Organic compounds and mixtures, compositions and organic electronic devices thereof

Abstract

This application discloses an organic compound and mixtures, compositions and organic electronic devices comprising the organic compound, the organic compound having a structure as shown in general formula (1): the organic compound is used in organic electronic devices, particularly as a hole transport material in the hole transport layer of organic electronic devices, to improve the efficiency and lifespan of organic electronic devices.

Description

Technical Field

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

[0002] Organic electronic devices, especially organic light-emitting diodes (OLEDs), are widely used due to their characteristics such as self-emission, high brightness, high efficiency, low driving voltage, wide viewing angle, high contrast, and high responsiveness.

[0003] Organic electroluminescence (OEC) refers to the phenomenon of converting electrical energy into light energy using organic materials. OEC devices typically have a positive electrode, a negative electrode, and an organic layer between them. To improve the efficiency and lifetime of OEC devices, the organic layer has a multi-layered structure, with each layer containing a different organic material. Specifically, it can include a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, and an electron injection layer. In such OEC devices, applying a voltage between the 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. Such OEC devices possess characteristics such as self-illumination, high brightness, high efficiency, low driving voltage, wide viewing angle, high contrast, and high responsiveness.

[0004] To obtain efficient organic electronic devices, in addition to developing high-performance luminescent materials, the development of hole transport materials is also crucial. Currently, most hole transport materials are small-molecule materials based on carbazole derivatives. Organic electronic devices using such hole transport materials suffer from an imbalance between hole and electron transport, resulting in lower luminous efficiency and shorter lifetime.

[0005] Therefore, further improvements are needed in hole transport materials to enhance the performance of organic electronic devices. Summary of the Invention

[0006] In view of this, this application provides an organic compound as a novel hole transport material, which is used in organic electronic devices to improve the problems of low luminous efficiency and short lifespan of organic electronic devices.

[0007] The technical solution of this application is as follows:

[0008] An organic compound having a structure as shown in general formula (1):

[0009]

[0010] Among them, R 1 and R2 The group is independently selected from -H, -D, or substituted or unsubstituted linear alkyl groups having 1 to 20 carbon atoms, linear alkoxy groups having 1 to 20 carbon atoms, or linear thioalkoxy groups having 1 to 20 carbon atoms, or substituted or unsubstituted branched alkyl groups having 3 to 20 carbon atoms, or branched alkoxy groups having 3 to 20 carbon atoms, or branched thioalkoxy groups having 3 to 20 carbon atoms, or substituted or unsubstituted cyclic alkyl groups having 3 to 20 carbon atoms, or cyclic alkoxy groups having 3 to 20 carbon atoms, or cyclic thioalkoxy groups having 3 to 20 carbon atoms, or silyl groups, or ketone groups having 1 to 20 carbon atoms, or alkoxycarbonyl groups having 2 to 20 carbon atoms, or aryloxycarbonyl groups having 7 to 20 carbon atoms, cyano, carbamoyl, haloformyl, formyl, isocyano, isocyanate, and so on. Thiocyanate group, or isothiocyanate group, hydroxyl group, nitro group, amino group, -CF3, -Cl, -Br, -F, -I, or substituted or unsubstituted aromatic group having 6 to 60 ring atoms, or substituted or unsubstituted heteroaromatic group having 5 to 60 ring atoms, or substituted or unsubstituted aryloxy group having 5 to 60 ring atoms, or substituted or unsubstituted heteroaryloxy group having 5 to 60 ring atoms, or combinations of these groups;

[0011] R 1 and R 2 At least one is not selected from H;

[0012] Ar 1 Ar 2 and Ar 3 The group is independently selected from substituted or unsubstituted aromatic groups containing 6 to 60 ring atoms, substituted or unsubstituted heteroaromatic groups containing 6 to 60 ring atoms, or combinations thereof.

[0013] This application also provides a mixture comprising the above-mentioned organic compound 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, organic light-emitting guest materials, organic host materials, or inorganic quantum dots.

[0014] This application also provides a composition comprising the above-described organic compound or mixture thereof, and at least one organic solvent.

[0015] This application also provides an organic electronic device comprising at least one functional layer, wherein the functional layer comprises the above-mentioned organic compound, or the functional layer comprises the above-mentioned mixture, or the functional layer is prepared from the above-mentioned composition.

[0016] The organic compound of this application is an aromatic amine organic compound, which has an aromatic amine group introduced at the 2-position of the benzofuranocarbazoyl group and the aforementioned R group introduced at the ortho-position of the aromatic amine group. 1 and / or R 2 This effectively improves molecular packing, giving the material molecules greater rigidity and thus increasing the glass transition temperature of the material molecules. Organic electronic devices using the organic compounds of this application as hole transport materials exhibit longer lifetimes and higher luminous efficiency. Attached Figure Description

[0017] 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.

[0018] Figure 1 This is a schematic diagram of the structure of an organic electronic device provided in an embodiment of this application. Detailed Implementation

[0019] 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 "including" means "including but not limited to", and the term "multiple" means "two or more". 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.

[0020] Unless otherwise defined, all technical and scientific terms used herein have the same meaning as commonly understood by those skilled in the art.

[0021] The term “and / or” as used herein includes any and all combinations of one or more of the related listed items.

[0022] In this application, "substitution" means that the hydrogen atom in the substituent is replaced by the substituent.

[0023] In this application, when the same substituent appears multiple times, it can be independently selected from different groups. For example, if the general formula contains multiple R... 1 Then R 1 It can be independently selected from different groups.

[0024] 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 carbon atoms, heterocyclic group containing 3-20 ring atoms, aromatic group containing 6-20 ring atoms, heteroaromatic group containing 5-20 ring atoms, -NR'R", silyl, carbonyl, alkoxycarbonyl, etc. The groups include aryloxycarbonyl, carbamoyl, haloformyl, formyl, isocyanate, thiocyanate, isothiocyanate, hydroxyl, and trifluoromethyl, and these groups may be further substituted with 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, cyano, isocyano, nitro or halogen, alkyl containing 1-10 C atoms, heterocyclic group containing 3-20 ring atoms, aromatic group containing 6-20 ring atoms, and heteroaromatic group containing 5-20 ring atoms. Preferably, R is selected from, but not limited to, a deuterium atom, a cyano group, an isocyano group, a nitro group or a halogen, an alkyl group containing 1-10 carbon atoms, a heterocyclic group containing 3-10 ring atoms, an aromatic group containing 6-20 ring atoms, a heteroaromatic group containing 5-20 ring atoms, a silyl group, a carbonyl group, an alkoxycarbonyl group, an aryloxycarbonyl group, a carbamoyl group, a haloformyl group, a formyl group, an isocyanate group, a thiocyanate group, an isothiocyanate group, a hydroxyl group, or a trifluoromethyl group, and the above groups may be further substituted with substituents acceptable in the art. More preferably, R is selected from, but not limited to, a deuterium atom, an alkyl group containing 1-5 carbon atoms, an aromatic group containing 6-13 ring atoms, or a heteroaromatic group containing 5-13 ring atoms.

[0025] 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 included 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.

[0026] 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, fused-ring aryl, or 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 comprising 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, and particularly preferably a substituted or unsubstituted aryl having 6 to 14 ring atoms. 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.

[0027] 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, an O atom, an 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. Suitable examples include, but are not limited to: thiophene, furanyl, pyrrole, imidazole, diazolyl, triazolyl, imidazole, pyridyl, bipyridyl, pyrimidinyl, triazine, acridine, and pyridazine. α-Pyrazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, phthalazinyl, pyridinylpyrimidinyl, pyridinylpyrazinyl, benzothiopheneyl, benzofuranyl, indolyl, pyrroloimidazolyl, pyrrolopyrrolyl, thienopyrrolyl, thienopyrrolyl, furanolyl, furanolyl, thienofuranyl, benzoisoxazolyl, benzoisothiazolyl, benzoimidazolyl, o-diazonyl, phenanthridine, primidyl, quinazolinone, dibenzothiopheneyl, dibenzofuranyl, carbazoleyl and their derivatives.

[0028] 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 including this term, such as "C 1-9"Alkyl" refers to an alkyl group comprising 1 to 9 carbon atoms, and each time it appears, it can independently be 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, tert-pentyl, cyclopentyl, 1-methylpentyl, 3-methylpentyl, 2-ethylpentyl, 4-methyl-2-pentyl, n-hexyl, 1-methylhexyl, 2-ethylhexyl, 2-butylhexyl, cyclohexyl, 4-methylcyclohexyl, 4-tert-butylcyclohexyl, n-heptyl, 1-methylheptyl, 2,2-dimethylheptyl, 2-ethylheptyl, 2-butylheptyl, n-octyl, tert-octyl, 2-ethyloctyl, 2-butyloctyl, 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-pentadecanyl, n-hexadecyl, 2-ethylhexadecyl, 2-butylhexadecyl, 2-hexylhexadecyl, 2-octylhexadecyl, n-heptadecyl, n-octadecyl, n-octadecyl, n-hexadecyl, n-eicosyl, 2-ethyleicosyl, 2-butyleicosyl, 2-hexyleicosyl, 2-octyleicosyl, n-eicosyl, n-eicosyl, n-eicosyl, n-eicosyl, n-eicosyl, n-eicosyl, n-eicosyl, n-eicosyl, n-eicosyl, n-eicosyl, n-eicosyl, n-eicosyl, n-eicosyl, n-eicosyl, n-eicosyl, etc.

[0029] 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, and Cy-cyclohexyl.

[0030] 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.

[0031] 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.

[0032] 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).

[0033] 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.

[0034] In this application, the "*" connected to a single bond indicates a connection or fusion site.

[0035] 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.

[0036] 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.

[0037] 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... Six Rs on the benzene ring 1 They can be the same as or different from each other.

[0038] 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... 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.

[0039] In this application, "adjacent groups" means that there are no substituted sites between two substituents.

[0040] In this application, "D" represents a deuterium atom.

[0041] The technical solution of this application is as follows:

[0042] An aromatic amine organic compound having the structure shown in general formula (1):

[0043]

[0044] Among them, R 1 and R 2 The group is independently selected from -H, -D, or substituted or unsubstituted linear alkyl groups having 1 to 20 carbon atoms, linear alkoxy groups having 1 to 20 carbon atoms, or linear thioalkoxy groups having 1 to 20 carbon atoms, or substituted or unsubstituted branched alkyl groups having 3 to 20 carbon atoms, or branched alkoxy groups having 3 to 20 carbon atoms, or branched thioalkoxy groups having 3 to 20 carbon atoms, or substituted or unsubstituted cyclic alkyl groups having 3 to 20 carbon atoms, or cyclic alkoxy groups having 3 to 20 carbon atoms, or cyclic thioalkoxy groups having 3 to 20 carbon atoms, or silyl groups, or ketone groups having 1 to 20 carbon atoms, or alkoxycarbonyl groups having 2 to 20 carbon atoms, or aryloxycarbonyl groups having 7 to 20 carbon atoms, cyano, carbamoyl, haloformyl, formyl, isocyano, isocyanate, and so on. Thiocyanate group, or isothiocyanate group, hydroxyl group, nitro group, amino group, -CF3, -Cl, -Br, -F, -I, or substituted or unsubstituted aromatic group having 6 to 60 ring atoms, or substituted or unsubstituted heteroaromatic group having 5 to 60 ring atoms, or substituted or unsubstituted aryloxy group having 5 to 60 ring atoms, or substituted or unsubstituted heteroaryloxy group having 5 to 60 ring atoms, or combinations of these groups;

[0045] R 1 and R 2 At least one is not selected from H;

[0046] Ar 1 Ar 2 and Ar 3 The group is independently selected from substituted or unsubstituted aromatic groups containing 6 to 60 ring atoms, substituted or unsubstituted heteroaromatic groups containing 6 to 60 ring atoms, or combinations of these groups. In one embodiment, R 1Selected from -D, or substituted or unsubstituted straight-chain alkyl groups having 1 to 10 carbon atoms, straight-chain alkoxy groups having 1 to 10 carbon atoms, or straight-chain thioalkoxy groups having 1 to 10 carbon atoms, or substituted or unsubstituted branched alkyl groups having 3 to 10 carbon atoms, or branched alkoxy groups having 3 to 10 carbon atoms, or branched thioalkoxy groups having 3 to 10 carbon atoms, or substituted or unsubstituted cyclic alkyl groups having 3 to 10 carbon atoms, or having 3 to 10 carbon atoms. Cyclic alkoxy groups having 3 to 10 carbon atoms, or cyclic thioalkoxy groups having 3 to 10 carbon atoms, or silyl groups, or ketone groups having 1 to 10 carbon atoms, or alkoxycarbonyl groups having 2 to 10 carbon atoms, or aryloxycarbonyl groups having 7 to 10 carbon atoms, cyano, carbamoyl, haloformyl, formyl, isocyano, isocyanate, thiocyanate, or isothiocyanate, hydroxyl, nitro, amino, -CF3, -Cl, -Br, -F, -I, or substituted or unsubstituted aromatic groups having 6 to 30 ring atoms, or substituted or unsubstituted heteroaromatic groups having 5 to 30 ring atoms, or substituted or unsubstituted aryloxy groups having 5 to 30 ring atoms, or substituted or unsubstituted heteroaromatic groups having 5 to 30 ring atoms, or combinations of these groups.

[0047] In one embodiment, R 1 It is selected from straight-chain alkyl groups having 1 to 8 carbon atoms, substituted or unsubstituted branched alkyl groups having 3 to 8 carbon atoms, substituted or unsubstituted cyclic alkyl groups having 3 to 8 carbon atoms, or silyl, cyano, isocyano, nitro, -CF3, -Cl, -Br, -F, -I, or substituted or unsubstituted aromatic groups having 6 to 20 ring atoms, or substituted or unsubstituted heteroaromatic groups having 5 to 20 ring atoms, or combinations of these groups.

[0048] In one embodiment, R 1 The group is selected from unsubstituted straight-chain alkyl groups having 1 to 4 carbon atoms, straight-chain alkyl groups having 1 to 4 carbon atoms substituted with one or more D atoms, or unsubstituted branched alkyl groups having 3 to 5 carbon atoms, branched alkyl groups having 3 to 5 carbon atoms substituted with one or more D atoms, or unsubstituted cyclic alkyl groups having 3 to 6 carbon atoms, cyclic alkyl groups having 3 to 6 carbon atoms substituted with one or more D atoms, or substituted or unsubstituted aromatic groups having 6 to 13 ring atoms, or substituted or unsubstituted heteroaromatic groups having 6 to 13 ring atoms, or combinations of these groups.

[0049] In some specific embodiments, R 1Selected from methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, tert-butyl, isobutyl, 2-ethylbutyl, 3,3-dimethylbutyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, cyclopentyl, 1-methylpentyl, 3-methylpentyl, 2-ethylpentyl, 4-methyl-2-pentyl, n-hexyl, 1-methylhexyl, 2-ethylhexyl, 2-butylhexyl, cyclohexyl, 4-methylcyclohexyl, 4-tert-butylcyclohexyl, n-heptyl, 1-methylheptyl, 2,2-dimethylheptyl, 2-ethylheptyl, 2-butylheptyl, n-octyl or adamantyl, and one or more of the following. Methyl group substituted with one or more D atoms, ethyl group substituted with one or more D atoms, n-propyl group substituted with one or more D atoms, isopropyl group substituted with one or more D atoms, n-butyl group substituted with one or more D atoms, sec-butyl group substituted with one or more D atoms, tert-butyl group substituted with one or more D atoms, isobutyl group substituted with one or more D atoms, 2-ethylbutyl group substituted with one or more D atoms, 3,3-dimethylbutyl group substituted with one or more D atoms, n-pentyl group substituted with one or more D atoms, isopentyl group substituted with one or more D atoms, and so on. Neopentyl with multiple D atoms substituted, tert-pentyl with one or more D atoms substituted, cyclopentyl with one or more D atoms substituted, 1-methylpentyl with one or more D atoms substituted, 3-methylpentyl with one or more D atoms substituted, 2-ethylpentyl with one or more D atoms substituted, 4-methyl-2-pentyl with one or more D atoms substituted, n-hexyl with one or more D atoms substituted, 1-methylhexyl with one or more D atoms substituted, 2-ethylhexyl with one or more D atoms substituted, 2-butylhexyl with one or more D atoms substituted. Cyclohexyl groups substituted with one or more D atoms, 4-methylcyclohexyl groups substituted with one or more D atoms, 4-tert-butylcyclohexyl groups substituted with one or more D atoms, n-heptyl groups substituted with one or more D atoms, 1-methylheptyl groups substituted with one or more D atoms, 2,2-dimethylheptyl groups substituted with one or more D atoms, 2-ethylheptyl groups substituted with one or more D atoms, 2-butylheptyl groups substituted with one or more D atoms, n-octyl groups substituted with one or more D atoms, adamantyl groups substituted with one or more D atoms, or groups having the following structural formulas:

[0050]

[0051] Where: X is selected from CR 3 Or N; Y is selected from CR 4 R 5 NR 4 SiR 4 R 5 , O, S, S=O or SO2;

[0052] R 3 R 4 R 5 Each occurrence is independently selected from substituted or unsubstituted linear alkyl groups having 1 to 10 carbon atoms, or substituted or unsubstituted branched alkyl groups having 3 to 10 carbon atoms, or substituted or unsubstituted cyclic alkyl groups having 3 to 10 carbon atoms, or silyl, cyano, isocyano, nitro, -CF3, -Cl, -Br, -F, -I, or substituted or unsubstituted aromatic groups having 6 to 10 ring atoms, or substituted or unsubstituted heteroaromatic groups having 5 to 10 ring atoms, or combinations of these groups.

[0053] When X is a linking site, X is selected from C (carbon atom); when Y is a linking site, Y is selected from N.

[0054] Furthermore, R 3 R 4 R 5 Each occurrence is independently selected from unsubstituted straight-chain alkyl with 1 to 4 carbon atoms, straight-chain alkyl with 1 to 4 carbon atoms substituted with one or more D atoms, or unsubstituted branched alkyl with 3 to 5 carbon atoms, branched alkyl with 3 to 5 carbon atoms substituted with one or more D atoms, or unsubstituted cyclic alkyl with 3 to 6 carbon atoms, cyclic alkyl with 3 to 6 carbon atoms substituted with one or more D atoms, or phenyl, or biphenyl, or terphenyl, or pyridyl, or pyrimidinyl, or naphthyl.

[0055] In one embodiment, R 1 It is selected from methyl, -CD3, ethyl, -CD2-CD3, isopropyl, -CD(CD3)2, tert-butyl, phenyl, or phenyl substituted with one or more methyl groups.

[0056] In one embodiment, R 2Selected from -D, or substituted or unsubstituted straight-chain alkyl groups having 1 to 10 carbon atoms, straight-chain alkoxy groups having 1 to 10 carbon atoms, or straight-chain thioalkoxy groups having 1 to 10 carbon atoms, or substituted or unsubstituted branched alkyl groups having 3 to 10 carbon atoms, or branched alkoxy groups having 3 to 10 carbon atoms, or branched thioalkoxy groups having 3 to 10 carbon atoms, or substituted or unsubstituted cyclic alkyl groups having 3 to 10 carbon atoms, or cyclic alkoxy groups having 3 to 10 carbon atoms, or cyclic thioalkoxy groups having 3 to 10 carbon atoms, or silyl groups, or ketone groups having 1 to 10 carbon atoms, or An alkoxycarbonyl group having 2 to 10 carbon atoms, or an aryloxycarbonyl group having 7 to 10 carbon atoms, a cyano group, a carbamoyl group, a haloformyl group, a formyl group, an isocyano group, an isocyanate group, a thiocyanate group, or an isothiocyanate group, a hydroxyl group, a nitro group, an amino group, -CF3, -Cl, -Br, -F, -I, 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 substituted or unsubstituted aryloxy group having 5 to 30 ring atoms, or a substituted or unsubstituted heteroaromatic group having 5 to 30 ring atoms, or a combination of these groups.

[0057] In one embodiment, R 2 It is selected from straight-chain alkyl groups having 1 to 8 carbon atoms, substituted or unsubstituted branched alkyl groups having 3 to 8 carbon atoms, substituted or unsubstituted cyclic alkyl groups having 3 to 8 carbon atoms, or silyl, cyano, isocyano, nitro, -CF3, -Cl, -Br, -F, -I, or substituted or unsubstituted aromatic groups having 6 to 20 ring atoms, or substituted or unsubstituted heteroaromatic groups having 5 to 20 ring atoms, or combinations of these groups.

[0058] In one embodiment, R 2 The group is selected from unsubstituted straight-chain alkyl groups having 1 to 4 carbon atoms, straight-chain alkyl groups having 1 to 4 carbon atoms substituted with one or more D atoms, or unsubstituted branched alkyl groups having 3 to 5 carbon atoms, branched alkyl groups having 3 to 5 carbon atoms substituted with one or more D atoms, or unsubstituted cyclic alkyl groups having 3 to 6 carbon atoms, cyclic alkyl groups having 3 to 6 carbon atoms substituted with one or more D atoms, or substituted or unsubstituted aromatic groups having 6 to 13 ring atoms, or substituted or unsubstituted heteroaromatic groups having 6 to 13 ring atoms, or combinations of these groups.

[0059] In some specific embodiments, R 2Selected from methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, tert-butyl, isobutyl, 2-ethylbutyl, 3,3-dimethylbutyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, cyclopentyl, 1-methylpentyl, 3-methylpentyl, 2-ethylpentyl, 4-methyl-2-pentyl, n-hexyl, 1-methylhexyl, 2-ethylhexyl, 2-butylhexyl, cyclohexyl, 4-methylcyclohexyl, 4-tert-butylcyclohexyl, n-heptyl, 1-methylheptyl, 2,2-dimethylheptyl, 2-ethylheptyl, 2-butylheptyl, n-octyl or adamantyl, and one or more of the following. Methyl group substituted with one or more D atoms, ethyl group substituted with one or more D atoms, n-propyl group substituted with one or more D atoms, isopropyl group substituted with one or more D atoms, n-butyl group substituted with one or more D atoms, sec-butyl group substituted with one or more D atoms, tert-butyl group substituted with one or more D atoms, isobutyl group substituted with one or more D atoms, 2-ethylbutyl group substituted with one or more D atoms, 3,3-dimethylbutyl group substituted with one or more D atoms, n-pentyl group substituted with one or more D atoms, isopentyl group substituted with one or more D atoms, and so on. Neopentyl with multiple D atoms substituted, tert-pentyl with one or more D atoms substituted, cyclopentyl with one or more D atoms substituted, 1-methylpentyl with one or more D atoms substituted, 3-methylpentyl with one or more D atoms substituted, 2-ethylpentyl with one or more D atoms substituted, 4-methyl-2-pentyl with one or more D atoms substituted, n-hexyl with one or more D atoms substituted, 1-methylhexyl with one or more D atoms substituted, 2-ethylhexyl with one or more D atoms substituted, 2-butylhexyl with one or more D atoms substituted. Cyclohexyl groups substituted with one or more D atoms, 4-methylcyclohexyl groups substituted with one or more D atoms, 4-tert-butylcyclohexyl groups substituted with one or more D atoms, n-heptyl groups substituted with one or more D atoms, 1-methylheptyl groups substituted with one or more D atoms, 2,2-dimethylheptyl groups substituted with one or more D atoms, 2-ethylheptyl groups substituted with one or more D atoms, 2-butylheptyl groups substituted with one or more D atoms, n-octyl groups substituted with one or more D atoms, adamantyl groups substituted with one or more D atoms, or groups having the following structural formulas:

[0060]

[0061] Where: X is selected from CR 3 Or N; Y is selected from CR 4 R 5 NR 4 SiR 4 R 5 , O, S, S=O or SO2;

[0062] R 3 R 4 R 5 Each occurrence is independently selected from substituted or unsubstituted linear alkyl groups having 1 to 10 carbon atoms, or substituted or unsubstituted branched alkyl groups having 3 to 10 carbon atoms, or substituted or unsubstituted cyclic alkyl groups having 3 to 10 carbon atoms, or silyl, cyano, isocyano, nitro, -CF3, -Cl, -Br, -F, -I, or substituted or unsubstituted aromatic groups having 6 to 10 ring atoms, or substituted or unsubstituted heteroaromatic groups having 5 to 10 ring atoms, or combinations of these groups.

[0063] When X is a connection site, X is selected from C; when Y is a connection site, Y is selected from N.

[0064] Furthermore, R 3 R 4 R 5 Each occurrence is independently selected from unsubstituted straight-chain alkyl with 1 to 4 carbon atoms, straight-chain alkyl with 1 to 4 carbon atoms substituted with one or more D atoms, or unsubstituted branched alkyl with 3 to 5 carbon atoms, branched alkyl with 3 to 5 carbon atoms substituted with one or more D atoms, or unsubstituted cyclic alkyl with 3 to 6 carbon atoms, cyclic alkyl with 3 to 6 carbon atoms substituted with one or more D atoms, or phenyl, or biphenyl, or terphenyl, or pyridyl, or pyrimidinyl, or naphthyl.

[0065] In some embodiments, R 2 Selected from methyl, -CD3, ethyl, -CD2-CD3, isopropyl, -CD(CD3)2, tert-butyl, phenyl, or phenyl substituted with one or more methyl groups.

[0066] In some embodiments, R 1 and R 2 Selected from the same group.

[0067] In some embodiments, R in general formula (1) 1 Not selected from H, R 1 Further definitions are as described above.

[0068] In other embodiments, R in general formula (1) 1 and R 2 None of them are selected from H, R 1 and R 2 Further definitions are as described above.

[0069] In some embodiments, Ar 1 Ar 2 and Ar 3Each group is independently selected from substituted or unsubstituted aromatic groups having 6 to 30 ring atoms, substituted or unsubstituted heteroaromatic groups having 6 to 30 ring atoms, or combinations thereof.

[0070] In some preferred embodiments, Ar 1 Ar 2 and Ar 3 Each is independently selected from substituted or unsubstituted aromatic groups having 6 to 16 ring atoms, substituted or unsubstituted heteroaromatic groups having 6 to 16 ring atoms, or combinations of these groups.

[0071] In some embodiments, Ar 1 Ar 2 and Ar 3 Each group is independently selected from the following groups:

[0072]

[0073] in:

[0074] Each time V appears, it is independently selected from CR. 6 Or N;

[0075] W is selected from NR 7 CR 8 R 9 SiR 8 R 9 , O, S, S=O or SO2;

[0076] R 6 R 7 R 8 and R 9Each occurrence is independently selected from -H, -D, or straight-chain alkyl groups having 1 to 20 carbon atoms, straight-chain alkoxy groups having 1 to 20 carbon atoms, straight-chain thioalkoxy groups having 1 to 20 carbon atoms, or branched alkyl groups having 3 to 20 carbon atoms, branched alkoxy groups having 3 to 20 carbon atoms, branched thioalkoxy groups having 3 to 20 carbon atoms, cyclic alkyl groups having 3 to 20 carbon atoms, cyclic alkoxy groups having 3 to 20 carbon atoms, or cyclic thioalkoxy groups having 3 to 20 carbon atoms, or silyl groups, or ketone groups having 1 to 20 carbon atoms, or alkoxycarbonyl groups having 2 to 20 carbon atoms, or aryloxycarbonyl groups having 7 to 20 carbon atoms, cyano, carbamoyl, haloformyl, formyl, isocyano, isocyanate, thiocyanate, isothiocyanate, hydroxyl. Nitro, amino, -CF3, -Cl, -Br, -F, -I, or alkenyl having 2 to 20 C 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 an aryloxy group having 6 to 60 substituted or unsubstituted ring atoms, or a heteroaryloxy group having 5 to 60 substituted or unsubstituted ring atoms, or a combination of these groups;

[0077] R 8 and R 9 They may form rings or not.

[0078] It is understood that in this application, when V is a connection site, V is C; when W is a connection site, Y is selected from N.

[0079] In some embodiments, Ar 3 Selected from phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthrene, fluoranthyl, triphenylene, pyrene, perylene, tetraphenyl, fluorenyl, dinaphthyl-2-phenylene, acenaphthyl, thiophene, furanyl, pyrrolyl, imidazolyl, triazolyl, imidazolyl, diazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, acridinel, pyridazinyl, quinolinyl, quinazolinyl, quinoxalinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, isoquinolinyl, indoleyl Doloyl, carbazoyl, benzothiopheneyl, benzofuranyl, pyrroloimidazoyl, pyrrolopyrryl, thienopyrryl, thienothiopheneyl, furanopyrryl, furanofuranyl, thienofuranyl, benzoisoxazolyl, benzoisothiazoyl, benzoimidazoyl, o-diazanaphthyl, phenanthrynyl, primidyl, quinazolinoneyl, dibenzothiopheneyl, dibenzofuranyl and combinations thereof.

[0080] Furthermore, Choose from any of the following structures:

[0081]

[0082]

[0083] As an example, the organic compounds of this application may be selected from, but are not limited to, any of the following structures:

[0084]

[0085]

[0086]

[0087]

[0088]

[0089]

[0090]

[0091]

[0092] It is understandable that the H in the structural formula of the above organic compounds can be further substituted.

[0093] The aromatic amine organic compounds according to the present invention have a glass transition temperature Tg ≥ 100℃; preferably, Tg ≥ 120℃; more preferably, Tg ≥ 140℃; even more preferably, Tg ≥ 160℃; and most preferably, Tg ≥ 180℃.

[0094] In some embodiments, the molecular weight of the aromatic amine organic compound is ≤1100 g / mol, preferably ≤1000 g / mol, more preferably ≤950 g / mol, even more preferably ≤900 g / mol, and most preferably ≤800 g / mol. In this case, the aromatic amine organic compound can be deposited into a film using a vapor deposition method.

[0095] In other embodiments, the aromatic amine organic compound has a molecular weight ≥700 g / mol, preferably ≥900 g / mol, more preferably ≥1000 g / mol, and most preferably ≥1100 g / mol. In this case, the aromatic amine organic compound can be formed into a film using a printing method.

[0096] In some embodiments, the organic compounds of this application can be used as organic functional materials in the functional layers of organic electronic devices, particularly in the functional layers of OLED devices. The organic functional materials can be, but are not limited to, hole injection materials (HIM), hole transport materials (HTM), electron transport materials (ETM), electron injection materials (EIM), electron blocking materials (EBM), hole blocking materials (HBM), guest emitters, and host emitters. The host material can be categorized into phosphorescent host materials, fluorescent host materials, and host materials for TADF luminescent materials. The organic compounds of this application can be any one of these.

[0097] In some embodiments, the organic compounds of this application are used in the hole transport layer of organic electronic devices.

[0098] This application also relates to a mixture comprising at least one of the aforementioned organic compounds and at least one other organic functional material. The other organic functional material may be, but is not limited to, hole injection materials, hole transport materials, electron transport materials, electron injection materials, electron blocking materials, hole blocking materials, organic light-emitting guest materials, organic host materials, or inorganic quantum dots known in the art for use in organic electronic devices. Various organic functional materials are described in detail in WO2010135519A1, US20090134784A1, and WO2011110277A1, the entire contents of which are hereby incorporated herein by reference.

[0099] It is understood that the other organic functional material can be a small molecule organic material or a polymer material.

[0100] In some embodiments, the other organic functional material is selected from electron transport materials and is blended with the organic compound described in this application as a co-host material used in the light-emitting layer of organic electronic devices.

[0101] This application also relates to a composition comprising at least one organic compound or mixture as described above, and at least one organic solvent.

[0102] 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.

[0103] In at least one preferred embodiment, the organic solvent in the composition is selected from aromatic or heteroaromatic solvents.

[0104] The aromatic or heteroaromatic solvents may be selected from, but are not limited to, p-diisopropylbenzene, pentamene, tetrahydronaphthalene, cyclohexylbenzene, chloronaphthalene, 1,4-dimethylnaphthalene, 3-isopropylbiphenyl, p-methylisopropylbenzene, dipentene, tripentene, pentamethylene, 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-methylisopropylbenzene, 1-methylnaphthalene, 1,2,4-trichlorobenzene, 4,4-difluorodiphenylmethane, 1,2-dimethoxy-4-(1-propenyl)benzene, diphenylmethane, 2-phenylpyridine, 3-phenylpyridine. At least one of 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-furanate, and ethyl 2-furanate.

[0105] 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.

[0106] 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.

[0107] 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.

[0108] 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.

[0109] It is understood that the organic solvent can be used alone or as a mixture of two or more organic solvents.

[0110] In some embodiments, the composition of this application includes at least one organic compound or mixture as described above, and at least one organic solvent, and may further include another organic solvent.

[0111] 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.

[0112] In some preferred embodiments, the organic solvents suitable for this application are solvents with Hansen solubility parameters within the following ranges:

[0113] 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;

[0114] 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;

[0115] 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.

[0116] 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.

[0117] It is understood that the organic solvent can evaporate from the solvent system to form a thin film comprising the organic compound.

[0118] 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, modifying 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.

[0119] 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 even more preferably 0.25-3 wt%.

[0120] 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.

[0121] This application also provides the application of the organic compound, mixture, or composition as described above in an organic electronic device. The specific solution is as follows:

[0122] An organic electronic device includes at least one functional layer. The functional layer comprises at least one organic compound or mixture as described above, or is prepared from the above-described composition.

[0123] Furthermore, the organic electronic device includes a cathode, an anode, and at least one functional layer. The functional layer comprises at least one organic compound or mixture as described above, or is prepared from the above-described composition.

[0124] The functional layer may be, but is not limited to, a hole injection layer (HIL), a hole transport layer (HTL), a light-emitting layer, an electron blocking layer, an electron injection layer (EIL), an electron transport layer (ETL), or a hole blocking layer. Preferably, the functional layer is a hole transport layer.

[0125] The thickness of the functional layer is 10 nm to 200 nm, preferably 20 nm to 150 nm, more preferably 30 nm to 100 nm, and most preferably 40 nm to 90 nm.

[0126] In some preferred embodiments, the functional layer is a hole transport layer. The hole transport layer may be formed of one layer or two or more layers. When the hole transport layer is formed of one layer, it contains at least one organic compound or mixture as described above, or is prepared from the above-described composition; when the hole transport layer is formed of two or more layers, at least one layer contains at least one organic compound or mixture as described above, or is prepared from the above-described composition, and the other layers may contain hole transport materials known in the art for hole transport layers.

[0127] In a specific 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, a first hole transport layer located between the anode and the light-emitting layer, and a second hole transport layer located between the first hole transport layer and the light-emitting layer, wherein the material of the second hole transport layer is selected from an organic compound or mixture as described above, or a combination thereof.

[0128] Furthermore, the organic electronic device includes an anode, a hole injection layer, a first hole transport layer, a second hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, and a cathode; wherein the material of the second hole transport layer is selected from an organic compound or mixture as described above, or a combination thereof.

[0129] It is understood that the organic electronic device also includes a substrate. The substrate may be located on the side of the anode away from the light-emitting layer, or on the side of the cathode away from the light-emitting layer.

[0130] The substrate is made of materials commonly used in organic electronic devices, such as glass, polyethylene terephthalate (PET), and polyethylene glycol (2,6-naphthalene) (PEN).

[0131] 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 the present invention. 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 may be used as cathode materials for the devices of the present invention. 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.

[0132] 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.

[0133] 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.

[0134] The electron blocking layer can be disposed between the hole transport layer and the light-emitting layer. As the electron blocking layer, compounds based on spiroindolazidine or materials known in the art can be used.

[0135] 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.

[0136] 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.

[0137] 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.

[0138] In one embodiment, the material of the light-emitting layer 40 includes RD and RH (see structural formula below).

[0139] 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.

[0140] 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.

[0141] 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.

[0142] 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.

[0143] 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.

[0144] 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

[0146] The synthetic route for compound 1-1 in the following examples is as follows:

[0147]

[0148] Synthesis of intermediate C:

[0149] Compound A (10 mmol), compound B (10 mmol), and Cs₂CO₃ (30 mmol) were dissolved in DMF and stirred at 150 °C for 24 h under a nitrogen atmosphere. After cooling, the solvent was removed by rotary evaporation, and the mixture was extracted, washed with water, and separated. Organic phase column chromatography was performed to give 8.17 mmol of intermediate C. The yield of intermediate C was 81.7%, and the MS (ASAP) value was 428.0.

[0150] Synthesis of intermediate 1-1:

[0151] Intermediate C (10 mmol), Pd(dba)2 (0.1 mmol), and triethylamine (30 mmol) were dissolved in acetonitrile. The mixture was stirred at 150 °C for 24 h under a nitrogen atmosphere. After cooling, the solvent was removed by rotary evaporation. The extract was then washed with water, and the liquid was separated. Organic phase column chromatography was performed to give 8.49 mmol of intermediate 1-1. The yield of intermediate 1-1 was 84.9%, and the MS (ASAP) value was 348.1.

[0152] Example 1

[0153] The synthetic route of organic compound 1 in this embodiment is as follows:

[0154]

[0155] Synthesis of intermediates 1-2:

[0156] Compound 1-1 (10 mmol) and liquid bromine (10 mmol) were dissolved in dichloromethane and stirred at room temperature for 6 h under a nitrogen atmosphere. After cooling, the solvent was removed by rotary evaporation, the extract was washed with water, and the organic phase was collected. After drying, concentration under reduced pressure, and organic phase column chromatography, intermediate 1-2 was obtained. The molar amount of intermediate 1-2 was 8.71 mmol, the yield was 87.1%, and the MS (ASAP) value was 426.0.

[0157] Synthesis of intermediates 1-4:

[0158] Intermediate 1-2 (10 mmol) and compound 1-3 (10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (2 1 / 2 ml), and Pd(PPh3)4 (0.1 mmol) and potassium carbonate (30 mmol) were added. The mixture was stirred at 100 °C for 6 h under a nitrogen atmosphere. After cooling, most of the solvent was removed by rotary evaporation, followed by extraction and washing with water. The organic phase was collected, dried, concentrated under reduced pressure, and subjected to organic phase column chromatography and recrystallization to obtain intermediate 1-4. The molar amount of intermediate 1-4 was 7.25 mmol, the yield was 72.5%, and the MS (ASAP) value was 362.1.

[0159] Synthesis of intermediates 1-6:

[0160] Intermediate 1-4 (10 mmol), compound 1-5 (10 mmol), Pd(dba)2 (0.1 mmol), TTBP (tri-tert-butylphosphine, 0.2 mmol), and sodium tert-butoxide (30 mmol) were dissolved in toluene. The mixture was stirred at 100 °C for 6 h under a nitrogen atmosphere. After cooling, the solvent was removed by rotary evaporation. The extract was then washed with water, and the organic phase was collected. After drying, concentration under reduced pressure, and organic phase column chromatography, intermediate 1-6 was obtained. The molar amount of intermediate 1-6 was 6.37 mmol, the yield was 63.7%, and the MS (ASAP) value was 514.2.

[0161] Synthesis of Organic Compound 1:

[0162] Intermediates 1-6 (10 mmol), compounds 1-7 (10 mmol), Pd(dba)2 (0.1 mmol), TTBP (0.2 mmol), and sodium tert-butoxide (30 mmol) were dissolved in toluene. The mixture was stirred at 100 °C for 6 h under a nitrogen atmosphere. After cooling, the solvent was removed by rotary evaporation. The extract was then washed with water, and the organic phase was collected. After drying, concentration under reduced pressure, and column chromatography, organic compound 1 was obtained. The yield of organic compound 1 was 70.4%, and the MS (ASAP) value was 706.2.

[0163] Example 2

[0164] The synthetic route for organic compound 2 in this embodiment is as follows:

[0165]

[0166] Synthesis of intermediate 2-2:

[0167] Intermediate 1-2 (10 mmol) and compound 2-1 (10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (2 1 / 2 ml), and Pd(PPh3)4 (0.1 mmol) and potassium carbonate (30 mmol) were added. The mixture was stirred at 100 °C for 6 h under a nitrogen atmosphere. After cooling, most of the solvent was removed by rotary evaporation. The mixture was then extracted, washed with water, and the organic phase was collected. After drying, concentration under reduced pressure, and organic phase column chromatography followed by recrystallization, intermediate 2-2 was obtained. The molar amount of intermediate 2-2 was 6.59 mmol, the yield was 65.9%, and the MS (ASAP) value was 424.1.

[0168] Synthesis of intermediates 2-3:

[0169] Intermediate 2-2 (10 mmol), compound 1-5 (10 mmol), Pd(dba)2 (0.1 mmol), TTBP (0.2 mmol), and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100 °C for 6 h under a nitrogen atmosphere. After cooling, the solvent was removed by rotary evaporation, the extract was obtained, washed with water, and the organic phase was collected. After drying, concentration under reduced pressure, and organic phase column chromatography, intermediate 2-3 was obtained. The molar amount of intermediate 2-3 was 7.09 mmol, the yield was 70.9%, and the MS (ASAP) value was 576.2.

[0170] Synthesis of organic compound 2:

[0171] Intermediate 2-3 (10 mmol), compounds 1-7 (10 mmol), Pd(dba)2 (0.1 mmol), TTBP (0.2 mmol), and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100 °C for 6 h under a nitrogen atmosphere. After cooling, the solvent was removed by rotary evaporation, the extract was washed with water, and the organic phase was collected. After drying, concentration under reduced pressure, and organic phase column chromatography, organic compound 2 was obtained. The yield of organic compound 2 was 63.8%, and MS (ASAP) = 768.3.

[0172] Example 3

[0173] The synthetic route of organic compound 3 in this embodiment is as follows:

[0174]

[0175] Synthesis of organic compound 3:

[0176] Intermediate 1-4 (10 mmol), compound 1-7 (20 mmol), Pd(dba)2 (0.1 mmol), TTBP (0.2 mmol), and sodium tert-butoxide (30 mmol) were dissolved in toluene. The mixture was stirred at 100 °C for 6 h under a nitrogen atmosphere. After cooling, the solvent was removed by rotary evaporation. The extract was then washed with water, and the organic phase was collected. After drying, concentration under reduced pressure, and column chromatography, organic compound 3 was obtained. The yield of organic compound 3 was 54.8%, and the MS (ASAP) value was 746.3.

[0177] Example 4

[0178] The synthetic route for organic compound 4 in this embodiment is as follows:

[0179]

[0180] Synthesis of organic compound 4:

[0181] Intermediate 2-2 (10 mmol), compounds 1-7 (20 mmol), Pd(dba)2 (0.1 mmol), TTBP (0.2 mmol), and sodium tert-butoxide (30 mmol) were dissolved in toluene. The mixture was stirred at 100 °C for 6 h under a nitrogen atmosphere. After cooling, the solvent was removed by rotary evaporation. The extract was then washed with water, and the organic phase was collected. After drying, concentration under reduced pressure, and column chromatography, organic compound 4 was obtained. The yield of organic compound 4 was 73.4%, and the MS (ASAP) value was 808.3.

[0182] Example 5

[0183] The synthetic route of organic compound 5 in this embodiment is as follows:

[0184]

[0185] Synthesis of intermediate 5-2:

[0186] Intermediate 1-4 (10 mmol), compound 5-1 (10 mmol), Pd(dba)2 (0.1 mmol), TTBP (0.2 mmol), and sodium tert-butoxide (30 mmol) were dissolved in toluene. The mixture was stirred at 100 °C for 6 h under a nitrogen atmosphere. After cooling, the solvent was removed by rotary evaporation. The extract was then washed with water, and the organic phase was collected. After drying, concentration under reduced pressure, and organic phase column chromatography, intermediate 5-2 was obtained. The molar amount of intermediate 5-2 was 7.18 mmol, the yield was 71.8%, and the MS (ASAP) value was 603.2.

[0187] Synthesis of organic compound 5:

[0188] Intermediate 5-2 (10 mmol), compounds 1-7 (10 mmol), Pd(dba)2 (0.1 mmol), TTBP (0.2 mmol), and sodium tert-butoxide (30 mmol) were dissolved in toluene. The mixture was stirred at 100 °C for 6 h under a nitrogen atmosphere. After cooling, the solvent was removed by rotary evaporation. The extract was then washed with water, and the organic phase was collected. After drying, concentration under reduced pressure, and column chromatography, organic compound 5 was obtained. The yield of organic compound 5 was 72.9%, and the MS (ASAP) value was 795.3.

[0189] Example 6

[0190] The synthetic route for organic compound 6 in this embodiment is as follows:

[0191]

[0192] Synthesis of intermediate 6-1:

[0193] Intermediate 2-2 (10 mmol), compound 5-1 (10 mmol), Pd(dba)2 (0.1 mmol), TTBP (0.2 mmol), and sodium tert-butoxide (30 mmol) were dissolved in toluene. The mixture was stirred at 100 °C for 6 h under a nitrogen atmosphere. After cooling, the solvent was removed by rotary evaporation. The extract was then washed with water, and the organic phase was collected. After drying, concentration under reduced pressure, and organic phase column chromatography, intermediate 6-1 was obtained. The molar amount of intermediate 6-1 was 6.38 mmol, the yield was 63.8%, and the MS (ASAP) value was 665.2.

[0194] Synthesis of organic compound 6:

[0195] Intermediate 6-1 (10 mmol), compounds 1-7 (10 mmol), Pd(dba)2 (0.1 mmol), TTBP (0.2 mmol), and sodium tert-butoxide (30 mmol) were dissolved in toluene. The mixture was stirred at 100 °C for 6 h under a nitrogen atmosphere. After cooling, the solvent was removed by rotary evaporation. The extract was then washed with water, and the organic phase was collected. After drying, concentration under reduced pressure, and organic phase column chromatography, organic compound 6 was obtained. The yield of organic compound 6 was 68.6%, and the MS (ASAP) value was 857.3.

[0196] Example 7

[0197] The synthetic route for organic compound 7 in this embodiment is as follows:

[0198]

[0199] Synthesis of intermediate 7-1:

[0200] Compound 1-1 (10 mmol) and liquid bromine (20 mmol) were dissolved in dichloromethane and stirred at room temperature for 6 h under a nitrogen atmosphere. After cooling, the solvent was removed by rotary evaporation, and the mixture was extracted, washed with water, and separated. The organic phase was collected, dried, concentrated under reduced pressure, and subjected to organic phase column chromatography to give intermediate 7-1. The molar amount of intermediate 7-1 was 8.43 mmol, the yield was 84.3%, and the MS (ASAP) value was 503.9.

[0201] Synthesis of intermediate 7-2:

[0202] Intermediate 7-1 (10 mmol) and compound 1-3 (20 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (2 1 / 2 ml), and Pd(PPh3)4 (0.1 mmol) and potassium carbonate (30 mmol) were added. The mixture was stirred at 100 °C for 6 h under a nitrogen atmosphere. After cooling, most of the solvent was removed by rotary evaporation. The mixture was then extracted, washed with water, and the organic phase was collected. This organic phase was dried, concentrated under reduced pressure, and subjected to organic phase column chromatography followed by recrystallization to obtain intermediate 7-2. The molar amount of intermediate 7-2 was 6.33 mmol, the yield was 63.3%, and the MS (ASAP) value was 376.1.

[0203] Synthesis of Organic Compound 7:

[0204] Intermediate 7-2 (10 mmol), compound 7-3 (20 mmol), Pd(dba)2 (0.1 mmol), TTBP (0.2 mmol), and sodium tert-butoxide (30 mmol) were dissolved in toluene. The mixture was stirred at 100 °C for 6 h under a nitrogen atmosphere. After cooling, the solvent was removed by rotary evaporation. The extract was then washed with water, and the organic phase was collected. After drying, concentration under reduced pressure, and organic phase column chromatography, organic compound 7 was obtained. The yield of organic compound 7 was 54.8%, and MS (ASAP) = 708.2.

[0205] Example 8

[0206] The synthetic route for organic compound 8 in this embodiment is as follows:

[0207]

[0208] Synthesis of organic compound 8:

[0209] Intermediate 7-2 (10 mmol), compound 8-1 (20 mmol), Pd(dba)2 (0.1 mmol), TTBP (0.2 mmol), and sodium tert-butoxide (30 mmol) were dissolved in toluene. The mixture was stirred at 100 °C for 6 h under a nitrogen atmosphere. After cooling, the solvent was removed by rotary evaporation. The extract was then washed with water, and the organic phase was collected. After drying, concentration under reduced pressure, and organic phase column chromatography, organic compound 8 was obtained. The yield of organic compound 8 was 62.5%, and MS (ASAP) = 740.1.

[0210] Example 9

[0211] The synthetic route for organic compound 9 in this embodiment is as follows:

[0212]

[0213] Synthesis of intermediate 9-2:

[0214] Intermediate 7-1 (10 mmol) and compound 9-1 (20 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (2 1 / 2 ml), and Pd(PPh3)4 (0.1 mmol) and potassium carbonate (30 mmol) were added. The mixture was stirred at 100 °C for 6 h under a nitrogen atmosphere. After cooling, most of the solvent was removed by rotary evaporation, followed by extraction and washing with water. The organic phase was collected, dried, concentrated under reduced pressure, and subjected to organic phase column chromatography and recrystallization to obtain intermediate 9-2. The molar amount of intermediate 9-2 was 7.33 mmol, the yield was 73.3%, and the MS (ASAP) value was 404.1.

[0215] Synthesis of intermediate 9-3:

[0216] Intermediate 9-2 (10 mmol), compound 1-5 (10 mmol), Pd(dba)2 (0.1 mmol), TTBP (0.2 mmol), and sodium tert-butoxide (30 mmol) were dissolved in toluene. The mixture was stirred at 100 °C for 6 h under a nitrogen atmosphere. After cooling, the solvent was removed by rotary evaporation. The extract was then washed with water, and the organic phase was collected. After drying, concentration under reduced pressure, and organic phase column chromatography, intermediate 9-3 was obtained. The molar amount of intermediate 9-3 was 8.35 mmol, the yield was 83.5%, and the MS (ASAP) value was 556.2.

[0217] Synthesis of Organic Compound 9:

[0218] Intermediate 9-3 (10 mmol), compound 9-4 (10 mmol), Pd(dba)2 (0.1 mmol), TTBP (0.2 mmol), and sodium tert-butoxide (30 mmol) were dissolved in toluene. The mixture was stirred at 100 °C for 6 h under a nitrogen atmosphere. After cooling, the solvent was removed by rotary evaporation. The extract was then washed with water, and the organic phase was collected. After drying, concentration under reduced pressure, and column chromatography, organic compound 9 was obtained. The yield of organic compound 9 was 45.3%, and the MS (ASAP) value was 682.2.

[0219] Example 10

[0220] The synthetic route of organic compound 10 in this embodiment is as follows:

[0221]

[0222] Synthesis of organic compound 10:

[0223] Intermediate 9-3 (10 mmol), compound 10-1 (10 mmol), Pd(dba)2 (0.1 mmol), TTBP (0.2 mmol), and sodium tert-butoxide (30 mmol) were dissolved in toluene. The mixture was stirred at 100 °C for 6 h under a nitrogen atmosphere. After cooling, the solvent was removed by rotary evaporation. The extract was then washed with water, and the organic phase was collected. After drying, concentration under reduced pressure, and organic phase column chromatography, organic compound 10 was obtained. The yield of organic compound 10 was 71.7%, and the MS (ASAP) value was 632.2.

[0224] Example 11

[0225] The synthetic route of organic compound 11 in this embodiment is as follows:

[0226]

[0227] Synthesis of intermediate 11-2:

[0228] Intermediate 1-2 (10 mmol) and compound 11-1 (10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (2 1 / 2 ml), and Pd(PPh3)4 (0.1 mmol) and potassium carbonate (30 mmol) were added. The mixture was stirred at 100 °C for 6 h under a nitrogen atmosphere. After cooling, most of the solvent was removed by rotary evaporation. The mixture was then extracted, washed with water, and the organic phase was collected. After drying, concentration under reduced pressure, and organic phase column chromatography followed by recrystallization, intermediate 11-2 was obtained. The molar amount of intermediate 11-2 was 7.54 mmol, the yield was 75.4%, and the MS (ASAP) value was 438.1.

[0229] Synthesis of organic compound 11:

[0230] Intermediate 11-2 (10 mmol), compound 9-4 (20 mmol), Pd(dba)2 (0.1 mmol), TTBP (0.2 mmol), and sodium tert-butoxide (30 mmol) were dissolved in toluene. The mixture was stirred at 100 °C for 6 h under a nitrogen atmosphere. After cooling, the solvent was removed by rotary evaporation. The extract was then washed with water, and the organic phase was collected. After drying, concentration under reduced pressure, and organic phase column chromatography, organic compound 11 was obtained. The yield of organic compound 11 was 71.3%, and the MS (ASAP) value was 690.2.

[0231] Example 12

[0232] The synthetic route of organic compound 12 in this embodiment is as follows:

[0233]

[0234] Synthesis of intermediate 12-1:

[0235] Intermediate 11-2 (10 mmol), compound 10-1 (10 mmol), Pd(dba)2 (0.1 mmol), TTBP (0.2 mmol), and sodium tert-butoxide (30 mmol) were dissolved in toluene. The mixture was stirred at 100 °C for 6 h under a nitrogen atmosphere. After cooling, the solvent was removed by rotary evaporation. The extract was then washed with water, and the organic phase was collected. After drying, concentration under reduced pressure, and organic phase column chromatography, intermediate 12-1 was obtained. The molar amount of intermediate 12-1 was 8.06 mmol, the yield was 80.6%, and the MS (ASAP) value was 514.2.

[0236] Synthesis of organic compound 12:

[0237] Intermediate 12-1 (10 mmol), compound 12-2 (10 mmol), Pd(dba)2 (0.1 mmol), TTBP (0.2 mmol), and sodium tert-butoxide (30 mmol) were dissolved in toluene. The mixture was stirred at 100 °C for 6 h under a nitrogen atmosphere. After cooling, the solvent was removed by rotary evaporation. The extract was then washed with water, and the organic phase was collected. After drying, concentration under reduced pressure, and column chromatography, organic compound 12 was obtained. The yield of organic compound 12 was 61.8%, and the MS (ASAP) value was 690.2.

[0238] Example 13

[0239] The synthetic route of organic compound 13 in this embodiment is as follows:

[0240]

[0241] Synthesis of intermediate 13-2:

[0242] Intermediate 1-2 (10 mmol) and compound 13-1 (10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (2 1 / 2 ml), and Pd(PPh3)4 (0.1 mmol) and potassium carbonate (30 mmol) were added. The mixture was stirred at 100 °C for 6 h under a nitrogen atmosphere. After cooling, most of the solvent was removed by rotary evaporation. The mixture was then extracted, washed with water, and the organic phase was collected. After drying, concentration under reduced pressure, and organic phase column chromatography followed by recrystallization, intermediate 13-2 was obtained. The molar amount of intermediate 13-2 was 5.73 mmol, the yield was 57.3%, and the MS (ASAP) value was 404.1.

[0243] Synthesis of intermediate 13-3:

[0244] Intermediate 13-2 (10 mmol), compound 1-5 (10 mmol), Pd(dba)2 (0.1 mmol), TTBP (0.2 mmol), and sodium tert-butoxide (30 mmol) were dissolved in toluene. The mixture was stirred at 100 °C for 6 h under a nitrogen atmosphere. After cooling, the solvent was removed by rotary evaporation. The extract was then washed with water, and the organic phase was collected. After drying, concentration under reduced pressure, and organic phase column chromatography, intermediate 13-3 was obtained. The molar amount of intermediate 13-3 was 6.84 mmol, the yield was 68.4%, and the MS (ASAP) value was 556.2.

[0245] Synthesis of organic compound 13:

[0246] Intermediate 13-3 (10 mmol), compound 13-4 (10 mmol), Pd(dba)2 (0.1 mmol), TTBP (0.2 mmol), and sodium tert-butoxide (30 mmol) were dissolved in toluene. The mixture was stirred at 100 °C for 6 h under a nitrogen atmosphere. After cooling, the solvent was removed by rotary evaporation. The extract was then washed with water, and the organic phase was collected. After drying, concentration under reduced pressure, and column chromatography, organic compound 13 was obtained. The yield of organic compound 13 was 73.4%, and the MS (ASAP) value was 758.3.

[0247] Example 14

[0248] The synthetic route of organic compound 14 in this embodiment is as follows:

[0249]

[0250] Synthesis of organic compound 14:

[0251] Intermediate 13-3 (10 mmol), compound 14-1 (10 mmol), Pd(dba)2 (0.1 mmol), TTBP (0.2 mmol), and sodium tert-butoxide (30 mmol) were dissolved in toluene. The mixture was stirred at 100 °C for 6 h under a nitrogen atmosphere. After cooling, the solvent was removed by rotary evaporation. The extract was then washed with water, and the organic phase was collected. After drying, concentration under reduced pressure, and column chromatography, organic compound 14 was obtained. The yield of organic compound 14 was 69.5%, and the MS (ASAP) value was 808.3.

[0252] Example 15

[0253] The synthetic route of organic compound 15 in this embodiment is as follows:

[0254]

[0255] Synthesis of intermediate 15-2:

[0256] Intermediate 1-2 (10 mmol) and compound 15-1 (10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (2 1 / 2 ml), and Pd(PPh3)4 (0.1 mmol) and potassium carbonate (30 mmol) were added. The mixture was stirred at 100 °C for 6 h under a nitrogen atmosphere. After cooling, most of the solvent was removed by rotary evaporation. The mixture was then extracted, washed with water, and the organic phase was collected. After drying, concentration under reduced pressure, and organic phase column chromatography followed by recrystallization, intermediate 15-2 was obtained. The molar amount of intermediate 15-2 was 5.87 mmol, the yield was 58.7%, and the MS (ASAP) value was 390.1.

[0257] Synthesis of intermediate 15-4:

[0258] Intermediate 15-2 (10 mmol), compound 15-3 (10 mmol), Pd(dba)2 (0.1 mmol), TTBP (0.2 mmol), and sodium tert-butoxide (30 mmol) were dissolved in toluene. The mixture was stirred at 100 °C for 6 h under a nitrogen atmosphere. After cooling, the solvent was removed by rotary evaporation. The mixture was extracted, washed with water, and the organic phase was collected. After drying, concentration under reduced pressure, and organic phase column chromatography, intermediate 15-4 was obtained with a molar amount of 6.49 mmol and a yield of 64.9%. MS (ASAP) = 542.2.

[0259] Synthesis of organic compound 15:

[0260] Intermediate 15-4 (10 mmol), compound 10-1 (10 mmol), Pd(dba)2 (0.1 mmol), TTBP (0.2 mmol), and sodium tert-butoxide (30 mmol) were dissolved in toluene. The mixture was stirred at 100 °C for 6 h under a nitrogen atmosphere. After cooling, the solvent was removed by rotary evaporation. The extract was then washed with water, and the organic phase was collected. After drying, concentration under reduced pressure, and organic phase column chromatography, organic compound 15 was obtained. The yield of organic compound 15 was 70.2%, and the MS (ASAP) value was 618.2.

[0261] Example 16

[0262] The synthetic route for organic compound 16 in this embodiment is as follows:

[0263]

[0264] Synthesis of organic compound 16:

[0265] Intermediate 15-2 (10 mmol), compound 1-5 (20 mmol), Pd(dba)2 (0.1 mmol), TTBP (0.2 mmol), and sodium tert-butoxide (30 mmol) were dissolved in toluene. The mixture was stirred at 100 °C for 6 h under a nitrogen atmosphere. After cooling, the solvent was removed by rotary evaporation. The extract was then washed with water, and the organic phase was collected. After drying, concentration under reduced pressure, and column chromatography, organic compound 16 was obtained. The yield of organic compound 16 was 58.1%, and the MS (ASAP) value was 694.2.

[0266] Example 17

[0267] The synthetic route for organic compound 17 in this embodiment is as follows:

[0268]

[0269] Synthesis of intermediate 17-2:

[0270] Magnesium shavings (50 mmol), 200 mL of THF, and 5 grains of I2 were added to a dry, anhydrous two-necked flask. After purging with nitrogen three times, a 10 mmol THF solution of intermediate 7-1 was slowly added dropwise. After initiation, the system was allowed to return to room temperature for 0.5 h. Then, the system solution was added dropwise to a 20 mmol THF solution of intermediate 17-1, and stirred at room temperature. During the treatment, the Grignard reagent was quenched with water. After the temperature stabilized, the mixture was extracted, washed with water, and the organic phase was collected. After drying, concentration under reduced pressure, and organic phase column chromatography followed by recrystallization, intermediate 17-2 was obtained. The molar amount of intermediate 17-2 was 7.33 mmol, the yield was 73.3%, and the MS (ASAP) was 414.6.

[0271] Synthesis of intermediate 17-3:

[0272] Intermediate 17-2 (10 mmol), compound 1-5 (10 mmol), Pd(dba)2 (0.1 mmol), TTBP (0.2 mmol), and sodium tert-butoxide (30 mmol) were dissolved in toluene. The mixture was stirred at 100 °C for 6 h under a nitrogen atmosphere. After cooling, the solvent was removed by rotary evaporation. The extract was then washed with water, and the organic phase was collected. After drying, concentration under reduced pressure, and organic phase column chromatography, intermediate 17-3 was obtained. The molar amount of intermediate 17-3 was 8.17 mmol, the yield was 81.7%, and the MS (ASAP) value was 566.4.

[0273] Synthesis of organic compound 17:

[0274] Intermediate 17-3 (10 mmol), compound 7-3 (10 mmol), Pd(dba)2 (0.1 mmol), TTBP (0.2 mmol), and sodium tert-butoxide (30 mmol) were dissolved in toluene. The mixture was stirred at 100 °C for 6 h under a nitrogen atmosphere. After cooling, the solvent was removed by rotary evaporation. The extract was then washed with water, and the organic phase was collected. After drying, concentration under reduced pressure, and organic phase column chromatography, organic compound 17 was obtained. The yield of organic compound 17 was 52.4%, and the MS (ASAP) value was 732.1.

[0275] Example 18

[0276] The synthetic route of organic compound 18 in this embodiment is as follows:

[0277]

[0278] Synthesis of intermediate 18-1:

[0279] Intermediate 7-1 (10 mmol) and compound 15-1 (20 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (2 1 / 2 ml), and Pd(PPh3)4 (0.1 mmol) and potassium carbonate (30 mmol) were added. The mixture was stirred at 100 °C for 6 h under a nitrogen atmosphere. After cooling, most of the solvent was removed by rotary evaporation, followed by extraction and washing with water. The organic phase was collected, dried, concentrated under reduced pressure, and subjected to organic phase column chromatography and recrystallization to obtain intermediate 18-1. The molar amount of intermediate 18-1 was 6.34 mmol, the yield was 63.4%, and the MS (ASAP) value was 432.5.

[0280] Synthesis of organic compound 18:

[0281] Intermediate 18-1 (10 mmol), compound 18-2 (20 mmol), Pd(dba)2 (0.1 mmol), TTBP (0.2 mmol), and sodium tert-butoxide (30 mmol) were dissolved in toluene. The mixture was stirred at 100 °C for 6 h under a nitrogen atmosphere. After cooling, the solvent was removed by rotary evaporation. The extract was then washed with water, and the organic phase was collected. After drying, concentration under reduced pressure, and column chromatography, organic compound 18 was obtained. The yield of organic compound 18 was 60.8%, and the MS (ASAP) value was 914.7.

[0282] Example 19

[0283] The synthetic route of organic compound 19 in this embodiment is as follows:

[0284]

[0285] Synthesis of intermediate 19-2:

[0286] Intermediate 19-1 (10 mmol), compound 1-5 (10 mmol), Pd(dba)2 (0.1 mmol), TTBP (0.2 mmol), and sodium tert-butoxide (30 mmol) were dissolved in toluene. The mixture was stirred at 100 °C for 6 h under a nitrogen atmosphere. After cooling, the solvent was removed by rotary evaporation. The extract was then washed with water, and the organic phase was collected. After drying, concentration under reduced pressure, and organic phase column chromatography, intermediate 19-2 was obtained. The molar amount of intermediate 19-2 was 7.39 mmol, the yield was 73.9%, and the MS (ASAP) value was 337.7.

[0287] Synthesis of intermediate 19-4:

[0288] Compounds 19-2 (10 mmol), 19-3 (10 mmol), and Cs₂CO₃ (30 mmol) were dissolved in DMF and stirred at 150 °C for 24 h under a nitrogen atmosphere. After cooling, the solvent was removed by rotary evaporation, and the mixture was extracted, washed with water, and separated. Organic phase column chromatography was performed to give intermediate 19-4 in a molar amount of 6.84 mmol, with a yield of 68.4%. MS (ASAP) = 552.7.

[0289] Synthesis of intermediate 19-5:

[0290] Compound 19-4 (10 mmol), Pd(dba)2 (0.1 mmol) and triethylamine (30 mmol) were dissolved in acetonitrile. The mixture was stirred at 150 °C for 24 h under a nitrogen atmosphere. After cooling, the solvent was removed by rotary evaporation. The mixture was extracted, washed with water, and separated. Organic phase column chromatography was performed to give intermediate 19-5. The molar amount of intermediate 19-5 was 7.45 mmol, the yield was 74.5%, and the MS (ASAP) value was 424.7.

[0291] Synthesis of intermediate 19-6:

[0292] Compound 19-5 (10 mmol) and liquid bromine (20 mmol) were dissolved in dichloromethane and stirred at room temperature for 6 h under a nitrogen atmosphere. After cooling, the solvent was removed by rotary evaporation, and the extract was washed with water and separated. The organic phase was collected, dried, concentrated under reduced pressure, and subjected to organic phase column chromatography to give intermediate 19-6. The molar amount of intermediate 19-6 was 7.13 mmol, the yield was 71.3%, and the MS (ASAP) value was 580.4.

[0293] Synthesis of intermediate 19-7:

[0294] Intermediate 19-6 (10 mmol) and compound 2-1 (20 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (2 1 / 2 ml), and Pd(PPh3)4 (0.1 mmol) and potassium carbonate (30 mmol) were added. The mixture was stirred at 100 °C for 6 h under a nitrogen atmosphere. After cooling, most of the solvent was removed by rotary evaporation. The mixture was then extracted, washed with water, and the organic phase was collected. After drying, concentration under reduced pressure, and organic phase column chromatography followed by recrystallization, intermediate 19-7 was obtained. The molar amount of intermediate 19-7 was 5.36 mmol, the yield was 53.6%, and the MS (ASAP) value was 576.8.

[0295] Synthesis of intermediate 19-8:

[0296] Intermediate 19-7 (10 mmol), compound 10-1 (10 mmol), Pd(dba)2 (0.1 mmol), TTBP (0.2 mmol), and sodium tert-butoxide (30 mmol) were dissolved in toluene. The mixture was stirred at 100 °C for 6 h under a nitrogen atmosphere. After cooling, the solvent was removed by rotary evaporation. The extract was then washed with water, and the organic phase was collected. After drying, concentration under reduced pressure, and organic phase column chromatography, intermediate 19-8 was obtained. The molar amount of intermediate 19-8 was 6.87 mmol, the yield was 68.7%, and the MS (ASAP) value was 652.7.

[0297] Synthesis of organic compound 19:

[0298] Intermediate 19-8 (10 mmol), compounds 1-5 (10 mmol), Pd(dba)2 (0.1 mmol), TTBP (0.2 mmol), and sodium tert-butoxide (30 mmol) were dissolved in toluene. The mixture was stirred at 100 °C for 6 h under a nitrogen atmosphere. After cooling, the solvent was removed by rotary evaporation. The extract was then washed with water, and the organic phase was collected. After drying, concentration under reduced pressure, and organic phase column chromatography, organic compound 19 was obtained. The yield of organic compound 19 was 74.3%, and the MS (ASAP) value was 804.7.

[0299] Example 20

[0300] The synthetic route of organic compound 20 in this embodiment is as follows:

[0301]

[0302] Synthesis of intermediate 20-1:

[0303] Intermediate 19-1 (10 mmol), compound 9-4 (10 mmol), Pd(dba)2 (0.1 mmol), TTBP (0.2 mmol), and sodium tert-butoxide (30 mmol) were dissolved in toluene. The mixture was stirred at 100 °C for 6 h under a nitrogen atmosphere. After cooling, the solvent was removed by rotary evaporation. The extract was then washed with water, and the organic phase was collected. After drying, concentration under reduced pressure, and organic phase column chromatography, intermediate 20-1 was obtained. The molar amount of intermediate 20-1 was 7.59 mmol, the yield was 75.9%, and the MS (ASAP) value was 311.6.

[0304] Synthesis of intermediate 20-2:

[0305] Compounds 20-1 (10 mmol), 19-3 (10 mmol), and Cs₂CO₃ (30 mmol) were dissolved in DMF and stirred at 150 °C for 24 h under a nitrogen atmosphere. After cooling, the solvent was removed by rotary evaporation, and the mixture was extracted, washed with water, and separated. Organic phase column chromatography was performed to give intermediate 20-2. The molar amount of intermediate 20-2 was 6.15 mmol, the yield was 61.5%, and the MS (ASAP) value was 526.5.

[0306] Synthesis of intermediate 20-3:

[0307] Compound 20-2 (10 mmol), Pd(dba)2 (0.1 mmol), and triethylamine (30 mmol) were dissolved in acetonitrile. The mixture was stirred at 150 °C for 24 h under a nitrogen atmosphere. After cooling, the solvent was removed by rotary evaporation. The extract was then washed with water, and the liquid was separated. Organic phase column chromatography was performed to give intermediate 20-3. The molar amount of intermediate 20-3 was 5.24 mmol, the yield was 52.4%, and the MS (ASAP) value was 398.4.

[0308] Synthesis of intermediate 20-4:

[0309] Compound 20-3 (10 mmol) and liquid bromine (10 mmol) were dissolved in dichloromethane. The mixture was stirred at room temperature under a nitrogen atmosphere for 6 h. After cooling, the solvent was removed by rotary evaporation. The extract was then washed with water, and the organic phase was collected. After drying, concentration under reduced pressure, and organic phase column chromatography, intermediate 20-4 was obtained. The molar amount of intermediate 20-4 was 5.21 mmol, the yield was 52.1%, and the MS (ASAP) value was 476.8.

[0310] Synthesis of intermediate 20-6:

[0311] Magnesium shavings (50 mmol), 200 mL of THF, and 5 grains of I₂ were added to a dry, anhydrous two-necked flask. After purging with nitrogen three times, a 10 mmol THF solution of intermediate 20⁻⁴ was slowly added dropwise. After initiation, the system was allowed to return to room temperature for 0.5 h. Then, the system solution was added dropwise to a 10 mmol THF solution of intermediate 20⁻⁵, and stirred at room temperature. During the treatment, the Grignard reagent was quenched with water. After the temperature stabilized, the mixture was extracted, washed with water, and the organic phase was collected. After drying, concentration under reduced pressure, and organic phase column chromatography followed by recrystallization, intermediate 20⁻⁶ was obtained. The molar amount of intermediate 20⁻⁶ was 7.96 mmol, the yield was 79.6%, and the MS (ASAP) was 415.1.

[0312] Synthesis of organic compound 20:

[0313] Intermediate 20-6 (10 mmol), compound 1-5 (20 mmol), Pd(dba)2 (0.1 mmol), TTBP (0.2 mmol), and sodium tert-butoxide (30 mmol) were dissolved in toluene. The mixture was stirred at 100 °C for 6 h under a nitrogen atmosphere. After cooling, the solvent was removed by rotary evaporation. The extract was then washed with water, and the organic phase was collected. After drying, concentration under reduced pressure, and column chromatography, organic compound 20 was obtained. The yield of organic compound 20 was 83.2%, and the MS (ASAP) value was 719.6.

[0314] Comparative Example 1

[0315] The organic compound in this comparative example is Ref-1, and its chemical structural formula is as follows:

[0316]

[0317] Comparative Example 2

[0318] The organic compound in this comparative example is Ref-2, and its chemical structural formula is as follows:

[0319]

[0320] Energy level calculation of organic compounds

[0321] Calculate the HOMO, LUMO, and E levels of the organic compounds in Examples 1-20 and Comparative Examples 1-2. T1 and E S1The calculation method is as follows: Using TD-DFT (time-dependent density functional theory) via Gaussian09W (Gaussian Inc.), the specific simulation method can be found in WO2011141110. First, the molecular geometry is optimized using the semi-empirical method "Ground State / Semi-empirical / Default Spin / AM1" (Charge 0 / Spin Singlet). Then, the energy structure of the organic molecule is calculated using TD-DFT (time-dependent density functional theory) to obtain "TD-SCF / DFT / Default Spin / B3PW91" and the basis set "6-31G(d)" (Charge 0 / Spin Singlet). The HOMO and LUMO energy levels are calculated according to the following calibration formula, E... T1 and E S1 Use directly.

[0322] HOMO(eV)=((HOMO(G)×27.212)-0.9899) / 1.1206;

[0323] LUMO(eV)=((LUMO(G)×27.212)-2.0041) / 1.385.

[0324] HOMO and LUMO are direct calculation results from Gaussian 09W, in Hartree units. See Table 1 below for the results.

[0325] Table 1:

[0326] Example compound HOMO[eV] LUMO[eV] <![CDATA[E T1 [eV]]> <![CDATA[E S1 [eV]]> Example 1 Organic compound 1 -5.13 -2.10 2.64 3.20 Example 2 Organic compound 2 -5.16 -2.25 2.61 3.08 Example 3 Organic compound 3 -5.01 -2.10 2.65 3.17 Example 4 Organic compound 4 -5.06 -2.13 2.63 2.94 Example 5 Organic compound 5 -5.04 -2.05 2.68 2.95 Example 6 Organic compound 6 -5.04 -2.12 2.65 2.93 Example 7 Organic compound 7 -5.12 -2.10 2.54 3.09 Example 8 Organic compound 8 -5.17 -2.11 2.59 2.99 Example 9 Organic compound 9 -5.10 -2.05 2.61 2.96 Example 10 Organic compound 10 -5.04 -2.01 2.59 2.91 Example 11 Organic compound 11 -5.09 -2.14 2.70 3.08 Example 12 Organic compound 12 -5.05 -2.13 2.65 3.13 Example 13 Organic compound 13 -5.03 -2.03 2.61 3.08 Example 14 Organic compound 14 -5.00 -2.14 2.59 2.91 Example 15 Organic compound 15 -5.01 -2.05 2.61 3.05 Example 16 Organic compound 16 -5.09 -2.18 2.59 2.91 Example 17 Organic compound 17 -5.05 -2.20 2.57 3.01 Example 18 Organic compound 18 -5.10 -2.13 2.58 2.93 Example 19 Organic compound 19 -5.11 -2.08 2.62 3.02 Example 20 Organic compounds 20 -5.08 -2.10 2.61 2.94 Comparative Example 1 Organic compound Ref-1 -5.03 -1.78 2.89 2.96 Comparative Example 2 Organic compound Ref-2 -5.05 -1.81 2.87 2.93

[0327] OLED device fabrication and performance testing

[0328] The fabrication process of the OLED-1 device using the above-mentioned compound is described in detail below through specific embodiments. The structure of the OLED-1 device is: ITO / HIL / HTL-1 / HTL-2 / EML / ETL / EIL / cathode. A schematic diagram of the OLED-1 device is shown below. Figure 1 As shown, 10 is the substrate, 20 is the anode, 30 is the hole injection layer (HIL), 40 is the first hole transport layer (HTL-1), 50 is the second hole transport layer (HTL-2), 60 is the light-emitting layer, 70 is the electron transport layer (ETL), 80 is the electron injection layer (EIL), and 90 is the cathode.

[0329] The preparation steps are as follows:

[0330] a. Provide an ITO conductive glass substrate, clean the substrate with a cleaning agent, and then perform ultraviolet ozone treatment. The cleaning agent may be, but is not limited to, one or more of chloroform, acetone or isopropanol.

[0331] b. HIL (Hole Injection Layer, 10nm): An ITO conductive glass substrate is transferred into a vacuum vapor deposition apparatus and deposited under high vacuum (1×10⁻⁶ nm). -6 At millibars, resistance heating is used for evaporation to sequentially form HATCN with a thickness of 10 nm, forming a hole injection layer;

[0332] c. HTL-1 (First Hole Transport Layer, 80nm): On the hole injection layer, a vacuum evaporation process (1×10⁻⁶ nm) is used to deposit... -6 The first hole transport material HT-1 (NPB) was deposited by vapor deposition using a millibar method.

[0333] d. HTL-2 (Second Hole Transport Layer, 30nm): Deposited on the first hole transport layer using vacuum evaporation (1×10⁻⁶ nm). -6 Organic compound 1 in Example 1 was deposited as a second hole transport material by millibar vapor deposition.

[0334] e. EML (Emitting Layer, 40nm): Deposited on the second hole transport layer by vacuum evaporation (1×10⁻⁶ nm). -6 The light-emitting layer materials RD and RH were deposited by vapor deposition in millibar (mbar) manner, with a mass ratio of RD to RH of 97:3.

[0335] f. ETL (Electron Transport Layer, 30nm): deposited on the light-emitting layer via vacuum evaporation (1×10⁻⁶ nm). -6 Electron transport layer materials ET and LiQ were deposited by millibar evaporation; ET and LiQ were placed in different evaporation units, and the mass ratio of ET to LiQ was 5:5.

[0336] g. EIL (Electron Injection Layer, 1nm): deposited on the electron transport layer via vacuum evaporation (1×10⁻⁶ nm). -6 LiQ electron injection layer material is deposited by evaporation using a millibar method;

[0337] h. Cathode (100nm): Deposited on the electron injection layer by vacuum evaporation (1×10⁻⁶ nm). -6 Al cathode material is deposited by evaporation using the millibar method;

[0338] i. The OLED-1 device is obtained by encapsulating the device with ultraviolet-cured resin in a nitrogen glove box.

[0339] The chemical structural formulas of HATCN, HT-1, RD, RH, ET, and LiQ are as follows:

[0340]

[0341] The implementation schemes of OLED-2, OLED-20, OLED-Ref-1 and OLED-Ref-2 are the same except that the material of the second hole transport layer is replaced with the organic compounds of Examples 2-20 and Comparative Examples 1-2 shown in Table 2.

[0342] The current-voltage (JV) characteristics of each OLED device were characterized using characterization equipment, and the lifetime (LT95@8000 nits) and external quantum efficiency were recorded. The lifetime LT95 was measured at a constant current of 10 mA / cm². 2 The time it takes for the brightness to drop to 95% of the initial brightness at 8000 nits is calculated. The LT95 and external quantum efficiency in this application are calculated relative to the OLED-Ref-1 device of Comparative Example 1, where the lifetime of Comparative Example 1 is 1 and the external quantum efficiency is 100%. The OLED-Ref-1 device of Comparative Example 1 has a voltage of 3.8V, an efficiency of 18cd / A, and a lifetime of 45 hours at 8000 nits. The results are shown in Table 2 below.

[0343] Table 2:

[0344]

[0345]

[0346] As shown in Table 2:

[0347] The external quantum efficiency and lifetime of the OLED devices in Examples 1-20 are significantly higher than those in Comparative Examples 1-2. This may be because the dibenzofuranoindole group significantly alters the spatial structure of the organic compound molecules compared to the comparative organic compounds, thereby improving molecular packing, increasing molecular rigidity, and raising the glass transition temperature, thus enhancing the efficiency, stability, and lifetime of the OLED devices.

[0348] The organic compound of this application has an aromatic amine group introduced at the 2-position of the benzofuranocarbazoyl group and an R group introduced at the ortho-position of the aromatic amine group. 1 and / or R 2 This effectively improves molecular packing, giving the material molecules greater rigidity and thus increasing the glass transition temperature of the material molecules. Organic electronic devices prepared using the organic compounds of this application as hole transport materials exhibit long lifetimes and high luminous efficiency.

[0349] The organic compounds, mixtures, compositions, and organic electronic devices provided in the embodiments of this application have been described in detail above. 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 organic compound, characterized by, having the structure of formula (1): ； wherein: R 1 is selected from methyl, -CD3, ethyl, -CD2-CD3, isopropyl, tert-butyl, phenyl, or phenyl substituted with one or more methyl groups; R 2 is selected from -H, methyl, ethyl, -CD2-CD3, isopropyl, or phenyl; in general formula (1) is selected from one of the following structures: ； Ar 3 is selected from phenyl, naphthyl or biphenyl.

2. An organic compound, characterized by, the organic compound is selected from one of the following structures: 。 3. A mixture characterized in that: the mixture comprises the organic compound according to any one of claims 1-2 and at least one organic functional material 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, an organic luminescent guest material, or an organic host material.

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

5. An organic electronic device comprising at least one functional layer, characterized in that: the functional layer comprises the organic compound according to any one of claims 1-2, or the mixture according to claim 3, or the functional layer is prepared from the composition according to claim 4.

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