0-5°C, filter, and obtain compound M-178 with a yield of 68%.

[0167] Elemental analysis: C45H30N2O theoretical value: C, 87.92; H, 4.92; N, 4.56; O, 2.60; found value: C, 87.97; H, 4.90; N, 4.53; HRMS (ESI) m / z [M+H] +: theoretical value: 614.24; found value: 615.25

[0168] Embodiment 14

[0169] Synthesis route of M-255

[0170]

[0171] After nitrogen substitution in a three-necked reaction flask equipped with a mechanical stirrer, a thermometer and a condenser, intermediate M255-B (10 mmol), intermediate M14-A (10 mmol) and 100 mL of toluene were added in sequence, heated to reflux to separate water for 0.5 h, cooled to 70-80 °C, sodium tert-butoxide (15 mmol), Pd2(dba)3 (0.05 mmol) and s-phos (0.1 mmol) were slowly added, and after the system was stabilized, it was heated to 100-110 °C and reacted for 3 h. Cool to 25-30°C, add 100 mL of water and 100 mL of toluene, stir and separate the liquids, extract the aqueous phase once with 100 mL of toluene, separate the liquids, 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 to 0-5°C, filter, and obtain compound M-255 with a yield of 60%.

[0172] Elemental analysis: C54H36N2OS theoretical value: C, 85.23; H, 4.77; N, 3.68; O, 2.10; S, 4.21; found value: C, 85.20; H, 4.78; N, 3.71; S, 4.19; HRMS (ESI) m / z [M+H] +: theoretical value: 760.25; found value: 761.25

[0173] Embodiment 15

[0174] M-276 Synthesis Route

[0175]

[0176] After nitrogen substitution in a three-necked reaction flask equipped with a mechanical stirrer, a thermometer and a condenser, intermediate M276-B (10 mmol), intermediate M15-A (10 mmol) and 100 mL of toluene were added in sequence, heated to reflux to separate water for 0.5 h, cooled to 70-80 °C, sodium tert-butoxide (15 mmol), Pd2(dba)3 (0.05 mmol) and s-phos (0.1 mmol) were slowly added, and after the system was stabilized, it was heated to 100-110 °C and reacted for 3 h. Cool to 25-30°C, add 100 mL of water and 100 mL of toluene, stir and separate the liquids, extract the aqueous phase once with 100 mL of toluene, separate the liquids, 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 to 0-5°C, filter, and obtain compound M-276 with a yield of 65%.

[0177] Elemental analysis: C51H32N2O2 theoretical value: C, 86.91; H, 4.58; N, 3.97; O, 4.54; found value: C, 86.96; H, 4.55; N, 3.96; HRMS (ESI) m / z [M+H] +: theoretical value: 691.24; found value: 692.23

[0178] Example 16

[0179] M-290 Synthesis Route

[0180]

[0181] After nitrogen substitution in a three-necked reaction flask equipped with a mechanical stirrer, a thermometer and a condenser, intermediate M290-B (10 mmol), intermediate M15-A (10 mmol) and 100 mL of toluene were added in sequence, heated to reflux to remove water for 0.5 h, cooled to 70-80 °C, sodium tert-butoxide (15 mmol), Pd2(dba)3 (0.05 mmol) and s-phos (0.1 mmol) were slowly added, and after the system was stabilized, it was heated to 100-110 °C and reacted for 3 h. The temperature was lowered to 25-30°C, 100 mL of water and 100 mL of toluene were added, and the mixture was stirred and separated. The aqueous phase was extracted once with 100 mL of toluene, and the mixture was separated. The organic phases were combined, 7 g of anhydrous sodium sulfate was added to the organic phase, and the mixture was stirred and dried. The organic phase was filtered and concentrated (-0.08-0.09 MPa, 55-60°C) until no liquid flowed out. 20 mL of petroleum ether was added with stirring, the temperature was lowered to 0-5°C, and the mixture was filtered to obtain compound M-290 with a yield of 58%.

[0182] Elemental analysis: C63H41N3O2 theoretical value: C, 86.77; H, 4.74; N, 4.82; O, 3.67; found value: C, 86.82; H, 4.71; N, 4.83; HRMS (ESI) m / z [M+H] +: theoretical value: 871.32; found value: 872.32

[0183] Embodiment 17

[0184] M-442 Synthesis Route

[0185]

[0186] After nitrogen substitution in a three-necked reaction flask equipped with a mechanical stirrer, a thermometer and a condenser, intermediate M442-B (10 mmol), intermediate M28-A (10 mmol) and 100 mL of toluene were added in sequence, heated to reflux to remove water for 0.5 h, cooled to 70-80 °C, sodium tert-butoxide (15 mmol), Pd2(dba)3 (0.05 mmol) and s-phos (0.1 mmol) were slowly added, and after the system was stabilized, it was heated to 100-110 °C and reacted for 3 h. The temperature was lowered to 25-30°C, 100 mL of water and 100 mL of toluene were added, and the mixture was stirred and separated. The aqueous phase was extracted once with 100 mL of toluene, and the mixture was separated. The organic phases were combined, 7 g of anhydrous sodium sulfate was added to the organic phase, and the mixture was stirred and dried. The organic phase was filtered and concentrated (-0.08-0.09 MPa, 55-60°C) until no liquid flowed out. 20 mL of petroleum ether was added with stirring, the temperature was lowered to 0-5°C, and the mixture was filtered to obtain compound M-442 with a yield of 46%.

[0187] Elemental analysis: C57H37N3O2 theoretical value: C, 86.01; H, 4.69; N, 5.28; O, 4.02; found value: C, 86.06; H, 4.65; N, 5.24; HRMS (ESI) m / z [M+H] +: theoretical value: 795.29; found value: 796.29

[0188] Application Example 1-10 and Comparative Application Example 1-2

[0189] The following application examples 1-10 and comparative application examples 1-2 provide different OLEDs, such as Figure 1 As shown, they all have the following layer structure: substrate 1 (coated glass substrate with indium tin oxide (ITO) as anode 2) / hole injection layer 3 (HIL) / hole transport layer 4 (HTL) / light-emitting layer 5 (EML) / electron transport layer 6 (ETL) / electron injection layer 7 (EIL), and finally cathode 8.

[0190] The materials used are as follows, where REF-1 and REF-2 are comparative compounds:

[0191]

[0192] The preparation of the organic electroluminescent devices of Examples 1-5 and Comparative Examples 1-3 includes the following steps:

[0193] (1) Substrate cleaning: The glass substrate coated with transparent ITO is ultrasonically treated in an aqueous cleaning agent (the composition and concentration of the aqueous cleaning agent: ethylene glycol solvent ≤ 10wt%, triethanolamine ≤ 1wt%), rinsed in deionized water, ultrasonically degreased in an acetone: ethanol mixed solvent (volume ratio 1:1), baked in a clean environment until the water is completely removed, and then cleaned with ultraviolet light and ozone.

[0194] (2) Evaporation of organic light-emitting functional layer:

[0195] The glass substrate with the anode layer is placed in a vacuum chamber and evacuated to 1×10 -6 Up to 2×10 -4 Pa, vacuum evaporating a mixture of HATCN and HT on the above anode layer film, wherein the mass ratio of HATCN to HT is 3:97, as a hole injection layer, and the evaporation thickness is 10 nm;

[0196] A hole transport layer (materials are shown in Table 1) is evaporated on the hole injection layer, and the thickness of the evaporated film is 80 nm;

[0197] The light-emitting layer is deposited on the hole transport layer. The specific preparation method is: vacuum-deposit the light-emitting host material (CBP) and the guest material (piq)2Ir(acac) in a co-evaporation manner, and the total film thickness of the deposition is 30 nm;

[0198] An electron transport layer is evaporated on the light-emitting layer. The specific preparation method is as follows: vacuum evaporation of electron transport material (ET and LiQ mass ratio is 1) in a co-evaporation manner, and the total evaporation film thickness is 30nm;

[0199] An electron injection layer (made of LiQ) is vacuum-deposited on the electron transport layer, with a total film thickness of 1 nm.

[0200] Al was evaporated on the electron injection layer, and the total film thickness of the evaporated layer was 90 nm.

[0201] The parameters of each layer in the device, its material, thickness, etc. are shown in Table 1 below:

[0202] Table 1

[0203]

[0204]

[0205] Performance Test:

[0206] Test sample: organic electroluminescent device provided in Application Examples 1-5 and Comparative Application Examples 1-3;

[0207] Test instruments: The device's current, voltage, brightness, luminous spectrum and other characteristics are tested synchronously using a PR 650 spectrum scanning luminance meter and a Keithley K 2400 digital source meter system;

[0208] Test conditions: Photoelectric properties Test conditions: Current density is 10mA / cm 2 ;

[0209] Life test: current density is 50mA / cm 2 , record the time (in hours) when the device brightness drops to 95% of the original brightness;

[0210] The test results are shown in Table 2.

[0211] Table 2

[0212] project Driving voltage(V) Current efficiency (Cd / A) Lifespan T95(hrs) Application Example 1 4.53 15.31 105.4 Application Example 2 4.32 16.54 118.7 Application Example 3 4.42 15.89 110.2 Application Example 4 4.37 15.23 115.1 Application Example 5 4.40 15.96 113.2 Comparative Example 1 5.34 11.09 64.0 Comparative Example 2 4.74 15.20 89.8 Comparative Example 3 4.85 13.68 85.5

[0213] According to the above device performance test, compared with the comparative compounds REF-1 and REF-2, the device in which the compound of the present invention is used as a hole transport material exhibits a reduced driving voltage (as low as below 4.53V) and a higher current efficiency (above 15Cd / A), and has a longer life (above 100h).

[0214] The preparation of the organic electroluminescent devices of Application Examples 6-22 and Comparative Examples 4-8 includes the following steps:

[0215] (1) Substrate cleaning: The glass substrate coated with transparent ITO is ultrasonically treated in an aqueous cleaning agent (the composition and concentration of the aqueous cleaning agent: ethylene glycol solvent ≤ 10wt%, triethanolamine ≤ 1wt%), rinsed in deionized water, ultrasonically degreased in an acetone: ethanol mixed solvent (volume ratio 1:1), baked in a clean environment until the water is completely removed, and then cleaned with ultraviolet light and ozone.

[0216] (2) Evaporation of organic light-emitting functional layer:

[0217] The glass substrate with the anode layer is placed in a vacuum chamber and evacuated to 1×10 -6 Up to 2×10 -4 Pa, vacuum evaporating a mixture of HATCN and HT on the above anode layer film, wherein the mass ratio of HATCN to HT is 3:97, as a hole injection layer, and the evaporation thickness is 10 nm;

[0218] A hole transport layer (HT) is evaporated on the hole injection layer, and the thickness of the evaporated film is 80 nm;

[0219] The light-emitting layer is deposited on the hole transport layer. The specific preparation method is as follows: vacuum-deposit the light-emitting host material (the materials are shown in Table 3) and the guest material (piq)2Ir(acac) in a co-evaporation manner, and the total film thickness of the deposition is 30 nm;

[0220] An electron transport layer is evaporated on the light-emitting layer. The specific preparation method is as follows: vacuum evaporation of electron transport material (ET and LiQ mass ratio is 1) in a co-evaporation manner, and the total evaporation film thickness is 30nm;

[0221] An electron injection layer (made of LiQ) is vacuum-deposited on the electron transport layer, with a total film thickness of 1 nm.

[0222] Al was evaporated on the electron injection layer, and the total film thickness of the evaporated layer was 90 nm.

[0223] The parameters of each layer in the device, its material, thickness, etc. are shown in the following 3:

[0224] Table 3

[0225]

[0226]

[0227]

[0228]

[0229]

[0230] Device performance test:

[0231] Test sample: organic electroluminescent devices provided in Application Examples 6-22 and Comparative Examples 4-8;

[0232] Test instruments: The device's current, voltage, brightness, luminous spectrum and other characteristics are tested synchronously using a PR 650 spectrum scanning luminance meter and a Keithley K 2400 digital source meter system;

[0233] Test conditions: Photoelectric properties Test conditions: Current density is 10mA / cm 2 ;

[0234] Life test: current density is 50mA / cm 2 , record the time (in hours) when the device brightness drops to 95% of the original brightness;

[0235] The test results are shown in Table 4 below:

[0236] Table 4

[0237]

[0238]

[0239] The results shown in Table 4 prove that the device using the organic compound of the present invention is improved in voltage, life and luminous efficiency compared with the comparative compound REF-1 and the comparative compound REF-2. The driving voltage of the device is as low as 3.4V or less, the current efficiency is as high as 22Cd / A or more, and the life is as long as 310h or more.

[0240] The introduction of naphthyl groups in the compounds of the present invention can adjust the energy level and change the molecular configuration. The structural characteristics of the organic compounds of the present invention are conducive to improving the glass transition temperature of the molecules and at the same time are conducive to reducing the evaporation temperature of the molecules. That is to say, even if the molecular weight of the structure is relatively high, it can ensure a lower evaporation temperature. This excellent performance is not only conducive to the thermal evaporation of materials, but also controls the thermal decomposition rate of materials, thereby improving the stability of materials in device applications.

[0241] It can be seen from Tables 1-4 that the organic material provided in the embodiments of the present invention can match the corresponding light-emitting layer and has a certain hole transport capacity. At the same time, the evaporation temperature of the material is correspondingly reduced during device preparation, which is beneficial to the preparation of the device.

[0242] As a luminescent material, this material is combined with compounds with electron transport properties to work synergistically with each other in the luminescent layer, effectively reducing the driving voltage and current working efficiency of the device and extending the device life, achieving significant progress in the application of main materials.

[0243] In summary, the organic compound provided by the present invention has HOMO, LUMO and ET1 values ​​that are close to each other, which can reduce the driving voltage of the device, improve the luminous efficiency of the device and extend the service life of the device.

[0244] The applicant declares that the present invention illustrates the process method of the present invention through the above-mentioned embodiments, but the present invention is not limited to the above-mentioned process steps, that is, it does not mean that the present invention must rely on the above-mentioned process steps to be implemented. Those skilled in the art should understand that any improvement of the present invention, equivalent replacement of the raw materials selected by the present invention, addition of auxiliary components, selection of specific methods, etc., all fall within the protection scope and disclosure scope of the present invention.

Claims

1. An organic compound, characterized in that The organic compound has a structure shown in Formula I: X is selected from O or S, L is selected from naphthylene, L 1 , L 2 is selected from a connecting bond, a substituted or unsubstituted C6-C30 arylene group, a substituted or unsubstituted C3-C30 heteroarylene group, Ar 1 -Ar 3 are each independently selected from hydrogen, deuterium, protium, halogen, cyano, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C6-C60 arylamine, substituted or unsubstituted C3-C60 heteroarylamine and substituted or unsubstituted C3-C60 heteroaryl, The substituents of the substituted C6-C30 arylene group, C3-C30 heteroarylene group, substituted C6-C30 aryl group, substituted C3-C30 heteroaryl group, substituted C6-C60 aromatic amine group and substituted C3-C60 heteroaromatic amine 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 heteroaromatic group, C6-C60 aromatic amine group and C3-C60 heteroaromatic amine group.

2. The organic compound according to claim 1, characterized in that Ar1 and Ar2 are each independently selected from hydrogen, deuterium, halogen, substituted or unsubstituted phenyl, naphthyl, biphenyl, phenanthrenyl, fluoranthenyl, yl, terphenyl, triphenylene, phenylnaphthyl, naphthylphenyl, dimethylfluorenyl, phenylmethylfluorenyl, diphenylfluorenyl, carbazolyl, benzocarbazolyl, phenylcarbazolyl, phenylbenzocarbazolyl, phenylphenanthrocarbazolyl, 9-phenyl-9H-dibenzo[a,c]carbazolyl, spiro[fluorene-9,9'-xanthene]yl, pyridyl, pyridylphenyl, phenylpyridyl, spirobifluorenyl, benzodimethylfluorenyl, benzodiphenylfluorenyl, benzospirobifluorenyl, dibenzo furanyl, benzonaphthofuranyl, benzonaphthothiophenyl, dibenzothiophenyl, diphenylamine, diphenylamine, N-phenyl-benzidine and N-phenyl-dibenzofuranamine; the substituents are each independently selected from one or a combination of at least two of deuterium, halogen, cyano, C1-C6 alkyl, C3-C12 cycloalkyl, C6-C25 aryl, C3-C25 heteroaryl, C6-C60 aromatic amine, C3-C60 heteroaromatic amine.

3. The organic compound according to claim 1 or 2, characterized in that L 1 and L 2 Each is independently selected from a linker, a phenylene group or a naphthylene group.

4. The organic compound according to any one of claims 1 to 3, characterized in that Ar 1 and Ar 2 Each independently selected from phenyl, fluorophenyl, cyano-substituted phenyl, naphthyl, phenanthryl, biphenyl, phenyl, terphenyl, phenylnaphthyl, naphthylphenyl, dimethylfluorenyl, diphenylfluorenyl, phenylbenzocarbazolyl, phenylphenanthrocarbazolyl, spiro[fluorene-9,9'-xanthene]yl, spirobifluorenyl, phenylmethylfluorenyl, dibenzofuranyl, benzonaphthofuranyl, diphenylamino, N-phenyl-benzidine or The wavy line represents the attachment site of the group, and D represents deuterium; Preferably, Ar 3 Selected from phenyl or naphthyl.

5. The organic compound according to any one of claims 1 to 4, characterized in that Ar 1 and Ar 2 Each is independently selected from any one of the following groups: Indicates a connection key.

6. The organic compound according to any one of claims 1 to 5, characterized in that The organic compound is any one of M-1 to M-764: Where D stands for deuterium.

7. An organic electroluminescent material, characterized in that: The organic electroluminescent material comprises the organic compound according to any one of claims 1 to 6.

8. 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 the organic compound according to any one of claims 1 to 6 or the organic electroluminescent material according to claim 7.

9. The organic electroluminescent device according to claim 8, characterized in that: The organic layer comprises a hole transport layer, and the hole transport layer comprises the organic compound according to any one of claims 1 to 6 or the organic electroluminescent material according to claim 7; Preferably, the organic layer comprises a light-emitting layer, and the light-emitting layer comprises the organic compound according to any one of claims 1 to 6 or the organic electroluminescent material according to claim 7; Preferably, the organic layer further comprises one or a combination of at least two of a hole injection layer, a light emitting layer, an electron transport layer, an electron blocking layer, an electron buffer layer or an electron injection layer.

10. Use of the organic electroluminescent device according to claim 8 or 9 in optical fiber equipment, lighting equipment, electrophotographic photoreceptor equipment, photoelectric converter, organic solar cell, switching element equipment, organic light-emitting field effect transistor, image sensor or dye laser.

Images