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

Abstract

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

Description

Technical Field

[0001] The present application relates to the technical field of organic electroluminescence, and particularly relates to an aromatic amine organic compound, a mixture, a composition, and an organic electronic device including the aromatic amine organic compound. Background Art

[0002] An organic electroluminescent display device is a self-luminous display device that generates excitons through the transfer and recombination of carriers between functional layers and emits light by relying on organic compounds or metal complexes with high quantum efficiency. The structure of an organic electroluminescent device generally includes a cathode, an anode, and organic functional layers therebetween. To improve the efficiency and lifespan of an organic electroluminescent device, the organic functional layers have a multi-layer structure, and each layer contains different organic substances. Specifically, it may include a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, etc. In such an organic electroluminescent device, when a voltage is applied between the two electrodes, holes are injected from the anode into the organic functional layer, and electrons are injected from the cathode into the organic functional layer. When the injected holes and electrons meet in the light-emitting layer, excitons are formed, and light is emitted when the excitons transition back to the ground state. Such an organic electroluminescent device has characteristics such as self-luminescence, high brightness, high efficiency, low driving voltage, wide viewing angle, and high contrast.

[0003] In addition to the light-emitting layer, an organic electroluminescent device also requires functional layers involved in hole transport such as a hole transport layer and an electron blocking layer to achieve the balanced transport of holes and electrons and the recombination of holes and electrons in the light-emitting layer, so as to improve the efficiency and lifespan of the device. To achieve a highly efficient organic electroluminescent device, in addition to developing high-performance light-emitting layer materials, the development of corresponding hole transport region materials such as electron blocking layer materials is also very important. Therefore, how to design new materials with better performance to make the device perform better has always been an urgent problem for those skilled in the art. Summary of the Invention

[0004] In view of this, the present application provides an aromatic amine organic compound. As a new type of light-emitting material, when it is used in an organic electronic device, it aims to improve the problems of low luminous efficiency and short lifespan of the organic electronic device.

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

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

[0007]

[0008] Wherein:

[0009] Ar 1 、Ar 2 、Ar3 、Ar 4 is independently selected from a substituted or unsubstituted aromatic group having 6 to 30 ring atoms, or a substituted or unsubstituted heteroaromatic group having 5 to 30 ring atoms;

[0010] L 1 、L 2 、L 3 、L 4 is independently selected from a single bond, or a substituted or unsubstituted aromatic group having 6 to 30 ring atoms, or a substituted or unsubstituted heteroaromatic group having 5 to 30 ring atoms;

[0011] R 1 、R 2 、R 3 is independently selected from hydrogen, deuterium, or a straight-chain alkyl group having 1 to 20 C atoms, or a branched-chain alkyl group having 3 to 20 C atoms, or an alkenyl group having 2 to 20 C atoms, or a cyclic alkyl group having 3 to 20 C atoms, or a substituted or unsubstituted aromatic group having 6 to 30 ring atoms, or a substituted or unsubstituted heteroaromatic group having 5 to 30 ring atoms, or a combination of these groups;

[0012] R 4 、R 5 、R 6 is independently selected from hydrogen, deuterium, or a straight-chain alkyl group having 1 to 20 C atoms, or a straight-chain alkoxy group having 1 to 20 C atoms, or a straight-chain thioalkoxy group having 1 to 20 C atoms, or a branched-chain alkyl group having 3 to 20 C atoms, or a branched-chain alkoxy group having 3 to 20 C atoms, or a branched-chain thioalkoxy group having 3 to 20 C atoms, or a cyclic alkyl group having 3 to 20 C atoms, or a cyclic alkoxy group having 3 to 20 C atoms, or a cyclic thioalkoxy group having 3 to 20 C atoms, or a silyl group, or a keto group having 1 to 20 C atoms, or an alkoxycarbonyl group having 2 to 20 C atoms, or an aryloxycarbonyl group having 7 to 20 C atoms, cyano, carbamoyl, halocarbonyl, formyl, isocyano, isocyanate, thiocyanate, isothiocyanate, hydroxy, nitro, amino, -CF 3 、-Cl, -Br, -F, -I, or an alkenyl group having 2 to 20 C atoms, or a substituted or unsubstituted aromatic group having 6 to 60 ring atoms, or a substituted or unsubstituted heteroaromatic group having 5 to 60 ring atoms, or a substituted or unsubstituted aryloxy group having 6 to 60 ring atoms, or a substituted or unsubstituted heteroaryloxy group having 5 to 60 ring atoms, or a combination of these groups;

[0013] Two adjacent Rs 4 either form a ring or do not form a ring with each other; Two adjacent Rs 5Ring-formed or not ring-formed with each other; two adjacent Rs 6 Ring-formed or not ring-formed with each other;

[0014] m1 is selected from 0, 1, 2 or 3; m2 is selected from 0, 1, 2, 3 or 4; m3 is selected from 0, 1, 2 or 3.

[0015] Correspondingly, the present application also provides a mixture, including the above-mentioned aromatic amine organic compound and at least one organic functional material, and 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 light-emitting material, a host material or an organic dye.

[0016] Correspondingly, the present application also provides a composition, including the above-mentioned aromatic amine organic compound or the above-mentioned mixture, and at least one organic solvent.

[0017] Correspondingly, the present application also provides an organic electronic device, including at least one organic functional layer, and the above-mentioned aromatic amine organic compound or the above-mentioned mixture is included in the organic functional layer, or the organic functional layer is prepared from the above-mentioned composition.

[0018] Compared with the prior art, the aromatic amine organic compound of the present application has the following beneficial effects:

[0019] There are 2 aromatic amine structures in the aromatic amine organic compound of the present application, which can effectively improve the carrier transport ability of the amine organic compound molecule, realize the balance between hole transport and electron transport in the organic electronic device, and thus improve the light-emitting efficiency and lifespan of the device. In addition, in the aromatic amine organic compound of the present application, since two fluorene groups are connected by sp3 hybridized carbon atoms, the conjugation degree between the bis(arylamine) can be reduced, the triplet energy level of the organic compound molecule can be increased, and the exciton diffusion of the light-emitting layer can be avoided. Description of the Drawings

[0020] In order 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, other drawings can be obtained based on these drawings without creative efforts.

[0021] Figure 1 is a schematic structural diagram of an organic electronic device provided by an embodiment of the present application;

[0022] Figure 2 is a mass spectrum of the aromatic amine organic compound in Example 1 of the present application. Detailed Embodiments

[0023] The following will clearly and completely describe the technical solutions in the embodiments of the present application with reference to 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 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" generally refer to the upper and lower in the actual use or working state of the device, specifically the drawing direction in the accompanying drawings. In addition, in the description of the present application, the term "including" means "including but not limited to", the term "a plurality of" means "two or more", and the term "and / or" includes any and all combinations of one or more of the related listed items. The various embodiments of the present 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 brevity, and should not be construed as a rigid limitation on the scope of the present application; therefore, it should be considered that the described range description has specifically disclosed all possible sub-ranges and single values within that range. For example, it should be considered that the range description from 1 to 6 has specifically disclosed sub-ranges 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., and single numbers within that range, such as 1, 2, 3, 4, 5, and 6, regardless of the range. In addition, whenever a numerical range is indicated herein, it means including any cited number (fraction or integer) within the indicated range.

[0024] In the present application, the selection range of the terms "and / or", "or / and", and "and / or" includes any one of two or more related listed items, and also includes any and all combinations of the related listed items. The said any and all combinations include combinations of any two related listed items, any more related listed items, or all related listed items. It should be noted that when at least two conjunctions selected from "and / or", "or / and", and "and / or" are used to connect at least three items, it should be understood that in the present application, this technical solution undoubtedly includes the technical solution connected by "logical AND", and also undoubtedly includes the technical solution connected by "logical OR". For example, "A and / or B" includes three parallel solutions: A, B, and A + B. Another example is the technical solution of "A, and / or, B, and / or, C, and / or, D", which includes any one of A, B, C, and D (that is, the technical solution connected by "logical OR"), and also includes any and all combinations of A, B, C, and D, that is, it includes combinations of any two or any three of A, B, C, and D, and also includes the combination of the four items A, B, C, and D (that is, the technical solution connected by "logical AND").

[0025] In the present application, the aromatic group, aromatic, and aromatic ring system have the same meaning and can be used interchangeably.

[0026] In the present application, the heteroaromatic group, heteroaromatic, and heteroaromatic ring system have the same meaning and can be used interchangeably.

[0027] In the present application, a "heteroatom" is a non-carbon atom and can be an N atom, an O atom, an S atom, etc.

[0028] In the present application, "substituted" means that a hydrogen atom in the substituent is replaced by a substituent.

[0029] 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 1 , then R 1 can be independently selected from different groups.

[0030] 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 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 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 in -NR’R”, R’ and R” are independently selected from but not limited to: H, deuterium atom, cyano group, isocyano group, nitro group or halogen, alkyl group containing 1-10 C 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 C 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.

[0031] In the present application, "the number of ring atoms" refers to the number of atoms among the atoms constituting the ring itself in a structural compound obtained by bonding atoms into a ring (for example, a monocyclic compound, a fused-ring compound, a crosslinked compound, a carbocyclic compound, a heterocyclic compound). When the ring is substituted with 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 in a benzene ring is 6, the number of ring atoms in a naphthalene ring is 10, and the number of ring atoms in a thienyl group is 5.

[0032] In the present application, "aryl or aromatic group" refers to an aromatic hydrocarbon group derived by removing one hydrogen atom from an aromatic ring compound, and can be a monocyclic aryl group, a fused-ring aryl group, or a polycyclic aryl group. Among the polycyclic rings, at least one is an aromatic ring system. For example, "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 (for example, <10% of 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.

[0033] In the present application, "heteroaryl or heteroaromatic group" means that 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, "substituted or unsubstituted heteroaryl having 5 to 40 ring atoms" means a heteroaryl having 5 to 40 ring atoms, preferably a substituted or unsubstituted heteroaryl having 6 to 30 ring atoms, more preferably a substituted or unsubstituted heteroaryl having 6 to 18 ring atoms, particularly preferably a substituted or unsubstituted heteroaryl having 6 to 14 ring atoms, and the heteroaryl is optionally further substituted. Suitable examples include, but are not limited to: thienyl, furyl, pyrrolyl, dioxazolyl, 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, phthalazinyl, phenanthridinyl, peridinyl, quinazolinone, dibenzothienyl, dibenzofuryl, carbazolyl and its derivatives.

[0034] In the present application, "alkyl" may represent straight-chain, branched-chain and / or cyclic alkyl. The number of carbon atoms in the alkyl 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 containing 1 to 9 carbon atoms, and each occurrence can independently be C 1 alkyl, C 2 alkyl, C 3 alkyl, C 4 alkyl, C 5 alkyl, C 6 alkyl, C 7 alkyl, C 8 alkyl or C 9Alkyl. Non-limiting examples of alkyl include methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, t-butyl, isobutyl, 2-ethylbutyl, 3,3-dimethylbutyl, n-pentyl, isopentyl, neopentyl, t-pentyl, cyclopentyl, 1-methylpentyl, 3-methylpentyl, 2-ethylpentyl, 4-methyl-2-pentyl, n-hexyl, 1-methylhexyl, 2-ethylhexyl, 2-butylhexyl, cyclohexyl, 4-methylcyclohexyl, 4-t-butylcyclohexyl, n-heptyl, 1-methylheptyl, 2,2-dimethylheptyl, 2-ethylheptyl, 2-butylheptyl, n-octyl, t-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, and the like.

[0035] In this application, the substituent abbreviations correspond to: n-normal, sec-secondary, i-iso, t-tertiary, o-ortho, m-meta, p-para, Me-methyl, Et-ethyl, Pr-propyl, Bu-butyl, Am-n-pentyl, Hx-hexyl, Cy-cyclohexyl.

[0036] In this application, "amino group" refers to a derivative of amine, having the structural feature of the formula -N(X) 2 , where each "X" is independently H, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted heterocyclic group, etc. Non-limiting types of amino groups include -NH 2 , -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.

[0037] In this application, unless otherwise specifically defined, hydroxyl refers to -OH, carboxyl refers to -COOH, carbonyl refers to -C(=O)-, and amino refers to -NH 2 , formyl refers to -C(=O)H, halocarbonyl refers to -C(=O)Z (where Z represents a halogen), and carbamoyl refers to -C(=O)NH 2 , isocyanate refers to -NCO, and isothiocyanate refers to -NCS.

[0038] In this application, the term "alkoxy" refers to a group having the structure "-O-alkyl", that is, the alkyl group defined as above is connected to other groups via an oxygen atom. For phrases containing this term, suitable examples include, but are not limited to: methoxy (-O-CH 3 or -OMe), ethoxy (-O-CH 2 CH 3 or -OEt), and tert-butoxy (-O-C(CH 3 ) 3 or -OtBu).

[0039] In this application, "*" connected to a single bond represents a connection or fusion site.

[0040] In this application, when the connection site is not specified in a group, it means that any optional connection site in the group can be used as the connection site.

[0041] In this application, when the fusion site is not specified in a group, 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 used as the fusion site.

[0042] In this application, when a group contains multiple substituents with the same symbol, each substituent can be the same as or different from each other. For example the 6 Rs on the benzene ring can be the same as or different from each other.

[0043] In this 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 in R is connected to any substitutable site of the benzene ring, such as indicating can form a fused ring with any optional substitutable position on.

[0044] In this application, "adjacent groups" means that there is no substitutable site between two substituents.

[0045] In this application, "any combination thereof", "any combination of them", "any combination mode thereof", etc. include all suitable combination modes of any two or more of the listed items.

[0046] In this application, terms such as "further", "furthermore", "especially", etc. are used for descriptive purposes, indicating differences in content, but should not be construed as limiting the scope of protection of this application.

[0047] In this application, "optionally", "optional", "option" mean either present or absent, that is, either one of two alternative schemes of "present" or "absent". If "optional" appears multiple times in a technical solution, without special instructions and without contradictions or mutual constraints, each "optional" is independent.

[0048] In this application, "two adjacent Rs form a ring with each other" means a ring system formed by connecting two adjacent Rs, and the ring system can be selected from an aliphatic hydrocarbon ring, an aliphatic heterocyclic ring, an aromatic hydrocarbon ring or an aromatic heterocyclic ring. Here, R can be R 4 、R 5 or R 6 。Preferably, the ring system is selected from aromatic groups or heteroaromatic groups having 5 - 10 ring atoms; more preferably, the ring system is selected from aromatic groups or heteroaromatic groups having 6 ring atoms; specifically, the ring system is selected from substituted or unsubstituted phenyl groups.

[0049] In this application, among 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.

[0050] The technical solution of this application is as follows:

[0051] An aromatic amine organic compound having a structure shown in general formula (1):

[0052]

[0053] Wherein:

[0054] Ar 1 、Ar 2 、Ar 3 、Ar 4 are independently selected from substituted or unsubstituted aromatic groups having 6 to 30 ring atoms, or substituted or unsubstituted heteroaromatic groups having 5 to 30 ring atoms;

[0055] L 1 、L 2 、L 3 、L 4 are independently selected from a single bond, or substituted or unsubstituted aromatic groups having 6 to 30 ring atoms, or substituted or unsubstituted heteroaromatic groups having 5 to 30 ring atoms;

[0056] R 1 、R 2 、R3 Independently selected from: hydrogen, deuterium (D), or a straight-chain alkyl group having 1 to 20 C atoms, or a branched alkyl group having 3 to 20 C atoms, or an alkenyl group having 2 to 20 C atoms, or a cyclic alkyl group having 3 to 20 C atoms, or a substituted or unsubstituted aromatic group having 6 to 30 ring atoms, or a substituted or unsubstituted heteroaromatic group having 5 to 30 ring atoms, or a combination of these groups;

[0057] R 4 、R 5 、R 6 Independently selected from: hydrogen, deuterium, or a straight-chain alkyl group having 1 to 20 C atoms, or a straight-chain alkoxy group having 1 to 20 C atoms, or a straight-chain thioalkoxy group having 1 to 20 C atoms, or a branched alkyl group having 3 to 20 C atoms, or a branched alkoxy group having 3 to 20 C atoms, or a branched thioalkoxy group having 3 to 20 C atoms, or a cyclic alkyl group having 3 to 20 C atoms, or a cyclic alkoxy group having 3 to 20 C atoms, or a cyclic thioalkoxy group having 3 to 20 C atoms, or a silyl group, or a keto group having 1 to 20 C atoms, or an alkoxycarbonyl group having 2 to 20 C atoms, or an aryloxycarbonyl group having 7 to 20 C atoms, cyano, carbamoyl, halocarbonyl, formyl, isocyano, isocyanate, thiocyanate, isothiocyanate, hydroxy, nitro, amino, -CF 3 、-Cl, -Br, -F, -I, or an alkenyl group having 2 to 20 C atoms, or a substituted or unsubstituted aromatic group having 6 to 60 ring atoms, or a substituted or unsubstituted heteroaromatic group having 5 to 60 ring atoms, or a substituted or unsubstituted aryloxy group having 6 to 60 ring atoms, or a substituted or unsubstituted heteroaryloxy group having 5 to 60 ring atoms, or a combination of these groups;

[0058] Two adjacent R 4 Either form a ring or do not form a ring with each other; two adjacent R 5 Either form a ring or do not form a ring with each other; two adjacent R 6 Either form a ring or do not form a ring with each other;

[0059] m1 is selected from 0, 1, 2 or 3; m2 is selected from 0, 1, 2, 3 or 4; m3 is selected from 0, 1, 2 or 3.

[0060] In one embodiment, the aromatic amine organic compound is selected from the structures shown in formula (2-1), (2-2) or (2-3):

[0061]

[0062] In one embodiment, the arylamine organic compound is selected from the structures represented by formula (3-1), (3-2) or (3-3):

[0063]

[0064] In one embodiment, R 1 、R 2 、R 3 are independently selected from: hydrogen, deuterium, a straight-chain alkyl group having 1 to 10 C atoms, or a branched alkyl group having 3 to 10 C atoms, a cyclic alkyl group having 3 to 10 C atoms, a substituted or unsubstituted aromatic group having 6 to 14 ring atoms, or a substituted or unsubstituted heteroaromatic group having 6 to 14 ring atoms, or a combination of these groups.

[0065] In a specific embodiment, R 1 、R 2 、R 3 are independently selected from: hydrogen, deuterium, methyl, ethyl, isopropyl, tert-butyl, phenyl, biphenyl, phenyl substituted with an alkyl group having 1 to 10 C atoms, or biphenyl substituted with an alkyl group having 1 to 10 C atoms.

[0066] In a specific embodiment, R 1 and R 2 are selected from the same group; further, R 1 and R 2 are both selected from methyl or phenyl.

[0067] In another embodiment, R 1 and R 2 are selected from different groups; further, R 1 and R 2 are respectively selected from phenyl or methyl.

[0068] In a specific embodiment, R 3 is selected from methyl or phenyl; further, R 3 is selected from methyl.

[0069] In one embodiment, R 4 、R 5 、R 6 are independently selected from: hydrogen, deuterium, or a straight-chain alkyl group having 1 to 10 C atoms, or a branched alkyl group having 3 to 10 C atoms, or a cyclic alkyl group having 3 to 10 C atoms, or a silyl group, a cyano group, an isocyano group, a nitro group, an amino group, -CF 3 、-Cl、-Br、-F、-I、or an alkenyl group having 2 to 20 C atoms, or a substituted or unsubstituted aromatic group having 6 to 30 ring atoms, or a substituted or unsubstituted heteroaromatic group having 5 to 30 ring atoms, or a combination of these groups; two adjacent R4 Either forming a ring or not; two adjacent Rs 5 Either forming a ring or not; two adjacent Rs 6 Either forming a ring or not.

[0070] In one embodiment, R 4 , R 5 , R 6 are independently selected from: hydrogen, deuterium, or a straight-chain alkyl group having 1 to 7 C atoms, or a branched-chain alkyl group having 3 to 7 C atoms, or a cyclic alkyl group having 3 to 7 C atoms, or a substituted or unsubstituted aromatic group having 6 to 14 ring atoms, or a substituted or unsubstituted heteroaromatic group having 6 to 14 ring atoms, or a combination of these groups.

[0071] In a specific embodiment, R 4 , R 5 , R 6 are selected from hydrogen, deuterium, methyl, ethyl, isopropyl, tert-butyl, phenyl, phenyl substituted with an alkyl group having 1 - 10 C atoms; further, R 4 , R 5 , R 6 are selected from methyl, tert-butyl or phenyl.

[0072] In one embodiment, m1 is selected from 0 or 1.

[0073] In one embodiment, m1 is selected from 0.

[0074] In another embodiment, m1 is selected from 1; specifically, as in the above general formulas (1), (2-1), (2-2), (2-3), (3-1), (3-2) and (3-3) selected from wherein, * represents the connection site.

[0075] In one embodiment, m2 is selected from 0 or 1.

[0076] In one embodiment, m2 is selected from 0.

[0077] In another embodiment, m2 is selected from 1; specifically, as in the above general formulas (1), (2-1), (2-2), (2-3), (3-1), (3-2) and (3-3) selected from selected from wherein, * represents the connection site.

[0078] In one embodiment, m3 is selected from 0 or 1.

[0079] In one embodiment, m3 is selected from 0.

[0080] In another embodiment; m3 is selected from 1; specifically, in the general formulas (1), (2-1), (2-2), (2-3), (3-1), (3-2), and (3-3) above selected from wherein, * represents a connecting site.

[0081] In one embodiment, L 1 、L 2 、L 3 、L 4 are independently selected from a single bond, or a substituted or unsubstituted aromatic group having 6 to 20 ring atoms, or a substituted or unsubstituted heteroaromatic group having 6 to 20 ring atoms; further, L 1 、L 2 、L 3 、L 4 are independently selected from a single bond, or a substituted or unsubstituted aromatic group having 6 to 13 ring atoms or a substituted or unsubstituted heteroaromatic group having 6 to 13 ring atoms; further, L 1 、L 2 、L 3 、L 4 are independently selected from a single bond, or a substituted or unsubstituted aromatic group having 6 to 10 ring atoms, or a substituted or unsubstituted heteroaromatic group having 6 to 10 ring atoms.

[0082] In a specific embodiment, L 1 、L 2 、L 3 、L 4 are independently selected from a single bond, phenyl, biphenyl, naphthyl, or phenyl substituted with an alkyl group having 1 to 6 carbon atoms, or biphenyl substituted with an alkyl group having 1 to 6 carbon atoms, or naphthyl substituted with an alkyl group having 1 to 6 carbon atoms.

[0083] In a certain specific embodiment, L 1 、L 2 、L 3 、L 4 are independently selected from a single bond or phenyl. Further, L 1 、L 2 、L 3 、L 4 are all selected from a single bond.

[0084] In one embodiment, Ar 1 、Ar 2 、Ar 3 、Ar 4 are independently selected from a substituted or unsubstituted aromatic group having 6 to 20 ring atoms, or a substituted or unsubstituted heteroaromatic group having 6 to 20 ring atoms; further, Ar 1 、Ar2 、Ar 3 、Ar 4 independently selected from substituted or unsubstituted aromatic groups having 6 to 14 ring atoms, or substituted or unsubstituted heteroaromatic groups having 6 to 14 ring atoms.

[0085] In a specific embodiment, Ar 1 、Ar 2 、Ar 3 、Ar 4 independently selected from one or a combination of the following structures:

[0086]

[0087] wherein,

[0088] each occurrence of X is independently selected from CR 7 or N;

[0089] each occurrence of Y is independently selected from NR 8 、CR 9 R 10 、O or S;

[0090] R 7 、R 8 、R 9 、R 10 each occurrence is independently selected from: hydrogen, deuterium, or a straight-chain alkyl group having 1 to 20 C atoms, or a branched-chain alkyl group having 3 to 20 C atoms, or an alkenyl group having 2 to 20 C atoms, a cyclic alkyl group having 3 to 20 C atoms, or a substituted or unsubstituted aromatic group having 6 to 30 ring atoms, or a substituted or unsubstituted heteroaromatic group having 5 to 30 ring atoms, or a combination of these groups;

[0091] When X is a connection site, X is selected from C atoms; when Y is a connection site, Y is selected from N atoms.

[0092] In one embodiment, Ar 1 、Ar 2 、Ar 3 、Ar 4 independently selected from one or a combination of the following structures:

[0093]

[0094] In a specific embodiment, R 7Each occurrence is independently selected from: hydrogen, deuterium, or a straight-chain alkyl group having 1 to 10 carbon atoms, or a branched-chain alkyl group having 3 to 10 carbon atoms, a cyclic alkyl group having 3 to 10 carbon atoms, or a substituted or unsubstituted aromatic group having 6 to 10 ring atoms, or a substituted or unsubstituted heteroaromatic group having 6 to 10 ring atoms, or a combination of these groups.

[0095] In a specific embodiment, R 7 Each occurrence is independently selected from: hydrogen, deuterium, or a straight-chain alkyl group having 1 to 6 carbon atoms, or a branched-chain alkyl group having 3 to 6 carbon atoms, a cyclic alkyl group having 3 to 6 carbon atoms, or phenyl, biphenyl, naphthyl, or phenyl substituted with an alkyl group having 1 to 6 carbon atoms, or biphenyl substituted with an alkyl group having 1 to 6 carbon atoms, or naphthyl substituted with an alkyl group having 1 to 6 carbon atoms.

[0096] In a certain specific embodiment, the is selected from the following groups:

[0097]

[0098]

[0099] Wherein: the above groups can be further substituted.

[0100] As an example, in some embodiments, the organic compounds of the present application can be selected from, but not limited to, any one of the following structures:

[0101]

[0102]

[0103]

[0104]

[0105] It can be understood that the H in the structural formula of the above arylamine organic compound can be further substituted.

[0106] In one embodiment, the arylamine organic compound according to the present application is used in an electron blocking layer. Further, the arylamine organic compound according to the present application is used in the electron blocking layer of an organic electronic device.

[0107] The present application also relates to an electron blocking layer material comprising the arylamine organic compound as described above.

[0108] The present application further relates to a mixture comprising at least one of the above-mentioned aromatic amine organic compounds and at least one other organic functional material. The other organic functional material may be selected from a hole injection material (HIM), a hole transport material (HTM), an electron transport material (ETM), an electron injection material (EIM), an electron blocking material (EBM), a hole blocking material (HBM), a light-emitting material (Emitter), a host material (Host), or an organic dye. For example, various organic functional materials are described in detail in WO2010135519A1, US20090134784A1, and WO2011110277A1, and the entire contents of these 3 patent documents are hereby incorporated herein by reference.

[0109] In one embodiment, the other organic functional material is an electron transport material, which is blended with the aromatic amine organic compound described in the present application and used as a co-host material in an organic electronic device.

[0110] The present application also relates to a composition comprising at least one of the above-mentioned aromatic amine organic compounds or mixtures, and at least one organic solvent.

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

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

[0113] The aromatic or heteroaromatic-based solvents may be selected from, but are not limited to, p-diisopropylbenzene, pentylbenzene, tetralin, cyclohexylbenzene, chloronaphthalene, 1,4-dimethylnaphthalene, 3-isopropylbiphenyl, p-methylcumene, 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, benzylbutylbenzene, dimethylnaphthalene, 3-isopropylbiphenyl, p-methylcumene, 1-methylnaphthalene, 1,2,4-trichlorobenzene, 4,4-difluorodiphenylmethane, 1,2-dimethoxy-4-(1-propenyl)benzene, diphenylmethane, 2-phenylpyridine, 3-phenylpyridine, N-methyldiphenylamine, 4-isopropylbiphenyl, α,α-dichlorodiphenylmethane, 4-(3-phenylpropyl)pyridine, benzyl benzoate, 1,1-bis(3,4-dimethylphenyl)ethane, 2-isopropylnaphthalene, quinoline, isoquinoline, methyl 2-furoate, and ethyl 2-furoate.

[0114] The ester-based solvent may be selected from, but not limited to, alkyl octanoates, alkyl sebacates, alkyl stearates, alkyl benzoates, alkyl phenylacetates, alkyl cinnamates, alkyl oxalates, alkyl maleates, alkanolactones, alkyl oleates, etc. At least one of octyl octanoate, diethyl sebacate, diallyl phthalate, and isononyl isononanoate is particularly preferred.

[0115] The aromatic ketone-based solvent may be selected from, but not limited to, 1-tetralone, 2-tetralone, 2-(phenyloxiranyl)tetralone, 6-(methoxy)tetralone, acetophenone, propiophenone, benzophenone, and their derivatives. Among them, as an example, the derivatives may be selected from, but not limited to, at least one of 4-methylacetophenone, 3-methylacetophenone, 2-methylacetophenone, 4-methylpropiophenone, 3-methylpropiophenone, and 2-methylpropiophenone.

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

[0117] The aliphatic ketone-based solvent may be selected from, but 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-pentyl ketone, etc.; or aliphatic ethers, for example, at least one of 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 can be understood that the organic solvent can be used alone or as a mixed solvent of two or more organic solvents.

[0119] In some embodiments, the composition of the present application includes at least one of the aromatic amine-based organic compounds or mixtures 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 not limited to, 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 (DMSO), tetralin, decalin, and indene.

[0121] In some embodiments, the organic solvent suitable for the present application is a solvent with Hansen solubility parameters in 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 force) 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, for the composition according to the present application, the boiling point of the organic solvent needs to be considered when selecting. In at least some embodiments, the boiling point of the organic solvent is ≥150 °C; preferably ≥180 °C; more preferably ≥200 °C; still more preferably ≥250 °C; most preferably ≥300 °C. Boiling points within these ranges are beneficial for preventing nozzle clogging of the inkjet print head.

[0126] It can be understood that the organic solvent can evaporate from the solvent system to form a thin film including 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 additionally include additives for adjusting viscosity, adjusting film-forming properties, improving adhesion, etc. The additives may be selected from, but not limited to, at least one of surface active compounds, lubricants, wetting agents, dispersants, water repellents, 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] The present 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 preparation method of printing or coating. The preparation method of printing or coating may be, but is not limited to, inkjet printing, gravure printing, spraying, letterpress printing, screen printing, dip coating, spin coating, blade coating, roller printing, reverse roller printing, lithographic printing, flexographic printing, rotary printing, spraying, brush coating, pad printing, slot die coating, etc. Preferred are gravure printing, spraying and inkjet printing.

[0130] The present application also relates to the application of an arylamine organic compound, mixture or composition as described above in an organic electronic device. The specific solutions are as follows:

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

[0132] The organic electronic device may be selected from, but is not limited to, organic light emitting diodes (OLEDs), organic photovoltaic cells (OPVs), organic light emitting electrochemical 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, etc. Particularly preferred are organic electroluminescent devices, such as OLEDs, OLEECs, and organic light emitting field effect transistors. Further particularly preferred is OLED.

[0133] Further, the organic electronic device includes a cathode, an anode, and at least one organic functional layer. The organic functional layer contains at least one arylamine organic compound or mixture as described above, or is prepared from the above composition.

[0134] The functional layer may be, but is not limited to, a hole injection layer (HIL), a hole transport layer (HTL), a light emitting 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 functional layer is an electron blocking layer.

[0135] In one embodiment, the organic electronic device according to the present invention 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. Among them, the electron blocking layer contains an arylamine organic compound or mixture as described above, or is prepared from the above 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 that are sequentially stacked on the substrate. The electron blocking layer contains at least one of the organic compounds or mixtures described above, or the electron blocking layer is prepared from the composition described above. It can be understood that the structure of the organic electronic device is not limited thereto.

[0137] The substrate can be transparent or opaque. The substrate can be rigid or flexible. The substrate can be plastic, metal, semiconductor wafer, or glass. Preferably, the substrate has a smooth surface, and a substrate without surface defects is a particularly ideal choice. In one embodiment, the substrate is flexible, and its material can be selected from, but not limited to, polymer films or plastics, and its glass transition temperature Tg is above 150 °C, 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).

[0138] The anode is a hole-injecting electrode, and the anode can easily inject holes into the hole injection layer, or the hole transport layer, or the 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 in the light-emitting layer or the p-type semiconductor material serving as the HIL or HTL or electron blocking layer (EBL) 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 those of ordinary skill in the art can easily select and use them. 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 pattern-structured. Patterned ITO conductive substrates are commercially available and can be used to fabricate the devices according to the present application. The cathode is an electron-injecting electrode, and the cathode can easily inject electrons into the electron injection layer, or the electron transport layer, or the light-emitting layer. The cathode may comprise 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 emitter in the light-emitting layer or the n-type semiconductor material serving as the electron injection layer (EIL) or 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 that can be used as the cathode of an organic electronic device may be used as the cathode material of the devices according to the present application. Examples of cathode materials include but are not limited to: Al, Au, Ag, Ca, Ba, Mg, LiF / Al, MgAg alloy, BaF 2 / 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 a layer for facilitating the injection of holes from the anode into the light-emitting layer, and the hole injection material is a material that can proficiently receive holes injected from the positive electrode at a low voltage, and 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 metal porphyrins, oligothiophenes, arylamine-based organic materials, hexanitrile hexaazatriphenylene-based organic materials, quinacridone-based organic materials, perylene-based organic materials, anthraquinone, polyaniline-based and polythiophene-based conductive polymers, etc., but are not limited thereto.

[0140] The hole transport layer can be used to smoothly transport holes. The hole transport materials known in the art for the hole transport layer are preferably materials having a high hole mobility, which can receive holes transported from the anode or the hole injection layer and transfer the holes to the light-emitting layer. Specific examples thereof include arylamine-based organic materials, carbazole-based organic materials, conductive polymers, block copolymers having both a conjugated portion and a non-conjugated portion, etc., but are not limited thereto.

[0141] The light-emitting layer can emit red, green, or blue light and can be composed of a phosphorescent material or a fluorescent material. The light-emitting material is a material that can receive holes and electrons from the hole transport layer and the electron transport layer, respectively, and combine the holes and electrons to emit light in the visible light region, and is preferably a material having good quantum efficiency for fluorescence or phosphorescence. Specific examples thereof include tris(8-hydroxyquinoline)aluminum(Alq3); carbazole-based compounds; distyrylbenzene compounds; BAlq; 10-hydroxybenzoquinoline-metal compounds; benzoxazole-based, benzothiazole-based, and benzimidazole-based compounds; poly(p-phenylenevinylene)(PPV)-based polymers; spiro compounds; polyfluorene; rubrene, etc., but are not limited thereto.

[0142] Examples of the host material for the light-emitting layer include fused aromatic ring derivatives or heterocyclic-containing compounds, etc. Specifically, examples of the fused aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, etc., and examples of the heterocyclic-containing compounds include carbazole derivatives, dibenzofuran derivatives, ladder-type furan compounds, pyrimidine derivatives, etc., but the examples are not limited thereto.

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

[0144] In a specific embodiment, the light-emitting layer material comprises a structure represented by the general formula (4):

[0145]

[0146] Wherein:

[0147] q is independently selected from 1 or 2;

[0148] Ar 5 Each occurrence is independently selected from substituted or unsubstituted heteroaromatic groups having 5 to 40 ring atoms;

[0149] Ar 6 Each occurrence is independently selected from substituted or unsubstituted aromatic groups having 6 to 40 ring atoms, or substituted or unsubstituted heteroaromatic groups having 5 to 40 ring atoms;

[0150] R 11 and R 12 Each occurrence is independently selected from H, D, straight-chain alkyl groups having 1 to 20 C atoms, branched or cyclic alkyl groups having 3 to 20 C atoms, substituted or unsubstituted aromatic groups having 5 to 60 ring atoms, substituted or unsubstituted heteroaromatic groups having 5 to 60 ring atoms, or combinations of these groups.

[0151] In one embodiment, Ar 5 Each occurrence is independently selected from quinoline or isoquinoline and their derivatives. Preferably, Ar 5 Each occurrence is independently selected from quinolinyl, or isoquinolinyl, or quinolinyl substituted with an alkyl group having 1-8 C atoms, or isoquinolinyl substituted with an alkyl group having 1-8 C atoms.

[0152] In one embodiment, Ar 6 Each occurrence is independently selected from phenyl and its derivatives. Preferably, Ar 6 Each occurrence is independently selected from phenyl, or phenyl substituted with an alkyl group having 1-8 C atoms.

[0153] In one embodiment, R 11 and R 12 Each occurrence is independently selected from H, D, straight-chain alkyl groups having 1 to 10 C atoms, or branched or cyclic alkyl groups having 3 to 10 C atoms.

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

[0155]

[0156] Wherein:

[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] R 13 and R 14 each time it appears, 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 aryl group having 5 to 60 ring atoms, a substituted or unsubstituted heteroaryl group having 5 to 60 ring atoms, or a combination of these groups.

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

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

[0161] The metal complex according to the general formula (4) is preferably, but not limited to, the following structures, and these structures can be arbitrarily substituted:

[0162]

[0163]

[0164] The electron transport layer can be used to smoothly transport electrons. The electron transport material is preferably a material with high electron mobility, which can proficiently receive electrons injected from the negative electrode and transfer the electrons to the light-emitting layer. Specific examples thereof may include, but are not limited to: at least one of an Al complex of 8-hydroxyquinoline, a complex containing Alq3, an organic radical compound, a hydroxyflavone-metal complex, lithium 8-hydroxyquinolate (LiQ), and a benzimidazole-based compound.

[0165] The electron injection layer can be used to inject electrons smoothly. The electron injection material is preferably: capable of transporting electrons, having the effect of injecting electrons from the negative electrode, and having an excellent effect of injecting electrons into the light-emitting layer or the light-emitting material, preventing excitons generated by the light-emitting layer from moving to the hole injection layer, and also having an excellent ability to form a thin film. Specific examples thereof include fluorenone, anthraquinodimethane, biphenylquinone, thiopyran dioxide, oxazole, dioxazole, triazole, imidazole, perylene tetracarboxylic acid, fluoreneylidene methane, anthrone, etc. and their derivatives, metal complex compounds, nitrogen-containing 5-membered ring derivatives, etc., but are not limited thereto.

[0166] The hole blocking layer is a layer that blocks holes from reaching the negative electrode, and can generally be formed under the same conditions as those of the hole injection layer. Specific examples thereof include dioxazole derivatives or triazole derivatives, phenanthroline derivatives, BCP, aluminum complexes, etc., but are not limited thereto.

[0167] In one embodiment, the organic electronic device described in the present application is a solution-type organic electronic device, and one or more functional layers thereof are prepared by a printing method; further, the solution-type organic electronic device is a solution-type OLED.

[0168] The present application also relates to the application of the organic electronic device according to the present application in various electronic devices, and the electronic devices can be, but are not limited to, display devices, lighting devices, light sources, sensors, etc.

[0169] The present application also relates to an electronic device including the organic electronic device. The electronic devices can be, but are not limited to, display devices, lighting devices, light sources, and sensors, etc.

[0170] The present application will be specifically described below through specific examples. The following examples are only partial examples of the present application and do not limit the present application. Specific Embodiment

[0172] Example 1

[0173] The synthesis route of the aromatic amine organic compound R1 in this example is as follows:

[0174]

[0175] Dissolve compound Z1 (10.64 g, 40 mmol) in anhydrous tetrahydrofuran, cool to -78 °C, and slowly add butyl lithium (1.6 M, 25 mL). After about 0.5 hours, add a tetrahydrofuran solution of compound Z2 (40 mmol) to the reaction flask, continue to react at this temperature for half an hour, then warm to room temperature and continue to react for 8 hours. Remove the solvent under reduced pressure, add hydrochloric acid and acetic acid, and reflux for about 2 hours. Cool to room temperature, add deionized water, and then extract with ethyl acetate. After concentration, separate through a silica gel column, remove the solvent to obtain a total of 11.66 g of compound Z3, with a yield of 59%.

[0176] Weigh compound Z3 (9.88 g, 20 mmol), o-chlorophenylboronic acid (3.12 g, 20 mmol), potassium carbonate (5.52 g, 40 mmol), tetrakis(triphenylphosphine)palladium (0.69 g, 0.6 mmol) into a two-necked flask, add a mixed solvent of toluene and methanol, replace nitrogen three times, heat to 90°C, and stir overnight. After the reaction solution is cooled to room temperature, water is added, and it is extracted with ethyl acetate, dried with sodium sulfate, and the organic solvent is removed by vacuum distillation. The target product compound Z4 is separated by silica gel column chromatography to obtain 5.35 g of the total, with a yield of 56%.

[0177] Dissolve compound Z4 (4.78 g, 10 mmol) in anhydrous tetrahydrofuran, cool to -78 °C, and slowly add butyl lithium (1.6 M, 6.3 mL). After about 0.5 hours, add acetone (10 mmol) to the reaction bottle, continue to react at this temperature for half an hour, then warm to room temperature and continue to react for 8 hours. Remove the solvent under reduced pressure, add hydrochloric acid and acetic acid, and reflux for about 2 hours. Cool to room temperature, add deionized water, and then extract with ethyl acetate. After concentration, separate through a silica gel column, remove the solvent to obtain 2.24 g of compound Z5, with a yield of 51%.

[0178] Compound Z5 (2.2 g, 5 mmol) and diphenylamine (2.03 g, 12 mmol) were dissolved in anhydrous toluene, sodium tert-butoxide (1.15 g, 12 mmol) and tris dibenzylideneacetone dipalladium (0.23 g, 0.25 mmol) were added, nitrogen was replaced three times, tri-tert-butylphosphine (0.25 mmol) was added, the temperature was gradually raised to 80°C, stirred for reaction for 12 hours, and the heat source was removed. After the system was cooled, deionized water was added, the organic layer was separated, and extracted with ethyl acetate three times, concentrated under reduced pressure, and passed through a silica gel column to obtain 2.86 g of the product aromatic amine organic compound R1, with a yield of 81%, MS = 706 [M + ].

[0179] Example 2

[0180] The synthetic route of the aromatic amine organic compound R17 of this embodiment is as follows:

[0181]

[0182] Weigh compound Z6 (7.38 g, 30 mmol), compound Z7 (10.8 g, 30 mmol), potassium carbonate (8.28 g, 60 mmol), tetrakis(triphenylphosphine)palladium (1.04 g, 0.9 mmol) into a two-necked flask, add a mixed solvent of toluene and methanol, replace nitrogen three times, heat to 90°C, and stir overnight. After the reaction solution is cooled to room temperature, water is added, and it is extracted with ethyl acetate, dried with sodium sulfate, and the organic solvent is removed by vacuum distillation. The target product compound Z8 is separated by silica gel column chromatography to obtain 6.86 g of the total product, with a yield of 65%.

[0183] Dissolve compound Z8 (5.28 g, 15 mmol) and diphenylamine (2.53 g, 15 mmol) in anhydrous toluene, add sodium tert-butoxide (1.73 g, 18 mmol) and tris dibenzylideneacetone dipalladium (0.41 g, 0.45 mmol), replace nitrogen three times, add tri-tert-butylphosphine (0.45 mmol), gradually raise the temperature to 80°C, stir and react for 12 hours, and remove the heat source. After the system is cooled, add deionized water, separate the organic layer, extract with ethyl acetate three times, concentrate under reduced pressure, and pass through a silica gel column to obtain 4.7 g of product compound Z9, with a yield of 71%;

[0184] Dissolve compound Z10 (7.72 g, 20 mmol) and diphenylamine (3.38 g, 20 mmol) in anhydrous toluene, add sodium tert-butoxide (2.3 g, 24 mmol) and tris dibenzylideneacetone dipalladium (0.55 g, 0.6 mmol), replace nitrogen three times, add tri-tert-butylphosphine (0.6 mmol), gradually raise the temperature to 80°C, stir and react for 12 hours, and remove the heat source. After the system is cooled, add deionized water, separate the organic layer, extract with ethyl acetate three times, concentrate under reduced pressure, and pass through a silica gel column to obtain 7.13 g of product compound Z11, with a yield of 75%;

[0185] Dissolve compound Z11 (4.75 g, 10 mmol) in anhydrous tetrahydrofuran, cool to -78 °C, and slowly add butyl lithium (1.6 M, 6.3 mL). After about 0.5 hours, add a tetrahydrofuran solution of compound Z9 (10 mmol) dropwise to the reaction flask, continue to react at this temperature for half an hour, then warm to room temperature and continue to react for 8 hours. Remove the solvent under reduced pressure, add hydrochloric acid and acetic acid, and reflux for about 2 hours. Cool to room temperature, add deionized water, and then extract with ethyl acetate. After concentration, separate through a silica gel column, remove the solvent to obtain a total of 4.43 g of compound Z12, with a yield of 54%.

[0186] Dissolve compound Z12 (4.1 g, 5 mmol) in anhydrous tetrahydrofuran, cool the temperature to -78 °C, and slowly add butyllithium (1.6 M, 3.1 mL). After about 0.5 hour, add acetone (10 mmol) dropwise to the reaction flask, continue the reaction at this temperature for half an hour, then raise the temperature to room temperature and continue the reaction for 8 h. Remove the solvent under reduced pressure, add hydrochloric acid and acetic acid, and reflux for about 2 hours. Cool to room temperature, add deionized water, and then extract with ethyl acetate. After concentration, separate by silica gel column chromatography, and remove the solvent to obtain 2.27 g of the aromatic amine organic compound R17 with a yield of 58%. MS: 782 [M + .

[0187] Example 3

[0188] The synthetic route of the aromatic amine organic compound R34 in this example is as follows:

[0189]

[0190] Dissolve compound Z13 (10.64 g, 40 mmol) in anhydrous tetrahydrofuran, cool the temperature to -78 °C, and slowly add butyllithium (1.6 M, 25 mL). After about 0.5 hour, add a tetrahydrofuran solution of compound Z2 (40 mmol) dropwise to the reaction flask, continue the reaction at this temperature for half an hour, then raise the temperature to room temperature and continue the reaction for 8 h. Remove the solvent under reduced pressure, add hydrochloric acid and acetic acid, and reflux for about 2 hours. Cool to room temperature, add deionized water, and then extract with ethyl acetate. After concentration, separate by silica gel column chromatography, and remove the solvent to obtain 11.86 g of compound Z14 with a yield of 60%.

[0191] Weigh compound Z14 (9.88 g, 20 mmol), o-chlorophenylboronic acid (3.12 g, 20 mmol), potassium carbonate (5.52 g, 40 mmol), and tetrakis(triphenylphosphine)palladium(0) (0.69 g, 0.6 mmol) and add them to a two-necked flask. Add a mixed solvent of toluene and methanol, displace nitrogen three times, then raise the temperature to 90 °C and stir overnight. After the reaction solution cools to room temperature, add water, extract with ethyl acetate, dry with sodium sulfate, distill off the organic solvent under reduced pressure, and separate by silica gel column chromatography with sample mixing to obtain 5.07 g of the target product compound Z15 with a yield of 53%.

[0192] Dissolve compound Z15 (4.78 g, 10 mmol) in anhydrous tetrahydrofuran, cool to -78 °C, and slowly add butyl lithium (1.6 M, 6.3 mL). After about 0.5 hours, add acetone (10 mmol) to the reaction bottle, continue to react for half an hour at this temperature, then warm to room temperature and continue to react for 8 hours. Remove the solvent under reduced pressure, add hydrochloric acid and acetic acid, and reflux for about 2 hours. Cool to room temperature, add deionized water, and then extract with ethyl acetate. After concentration, separate through a silica gel column, remove the solvent to obtain compound Z16, a total of 2.55 g, with a yield of 58%.

[0193] Compound Z16 (2.2 g, 5 mmol) and compound Z17 (2.2 g, 12 mmol) were dissolved in anhydrous toluene, sodium tert-butoxide (1.15 g, 12 mmol) and tris dibenzylideneacetone dipalladium (0.23 g, 0.25 mmol) were added, and nitrogen was replaced three times, and tri-tert-butylphosphine (0.25 mmol) was added, and the temperature was gradually raised to 80°C, and the reaction was stirred for 12 hours, and the heat source was removed. After the system was cooled, deionized water was added, the organic layer was separated, and extracted with ethyl acetate three times, concentrated under reduced pressure, and passed through a silica gel column to obtain 3.04 g of the product aromatic amine organic compound R34, with a yield of 83%, MS=734 [M + ].

[0194] Example 4

[0195] The synthetic route of the aromatic amine organic compound R73 of this embodiment is as follows:

[0196]

[0197] Dissolve compound Z18 (10.64 g, 40 mmol) in anhydrous tetrahydrofuran, cool to -78 °C, and slowly add butyl lithium (1.6 M, 25 mL). After about 0.5 hours, add a tetrahydrofuran solution of compound Z2 (40 mmol) dropwise to the reaction flask, continue to react at this temperature for half an hour, then warm to room temperature and continue to react for 8 hours. Remove the solvent under reduced pressure, add hydrochloric acid and acetic acid, and reflux for about 2 hours. Cool to room temperature, add deionized water, and then extract with ethyl acetate. After concentration, separate through a silica gel column, remove the solvent to obtain a total of 9.88 g of compound Z19, with a yield of 50%.

[0198] Compound Z19 (9.88 g, 20 mmol), o-chlorophenylboronic acid (3.12 g, 20 mmol), potassium carbonate (5.52 g, 40 mmol), tetrakis(triphenylphosphine)palladium (0.69 g, 0.6 mmol) were weighed and added to a two-necked flask, and a mixed solvent of toluene and methanol was added. After replacing nitrogen three times, the temperature was raised to 90°C and stirred overnight. After the reaction solution was cooled to room temperature, water was added, and it was extracted with ethyl acetate, dried with sodium sulfate, and the organic solvent was removed by vacuum distillation. The target product compound Z20 was separated by silica gel column chromatography to obtain 4.88 g of the total product, with a yield of 51%.

[0199] Dissolve compound Z20 (4.78 g, 10 mmol) in anhydrous tetrahydrofuran, cool to -78 °C, and slowly add butyl lithium (1.6 M, 6.3 mL). After about 0.5 hours, add acetone (10 mmol) to the reaction bottle, continue to react for half an hour at this temperature, then warm to room temperature and continue to react for 8 hours. Remove the solvent under reduced pressure, add hydrochloric acid and acetic acid, and reflux for about 2 hours. Cool to room temperature, add deionized water, and then extract with ethyl acetate. After concentration, separate through a silica gel column, remove the solvent to obtain compound Z21, a total of 2.51 g, with a yield of 57%.

[0200] Compound Z21 (2.2 g, 5 mmol) and phenylnaphthylamine (2.63 g, 12 mmol) were dissolved in anhydrous toluene, sodium tert-butoxide (1.15 g, 12 mmol) and tris dibenzylideneacetone dipalladium (0.23 g, 0.25 mmol) were added, nitrogen was replaced three times, tri-tert-butylphosphine (0.15 mmol) was added, the temperature was gradually raised to 80°C, stirred for reaction for 12 hours, and the heat source was removed. After the system was cooled, deionized water was added, the organic layer was separated, and extracted with ethyl acetate three times, concentrated under reduced pressure, and passed through a silica gel column to obtain 2.98 g of the product aromatic amine organic compound R73, with a yield of 74%, MS=806 [M + ].

[0201] Example 5

[0202] The synthetic route of the aromatic amine organic compound R97 of this embodiment is as follows:

[0203]

[0204] Weigh compound Z2 (12.95 g, 40 mmol), compound Z22 (9.28 g, 40 mmol), potassium carbonate (11.04 g, 80 mmol), tetrakis(triphenylphosphine)palladium (1.38 g, 1.2 mmol) into a two-necked flask, add a mixed solvent of toluene and methanol, replace nitrogen three times, heat to 90°C, and stir overnight. After the reaction solution is cooled to room temperature, water is added, and it is extracted with ethyl acetate, dried with sodium sulfate, and the organic solvent is removed by vacuum distillation. The target product compound Z23 is separated by silica gel column chromatography to obtain 9.98 g in total, with a yield of 65%.

[0205] Dissolve compound Z1 (7.68 g, 20 mmol) in anhydrous tetrahydrofuran, cool to -78 °C, and slowly add butyl lithium (1.6 M, 12.5 mL). After about 0.5 hours, add a tetrahydrofuran solution of compound Z23 (20 mmol) dropwise to the reaction flask, continue to react at this temperature for half an hour, then warm to room temperature and continue to react for 8 hours. Remove the solvent under reduced pressure, add hydrochloric acid and acetic acid, and reflux for about 2 hours. Cool to room temperature, add deionized water, and then extract with ethyl acetate. After concentration, separate through a silica gel column, remove the solvent to obtain compound Z24, a total of 6.2 g, with a yield of 56%.

[0206] Dissolve compound Z24 (5.54 g, 10 mmol) in anhydrous tetrahydrofuran, cool to -78 °C, and slowly add butyl lithium (1.6 M, 6.3 mL). After about 0.5 hours, add acetone (10 mmol) to the reaction bottle, continue to react for half an hour at this temperature, then warm to room temperature and continue to react for 8 hours. Remove the solvent under reduced pressure, add hydrochloric acid and acetic acid, and reflux for about 2 hours. Cool to room temperature, add deionized water, and then extract with ethyl acetate. After concentration, separate through a silica gel column, remove the solvent to obtain 3.2 g of compound Z25, with a yield of 62%.

[0207] Compound Z25 (2.58 g, 5 mmol) and diphenylamine (2.03 g, 12 mmol) were dissolved in anhydrous toluene, sodium tert-butoxide (1.15 g, 12 mmol) and tris dibenzylideneacetone dipalladium (0.23 g, 0.25 mmol) were added, nitrogen was replaced three times, tri-tert-butylphosphine (0.15 mmol) was added, the temperature was gradually raised to 80°C, stirred for reaction for 12 hours, and the heat source was removed. After the system was cooled, deionized water was added, the organic layer was separated, and extracted with ethyl acetate three times, concentrated under reduced pressure, and passed through a silica gel column to obtain 2.89 g of the product aromatic amine organic compound R97, with a yield of 74%, MS = 782 [M + ].

[0208] Example 6

[0209] The synthetic route of the aromatic amine organic compound R98 of this embodiment is as follows:

[0210]

[0211] Dissolve compound Z18 (5.32 g, 20 mmol) in anhydrous tetrahydrofuran, cool to -78 °C, and slowly add butyl lithium (1.6 M, 12.5 mL). After about 0.5 hours, add a tetrahydrofuran solution of compound Z26 (20 mmol) dropwise to the reaction flask, continue to react at this temperature for half an hour, then warm to room temperature and continue to react for 8 hours. Remove the solvent under reduced pressure, add hydrochloric acid and acetic acid, and reflux for about 2 hours. Cool to room temperature, add deionized water, and then extract with ethyl acetate. After concentration, separate through a silica gel column, remove the solvent to obtain a total of 5.53 g of compound Z27, with a yield of 53%.

[0212] Dissolve compound Z27 (5.22 g, 10 mmol) in anhydrous tetrahydrofuran, cool to -78 °C, and slowly add butyl lithium (1.6 M, 6.3 mL). After about 0.5 hours, add acetone (10 mmol) to the reaction bottle, continue to react for half an hour at this temperature, then warm to room temperature and continue to react for 8 hours. Remove the solvent under reduced pressure, add hydrochloric acid and acetic acid, and reflux for about 2 hours. Cool to room temperature, add deionized water, and then extract with ethyl acetate. After concentration, separate through a silica gel column, remove the solvent to obtain 3.77 g of compound Z28, with a yield of 62%.

[0213] Compound Z28 (3.04 g, 5 mmol) and diphenylamine (2.03 g, 12 mmol) were dissolved in anhydrous toluene, sodium tert-butoxide (1.15 g, 12 mmol) and tris dibenzylideneacetone dipalladium (0.23 g, 0.25 mmol) were added, nitrogen was replaced three times, tri-tert-butylphosphine (0.15 mmol) was added, the temperature was gradually raised to 80°C, stirred for reaction for 12 hours, and the heat source was removed. After the system was cooled, deionized water was added, the organic layer was separated, and extracted with ethyl acetate three times, concentrated under reduced pressure, and passed through a silica gel column to obtain 3.07 g of the product aromatic amine organic compound R98, with a yield of 74%, MS = 830 [M + ].

[0214] Example 7

[0215] The synthetic route of the aromatic amine organic compound R99 of this embodiment is as follows:

[0216]

[0217] Dissolve compound Z30 (3.41 g, 10 mmol) in anhydrous tetrahydrofuran, cool to -78 °C, and slowly add butyl lithium (1.6 M, 6.3 mL). After about 0.5 hours, add a tetrahydrofuran solution of compound Z29 (10 mmol) dropwise to the reaction flask, continue to react at this temperature for half an hour, then warm to room temperature and continue to react for 8 hours. Remove the solvent under reduced pressure, add hydrochloric acid and acetic acid, and reflux for about 2 hours. Cool to room temperature, add deionized water, and then extract with ethyl acetate. After concentration, separate through a silica gel column, remove the solvent to obtain 3.25 g of compound Z31, with a yield of 58%.

[0218] Compound Z31 (2.8 g, 5 mmol) and diphenylamine (2.03 g, 12 mmol) were dissolved in anhydrous toluene, sodium tert-butoxide (1.15 g, 12 mmol) and tris dibenzylideneacetone dipalladium (0.23 g, 0.25 mmol) were added, nitrogen was replaced three times, tri-tert-butylphosphine (0.15 mmol) was added, the temperature was gradually raised to 80°C, stirred for reaction for 12 hours, and the heat source was removed. After the system was cooled, deionized water was added, the organic layer was separated, and extracted with ethyl acetate three times, concentrated under reduced pressure, and passed through a silica gel column to obtain 2.66 g of the product aromatic amine organic compound R99, with a yield of 68%, MS = 782 [M + ].

[0219] Example 8

[0220] The synthetic route of the aromatic amine organic compound R100 of this embodiment is as follows:

[0221]

[0222] Dissolve compound Z27 (10.44 g, 20 mmol) in anhydrous tetrahydrofuran, cool to -78 °C, and slowly add butyl lithium (1.6 M, 12.5 mL). After about 0.5 hours, add acetone (20 mmol) to the reaction bottle, continue to react for half an hour at this temperature, then warm to room temperature and continue to react for 8 hours. Remove the solvent under reduced pressure, add hydrochloric acid and acetic acid, and reflux for about 2 hours. Cool to room temperature, add deionized water, and then extract with ethyl acetate. After concentration, separate through a silica gel column, remove the solvent to obtain 5.23 g of compound Z32, with a yield of 54%.

[0223] Compound Z32 (4.84 g, 10 mmol) and diphenylamine (1.69 g, 10 mmol) were dissolved in anhydrous toluene, sodium tert-butoxide (1.15 g, 12 mmol) and tris dibenzylideneacetone dipalladium (0.27 g, 0.3 mmol) were added, nitrogen was replaced three times, tri-tert-butylphosphine (0.3 mmol) was added, the temperature was gradually raised to 80°C, stirred for reaction for 12 hours, and the heat source was removed. After the system was cooled, deionized water was added, the organic layer was separated, and extracted with ethyl acetate three times, concentrated under reduced pressure, and passed through a silica gel column to obtain 4.47 g of product compound Z33, with a yield of 78%;

[0224] Compound Z33 (286 g, 5 mmol) and compound Z34 (1.43 g, 5 mmol) were dissolved in anhydrous toluene, sodium tert-butoxide (0.58 g, 6 mmol) and tris dibenzylideneacetone dipalladium (0.14 g, 0.15 mmol) were added, and nitrogen was replaced three times, and tri-tert-butylphosphine (0.15 mmol) was added, and the temperature was gradually raised to 80°C, and the reaction was stirred for 12 hours, and the heat source was removed. After the system was cooled, deionized water was added, the organic layer was separated, and extracted with ethyl acetate three times, concentrated under reduced pressure, and passed through a silica gel column to obtain 3.25 g of the product aromatic amine organic compound R100, with a yield of 79%, MS=822 [M + ].

[0225] Example 9

[0226] The synthetic route of the aromatic amine organic compound R101 of this embodiment is as follows:

[0227]

[0228] Compound Z5 (2.2 g, 5 mmol) and compound Z35 (2.94 g, 12 mmol) were dissolved in anhydrous toluene, sodium tert-butoxide (1.15 g, 12 mmol) and tris dibenzylideneacetone palladium (0.23 g, 0.25 mmol) were added, and after replacing nitrogen three times, tri-tert-butylphosphine (0.25 mmol) was added, and the temperature was gradually raised to 80°C, stirred for reaction for 12 hours, and the heat source was removed. After the system was cooled, deionized water was added, the organic layer was separated, and extracted with ethyl acetate three times, concentrated under reduced pressure, and passed through a silica gel column to obtain 2.36 g of the product aromatic amine organic compound R101, with a yield of 55%, MS=858 [M + ].

[0229] Comparative Example 1

[0230] The organic compound in this comparative example is C1, and its chemical structure is as follows:

[0231]

[0232] Comparative Example 2

[0233] The organic compound of this comparative example is C2, and its chemical structural formula is as follows:

[0234]

[0235] Fabricating an OLED device

[0236] In this embodiment, in the OLED device, ITO is used as the anode material, HATCN is used as the hole injection layer material, HT is used as the hole transport material, the organic compounds in Examples 1-9 and Comparative Examples 1-2 are used as the electron blocking layer materials, RH is used as the host material of the light-emitting layer material, RD is used as the doping material of the light-emitting layer material, ET and Liq (lithium 8-hydroxyquinoline) are used as the electron transport materials, Liq is used as the electron injection material, and Al is used as the cathode material, forming a device structure of ITO / HATCN / HT / electron blocking layer material / RH:RD / ET:Liq / Liq / Al.

[0237] A schematic diagram of the OLED device is as Figure 1 shown. Among them, 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.

[0238] The chemical structural formulas of the above-mentioned HATCN, HT, RH, RD, ET, and Liq are as follows:

[0239]

[0240] The above-mentioned materials HATCN, HT, RH, RD, ET, and Liq are all commercially available, or their synthesis methods are all prior arts.

[0241] The following specifically describes the preparation process of the OLED device using the above-mentioned materials through specific examples.

[0242] Device Example 1

[0243] The method for fabricating the OLED device in this embodiment includes the following steps:

[0244] 1) Clean the ITO conductive glass anode layer, and then ultrasonically clean it with deionized water, acetone, and isopropyl alcohol for 15 minutes, and then treat it in a plasma cleaner for 5 minutes to improve the electrode work function;

[0245] 2) On the ITO anode layer, deposit the hole injection layer material HATCN by vacuum evaporation, with a thickness of 5 nm and an evaporation rate

[0246] 3) On the hole injection layer, a hole transporting material HT is deposited by vacuum evaporation, with a thickness of 90 nm;

[0247] 4) On the hole transporting layer, an electron blocking layer material, an aromatic amine organic compound R1, is deposited by vacuum evaporation, with a thickness of 20 nm;

[0248] 5) On the electron blocking layer, a light-emitting layer is deposited. RH is used as the host material and RD is used as the doping material. The mass ratio of RD to RH is 2:98, and the thickness is 40 nm;

[0249] 6) On the light-emitting layer, an electron transporting material ET and Liq are deposited by vacuum evaporation, with a mass ratio of 5:5 and a thickness of 30 nm;

[0250] 7) On the electron transporting layer, an electron injection layer Liq is deposited by vacuum evaporation, with a thickness of 2 nm;

[0251] 8) On the electron injection layer, a cathode Al layer is deposited by vacuum evaporation, with a thickness of 80 nm.

[0252] Device Example 2-9

[0253] It is basically the same as Device Example 1, except that the electron blocking layer materials of Device Examples 2-9 are respectively selected from the aromatic amine organic compounds of Examples 2-9, as shown in Table 1 specifically.

[0254] Device Comparative Examples 1-2

[0255] It is basically the same as Device Example 1, except that the electron blocking layer materials of Device Comparative Examples 1-2 are respectively selected from the organic compounds C1 and C2 of Comparative Examples 1-2.

[0256] Performance Detection and Results

[0257] Please refer to Figure 2 , and perform mass spectrometry analysis on the aromatic amine organic compound R1 of Example 1 to obtain the mass spectrometry spectrum of the aromatic amine organic compound R1.

[0258] Use a characterization device to test the current-voltage (J-V) characteristics of the OLED devices of Device Examples 1-9 and Device Comparative Examples 1-2, and record important parameters such as luminous efficiency and lifespan at the same time. Among them, the luminous efficiency is the relative value obtained when the current density is 10 mA / cm 2 . The lifespan LT95@1000nits refers to the time when the brightness of the device drops from the initial brightness of 1000 nits to 95% of the initial brightness under a constant current. The luminous efficiency and lifespan of the OLED devices of Device Examples 1-9 and Device Comparative Example 2 are all relative values with respect to the OLED device of Device Comparative Example 1. The detection results are shown in Table 1 below.

[0259] Table 1:

[0260] OLED device Electron blocking layer material Luminescence efficiency (relative value) Lifetime (relative value) Device Example 1 R1 1.21 1.24 Device Example 2 R17 1.23 1.22 Device Example 3 R34 1.17 1.14 Device Example 4 R73 1.20 1.23 Device Example 5 R97 1.22 1.20 Device Example 6 R98 1.20 1.18 Device Example 7 R99 1.19 1.23 Device Example 8 R100 1.21 1.19 Device Example 9 R101 1.16 1.17 Device Comparative Example 1 C1 1 1 Device Comparative Example 2 C2 1.03 1.05

[0261] As can be seen from Table 1, compared with the OLED devices of Comparative Examples 1-2, the OLED devices of Examples 1-9 of the present application have higher efficiency and longer lifespan. It can be seen that the arylamine organic compound of the present application as an electron blocking material can effectively improve the luminous efficiency and lifespan of the organic electroluminescent device.

[0262] The arylamine organic compound of the present application has two arylamine structures, which can effectively improve the carrier transport ability of the amine organic compound molecules, achieve the balance between hole transport and electron transport in the organic electronic device, and thus improve the luminous efficiency and lifespan of the device. In addition, in the arylamine organic compound of the present application, the two fluorene groups are connected by sp3 hybridized carbon atoms, which can reduce the conjugation degree between the diarylamines, increase the triplet energy level of the organic compound molecules, and avoid exciton diffusion in the light-emitting layer.

[0263] The above has introduced in detail the arylamine organic compound, mixture, composition and organic electronic device provided by the embodiments of the present application. Specific examples are used herein to elaborate on the principle and implementation manner of the present application. The description of the above embodiments is only used to help understand the method and its core idea of the present application; at the same time, for those skilled in the art, according to the idea of the present application, there will be changes in the specific implementation manner and application scope. In summary, the content of this specification should not be construed as a limitation to the present application.

Claims

1. An aromatic amine organic compound, characterized in that, it has a structure shown in the general formula (1): （1） Wherein: Ar 1 、Ar 2 independently selected from any one of the following structures: 、 ； Ar 3 、Ar 4 independently selected from any one of the following structures: 、 、 ； L 1 、L 2 、L 3 、L 4 selected from single bonds; R 1 、R 2 are independently selected from methyl or phenyl; R 3 selected from methyl; R 4 、R 5 are independently selected from hydrogen or phenyl; R 6 selected from hydrogen; R 7 selected from hydrogen, methyl or phenyl; m1 is selected from 1 or 3; m2 is selected from 1 or 4; m3 is selected from 3.

2. The aromatic amine organic compound according to claim 1, characterized in that, the aromatic amine organic compound is selected from the structures shown in formula (3-1), (3-2) or (3-3): 。 3. The aromatic amine organic compound according to claim 1 or 2, characterized in that, The said Any one selected from the following groups: ； The said Any one selected from the following groups: 。 4. The aromatic amine organic compound according to claim 1, characterized in that, the aromatic amine organic compound is selected from the following structures: 。 5. A mixture, characterized in that: the mixture includes the aromatic amine organic compound according to any one of claims 1-4 and at least one organic functional material, and 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 light-emitting material, a host material or an organic dye.

6. A composition, characterized in that: the composition includes the aromatic amine organic compound according to any one of claims 1-4 or the mixture according to claim 5, and at least one organic solvent.

7. An organic electronic device including at least one organic functional layer, characterized in that: the organic functional layer includes the aromatic amine organic compound according to any one of claims 1-4, or the mixture according to claim 5, or the organic functional layer is prepared from the composition according to claim 6; the organic functional layer is an electron blocking layer.

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