Organic compound, mixture, composition and organic light-emitting device

Abstract

The invention relates to an organic compound, a mixture, a composition and an organic light-emitting device, the organic compound has a structure represented by a formula (1): # imgabs0 #, the organic compound provided by the invention simultaneously has a boron-containing heterocyclic ring and an indole carbazolyl group, can be used as a light-emitting material to be applied to the organic light-emitting device, enhances the transmission and spatial effect of the material, and improves the light-emitting efficiency of the organic light-emitting device. The material performance is improved, the light-emitting efficiency of the organic light-emitting device is improved, and the light-emitting service life of the organic light-emitting device is prolonged.

Description

Technical Field

[0001] The present application relates to the field of display, and in particular to an organic compound, a mixture, a composition and an organic light-emitting device. Background Art

[0002] At present, an organic light-emitting diode (OLED) generally has an anode and a cathode and an organic functional layer located between the two. In order to improve the efficiency and life of the organic electroluminescent device, the organic functional layer may have a multilayer structure, each layer containing different organic substances, such as a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, etc. In the organic electroluminescent device, by applying a voltage between two electrodes, holes are injected into the organic functional layer from the anode, and electrons are injected into the organic functional layer from the cathode. When the injected holes and electrons meet, excitons are formed. When the excitons transition back to the ground state, light is emitted, thereby realizing the luminescence of the organic electroluminescent device. The organic electroluminescent device has the characteristics of autonomous luminescence, high brightness, high efficiency, low voltage drive, wide viewing angle, high contrast and high response, and therefore has a wide range of application prospects.

[0003] Accordingly, the development of materials for organic light-emitting diodes (OLEDs) has also attracted widespread attention due to its advantages such as diversity in synthesis, simple composition and process, etc. At the same time, in order to improve the luminous efficiency of organic light-emitting devices, people have tried various material systems with energy transmission and conversion mechanisms, but the luminous efficiency, stability and life of the luminescent materials used in OLED devices (especially the luminescent materials of blue OLED devices) are still low, resulting in limited performance improvement of OLED devices. Summary of the invention

[0004] The embodiments of the present application provide an organic compound, a mixture, a composition and an organic light-emitting device. The organic compound provided in the present application can improve the performance of the light-emitting material, enhance the luminous efficiency of the organic light-emitting device and extend the life of the organic light-emitting device.

[0005] An embodiment of the present application provides an organic compound having a structure shown in formula (1):

[0006]

[0007] wherein Y is selected from O or NR5;

[0008] Ar1, Ar2, Ar3 are independently selected from substituted or unsubstituted aromatic groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaromatic groups having 5 to 30 carbon atoms;

[0009] R1, R2, R3, R4, R5 are independently selected from H, D, substituted or unsubstituted alkyl groups having 1 to 10 carbon atoms, substituted or unsubstituted aromatic groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaromatic groups having 5 to 30 carbon atoms;

[0010] a is selected from integers of 0-2, b is selected from integers of 0-4, and c is selected from integers of 0-4.

[0011] In some embodiments, the organic compound is selected from any one of the structures shown in formula (2) to formula (7):

[0012]

[0013] Wherein, R6 is independently selected from H, D, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aromatic group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaromatic group having 5 to 30 carbon atoms;

[0014] d is an integer selected from 0-4.

[0015] In some embodiments, the organic compound is selected from the structure shown in formula (8):

[0016]

[0017] Wherein, R7 and R8 are independently selected from H, D, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aromatic group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaromatic group having 5 to 30 carbon atoms;

[0018] e is selected from integers of 0-4, and f is selected from integers of 0-4.

[0019] In some embodiments, the organic compound is selected from the structure shown in formula (9):

[0020]

[0021] In some embodiments, R1, R2, R3, R4, R5, R6, R7, and R8 are independently selected from H, D, substituted or unsubstituted methyl, substituted or unsubstituted tert-butyl, substituted or unsubstituted phenyl, substituted or unsubstituted arylamine, substituted or unsubstituted fluorenyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl, and substituted or unsubstituted dibenzothiophenyl.

[0022] In some embodiments, the organic compound is selected from any one of the compounds represented by the following Formulae 1 to 90:

[0023]

[0024]

[0025]

[0026]

[0027]

[0028] An embodiment of the present application also provides a mixture, which includes at least one organic functional material and at least one organic compound as described above, and the organic functional material is selected from hole injection materials, hole transport materials, electron transport materials, electron injection materials, electron blocking materials, hole blocking materials, host materials or organic dyes.

[0029] An embodiment of the present application further provides a composition, which includes at least one organic solvent and at least one organic compound as described above, or the composition includes at least one organic solvent and a mixture as described above.

[0030] An embodiment of the present application further provides an organic light-emitting device, the organic light-emitting device comprising:

[0031] a first electrode;

[0032] a second electrode, disposed opposite to the first electrode; and

[0033] an organic functional layer, located between the first electrode and the second electrode;

[0034] The material of the organic functional layer includes at least one organic compound as described above, or the material of the organic functional layer includes the mixture as described above.

[0035] In some embodiments, the organic functional layer includes a light-emitting layer, the light-emitting layer includes a host material and a guest material, and the guest material includes at least one of the organic compounds.

[0036] The organic compound provided in the present application can be used as a luminescent material in an organic light-emitting device. The organic compound has both a boron-containing heterocycle and an indolecarbazole group, which enhances the transmission and spatial effects of the material. Among them, the boron-nitrogen heterocycle can provide multiple resonances and has the effect of narrowing the luminescence spectrum. The introduction of the indolecarbazole group can improve the transmission performance of the material. The indolecarbazole group is connected to the boron-nitrogen heterocycle through the Ar3 group to more effectively enhance the spatial effect, improve the performance of the material, further improve the luminous efficiency of the organic light-emitting device, and extend the luminous life of the organic light-emitting device. BRIEF DESCRIPTION OF THE DRAWINGS

[0037] Figure 1 A schematic structural diagram of an organic light-emitting device provided in an embodiment of the present application.

[0038] Figure 2 A schematic diagram of the structure of another organic light-emitting device provided in an embodiment of the present application. DETAILED DESCRIPTION

[0039] The following will be combined with the drawings in the embodiments of the present application to clearly and completely describe the technical solutions in the embodiments of the present application. Obviously, the described embodiments are only part of the embodiments of the present application, not all of the embodiments. Based on the embodiments in the present application, all other embodiments obtained by those skilled in the art without creative work are within the scope of protection of the present application. In addition, it should be understood that the specific implementation methods described herein are only used to illustrate and explain the present application, and are not used to limit the present application. In the present application, in the absence of any contrary instructions, the directional words such as "upper" and "lower" used generally refer to the upper and lower parts of the device in actual use or working state, specifically the drawing direction in the accompanying drawings. In the present application, "optionally", "optional", "optional" means optional, that is, it refers to any one of the two parallel schemes of "yes" or "no". If multiple "optional" appear in a technical solution, if there is no special explanation, and there is no contradiction or mutual restriction, each "optional" is independent. In the present application, the technical features described in an open manner include closed technical solutions composed of the listed features, and also include open technical solutions of the listed features.

[0040] In the present application, aromatic group, aromatic, aromatic ring system have the same meaning and can be interchanged. "Aryl or aromatic group or aromatic ring system" refers to an aromatic hydrocarbon group derived from an aromatic ring compound by removing a hydrogen atom, which can be a monocyclic aromatic group, a condensed aromatic group, or a polycyclic aromatic group. For polycyclic ring species, at least one is an aromatic ring system. For example, "substituted or unsubstituted aryl with 6 to 40 ring atoms" refers to an aryl containing 6 to 40 ring atoms, preferably substituted or unsubstituted aryl with 6 to 30 ring atoms, more preferably substituted or unsubstituted aryl with 6 to 18 ring atoms, particularly preferably substituted or unsubstituted aryl with 6 to 14 ring atoms, and the aryl is optionally further substituted; suitable examples include but are not limited to: phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthrenyl, fluoranthenyl, triphenylene, pyrenyl, perylene, naphthyl, fluorenyl, dinaphthylenyl, acenaphthene and its derivatives. It is understandable that multiple aromatic groups may also be interrupted by short non-aromatic units (e.g. <10% non-H atoms, such as C, N or O atoms), specifically acenaphthene, fluorene, or 9,9-diarylfluorene, triarylamine, diaryl ether systems should also be included in the definition of aromatic groups.

[0041] In the present application, heteroaromatic groups, heteroaromatics, and heteroaromatic ring systems have the same meaning and can be interchanged. "Heteroaromatic or heteroaromatic group or heteroaromatic ring system" means that at least one carbon atom on the basis of the aromatic group is replaced by a non-carbon atom, and the non-carbon atom can be an N atom, an O atom, an S atom, etc. For example, "substituted or unsubstituted heteroaryl having 5 to 40 ring atoms" refers to a heteroaryl having 5 to 40 ring atoms, preferably a substituted or unsubstituted heteroaryl having 6 to 30 ring atoms, more preferably a substituted or unsubstituted heteroaryl having 6 to 18 ring atoms, and particularly preferably a substituted or unsubstituted heteroaryl having 6 to 14 ring atoms, and the heteroaryl is optionally further substituted, and suitable examples include, but are not limited to: thienyl, furanyl, pyrrolyl, oxadiazolyl, triazolyl, imidazolyl, pyridyl, bipyridyl, pyrimidyl, Triazine, acridinyl, pyridazinyl, pyrazinyl, quinolyl, isoquinolyl, quinazolinyl, quinoxalinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, benzothiophenyl, benzofuranyl, indolyl, pyrroloimidazolyl, pyrrolopyrrolyl, thienopyrrolyl, thienothiphenyl, furopyrrolyl, furofuranyl, thienofuranyl, benzisoxazolyl, benzisothiazolyl, benzimidazolyl, o-naphthyl, phenanthridinyl, primary pyridyl, quinazolinone, dibenzothiophenyl, dibenzofuranyl, carbazolyl and derivatives thereof.

[0042] In the present application, "substituted" means that one or more hydrogen atoms in the substituted group are replaced by a substituent. When the same substituent appears multiple times, it can be independently selected from different groups. For example, if the general formula contains multiple Rs, R can be independently selected from different groups. In the embodiments of the present application, "substituted or unsubstituted" means that the defined group can be substituted or not substituted; when the defined group is substituted, it should be understood that the defined group can be substituted by one or more substituents R, and the substituents R are selected from but not limited to: deuterium atoms, cyano groups, isocyano groups, nitro groups or halogens, alkyl groups containing 1-20 C atoms, heterocyclic groups containing 3-20 ring atoms, aromatic groups containing 6-20 ring atoms, heteroaromatic groups containing 5-20 ring atoms, -NR'R", silane groups, carbonyl groups, alkoxycarbonyl groups, aryloxycarbonyl groups, carbamoyl groups, haloformyl groups, formyl groups, isocyanate groups, thiocyanate groups, isothiocyanate groups, hydroxyl groups, trifluoromethyl groups, and the above groups can also be further substituted by substituents acceptable in the art; wherein, R in -NR'R" R' and R" are independently selected from but not limited to: H, a deuterium atom, a cyano group, an isocyano group, a nitro group or a halogen, an alkyl group containing 1 to 10 C atoms, a heterocyclic group containing 3 to 20 ring atoms, an aromatic group containing 6 to 20 ring atoms, and a heteroaromatic group containing 5 to 20 ring atoms. Preferably, R is selected from but not limited to: a deuterium atom, a cyano group, an isocyano group, a nitro group or a halogen, an alkyl group containing 1 to 10 C atoms, a heterocyclic group containing 3 to 10 ring atoms, an aromatic group containing 6 to 20 ring atoms, a heteroaromatic group containing 5 to 20 ring atoms, a silane group, a carbonyl group, an alkoxycarbonyl group, an aryloxycarbonyl group, a carbamoyl group, a haloformyl group, a formyl group, an isocyanate group, a thiocyanate group, an isothiocyanate group, a hydroxyl group, a trifluoromethyl group, and the above groups may also be further substituted by substituents acceptable in the art.

[0043] In the present application, "amino group" refers to an amine derivative having a structural feature of the formula -NR'R", where R' and R" have the same meanings as described above.

[0044] In the present application, the "number of ring atoms" refers to the number of atoms among the atoms constituting the ring itself of a structural compound (for example, a monocyclic compound, a condensed ring compound, a cross-linked compound, a carbocyclic compound, a heterocyclic compound) obtained by atoms bonding to form a ring; when the ring is substituted by a substituent, the atoms contained in the substituent are not included in the ring atoms. The same applies to the "number of ring atoms" described below unless otherwise specified. For example, the number of ring atoms of a benzene ring is 6, the number of ring atoms of a naphthalene ring is 10, and the number of ring atoms of a thienyl group is 5.

[0045] In the present application, "*" connected to a single bond indicates a connection or fusion site; when the connection site is not specified in the group, it means that any optional connection site in the group can be used as the connection site; when the same group contains multiple substituents with the same symbol, the substituents can be the same or different from each other, for example The six Rs on the benzene ring may be the same or different from each other; the single bond to which the substituent is connected runs through the corresponding ring, indicating that the substituent can be connected to any position of the ring, for example R is connected to any substitutable position of the benzene ring.

[0046] An embodiment of the present application provides an organic compound having a structure shown in formula (1):

[0047]

[0048] wherein Y is selected from O or NR5;

[0049] Ar1, Ar2, Ar3 are independently selected from substituted or unsubstituted aromatic groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaromatic groups having 5 to 30 carbon atoms;

[0050] R1, R2, R3, R4, R5 are independently selected from H, D, substituted or unsubstituted alkyl groups having 1 to 10 carbon atoms, substituted or unsubstituted aromatic groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaromatic groups having 5 to 30 carbon atoms;

[0051] a is selected from integers of 0-2, b is selected from integers of 0-4, and c is selected from integers of 0-4.

[0052] The organic compound provided in the present application has both a boron-containing heterocycle and an indolecarbazole group, and can be used as a luminescent material in an organic light-emitting device, which can enhance the transmission and spatial effects of the material, improve the material performance, increase the luminous efficiency of the organic light-emitting device, and extend the luminous life of the organic light-emitting device.

[0053] In the present application, the organic compound can be used as a luminescent material in an organic light-emitting device. The organic compound has both a boron-containing heterocycle and an indolecarbazolyl group, which enhances the transmission and spatial effects of the material. Among them, the boron-nitrogen heterocycle can provide multiple resonances and has the effect of narrowing the luminescence spectrum. The introduction of the indolecarbazolyl group can improve the transmission performance of the material. The indolecarbazolyl group is connected to the boron-nitrogen heterocycle through the Ar3 group to more effectively enhance the spatial effect. The organic compound of the present application enhances the resonance effect and the spatial effect, and therefore can improve the luminous efficiency and life of the luminescent material, thereby effectively improving the luminous efficiency and luminous life of the organic light-emitting device.

[0054] In some embodiments, the organic compound is selected from any one of the structures shown in formula (2) to formula (7):

[0055]

[0056] wherein Y is selected from O or NR5;

[0057] Ar1, Ar2, Ar3 are independently selected from substituted or unsubstituted aromatic groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaromatic groups having 5 to 30 carbon atoms;

[0058] R1, R2, R3, R4, R5, R6 are independently selected from H, D, substituted or unsubstituted alkyl groups having 1 to 10 carbon atoms, substituted or unsubstituted aromatic groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaromatic groups having 5 to 30 carbon atoms;

[0059] a is selected from integers of 0 to 2, b is selected from integers of 0 to 4, c is selected from integers of 0 to 4, and d is selected from integers of 0 to 4.

[0060] In some embodiments, the organic compound is selected from the structure shown in formula (8):

[0061]

[0062] wherein, wherein Y is selected from O or NR5;

[0063] Ar2 and Ar3 are independently selected from substituted or unsubstituted aromatic groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaromatic groups having 5 to 30 carbon atoms;

[0064] R1, R2, R3, R4, R5, R7, R8 are independently selected from H, D, substituted or unsubstituted alkyl groups having 1 to 10 carbon atoms, substituted or unsubstituted aromatic groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaromatic groups having 5 to 30 carbon atoms;

[0065] a is selected from integers of 0 to 2, b is selected from integers of 0 to 4, c is selected from integers of 0 to 4, e is selected from integers of 0 to 4, and f is selected from integers of 0 to 4.

[0066] In this embodiment, the organic compound further includes an aromatic amine group, which is connected to a boron nitrogen heterocycle, and can improve the excimer recombination efficiency, thereby further improving the luminescence efficiency of the material. Therefore, the structure shown in formula (8) as a luminescent material can further improve the luminescence efficiency and luminescence life of the organic light-emitting device.

[0067] In some embodiments, the organic compound is selected from the structure shown in formula (9):

[0068]

[0069] wherein, wherein Y is selected from O or NR5;

[0070] Ar3 is selected from a substituted or unsubstituted aromatic group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaromatic group having 5 to 30 carbon atoms;

[0071] R1, R2, R3, R4, R5, R6, R7, R8 are independently selected from H, D, substituted or unsubstituted alkyl groups having 1 to 10 carbon atoms, substituted or unsubstituted aromatic groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaromatic groups having 5 to 30 carbon atoms;

[0072] a is selected from integers of 0 to 2, b is selected from integers of 0 to 4, c is selected from integers of 0 to 4, d is selected from integers of 0 to 4, e is selected from integers of 0 to 4, and f is selected from integers of 0 to 4.

[0073] In this embodiment, the organic compound further comprises a benzothiophene-containing group, and the benzothiophene group is connected to the boron-containing heterocycle, so that the overall planarity of the boron-nitrogen heterocycle is better, which can further improve the luminescence life of the organic light-emitting device.

[0074] In some embodiments, Ar1, Ar2, and Ar3 are independently selected from substituted or unsubstituted aromatic groups having 6 to 20 carbon atoms, and substituted or unsubstituted heteroaromatic groups having 5 to 20 carbon atoms.

[0075] In some embodiments, Ar1, Ar2, and Ar3 are independently selected from substituted or unsubstituted aromatic groups having 6 to 14 carbon atoms, and substituted or unsubstituted heteroaromatic groups having 5 to 14 carbon atoms.

[0076] In some embodiments, R1, R2, R3, R4, R5, R6, R7, and R8 are independently selected from H, D, substituted or unsubstituted alkyl groups having 1 to 10 carbon atoms, substituted or unsubstituted aromatic groups having 6 to 30 carbon atoms, and substituted or unsubstituted heteroaromatic groups having 5 to 30 carbon atoms.

[0077] In some embodiments, R1, R2, R3, R4, R5, R6, R7, and R8 are independently selected from H, D, substituted or unsubstituted alkyl groups having 1 to 5 carbon atoms, substituted or unsubstituted aromatic groups having 6 to 14 carbon atoms, and substituted or unsubstituted heteroaromatic groups having 5 to 14 carbon atoms.

[0078] In some embodiments, R1, R2, R3, R4, R5, R6, R7, and R8 are independently selected from H, D, substituted or unsubstituted methyl, substituted or unsubstituted tert-butyl, substituted or unsubstituted phenyl, substituted or unsubstituted arylamine, substituted or unsubstituted fluorenyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl, and substituted or unsubstituted dibenzothiophenyl.

[0079] Wherein, "substituted or unsubstituted" means that the defined group may be substituted or not, wherein "substituted" means that one or more hydrogen atoms in the defined group are replaced by a substituent, and the substituent may be selected from: deuterium atom, halogen, alkyl group containing 1-20 C atoms, heterocyclic group containing 3-20 ring atoms, aromatic group containing 6-20 ring atoms, heteroaromatic group containing 5-20 ring atoms, silane group, hydroxyl group, trifluoromethyl group, and the above groups may also be further substituted by substituents acceptable in the art.

[0080] In some embodiments, the organic compound is selected from any one of the compounds represented by the following Formulae 1 to 90:

[0081]

[0082]

[0083]

[0084]

[0085] An embodiment of the present application also provides a mixture, which includes at least one organic functional material and at least one organic compound as described above, wherein the organic functional material is selected from a hole injection material (HIM), a hole transport material (HTM), an electron transport material (ETM), an electron injection material (EIM), an electron blocking material (EBM), a hole blocking material (HBM), a host material (Host Emitter) or an organic dye.

[0086] An embodiment of the present application further provides a composition, which includes at least one organic compound as described above and at least one organic solvent, or the composition includes the mixture as described above and at least one organic solvent.

[0087] In some embodiments, the composition may be a solution or a suspension, and the composition may include a dispersant and a dispersant, wherein the dispersant is one or more of the organic compounds described above, and the dispersant is used to disperse the dispersant.

[0088] In the composition, the mass fraction of the organic compound as described above may be 0.01% to 10%, preferably 0.1% to 15%, more preferably 0.2% to 5%, most preferably 0.25% to 3%.

[0089] In some embodiments, the Hansen solubility parameter of the dispersant is within the following range: the δd (dispersion force) of the dispersant is within the range of 17.0 to 23.2 MPa1 / 2, preferably within the range of 18.5 to 21.0 MPa1 / 2; the δp (polar force) is within the range of 0.2 to 12.5 MPa1 / 2, preferably within the range of 2.0 to 6.0 MPa1 / 2; the δh (hydrogen bonding force) is within the range of 0.9 to 14.2 MPa1 / 2, preferably within the range of 2.0 to 6.0 MPa1 / 2.

[0090] In some embodiments, the boiling point of the dispersant is greater than or equal to 150° C., preferably greater than or equal to 180° C., more preferably greater than or equal to 200° C., more preferably greater than or equal to 250° C., further preferably greater than or equal to 275° C., and most preferably ≥300° C. The boiling point of the dispersant is at least greater than or equal to 150° C., which is beneficial for preventing the nozzle of the inkjet print head from being blocked during inkjet printing, and the higher the boiling point, the more beneficial it is for preventing blockage.

[0091] The dispersant may include at least one organic solvent, which may be evaporated from the solvent system to form a film containing a functional material. The organic solvent may include at least one first organic solvent, which may be selected from aromatic or heteroaromatic. Specifically, the first organic solvent may be selected from p-diisopropylbenzene, pentylbenzene, tetralin, cyclohexylbenzene, chloronaphthalene, 1,4-dimethylnaphthalene, 3-isopropylbiphenyl, p-methylisopropylbenzene, dipentylbenzene, tripentylbenzene, pentyltoluene, o-diethylbenzene, m-diethylbenzene, p-diethylbenzene, 1,2,3,4-tetramethylbenzene, 1,2,3,5-tetramethylbenzene, 1,2,4,5-tetramethylbenzene, butylbenzene, dodecylbenzene, dihexylbenzene, dibutylbenzene, p-diisopropylbenzene, cyclohexylbenzene, benzylbutylbenzene, dimethylnaphthalene, 3-isopropyl Biphenyl, p-methylisopropylbenzene, 1-methylnaphthalene, 1,2,4-trichlorobenzene, 4,4-difluorodiphenylmethane, 1,2-dimethoxy-4-(1-propenyl)benzene, diphenylmethane, 2-phenylpyridine, 3-phenylpyridine, N-methyldiphenylamine, 4-isopropylbiphenyl, α,α-dichlorodiphenylmethane, 4-(3-phenylpropyl)pyridine, benzyl benzoate, 1,1-bis(3,4-dimethylphenyl)ethane, 2-isopropylnaphthalene, quinoline, isoquinoline, methyl 2-furoate, ethyl 2-furoate, etc.

[0092] The first organic solvent can be selected from aromatic ketone solvents. Specifically, the first organic solvent can be selected from 1-tetralone, 2-tetralone, 2-(phenylepoxy)tetralone, 6-(methoxy)tetralone, acetophenone, propiophenone, benzophenone, and their derivatives, such as 4-methylacetophenone, 3-methylacetophenone, 2-methylacetophenone, 4-methylpropiophenone, 3-methylpropiophenone, 2-methylpropiophenone, etc.

[0093] The first organic solvent can be selected from aromatic ether solvents. Specifically, the first organic solvent can be selected from 3-phenoxytoluene, butoxybenzene, p-anisaldehyde dimethyl acetal, tetrahydro-2-phenoxy-2H-pyran, 1,2-dimethoxy-4-(1-propenyl)benzene, 1,4-benzodioxane, 1,3-dipropylbenzene, 2,5-dimethoxytoluene, 4-ethyl ethyl ether, 1,3-dipropoxybenzene, 1,2,4-trimethoxybenzene, 4-(1-propenyl)-1,2-dimethoxybenzene, 1,3-dimethoxybenzene, glycidyl phenyl ether, dibenzyl ether, 4-tert-butylanisole, trans-p-propenylanisole, 1,2-dimethoxybenzene, 1-methoxynaphthalene, diphenyl ether, 2-phenoxymethyl ether, 2-phenoxytetrahydrofuran, ethyl-2-naphthyl ether, etc.

[0094] The first organic solvent may be selected from aliphatic ketones. Specifically, the first organic solvent may be selected from aliphatic ketones, such as 2-nonanone, 3-nonanone, 5-nonanone, 2-decanone, 2,5-hexanedione, 2,6,8-trimethyl-4-nonanone, fenchone, phorone, isophorone, di-n-amyl ketone, etc.; or aliphatic ethers, such as amyl ether, hexyl ether, dioctyl ether, ethylene glycol dibutyl ether, diethylene glycol diethyl ether, diethylene glycol butyl methyl ether, diethylene glycol dibutyl ether, triethylene glycol dimethyl ether, triethylene glycol ethyl methyl ether, triethylene glycol butyl methyl ether, tripropylene glycol dimethyl ether, tetraethylene glycol dimethyl ether, etc.

[0095] The first organic solvent may be selected from organic ester solvents. Specifically, the first solvent may be selected from alkyl octanoate, alkyl sebacate, alkyl stearate, alkyl benzoate, ethyl p-methylbenzoate, alkyl phenylacetate, methyl tert-butylbenzoate, alkyl cinnamate, alkyl oxalate, alkyl maleate, alkyl lactone, alkyl oleate, etc. Octyl octanoate, diethyl sebacate, ethyl p-methylbenzoate, methyl tert-butylbenzoate, etc. are particularly preferred.

[0096] The organic solvent may further include a second organic solvent, which may be selected from one or more of methanol, ethanol, 2-methoxyethanol, dichloromethane, chloroform, chlorobenzene, o-dichlorobenzene, tetrahydrofuran, anisole, morpholine, toluene, o-xylene, m-xylene, p-xylene, 1,4-dioxane, acetone, methyl ethyl ketone, 1,2-dichloroethane, 3-phenoxytoluene, 1,1,1-trichloroethane, 1,1,2,2-tetrachloroethane, ethyl acetate, butyl acetate, dimethylformamide, dimethylacetamide, dimethyl sulfoxide, tetralin, decalin, indene and the like.

[0097] In addition to the dispersoid and the dispersant, the composition may also include one or more components such as surfactant compounds, lubricants, wetting agents, dispersants, hydrophobic agents, adhesives, etc., for adjusting viscosity, film-forming properties, improving adhesion, etc.

[0098] The embodiment of the present application also provides an organic light emitting device 100, please refer to Figure 1 The organic light emitting device 100 includes a first electrode 110, a second electrode 120 and an organic functional layer 130. The second electrode 120 is arranged opposite to the first electrode 110, and the organic functional layer 130 is located between the first electrode 110 and the second electrode 120; wherein the material of the organic functional layer 130 includes at least one organic compound as described above; or the material of the organic functional layer 130 includes the mixture as described above.

[0099] In some embodiments, the first electrode 110 may be an anode, and the second electrode 120 may be a cathode, but is not limited thereto.

[0100] In some embodiments, the organic light-emitting device 100 can be used for an organic light-emitting diode, an organic photovoltaic cell, an organic light-emitting cell, an organic field effect transistor, an organic light-emitting field effect transistor, an organic laser, an organic spin electronic device, an organic sensor, and an organic plasmon emission diode, etc., preferably an organic light-emitting diode, an organic light-emitting cell, and an organic light-emitting field effect transistor.

[0101] In some embodiments, the organic light-emitting device 100 can be applied to a variety of electronic devices, such as display panels, lighting devices, light sources, etc.

[0102] In some embodiments, the organic functional layer 130 may be a single layer. In this case, the organic functional layer 130 is a mixture layer, and the mixture layer includes a first compound and a second compound, wherein the first compound is selected from one or more of the organic compounds described above, and the second compound is selected from one or more of a hole injection material, a hole transport material, an electron transport material, a hole blocking material, a host material, or an organic dye.

[0103] When the second compound is selected from one or more of hole injection materials, hole transport materials, electron transport materials, hole blocking materials, light-emitting host materials, and organic dyes, the mass ratio of the first compound to the second compound is 1:99 to 30:70, preferably 1:99 to 10:90.

[0104] When the second compound is a light-emitting guest material, the mass ratio of the first compound to the second compound is 99:1 to 70:30, preferably 99:1 to 90:10.

[0105] In some embodiments, the organic functional layer 130 may include multiple layers. When the organic functional layer 130 is multiple layers, the organic functional layer 130 at least includes a light-emitting layer 131, and the light-emitting layer 131 includes a host material and a guest material, and the guest material includes one or more of the organic compounds described above. The mass ratio of the host material to the guest material in the light-emitting layer 131 is 99:1 to 70:30, and preferably, the mass ratio of the host material to the guest material in the light-emitting layer 131 is 99:1 to 90:10.

[0106] In one embodiment, see Figure 1 When the organic functional layer 130 includes multiple layers, the organic functional layer 130 may include a light-emitting layer 131, a hole injection layer 132, a hole transport layer 133, an electron blocking layer 134, an electron transport layer 135, and an electron injection layer 136. In other embodiments, the organic light-emitting device may further include a hole blocking layer disposed between the light-emitting layer 131 and the electron transport layer 135.

[0107] In some embodiments, the light-emitting layer 131 includes a host material and a guest material, and the guest material is one or more of the organic compounds described above. The mass ratio of the host material to the guest material is 99:1 to 70:30, such as: 98:2, 97:3, 95:5, 90:10, 80:20, 75:25, etc. The guest material is dispersed in the host material, and the mass ratio of the host material to the guest material is 99:1 to 70:30, which is conducive to inhibiting the crystallization of the light-emitting layer and inhibiting the concentration quenching of the guest material due to high concentration, thereby improving the luminous efficiency of the organic light-emitting device 100. Preferably, the host material can be an anthracene, boron oxygen ring or exciplex host material.

[0108] In some embodiments, the light emission wavelength of the organic light emitting device 100 may be between 300nm and 1000nm, preferably between 350nm and 900nm, and more preferably between 400 and 800nm. The light emitted by the organic light emitting device 100 may be red light, green light or blue light, preferably blue light.

[0109] In some embodiments, the anode is an electrode for injecting holes, and the anode can inject holes into the organic functional layer 130, such as: the anode injects holes into the hole injection layer, the hole transport layer or the light-emitting layer. The anode may include at least one of a conductive metal, a conductive metal oxide, or a conductive polymer. Preferably, the absolute value of the difference between the work function of the anode and the HOMO (Highest Occupied Molecular Orbital) energy level or valence band energy level of the light-emitting material in the light-emitting layer, or the p-type semiconductor material in the hole injection layer, the hole transport layer or the electron blocking layer is less than 0.5 eV, preferably less than 0.3 eV, and more preferably less than 0.2 eV. The material of the anode includes but is not limited to: at least one of Al, Cu, Au, Ag, Mg, Fe, Co, Ni, Mn, Pd, Pt, ITO (Indium Tin Oxide), aluminum-doped zinc oxide (AZO), etc., or other suitable and known anode materials, which can be easily selected and used by ordinary technicians in the field. The material of the anode can be deposited using any suitable technique, such as a suitable physical vapor deposition method, including radio frequency magnetron sputtering, vacuum thermal evaporation, electron beam (e-beam), etc. In some embodiments, the anode can be patterned, such as: patterned ITO conductive substrates are commercially available and can be used to prepare organic light-emitting devices according to the present application.

[0110] In some embodiments, the cathode is an electrode for injecting electrons, and the cathode can inject electrons into the organic functional layer, such as: the cathode injects electrons into the electron injection layer, the electron transport layer or the light-emitting layer. The cathode may include at least one of a conductive metal or a conductive metal oxide. Preferably, the absolute value of the difference between the work function of the cathode and the LUMO (Lowest Unoccupied Molecular Orbital) energy level or conduction band energy level of the luminescent material in the light-emitting layer, or the n-type semiconductor material as the electron injection layer, the electron transport layer or the hole blocking layer is less than 0.5 eV, preferably less than 0.3 eV, and more preferably less than 0.2 eV. All materials that can be used as cathodes of organic electronic devices may be used as cathode materials of the device of the present application, and the materials of the cathode include but are not limited to: at least one of Al, Au, Ag, Ca, Ba, Mg, LiF / Al, MgAg alloy, BaF2 / Al, Cu, Fe, Co, Ni, Mn, Pd, Pt, ITO, etc. The cathode material may be deposited using any suitable technique, such as a suitable physical vapor deposition method, including radio frequency magnetron sputtering, vacuum thermal evaporation, electron beam (e-beam), and the like.

[0111] In some embodiments, the hole injection layer is used to promote the injection of holes from the anode to the light-emitting layer, and the hole injection layer includes a hole injection material, which is a material that can receive holes injected from the anode at a low voltage, and preferably, the highest occupied molecular orbital (HOMO) of the hole injection material is between the work function of the material of the anode and the HOMO of the functional material of the film layer into which the holes are injected away from the anode side (such as: the hole transport material of the hole transport layer). The hole injection material includes but is not limited to at least one of metal porphyrin, oligothiophene, organic material based on arylamine, organic material based on hexanitrile hexaazatriphenylene, organic material based on quinacridone, organic material based on perylene, anthraquinone, polyaniline-based and polythiophene-based conductive polymers, etc.

[0112] In some embodiments, the hole transport layer can be used to transport holes to the light-emitting layer, and the hole transport layer includes a hole transport material, and the hole transport material receives holes transmitted from the anode or the hole injection layer and transfers the holes to the light-emitting layer. The hole transport material is a material with high hole mobility known in the art, and the hole transport material may include but is not limited to at least one of an organic material based on arylamine, a conductive polymer, a block copolymer having both a conjugated part and a non-conjugated part, and the like.

[0113] In some embodiments, the electron transport layer is used to transport electrons, and the electron transport layer includes an electron transport material, which receives electrons injected from the cathode and transfers the electrons to the light-emitting layer. The electron transport material is a material with high electron mobility known in the art, and the electron transport material may include but is not limited to: at least one of an Al complex of 8-hydroxyquinoline, a complex containing Alq3, an organic free radical compound, a hydroxyflavone-metal complex, 8-hydroxyquinoline lithium (LiQ), and a benzimidazole-based compound.

[0114] In some embodiments, the electron injection layer is used to inject electrons, and the electron injection layer includes an electron injection material, and the electron injection material preferably has the ability to transport electrons, has the effect of injecting electrons from the cathode, and has an excellent effect of injecting electrons into the light-emitting layer or the light-emitting material, and has the ability to prevent the excitons generated by the light-emitting layer from moving to the hole injection layer, and also has an excellent ability to form a thin film. The electron injection material includes but is not limited to 8-hydroxyquinoline lithium (LiQ), fluorenone, anthraquinone dimethane, diphenoquinone, thiopyran dioxide, azole, diazole, triazole, imidazole, perylene tetracarboxylic acid, fluorenyl methane, anthrone, etc. and their derivatives, metal complex compounds, nitrogen-containing 5-membered ring derivatives, etc. At least one.

[0115] In some embodiments, the hole blocking layer is used to block holes from reaching the cathode, and can generally be formed under the same conditions as the hole injection layer. The hole blocking layer includes a hole blocking material, which includes but is not limited to at least one of a diazole derivative or a triazole derivative, a phenanthroline derivative, BCP, an aluminum complex, and the like.

[0116] In some embodiments, please refer to Figure 1, the organic light-emitting device 100 further includes a substrate 101, and the first electrode 110, the hole injection layer 132, the hole transport layer 133, the electron blocking layer 134, the light-emitting layer 131, the electron transport layer 135, the electron transport layer 135, and the second electrode 120 are sequentially stacked on the substrate 101. The substrate 101 can be a transparent substrate or an opaque substrate. When the substrate 101 is a transparent substrate, a transparent organic light-emitting device can be manufactured; the substrate 101 can be a rigid substrate or a flexible substrate with elasticity, and the material of the substrate 101 can include but is not limited to plastic, polymer, metal, semiconductor wafer or glass. Preferably, the substrate 101 includes at least one smooth surface for forming the anode on the surface. More preferably, the surface has no surface defects. Preferably, the material of the substrate 101 is a polymer film or plastic, including but not limited to polyethylene terephthalate (PET material) and polyethylene glycol (2,6-naphthalene) (PEN material), and the glass transition temperature of the substrate is greater than or equal to 150°C, preferably greater than or equal to 200°C, more preferably greater than or equal to 250°C, and most preferably greater than or equal to 300°C.

[0117] In some embodiments, the organic light-emitting device 100 may be a solution-type organic light-emitting device, that is, at least one of the organic functional layers is prepared by printing (eg, inkjet printing).

[0118] In some embodiments, the mixture layer or the luminescent layer can be formed by a printing or coating process of the composition. The printing or coating process includes inkjet printing, nozzle printing, letterpress printing, screen printing, dip coating, spin coating, blade coating, roller printing, twist roller printing, lithography, flexographic printing, rotary printing, spraying, brushing or pad printing, slit extrusion coating, etc. Preferably, it is gravure printing, nozzle printing and inkjet printing.

[0119] The embodiments of the present application also provide methods for preparing the organic compounds described in the above embodiments, and illustratively provide Examples 1 to 12 to describe the methods for preparing the organic compounds in detail.

[0120] Example 1

[0121] Organic compound M1 Synthesis

[0122] The synthetic route of organic compound M1 is as follows:

[0123]

[0124] The specific synthesis steps of organic compound M1 are as follows:

[0125] Synthesis of intermediate M1-3: Under nitrogen environment, (28.5g, 100mmol) compound M1-1, (22.8g, 100mmol) compound M1-2, (3.31g, 3mmol) tetrakistriphenylphosphine palladium, (27.6g, 200mmol) potassium carbonate 40mL aqueous solution and 200mL toluene were added to a 500mL three-necked flask, heated and stirred to 60°C for 12 hours, the reaction was terminated, cooled to room temperature, the reaction solution was filtered, most of the filtrate was evaporated by rotary evaporation, dissolved in dichloromethane and washed three times, the organic liquid was collected and mixed with silica gel for column chromatography purification to obtain intermediate M1-3 with a yield of 75%.

[0126] Synthesis of intermediate M1-5: Under nitrogen environment, (27.2 g, 70 mmol) of intermediate M1-3, (14.8 g, 70 mmol) of compound M1-4, (1.84 g, 2 mmol) of compound Pd2(dba)3, (0.8 g, 4 mmol) of compound tri-tert-butylphosphine, (12.7 g, 140 mmol) of compound sodium tert-butoxide and 200 mL of anhydrous toluene solvent were mixed and heated to 60 ° C. The reaction was stirred for 6 hours, cooled to room temperature, and quenched with water twice. Most of the solvent was evaporated from the reaction solution by rotary evaporation, dissolved with dichloromethane and washed with water 3 times, the organic liquid was collected and mixed with silica gel for column chromatography purification to obtain intermediate M1-5 with a yield of 82%.

[0127] Synthesis of intermediate M1-7: Under nitrogen environment, (26 g, 50 mmol) of intermediate M1-5, (4.1 g, 50 mmol) of compound M1-6, (1.66 g, 1.8 mmol) of compound Pd2(dba)3, (0.72 g, 3.6 mmol) of compound tri-tert-butylphosphine, (9.2 g, 100 mmol) of compound sodium tert-butoxide and 150 mL of anhydrous toluene solvent were mixed and heated to 90 ° C. The reaction was stirred for 6 hours, cooled to room temperature, quenched with water twice, and the reaction solution was rotary evaporated to remove most of the solvent. The reaction solution was dissolved with dichloromethane and washed with water 3 times. The organic liquid was collected and mixed with silica gel for column chromatography purification to obtain intermediate M1-7 with a yield of 76%.

[0128] Synthesis of organic compound M1: Under nitrogen environment, (29g, 30mmol) compound M1-7 and 100mL anhydrous tetrahydrofuran were mixed, cooled to -30°C, and 35mmol of tert-butyl lithium solution was slowly added dropwise. After the addition was completed, the reaction was heated to 60°C and stirred for 2 hours. The reaction was cooled to -30°C, and 40mmol of boron tribromide was added at once. The reaction was naturally heated to room temperature for 1 hour. Then 40mmol of N,N-diisopropylethylamine was added, and the temperature was slowly raised to 100°C for 3 hours. The reaction was terminated, cooled to room temperature, and sodium acetate aqueous solution was added to quench the reaction. Most of the solvent was evaporated by rotary evaporation, dissolved with dichloromethane and washed with water 3 times, and the organic liquid was collected and rotary evaporated and purified by column chromatography to obtain organic compound M1 with a yield of 30%. Atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) results of organic compound M1: mass-to-charge ratio was 941 [M + ].

[0129] Example 2

[0130] Organic Compound M2 Synthesis

[0131] The synthetic route of organic compound M2 is as follows:

[0132]

[0133] The specific synthesis steps of organic compound M2 are as follows:

[0134] Synthesis of intermediate M2-2: According to the synthesis method of compound M1-5, compound M2-1 was substituted for compound M1-4 to obtain intermediate M2-2 with a yield of 80%.

[0135] Synthesis of intermediate M2-4: According to the synthesis method of compound M1-7, compounds M2-2 and M2-3 were used to replace compounds M1-5 and M1-6, respectively, to obtain intermediate M2-4 with a yield of 74%.

[0136] Synthesis of organic compound M2: According to the synthesis method of compound M1, compound M2-4 was substituted for compound M1-7 to obtain organic compound M2 with a yield of 28%. The results of atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) of organic compound M2: mass-to-charge ratio was 1182 [M + ].

[0137] Example 3

[0138] Organic Compound M3 Synthesis

[0139] The synthetic route of organic compound M3 is as follows:

[0140]

[0141] The specific synthesis steps of organic compound M3 are as follows:

[0142] Synthesis of intermediate M3-2: According to the synthesis method of compound M1-5, compound M3-1 was used instead of compound M1-4 to obtain intermediate M3-2 with a yield of 81%.

[0143] Synthesis of intermediate M3-4: According to the synthesis method of compound M1-7, compounds M3-2 and M3-3 were used to replace compounds M1-5 and M1-6, respectively, to obtain intermediate M3-4 with a yield of 75%.

[0144] Synthesis of organic compound M3: According to the synthesis method of compound M1, compound M3-4 was substituted for compound M1-7 to obtain organic compound M3 with a yield of 29%. The results of atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) of organic compound M3: mass-to-charge ratio was 1422 [M + ].

[0145] Example 4

[0146] Organic Compound M4 Synthesis

[0147] The synthetic route of organic compound M4 is as follows:

[0148]

[0149] The specific synthesis steps of organic compound M4 are as follows:

[0150] Synthesis of intermediate M4-2: According to the synthesis method of compound M1-7, compound M4-1 was used to replace compound M1-6 to obtain intermediate M4-2 with a yield of 77%.

[0151] Synthesis of organic compound M4: According to the synthesis method of compound M1, compound M4-2 was substituted for compound M1-7 to obtain organic compound M4 with a yield of 32%. The results of atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) of organic compound M4: mass-to-charge ratio was 924 [M + ].

[0152] Example 5

[0153] Organic Compound M5 Synthesis

[0154] The synthetic route of organic compound M5 is as follows:

[0155]

[0156] The specific synthesis steps of organic compound M5 are as follows:

[0157] Synthesis of intermediate M5-2: According to the synthesis method of compound M1-7, compound M5-1 was used to replace compound M1-6 to obtain intermediate M5-2 with a yield of 76%.

[0158] Synthesis of organic compound M5: According to the synthesis method of compound M1, compound M5-2 was substituted for compound M1-7 to obtain organic compound M5 with a yield of 31%. The results of atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) of organic compound M5: mass-to-charge ratio was 857 [M + ].

[0159] Example 6

[0160] Organic Compound M6 Synthesis

[0161] The synthetic route of organic compound M6 is as follows:

[0162]

[0163] The specific synthesis steps of organic compound M6 are as follows:

[0164] Synthesis of intermediate M6-3: According to the synthesis method of compound M1-5, compounds M6-1 and M6-2 were used to replace compounds M1-4 and M1-3, respectively, to obtain intermediate M6-3 with a yield of 83%.

[0165] Synthesis of intermediate M6-4: According to the synthesis method of compound M1-7, compound M6-3 was used instead of compound M1-6 to obtain intermediate M6-4 with a yield of 74%.

[0166] Synthesis of organic compound M6: According to the synthesis method of compound M1, compound M6-4 was substituted for compound M1-7 to obtain organic compound M6 with a yield of 28%. The results of atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) of organic compound M6: mass-to-charge ratio was 1075 [M + ].

[0167] Example 7

[0168] Organic Compound M7 Synthesis

[0169] The synthetic route of organic compound M7 is as follows:

[0170]

[0171] The specific synthesis steps of organic compound M7 are as follows:

[0172] Synthesis of intermediate M7-3: According to the synthesis method of compound M1-5, compounds M7-1 and M7-2 were used to replace compounds M1-4 and M1-3, respectively, to obtain intermediate M7-3 with a yield of 82%.

[0173] Synthesis of intermediate M7-4: According to the synthesis method of compound M1-7, compound M7-3 was used instead of compound M1-6 to obtain intermediate M7-4 with a yield of 75%.

[0174] Synthesis of organic compound M7: According to the synthesis method of compound M1, compound M7-4 was substituted for compound M1-7 to obtain organic compound M7 with a yield of 29%. The results of atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) of organic compound M7: mass-to-charge ratio was 1128 [M + ].

[0175] Example 8

[0176] Organic Compound M8 Synthesis

[0177] The synthetic route of organic compound M8 is as follows:

[0178]

[0179] The specific synthesis steps of organic compound M8 are as follows:

[0180] Synthesis of intermediate M8-2: According to the synthesis method of compound M1-7, compound M8-1 was used to replace compound M1-6 to obtain intermediate M8-2 with a yield of 83%.

[0181] Synthesis of intermediate M8-4: According to the synthesis method of compound M1-7, compounds M8-2 and M8-3 were used to replace compounds M1-6 and M1-5, respectively, to obtain intermediate M8-4 with a yield of 76%.

[0182] Synthesis of intermediate M8-6: According to the synthesis method of compound M1-7, compounds M8-4 and M8-5 were used to replace compounds M1-5 and M1-6, respectively, to obtain intermediate M8-6 with a yield of 73%.

[0183] Synthesis of organic compound M8: According to the synthesis method of compound M1, compound M8-6 was substituted for compound M1-7 to obtain organic compound M8 with a yield of 27%. The results of atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) of organic compound M8: mass-to-charge ratio was 1106 [M + ].

[0184] Example 9

[0185] Organic Compound M9 Synthesis

[0186] The synthetic route of organic compound M9 is as follows:

[0187]

[0188] The specific synthesis steps of organic compound M9 are as follows:

[0189] Synthesis of intermediate M9-2: According to the synthesis method of compound M1-3, compound M9-1 was substituted for compound M1-2 to obtain intermediate M9-2 with a yield of 78%.

[0190] Synthesis of intermediate M9-4: According to the synthesis method of compound M1-7, compounds M9-2 and M9-3 were used to replace compounds M1-5 and 1-6, respectively, to obtain intermediate M9-4 with a yield of 74%.

[0191] Synthesis of intermediate M9-5: According to the synthesis method of compound M1-7, compounds M9-4 and M9-5 were used to replace compounds M1-5 and 1-6, respectively, to obtain intermediate M9-5 with a yield of 73%.

[0192] Synthesis of organic compound M9: According to the synthesis method of compound M1, compound M9-6 was substituted for compound M1-7 to obtain organic compound M9 with a yield of 28%. The results of atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) of organic compound M9: mass-to-charge ratio was 1158 [M + ].

[0193] Example 10

[0194] Organic Compound M10 Synthesis

[0195] The synthetic route of organic compound M10 is as follows:

[0196]

[0197] The specific synthesis steps of organic compound M10 are as follows:

[0198] Synthesis of intermediate M10-1: According to the synthesis method of compound M1-5, compound M8-5 was used instead of compound M1-4 to obtain intermediate M10-1 with a yield of 79%.

[0199] Synthesis of intermediate M10-4: According to the synthesis method of compound M1-7, compounds M10-2 and M10-3 were used to replace compounds M1-5 and M1-6, respectively, to obtain intermediate M10-4 with a yield of 75%.

[0200] Synthesis of intermediate M10-5: According to the synthesis method of compound M1-7, compounds M10-1 and M10-4 were used to replace compounds M1-5 and 1-6, respectively, to obtain intermediate M10-5 with a yield of 74%.

[0201] Synthesis of organic compound M10: According to the synthesis method of compound M1, compound M10-4 was substituted for compound M1-7 to obtain organic compound M10 with a yield of 27%. The results of atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) of organic compound M10: mass-to-charge ratio was 1310 [M + ].

[0202] Embodiment 11

[0203] Organic Compound M11 Synthesis

[0204] The synthetic route of organic compound M11 is as follows:

[0205]

[0206] The specific synthesis steps of organic compound M11 are as follows:

[0207] Synthesis of intermediate M11-2: According to the synthesis method of compound M1-7, compounds M8-1 and M11-1 were used to replace compounds M1-6 and M1-5, respectively, to obtain intermediate M11-2 with a yield of 77%.

[0208] Synthesis of intermediate M11-3: According to the synthesis method of compound M1-7, compounds M11-1 and M10-1 were used to replace compounds M1-5 and 1-6, respectively, to obtain intermediate M11-3 with a yield of 73%.

[0209] Synthesis of organic compound M11: According to the synthesis method of compound M1, compound M11-3 was substituted for compound M1-7 to obtain organic compound M11 with a yield of 29%. The results of atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) of organic compound M11: mass-to-charge ratio was 1198 [M + ].

[0210] Example 12

[0211] Organic Compound M12 Synthesis

[0212] The synthetic route of organic compound M12 is as follows:

[0213]

[0214] The specific synthesis steps of organic compound M12 are as follows:

[0215] Synthesis of intermediate M12-3: According to the synthesis method of compound M1-3, compound M12-1 was substituted for compound M1-1 to obtain intermediate M12-3 with a yield of 80%.

[0216] Synthesis of intermediate M12-4: According to the synthesis method of compound M1-5, compounds M12-2 and M12-3 were used to replace compounds M1-3 and M1-4, respectively, to obtain intermediate M12-4 with a yield of 76%.

[0217] Synthesis of intermediate M12-6: According to the synthesis method of compound M1-5, compounds M12-4 and M12-5 were used to replace compounds M1-3 and M1-4, respectively, to obtain intermediate M12-6 with a yield of 74%.

[0218] Synthesis of organic compound M12: According to the synthesis method of compound M1, compound M12-6 was substituted for compound M1-7 to obtain organic compound M12 with a yield of 27%. The results of atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) of organic compound M12: mass-to-charge ratio was 1240 [M + ].

[0219] The embodiments of the present application also provide exemplary manufacturing steps of the organic light-emitting device described in the above embodiments, as shown below.

[0220] Please refer to Figure 2 In this embodiment, the structure of an organic light-emitting device 200 is taken as an example. The organic light-emitting device 200 includes: a substrate 101, a first electrode 110 (anode ITO), a hole injection layer 132 (thickness 40nm), a hole transport layer 133 (thickness 100nm), a light-emitting layer 131 (host material: 3% (mass ratio) guest material) (thickness 50nm), an electron transport layer 135 (thickness 25nm), and a second electrode 120 (cathode LiQ (thickness 1nm) / Al (thickness 150nm)), which are stacked in sequence. The steps of preparing the organic light-emitting device 200 are as follows:

[0221] a. Cleaning of the conductive glass substrate: When used for the first time, the conductive glass substrate is cleaned with a solvent and then subjected to ultraviolet ozone plasma treatment, wherein the conductive glass substrate includes a substrate 101 and an anode formed on the substrate 101, and the solvent includes chloroform, ketone, isopropyl alcohol, etc.;

[0222] b. Formation of organic functional layer: High vacuum (1×10 -6 mbar), thermally evaporating films in the order of a hole injection layer (40 nm), a hole transport layer (100 nm), a light emitting layer (50 nm), and an electron transport layer (25 nm) on the cleaned conductive glass substrate;

[0223] c. Cathode formation: High vacuum (1×10 -6 mbar) under the condition of thermal evaporation of LiQ (1nm) / Al (150nm) to form the cathode;

[0224] d. Packaging: The device obtained in step c is packaged with ultraviolet curing resin in a nitrogen glove box.

[0225] Through the above steps, organic compounds M1-M12 are used as the guest materials to form organic light-emitting devices 1-12, and organic compound Ref-1 is used as the guest material to form comparative element 1. Organic light-emitting devices 1-12 and comparative element 1 are different only in the guest materials used, and other materials and preparation steps used in organic light-emitting devices 1-12 and comparative element 1 are the same. Among them, the structures of organic compound Ref-1 and other materials involved are as follows:

[0226] The structural formula of Ref-1 is:

[0227] The structural formula of the material of the hole injection layer is:

[0228] The structural formula of the material of the hole transport layer is:

[0229] The structural formula of the host material in the light-emitting layer is:

[0230] The structural formula of the material of the electron transport layer is:

[0231] The structural formula of LiQ is:

[0232] In the embodiments of the present application, external quantum efficiency (EQE) and luminescence lifetime tests (T90@1000nits, which refers to the time for the device to be tested to decay from 1000 nits to 900 nits) were performed on organic light-emitting devices 1 to 12 and comparative element 1, and the results are shown in Table 1.

[0233] Table 1 Performance data of organic light emitting devices 1 to 15 and comparative element 1

[0234] OLED Devices Object material EQE T90@1000nits Organic light-emitting devices1 M1 1.55 1.64 Organic light-emitting devices2 M2 1.61 1.71 Organic light-emitting devices3 M3 1.68 1.80 Organic light-emitting devices4 M4 1.54 1.62 Organic light-emitting devices5 M5 1.52 1.61 Organic light-emitting devices6 M6 1.67 1.78 Organic light-emitting devices7 M7 1.57 1.66 Organic light-emitting devices8 M8 1.63 1.72 Organic light-emitting devices9 M9 1.58 1.68 Organic light emitting device 10 M10 1.64 1.74 Organic light-emitting device11 M11 1.60 1.69 Organic light emitting device 12 M12 1.65 1.76 Comparison Component 1 Ref-1 1 1

[0235] It can be seen from the data in Table 1 that, taking the external quantum efficiency and luminescence lifetime of the comparative element 1 as the reference value 1, compared with the comparative element 1, the external quantum efficiency of the organic light-emitting devices 1 to 12 of the present application is significantly improved, and the luminescence lifetime is also effectively extended, indicating that the use of the organic compound of the present application as the guest material of the light-emitting layer can effectively improve the luminescence efficiency and luminescence lifetime of the organic light-emitting device. The reason is that, compared with the comparative compound Ref-1, the organic compound of the present application further introduces an indolecarbazole group on the boron-containing heterocycle, and the organic compound has both a boron-containing heterocycle and an indolecarbazole group, which enhances the resonance effect and the steric effect of the organic compound, improves the performance of the guest material, and therefore can effectively improve the luminescence efficiency and luminescence lifetime of the organic light-emitting device.

[0236] The organic compound of the present application has both a boron-containing heterocycle and an indolecarbazolyl group, which enhances the transmission and spatial effect of the material. Among them, the boron-nitrogen heterocycle can provide multiple resonances, which has the effect of narrowing the luminescence spectrum. The introduction of the indolecarbazolyl group can improve the transmission performance of the material. The indolecarbazolyl group is connected to the boron-nitrogen heterocycle through the Ar3 group to more effectively enhance the spatial effect. The organic compound of the present application enhances the resonance effect and the spatial effect, improves the performance of the luminescent material, and therefore can effectively improve the luminous efficiency and luminous life of the organic light-emitting device.

[0237] The technical features of the above-described embodiments may be arbitrarily combined. To make the description concise, not all possible combinations of the technical features in the above-described embodiments are described. However, as long as there is no contradiction in the combination of these technical features, they should be considered to be within the scope of this specification.

[0238] The above-mentioned embodiments only express several implementation methods of the present application, and the descriptions thereof are relatively specific and detailed, but they cannot be understood as limiting the scope of the invention patent. It should be pointed out that, for a person of ordinary skill in the art, several variations and improvements can be made without departing from the concept of the present application, and these all belong to the protection scope of the present application. Therefore, the protection scope of the patent of the present application shall be subject to the attached claims.

Claims

1. An organic compound, characterized in that The organic compound has a structure shown in formula (1): wherein Y is selected from O or NR5; Ar1, Ar2, Ar3 are independently selected from substituted or unsubstituted aromatic groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaromatic groups having 5 to 30 carbon atoms; R1, R2, R3, R4, R5 are independently selected from H, D, substituted or unsubstituted alkyl groups having 1 to 10 carbon atoms, substituted or unsubstituted aromatic groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaromatic groups having 5 to 30 carbon atoms; a is selected from integers of 0-2, b is selected from integers of 0-4, and c is selected from integers of 0-4.

2. The organic compound according to claim 1, characterized in that The organic compound is selected from any one of the structures shown in formula (2) to formula (7): Wherein, R6 is selected from H, D, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aromatic group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaromatic group having 5 to 30 carbon atoms; d is an integer selected from 0-4.

3. The organic compound according to claim 2, characterized in that The organic compound is selected from the structure shown in formula (8): Wherein, R7 and R8 are independently selected from H, D, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aromatic group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaromatic group having 5 to 30 carbon atoms; e is selected from integers of 0-4, and f is selected from integers of 0-4.

4. The organic compound according to claim 3, characterized in that The organic compound is selected from the structure shown in formula (9):

5. The organic compound according to claim 4, characterized in that R1, R2, R3, R4, R5, R6, R7, and R8 are independently selected from H, D, substituted or unsubstituted methyl, substituted or unsubstituted tert-butyl, substituted or unsubstituted phenyl, substituted or unsubstituted aromatic amine, substituted or unsubstituted fluorenyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl, and substituted or unsubstituted dibenzothiophenyl.

6. The organic compound according to claim 1, characterized in that The organic compound is selected from any one of the compounds represented by the following formula 1 to formula 90:

7. A mixture, characterized in that The mixture comprises at least one organic functional material and at least one organic compound as described in any one of claims 1 to 6, wherein the organic functional material is selected from hole injection materials, hole transport materials, electron transport materials, electron injection materials, electron blocking materials, hole blocking materials, host materials or organic dyes.

8. A composition, characterized in that The composition comprises at least one organic solvent and at least one organic compound according to any one of claims 1 to 6, or the composition comprises at least one organic solvent and a mixture according to claim 7.

9. An organic light-emitting device, characterized in that: include: a first electrode; a second electrode, arranged opposite to the first electrode; as well as an organic functional layer, located between the first electrode and the second electrode; The material of the organic functional layer includes at least one organic compound according to any one of claims 1 to 6, or the material of the organic functional layer includes the mixture according to claim 7.

10. The organic light emitting device according to claim 9, characterized in that: The organic functional layer includes a light-emitting layer, the light-emitting layer includes a host material and a guest material, and the guest material includes at least one of the organic compounds.

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