Organic compound and application thereof

Abstract

The invention provides an organic compound and application thereof, the organic compound has a structure as shown in formula I. The structure of the organic compound is beneficial to increasing the glass transition temperature of molecules and reducing the evaporation temperature of the molecules, that is to say, even if the molecular weight of the structure is relatively high, the evaporation temperature of the molecules is reduced. However, the low evaporation temperature can be ensured, the excellent performance is beneficial to thermal evaporation of the material, the thermal decomposition rate of the material is controlled, and therefore the stability of the material in device application is improved. The organic compound can reduce the driving voltage of a device, improve the luminous efficiency of the device and prolong the service life of the device.

Description

Technical Field

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

[0002] An organic electroluminescent device (OLED) converts electrical energy into light by applying electricity to an organic electroluminescent material, and generally includes 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 light-emitting auxiliary layer, an electron blocking layer, a light-emitting layer (containing a host material and a dopant material), an electron buffer layer, a hole blocking layer, an electron transport layer, an electron injection layer, etc. Various materials used in the organic layer are classified into a hole injection material, a hole transport material, a hole auxiliary material, a light-emitting auxiliary material, an electron blocking material, a light-emitting material, an electron buffer material, a hole blocking material, an electron transport material, an electron injection material, etc. based on the functions achieved by each layer. In the organic electroluminescent device, holes from the anode and electrons from the cathode are injected into the light-emitting layer by applying a voltage, and excitons with high energy are generated by the recombination of holes and electrons. The organic light-emitting compound emits light by the energy moving to the excited state and the energy when the organic light-emitting compound returns from the excited state to the ground state.

[0003] With the large area of the display, the driving voltage also increases, and problems such as low luminous efficiency and short lifespan also appear, severely restricting the application of organic electroluminescent devices. Therefore, organic materials must solve these efficiency or lifespan problems, and new materials with high efficiency, long lifespan, and suitable for mass production for organic light-emitting devices need to be continuously developed. Summary of the Invention

[0004] Aiming at the deficiencies of the prior art, the purpose of the present invention is to provide an organic compound and its application.

[0005] To achieve the purpose of this invention, the present invention adopts the following technical solutions:

[0006] On the one hand, the present invention provides an organic compound having the structure shown in Formula I:

[0007]

[0008] X is selected from O or S,

[0009] L, L 1 and L 2 are each independently selected from a linking bond, a substituted or unsubstituted C6-C30 arylene group, a substituted or unsubstituted C3-C30 heteroarylene group,

[0010] Ar is selected from substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C6-C60 arylamino, substituted or unsubstituted C3-C60 heteroarylamino, and substituted or unsubstituted C3-C60 heteroaryl,

[0011] Ar 1 is selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C6-C60 arylamino, substituted or unsubstituted C3-C60 heteroarylamino, and substituted or unsubstituted C3-C60 heteroaryl,

[0012] Ar 2 is selected from substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C6-C60 arylamino, substituted or unsubstituted C3-C60 heteroarylamino, and substituted or unsubstituted C3-C60 heteroaryl,

[0013] wherein, Ar 1 is not any one of the following substituted or unsubstituted benzocarbazolyl groups:

[0014] The wavy line represents the connection site of the group;

[0015] The substituents in the substituted C6-C30 arylene, C3-C30 heteroarylene, substituted C6-C30 aryl, substituted C3-C30 heteroaryl, substituted C6-C60 arylamino, and substituted C3-C60 heteroarylamino are each independently selected from deuterium, halogen, cyano, C1-C12 alkyl, C3-C12 cycloalkyl, C6-C30 aryl, C3-C30 heteroaryl, C6-C60 arylamino, and C3-C60 heteroarylamino, or a combination of one or at least two of them.

[0016] Preferably, Ar 1 is selected from hydrogen, deuterium, halogen, and the following substituted or unsubstituted groups: phenyl, naphthyl, biphenyl, phenanthryl, fluoranthenyl, anthryl, terphenyl, triphenylene, phenylnaphthyl, naphthylphenyl, carbazolyl, phenylcarbazolyl, dimethylfluorenyl, phenylmethylfluorenyl, diphenylfluorenyl, pyridyl, pyridylphenyl, phenylpyridyl, spirobifluorenyl, benzodimethylfluorenyl, benzodiphenylfluorenyl, benzospirobifluorenyl, dibenzofuranyl, benzonaphthofuranyl, benzonaphthothiophenyl, spiro[fluorene-9,9'-xanthene]yl, phenylmethylfluorenyl, dinaphthofuranyl, dinaphthothiophenyl, dibenzothiophenyl, or C6-C30 arylamino;

[0017] Preferably, the C6-C30 arylamino is selected from diphenylamino, di(4-biphenylyl)amino, N-phenyl-biphenylamine, or N-phenyl-dibenzofuranamine.

[0018] Preferably, the C6-C30 arylamino group is a diphenylamino group.

[0019] Preferably, Ar 2 is selected from the following substituted or unsubstituted groups: phenyl, naphthyl, biphenyl, phenanthryl, fluoranthenyl, anthryl, terphenyl, triphenylene, phenylnaphthyl, naphthylphenyl, carbazolyl, benzocarbazolyl, dimethylfluorenyl, phenylmethylfluorenyl, diphenylfluorenyl, pyridyl, pyridylphenyl, phenylpyridyl, spirobifluorenyl, benzodimethylfluorenyl, benzodiphenylfluorenyl, benzospirobifluorenyl, dibenzofuranyl, benzonaphthofuranyl, benzonaphthothiophenyl, spiro[fluorene-9,9'-xanthene]yl, phenylmethylfluorenyl, dinaphthofuranyl, dinaphthothiophenyl, dibenzothiophenyl,

[0020] The substituents are each independently selected from one or a combination of at least two of C1-C6 alkyl, C3-C12 cycloalkyl, C6-C25 aryl, C3-C25 heteroaryl, C6-C60 arylamino, and C3-C60 heteroarylamino.

[0021] Preferably, L, L 1 and L 2 are each independently selected from a linking bond, a substituted or unsubstituted C6-C30 arylene;

[0022] Preferably, L, L 1 and L 2 are each independently selected from a linking bond, phenylene, biphenylene or naphthylene;

[0023] Preferably, Ar 1 and Ar 2 are each independently selected from phenyl, naphthyl, biphenyl, phenanthryl, anthryl, terphenyl, triphenylene, fluoranthenyl, phenylnaphthyl, naphthylphenyl, carbazolyl, dimethylfluorenyl, diphenylfluorenyl, phenylcarbazolyl, phenylphenanthrocarbazolyl, spirobifluorenyl, spiro[fluorene-9,9'-xanthene]yl, phenylmethylfluorenyl, dibenzofuranyl, benzonaphthofuranyl or diphenylamino.

[0024] Preferably, Ar is selected from phenyl or naphthyl, and more preferably, Ar is phenyl.

[0025] Preferably, the organic compound is selected from any one of the following M-1 to M-250:

[0026]

[0027]

[0028]

[0029]

[0030]

[0031]

[0032]

[0033]

[0034]

[0035]

[0036] Definition of Substituent Terms

[0037] As used in the present invention, the term "halogen" may include fluorine, chlorine, bromine, or iodine.

[0038] As used in the present invention, the term "C1-C30 alkyl" refers to a monovalent substituent derived from a straight-chain or branched-chain saturated hydrocarbon having 1 to 30 carbon atoms, and examples thereof include, but are not limited to, methyl, ethyl, propyl, isobutyl, sec-butyl, tert-butyl, pentyl, isopentyl, and hexyl.

[0039] As used in the present invention, the term "C3-C30 cycloalkyl" refers to a monocyclic hydrocarbon or polycyclic hydrocarbon derived from a ring main chain having 1 to 30 carbon atoms, and the cycloalkane may include cyclopropyl, cyclobutyl, adamantyl, and the like.

[0040] In the present invention, aryl and arylene include monocyclic, polycyclic, or fused-ring aryl, the rings of which may be interrupted by short non-aromatic units and may include a spiro structure, including but not limited to phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, anthryl, fluorenyl, spirobifluorenyl, and the like.

[0041] In the present invention, heteroaryl and heteroarylene include monocyclic, polycyclic, or fused-ring heteroaryl, the rings of which may be interrupted by short non-aromatic units, and the heteroatoms include nitrogen, oxygen, and sulfur. Including but not limited to furyl, phenylthio, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetrazinyl, triazolyl, tetrazolyl, furazanyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, benzofuryl, benzothienyl, isobenzofuryl, dibenzofuryl, dibenzothienyl, benzimidazolyl, benzothiazolyl, benzoisothiazolyl, benzoisoxazolyl, benzoxazolyl, isoindolyl, indolyl, indazolyl, benzothiadiazolyl, quinolinyl, isoquinolinyl, cinnolinyl, quinazolinyl, quinoxalinyl, carbazolyl, phenoxazinyl, phenothiazinyl, phenanthridinyl, benzodioxolyl, dihydroacridinyl, and their derivatives, etc.

[0042] As used in the present invention, the term "substituted" means that a hydrogen atom in a compound is replaced by another substituent. The position is not limited to a specific position as long as the hydrogen at that position can be replaced by a substituent. When there are two or more substituents, the two or more substituents may be the same or different.

[0043] As used in the present invention, unless otherwise specified, a hydrogen atom includes protium, deuterium and tritium.

[0044] In the present invention, in the definition of a group, the range of the number of carbon atoms is defined, and the number of carbon atoms is any integer within the defined range. For example, C6-C60 aryl means that the number of carbon atoms of the aryl can be any integer within the range of 6-60, such as 6, 8, 10, 13, 15, 17, 20, 22, 25, 30, 35, 38, 40, 44, 48, 50, 55, 58 or 60, etc.

[0045] In the present invention, the organic compound shown in Formula I can be prepared by the following synthetic route:

[0046] 1. Synthesis of intermediate n-A:

[0047] The reaction raw materials Mn-A-a and Mn-A-b carry out a Suzuki cross-coupling reaction:

[0048]

[0049] 2. Synthesis of compound M:

[0050] The intermediate Mn-A and Mn-B carry out a Buchwald-Hartwig cross-coupling reaction:

[0051]

[0052] On the other hand, the present invention provides an organic electroluminescent material, and the organic electroluminescent material contains the organic compound as described above.

[0053] On the other hand, the present invention provides an organic electroluminescent device, and the organic electroluminescent device includes a cathode, an anode, and an organic layer located between the cathode and the anode, and the organic layer contains the organic compound as described above or the organic electroluminescent material as described above.

[0054] Preferably, the organic layer includes a hole transport layer, and the hole transport layer contains the organic compound as described above or the organic electroluminescent material as described above.

[0055] Preferably, the organic layer further comprises a light-emitting layer, and the light-emitting layer comprises the organic compound or the organic electroluminescent material as described above.

[0056] Preferably, the organic layer further comprises at least one of a hole injection layer, an electron transport layer, an electron blocking layer, an electron buffer layer, or an electron injection layer.

[0057] Preferably, the light-emitting layer comprises at least one of the organic compounds as described above and at least one compound represented by Formula N:

[0058]

[0059] 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,

[0060] R 1 is selected from -L 1 Ar 1 ; R 2 is selected from -L 2 Ar 2 ; R 3 is selected from -L 3 Ar 3 ; R 4 is selected from -L 4 Ar 4 ;

[0061] L 1 -L 4 each independently selected from a linking bond, substituted or unsubstituted C6-C30 arylene, substituted or unsubstituted C3-C30 heteroarylene,

[0062] Ar 1 -Ar 4 each independently selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C6-C60 arylamino, substituted or unsubstituted C3-C60 heteroarylamino, substituted or unsubstituted C6-C60 arylC3-C60 heteroarylamino, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl;

[0063] Preferably, Ar 1 -Ar 4 each independently selected from substituted or unsubstituted groups such as hydrogen, deuterium, phenyl, naphthyl, biphenyl, terphenyl, phenanthryl, fluoranthenyl, triphenylene, dimethylfluorenyl, diphenylfluorenyl, spirobifluorenyl, benzo-dimethylfluorenyl, benzo-diphenylfluorenyl, benzo-spirobifluorenyl, dibenzofuranyl or dibenzothiophenyl;

[0064] Preferably, in Formula 1, the R 1 , R 2 , R 3 , R 4 at least one is selected from hydrogen;

[0065] Preferably, the R 1 , R 2 , R 3 , R 4 at least two are selected from hydrogen;

[0066] Preferably, three of the R 1 , R 2 , R 3 , R 4 are selected from hydrogen;

[0067] Preferably, the R 2 is selected from L 2 Ar 2 , and R 1 , R 3 , R 4 are all selected from hydrogen;

[0068] Preferably, the R 3 is selected from L 3 Ar 3 , and R 1 , R 2 , R 4 are all selected from hydrogen;

[0069] Preferably, the R is selected from the following groups which are substituted or unsubstituted: phenyl, biphenyl;

[0070] Preferably, L 1 -L 4 each independently is selected from a linking bond, a substituted or unsubstituted phenylene, naphthylene or biphenylene, a substituted or unsubstituted terphenylene, a substituted or unsubstituted naphthylene.

[0071] On the other hand, the present invention provides the application of the organic electroluminescent device as described above in a fiber optic 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.

[0072] Compared with the prior art, the present invention has the following beneficial effects:

[0073] The structure of the organic compound of the present invention is conducive to increasing the glass transition temperature of the molecule and at the same time conducive to reducing the evaporation temperature of the molecule. That is to say, even if the molecular weight of the structure is relatively high, a relatively low evaporation temperature can be ensured. This excellent property is conducive to the thermal evaporation of the material and controlling the thermal decomposition rate of the material, thereby improving the stability of the material in device applications.

[0074] The organic compound of the present invention can reduce the driving voltage of the device, improve the luminous efficiency of the device and extend the service life of the device. BRIEF DESCRIPTION OF THE DRAWINGS

[0075] Figure 1 is a schematic structural diagram of the organic electroluminescent device of the present invention;

[0076] 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 OF THE INVENTION

[0077] The technical solutions of the present invention will be further described below through specific embodiments. Those skilled in the art should understand that the embodiments are only for helping to understand the present invention and should not be regarded as specific limitations on the present invention.

[0078] Synthesis Examples

[0079] All the compounds whose synthesis is not mentioned below can be obtained through commercial purchase or by operating or conditioning according to the conventional experimental procedures described in the literature in the art.

[0080] I. Synthesis of Intermediates

[0081] Synthesis of Intermediate M1-A

[0082]

[0083] After purging the three-necked reaction flask equipped with a mechanical stirrer, a thermometer and a condenser with nitrogen, M1-A-a (10 mmol), M1-A-b (10 mmol), 100 mL of toluene, 20 mL of ethanol, 20 mL of water were added in sequence, potassium carbonate (20 mmol), Pd(PPh3)4 (0.05 mmol) were added, and the mixture was heated to 70-80 °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 stirred for liquid separation. The aqueous phase was extracted once with 100 mL of toluene, and then separated. The organic phases were combined, 7 g of anhydrous sodium sulfate was added to the organic phase and stirred for drying, filtered, and the organic phase was concentrated (-0.08 to 0.09 MPa, 55 to 60 °C) until no liquid flowed out. The mixture was stirred and 50 mL of a mixed solvent of dichloromethane and petroleum ether was added, and the temperature was lowered to 0-5 °C, and then filtered to obtain Compound 1-A with a yield of 65%.

[0084] The preparation of the following intermediates 2-A to 8-A is the same as that of 1-A, except that M1-A-a substituted with borate esters at different sites and brominated and chlorinated raw materials M1-A-b at different sites are used:

[0085]

[0086] Example 1

[0087] Synthetic route of M-1

[0088]

[0089] After purging the three-necked reaction flask equipped with a mechanical stirrer, a thermometer, and a condenser with nitrogen, intermediate M1-B (10 mmol), intermediate M1-A (10 mmol), and 100 mL of toluene were successively added. The mixture was heated under reflux to separate water for 0.5 h, cooled to 70 - 80 °C, and sodium tert-butoxide (15 mmol), Pd2(dba)3 (0.05 mmol), and s-phos (0.1 mmol) were slowly added. After the system was stabilized, it was heated to 100 - 110 °C and reacted for 3 h. It was cooled 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, separated, and the organic phases were combined. 7 g of anhydrous sodium sulfate was added to the organic phase, stirred and dried, filtered, and the organic phase was concentrated (-0.08 - 0.09 MPa, 55 - 60 °C) until no liquid flowed out. 20 mL of petroleum ether was added with stirring, and the mixture was cooled to 0 - 5 °C and filtered to obtain compound M-1 with a yield of 64%.

[0090] Elemental analysis: C45H30N2O Theoretical values: C, 87.92; H, 4.92; N, 4.56; O, 2.60; Measured values: C, 87.53; H, 5.21; N, 4.66;; HRMS(ESI) m / z [M+H]+: Theoretical value: 614.24; Measured value: 615.25.

[0091] Example 2

[0092] Synthetic route of M-4

[0093]

[0094] After purging the three-necked reaction flask equipped with a mechanical stirrer, a thermometer, and a condenser with nitrogen, intermediate 4-B (10 mmol), intermediate 1-A (10 mmol), and 100 mL of toluene were successively added. The mixture was heated under reflux to separate water for 0.5 h, cooled to 70 - 80 °C, and sodium tert-butoxide (15 mmol), Pd2(dba)3 (0.05 mmol), and s-phos (0.1 mmol) were slowly added. After the system was stabilized, it was heated to 100 - 110 °C and reacted for 3 h. It was cooled 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, separated, and the organic phases were combined. 7 g of anhydrous sodium sulfate was added to the organic phase, stirred and dried, filtered, and the organic phase was concentrated (-0.08 - 0.09 MPa, 55 - 60 °C) until no liquid flowed out. 20 mL of petroleum ether was added with stirring, cooled to 0 - 5 °C, and filtered to obtain compound M-4 with a yield of 54%.

[0095] Elemental analysis: C57H39N3O Theoretical values: C, 87.55; H, 5.03; N, 5.37; O, 2.05; Measured values: C, 87.82; H, 5.13; N, 5.01; HRMS(ESI) m / z [M+H]+: Theoretical value: 781.31; Measured value: 782.30.

[0096] Example 3

[0097] Synthetic route of M-20

[0098]

[0099] After purging the three-necked reaction flask equipped with a mechanical stirrer, a thermometer, and a condenser with nitrogen, intermediate 20-B (10 mmol), intermediate 2-A (10 mmol), and 100 mL of toluene were successively added. The mixture was heated under reflux to separate water for 0.5 h, cooled to 70 - 80 °C, and sodium tert-butoxide (15 mmol), Pd2(dba)3 (0.05 mmol), and s-phos (0.1 mmol) were slowly added. After the system was stabilized, it was heated to 100 - 110 °C and reacted for 3 h. It was cooled 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, separated, and the organic phases were combined. 7 g of anhydrous sodium sulfate was added to the organic phase, stirred and dried, filtered, and the organic phase was concentrated (-0.08 - 0.09 MPa, 55 - 60 °C) until no liquid flowed out. 20 mL of petroleum ether was added with stirring, cooled to 0 - 5 °C, and filtered to obtain compound M-20 with a yield of 58%.

[0100] Elemental analysis: C51H32N2O2 Theoretical values: C, 86.91; H, 4.58; N, 3.97; O, 4.54; Measured values: C, 87.32; H, 4.18; N, 3.85; HRMS(ESI) m / z [M+H]+: Theoretical value: 704.25; Measured value: 705.25.

[0101] Example 4

[0102] Synthetic route of M-24

[0103]

[0104] After replacing the nitrogen in the three-neck reaction flask equipped with mechanical stirring, thermometer and condenser, add intermediate 24-B (10 mmol), intermediate 3-A (10 mmol), 100 mL of toluene in sequence, heat under reflux to separate water for 0.5 h, cool down 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 down to 25 - 30 °C, add 100 mL of water and 100 mL of toluene, stir and separate the liquid. Extract the aqueous phase with 100 mL of toluene once, separate the liquid, combine the organic phases, add 7 g of anhydrous sodium sulfate to the organic phases, stir and dry, filter, concentrate the organic phases (-0.08 - 0.09 MPa, 55 - 60 °C) until no liquid flows out, stir and add 20 mL of petroleum ether, cool down to 0 - 5 °C, filter to obtain compound M-24 with a yield of 58%.

[0105] Elemental analysis: C55H34N2O2 Theoretical values: C, 87.51; H, 4.54; N, 3.71; O, 4.24; Measured values: C, 87.89; H, 4.44; N, 3.43; HRMS(ESI) m / z [M+H]+: Theoretical value: 754.26; Measured value: 755.26.

[0106] Example 5

[0107] Synthetic route of M-32

[0108]

[0109] After purging the three-necked reaction flask equipped with a mechanical stirrer, a thermometer, and a condenser with nitrogen, intermediate 32-B (10 mmol), intermediate 4-A (10 mmol), and 100 mL of toluene were successively added. The mixture was heated under reflux to separate water for 0.5 h, then cooled to 70 - 80 °C, and sodium tert-butoxide (15 mmol), Pd2(dba)3 (0.05 mmol), and s-phos (0.1 mmol) were slowly added. After the system stabilized, it was heated to 100 - 110 °C and reacted for 3 h. It was cooled 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, separated, and the organic phases were combined. 7 g of anhydrous sodium sulfate was added to the organic phase, stirred and dried, filtered, and the organic phase was concentrated (-0.08 - 0.09 MPa, 55 - 60 °C) until no liquid flowed out. 20 mL of petroleum ether was added with stirring, cooled to 0 - 5 °C, and filtered to obtain compound M-32 with a yield of 58%.

[0110] Elemental analysis: C57H38N2O Theoretical values: C, 89.27; H, 4.99; N, 3.65; O, 2.09; Measured values: C, 89.83; H, 4.65; N, 3.44; HRMS(ESI) m / z [M+H]+: Theoretical value: 766.30; Measured value: 767.28.

[0111] Example 6

[0112] Synthetic route of M-51

[0113]

[0114] After purging the three-necked reaction flask equipped with a mechanical stirrer, a thermometer, and a condenser with nitrogen, intermediate 51-B (10 mmol), intermediate 5-A (10 mmol), and 100 mL of toluene were successively added. The mixture was heated under reflux to separate water for 0.5 h, then cooled to 70 - 80 °C, and sodium tert-butoxide (15 mmol), Pd2(dba)3 (0.05 mmol), and s-phos (0.1 mmol) were slowly added. After the system stabilized, it was heated to 100 - 110 °C and reacted for 3 h. It was cooled 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, separated, and the organic phases were combined. 7 g of anhydrous sodium sulfate was added to the organic phase, stirred and dried, filtered, and the organic phase was concentrated (-0.08 - 0.09 MPa, 55 - 60 °C) until no liquid flowed out. 20 mL of petroleum ether was added with stirring, cooled to 0 - 5 °C, and filtered to obtain compound M-51 with a yield of 49%.

[0115] Elemental analysis: C68H42N2O Theoretical values: C, 90.44; H, 4.69; N, 3.10; O, 1.77; Measured values: C, 90.47; H, 4.64; N, 3.13; HRMS(ESI) m / z [M+H]+: Theoretical value: 902.33; Measured value: 903.33.

[0116] Example 7

[0117] Synthetic route of M-63

[0118]

[0119] After replacing the nitrogen in a three-necked reaction flask equipped with a mechanical stirrer, a thermometer and a condenser, add intermediate 63-B (10 mmol), intermediate 6-A (10 mmol), 100 mL of toluene in sequence, heat under reflux to separate water for 0.5 h, cool down 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 down to 25 - 30 °C, add 100 mL of water and 100 mL of toluene, stir and separate the liquid. Extract the aqueous phase with 100 mL of toluene once, separate the liquid, combine the organic phases. Add 7 g of anhydrous sodium sulfate to the organic phase, stir and dry, filter. Concentrate the organic phase (-0.08 - 0.09 MPa, 55 - 60 °C) until no liquid flows out, stir and add 20 mL of petroleum ether, cool down to 0 - 5 °C, filter to obtain compound M-63, with a yield of 56%.

[0120] Elemental analysis: C51H38N2O Theoretical values: C, 88.15; H, 5.51; N, 4.03; O, 2.30; Measured values: C, 88.13; H, 5.52; N, 4.04; HRMS(ESI) m / z [M+H]+: Theoretical value: 694.30; Measured value: 695.30.

[0121] Example 8

[0122] Synthetic route of M-71

[0123]

[0124] After the three-necked reaction flask equipped with a mechanical stirrer, a thermometer, and a condenser was purged with nitrogen, intermediate 71-B (10 mmol), intermediate 6-A (10 mmol), and 100 mL of toluene were successively added. The mixture was heated under reflux to separate water for 0.5 h, then cooled to 70 - 80 °C, and sodium tert-butoxide (15 mmol), Pd2(dba)3 (0.05 mmol), and s-phos (0.1 mmol) were slowly added. After the system was stabilized, it was heated to 100 - 110 °C and reacted for 3 h. It was cooled 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, separated, and the organic phases were combined. 7 g of anhydrous sodium sulfate was added to the organic phase, stirred and dried, filtered, and the organic phase was concentrated (-0.08 - 0.09 MPa, 55 - 60 °C) until no liquid flowed out. 20 mL of petroleum ether was added with stirring, cooled to 0 - 5 °C, and filtered to obtain compound M-71 with a yield of 67%.

[0125] Elemental analysis: C45H28N2O2 Theoretical values: C, 85.97; H, 4.49; N, 4.46; O, 5.09; Measured values: C, 85.99; H, 4.46; N, 4.45; HRMS(ESI) m / z [M + H]+: Theoretical value: 628.22; Measured value: 629.22.

[0126] Example 9

[0127] Synthetic route of M-86

[0128]

[0129] After the three-necked reaction flask equipped with a mechanical stirrer, a thermometer, and a condenser was purged with nitrogen, intermediate 86-B (10 mmol), intermediate 7-A (10 mmol), and 100 mL of toluene were successively added. The mixture was heated under reflux to separate water for 0.5 h, then cooled to 70 - 80 °C, and sodium tert-butoxide (15 mmol), Pd2(dba)3 (0.05 mmol), and s-phos (0.1 mmol) were slowly added. After the system was stabilized, it was heated to 100 - 110 °C and reacted for 3 h. It was cooled 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, separated, and the organic phases were combined. 7 g of anhydrous sodium sulfate was added to the organic phase, stirred and dried, filtered, and the organic phase was concentrated (-0.08 - 0.09 MPa, 55 - 60 °C) until no liquid flowed out. 20 mL of petroleum ether was added with stirring, cooled to 0 - 5 °C, and filtered to obtain compound M-86 with a yield of 65%.

[0130] Elemental analysis: C57H37N3O Theoretical values: C, 87.78; H, 4.78; N, 5.39; O, 2.05; Measured values: C, 87.74; H, 4.79; N, 5.41; HRMS(ESI) m / z [M+H]+: Theoretical value: 779.29; Measured value: 780.28.

[0131] Example 10

[0132] Synthetic route of M-100

[0133]

[0134] After replacing the nitrogen in the three-neck reaction flask equipped with mechanical stirring, thermometer and condenser, add intermediate 100-B (10 mmol), intermediate 7-A (10 mmol) and 100 mL of toluene in sequence, heat to reflux for water separation 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 liquid. Extract the aqueous phase with 100 mL of toluene once, separate the liquid, combine the organic phases, add 7 g of anhydrous sodium sulfate to the organic phases, stir and dry, filter, concentrate the organic phases (-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-100 with a yield of 57%.

[0135] Elemental analysis: C55H34N2O2 Theoretical values: C, 87.51; H, 4.54; N, 3.71; O, 4.24; Measured values: C, 87.54; H, 4.53; N, 3.70; HRMS(ESI) m / z [M+H]+: Theoretical value: 754.26; Measured value: 755.27.

[0136] Example 11

[0137] Synthetic route of M-138

[0138]

[0139] After replacing the nitrogen in a three-necked reaction flask equipped with a mechanical stirrer, a thermometer, and a condenser, 138-B (10 mmol) of the intermediate, 8-A (10 mmol) of the intermediate, and 100 mL of toluene were successively added. The mixture was heated under reflux for water separation for 0.5 h, cooled to 70 - 80 °C, and sodium tert-butoxide (15 mmol), Pd2(dba)3 (0.05 mmol), and s-phos (0.1 mmol) were slowly added. After the system was stabilized, it was heated to 100 - 110 °C and reacted for 3 h. It was cooled 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, separated, and the organic phases were combined. 7 g of anhydrous sodium sulfate was added to the organic phase, stirred and dried, filtered, and the organic phase was concentrated (-0.08 - 0.09 MPa, 55 - 60 °C) until no liquid flowed out. 20 mL of petroleum ether was added with stirring, cooled to 0 - 5 °C, and filtered to obtain compound M-138 with a yield of 47%.

[0140] Elemental analysis: C57H36N2O2 Theoretical values: C, 87.67; H, 4.65; N, 3.59; O, 4.10; Measured values: C, 87.69; H, 4.64; N, 3.58; HRMS(ESI) m / z [M+H]+: Theoretical value: 780.28; Measured value: 781.28.

[0141] Example 12

[0142] Synthesis of M-202

[0143]

[0144] The synthesis steps of compound M202 are the same as those of compound M-32, except that intermediate 202-B is used instead of 32-B, and 6-A is used instead of 4-A to obtain compound M-202 with a yield of 61%.

[0145] Elemental analysis: C 51 H 34 N2O Theoretical values: C, 88.67; H, 4.96; N, 4.06; O, 2.32; Measured values: C, 88.65; H, 4.94; N, 4.10; HRMS(ESI) m / z [M+H]+: Theoretical value: 690.27; Measured value: 691.55.

[0146] Application examples and comparative application examples The following application examples and comparative application examples respectively provide different OLEDs, as Figure 1 shown, all of which have the following layer structure: Substrate 1 (a coated glass substrate with indium tin oxide (ITO) as anode 2) / Hole injection layer 3 (HIL) / Hole transport layer 4 (HTL) / Emitting layer 5 (EML) / Electron transport layer 6 (ETL) / Electron injection layer 7 (EIL), and finally cathode 8.

[0147] The materials used are as follows, where REF-1, REF-2, and REF-3 are comparative compounds:

[0148]

[0149]

[0150] The preparation of the organic electroluminescent devices of Examples 1-9 and Comparative Examples 1-4 includes the following steps:

[0151] (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 ≤ 10 wt%, triethanolamine ≤ 1 wt%), rinsed in deionized water, ultrasonically degreased in a mixed solvent of acetone:ethanol (volume ratio 1:1), baked in a clean environment until all moisture is removed, and then cleaned with ultraviolet light and ozone.

[0152] (2) Evaporation of the organic light-emitting functional layer:

[0153] Place the glass substrate with the anode layer in a vacuum chamber, evacuate to 1×10 -6 to 2×10 -4 Pa, and vacuum evaporate a mixture of HATCN and HT on the anode layer film, where the mass ratio of HATCN to HT is 3:97, as the hole injection layer, with an evaporation thickness of 10 nm;

[0154] Evaporate the hole transport layer (the materials are shown in Table 1) on the hole injection layer, with an evaporation film thickness of 80 nm;

[0155] Evaporate the light-emitting layer on the hole transport layer. The specific preparation method is: vacuum evaporate the light-emitting host material (CBP) and the guest material (piq)2Ir(acac), in a co-evaporation manner, with a total evaporation film thickness of 30 nm;

[0156] Evaporate an electron transport layer on the light-emitting layer. The specific preparation method is: vacuum evaporate the electron transport material (the mass ratio of ET and LiQ is 1) in a co-evaporation manner, with a total evaporation film thickness of 30 nm;

[0157] Vacuum evaporate an electron injection layer (the material is LiQ) on the electron transport layer, with a total evaporation film thickness of 1 nm;

[0158] Evaporate Al on the electron injection layer, with a total evaporation film thickness of 90 nm.

[0159] The parameters such as the layers, their materials, and thicknesses in the device are shown in Table 1 below:

[0160] Table 1

[0161]

[0162]

[0163] Test samples: The organic electroluminescent devices provided in Application Examples 1-10 and Comparative Application Examples 1-2;

[0164] Test instruments: The characteristics such as current, voltage, luminance, and emission spectrum of the devices were synchronously tested using a PR 650 spectral scanning luminance meter and a Keithley K 2400 digital source meter system;

[0165] Test conditions: Photoelectric property test conditions: The current density was 10 mA / cm 2 ;

[0166] Lifetime test: The current density was 50 mA / cm 2 , and the time (in hours) was recorded when the luminance of the device decreased to 95% of the original luminance;

[0167] The test results are shown in Table 2.

[0168] Table 2

[0169] Item Driving Voltage (V) Current Efficiency (Cd / A) Lifetime T95 (hrs) Application Example 1 4.37 16.54 120.4 Application Example 2 4.28 17.15 122.5 Application Example 3 4.35 16.52 118.6 Application Example 4 4.37 16.04 115.3 Application Example 5 4.32 17.52 110.5 Application Example 6 4.30 17.26 120.5 Application Example 7 4.30 17.02 115.9 Application Example 8 4.35 17.35 119.5 Application Example 9 4.32 16.93 116.8 Comparative Example 1 5.34 11.09 64.0 Comparative Example 2 4.72 14.03 92.5 Comparative Example 3 4.54 15.14 105.7 Comparative Example 4 4.60 15.78 110.4

[0170] According to the above device performance tests, compared with the comparative compounds, the devices using the compounds of the present invention as hole transport materials exhibited a reduced driving voltage and a higher current efficiency. The driving voltage of the devices using the organic compounds of the present invention was as low as below 4.37 V, the current efficiency was as high as above 16 Cd / A, and the lifetime was as long as above 110 h

[0171] The preparation of the organic electroluminescent devices of Examples 11-20 and Comparative Examples 5-10 includes the following steps:

[0172] (1) Substrate cleaning: The glass substrate coated with transparent ITO was ultrasonically treated in an aqueous cleaning agent (the composition and concentration of the aqueous cleaning agent: ethylene glycol solvent ≤ 10 wt%, triethanolamine ≤ 1 wt%), rinsed in deionized water, ultrasonically degreased in an acetone:ethanol mixed solvent (volume ratio 1:1), baked in a clean environment until all water was completely removed, and then cleaned with ultraviolet light and ozone.

[0173] (2) Evaporation of the organic light-emitting functional layer:

[0174] The above glass substrate with the anode layer was placed in a vacuum chamber, and the vacuum was pumped to 1×10 -6 to 2×10 -4Pa, a mixture of HATCN and HT with a mass ratio of 3:97 was vacuum-evaporated on the above-mentioned anode layer film as the hole injection layer, and the evaporation thickness was 10 nm;

[0175] A hole transport layer (HT) was vacuum-evaporated on the hole injection layer, and the evaporation film thickness was 80 nm;

[0176] An emission layer was vacuum-evaporated on the hole transport layer. The specific preparation method was: vacuum-evaporating the host material for emission (the materials are shown in Table 3) and the guest material (piq)2Ir(acac) by co-evaporation, and the total evaporation film thickness was 30 nm;

[0177] An electron transport layer was vacuum-evaporated on the emission layer. The specific preparation method was: vacuum-evaporating the electron transport material (the mass ratio of ET and LiQ is 1) by co-evaporation, and the total evaporation film thickness was 30 nm;

[0178] An electron injection layer (the material is LiQ) was vacuum-evaporated on the electron transport layer, and the total evaporation film thickness was 1 nm;

[0179] Al was vacuum-evaporated on the electron injection layer, and the total evaporation film thickness was 90 nm.

[0180] The parameters such as the layers, their materials, and thicknesses in the device are shown in Table 3 below:

[0181] Table 3

[0182]

[0183]

[0184]

[0185]

[0186] Device performance test:

[0187] Test samples: The organic electroluminescent devices provided by the application examples and comparative application examples;

[0188] Test instruments: The characteristics such as the current, voltage, brightness, and emission spectrum of the device were synchronously tested using a PR 650 spectral scanning luminance meter and a Keithley K 2400 digital source meter system;

[0189] Test conditions: Photoelectric characteristic test conditions: The current density was 10 mA / cm 2 ;

[0190] Lifetime test: The current density was 50 mA / cm 2 , and the time (in hours) was recorded when the device brightness decreased to 95% of the original brightness;

[0191] The test results are shown in Table 4 below:

[0192] Table 4

[0193]

[0194]

[0195] The results shown in Table 4 prove that, compared with the comparative compounds, the voltage, lifetime and luminous efficiency of the devices using the organic compounds of the present invention are all improved. The driving voltage of the devices using the organic compounds of the present invention is as low as below 4.58 V, the current efficiency is as high as above 8.5 Cd / A, and the lifetime is as long as above 85 h.

[0196] The organic materials provided by the embodiments of the present invention can match the corresponding light-emitting layer, and have a certain hole-transporting ability. At the same time, during the preparation of the devices, the evaporation temperature is also correspondingly reduced, which is beneficial to the preparation of the devices.

[0197] As a light-emitting material, by combining with the compound N with electron-transporting performance, this material has a synergistic effect in the light-emitting layer, effectively reducing the driving voltage of the device, improving the current operating efficiency and prolonging the lifetime of the device, and making remarkable progress in the application of the host material.

[0198] In summary, the organic electroluminescent material of the present invention has HOMO, LUMO and ET1 values that are close to each other, can reduce the driving voltage of the device, improve the luminous efficiency of the device and prolong the service life of the device.

[0199] The applicant declares that the present invention uses the above embodiments to illustrate the organic compounds of the present invention and their applications, but the present invention is not limited to the above embodiments, that is, it does not mean that the present invention must rely on the above embodiments to be implemented. Those skilled in the art should understand that any improvement to the present invention, the equivalent substitution of the raw materials selected for the present invention, the addition of auxiliary components, the selection of specific methods, etc., all fall within the protection scope and the disclosure scope of the present invention.

Claims

1. An organic compound having the structure shown in Formula I: X is selected from O or S, L, L 1 and L 2 each independently selected from a linking bond, a substituted or unsubstituted C6-C30 arylene group, a substituted or unsubstituted C3-C30 heteroarylene group, Ar is selected from a substituted or unsubstituted C6-C60 aryl group, a substituted or unsubstituted C6-C60 arylamino group, a substituted or unsubstituted C3-C60 heteroarylamino group, and a substituted or unsubstituted C3-C60 heteroaryl group, Ar 1 is selected from hydrogen, deuterium, halogen, cyano, a substituted or unsubstituted C6-C60 aryl group, a substituted or unsubstituted C6-C60 arylamino group, a substituted or unsubstituted C3-C60 heteroarylamino group, and a substituted or unsubstituted C3-C60 heteroaryl group, Ar 2 is selected from a substituted or unsubstituted C6-C60 aryl group, a substituted or unsubstituted C6-C60 arylamino group, a substituted or unsubstituted C3-C60 heteroarylamino group, and a substituted or unsubstituted C3-C60 heteroaryl group, wherein, Ar 1 Any one of the following unsubstituted or substituted benzo[c]carbazolyl groups: The wavy line represents the attachment site of the group; The substituents in the substituted C6-C30 arylene, C3-C30 heteroarylene, substituted C6-C30 aryl, substituted C3-C30 heteroaryl, substituted C6-C60 arylamino, and substituted C3-C60 heteroarylamino are each independently selected from one or a combination of at least two of deuterium, halogen, cyano, C1-C12 alkyl, C3-C12 cycloalkyl, C6-C30 aryl, C3-C30 heteroaryl, C6-C60 arylamino, and C3-C60 heteroarylamino.

2. The organic compound according to claim 1, wherein Ar 1 selected from hydrogen, deuterium, tritium, a substituted or unsubstituted group as follows: phenyl, naphthyl, biphenyl, phenanthryl, fluoranthenyl, anthryl, terphenyl, triphenylene, phenylnaphthyl, naphthylphenyl, carbazolyl, phenylcarbazolyl, dimethylfluorenyl, phenylmethylfluorenyl, diphenylfluorenyl, pyridyl, pyridylphenyl, phenylpyridyl, spirobifluorenyl, benzodimethylfluorenyl, benzodiphenylfluorenyl, benzospirobifluorenyl, dibenzofuranyl, benzonaphthofuranyl, benzonaphthothiophenyl, spiro[fluorene-9,9'-xanthene]yl, phenylmethylfluorenyl, dinaphthofuranyl, dinaphthothiophenyl, dibenzothiophenyl or a C6-C30 arylamine group; Preferably, the C6-C30 arylamino is selected from diphenylamino, dibenzidine, N-phenyl-benzidine, or N-phenyl-dibenzofuranamine; Preferably, the C6-C30 arylamino is diphenylamino; Preferably, Ar 2 is selected from the following substituted or unsubstituted groups: phenyl, naphthyl, biphenyl, phenanthryl, fluoranthenyl, anthryl, terphenyl, triphenylene, phenylnaphthyl, naphthylphenyl, carbazolyl, benzocarbazolyl, dimethylfluorenyl, phenylmethylfluorenyl, diphenylfluorenyl, pyridyl, pyridylphenyl, phenylpyridyl, spirobifluorenyl, benzodimethylfluorenyl, benzodiphenylfluorenyl, benzospirobifluorenyl, dibenzofuranyl, benzonaphthofuranyl, benzonaphthothiophenyl, spiro[fluorene-9,9'-xanthene]yl, phenylmethylfluorenyl, dinaphthofuranyl, dinaphthothiophenyl, dibenzothiophenyl, The substituents are each independently selected from one or a combination of at least two of C1-C6 alkyl, C3-C12 cycloalkyl, C6-C25 aryl, C3-C25 heteroaryl, C6-C60 arylamino, and C3-C60 heteroarylamino.

3. The organic compound according to claim 1 or 2, wherein L, L 1 and L 2 each independently selected from a linking group, a substituted or unsubstituted C6-C30 arylene group; Preferably, L, L 1 and L 2 are each independently selected from a linking bond, a phenylene group, a biphenylene group or a naphthylene group.

4. The organic compound according to any one of claims 1-3, wherein Ar 1 and Ar 2 each independently selected from phenyl, naphthyl, biphenyl, phenanthryl, anthryl, terphenyl, triphenylene, fluoranthenyl, phenylnaphthyl, naphthylphenyl, carbazolyl, dimethylfluorenyl, diphenylfluorenyl, phenylcarbazolyl, phenylphenanthrocarbazolyl, spirobifluorenyl, spiro[fluorene-9,9'-xanthene]yl, phenylmethylfluorenyl, dibenzofuranyl and benzonaphthofuranyl or diphenylamino group.

5. The organic compound according to any one of claims 1-4, wherein Ar is selected from phenyl or naphthyl, and more preferably, Ar is phenyl; Preferably, Ar 2 is naphthyl.

6. The organic compound according to any one of claims 1-5, wherein The organic compound is selected from any one of the following M-1 to M-250:

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

8. An organic electroluminescent device, characterized in that, The organic electroluminescent device includes a cathode, an anode, and an organic layer located between the cathode and the anode, and the organic layer comprises the organic compound according to any one of claims 1-6 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 1-6 or the organic electroluminescent material according to claim 7. Preferably, the organic layer further comprises a light-emitting layer, and the light-emitting layer comprises the organic compound according to any one of claims 1-6 or the organic electroluminescent material according to claim 7; Preferably, the organic layer further comprises at least one of a hole injection 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 a fiber optic 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.

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