Organic compound, mixture, composition, organic electronic device and display panel

Abstract

The invention relates to an organic compound, a mixture, a composition, an organic electronic device and a display panel. The organic compound has a structural formula as shown in a formula (I): # imgabs0 #. The organic compound provided by the invention has enough strong hole transport property and stability, and when the organic compound is applied to a light-emitting auxiliary layer, effective exciton blocking can be realized, reverse transport of excitons can be inhibited, the luminous efficiency of the organic electroluminescent device can be improved, and the service life of the organic electroluminescent device can be prolonged.

Description

Technical Field

[0001] The present application relates to the field of display technologies, and particularly to an organic compound, a mixture, a composition, an organic electronic device, and a display panel. Background Art

[0002] Currently, an organic electroluminescent element generally includes an anode, a cathode, and an organic functional layer located therebetween, and uses an organic substance in the organic layer to convert electrical energy into light energy, thereby realizing organic electroluminescence. To improve the luminous efficiency and service life of the organic electroluminescent element, the organic functional layer often includes a multi-layer structure, and the organic substances in each layer are different. Specifically, the organic layer generally includes, but is not limited to, a hole injection layer, a hole transport layer, a luminescence assisting layer, a light-emitting layer, a hole blocking layer, an electron transport layer, an electron injection layer, etc. When the organic electroluminescent element works, by applying a voltage between the anode and the cathode, the anode injects holes into the organic layer, and the cathode injects electrons into the organic layer. The injected holes and electrons meet to form excitons, and when the excitons return to the ground state through radiative transition, light is emitted, thereby realizing the light emission of the organic electroluminescent element. With the characteristics of self-luminescence, high brightness, high efficiency, low-voltage driving, wide viewing angle, high contrast, and high response, etc., the organic electroluminescent element has broad application prospects and great development potential.

[0003] In the light-emitting layer, the energy of the excitons reaching the excited state is higher than that of the ground state. Without blocking, the excitons in the excited state will diffuse to the adjacent functional layer, resulting in a decrease in the device efficiency and life. Therefore, the development of materials for the luminescence assisting layer is crucial. By using a luminescence assisting material with appropriate carrier transport ability and excited state energy level, the organic electroluminescent device can achieve the balance of carrier transport, block the excitons in the light-emitting layer, make the electrons and holes recombine in the central region of the light-emitting layer, and further reduce the quenching of excitons, effectively improving the luminous efficiency and device life. However, the existing organic electroluminescent assisting materials have insufficient transportability and low stability, which easily lead to the voltage, efficiency, and life of the device not meeting the requirements, severely limiting the application of the organic electroluminescent element. Summary of the Invention

[0004] The present application provides an organic compound, a mixture, a composition, an organic electronic device, and a display panel. The organic compound has good carrier transport characteristics, can adjust the charge balance, promote energy transport, and block exciton diffusion, and can be used as a luminescence assisting material in an organic electronic device to improve the luminous efficiency and life of the device.

[0005] To achieve the above object, according to an embodiment of the present application, an organic compound is provided, and the organic compound has a structural formula shown in formula (Ⅰ):

[0006]

[0007] Among them, X is selected from O, S or CR 4 R 5 ;

[0008] R 1 is selected from substituted or unsubstituted alkyl groups having 1 to 5 carbon atoms;

[0009] R 2 is selected from hydrogen, deuterium, straight-chain alkyl groups having 1 to 12 carbon atoms, branched-chain alkyl groups having 3 to 12 carbon atoms, cyclic alkyl groups having 3 to 12 carbon atoms, substituted or unsubstituted aromatic groups having 6 to 12 carbon atoms, and substituted or unsubstituted heteroaromatic groups having 5 to 12 carbon atoms;

[0010] R 3 is selected from hydrogen, deuterium, alkyl groups having 1 to 5 carbon atoms or aryl groups having 6 to 12 carbon atoms;

[0011] R 4 and R 5 are selected from alkyl groups having 1 to 5 carbon atoms or aryl groups having 6 to 12 carbon atoms;

[0012] Ar is selected from substituted or unsubstituted aromatic groups having 6 to 18 carbon atoms, and substituted or unsubstituted heteroaromatic groups having 5 to 18 carbon atoms;

[0013] n1 is selected from any integer from 0 to 4;

[0014] n2 is selected from any integer from 0 to 7;

[0015] n3 is selected from any integer from 0 to 4.

[0016] In one embodiment of the present application, R 1 is selected from isopropyl, tert-butyl or -C(CD3)3;

[0017] R 2 is selected from hydrogen or phenyl;

[0018] R 3 is selected from hydrogen, deuterium, methyl or phenyl;

[0019] R 4 and R 5 are selected from methyl or phenyl.

[0020] In one embodiment of the present application, Ar is selected from at least one of substituted or unsubstituted phenyl, biphenyl, terphenyl, phenylnaphthyl, dibenzofuranyl, dibenzothiophenyl, 9-phenylcarbazolyl, 9,9-dimethylfluorenyl, 9-methyl-9-phenylfluorenyl, 9,9-diphenylfluorenyl.

[0021] In one embodiment of the present application, the organic compound has a structural formula represented by Formula (1) or Formula (2):

[0022]

[0023] In one embodiment of the present application, the organic compound has a structural formula represented by Formula (3), Formula (4), Formula (5) or Formula (6):

[0024]

[0025] For the above object of the present application, an embodiment of the present application further provides a mixture, which includes at least one of the organic compounds and at least one organic functional material, and the organic functional material is selected from at least one of a hole injection material, a hole transport material, an electron injection material, an electron transport material, a luminescence assisting material, a hole blocking material, a guest material, a host material, and an inorganic quantum dot.

[0026] For the above object of the present application, an embodiment of the present application further provides a composition, which includes at least one organic solvent and at least one of the organic compounds, or the composition includes at least one of the organic solvents and the mixture.

[0027] For the above object of the present application, an embodiment of the present application further provides an organic electronic device, which includes:

[0028] A first electrode;

[0029] A second electrode, which is disposed opposite to the first electrode;

[0030] An organic functional layer, which is located between the first electrode and the second electrode, and the material of the organic functional layer includes at least one of the organic compounds, or the material of the organic functional layer includes the mixture, or the organic functional layer is made of the composition.

[0031] In one embodiment of the present application, the organic functional layer includes a luminescence assisting layer and a light emitting layer which are stacked, and the material of the luminescence assisting layer includes at least one of the organic compounds.

[0032] For the above object of the present application, an embodiment of the present application further provides a display panel, which includes the organic electronic device.

[0033] The present application provides an organic compound, a mixture, a composition, an organic electronic device, and a display panel. The molecular structure of the organic compound is composed of a nitrogen atom with electrophilic hybridization, paired with a substituted or unsubstituted 9-methyl-9-phenylfluorene group and a dibenzofuran / thiophene group, enabling the organic compound to have sufficiently strong hole transport properties and stability. When the organic compound is applied to the light-emitting auxiliary layer, effective exciton blocking can be achieved, inhibiting the reverse transport of excitons, which is beneficial to improving the luminous efficiency and lifespan of the organic electroluminescent device. At the same time, when isopropyl, tert-butyl, and their deuterated compounds are connected to the 2nd position or the 1st and 3rd positions of the fluorene ring, the steric hindrance provided by the alkane side chain affects the stacking of the organic compound, thereby further enhancing the hole transport ability and stability of the organic compound thin film. Therefore, it is beneficial to improve the luminous efficiency and service life of the organic electronic device prepared with the organic compound provided by the present application.

[0034] Other features and advantages of the present application will be described in detail in the subsequent specific implementation section. Brief Description of the Drawings

[0035] To more clearly illustrate the technical solutions in the embodiments of the present application, the following will briefly introduce the drawings required for the description of the embodiments. Obviously, the following drawings are only some embodiments of the present application. For those skilled in the art, without creative efforts, other drawings can also be obtained based on these drawings.

[0036] To more fully understand the present application and its beneficial effects, the following description will be made in conjunction with the drawings, where the same reference numerals represent the same parts in the following description.

[0037] Figure 1 It is a schematic structural diagram of the organic electronic device provided by the embodiment of the present application.

[0038] Description of the Reference Numerals in the Drawings:

[0039] 100, organic electronic device; 1, substrate; 11, first electrode; 12, hole injection layer; 13, hole transport layer; 14, light-emitting auxiliary layer; 15, light-emitting layer; 16, electron transport layer; 17, electron injection layer; 18, second electrode. Detailed Description of the Embodiments

[0040] Next, the technical solutions in the embodiments of the present application will be clearly and completely described in conjunction with the accompanying drawings in the embodiments of the present application. Obviously, the described embodiments are only a part of the embodiments of the present application, rather than all the embodiments. Based on the embodiments in the present application, all other embodiments obtained by those skilled in the art without making creative efforts belong to the scope of protection of the present application. In addition, it should be understood that the specific implementation manners 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, unless otherwise stated, the orientation terms such as "upper" and "lower" usually refer to the upper and lower in the actual use or working state of the device, specifically the drawing direction in the drawings; and "inner" and "outer" refer to the outline of the device. In the present application, "optionally", "optional", "optional" mean having or not having, that is, either one of the two parallel options of "having" or "not having". If the term "optional" appears in multiple places in a technical solution, without special explanation and without contradiction or mutual restriction relationship, each "optional" is independent of each other. In the present application, for the technical features described in an open-ended manner, it includes a closed technical solution composed of the listed features, and also includes an open technical solution containing the listed features.

[0041] In the present application, the aromatic group, aromatic and aromatic ring system have the same meaning and can be interchanged.

[0042] In the present application, the heteroaromatic group, heteroaromatic and heteroaromatic ring system have the same meaning and can be interchanged.

[0043] In the present application, "substituted" means that a hydrogen atom in the substituent is replaced by a substituent.

[0044] In the present application, when the same substituent appears multiple times, it can be independently selected from different groups. For example, if the general formula contains multiple Rs, then R can be independently selected from different groups.

[0045] In the present application, "substituted or unsubstituted" means that the defined group can be substituted or unsubstituted. 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 R is selected from, but not limited to: deuterium atom, cyano group, isocyano group, nitro group or halogen, alkyl group containing 1-20 carbon atoms, heterocyclic group containing 3-20 ring atoms, aromatic group containing 6-20 ring atoms, heteroaromatic group containing 5-20 ring atoms, -NR’R”, silyl group, carbonyl group, alkoxycarbonyl group, aryloxycarbonyl group, carbamoyl group, halocarbonyl group, formyl group, isocyanate group, thiocyanate group, isothiocyanate group, hydroxyl group, trifluoromethyl group, and the above groups can also be further substituted by substituents acceptable in the art; it can be understood that R’ and R” in -NR’R” are each independently selected from, but not limited to: H, deuterium atom, cyano group, isocyano group, nitro group or halogen, alkyl group containing 1-10 carbon atoms, heterocyclic group containing 3-20 ring atoms, aromatic group containing 6-20 ring atoms, heteroaromatic group containing 5-20 ring atoms. Preferably, R is selected from, but not limited to: deuterium atom, cyano group, isocyano group, nitro group or halogen, alkyl group containing 1-10 carbon atoms, heterocyclic group containing 3-10 ring atoms, aromatic group containing 6-20 ring atoms, heteroaromatic group containing 5-20 ring atoms, silyl group, carbonyl group, alkoxycarbonyl group, aryloxycarbonyl group, carbamoyl group, halocarbonyl group, formyl group, isocyanate group, thiocyanate group, isothiocyanate group, hydroxyl group, trifluoromethyl group, and the above groups can also be further substituted by substituents acceptable in the art.

[0046] In the present application, "number of ring atoms" means the number of atoms among the atoms constituting the ring itself in a structural compound obtained by bonding atoms into a ring (for example, monocyclic compound, fused-ring compound, crosslinked compound, carbocyclic compound, heterocyclic compound). When the ring is substituted by a substituent, the atoms contained in the substituent are not included in the ring-forming atoms. The same applies to the "number of ring atoms" described below under the condition of no special description. 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 thiophenyl group is 5.

[0047] In the present application, the "aryl or aromatic group" refers to an aromatic hydrocarbon group derived by removing one hydrogen atom from an aromatic ring compound, which can be a monocyclic aryl group, or a fused-ring aryl group, or a polycyclic aryl group. For the polycyclic rings, at least one is an aromatic ring system. For example, the "substituted or unsubstituted aryl group having 6 to 40 ring atoms" refers to an aryl group containing 6 to 40 ring atoms, preferably a substituted or unsubstituted aryl group having 6 to 30 ring atoms, more preferably a substituted or unsubstituted aryl group having 6 to 18 ring atoms, particularly preferably a substituted or unsubstituted aryl group having 6 to 14 ring atoms, and the aryl group is optionally further substituted; suitable examples include, but are not limited to: phenyl, biphenyl, terphenyl, naphthyl, anthryl, phenanthryl, fluoranthenyl, triphenylenyl, pyrenyl, perylenyl, tetracenyl, fluorenyl, binaphthylenyl, acenaphthylenyl and their derivatives. It can be understood that multiple aryl groups can also be interrupted by short non-aromatic units (e.g., <10% non-H atoms, such as C, N or O atoms), specifically such as acenaphthene, fluorene, or 9,9'-diarylfluorene, triarylamine, diaryl ether systems should also be included in the definition of aryl groups.

[0048] In the present application, the "heteroaryl or heteroaromatic group" refers to a group in which at least one carbon atom in the aryl 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, the "substituted or unsubstituted heteroaryl group having 5 to 40 ring atoms" refers to a heteroaryl group having 5 to 40 ring atoms, preferably a substituted or unsubstituted heteroaryl group having 6 to 30 ring atoms, more preferably a substituted or unsubstituted heteroaryl group having 6 to 18 ring atoms, particularly preferably a substituted or unsubstituted heteroaryl group having 6 to 14 ring atoms, and the heteroaryl group is optionally further substituted. Suitable examples include, but are not limited to: thienyl, furyl, pyrrolyl, imidazolyl, oxazolyl, triazolyl, imidazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, acridinyl, pyridazinyl, pyrazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, benzothienyl, benzofuryl, indolyl, pyrroloimidazolyl, pyrrolopyrrolyl, thienopyrrolyl, thienothienyl, furanopyrrolyl, furanofuryl, thienofuryl, benzisoxazolyl, benzisothiazolyl, benzimidazolyl, quinazolinone, dibenzothienyl, dibenzofuryl, carbazolyl and their derivatives.

[0049] In the present application, the "alkyl group" can represent a straight-chain, branched-chain and / or cyclic alkyl group. The number of carbon atoms in the alkyl group can be 1 to 50, 1 to 30, 1 to 20, 1 to 10 or 1 to 6. A phrase containing this term, for example, "C 1-9"Alkyl" means an alkyl group containing 1 to 9 carbon atoms, and each occurrence can independently be a C1 alkyl group, C2 alkyl group, C3 alkyl group, C4 alkyl group, C5 alkyl group, C6 alkyl group, C7 alkyl group, C8 alkyl group or C9 alkyl group. Non-limiting examples of alkyl groups include methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, tert-butyl, isobutyl, 2-ethylbutyl, 3,3-dimethylbutyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, cyclopentyl, 1-methylpentyl, 3-methylpentyl, 2-ethylpentyl, 4-methyl-2-pentyl, n-hexyl, 1-methylhexyl, 2-ethylhexyl, 2-butylhexyl, cyclohexyl, 4-methylcyclohexyl, 4-tert-butylcyclohexyl, n-heptyl, 1-methylheptyl, 2,2-dimethylheptyl, 2-ethylheptyl, 2-butylheptyl, n-octyl, tert-octyl, 2-ethyloctyl, 2-butyl octyl, 2-hexyloctyl, 3,7-dimethyloctyl, cyclooctyl, n-nonyl, n-decyl, adamantyl, 2-ethyldecyl, 2-butyldecyl, 2-hexyldecyl, 2-octyldecyl, n-undecyl, n-dodecyl, 2-ethyldodecyl, 2-butyldodecyl, 2-hexyldodecyl, 2-octyldodecyl, n-tridecyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, 2-ethylhexadecyl, 2-butyldecyl, 2-hexyldecyl, 2-octyldecyl, n-heptadecyl, n-octadecyl, n-nonadecyl, n-eicosyl, 2-ethyleicosyl, 2-butyleicosyl, 2-hexyleicosyl, 2-octyleicosyl, n-heneicosyl, n-docosyl, n-tricosyl, n-tetracosyl, n-pentacosyl, n-hexacosyl, n-heptacosyl, n-octacosyl, n-nonacosyl, n-triacontyl, etc.

[0050] In the present application, "amino group" refers to a derivative of an amine and has a structural feature of the formula -N(X)2, where each "X" is independently H, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted heterocyclic group, etc. Non-limiting types of amino groups include -NH2, -N(alkyl)2, -NH(alkyl), -N(cycloalkyl)2, -NH(cycloalkyl), -N(heterocyclic group)2, -NH(heterocyclic group), -N(aryl)2, -NH(aryl), -N(alkyl)(aryl), -N(alkyl)(heterocyclic group), -N(cycloalkyl)(heterocyclic group), -N(aryl)(heteroaryl), -N(alkyl)(heteroaryl), etc.

[0051] In the present application, unless otherwise specifically defined, hydroxy refers to -OH, carboxy refers to -COOH, carbonyl refers to -C(=O)-, amino refers to -NH2, formyl refers to -C(=O)H, halocarbonyl refers to -C(=O)Z (where Z represents a halogen), carbamoyl refers to -C(=O)NH2, isocyanate refers to -NCO, and isothiocyanate refers to -NCS.

[0052] In the present application, the term "alkoxy" refers to a group having the structure "-O-alkyl", that is, the alkyl group as defined above is connected to other groups via an oxygen atom. Suitable examples of phrases containing this term include, but are not limited to: methoxy (-O-CH3 or -OMe), ethoxy (-O-CH2CH3 or -OEt), and tert-butoxy (-O-C(CH3)3 or -OtBu).

[0053] In the present application, the "*" connected to a single bond represents a connection or fusion site.

[0054] In the present application, when the connection site of a group is not specified, it means that any optional connection site in the group can be used as the connection site.

[0055] In the present application, when the fusion site of a group is not specified, it means that any optional fusion site in the group can be used as the fusion site. Preferably, two or more sites adjacent to each other in the group are fusion sites.

[0056] In the present application, when there are multiple substituents with the same symbol on the same group, each substituent can be the same or different from each other. For example The six Rs on the benzene ring can be the same or different from each other.

[0057] In the present application, the single bond to which a substituent is attached passes through the corresponding ring, indicating that the substituent can be connected to any position of the ring. For example R in is connected to any substitutable site of the benzene ring; as represents can form a fused ring with any position on the benzene ring in.

[0058] The cyclic alkyl or cycloalkyl as described in the present application has the same meaning and can be interchanged.

[0059] An embodiment of the present application provides an organic compound having a structural formula as shown in formula (I):

[0060]

[0061] Wherein, X is selected from O, S or CR 4 R 5 ;

[0062] R 1 is selected from substituted or unsubstituted alkyl groups having 1 to 5 carbon atoms;

[0063] R 2Selected from hydrogen, deuterium, straight-chain alkyl groups having 1 to 12 carbon atoms, branched-chain alkyl groups having 3 to 12 carbon atoms, cyclic alkyl groups having 3 to 12 carbon atoms, substituted or unsubstituted aromatic groups having 6 to 12 carbon atoms, and substituted or unsubstituted heteroaromatic groups having 5 to 12 carbon atoms;

[0064] R 3 Selected from hydrogen, deuterium, alkyl groups having 1 to 5 carbon atoms, or aryl groups having 6 to 12 carbon atoms;

[0065] R 4 and R 5 Selected from alkyl groups having 1 to 5 carbon atoms or aryl groups having 6 to 12 carbon atoms;

[0066] Ar is selected from substituted or unsubstituted aromatic groups having 6 to 18 carbon atoms, and substituted or unsubstituted heteroaromatic groups having 5 to 18 carbon atoms;

[0067] n1 is selected from any integer from 0 to 4;

[0068] n2 is selected from any integer from 0 to 7;

[0069] n3 is selected from any integer from 0 to 4.

[0070] During the implementation and application process, the molecular structure of the organic compound provided by the embodiments of the present application is composed of an electrophilic hybridized nitrogen atom paired with a substituted or unsubstituted 9-methyl-9-phenylfluorene group and a dibenzofuran / thiophene group, enabling the organic compound to have sufficiently strong hole transport properties and stability. When the organic compound is applied to the light-emitting auxiliary layer, effective exciton blocking can be achieved, inhibiting the reverse transport of excitons, which is beneficial to improving the luminous efficiency and lifespan of the organic electroluminescent device; meanwhile, when isopropyl, tert-butyl, and their deuterated compounds are connected to the 2nd position or the 1st and 3rd positions of the fluorene ring, the steric hindrance provided by the alkane branches affects the stacking of the organic compound, thereby further enhancing the hole transport ability and stability of the organic compound thin film; therefore, it is beneficial to improve the luminous efficiency and service life of the organic electronic device prepared with the organic compound provided by the present application.

[0071] Specifically, in some embodiments, R 1 is selected from alkyl groups having 1 to 5 carbon atoms, or deuterated alkyl groups having 1 to 5 carbon atoms.

[0072] In some embodiments, R 1 is selected from isopropyl, tert-butyl, or -C(CD3)3.

[0073] In some embodiments, R 2 is selected from hydrogen or phenyl.

[0074] In some embodiments, R 3 is selected from hydrogen, deuterium, methyl or phenyl.

[0075] In some embodiments, R 4 and R 5 are selected from methyl or phenyl.

[0076] In some embodiments, Ar is selected from at least one of substituted or unsubstituted phenyl, biphenyl, terphenyl, phenylnaphthyl, dibenzofuranyl, dibenzothiophenyl, 9-phenylcarbazolyl, 9,9-dimethylfluorenyl, 9-methyl-9-phenylfluorenyl, 9,9-diphenylfluorenyl.

[0077] In some embodiments, Ar is selected from phenyl, biphenyl, terphenyl, naphthyl, phenylnaphthyl, dibenzothiophenyl, dibenzofuranyl, dimethylfluorenyl, phenyl-substituted dibenzofuranyl or phenyl-substituted dimethylfluorenyl.

[0078] Further, in some embodiments, the organic compound has a structural formula shown in Formula (1) or Formula (2):

[0079]

[0080] In some embodiments, the organic compound has a structural formula shown in Formula (3), Formula (4), Formula (5) or Formula (6):

[0081]

[0082] In some embodiments, the organic compound is selected from any one of the compounds shown in Formula (1-1) to Formula (1-828) and Formula (2-1) to Formula (2-432):

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[0147] The organic compound provided by the embodiment of the present application can be used as a functional material in the organic functional layer of an electronic device. The organic functional layer includes a hole injection layer (Hole Injection Layer, HIL), a hole transport layer (Hole Transport Layer, HTL), an electron transport layer (Electronic Transport Layer, ETL), an electron injection layer (Electron Injection Layer, EIL), a hole blocking layer (Hole Blocking Layer, HBL), a prime layer, and an emission material layer (Emission Material Layer, EML).

[0148] In some embodiments, the organic compound described in the present application is used in the prime layer.

[0149] Accordingly, the embodiment of the present application further provides a mixture, which includes at least one of the organic compounds described in the above embodiments and at least one organic functional material, and the organic functional material is selected from at least one of a hole injection material, a hole transport material, an electron injection material, an electron transport material, a prime material, a hole blocking material, a guest material, a host material, and an inorganic quantum dot.

[0150] The embodiment of the present application further provides a composition, which includes at least one organic solvent and at least one of the organic compounds, or the composition includes at least one of the organic solvents and the mixture.

[0151] In some embodiments, the organic solvent is selected from at least one of aromatic, heteroaromatic, ester, aromatic ketone, aromatic ether, aliphatic ketone, aliphatic ether, alicyclic, olefinic compounds, borate esters, or phosphate esters.

[0152] In some embodiments, the organic solvent is selected from aromatic or heteroaromatic-based organic solvents.

[0153] Examples of aromatic or heteroaromatic organic solvents suitable for this application include, but are not limited to: p - diisopropylbenzene, pentylbenzene, tetralin, cyclohexylbenzene, chloronaphthalene, 1,4 - dimethylnaphthalene, 3 - isopropylbiphenyl, p - cymene, dipentylbenzene, tripentylbenzene, amyltoluene, 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, benzyl butylbenzene, dimethylnaphthalene, 3 - isopropylbiphenyl, p - cymene, 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, 4-(3 - phenylpropyl)pyridine, benzyl benzoate, 1,1 - bis(3,4 - dimethylphenyl)ethane, 2 - isopropylnaphthalene, quinoline, isoquinoline, methyl 2 - furan - carboxylate, ethyl 2 - furan - carboxylate, etc.

[0154] Examples of aromatic - ketone - based organic solvents suitable for this application include, but are not limited to: 1 - tetralone, 2 - tetralone, 2-(phenyl - epoxy)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.

[0155] Examples of aromatic - ether - based organic solvents suitable for this application include, but are not limited to: 3 - phenoxytoluene, butoxybenzene, dimethyl acetal of p - anisaldehyde, tetrahydro - 2 - phenoxy - 2H - pyran, 1,2 - dimethoxy - 4-(1 - propenyl)benzene, 1,4 - benzodioxane, 1,3 - dipropylbenzene, 2,5 - dimethoxytoluene, 4 - ethylbenzyl methyl 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.

[0156] Examples of aliphatic - ketone - based organic solvents suitable for this application include, but are not limited to: 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 pentyl 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.

[0157] Examples of ester - based organic solvents suitable for this application include, but are not limited to: alkyl octanoates, alkyl sebacates, alkyl stearates, alkyl benzoates, alkyl phenylacetates, alkyl cinnamates, alkyl oxalates, alkyl maleates, alkanolactones, alkyl oleates, etc. Octyl octanoate, diethyl sebacate, diallyl phthalate, and isononyl isononanoate are particularly preferred.

[0158] In some embodiments, the composition further comprises a second organic solvent selected from at least one 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.

[0159] In some embodiments, the organic solvents particularly suitable for this application are solvents with Hansen solubility parameters in the following ranges:

[0160] δ d (Dispersive force) ranges from 17.0 to 23.2 MPa 1 / 2 and especially in the range of 18.5 to 21.0 MPa 1 / 2 ;

[0161] δ p (Polar force) ranges from 0.2 to 12.5 MPa 1 / 2 and especially in the range of 2.0 to 6.0 MPa 1 / 2 ;

[0162] δ h (Hydrogen - bonding force) ranges from 0.9 to 14.2 MPa 1 / 2 and especially in the range of 2.0 to 6.0 MPa 1 / 2 ;

[0163] In the composition provided by the embodiments of the present application, when selecting the organic solvent, its boiling point parameter needs to be considered. In the embodiments of the present application, the boiling point of the organic solvent 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; still more preferably greater than or equal to 250 °C; most preferably greater than or equal to 275 °C or greater than or equal to 300 °C. The boiling points within these ranges are beneficial for preventing nozzle blockage of the inkjet print head. The organic solvent can evaporate from the solvent system to form a thin film containing functional materials.

[0164] In some embodiments, the composition provided by the embodiments of the present application is a solution.

[0165] In a preferred embodiment, the composition provided by the embodiments of the present application is a solution.

[0166] In a preferred embodiment, the composition provided by the embodiments of the present application is a suspension.

[0167] In the embodiments of the present application, the composition may include 0.01 wt% to 20 wt% of the organic compound or the mixture. Further, the organic compound or the mixture in the composition may be 0.1 wt% to 15 wt%. Preferably, the organic compound or the mixture in the composition may be 0.2 wt% to 10 wt%. The present application also relates to the use of the composition as a coating or printing ink in the preparation of organic electronic devices, and particularly preferably the preparation method by printing or coating.

[0168] Among them, suitable printing or coating techniques include (but are not limited to) inkjet printing, nozzle printing, letterpress printing, screen printing, dip coating, spin coating, blade coating, roller printing, reverse roller printing, lithographic printing, flexographic printing, rotary printing, spraying, brushing or pad printing, slot die coating, etc. The preferred ones are gravure printing, nozzle printing and inkjet printing. The solution or suspension may additionally include one or more components such as surface active compounds, lubricants, wetting agents, dispersants, water repellents, adhesives, etc., for adjusting viscosity, improving film-forming properties and enhancing adhesion, etc.

[0169] The present application also provides an organic electronic device 100, which comprises the organic compound described in the above embodiments, the mixture described in the above embodiments or is prepared from the composition described in the above embodiments.

[0170] Please refer to Figure 1, the organic electronic device 100 includes a substrate 1, a first electrode 11, an organic functional layer, and a second electrode 18; the first electrode 11 and the second electrode are disposed opposite to each other, and the organic functional layer is located between the first electrode 11 and the second electrode 18.

[0171] In some embodiments, the material of the organic functional layer includes at least one of the organic compounds described in the above embodiments, or the material of the organic functional layer includes the mixture described in the above embodiments, or the organic functional layer is made of the composition described in the above embodiments.

[0172] In some embodiments, the organic functional layer includes a light-emitting auxiliary layer 14 and a light-emitting layer 15 which are disposed between the first electrode 11 and the second electrode 18 and stacked; the light-emitting auxiliary layer 14 includes a light-emitting auxiliary material, and the light-emitting auxiliary material includes at least one of the organic compounds described in the above embodiments, or the mixture described in the above embodiments, or the composition described in the above embodiments.

[0173] In some embodiments, the organic electronic device 100 includes a substrate 1, a first electrode 11, a hole injection layer 12, a hole transport layer 13, a light-emitting auxiliary layer 14, a light-emitting layer 15, an electron transport layer 16, an electron injection layer 17, and a second electrode 18; that is, the organic functional layer may include a hole injection layer 12, a hole transport layer 13, a light-emitting auxiliary layer 14, a light-emitting layer 15, an electron transport layer 16, and an electron injection layer 17

[0174] In some embodiments, the first electrode 11 may be an anode layer, and the second electrode 18 may be a cathode layer.

[0175] In some embodiments, the organic electronic device 100 includes, but is not limited to, an organic light-emitting diode (OLED), an organic photovoltaic cell (OPV), an organic light-emitting electrochemical cell (OLEEC), an organic field-effect transistor (OFET), an organic light-emitting field-effect transistor (OLEFET), an organic laser, an organic spintronic device, an organic sensor, and an organic plasmon emitting diode, etc. Particularly preferred are organic electroluminescent devices, such as OLED, OLEEC, and OLEFET.

[0176] In the above-mentioned organic electronic device 100, particularly in an OLED, it includes a substrate 1, a first electrode 11, at least one light-emitting layer 15, and a second electrode 18.

[0177] In some embodiments, the substrate 1 can be opaque or transparent. A transparent substrate 1 can be used to fabricate a transparent light-emitting device. For example, see Bulovic et al., Nature 1996, 380, p29, and Gu et al., Appl. Phys. Lett. 1996, 68, p2606. The substrate 1 can be rigid or flexible. The substrate 1 can be plastic, metal, semiconductor wafer, or glass. Preferably, the substrate 1 has a smooth surface. A substrate 1 without surface defects is a particularly ideal choice. In a preferred example, the substrate 1 is flexible and can be selected from polymer films or plastics with a glass transition temperature T g of 150 °C or higher, preferably above 200 °C, more preferably above 250 °C, and most preferably above 300 °C. Examples of suitable flexible substrates include poly(ethylene terephthalate) (PET) and poly(ethylene 2,6-naphthalate) (PEN).

[0178] In some embodiments, the first electrode 11 can include a conductive metal, metal oxide, or conductive polymer. The first electrode 11 can easily inject holes into the HIL, HTL, or EML. In one example, the absolute value of the difference between the work function of the first electrode 11 and the HOMO level or valence band level of the light-emitting body in the light-emitting layer or the p-type semiconductor material serving as the HIL, HTL, or EBL is less than 0.5 eV, preferably less than 0.3 eV, and most preferably less than 0.2 eV. Examples of materials for the first electrode 11 include, but are not limited to: Al, Cu, Au, Ag, Mg, Fe, Co, Ni, Mn, Pd, Pt, ITO, aluminum-doped zinc oxide, etc. Other suitable materials for the first electrode 11 are known and can be easily selected and used by those of ordinary skill in the art. The material of the first electrode 11 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, etc.

[0179] In some embodiments, the first electrode 11 is pattern-structured. Patterned ITO conductive substrates are commercially available and can be used to fabricate the devices according to the present application.

[0180] In some embodiments, the second electrode 18 may include a conductive metal or metal oxide. The second electrode 18 can easily inject electrons into the EIL or ETL or directly into the light-emitting layer. In one embodiment, the absolute value of the difference between the work function of the second electrode 18 and the LUMO energy level or the conduction band energy level of the light-emitting body in the light-emitting layer 15 or the n-type semiconductor material serving as the EIL or ETL or HBL is less than 0.5 eV, preferably less than 0.3 eV, and most preferably less than 0.2 eV. In principle, all materials that can be used as the cathode of the OLED may be used as the material of the second electrode 18 in the organic electronic device of the present application. Examples of the material of the second electrode 18 include, but are not limited to: Al, Au, Ag, Ca, Ba, Mg, LiF / Al, MgAg alloy, BaF2 / Al, Cu, Fe, Co, Ni, Mn, Pd, Pt, ITO, etc. The material of the second electrode 18 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, etc.

[0181] In some embodiments, the light-emitting auxiliary layer 14 in the organic electronic device 100 provided by the embodiments of the present application is prepared using the composition provided in the above embodiments.

[0182] In some embodiments, the light-emitting wavelength of the organic electronic device 100 is between 300 nm and 1000 nm, preferably between 350 nm and 900 nm, and more preferably between 400 nm and 800 nm.

[0183] In some embodiments, the application of the organic electronic device 100 in various electronic devices includes, but is not limited to, display devices, lighting devices, light sources, sensors, and the like.

[0184] In some embodiments, the electronic device including the organic electronic device 100 includes, but is not limited to, display devices, lighting devices, light sources, sensors, and the like.

[0185] The organic compounds provided by the present application will be described below in conjunction with preferred embodiments. However, the organic compounds provided by the present application are not limited to the following embodiments. It should be understood that the appended claims define the scope of the present application. Under the guidance of the concept of the present application, those skilled in the art should realize that certain changes made to the embodiments of the present application will be covered by the spirit and scope of the claims of the present application. Specific Embodiments

[0187] The nitrogen-containing organic compounds of the present application and their preparation methods will be further described in detail below in conjunction with specific embodiments. The raw materials used in the following embodiments are all commercially available products unless otherwise specified.

[0188] Organic Compound Synthesis Examples

[0189] Synthesis of Intermediate 1 to Intermediate 13 involved in Examples 1 to 32

[0190] The synthetic route of Intermediate 1 is as follows:

[0191]

[0192] Weigh reactant A (0.1 mol) and place it in a clean three-necked flask. Add sufficient tetrahydrofuran to dissolve it, and cool it to 0 °C. Under nitrogen protection, slowly add n-butyllithium (0.2 mol), stir evenly and keep for 2 h. After the solution naturally warms up to room temperature, add reactant B (0.2 mol), heat up to 60 °C and reflux for 8 h. After the reaction is completed, add ammonium chloride aqueous solution to quench, extract the organic phase with ethyl acetate to obtain a solid substance, and obtain Intermediate 1 by column chromatography with a yield of 75%. The electrospray ionization mass spectrometry (ESI-MS) result of Intermediate 1: m / z[H + = 333.

[0193] Examples 2 to 13

[0194] Referring to the preparation method of Intermediate 1 in Example 1, select the reactant raw materials shown in Table 1 to prepare Intermediate 2 to Intermediate 13 described in Table 1.

[0195] Table 1 Reactant and product information of Intermediate 2 to Intermediate 13

[0196]

[0197]

[0198] Synthesis of organic compounds in Examples 1 to 32

[0199] The synthetic route of organic compound 1-1 is as follows:

[0200]

[0201] Weigh reactant C (0.1 mol) and reactant D (0.11 mol) and place them in a clean three-necked flask. Add Pd132 (3 mmol), X-Phos (6 mmol), and sodium tert-butoxide (0.2 mol) dissolved in toluene, displace nitrogen three times, and heat up to 110 °C and reflux for 12 h under a nitrogen atmosphere; after natural cooling, wash with water and separate the liquid. Dry the organic phase and then evaporate to dryness, and obtain organic compound 1-1 by column chromatography with a yield of 86%. The m / z[H + = 632.

[0202] Examples 2 to 32

[0203] Referring to the preparation method of organic compound 1-1 in Example 1, the reactant raw materials shown in Table 2 are selected to prepare the organic compounds numbered 1 to 31 described in Table 2.

[0204] Table 2 Information of Reactants and Products in Examples 2 to 32

[0205]

[0206]

[0207]

[0208]

[0209]

[0210] Comparative Examples 1 to 4

[0211] The present application also provides comparative examples, and the organic compounds are correspondingly denoted as "Comparative Compound REF01, Comparative Compound REF02, Comparative Compound REF03, and Comparative Compound REF04", and the chemical structural formulas are as follows:

[0212]

[0213] Preparation and Characterization of OLED Devices

[0214] The organic electronic device 100 provided in the embodiment of the present application can be an OLED device, and taking the preparation of the organic electronic device shown as an example, the preparation method of the OLED device using the organic compound provided in the embodiment of the present application will be described in detail through specific device examples below. Figure 1 Taking the preparation of the organic electronic device shown as an example, the preparation method of the OLED device using the organic compound provided in the embodiment of the present application will be described in detail through specific device examples below.

[0215] In the following preparation method of the OLED device, ITO conductive glass is used as the anode substrate, PD is used as the hole injection material, HT is used as the hole transport material, Host is used as the host material of the light-emitting layer, Dopant is used as the doping material of the light-emitting layer, HB is used as the hole blocking material, ET and Liq are used as the electron transport materials, Liq is used as the electron injection material, and Al is used as the cathode material. In addition, the compound 1-1 of the foregoing synthesis example is used as the light-emitting auxiliary material, and the corresponding OLED devices are prepared respectively. Among them, the chemical structural formulas of PD, HT, Host, Dopant, ET, and Liq are as follows:

[0216]

[0217] The preparation process of the OLED device using the above materials will be described in detail through specific examples below.

[0218] Taking the preparation method of an OLED device using organic compound 1-1 as a light-emitting auxiliary material as an example, the prepared OLED device is denoted as "OLED-1 device". The preparation method of the OLED-1 device includes the following steps:

[0219] Step a: Cleaning of the ITO conductive glass substrate (anode 11). Provide the ITO conductive glass substrate, and ultrasonically clean the substrate with one or more cleaning agents such as deionized water, acetone, isopropanol, or chloroform to improve the work function of the anode 11.

[0220] Step b: Forming a hole injection layer 12 on the anode 11. At a deposition rate of / s, deposit the hole injection materials PD and HT on the anode 11 with a deposition rate ratio of 3:97 to obtain a hole injection layer 12 with a thickness of 30 nm.

[0221] Step c: Forming a hole transport layer 13 on the hole injection layer 12. At a deposition rate of / s, deposit the hole transport material HT on the hole injection layer 12 to obtain a hole transport layer 13 with a thickness of 60 nm.

[0222] Step d: Forming a light-emitting auxiliary layer 14 on the hole transport layer 13. At a deposition rate of / s, deposit compound 1-1 provided in the above embodiment on the hole transport layer 13 to obtain a light-emitting auxiliary layer 14 with a thickness of 10 nm.

[0223] Step e: Forming a light-emitting layer 15 on the light-emitting auxiliary layer 14. At a deposition rate of / s, deposit Host-1, Host-2, and Dopant on the light-emitting auxiliary layer 14, where the ratio of Host-1 to Host-2 is 50:50, and the deposition rate ratio of the double Host to Dopant is 98:2, to obtain a light-emitting layer 15 with a thickness of 40 nm.

[0224] Step f: Forming an electron transport layer 16 on the light-emitting layer 15. In a vacuum chamber, place the electron transport material ET and Liq in different evaporation crucibles, and co-deposit ET and Liq at a weight ratio of 5:5 in a high-vacuum environment (1×10 -6 mbar) to form an electron transport layer 16 with a thickness of 30 nm on the light-emitting layer 15.

[0225] Step g: Forming an electron injection layer 17 on the electron transport layer 16. At a deposition rate of / s, deposit the electron injection material Liq on the electron transport layer 16 to obtain an electron injection layer 17 with a thickness of 1 nm.

[0226] Step h: Forming a cathode 18 on the electron injection layer 17. At a deposition rate of Evaporate the cathode material Al at a deposition rate of / s on the electron injection layer 17 to obtain a cathode 18 with a thickness of 100 nm.

[0227] Step i: Place the device obtained by layer-by-layer deposition in a nitrogen atmosphere glove box and encapsulate it with an ultraviolet curable resin to finally obtain the OLED-1 device.

[0228] In this embodiment, the structure of the prepared device OLED-1 is as follows:

[0229] ITO / PD:HT(3:97, 30 nm) / HT(60 nm) / Organic compound 1-1 provided in this application embodiment (10 nm) / Host-1:Host-2:Dopant (2%, 40 nm) / ET:Liq(5:5, 30 nm) / Liq(1 nm) / Al(100 nm).

[0230] Preparation of OLED-2 to OLED-32 devices

[0231] Referring to the preparation method of the reference device OLED-1, respectively select the organic compounds synthesized in the examples as the light-emitting auxiliary materials of the OLED device, and correspondingly prepare the OLED-2 to OLED-32 devices. It can be understood that in the preparation methods of the above OLED-1 to OLED-32 devices, except for the different light-emitting auxiliary materials, other experimental conditions are the same.

[0232] Furthermore, referring to the preparation method of the reference device embodiment, respectively use the comparative compounds REF01 to REF04 as the light-emitting auxiliary materials, and correspondingly prepare the comparative example OLED-REF01 to OLED-REF04 devices. Compared with the preparation method of the OLED-1 device, in the preparation methods of the OLED-REF01 to OLED-REF04 devices, except for the different light-emitting auxiliary materials, other experimental conditions are the same.

[0233] In this application, the current-voltage (J-V) characteristics of the OLED-1 to OLED-32 and OLED-REF01 to OLED-REF04 devices are characterized, and important parameters such as luminous efficiency and lifetime are recorded at the same time, as shown in Table 3. Among them, the luminous efficiency is the relative value obtained when the current density is 10 mA / cm 2 and the lifetime (LT95) is the time taken for the device brightness to decrease from the initial 1 knit to 95% under a constant current.

[0234] Table 3

[0235]

[0236]

[0237] As can be seen from the results in Table 3, the OLED devices prepared using the organic compounds provided in Examples 1 to 32 of the present application as light-emitting auxiliary materials show excellent effects in terms of voltage, luminous efficiency, and lifespan. This is because when the organic compounds provided in the examples of the present application are applied between the light-emitting layer and the hole-transporting layer, they better improve the hole-transporting property and block excitons compared with the compounds used in the comparative examples. Therefore, when the compounds of the present application are used in the green light-emitting auxiliary layer, the driving voltage, luminous efficiency, and lifespan of the organic electronic device can be improved.

[0238] In addition, the embodiments of the present application also provide a display panel, which includes the organic electronic device described in the above embodiments.

[0239] In summary, the molecular structure of the organic compounds provided in the embodiments of the present application consists of electrophilic hybridized nitrogen atoms combined with substituted or unsubstituted 9-methyl-9-phenylfluorene and dibenzofuran / thiophene, enabling the organic compounds to have strong enough hole-transporting property and stability. When the organic compounds are applied to the green light-emitting auxiliary layer, they can effectively block excitons, inhibit the reverse transport of excitons, and are beneficial to improving the luminous efficiency and lifespan of the organic electroluminescent device. At the same time, when isopropyl, tert-butyl, and their deuterated compounds are connected to the 2nd position or the 1st and 3rd positions of the fluorene ring, the steric hindrance provided by the alkane branches affects the stacking of the organic compounds, thereby further enhancing the hole-transporting ability and stability of the organic compound thin film. Therefore, it is beneficial to improve the luminous efficiency and service life of the organic electronic device prepared using the organic compounds provided in the present application.

[0240] In the description of the present application, the terms "first" and "second" are only used for descriptive purposes and cannot be understood as indicating or implying relative importance or implicitly specifying the quantity of the indicated technical features. Thus, the features defined with "first" and "second" may explicitly or implicitly include one or more features. In the description of the present application, "a plurality" means two or more, unless otherwise specifically defined.

[0241] In the above embodiments, the descriptions of the respective embodiments have their own emphases. For the parts not detailed in a certain embodiment, reference can be made to the relevant descriptions of other embodiments.

[0242] Among the embodiments, embodiments, and related technical features of the present application, they can be combined and replaced with each other without conflict.

[0243] The above are only the preferred embodiments of the present application, and do not impose any formal restrictions on the present application. However, any simple modifications, equivalent changes, and decorations made to the above embodiments based on the technical essence of the present application without departing from the content of the technical solution of the present application still fall within the scope of the technical solution of the present application.

Claims

1. An organic compound, characterized in that, The organic compound has a structural formula as shown in formula (Ⅰ): wherein X is selected from O, S or CR 4 R 5 ; R 1 selected from substituted or unsubstituted alkyl groups having 1 to 5 carbon atoms; R 2 selected from hydrogen, deuterium, straight-chain alkyl groups having 1 to 12 carbon atoms, branched-chain alkyl groups having 3 to 12 carbon atoms, cyclic alkyl groups having 3 to 12 carbon atoms, substituted or unsubstituted aromatic groups having 6 to 12 carbon atoms, and substituted or unsubstituted heteroaromatic groups having 5 to 12 carbon atoms; R 3 selected from hydrogen, deuterium, an alkyl group having 1 to 5 carbon atoms or an aryl group having 6 to 12 carbon atoms; R 4 and R 5 is selected from alkyl groups having 1 to 5 carbon atoms or aryl groups having 6 to 12 carbon atoms; Ar is selected from a substituted or unsubstituted aromatic group having 6 to 18 carbon atoms, a substituted or unsubstituted heteroaromatic group having 5 to 18 carbon atoms; n1 is selected from any integer from 0 to 4; n2 is selected from any integer from 0 to 7; n3 is selected from any integer from 0 to 4.

2. The organic compound according to claim 1, wherein R 1 selected from isopropyl, tert-butyl or -C(CD3)3; R 2 selected from hydrogen or phenyl; R 3 selected from hydrogen, deuterium, methyl or phenyl; R 4 and R 5 is selected from methyl or phenyl.

3. The organic compound according to claim 1, characterized in that, Ar is selected from at least one of a substituted or unsubstituted phenyl group, biphenyl group, terphenyl group, phenylnaphthyl group, dibenzofuranyl group, dibenzothiophenyl group, 9-phenylcarbazolyl group, 9,9-dimethylfluorenyl group, 9-methyl-9-phenylfluorenyl group, 9,9-diphenylfluorenyl group.

4. The organic compound according to any one of claims 1 to 3, characterized in that, The organic compound has a structural formula as shown in formula (1) or formula (2):

5. The organic compound according to any one of claims 1 to 3, characterized in that, The organic compound has a structural formula as shown in formula (3), formula (4), formula (5) or formula (6):

6. A mixture, characterized in that, The mixture includes at least one organic compound as described in any one of claims 1 to 5 and at least one organic functional material, and the organic functional material is selected from at least one of a hole injection material, a hole transport material, an electron injection material, an electron transport material, a light-emitting auxiliary material, a hole blocking material, a guest material, a host material and an inorganic quantum dot.

7. A composition, characterized in that, The composition includes at least one organic solvent and at least one organic compound as described in any one of claims 1 to 5, or the composition includes at least one of the organic solvents and the mixture as described in claim 6.

8. An organic electronic device, characterized in that, The organic electronic device includes: A first electrode; A second electrode, disposed opposite to the first electrode; An organic functional layer, located between the first electrode and the second electrode, and the material of the organic functional layer includes at least one organic compound as described in any one of claims 1 to 5, or the material of the organic functional layer includes the mixture as described in claim 6, or the organic functional layer is made of the composition as described in claim 7.

9. The organic electronic device according to claim 8, wherein The organic functional layer includes a light-emitting auxiliary layer and a light-emitting layer stacked, and the material of the light-emitting auxiliary layer includes at least one of the organic compounds.

10. A display panel, characterized in that, The display panel includes the organic electronic device as described in claim 8 or 9.

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