Aromatic amine organic compounds, mixtures, compositions and organic electronic devices

Abstract

The present application discloses an arylamine organic compound, a mixture, a composition and an organic electronic device comprising the arylamine organic compound, the arylamine organic compound has a structure as shown in general formula (1): the arylamine organic compound is used in an organic electronic device, in particular, as an electron blocking layer material used in an electron blocking layer of an organic electronic device, to improve the efficiency and the life of the organic electronic device.

Description

Technical Field

[0001] This application relates to the field of organic electroluminescence technology, and more particularly to an aromatic amine organic compound, and mixtures, compositions and organic electronic devices comprising said aromatic amine organic compound. Background Technology

[0002] Organic electroluminescence (OEC) refers to the phenomenon of converting electrical energy into light energy using organic materials. OEC display devices are a type of self-emissive display that generate excitons through the transfer and recombination of charge carriers between functional layers, emitting light through high-quantum-efficiency organic compounds or metal complexes. Organic light-emitting diodes (OLEDs) offer advantages such as wide viewing angles, fast response times, low operating voltages, and thin panel thicknesses in optoelectronic applications (e.g., flat panel displays and lighting), thus possessing broad development potential. The structure of an OEC element typically includes a positive electrode, a negative electrode, and organic functional layers in between. To improve the efficiency and lifetime of OEC elements, the organic layers have a multi-layered structure, with each layer containing different organic materials. Specifically, these may include hole injection layers, hole transport layers, light-emitting layers, electron transport layers, and electron injection layers. In this type of organic electroluminescent device, applying a voltage between two electrodes injects holes into the organic layer from the positive electrode and electrons into the organic layer from the negative electrode. When the injected holes and electrons meet, they form excitons, which emit light when they transition back to the ground state. This type of organic electroluminescent device has characteristics such as self-illumination, high brightness, high efficiency, low driving voltage, wide viewing angle, high contrast, and high responsiveness.

[0003] In recent years, the luminous efficiency of organic light-emitting diodes (OLEDs) has been greatly improved, but their internal quantum efficiency has approached the theoretical limit, making further improvement difficult. The difference in the mobility of holes and electrons means that the recombination region cannot be completely uniformly dispersed in the light-emitting layer, reducing the device's luminous efficiency. Improving the material and device structures to reduce the difference in hole and electron mobility and prevent the misalignment of the recombination region, thereby enhancing the device's luminous efficiency and lifetime, has become an important research direction. To improve the efficiency and lifetime of organic light-emitting devices, especially red OLEDs, novel electron blocking layer materials urgently need to be developed. Summary of the Invention

[0004] In view of this, this application provides an aromatic amine organic compound as a novel luminescent material, which is used in organic electronic devices to improve the problems of low luminous efficiency and short lifespan of organic electronic devices.

[0005] The technical solution of this application is as follows:

[0006] An aromatic amine organic compound having the structure shown in general formula (1):

[0007]

[0008] in:

[0009] R1 is selected from substituted or unsubstituted straight-chain alkyl groups having 1 to 20 carbon atoms, or substituted or unsubstituted branched or cyclic alkyl groups having 3 to 20 carbon atoms;

[0010] L1 and L2 are independently selected from single-bonded, substituted or unsubstituted aromatic groups having 6 to 20 ring atoms, or substituted or unsubstituted heteroaromatic groups having 5 to 20 ring atoms.

[0011] Ar1 and Ar2 are independently selected from the structures shown in formulas (A-1), (A-2), (A-3), (A-4), or (A-5);

[0012] Ar3 is independently selected from the structures shown in (A-4) or (A-5);

[0013] Equations (A-1), (A-2), (A-3), (A-4), or (A-5) have the following structural formulas:

[0014]

[0015] Y is selected from O, S, and CR3R4;

[0016] R2 can be monosubstituted or polysubstituted;

[0017] R2, R3, and R4, each time appearing independently, are selected from hydrogen, deuterium, or a straight-chain alkyl group having 1 to 20 carbon atoms, or a branched alkyl group having 3 to 20 carbon atoms, or a cyclic alkyl group having 3 to 20 carbon atoms, or phenyl, or pyridyl, or a combination of these groups;

[0018] * indicates a connection point.

[0019] Accordingly, this application also provides a mixture comprising the above-mentioned aromatic amine organic compounds and at least one organic functional material, 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, luminescent materials, host materials or organic dyes.

[0020] Accordingly, this application also provides a composition comprising the above-mentioned aromatic amine organic compound or mixture thereof, and at least one organic solvent.

[0021] Accordingly, this application also provides an organic electronic device comprising at least one organic functional layer, wherein the organic functional layer contains the above-mentioned aromatic amine organic compounds or mixtures thereof, or the functional layer is prepared from the above-mentioned composition.

[0022] Compared with the prior art, the aromatic amine organic compounds of this application have the following beneficial effects:

[0023] In the aromatic amine organic compounds of this application, R1 is selected from alkyl groups, which reduces the conjugation between the fused ring and the phenyl group, increases the triplet energy level of the molecule, and helps to improve the molecular configuration and stacking mode. This is beneficial to improving the hole transport capability of the electron blocking layer prepared from the aromatic amine organic compounds, thereby achieving a balance between hole transport and electron transport in organic electronic devices, and thus improving the luminous efficiency and lifetime of organic electronic devices. Attached Figure Description

[0024] To more clearly illustrate the technical solutions in the embodiments of this application, the accompanying drawings used in the description of the embodiments will be briefly introduced below. Obviously, the accompanying drawings described below are only some embodiments of this application. For those skilled in the art, other drawings can be obtained based on these drawings without creative effort.

[0025] Figure 1 This is a schematic diagram of the structure of an organic electronic device provided in an embodiment of this application;

[0026] Figure 2 This is the mass spectrum of the organic compound in Example 1 of this application. Detailed Implementation

[0027] The technical solutions in the embodiments of this application will be clearly and completely described below with reference to the accompanying drawings. Obviously, the described embodiments are only some embodiments of this application, and not all embodiments. Based on the embodiments in this application, all other embodiments obtained by those skilled in the art without creative effort are within the scope of protection of this application. In addition, it should be understood that the specific embodiments described herein are only for illustration and explanation of this application and are not intended to limit this application. In this application, unless otherwise stated, directional terms such as "upper" and "lower" generally refer to the upper and lower positions of the device in actual use or operation, specifically the drawing direction in the accompanying drawings. In addition, in the description of this application, the term "comprising" means "including but not limited to", the term "multiple" means "two or more", and the term "and / or" includes any and all combinations of one or more related listed items. Various embodiments of this application may exist in the form of a range; it should be understood that the description in the form of a range is only for convenience and conciseness and should not be construed as a hard limitation on the scope of this application; therefore, it should be considered that the range description has specifically disclosed all possible sub-ranges and single values ​​within that range. For example, it should be assumed that the description of a range from 1 to 6 specifically discloses subranges such as from 1 to 3, from 1 to 4, from 1 to 5, from 2 to 4, from 2 to 6, from 3 to 6, etc., as well as single numbers within the range, such as 1, 2, 3, 4, 5, and 6, regardless of the range. Furthermore, whenever a numerical range is referred to herein, it means including any referenced number (fraction or integer) within the range referred to.

[0028] In this application, the terms "and / or," "or / and," and "and / or" as used include any one of two or more related listed items, as well as any and all combinations of the related listed items. These arbitrary and all combinations include any two related listed items, any more related listed items, or a combination of all related listed items. It should be noted that when at least three items are connected using at least two conjunctions selected from "and / or," "or / and," and "and / or," it should be understood that in this application, the technical solution undoubtedly includes technical solutions connected by "logical AND," and also undoubtedly includes technical solutions connected by "logical OR." For example, "A and / or B" includes three parallel solutions: A, B, and A+B. For example, the technical solution of "A, and / or, B, and / or, C, and / or, D" includes any one of A, B, C, and D (that is, a technical solution that is connected by "logical OR"), as well as any and all combinations of A, B, C, and D, that is, combinations of any two or three of A, B, C, and D, and also combinations of all four of A, B, C, and D (that is, a technical solution that is connected by "logical AND").

[0029] In this application, aromatic groups, aromatic families, and aromatic ring systems have the same meaning and can be used interchangeably.

[0030] In this application, heteroaromatic groups, heteroaromatic families, and heteroaromatic ring systems have the same meaning and can be used interchangeably.

[0031] In this application, "heteroatom" refers to a non-carbon atom, which can be an N atom, an O atom, an S atom, etc.

[0032] In this application, "substitution" means that the hydrogen atom in the substituent is replaced by the substituent.

[0033] In this application, when the same substituent appears multiple times, it can be independently selected from different groups. If the general formula contains multiple R1s, then R1s can be independently selected from different groups.

[0034] In this application, "substituted or unsubstituted" means that the defined group may or may not be substituted. When the defined group is substituted, it should be understood that the defined group can be substituted by one or more substituents R, wherein R is selected from, but is not limited to: deuterium, cyano, isocyano, nitro or halogen, alkyl 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, -NR'R", silyl, carbonyl, alkoxycarbonyl, aryloxycarbonyl, carbamoyl, haloformyl, formyl, isocyanate group, thiocyanate group, isothiocyanate group, hydroxyl, trifluoromethyl, and the above groups may also be further substituted by substituents acceptable in the art; it is understood that R' and R" in -NR'R" are each independently selected from, but not limited to: H, deuterium The group R is selected from, but is not limited to: deuterium, cyano, isocyano, nitro or halogen, alkyl 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 is not limited to: deuterium, cyano, isocyano, nitro or halogen, alkyl 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, carbonyl, alkoxycarbonyl, aryloxycarbonyl, carbamoyl, haloformyl, formyl, isocyanate group, thiocyanate group, isothiocyanate group, hydroxyl, trifluoromethyl, and the above groups may be further substituted with substituents acceptable in the art.

[0035] In this application, "ring atom number" refers to the number of atoms in the ring itself of a structural compound (e.g., a monocyclic compound, a fused-ring compound, a cross-linked compound, a carbocyclic compound, or a heterocyclic compound) obtained by atomic 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-forming atoms. The same applies to the "ring atom number" described below unless otherwise specified. For example, a benzene ring has 6 ring atoms, a naphthalene ring has 10 ring atoms, and a thiophene group has 5 ring atoms.

[0036] In this application, "aryl or aromatic group" refers to an aromatic hydrocarbon group derived from an aromatic ring compound by removing one hydrogen atom. It can be a monocyclic aryl, a fused-ring aryl, or a polycyclic aryl, and for polycyclic rings, at least one of them is an aromatic ring system. For example, "substituted or unsubstituted aryl having 6 to 40 ring atoms" refers to an aryl containing 6 to 40 ring atoms, preferably a substituted or unsubstituted aryl having 6 to 30 ring atoms, more preferably a substituted or unsubstituted aryl having 6 to 18 ring atoms, particularly preferably a substituted or unsubstituted aryl having 6 to 14 ring atoms, and optionally further substituted on the aryl group; suitable examples include, but are not limited to: phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthrene, fluoranyl, triphenylene, pyrene, perylene, tetraphenyl, fluorenyl, dinaphthylphenyl, acenaphthyl, and their derivatives. It is understandable 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 acenaphthene, fluorene, or 9,9-diarylfluorene, triarylamine, and diaryl ether systems should also be included in the definition of aryl.

[0037] In this application, "heteroaryl or heteroaromatic group" refers to an aryl group in which at least one carbon atom is replaced by a non-carbon atom, which can be an N atom, O atom, S atom, etc. For example, "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, and particularly preferably a substituted or unsubstituted heteroaryl group having 6 to 14 ring atoms. The heteroaryl group may optionally be further substituted, and suitable examples include, but are not limited to, thiophene, furanyl, pyrrole, diazolyl, triazolyl, imidazole, pyridyl, bipyridyl, pyrimidinyl, etc. Triazinyl, acridineyl, pyridazinyl, pyrazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, phthalazinyl, pyridinylpyrimidineyl, pyridinylpyrazinyl, benzothiopheneyl, benzofuranyl, indolyl, pyrroloimidazolyl, pyrrolopyrrololyl, thienopyrrololyl, thienopyrrololyl, furanolololyl, furanolofuranyl, thienofuranyl, benzoisoxazolyl, benzoisothiazolyl, benzoimidazolyl, o-diazonyl, phenanthridineyl, primidyl, quinazolinoneyl, dibenzothiopheneyl, dibenzofuranyl, carbazoleyl and their derivatives.

[0038] In this application, "alkyl" can mean straight-chain, branched, and / or cyclic alkyl. The number of carbon atoms in an alkyl group can be 1 to 50, 1 to 30, 1 to 20, 1 to 10, or 1 to 6. Phrases containing this term, such as "C 1-9"Alkyl" refers to an alkyl group containing 1 to 9 carbon atoms, and each time it appears, it can independently be a C1 alkyl, C2 alkyl, C3 alkyl, C4 alkyl, C5 alkyl, C6 alkyl, C7 alkyl, C8 alkyl, or C9 alkyl. 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, etc. tert-amyl, 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-butyloctyl, 2-hexyloctyl The compounds include 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-pentadecanyl, n-hexadecyl, 2-ethylhexadecyl, 2-butylhexadecyl, 2-hexylhexadecyl, 2-octylhexadecyl, n-hepta ...

[0039] In this application, the abbreviations for substituents are: n-n-, sec-sec-, i-iso-, t-tert-, o-ortho-, m-me-, p-para-, Me-methyl, Et-ethyl, Pr-propyl, Bu-butyl, Am-pentyl, Hx-hexyl, Cy-cyclohexyl.

[0040] In this application, "amino group" refers to an amine derivative having the structural feature of the formula -N(X)2, wherein 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)2, -NH(heterocyclic), -N(aryl)2, -NH(aryl), -N(alkyl)(aryl), -N(alkyl)(heterocyclic), -N(cycloalkyl)(heterocyclic), -N(aryl)(heteroaryl), -N(alkyl)(heteroaryl), etc.

[0041] In this application, unless otherwise defined, hydroxyl refers to -OH, carboxyl refers to -COOH, carbonyl refers to -C(=O)-, amino refers to -NH2, formyl refers to -C(=O)H, haloformyl refers to -C(=O)Z (where Z represents halogen), carbamoyl refers to -C(=O)NH2, isocyanate refers to -NCO, and isothiocyanate refers to -NCS.

[0042] In this application, the term "alkoxy" refers to a group with the structure "-O-alkyl", that is, an alkyl group as defined above that is attached 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 (-OC(CH3)3 or -OtBu).

[0043] In this application, the "*" connected to a single bond indicates a connection or fusion site.

[0044] In this application, when no linking site is specified in the group, it means that any linkable site in the group is selected as the linking site.

[0045] In this application, when no fusion site is specified in the group, it means that any fusionable site in the group is selected as the fusion site, preferably two or more sites in the adjacent position of the group are fusion sites.

[0046] In this application, when the same group contains multiple substituents with the same symbol, the substituents can be the same as or different from each other, for example... The six R's on the benzene ring can be the same or different from each other.

[0047] In this application, the single bond connecting the substituents extends through the corresponding ring, indicating that the substituent can be attached to any position on the ring, for example...

[0048] R is attached to any substituted site on the benzene ring, such as... express Can be with The above can be selected at any replaceable position to form a loop.

[0049] In this application, "adjacent groups" means that there are no substituted sites between two substituents.

[0050] In this invention, "two Rs forming a ring" refers to a ring system formed by the interconnection of two Rs. The ring system can be selected from aliphatic hydrocarbon rings, aliphatic heterocycles, aromatic hydrocarbon rings, or aromatic heterocycles. Preferably, it can form an aromatic group or heteroaromatic group with 5-10 substituted or unsubstituted ring atoms; more preferably, it can form...

[0051] In this application, the terms “combinations thereof,” “any combination thereof,” “any combination thereof,” etc., as used, include all suitable combinations of any two or more of the listed items.

[0052] In this application, terms such as "further," "even further," and "particularly" are used to describe purposes and indicate differences in content, but should not be construed as limiting the scope of protection of this application.

[0053] In this application, "optionally," "optionally," and "optional" mean that something is optional, that is, it means that it is selected from either "with" or "without." If there are multiple "optional" entries in a technical solution, unless otherwise specified and there are no contradictions or mutual constraints, each "optional" entry shall be independent.

[0054] In this application, the technical features described in an open-ended manner include both closed technical solutions consisting of the listed features and open technical solutions that include the listed features.

[0055] The technical solution of this application is as follows:

[0056] An aromatic amine organic compound having the structure shown in general formula (1):

[0057]

[0058] in:

[0059] R1 is selected from straight-chain alkyl groups having substituted or unsubstituted 1 to 20 C atoms, or substituted or unsubstituted branched or cyclic alkyl groups having substituted or unsubstituted 3 to 20 C atoms;

[0060] L1 and L2 are independently selected from single-bonded, substituted or unsubstituted aromatic groups having 6 to 20 ring atoms, or substituted or unsubstituted heteroaromatic groups having 5 to 20 ring atoms.

[0061] Ar1 and Ar2 are independently selected from the structures shown in formulas (A-1), (A-2), (A-3), (A-4), or (A-5);

[0062] Ar3 is independently selected from the structures shown in (A-4) or (A-5);

[0063] Among them, Ar1, Ar2, and Ar3 are not simultaneously selected from (A-5);

[0064] Equations (A-1), (A-2), (A-3), (A-4), or (A-5) are shown below:

[0065]

[0066] Y can be selected from O, S, or CR3R4;

[0067] R2 can be monosubstituted or polysubstituted;

[0068] R2, R3, and R4, each appearing independently, are selected from: hydrogen, deuterium (D), or a straight-chain alkyl group having 1 to 20 carbon atoms, or a branched alkyl group having 3 to 20 carbon atoms, or a cyclic alkyl group having 3 to 20 carbon atoms, or phenyl, or pyridyl, or a combination of these groups; * indicates a linking site.

[0069] In one embodiment, R1 is selected from a straight-chain alkyl group having 1 to 10 carbon atoms that is unsubstituted or substituted with one or more D atoms, or a branched or cyclic alkyl group having 3 to 10 carbon atoms that is unsubstituted or substituted with one or more D atoms.

[0070] In one embodiment, R1 is selected from the following structure:

[0071] *— *-CD3

[0072] In this context, * indicates a connection site.

[0073] In one embodiment, R2 is selected from monosubstituted, disubstituted, trisubstituted, or tetrasubstituted groups; "monosubstituted" as used in this invention means that one H atom on the substituted group is replaced by R2; "disubstituted" means that two H atoms on the substituted group are replaced by R2; similarly, "trisubstituted", "tetrasubstituted", and "multisubstituted" are used.

[0074] In one embodiment, R2, R3, and R4 each appear independently selected from: hydrogen, deuterium, or a straight-chain alkyl group having 1 to 10 carbon atoms, or a branched alkyl group having 3 to 10 carbon atoms, or a cyclic alkyl group having 3 to 10 carbon atoms, or phenyl, or pyridyl, or a combination of these groups.

[0075] In one embodiment, the aromatic amine organic compound is selected from any structure shown in formulas (2-1)-(2-4):

[0076]

[0077] In one embodiment, the Ar3 is independently selected from the following groups:

[0078]

[0079] In this context, * indicates a connection site.

[0080] In one embodiment, Ar1 is selected from the structure shown in formula (A-1).

[0081] In one specific embodiment, the aromatic amine organic compound is selected from any structure shown in formulas (3-1)-(3-6):

[0082]

[0083] In one specific embodiment, Ar1 and Ar2 are selected from the following groups:

[0084]

[0085] In one embodiment, L1 and L2 are independently selected from single-bonded, substituted or unsubstituted aromatic groups having 6 to 10 ring atoms, or substituted or unsubstituted heteroaromatic groups having 5 to 10 ring atoms.

[0086] In one embodiment, L1 and L2 are each independently selected from the following groups each time they appear:

[0087]

[0088] in,

[0089] Each time X appears, it is independently selected from CR5 or N;

[0090] Each time W appears, it is independently selected from O, S, CR6R7, or NR8;

[0091] R5, R6, R7, and R8, each appearing independently, are selected from: hydrogen, deuterium, or a straight-chain alkyl group having 1 to 20 carbon atoms, or a straight-chain alkoxy group having 1 to 20 carbon atoms, or a straight-chain thioalkoxy group having 1 to 20 carbon atoms, or a branched alkyl group having 3 to 20 carbon atoms, or a branched alkoxy group having 3 to 20 carbon atoms, or a branched thioalkoxy group having 3 to 20 carbon atoms, or a cyclic alkyl group having 3 to 20 carbon atoms, or a cyclic alkoxy group having 3 to 20 carbon atoms, or a cyclic thioalkoxy group having 3 to 20 carbon atoms, or a silyl group, or a ketone group having 1 to 20 carbon atoms, or a group having 2 to 20 carbon atoms. An alkoxycarbonyl group having 7 to 20 carbon atoms, or an aryloxycarbonyl group having 7 to 20 carbon atoms, a cyano group, a carbamoyl group, a halocarbamoyl group, a formyl group, an isocyano group, an isocyanate group, a thiocyanate group, an isothiocyanate group, a hydroxyl group, a nitro group, an amino group, a -CF3 group, a -Cl group, a -Br group, a -F group, an -I group, or an alkenyl group having 2 to 20 carbon atoms, or an aromatic group having 6 to 60 substituted or unsubstituted ring atoms, or a heteroaromatic group having 5 to 60 substituted or unsubstituted ring atoms, or a heteroaromatic group having 5 to 60 substituted or unsubstituted ring atoms, or a combination of these groups;

[0092] When X is a connection site, X is selected from C; when W is a connection site, W is selected from N.

[0093] In one embodiment, R5, R6, R7, and R8 each appear independently selected from: hydrogen, deuterium, or a straight-chain alkyl group having 1 to 10 carbon atoms, or a branched alkyl group having 3 to 10 carbon atoms, or a cyclic alkyl group having 3 to 10 carbon atoms, or an aromatic group having 6 to 14 substituted or unsubstituted cyclic atoms, or a heteroaromatic group having 5 to 14 substituted or unsubstituted cyclic atoms, or a combination of these groups.

[0094] Furthermore, L1 and L2 are each independently selected from single bonds or the following structures:

[0095]

[0096] In one specific embodiment, L1 and L2 are each independently selected from single bonds or phenyl groups.

[0097] In one embodiment, the molecular structure contains at least one substituted or unsubstituted fluorene group, specifically, at least one of L1, L2, Ar1, Ar2, and Ar3 is selected from substituted or unsubstituted fluorene groups. Further, in the aromatic amine compound, at least one of Ar1, Ar2, and Ar3 is selected from... Preferably, R3 and R4 are independently selected from methyl or phenyl. The fluorene group has good carrier transport capability and can effectively enhance the carrier transport capability of the aromatic amine organic compound.

[0098] As an example, in some embodiments, the aromatic amine organic compounds of this application may be selected from, but are not limited to, any of the following structures:

[0099]

[0100]

[0101]

[0102]

[0103]

[0104]

[0105] It is understandable that the H in the structural formula of the above-mentioned aromatic amine organic compounds can be further substituted.

[0106] In one embodiment, the aromatic amine organic compound according to this application is used in an electron blocking layer. Furthermore, the aromatic amine organic compound according to this application is used in an electron blocking layer of an organic electronic device.

[0107] This application also relates to an electron blocking layer material comprising the aromatic amine organic compounds described above.

[0108] This application further relates to a mixture comprising at least one aromatic amine organic compound as described above and at least one other organic functional material. The other organic functional material may be selected from hole injection materials (HIM), hole transport materials (HTM), electron transport materials (ETM), electron injection materials (EIM), electron blocking materials (EBM), hole blocking materials (HBM), luminescent materials, host materials, or organic dyes. Various organic functional materials are described in detail, for example, in WO2010135519A1, US20090134784A1, and WO2011110277A1, the entire contents of which are hereby incorporated herein by reference.

[0109] In one embodiment, the other organic functional material is selected from electron transport materials and is blended with the aromatic amine organic compounds described in this application as a co-host material for use in organic electronic devices.

[0110] This application also relates to a composition comprising at least one aromatic amine organic compound or mixture as described above, and at least one organic solvent.

[0111] The organic solvent is selected from at least one of aromatic or heteroaromatic solvents, ester-based solvents, aromatic ketone-based solvents, aromatic ether-based solvents, aliphatic ketones, aliphatic ethers, alicyclic compounds, olefin compounds, borate esters, and phosphate esters.

[0112] In at least one embodiment, the organic solvent in the composition is selected from aromatic or heteroaromatic solvents.

[0113] The aromatic or heteroaromatic solvents may be selected from, but are not limited to, p-diisopropylbenzene, pentobenzene, tetrahydronaphthalene, 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-isopropylbenzene. At least one of the following: 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-furanoate, and ethyl 2-furanoate.

[0114] The ester-based solvent may be selected from, but is not limited to, alkyl octanoate, alkyl sebacate, alkyl stearate, alkyl benzoate, alkyl phenylacetate, alkyl cinnamate, alkyl oxalate, alkyl maleate, alkyl lactone, alkyl oleate, etc. At least one of octanoate, diethyl sebacate, diallyl phthalate, and isononyl isononanoate is particularly preferred.

[0115] The aromatic ketone-based solvent may be selected from, but is not limited to, 1-tetrahydronaphthone, 2-tetrahydronaphthone, 2-(phenylepoxy)tetrahydronaphthone, 6-(methoxy)tetrahydronaphthone, acetophenone, phenylacetone, benzophenone, and derivatives thereof. As an example, the derivative may be selected from, but is not limited to, at least one of 4-methylacetophenone, 3-methylacetophenone, 2-methylacetophenone, 4-methylphenylacetone, 3-methylphenylacetone, and 2-methylphenylacetone.

[0116] The aromatic ether-based solvent may be selected from, but is not limited to, at least one of 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-ethylbenzene, 1,3-dipropoxybenzene, 1,2,4-trimethoxybenzene, 4-(1-propenyl)-1,2-dimethoxybenzene, 1,3-dimethoxybenzene, glycidylphenyl ether, dibenzyl ether, 4-tert-butylanisole, trans-p-propenylanisole, 1,2-dimethoxybenzene, 1-methoxynaphthalene, diphenyl ether, 2-phenoxymethyl ether, 2-phenoxytetrahydrofuran, and ethyl-2-naphthyl ether.

[0117] The aliphatic ketone-based solvent may be selected from, but is not limited to, 2-nonanone, 3-nonanone, 5-nonanone, 2-decanone, 2,5-hexanedione, 2,6,8-trimethyl-4-nonanone, frankinc, phorone, isophorone, di-n-pentyl 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, and tetraethylene glycol dimethyl ether.

[0118] It is understood that the organic solvent can be used alone or as a mixture of two or more organic solvents.

[0119] In some embodiments, the composition of this application includes at least one aromatic amine organic compound or mixture as described above, and at least one organic solvent, and may further include another organic solvent.

[0120] The other organic solvent may be selected from, but is not limited to, methanol, ethanol, 2-methoxyethanol, dichloromethane, trichloromethane, 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 (DMSO), tetrahydronaphthalene, naphthane, and indene.

[0121] In some embodiments, suitable organic solvents for this application are solvents with Hansen solubility parameters within the following ranges:

[0122] δd (dispersion force) is in the range of 17.0-23.2 MPa1 / 2, especially in the range of 18.5-21.0 MPa1 / 2;

[0123] δp (polar force) is in the range of 0.2-12.5 MPa1 / 2, especially in the range of 2.0-6.0 MPa1 / 2;

[0124] δh (hydrogen bond strength) is in the range of 0.9-14.2 MPa1 / 2, especially in the range of 2.0-6.0 MPa1 / 2.

[0125] In some embodiments, the boiling point of the organic solvent is taken into consideration when selecting the composition according to this application. In at least some embodiments, the boiling point of the organic solvent is ≥150°C; preferably ≥180°C; more preferably ≥200°C; even more preferably ≥250°C; and most preferably ≥300°C. Boiling points within these ranges are beneficial for preventing nozzle clogging of the inkjet printhead.

[0126] It is understood that the organic solvent can evaporate from the solvent system to form a thin film comprising the organic compound.

[0127] In some embodiments, the composition is a solution. In still other embodiments, the composition is a suspension. The solution or suspension may further include additives for adjusting viscosity, adjusting film-forming properties, improving adhesion, etc. The additives may be selected from, but are not limited to, at least one of surfactants, lubricants, wetting agents, dispersants, hydrophobic agents, and adhesives.

[0128] In the composition, the content of the organic compound or mixture is 0.01-10 wt%, preferably 0.1-5 wt%, more preferably 0.2-5 wt%, and most preferably 0.25-3 wt%.

[0129] This application also relates to the use of the composition as a coating or printing ink in the preparation of organic electronic devices. In some embodiments, the composition is used to prepare organic electronic devices by a printing or coating method. The printing or coating method may include, but is not limited to, inkjet printing, gravure printing, inkjet printing, letterpress printing, screen printing, dip coating, spin coating, doctor blade coating, roller printing, torsional roller printing, offset printing, flexographic printing, rotary printing, spraying, brushing, pad printing, slot extrusion coating, etc. Gravure printing, inkjet printing, and inkjet printing are preferred.

[0130] This application also relates to the use of the aromatic amine organic compound, mixture, or composition as described above in organic electronic devices. Specific details are as follows:

[0131] An organic electronic device includes at least one functional layer. The functional layer comprises at least one aromatic amine organic compound or mixture as described above, or is prepared from the above-described composition.

[0132] The organic electronic devices may be selected from, but are not limited to, organic light-emitting diodes (OLEDs), organic photovoltaic cells (OPVs), organic light-emitting cells (OLEECs), organic field-effect transistors (OFETs), organic light-emitting field-effect transistors, organic lasers, organic spintronic devices, organic sensors, and organic plasmon emitting diodes (OPDs). Organic electroluminescent devices, such as OLEDs, OLEECs, and organic light-emitting field-effect transistors, are particularly preferred. OLEDs are even more particularly preferred.

[0133] Furthermore, the organic electronic device includes a cathode, an anode, and at least one organic functional layer. The organic functional layer comprises at least one aromatic amine organic compound or mixture as described above, or is prepared from the above-described composition.

[0134] The organic functional layer can be, but is not limited to, a hole injection layer (HIL), a hole transport layer (HTL), an emissive layer (EML), an electron blocking layer (EBL), an electron injection layer (EIL), an electron transport layer (ETL), or a hole blocking layer (HBL). Preferably, the organic functional layer is an electron blocking layer.

[0135] In one embodiment, the organic electronic device according to this application includes a cathode, an anode, a light-emitting layer located between the cathode and the anode, and a hole transport region located between the anode and the light-emitting layer. The hole transport region includes a hole transport layer and an electron blocking layer, wherein the hole transport layer is located between the anode and the light-emitting layer, and the electron blocking layer is located between the hole transport layer and the light-emitting layer. The electron blocking layer comprises an aromatic amine organic compound or mixture as described above, or is prepared from the above-described composition.

[0136] In one embodiment, the organic electronic device includes a substrate and an anode, a hole injection layer, a hole transport layer, an electron blocking layer, a light-emitting layer, an electron transport layer, an electron injection layer, and a cathode sequentially stacked on the substrate. The electron blocking layer contains at least one aromatic amine organic compound or mixture as described above, or the electron blocking layer is prepared from the composition described above. It is understood that the structure of the organic electronic device is not limited thereto.

[0137] The substrate may be transparent or opaque. The substrate may be rigid or flexible. The substrate may be plastic, metal, semiconductor wafer, or glass. Preferably, the substrate has a smooth surface; a substrate without surface defects is particularly desirable. In one embodiment, the substrate is flexible, and its material may be selected from, but is not limited to, polymer films or plastics, with a glass transition temperature (Tg) of 150°C or higher, preferably 200°C or higher, more preferably 250°C or higher, and most preferably 300°C or higher. Examples of suitable flexible substrates include polyethylene terephthalate (PET) and polyethylene glycol (2,6-naphthalene) (PEN).

[0138] The anode is the electrode for injecting holes, and the anode can readily inject holes into the hole injection layer, hole transport layer, or light-emitting layer. The anode may comprise a conductive metal, a conductive metal oxide, or a conductive polymer. In one embodiment, the absolute value of the difference between the work function of the anode and the HOMO level or valence band level of the light emitter or p-type semiconductor material serving as a HIL, HTL, or electron blocking layer (EBL) in the light-emitting layer is less than 0.5 eV, preferably less than 0.3 eV, and most preferably less than 0.2 eV. Examples of anode materials include, but are not limited to, Al, Cu, Au, Ag, Mg, Fe, Co, Ni, Mn, Pd, Pt, ITO, aluminum-doped zinc oxide (AZO), etc. Other suitable anode materials are known and can be readily selected by those skilled in the art. The anode material 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 is patterned. Patterned ITO conductive substrates are commercially available and can be used to fabricate the devices according to this application. The cathode is an electron-injecting electrode, and electrons can be readily injected into the electron injection layer, electron transport layer, or light-emitting layer. The cathode may contain a conductive metal or a conductive metal oxide. In one embodiment, the absolute value of the difference between the work function of the cathode and the LUMO level or conduction band level of the light-emitting material in the light-emitting layer or the n-type semiconductor material serving as the electron injection layer (EIL), electron transport layer (ETL), or hole blocking layer (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 suitable for use as cathodes in organic electronic devices can be used as cathode materials for the devices of this application. Examples of cathode materials 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 cathode material 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.

[0139] The hole injection layer is used to facilitate the injection of holes from the anode to the light-emitting layer, and the hole injection material is a material that can readily receive holes injected from the positive electrode at low voltage. Preferably, the highest occupied molecular orbital (HOMO) of the hole injection material is between the work function of the positive electrode material and the HOMO of the surrounding organic material layer. Specific examples of hole injection materials include, but are not limited to, metalloporphyrins, oligothiophenes, arylamine-based organic materials, hexanitrile hexaazabenzophenanthrene-based organic materials, quinacridone-based organic materials, perylene-based organic materials, anthraquinones, conductive polymers based on polyaniline and polythiophene.

[0140] The hole transport layer can be used to efficiently transport holes. Hole transport materials known in the art for use in the hole transport layer are suitably materials with high hole mobility, capable of receiving holes transported from the anode or hole injection layer and transferring the holes to the light-emitting layer. Specific examples include, but are not limited to, arylamine-based organic materials, conductive polymers, block copolymers having both conjugated and non-conjugated portions.

[0141] The light-emitting layer can emit red, green, or blue light and can be composed of phosphorescent or fluorescent materials. The light-emitting material is capable of receiving holes and electrons from the hole transport layer and electron transport layer, respectively, and combining the holes and electrons to emit light in the visible light region, and is preferably a material with good quantum efficiency for fluorescence or phosphorescence. Specific examples include: 8-hydroxyquinoline aluminum complexes (Alq3); carbazole-based compounds; dipolystyrene-based compounds; BAlq; 10-hydroxybenzoquinoline-metal compounds; compounds based on benzoazole, benzothiazole, and benzimidazole; polymers based on poly(p-phenylenevinylene) (PPV); spirocyclic compounds; polyfluorene; fluorene, etc., but are not limited thereto.

[0142] Examples of host materials used for the luminescent layer include fused aromatic ring derivatives or heterocyclic compounds. Specifically, examples of fused aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentane derivatives, phenanthrene compounds, and fluoranthene compounds, while examples of heterocyclic compounds include carbazole derivatives, dibenzofuran derivatives, ladder-type furan compounds, and pyrimidine derivatives, but are not limited to these examples.

[0143] When the emissive layer emits red light, the following can be used as luminescent dopants: phosphorescent materials, such as bis(1-phenylisoquinoline)acetylacetone iridium (PIQIr(acac)), bis(1-phenylquinoline)acetylacetone iridium (PQIr(acac)), tris(1-phenylquinoline)iridium (PQIr), or octaethylporphyrin platinum (PtOEP); or fluorescent materials, such as tris(8-hydroxyquinoline)aluminum (Alq3), but the luminescent dopants are not limited to these. When the emissive layer emits green light, phosphorescent materials such as planar tris(2-phenylpyridine)iridium (Ir(ppy)3) or fluorescent materials such as tris(8-hydroxyquinoline)aluminum (Alq3) can be used as luminescent dopants, but the luminescent dopants are not limited to these. When the luminescent layer emits blue light, the following can be used as luminescent dopants: phosphorescent materials, such as (4,6-F2ppy)2Irpic; or fluorescent materials, such as spiro-DPVBi, spiro-6P, distyrylbenzene (DSB), distyrylaryl (DSA), PFO-based polymers, or PPV-based polymers, but the luminescent dopants are not limited to these.

[0144] In one embodiment, the light-emitting layer material comprises a structure as shown in general formula (4):

[0145]

[0146] in:

[0147] q is selected from 1 or 2;

[0148] Each time Ar7 appears, it is independently selected from substituted or unsubstituted heteroaromatic groups having 5 to 40 ring atoms;

[0149] Each time Ar8 appears, it is independently selected from an aromatic group having 6 to 40 ring atoms, either substituted or unsubstituted, or a heteroaromatic group having 5 to 40 ring atoms.

[0150] R 11 R 12 Each time it appears, it is independently selected from H, D, a straight-chain alkyl group having 1 to 20 carbon atoms, a branched or cyclic alkyl group having 3 to 20 carbon atoms, a substituted or unsubstituted aromatic group having 5 to 60 ring atoms, a substituted or unsubstituted heteroaromatic group having 5 to 60 ring atoms, or a combination of these groups.

[0151] In one embodiment, each occurrence of Ar7 is independently selected from quinoline or isoquinoline and their derivatives. Preferably, when Ar7 occurs multiple times, it is independently selected from quinoline, or isoquinoline, or quinoline substituted with an alkyl group having 1-8 carbon atoms, or isoquinoline substituted with an alkyl group having 1-8 carbon atoms.

[0152] In one embodiment, Ar8 is selected independently from phenyl and its derivatives each time it appears. Preferably, Ar8 is selected independently from phenyl or phenyl substituted with an alkyl group having 1-8 carbon atoms each time it appears.

[0153] In one embodiment, R 11 R 12 Each time it appears, it is independently selected from H, D, straight-chain alkyl with 1 to 10 C atoms, or branched or cyclic alkyl with 3 to 10 C atoms.

[0154] In some embodiments, the general formula (4) is selected from any of the structures shown in general formulas (7-1), (7-2), and (7-3):

[0155]

[0156] in:

[0157] a is selected from 0, 1, 2, 3, 4, 5 or 6, and b is selected from 0, 1, 2, 3 or 4;

[0158] R13 R 14 Each time it appears, it is independently selected from D, a straight-chain alkyl group having 1 to 20 C atoms, a branched or cyclic alkyl group having 3 to 20 C atoms, a substituted or unsubstituted aromatic group having 5 to 60 cyclic atoms, a substituted or unsubstituted heteroaromatic group having 5 to 60 cyclic atoms, or a combination of these groups.

[0159] In one embodiment, at least one R 13 or R 14 It is selected from straight-chain alkyl groups having 1 to 10 carbon atoms, or branched or cyclic alkyl groups having 3 to 10 carbon atoms.

[0160] In one embodiment, at least one R 13 Selected from straight-chain alkyl groups having 1 to 8 carbon atoms, or branched or cyclic alkyl groups having 3 to 8 carbon atoms. Further, at least one R 14 It is selected from straight-chain alkyl groups having 1 to 8 carbon atoms, or branched or cyclic alkyl groups having 3 to 8 carbon atoms.

[0161] According to the metal complex of general formula (4), the preferred structures are those that are not limited to the following, and these structures can be arbitrarily replaced:

[0162]

[0163]

[0164]

[0165] The electron transport layer can be used to efficiently transport electrons. The electron transport material is suitable as a material with high electron mobility, capable of efficiently receiving electrons injected from the negative electrode and transferring them to the light-emitting layer. Specific examples may include, but are not limited to, at least one of: Al complexes of 8-hydroxyquinoline, complexes containing Alq3, organic radical compounds, hydroxyflavonoid-metal complexes, lithium 8-hydroxyquinoline (Liq), and benzimidazole-based compounds.

[0166] The electron injection layer can be used to smoothly inject electrons. The preferred electron injection material has the ability to transport electrons, the effect of injecting electrons from the negative electrode, and an excellent effect of injecting electrons into the light-emitting layer or light-emitting material, preventing excitons generated by the light-emitting layer from migrating to the hole injection layer, and also has excellent thin film formation capabilities. Specific examples include fluorenones, anthraquinone dimethane, biphenylquinone, thiamethane dioxide, azoles, diazoles, triazoles, imidazoles, perylenetetracarboxylic acid, fluorenemethane, anthrones, and their derivatives, metal complex compounds, nitrogen-containing 5-membered ring derivatives, etc., but are not limited to these.

[0167] The hole-blocking layer is a layer that prevents holes from reaching the negative electrode, and it can typically be formed under the same conditions as the hole injection layer. Specific examples include, but are not limited to, diazole or triazole derivatives, phenanthrene-rholine derivatives, BCP, aluminum complexes, etc.

[0168] In one embodiment, the organic electronic device described in this application is a solution-type organic electronic device, wherein one or more functional layers are fabricated by printing; further, the solution-type organic electronic device is a solution-type OLED.

[0169] This application also relates to the application of the organic electronic device according to this application in various electronic devices, which may be, but are not limited to, display devices, lighting devices, light sources, sensors, etc.

[0170] This application also relates to electronic devices that include the aforementioned organic electronic devices. The electronic devices may be, but are not limited to, display devices, lighting devices, light sources, and sensors.

[0171] The present application will be specifically described below through specific embodiments. The following embodiments are only some embodiments of the present application and are not intended to limit the present application. Specific Implementation

[0173] Example 1

[0174] The synthetic route for the aromatic amine organic compound R1 in this embodiment is as follows:

[0175]

[0176] Compound Z1 (3.06 g, 15 mmol), 2-naphthoboric acid (2.58 g, 15 mmol), potassium carbonate (4.14 g, 30 mmol), and tetrakis(triphenylphosphine)palladium (0.52 g, 0.45 mmol) were weighed and added to a two-necked flask. A mixed solvent of toluene and methanol was added, and the mixture was purged with nitrogen three times. The mixture was then heated to 90 °C and stirred overnight. After the reaction solution cooled to room temperature, water was added, and the mixture was extracted with ethyl acetate. The solution was dried over sodium sulfate, and the organic solvent was removed by vacuum distillation. The target compound Z2 was obtained by silica gel column chromatography with stirring, yielding a total of 2.84 g, with a yield of 75%.

[0177] Compounds Z2 (2.52 g, 10 mmol) and Z3 (3.61 g, 10 mmol) were dissolved in anhydrous toluene. Sodium tert-butoxide (1.15 g, 12 mmol) and tris(2,2-benzylacetone) dipalladium (0.27 g, 0.3 mmol) were added. After purging with nitrogen three times, tri-tert-butylphosphine (0.3 mmol) was added. The mixture was gradually heated to 80 °C and stirred for 12 hours. The heat source was then removed. After cooling, deionized water was added, the organic layer was separated, and the mixture was extracted three times with ethyl acetate. The extract was concentrated under reduced pressure and passed through a silica gel column to give 4.15 g of the aromatic amine compound R1, yield 72%, MS = 578 [M]. + ].

[0178] Example 2

[0179] The synthetic route for the aromatic amine organic compound R14 in this embodiment is as follows:

[0180]

[0181] Compound Z4 (10.8 g, 30 mmol), 4-biphenylboronic acid (5.94 g, 30 mmol), potassium carbonate (8.28 g, 60 mmol), and tetrakis(triphenylphosphine)palladium (1.04 g, 0.9 mmol) were weighed and added to a two-necked flask. A mixed solvent of toluene and methanol was added, and the mixture was purged with nitrogen three times. The mixture was then heated to 90 °C and stirred overnight. After the reaction solution cooled to room temperature, water was added, and the mixture was extracted with ethyl acetate. The solution was dried over sodium sulfate, and the organic solvent was removed by vacuum distillation. The solution was then separated by silica gel column chromatography to obtain 7.18 g of the target compound Z5, with a yield of 62%.

[0182] Compound Z5 (5.79 g, 15 mmol) was dissolved in anhydrous tetrahydrofuran, cooled to -78 °C, and butyllithium (1.6 M, 9.3 mL) was slowly added. After about 0.5 hours, a tetrahydrofuran solution of acetone (15 mmol) was added dropwise to the reaction flask, and the reaction was continued at this temperature for another half hour. The temperature was then raised to room temperature, and the reaction was continued for another 8 hours. The solvent was removed under reduced pressure, and hydrochloric acid and acetic acid were added, followed by reflux for about 2 hours. The mixture was cooled to room temperature, and deionized water was added, followed by extraction with ethyl acetate. After concentration, the mixture was separated by silica gel column chromatography, and the solvent was removed to give 3.03 g of compound Z6, with a yield of 58%.

[0183] Compounds Z7 (3.78 g, 15 mmol) and Z8 (2.54 g, 15 mmol) were dissolved in anhydrous toluene. Sodium tert-butoxide (1.73 g, 18 mmol) and tris(dibenzylacetone) dipalladium (0.41 g, 0.45 mmol) were added. After purging with nitrogen three times, tri-tert-butylphosphine (0.45 mmol) was added. The mixture was gradually heated to 80 °C and stirred for 12 hours. The heat source was then removed. After the system cooled, deionized water was added, the organic layer was separated, and the mixture was extracted three times with ethyl acetate. The extract was concentrated under reduced pressure and passed through a silica gel column to give 4.5 g of compound Z9, yield 78%.

[0184] Compounds Z9 (2.7 g, 7 mmol) and Z6 (2.43 g, 7 mmol) were dissolved in anhydrous toluene. Sodium tert-butoxide (0.86 g, 9 mmol) and tris(2,2-benzylacetone) dipalladium (0.19 g, 0.21 mmol) were added. After purging with nitrogen three times, tri-tert-butylphosphine (0.21 mmol) was added. The mixture was gradually heated to 80 °C and stirred for 12 hours. The heat source was then removed. After cooling, deionized water was added, the organic layer was separated, and the mixture was extracted three times with ethyl acetate. The extract was concentrated under reduced pressure and passed through a silica gel column to give 3.24 g of the aromatic amine compound R14, yield 71%, MS = 653 [M]. + ].

[0185] Example 3

[0186] The synthetic route for the aromatic amine organic compound R31 in this embodiment is as follows:

[0187]

[0188] Compound Z1 (4.08 g, 20 mmol), 1-naphthoboric acid (3.44 g, 20 mmol), potassium carbonate (5.52 g, 40 mmol), and tetrakis(triphenylphosphine)palladium (0.69 g, 0.6 mmol) were weighed and added to a two-necked flask. A mixed solvent of toluene and methanol was added, and the mixture was purged with nitrogen three times. The mixture was then heated to 90 °C and stirred overnight. After the reaction solution cooled to room temperature, water was added, and the mixture was extracted with ethyl acetate. The solution was dried over sodium sulfate, and the organic solvent was removed by vacuum distillation. The solution was then separated by silica gel column chromatography to obtain 3.93 g of the target compound Z10, with a yield of 78%.

[0189] Compounds Z10 (3.78 g, 15 mmol) and Z8 (2.54 g, 15 mmol) were dissolved in anhydrous toluene. Sodium tert-butoxide (1.73 g, 18 mmol) and tris(dibenzylacetone) dipalladium (0.41 g, 0.45 mmol) were added. After purging with nitrogen three times, tri-tert-butylphosphine (0.45 mmol) was added. The mixture was gradually heated to 80 °C and stirred for 12 hours. The heat source was then removed. After the system cooled, deionized water was added, the organic layer was separated, and the mixture was extracted three times with ethyl acetate. The extract was concentrated under reduced pressure and passed through a silica gel column to give 4.1 g of compound Z11, with a yield of 71%.

[0190] Compounds Z11 (3.85 g, 10 mmol) and Z12 (3.04 g, 10 mmol) were dissolved in anhydrous toluene. Sodium tert-butoxide (1.15 g, 12 mmol) and tris(dibenzylacetone) dipalladium (0.27 g, 0.3 mmol) were added. After purging with nitrogen three times, tri-tert-butylphosphine (0.3 mmol) was added. The mixture was gradually heated to 80 °C and stirred for 12 hours. The heat source was then removed. After cooling, deionized water was added, the organic layer was separated, and extracted three times with ethyl acetate. The extract was concentrated under reduced pressure and passed through a silica gel column to give 4.96 g of the aromatic amine compound R31, yield 76%, MS = 653 [M]. + ].

[0191] Example 4

[0192] The synthetic route for the aromatic amine organic compound R42 in this embodiment is as follows:

[0193]

[0194] Compound Z1 (2.04 g, 10 mmol), 9,9-dimethyl-2-fluorenboronic acid (2.38 g, 10 mmol), potassium carbonate (2.76 g, 20 mmol), and tetra(triphenylphosphine)palladium (0.35 g, 0.3 mmol) were weighed and added to a two-necked flask. A mixed solvent of toluene and methanol was added, and the mixture was purged with nitrogen three times. The mixture was then heated to 90 °C and stirred overnight. After the reaction solution cooled to room temperature, water was added, and the mixture was extracted with ethyl acetate. The solution was dried over sodium sulfate, and the organic solvent was removed by vacuum distillation. The solution was then separated by silica gel column chromatography to obtain 2.1 g of the target compound Z13, with a yield of 66%.

[0195] Compounds Z13 (1.91 g, 6 mmol) and Z14 (2.44 g, 6 mmol) were dissolved in anhydrous toluene. Sodium tert-butoxide (0.69 g, 7.2 mmol) and tris(dibenzylacetone) dipalladium (0.16 g, 0.18 mmol) were added. After purging with nitrogen three times, tri-tert-butylphosphine (0.18 mmol) was added. The mixture was gradually heated to 80 °C and stirred for 12 hours. The heat source was then removed. After cooling, deionized water was added, the organic layer was separated, and extracted three times with ethyl acetate. The extract was concentrated under reduced pressure and passed through a silica gel column to give 3.31 g of the aromatic amine compound R42, yield 80%, MS = 689 [M]. + ].

[0196] Example 5

[0197] The synthetic route for the aromatic amine organic compound R62 in this embodiment is as follows:

[0198]

[0199] Compound Z1 (2.04 g, 10 mmol), 9,9-dimethyl-3-fluorenboronic acid (2.38 g, 10 mmol), potassium carbonate (2.76 g, 20 mmol), and tetra(triphenylphosphine)palladium (0.35 g, 0.3 mmol) were weighed and added to a two-necked flask. A mixed solvent of toluene and methanol was added, and the mixture was purged with nitrogen three times. The mixture was then heated to 90 °C and stirred overnight. After the reaction solution cooled to room temperature, water was added, and the mixture was extracted with ethyl acetate. The solution was dried over sodium sulfate, and the organic solvent was removed by vacuum distillation. The solution was then separated by silica gel column chromatography to obtain 2.45 g of the target compound Z15, with a yield of 77%.

[0200] Compounds Z15 (2.22 g, 7 mmol) and Z16 (2.25 g, 7 mmol) were dissolved in anhydrous toluene. Sodium tert-butoxide (0.81 g, 8.4 mmol) and tris(dibenzylacetone) dipalladium (0.24 g, 0.21 mmol) were added. After purging with nitrogen three times, tri-tert-butylphosphine (0.21 mmol) was added. The mixture was gradually heated to 80 °C and stirred for 12 hours. The heat source was then removed. After cooling, deionized water was added, the organic layer was separated, and the mixture was extracted three times with ethyl acetate. The extract was concentrated under reduced pressure and passed through a silica gel column to give 3.04 g of the aromatic amine compound R62, yield 72%, MS = 603 [M]. + ].

[0201] Example 6

[0202] The synthetic route for the aromatic amine organic compound R82 in this embodiment is as follows:

[0203]

[0204] Compound Z1 (2.04 g, 10 mmol), diphenylfuran-2-boronic acid (2.12 g, 10 mmol), potassium carbonate (2.76 g, 20 mmol), and tetra(triphenylphosphine)palladium (0.35 g, 0.3 mmol) were weighed and added to a two-necked flask. A mixed solvent of toluene and methanol was added, and the mixture was purged with nitrogen three times. The mixture was then heated to 90 °C and stirred overnight. After the reaction solution cooled to room temperature, water was added, and the mixture was extracted with ethyl acetate. The solution was dried over sodium sulfate, and the organic solvent was removed by vacuum distillation. The solution was then separated by silica gel column chromatography to obtain 2.33 g of the target compound Z17, with a yield of 80%.

[0205] Compounds Z17 (2.33 g, 8 mmol) and Z18 (2.73 g, 8 mmol) were dissolved in anhydrous toluene. Sodium tert-butoxide (0.96 g, 10 mmol) and tris(dibenzylacetone) dipalladium (0.22 g, 0.24 mmol) were added. After purging with nitrogen three times, tri-tert-butylphosphine (0.24 mmol) was added. The mixture was gradually heated to 80 °C and stirred for 12 hours. The heat source was then removed. After cooling, deionized water was added, the organic layer was separated, and the mixture was extracted three times with ethyl acetate. The extract was concentrated under reduced pressure and passed through a silica gel column to give 4.01 g of the aromatic amine compound R82, yield 84%, MS = 597 [M]. + ].

[0206] Example 7

[0207] The synthetic route for the aromatic amine organic compound R98 in this embodiment is as follows:

[0208]

[0209] Compound Z19 (3.7 g, 20 mmol), 2-naphthoboric acid (3.44 g, 20 mmol), potassium carbonate (5.52 g, 40 mmol), and tetrakis(triphenylphosphine)palladium (0.69 g, 0.6 mmol) were weighed and added to a two-necked flask. A mixed solvent of toluene and methanol was added, and the mixture was purged with nitrogen three times. The mixture was then heated to 90 °C and stirred overnight. After the reaction solution cooled to room temperature, water was added, and the mixture was extracted with ethyl acetate. The solution was dried over sodium sulfate, and the organic solvent was removed by vacuum distillation. The target compound Z20 was obtained by silica gel column chromatography with stirring, yielding a total of 2.89 g, with a yield of 62%.

[0210] Compound Z20 (2.8 g, 12 mmol) and 2-bromonaphthalene (2.47 g, 12 mmol) were dissolved in anhydrous toluene. Sodium tert-butoxide (1.44 g, 15 mmol) and tris(dibenzylacetone) dipalladium (0.33 g, 0.36 mmol) were added. After purging with nitrogen three times, tri-tert-butylphosphine (0.36 mmol) was added. The mixture was gradually heated to 80 °C and stirred for 12 hours. The heat source was then removed. After the system cooled, deionized water was added, the organic layer was separated, and the mixture was extracted three times with ethyl acetate. The extract was concentrated under reduced pressure and purified by silica gel column chromatography to give 2.58 g of compound Z21, with a yield of 60%.

[0211] Compounds Z21 (2.51 g, 7 mmol) and Z22 (2.77 g, 7 mmol) were dissolved in anhydrous toluene. Sodium tert-butoxide (0.81 g, 8.4 mmol) and tris(dibenzylacetone) dipalladium (0.19 g, 0.21 mmol) were added. After purging with nitrogen three times, tri-tert-butylphosphine (0.21 mmol) was added. The mixture was gradually heated to 80 °C and stirred for 12 hours. The heat source was then removed. After cooling, deionized water was added, the organic layer was separated, and extracted three times with ethyl acetate. The extract was concentrated under reduced pressure and passed through a silica gel column to give 3.73 g of the aromatic amine compound R98, yield 79%, MS = 675 [M]. + ].

[0212] Example 8

[0213] The synthetic route for the aromatic amine organic compound R131 in this embodiment is as follows:

[0214]

[0215] Compound Z23 (4.64 g, 20 mmol), 9,9-dimethyl-3-fluorenboronic acid (4.76 g, 20 mmol), potassium carbonate (5.52 g, 40 mmol), and tetra(triphenylphosphine)palladium (0.69 g, 0.6 mmol) were weighed and added to a two-necked flask. A mixed solvent of toluene and methanol was added, and the mixture was purged with nitrogen three times. The mixture was then heated to 90 °C and stirred overnight. After the reaction solution cooled to room temperature, water was added, and the mixture was extracted with ethyl acetate. The solution was dried over sodium sulfate, and the organic solvent was removed by vacuum distillation. The solution was then separated by silica gel column chromatography to obtain 5.6 g of the target compound Z24, with a yield of 81%.

[0216] Compound Z24 (5.19 g, 15 mmol) and aniline (1.4 g, 15 mmol) were dissolved in anhydrous toluene. Sodium tert-butoxide (1.73 g, 18 mmol) and tris(dibenzylacetone) dipalladium (0.41 g, 0.45 mmol) were added. After purging with nitrogen three times, tri-tert-butylphosphine (0.45 mmol) was added. The mixture was gradually heated to 80 °C and stirred for 12 hours. The heat source was then removed. After the system cooled, deionized water was added, the organic layer was separated, and the mixture was extracted three times with ethyl acetate. The extract was concentrated under reduced pressure and passed through a silica gel column to give 4.23 g of compound Z25, with a yield of 70%.

[0217] Compounds Z25 (4.03 g, 10 mmol) and Z26 (2.82 g, 10 mmol) were dissolved in anhydrous toluene. Sodium tert-butoxide (1.15 g, 12 mmol) and tris(dibenzylacetone) dipalladium (0.27 g, 0.3 mmol) were added. After purging with nitrogen three times, tri-tert-butylphosphine (0.3 mmol) was added. The mixture was gradually heated to 80 °C and stirred for 12 hours. The heat source was then removed. After cooling, deionized water was added, the organic layer was separated, and extracted three times with ethyl acetate. The extract was concentrated under reduced pressure and passed through a silica gel column to give 3.45 g of the aromatic amine compound R131, yield 57%, MS = 605 [M]. + ].

[0218] Example 9

[0219] The synthetic route for the aromatic amine organic compound R143 in this embodiment is as follows:

[0220]

[0221] Compound Z24 (3.46 g, 10 mmol) and benzidine (1.69 g, 10 mmol) were dissolved in anhydrous toluene. Sodium tert-butoxide (1.15 g, 12 mmol) and tris(2,2-benzylacetone) dipalladium (0.27 g, 0.3 mmol) were added. After purging with nitrogen three times, tri-tert-butylphosphine (0.3 mmol) was added. The mixture was gradually heated to 80 °C and stirred for 12 hours. The heat source was then removed. After the system cooled, deionized water was added, the organic layer was separated, and the mixture was extracted three times with ethyl acetate. The extract was concentrated under reduced pressure and purified by silica gel column chromatography to give 3.02 g of compound Z27, with a yield of 63%.

[0222] Compounds Z27 (2.87 g, 6 mmol) and Z28 (1.69 g, 6 mmol) were dissolved in anhydrous toluene. Sodium tert-butoxide (0.69 g, 7.2 mmol) and tris(dibenzylacetone) dipalladium (0.16 g, 0.18 mmol) were added. After purging with nitrogen three times, tri-tert-butylphosphine (0.18 mmol) was added. The mixture was gradually heated to 80 °C and stirred for 12 hours. The heat source was then removed. After cooling, deionized water was added, the organic layer was separated, and the mixture was extracted three times with ethyl acetate. The extract was concentrated under reduced pressure and passed through a silica gel column to give 3.35 g of the aromatic amine compound R143, yield 82%, MS = 681 [M]. + ].

[0223] Example 10

[0224] The synthetic route for the aromatic amine organic compound R144 in this embodiment is as follows:

[0225]

[0226] Compound Z23 (2.32 g, 10 mmol), dibenzofuran-2-boronic acid (2.28 g, 10 mmol), potassium carbonate (2.76 g, 20 mmol), and tetra(triphenylphosphine)palladium (0.35 g, 0.3 mmol) were weighed and added to a two-necked flask. A mixed solvent of toluene and methanol was added, and the mixture was purged with nitrogen three times. The mixture was then heated to 90 °C and stirred overnight. After the reaction solution cooled to room temperature, water was added, and the mixture was extracted with ethyl acetate. The solution was dried over sodium sulfate, and the organic solvent was removed by vacuum distillation. The target compound Z29 was obtained by silica gel column chromatography with stirring, yielding a total of 2.18 g, with a yield of 65%.

[0227] Compounds Z29 (1.68 g, 5 mmol) and Z30 (2.8 g, 5 mmol) were dissolved in anhydrous toluene. Sodium tert-butoxide (0.58 g, 6 mmol) and tris(dibenzylacetone) dipalladium (0.14 g, 0.15 mmol) were added. After purging with nitrogen three times, tri-tert-butylphosphine (0.15 mmol) was added. The mixture was gradually heated to 80 °C and stirred for 12 hours. The heat source was then removed. After cooling, deionized water was added, the organic layer was separated, and the mixture was extracted three times with ethyl acetate. The extract was concentrated under reduced pressure and purified by silica gel column chromatography to give 2.71 g of the aromatic amine compound R144, yield 82%, MS = 661 [M]. + ].

[0228] Comparative Example 1

[0229] The organic compound in this comparative example is C1, and its chemical structural formula is as follows:

[0230]

[0231] Comparative Example 2

[0232] The organic compound in this comparative example is C2, and its chemical structural formula is as follows:

[0233]

[0234] Fabrication of OLED devices

[0235] In this embodiment, in the OLED device, ITO is used as the anode material, HATCN as the hole injection layer material, HT as the hole transport material, the organic compounds in Examples 1-10 and Comparative Examples 1-2 as the electron blocking layer material, RH as the host material of the light-emitting layer material, RD as the dopant material of the light-emitting layer material, ET and Liq (lithium 8-hydroxyquinoline) as electron transport materials, Liq as the electron injection material, and Al as the cathode material, thus forming the device structure as ITO / HATCN / HT / electron blocking layer material / RH:RD / ET:Liq / Liq / Al.

[0236] A schematic diagram of the OLED device 100 is shown below. Figure 1 As shown in the figure. In this figure, 10 is the substrate, 20 is the anode, 30 is the hole injection layer, 40 is the hole transport layer, 50 is the electron blocking layer, 60 is the light-emitting layer, 70 is the electron transport layer, 80 is the electron injection layer, and 90 is the cathode.

[0237] The chemical structural formulas of HATCN, HT, RH, RD, ET, and Liq are as follows:

[0238]

[0239] The above-mentioned materials HATCN, HT, RH, RD, ET, and Liq are all commercially available, or their synthesis methods are existing technologies.

[0240] The following specific examples illustrate the fabrication process of OLED devices using the above-mentioned materials.

[0241] Device Example 1

[0242] The method for fabricating an OLED device in this embodiment includes the following steps:

[0243] 1) Clean the ITO conductive glass anode layer, then ultrasonically clean it with deionized water, acetone, and isopropanol for 15 minutes, and then treat it in a plasma cleaner for 5 minutes to improve the electrode power function.

[0244] 2) On the ITO anode layer, a hole injection layer material HATCN with a thickness of 5 nm is deposited by vacuum evaporation, and the evaporation rate is [not specified].

[0245] 3) Hole transport material HT is deposited on the hole injection layer by vacuum evaporation, with a thickness of 90nm;

[0246] 4) An aromatic amine organic compound R1, with a thickness of 20 nm, is deposited on the hole transport layer by vacuum evaporation.

[0247] 5) A light-emitting layer is deposited on the electron blocking layer, with RH as the host material and RD as the dopant material. The mass ratio of RD to RH is 2:98, and the thickness is 40 nm.

[0248] 6) Electron transport materials ET and Liq are deposited on the light-emitting layer by vacuum evaporation in a mass ratio of 5:5 and a thickness of 30nm.

[0249] 7) An electron injection layer Liq with a thickness of 2 nm is vacuum-deposited on top of the electron transport layer;

[0250] 8) A cathode Al layer with a thickness of 80 nm is vacuum-deposited on top of the electron injection layer.

[0251] Device Examples 2-10

[0252] The devices are basically the same as in Example 1, except that the electron blocking layer materials in Examples 2-10 are selected from the aromatic amine organic compounds in Examples 2-10, as shown in Table 1.

[0253] Device Comparison Example 1-2

[0254] The devices are basically the same as in Example 1, except that the electron blocking layer materials of Comparative Examples 1-2 are selected from organic compounds C1 and C2 of Comparative Examples 1-2, respectively.

[0255] Performance testing and results

[0256] Please see Figure 2 Mass spectrometry analysis was performed on organic compound R1 from Example 1 to obtain the mass spectrum of organic compound R1.

[0257] The current-voltage (JV) characteristics of the OLED devices in Examples 1-10 and Comparative Examples 1-2 were tested using characterization equipment, and important parameters such as luminous efficiency and lifetime were recorded. Luminous efficiency was defined as a current density of 10 mA / cm². 2 The relative values ​​obtained are used for the lifetime (LT95@1000nits), which refers to the time it takes for the device's brightness to decrease from an initial brightness of 1000 nits to 95% of the initial brightness under constant current. The luminous efficiency and lifetime of the OLED devices in Device Examples 1-10 and Device Comparative Example 2 are relative values ​​to the OLED device in Device Comparative Example 1. The test results are shown in Table 1 below.

[0258] Table 1:

[0259] OLED devices Electron blocking layer material Luminous efficiency (relative value) Lifespan (relative value) Device Example 1 R1 1.17 1.23 Device Example 2 R14 1.16 1.27 Device Example 3 R31 1.14 1.16 Device Example 4 R42 1.25 1.28 Device Example 5 R62 1.23 1.29 Device Example 6 R82 1.25 1.20 Device Example 7 R98 1.15 1.18 Device Example 8 R131 1.21 1.18 Device Example 9 R143 1.19 1.21 Device Example 10 R144 1.22 1.20 Device Comparison Example 1 C1 1 1 Device Comparison Example 2 C2 1.04 1.06

[0260] As shown in Table 1, compared with the OLED devices in Comparative Examples 1-2, the OLED devices in Examples 1-10 of this application have higher efficiency and longer lifespan. This demonstrates that the aromatic amine organic compounds of this application, as electron blocking materials, can effectively improve the luminous efficiency and lifespan of organic electroluminescent devices.

[0261] The organic compound C1 in Comparative Example 1 has excessive steric hindrance and relatively weak transport capability.

[0262] In Comparative Example 2, carbazole in the organic compound C2 has a certain electron-donating ability and high conjugation, which affects the molecular energy level.

[0263] The aromatic amine organic compounds of this application contain alkyl groups, which reduces the conjugation between the fused ring and the phenyl group, resulting in a higher triplet energy level of the molecule. This also helps to improve the molecular configuration and stacking mode, thereby enhancing the hole transport capability of the aromatic amine organic compounds and thus improving the luminous efficiency and lifetime of organic electronic devices.

[0264] The above provides a detailed description of the aromatic amine organic compounds, mixtures, compositions, and organic electronic devices provided in the embodiments of this application. Specific examples have been used to illustrate the principles and implementation methods of this application. The descriptions of the above embodiments are only for the purpose of helping to understand the methods and core ideas of this application. At the same time, for those skilled in the art, there will be changes in the specific implementation methods and application scope based on the ideas of this application. Therefore, the content of this specification should not be construed as a limitation of this application.

Claims

1. An arylamine-based organic compound, characterized by, The arylamine organic compound is an electron blocking layer material and has a structure as shown in general formula (1): （1） wherein: R1is selected from or ; L1, L2are independently selected from a single bond, , or ; Ar1, Ar2 are independently selected from structures as shown in formula (A-1), (A-4) or (A-5); when Ar1, Ar2 are selected from formula (A-4), Y is selected from CR3R4; Ar3 is independently selected from structures as shown in (A-4) or (A-5); when Ar3 is selected from formula (A-4), Y is selected from O, S, CR3R4; The formula (A-1), (A-4) or (A-5) respectively has the following structural formula: ； at least one of Ar1, Ar2and Ar3is selected from , and Ar1and Ar2are not simultaneously selected from ; R2 is mono-substituted or poly-substituted; R2is, at each occurrence, independently selected from hydrogen, , or phenyl; R3, R4are independently at each occurrence selected from or phenyl; represents a connection site.

2. The arylamine organic compound according to claim 1, wherein Ar1, Ar2 are selected from the following groups: 。 3. An organic compound of the arylamine class, characterized in that, The arylamine organic compound is an electron blocking layer material, and the arylamine organic compound is selected from the following structures: 。 4. A mixture characterized in that, The mixture comprises the arylamine organic compound according to any one of claims 1-2 and at least one organic functional material, or the mixture comprises at least one arylamine organic compound according to claim 3 and at least one organic functional material; the organic functional material is selected from a hole injection material, a hole transport material, an electron transport material, an electron injection material, an electron blocking material, a hole blocking material, a host material or an organic dye.

5. A composition characterized in that, The composition comprises the arylamine organic compound according to any one of claims 1-2 or the mixture according to claim 4, and at least one organic solvent; or the composition comprises at least one arylamine organic compound according to claim 3 and at least one organic solvent.

6. An organic electronic device comprising at least one organic functional layer, characterized in that The organic functional layer comprises an electron blocking layer, and the electron blocking layer comprises the arylamine organic compound according to any one of claims 1-2, or the electron blocking layer comprises at least one arylamine organic compound according to claim 3.

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