Organic compounds, mixtures, compositions and organic electronic devices

Abstract

The present application provides an organic compound, a mixture, a composition and an organic electronic device. The structure of the organic compound is shown in the general formula (1): #imgabs0# wherein: n1, n2, and n3 are integers from 1 to 3; each occurrence of R1, R2, and R3 is independently selected from H, D, a straight-chain alkyl group, a straight-chain alkoxy group, a straight-chain thioalkoxy group, a branched or cyclic alkyl group, a branched or cyclic alkoxy group, a branched or cyclic thioalkoxy group, a silyl group, a keto group, an alkoxycarbonyl group, an aryloxycarbonyl group, a substituted or unsubstituted aromatic group or heteroaromatic group, an aryloxy or heteroaryloxy group, a cyano group, a carbamoyl group, a halocarbonyl group, a formyl group, an isocyano group, an isocyanate group, a thiocyanate group, an isothiocyanate group, a hydroxyl group, a nitro group, an amino group, CF3, Cl, Br, F, I, or a combination of these groups. The organic compound provided by the present application can increase the luminous efficiency and service life of the organic electronic device.

Description

Technical Field

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

[0002] Organic semiconductor materials have diversity in synthesis, relatively low manufacturing costs and excellent optical and electrical properties. Organic light-emitting diodes (OLEDs) have advantages in the application of optoelectronic devices (such as flat panel displays and lighting) such as wide viewing angle, fast response time, low operating voltage, and thin panel thickness, and therefore have broad development potential. In order to improve the luminous efficiency of organic light-emitting diodes, various fluorescent and phosphorescent luminescent material systems have been developed. Among them, organic light-emitting diodes using fluorescent materials have the characteristics of high reliability, but their internal electroluminescence quantum efficiency is limited to 25% under electrical excitation, because the branching ratio of the singlet excited state and the triplet excited state of the exciton is 1:3. Organic light-emitting diodes using phosphorescent materials have achieved almost 100% internal electroluminescence quantum efficiency, but phosphorescent OLEDs have a major difficulty: Roll-off effect, that is, the luminous efficiency decreases rapidly with the increase of current or brightness, which is particularly unfavorable for high-brightness applications.

[0003] So far, the traditional phosphorescent materials with practical use value are complexes containing iridium and platinum. However, this raw material is rare and expensive, and the synthesis of the complex is complicated, so the cost is also quite high. In order to overcome the above problems, Adachi proposed the concept of reverse internal conversion, which can use organic compounds, that is, not use metal complexes, and achieve high efficiency comparable to phosphorescent OLEDs. This concept has been realized through various material combinations, such as: 1) using composite excited state materials; 2) using thermally excited delayed fluorescence (TADF) materials.

[0004] Most traditional organic compounds with TADF use the method of connecting electron donor (Donor) and electron acceptor (Acceptor) groups, which causes the electron cloud distribution of the highest occupied orbital (HOMO) and the lowest unoccupied orbital (LUMO) to be completely separated, narrowing the difference (△EST) between the singlet state (S1) and triplet state (T1) of organic compounds. The performance of traditional blue light TADF materials is still somewhat behind that of phosphorescent materials in terms of efficiency and lifespan. Summary of the invention

[0005] In view of this, the present application provides an organic compound, a mixture, a composition and an organic electronic device capable of increasing the luminous efficiency and service life of an organic electronic device.

[0006] To solve the above problems, the technical solutions provided by this application are as follows:

[0007] The first aspect of the present application provides an organic compound, wherein the organic compound is a boron-containing indole diphenylamine organic compound, and the structure of the organic compound is shown in general formula (1):

[0008]

[0009] in:

[0010] n1, n2, n3 are integers from 1 to 3; R1, R2, R3, each time occurring, are independently selected from H, D, straight-chain alkyl, straight-chain alkoxy, straight-chain thioalkoxy, branched or cyclic alkyl, branched or cyclic alkoxy, branched or cyclic thioalkoxy, silyl, keto, alkoxycarbonyl, aryloxycarbonyl, substituted or unsubstituted aromatic or heteroaromatic groups, aryloxy or heteroaryloxy, cyano, carbamoyl, haloformyl, formyl, isocyano, isocyanate, thiocyanate, isothiocyanate, hydroxyl, nitro, amine, CF3, Cl, Br, F, I or a combination of these groups.

[0011] The second aspect of the present application also provides a mixture, comprising the organic compound as described above and at least one organic functional material, wherein the organic functional material is selected from at least one of hole injection materials, hole transport materials, electron transport materials, electron injection materials, electron blocking materials, hole blocking materials, luminescent bodies, luminescent host materials and organic dyes.

[0012] The third aspect of the present application also provides a composition, comprising the organic compound as described above or the mixture as described above and at least one organic solvent.

[0013] A fourth aspect of the present application further provides an organic electronic device, comprising the organic compound as described above or the mixture as described above.

[0014] The organic compound provided in the present application is a boron-containing indole diphenylamine organic compound. By fusing a benzene ring and a five-membered ring (an azo five-membered ring in the boron-containing indole diphenylamine organic compound), the overall molecular structure has better conjugation and planarity, and combined with the selection of each substituent, a boron-containing fused ring compound is formed, which is convenient for improving the rigidity and stability of the material molecule, thereby achieving the purpose of extending the luminous efficiency and service life of the device. In addition, the boron-containing indole diphenylamine organic compound (the organic compound) described in the present application can be used as a blue light guest material, and by matching with a suitable host material, the luminous efficiency and service life of the electroluminescent device can be improved. BRIEF DESCRIPTION OF THE DRAWINGS

[0015] In order to more clearly illustrate the technical solutions in the embodiments of the present application, the drawings required for use in the description of the embodiments will be briefly introduced below. Obviously, the drawings described below are only some embodiments of the present application. For those skilled in the art, other drawings can be obtained based on these drawings without creative work.

[0016] Figure 1 A cross-sectional view of an organic electronic device provided in a preferred embodiment of the present application. DETAILED DESCRIPTION

[0017] For ease of understanding of the present application, the present application will be described more fully below with reference to relevant embodiments. The preferred embodiments of the present application are provided in the embodiments. However, the present application can be implemented in many different forms and is not limited to the embodiments described herein. On the contrary, the purpose of providing these embodiments is to make the understanding of the disclosure of the present application more thorough and comprehensive.

[0018] Unless otherwise defined, all technical and scientific terms used herein have the same meaning as those generally understood by those skilled in the art to which this application belongs. The terms used herein in the specification of this application are only for the purpose of describing specific embodiments and are not intended to limit this application. The term "and / or" used herein includes any and all combinations of one or more related listed items.

[0019] In the present application, a five-membered ring refers to a ring formed by five atoms through chemical bonding. "Substituted or unsubstituted" means that the defined group may be substituted or not. When the defined group is substituted, it should be understood that the defined group may be substituted by one or more substituents R, wherein R is selected from but not limited to: a deuterium atom, a cyano group, an isocyano group, a nitro group or a halogen, a C1-30 alkyl group, a heterocyclic group containing 3-20 ring atoms, an aromatic group containing 6-20 ring atoms, a heteroaromatic group containing 5-20 ring atoms, -NR'R", a silane group, a carbonyl group, an alkoxycarbonyl group, an aryloxycarbonyl group, a carbamoyl group, a haloformyl group, formyl, isocyanate, thiocyanate, isothiocyanate, hydroxyl, trifluoromethyl, and the above groups may be further substituted by substituents acceptable in the art; it is understandable that R' and R" in -NR'R" are independently selected from but not limited to: H, deuterium atom, cyano, isocyano, nitro or halogen, C1-10 alkyl, heterocyclic group containing 3-20 ring atoms, aromatic group containing 6-20 ring atoms, heteroaromatic group containing 5-20 ring atoms.

[0020] In the present application, the "number of ring atoms" refers to the number of atoms in the atoms constituting the ring itself of a structural compound (e.g., a monocyclic compound, a condensed ring compound, a cross-linked compound, a carbocyclic compound, a heterocyclic compound) formed by atoms bonding to form a ring. When the ring is substituted by a substituent, the atoms contained in the substituent are not included in the ring atoms. The same is true for the "number of ring atoms" described below unless otherwise specified. For example, the number of ring atoms of a benzene ring is 6, the number of ring atoms of a naphthalene ring is 10, and the number of ring atoms of a thienyl group is 5.

[0021] "Aryl, aromatic group or aromatic group" may be a monocyclic or polycyclic aromatic group. A condensed ring aromatic group means that the ring of an aromatic group may have two or more rings, wherein two carbon atoms are shared by two adjacent rings, i.e., a condensed ring. The aromatic group is selected from, but not limited to, phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthrenyl, fluoranthenyl, triphenylene, pyrenyl, perylene, naphthylene, fluorenyl, perylene, acenaphthene and derivatives thereof.

[0022] A heteroaromatic group refers to a heteroaromatic hydrocarbon group containing at least one heteroatom. The heteroatom is preferably selected from Si, N, P, O, S and / or Ge, particularly preferably selected from Si, N, P, O and / or S. A fused heterocyclic aromatic group refers to a fused heterocyclic aromatic hydrocarbon group containing at least one heteroatom. For the purposes of this application, aromatic groups or heteroaromatic groups include not only systems of aromatic rings, but also non-aromatic ring systems. Thus, for example, systems such as pyridine, thiophene, pyrrole, pyrazole, triazole, imidazole, oxazole, oxadiazole, thiazole, tetrazole, pyrazine, pyridazine, pyrimidine, triazine, carbene, etc. are also considered to be aromatic groups or heterocyclic aromatic groups for the purposes of this invention. For the purposes of this application, fused aromatic or fused heterocyclic aromatic ring systems include not only systems of aromatic groups or heteroaromatic groups, but also, wherein a plurality of aromatic groups or heterocyclic aromatic groups may also be interrupted by short non-aromatic units (<10% of non-H atoms, preferably less than 5% of non-H atoms, such as C, N or O atoms). Thus, systems such as 9,9'-spirobifluorene, 9,9-diarylfluorene, triarylamines, diaryl ethers, etc. are also considered to be fused aromatic ring systems for the purposes of this invention.

[0023] Examples of the heteroaromatic group include, but are not limited to, thienyl, furanyl, pyrrolyl, imidazolyl, triazolyl, imidazolyl, oxadiazolyl, triazolyl, pyridyl, bipyridyl, pyrimidyl, triazinyl, triazolyl, acridinyl, pyridazinyl, pyrazinyl, quinolyl, quinazolinyl, quinoxalinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, isoquinolyl, indolyl, carbazolyl, benzothiophenyl, benzo Furanyl, indolyl, carbazolyl, pyrroloimidazolyl, pyrrolopyrrolyl, thienopyrrolyl, thienothiphenyl, furopyrrolyl, furofuranyl, thienofuranyl, benzisoxazolyl, benzisothiazolyl, benzimidazolyl, quinolyl, isoquinolyl, o-naphthyl, quinoxalinyl, phenanthridinyl, primary pyridyl, quinazolinyl, quinazolinone, dibenzothiophenyl, dibenzofuranyl, carbazolyl and derivatives thereof.

[0024] In the present application, "alkyl" may mean a straight chain, branched chain and / or cyclic alkyl. The carbon number of the alkyl group may be 1 to 50, 1 to 30, 1 to 20, 1 to 10 or 1 to 6. A phrase containing this term, for example, "C1-9 alkyl" means an alkyl group containing 1 to 9 carbon atoms, and each occurrence may be independently 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 decyl, 2-ethyldodecyl, 2-butyldodecyl, 2-hexyldodecyl, 2-octyldodecyl, n-undecyl, n-dodecyl, 2-ethyldodecyl, 2-butyldodecyl, 2-hexyldodecyl, 2-octyldodecyl, n-tridecyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, 2-ethylhexadecyl, 2-butylhexadecyl, 2-hexylhexadecyl, 2-octylhexadecyl, n-heptadecyl, n-octadecyl, n-nonadecyl, n-eicosyl, 2-ethyleicosyl, 2-butyleicosyl, 2-hexyleicosyl, 2-octyleicosyl, n-heneicosyl, n-docosyl, n-tricosyl, n-tetracosyl, n-pentacosyl, n-hexacosyl, n-heptacosyl, n-octacosyl, n-nonacosyl, n-triacontyl, adamantane, and the like.

[0025] In the present application, the substituent abbreviations correspond to: n-normal, sec-secondary, i-iso, t-tertiary, o-ortho, m-meta, p-para, Me methyl, Et ethyl, Pr propyl, Bu butyl, Am n-pentyl, Hx hexyl, Cy cyclohexyl.

[0026] "Amine" refers to an amine derivative having the structural features of the formula -N(X)2, wherein each "X" is independently H, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted heterocyclyl, etc. Non-limiting types of amines include -NH2, -N(alkyl), -NH(alkyl), -N(cycloalkyl), -NH(cycloalkyl), -N(heterocyclyl), -NH(heterocyclyl), -N(aryl), -NH(aryl), -N(alkyl)(aryl), -N(alkyl)(heterocyclyl), -N(cycloalkyl)(heterocyclyl), -N(aryl)(heteroaryl), -N(alkyl)(heteroaryl), -N(heteroaryl), etc.

[0027] In the present application, "*" connected to a single bond indicates a connection or fusion site.

[0028] In the present application, when a linking site is not specified in a group, it means that an optional linking site in the group can be used as a linking site.

[0029] In the present application, when the fusion site is not specified in the group, it means that any fusion site in the group can be used as the fusion site, and preferably two or more sites in the ortho position in the group are fusion sites.

[0030] In the present application, the single bond to which the substituent is connected runs through the corresponding ring, indicating that the substituent can be connected to any position of the ring, for example In which R is connected to any substitutable position of the benzene ring, such as express Can be used with The above optional substitutable positions form a ring.

[0031] In the embodiments of the present application, the energy level structure of organic materials, triplet energy levels ET, HOMO, and LUMO play a key role. These energy levels are introduced below:

[0032] HOMO and LUMO energy levels can be measured by photoelectric effects, such as XPS (X-ray photoelectron spectroscopy) and UPS (ultraviolet photoelectron spectroscopy) or by cyclic voltammetry (hereafter referred to as CV). Recently, quantum chemical methods, such as density functional theory (hereafter referred to as DFT), have also become effective methods for calculating molecular orbital energy levels.

[0033] The triplet energy level ET1 of the organic material can be measured by low-temperature time-resolved luminescence spectroscopy, or obtained by quantum simulation calculation (such as by Time-dependent DFT), such as by the commercial software Gaussian 03W (Gaussian Inc.). The specific simulation method can be found in WO2011141110 or described in the following embodiments.

[0034] It should be noted that the absolute values ​​of HOMO, LUMO, and ET1 depend on the measurement method or calculation method used, and even for the same method, different evaluation methods, such as the starting point and the peak point on the CV curve, can give different HOMO / LUMO values. Therefore, a reasonable and meaningful comparison should be made using the same measurement method and the same evaluation method. In the description of the embodiments of the present application, the values ​​of HOMO, LUMO, and ET1 are based on the simulation of Time-dependent DFT, but do not affect the application of other measurement or calculation methods.

[0035] In the present invention, (HOMO-1) is defined as the second highest occupied orbital energy level, (HOMO-2) is the third highest occupied orbital energy level, and so on. (LUMO+1) is defined as the second lowest unoccupied orbital energy level, (LUMO+2) is the third lowest occupied orbital energy level, and so on.

[0036] The present application provides an organic compound, which is a boron-containing indole diphenylamine organic compound, and the structure of the organic compound is shown in general formula (1):

[0037]

[0038] in:

[0039] n1, n2, n3 are integers of 1-3; R1, R2, R3, each time appearing, are independently selected from H, D, straight-chain alkyl, straight-chain alkoxy, straight-chain thioalkoxy, branched or cyclic alkyl, branched or cyclic alkoxy, branched or cyclic thioalkoxy, silyl, keto, alkoxycarbonyl, aryloxycarbonyl, substituted or unsubstituted aromatic or heteroaromatic groups, aryloxy or heteroaryloxy, cyano, carbamoyl, haloformyl, formyl, isocyano, isocyanate, thiocyanate, isothiocyanate, hydroxyl, nitro, amine, CF3, Cl, Br, F, I or a combination of these groups, and adjacent R1, R2, R3 form a ring with each other.

[0040] In an optional embodiment of the present application, R1, R2, and R3 are independently selected from any one of the following groups:

[0041]

[0042] Wherein: * represents the attachment site. Each occurrence of R4 is independently selected from H, D, straight chain alkyl, straight chain alkoxy, straight chain thioalkoxy, branched or cyclic alkyl, branched or cyclic alkoxy, branched or cyclic thioalkoxy, silyl, keto, alkoxycarbonyl, aryloxycarbonyl, substituted or unsubstituted aromatic or heteroaromatic groups, aryloxy or heteroaryloxy, cyano, carbamoyl, haloformyl, formyl, isocyano, isocyanate, thiocyanate, isothiocyanate, hydroxyl, nitro, amine, CF3, Cl, Br, F, I or a combination of these groups, adjacent R1 can form a ring, adjacent R2 can form a ring, and adjacent R3 can form a ring.

[0043] In an optional embodiment of the present application, R1, R2, and R3 are independently selected from any one of the following groups, selected from the following structures:

[0044]

[0045] In an optional embodiment of the present application, R1, R2, and R3 are independently selected from any one of the following groups:

[0046]

[0047] In an optional embodiment of the present application, R1, R2, and R3 are independently selected from -H, -D, methyl, ethyl, n-propyl, isopropyl, tAm, tBu, and the following groups:

[0048]

[0049] Specifically, the structure of the organic compound is selected from any of the following structures:

[0050]

[0051]

[0052]

[0053]

[0054]

[0055]

[0056]

[0057] The organic compound can be used as a functional material in organic electronic devices, especially organic light emitting diodes (OLED) devices.

[0058] Therefore, the present application also provides a mixture, which includes the organic compound and at least one organic functional material, and the organic functional material is selected from at least one of a hole injection material (HIM), a hole transport material (HTM), an electron transport material (ETM), an electron injection material (EIM), an electron blocking material (EBM), a hole blocking material (HBM), an emitter, a host material (Host) and an organic dye.

[0059] Wherein, the luminophore is selected from at least one of a singlet luminophore, a triplet luminophore and an organic thermally excited delayed fluorescent material. For example, various organic functional materials are described in detail in WO2010135519A1, US20090134784A1 and WO 2011110277A1, and the entire contents of these three patent documents are incorporated herein by reference. The organic functional material can be a small molecule and a polymer material.

[0060] The host material mainly refers to the host material in the light-emitting layer.

[0061] Wherein, when the organic functional material is the luminophore, the luminophore is the guest material of the luminescent layer, and the organic compound is the host material of the luminescent layer. When the organic functional material is the host material, the host material is the host material of the luminescent layer, and the organic compound is the guest material of the luminescent layer. Preferably, the host material is a blue light host material.

[0062] Therefore, the present application also provides a composition, comprising the organic compound or the mixture and at least one organic solvent.

[0063] Herein, the composition may also be referred to as ink.

[0064] When used in the printing process, the viscosity and surface tension of the ink are important parameters. The surface tension parameters of the appropriate ink are suitable for a specific substrate and a specific printing method. In a preferred embodiment, the surface tension of the ink according to the present application at the working temperature or at 25°C is approximately in the range of 19dyne / cm to 50dyne / cm; more preferably in the range of 22dyne / cm to 35dyne / cm; most preferably in the range of 25dyne / cm to 33dyne / cm. The viscosity of the ink according to the present application at the working temperature or at 25°C is approximately in the range of 1cps to 100cps; preferably in the range of 1cps to 50cps; more preferably in the range of 1.5cps to 20cps; most preferably in the range of 4.0cps to 20cps. The composition formulated in this way will facilitate inkjet printing.

[0065] The viscosity can be adjusted by different methods, such as by selecting a suitable solvent and the concentration of the functional material in the ink. The ink containing the metal organic complex or polymer according to the present application can facilitate people to adjust the printing ink in an appropriate range according to the printing method used. Generally, the weight ratio of the functional material contained in the composition according to the present application is in the range of 0.3% to 30wt%, preferably in the range of 0.5% to 20wt%, more preferably in the range of 0.5% to 15wt%, more preferably in the range of 0.5% to 10wt%, and most preferably in the range of 1% to 5wt%. The composition prepared in this way will facilitate inkjet printing.

[0066] In some embodiments, the organic solvent is selected from aromatic or heteroaromatic compounds, esters, aromatic ketones or aromatic ethers, aliphatic ketones or aliphatic ethers, alicyclic or olefinic compounds, or borate or phosphate compounds, or a mixture of two or more solvents.

[0067] In a preferred embodiment, the organic solvent is selected from aromatic or heteroaromatic based solvents.

[0068] Examples of aromatic or heteroaromatic solvents suitable for the present application include, but are not limited to: p-diisopropylbenzene, pentylbenzene, tetralin, cyclohexylbenzene, chloronaphthalene, 1,4-dimethylnaphthalene, 3-isopropylbiphenyl, p-methylisopropylbenzene, dipentylbenzene, tripentylbenzene, pentyltoluene, o-diethylbenzene, m-diethylbenzene, p-diethylbenzene, 1,2,3,4-tetramethylbenzene, 1,2,3,5-tetramethylbenzene, 1,2,4,5-tetramethylbenzene, butylbenzene, dodecylbenzene, dihexylbenzene, dibutylbenzene, p-diisopropylbenzene, cyclohexylbenzene, benzylbutylbenzene, dimethylnaphthalene, 3-isopropylbiphenyl, p-methylisopropylbenzene, 1-methylnaphthalene, 1,2,4-trichlorobenzene, 4,4-difluorodiphenylmethane, 1,2-dimethoxy-4-(1-propenyl)benzene, diphenylmethane, 2-phenylpyridine, 3-phenylpyridine, N-methyldiphenylamine, 4-isopropylbiphenyl, α,α-dichlorodiphenylmethane, 4-(3-phenylpropyl)pyridine, benzyl benzoate, 1,1-bis(3,4-dimethylphenyl)ethane, 2-isopropylnaphthalene, quinoline, isoquinoline, methyl 2-furoate, ethyl 2-furoate, etc.

[0069] Examples of aromatic ketone-based solvents suitable for the present application include, but are not limited to: 1-tetralone, 2-tetralone, 2-(phenylepoxy)tetralone, 6-(methoxy)tetralone, acetophenone, propiophenone, benzophenone, and their derivatives, such as 4-methylacetophenone, 3-methylacetophenone, 2-methylacetophenone, 4-methylpropiophenone, 3-methylpropiophenone, 2-methylpropiophenone, and the like.

[0070] Examples of aromatic ether-based solvents suitable for the present application include, but are not limited to, 3-phenoxytoluene, butoxybenzene, p-anisaldehyde dimethyl acetal, tetrahydro-2-phenoxy-2H-pyran, 1,2-dimethoxy-4-(1-propenyl)benzene, 1,4-benzodioxane, 1,3-dipropylbenzene, 2,5-dimethoxytoluene, 4-ethyl ethyl ether, 1,3-dipropoxybenzene, 1,2,4-trimethoxybenzene, 4-(1-propenyl)-1,2-dimethoxybenzene, 1,3-dimethoxybenzene, glycidyl phenyl ether, dibenzyl ether, 4-tert-butylanisole, trans-p-propenylanisole, 1,2-dimethoxybenzene, 1-methoxynaphthalene, diphenyl ether, 2-phenoxymethyl ether, 2-phenoxytetrahydrofuran, and ethyl-2-naphthyl ether.

[0071] In some preferred embodiments, the organic solvent is selected from: aliphatic ketones, for example, 2-nonanone, 3-nonanone, 5-nonanone, 2-decanone, 2,5-hexanedione, 2,6,8-trimethyl-4-nonanone, fenchone, phorone, isophorone, di-n-amyl ketone, etc.; or aliphatic ethers, for example, amyl ether, hexyl ether, dioctyl ether, ethylene glycol dibutyl ether, diethylene glycol diethyl ether, diethylene glycol butyl methyl ether, diethylene glycol dibutyl ether, triethylene glycol dimethyl ether, triethylene glycol ethyl methyl ether, triethylene glycol butyl methyl ether, tripropylene glycol dimethyl ether, tetraethylene glycol dimethyl ether, etc.

[0072] In other preferred embodiments, according to the composition of the present application, at least one organic solvent is selected from ester-based solvents: alkyl octanoate, alkyl sebacate, alkyl stearate, alkyl benzoate, alkyl phenylacetate, alkyl cinnamate, alkyl oxalate, alkyl maleate, alkyl lactone, alkyl oleate, etc. Octyl octanoate, diethyl sebacate, diallyl phthalate, isononyl isononanoate, etc. are particularly preferred.

[0073] The organic solvent may be used alone or as a mixture of two or more organic solvents.

[0074] In a preferred embodiment, the organic solvent includes but is not limited to: methanol, ethanol, 2-methoxyethanol, dichloromethane, chloroform, chlorobenzene, o-dichlorobenzene, tetrahydrofuran, anisole, morpholine, toluene, o-xylene, m-xylene, p-xylene, 1,4-dioxane, acetone, methyl ethyl ketone, 1,2-dichloroethane, 3-phenoxytoluene, 1,1,1-trichloroethane, 1,1,2,2-tetrachloroethane, ethyl acetate, butyl acetate, dimethylformamide, dimethylacetamide, dimethyl sulfoxide, tetralin, decalin, indene and / or mixtures thereof.

[0075] The present application also relates to the use of the composition as a coating or printing ink in the preparation of an organic electronic device, and a preparation method by printing or coating is particularly preferred.

[0076] Among them, suitable printing or coating techniques include (but are not limited to) inkjet printing, nozzle printing, letterpress printing, screen printing, dip coating, spin coating, doctor blade coating, roller printing, twist roller printing, lithography, flexographic printing, rotary printing, spraying, brushing or pad printing, slit extrusion coating, etc. The preferred ones are gravure printing, nozzle printing and inkjet printing. The solution or suspension may further include one or more components such as surfactant compounds, lubricants, wetting agents, dispersants, hydrophobic agents, adhesives, etc., for adjusting viscosity, film-forming properties, improving adhesion, etc. Relevant printing technology and its related requirements for relevant solutions, such as solvents and concentrations, viscosity, etc.

[0077] The present application also provides an application of the above-mentioned organic compound, mixture or composition in an organic electronic device. Specifically, the fourth aspect of the present application also provides an organic electronic device, including the organic compound as described above or the mixture as described above. The organic electronic device can be selected from but not limited to: organic light-emitting diodes (OLED), organic photovoltaic cells (OPV), organic light-emitting electrochemical cells (OLEEC), organic field-effect transistors (OFET), organic light-emitting field-effect transistors, organic lasers, organic spin electronic devices, organic sensors and organic plasmon emitting diodes (OPED), etc. Preferred are organic electroluminescent devices, such as OLED, OLEEC and organic light-emitting field-effect transistors. Particularly preferably, the organic electroluminescent device is an OLED. In an embodiment of the present invention, the organic compound is preferably used in the light-emitting layer of an OLED device.

[0078] Specifically, see Figure 1 The organic electronic device 100 includes a light-emitting layer 105, and the light-emitting layer 105 includes the organic compound as described above.

[0079] In an optional embodiment of the present application, the organic compound in the light-emitting layer 105 is a blue light material.

[0080] In an optional embodiment of the present application, the light-emitting layer 105 further includes a host material, and the organic compound in the light-emitting layer 105 is a guest material, and the guest material cooperates with the host material to emit light. Preferably, the host material is a blue light host material. The blue light host material refers to a host material that can emit blue light.

[0081] In an optional embodiment of the present application, the light-emitting layer 105 further includes a luminophore, the organic compound in the light-emitting layer 105 is a host material, the luminophore is a guest material of the light-emitting layer, and the luminophore cooperates with the organic compound to emit light.

[0082] In an optional embodiment of the present application, the organic electronic device 100 further includes a substrate 101, an anode 102, an organic functional layer and a cathode 107, wherein the organic functional layer is located between the anode 102 and the cathode 107, the anode 102 is formed on the substrate 101, and the light-emitting layer 105 is formed between the anode 102 and the cathode 107. In an embodiment of the present application, the light-emitting layer 105 is not included in the organic functional layer, and in another embodiment of the present application, the light-emitting layer 105 may also be included in the organic functional layer.

[0083] The organic functional layer includes a hole injection layer 103, a hole transport layer 104, an electron transport layer 106, an electron injection layer (not shown), an electron blocking layer (not shown) and a hole blocking layer (not shown), etc., wherein the electron blocking layer (not shown) and the hole blocking layer (not shown) can be omitted according to actual needs. Specifically, the anode 102, the hole injection layer 103, the hole transport layer 104, the electron blocking layer, the light-emitting layer 105, the hole blocking layer, the electron transport layer 106, the electron injection layer and the cathode are stacked in sequence.

[0084] Among them, the organic compound can also be doped in at least one of the hole injection layer 103, the hole transport layer 104, the electron transport layer 106, the electron injection layer (not shown), the electron blocking layer (not shown) and the hole blocking layer (not shown) of the organic functional layer. Accordingly, the organic compound is doped in at least one of the hole injection material, the hole transport material, the electron transport material, the electron injection material, the electron blocking material and the hole blocking material.

[0085] Wherein, substrate 101 can be opaque or transparent. A transparent substrate can be used to make a transparent light-emitting device. For example, see Bulovic et al. Nature 1996, 380, p29, and Gu et al., Appl. Phys. Lett. 1996, 68, p2606. The substrate can be rigid or elastic. The substrate can be plastic, metal, semiconductor wafer or glass. It is best that the substrate has a smooth surface. Substrates without surface defects are particularly ideal. In a preferred example, the substrate is flexible and can be selected from polymer films or plastics, and its glass transition temperature Tg is above 150°C, preferably above 200°C, more preferably above 250°C, and preferably above 300°C. Examples of suitable flexible substrates include polyethylene terephthalate (PET) and polyethylene glycol (2,6-naphthalene) (PEN).

[0086] The anode may include a conductive metal or metal oxide, or a conductive polymer. The anode can easily inject holes into a hole injection layer (HIL) or a hole transport layer (HTL) or a light-emitting layer. In one example, the absolute value of the difference between the work function of the anode and the HOMO energy level or valence band energy level of the light-emitting body in the light-emitting layer or the p-type semiconductor material as the HIL or HTL or the electron blocking layer (EBL) is less than 0.5 eV, preferably less than 0.3 eV, and most preferably less than 0.2 eV. Examples of anode materials include, but are not limited to, Al, Cu, Au, Ag, Mg, Fe, Co, Ni, Mn, Pd, Pt, ITO, aluminum-doped zinc oxide (AZO), etc. Other suitable anode materials are known and can be easily selected for use by a person of ordinary skill 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 prepare devices according to the present invention.

[0087] The cathode may include a conductive metal or metal oxide. The cathode can easily inject electrons into the EIL or ETL or directly into the light-emitting layer. In one embodiment, the absolute value of the difference between the work function of the cathode and the LUMO energy level or conduction band energy level of the luminophore in the light-emitting layer or the n-type semiconductor material as the electron injection layer (EIL) or the electron transport layer (ETL) or the hole blocking layer (HBL) is less than 0.5 eV, preferably less than 0.3 eV, and most preferably less than 0.2 eV. In principle, all materials that can be used as cathodes of OLEDs may be used as cathode materials for the device 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.

[0088] Other organic functional layers of OLED, such as hole injection layer (HIL), hole transport layer (HTL), electron blocking layer (EBL), electron injection layer (EIL), electron transport layer (ETL), hole blocking layer (HBL), etc. Materials suitable for use in these organic functional layers are described in detail above and in WO2010135519A1, US20090134784A1 and WO2011110277A1, and the entire contents of these three patent documents are hereby incorporated herein by reference.

[0089] In a preferred example, the light-emitting layer of the organic electronic device is prepared from the composition as described above.

[0090] The wavelength of light emitted by the organic electronic device is between 300nm and 1000nm, preferably between 350nm and 900nm, and more preferably between 400nm and 800nm.

[0091] The organic electronic device of the present application can be applied in various electronic devices, including but not limited to display devices, lighting devices, light sources, sensors, etc.

[0092] The boron-containing indole diphenylamine organic compound of the present invention is further described in detail below in conjunction with specific examples. The raw materials used in the following examples, unless otherwise specified, are all commercially available products. Specific embodiments

[0094] This embodiment provides a boron-containing indole diphenylamine organic compound, and the specific synthesis route is as follows:

[0095] Example 1

[0096]

[0097] Synthesis of intermediate 1-3:

[0098] Compound 1-1 (10 mmol), compound 1-2 (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 nitrogen atmosphere. After cooling, the solvent was removed by rotary evaporation, and the mixture was extracted and washed with water. The organic phase was subjected to column chromatography to obtain intermediate 1-3 with a molar weight of 7.64 mmol, a yield of 76.4%, and MS (ASAP) = 284.6.

[0099] Synthesis of intermediate 1-5:

[0100] Compound 1-3 (20 mmol), compound 1-4 (10 mmol), Pd-132 (0.1 mmol), SPhos (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, and the mixture was extracted and washed with water. The organic phase was subjected to column chromatography to obtain intermediate 1-5 with a molar weight of 6.22 mmol, a yield of 62.2%, and MS (ASAP) = 676.5.

[0101] Synthesis of compound (1): 10 mmol of intermediate 1-5 and 100 ml of dry tert-butylbenzene were added to a 250 ml three-necked flask, cooled to -30 degrees Celsius in a N2 atmosphere, and (21 mmol) of t-BuLi n-hexane solution was added dropwise. The temperature was raised to 60 degrees Celsius for reaction for 2 hours, and the n-hexane solvent was evaporated under reduced pressure. The reaction solution was cooled to -30 degrees Celsius again, 21 mmol of boron tribromide solution was added, and the mixture was heated to room temperature and stirred for 0.5 hours. The reaction solution was then cooled to 0 degrees Celsius, and 42 mmol of N,N-diisopropylethylamine was added. After the addition was complete, the mixture was heated to room temperature and stirred, and then the temperature was continued to be raised to 120 degrees Celsius and stirred for 3 hours. The reaction solution was cooled to room temperature. Sodium carbonate aqueous solution and ethyl acetate were added to quench the reaction. The aqueous phase was extracted with ethyl acetate and the organic phase was combined, and the solvent was evaporated to obtain a crude product, which was purified by rapid silica gel column to obtain a pure product. Recrystallization was performed with toluene and ethyl acetate to obtain a light yellow solid powder. The yield was 73.3%, MS (ASAP) = 650.4.

[0102] Example 2

[0103]

[0104] Synthesis of intermediate 2-2:

[0105] Compound 2-1 (10 mmol), compound 1-2 (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 nitrogen atmosphere. After cooling, the solvent was removed by rotary evaporation, and the mixture was extracted and washed with water. The organic phase was subjected to column chromatography to obtain the intermediate 2-2 with a molar weight of 7.09 mmol, a yield of 70.9%, and MS (ASAP) = 298.4.

[0106] Synthesis of intermediate 2-3:

[0107] Compound 2-2 (20 mmol), compound 1-4 (10 mmol), Pd-132 (0.1 mmol), SPhos (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, and the mixture was extracted and washed with water. The organic phase was subjected to column chromatography to obtain intermediate 2-3 with a molar weight of 5.17 mmol, a yield of 51.7%, and MS (ASAP) = 704.7.

[0108] Synthesis of compound (2): 10 mmol of intermediate 2-3 and 100 ml of dry tert-butylbenzene were added to a 250 ml three-necked flask, cooled to -30 degrees Celsius in a N2 atmosphere, and (21 mmol) of t-BuLi n-hexane solution was added dropwise. The temperature was raised to 60 degrees Celsius for reaction for 2 hours, and the n-hexane solvent was evaporated under reduced pressure. The reaction solution was cooled to -30 degrees Celsius again, 21 mmol of boron tribromide solution was added, and the mixture was heated to room temperature and stirred for 0.5 hours. The reaction solution was then cooled to 0 degrees Celsius, and 42 mmol of N,N-diisopropylethylamine was added. After the addition was complete, the mixture was heated to room temperature and stirred, and then the temperature was continued to be raised to 120 degrees Celsius and stirred for 3 hours. The reaction solution was cooled to room temperature. Sodium carbonate aqueous solution and ethyl acetate were added to quench the reaction. The aqueous phase was extracted with ethyl acetate and the organic phase was combined, and the solvent was evaporated to obtain a crude product, which was purified by rapid silica gel column to obtain a pure product. Recrystallization was performed with toluene and ethyl acetate to obtain a light yellow solid powder. The yield was 61.8%, MS (ASAP) = 678.6.

[0109] Example 3

[0110]

[0111] Synthesis of intermediate 3-2:

[0112] Compound 3-1 (10 mmol), compound 1-2 (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 nitrogen atmosphere. After cooling, the solvent was removed by rotary evaporation, and the mixture was extracted and washed with water. The organic phase was subjected to column chromatography to obtain the intermediate 3-2 with a molar weight of 7.57 mmol, a yield of 75.7%, and MS (ASAP) = 312.5.

[0113] Synthesis of intermediate 3-3:

[0114] Compound 3-2 (20 mmol), compound 1-4 (10 mmol), Pd-132 (0.1 mmol), SPhos (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, and the mixture was extracted and washed with water. The organic phase was subjected to column chromatography to obtain intermediate 3-3 with a molar weight of 5.17 mmol, a yield of 51.7%, and MS (ASAP) = 732.4.

[0115] Synthesis of compound (3): 10 mmol of intermediate 3-3 and 100 ml of dry tert-butylbenzene were added to a 250 ml three-necked flask, cooled to -30 degrees Celsius in a N2 atmosphere, and (21 mmol) of t-BuLi n-hexane solution was added dropwise. The temperature was raised to 60 degrees Celsius for reaction for 2 hours, and the n-hexane solvent was removed under reduced pressure. The reaction solution was cooled to -30 degrees Celsius again, 21 mmol of boron tribromide solution was added, and the mixture was heated to room temperature and stirred for 0.5 hours. The reaction solution was then cooled to 0 degrees Celsius, and 42 mmol of N,N-diisopropylethylamine was added. After the addition was complete, the mixture was heated to room temperature and stirred, and then the temperature was continued to be raised to 120 degrees Celsius and stirred for 3 hours. The reaction solution was cooled to room temperature. Sodium carbonate aqueous solution and ethyl acetate were added to quench the reaction. The aqueous phase was extracted with ethyl acetate and the organic phase was combined, and the solvent was evaporated to obtain a crude product, which was purified by rapid silica gel column to obtain a pure product. Recrystallization was performed with toluene and ethyl acetate to obtain a light yellow solid powder. The yield was 57.7%, MS (ASAP) = 706.5.

[0116] Example 4

[0117]

[0118] Synthesis of intermediate 4-3:

[0119] Compound 4-1 (10 mmol), compound 4-2 (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 50°C for 6 h under nitrogen atmosphere. After cooling, the solvent was removed by rotary evaporation, and the mixture was extracted and washed with water. The organic phase was subjected to column chromatography to obtain intermediate 4-3 with a molar weight of 6.28 mmol, a yield of 62.8%, and MS (ASAP) = 367.1.

[0120] Synthesis of intermediate 4-4:

[0121] Compound 1-3 (20 mmol), compound 4-3 (10 mmol), Pd-132 (0.1 mmol), SPhos (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, and the mixture was extracted and washed with water. The organic phase was subjected to column chromatography to obtain intermediate 4-4 with a molar weight of 7.38 mmol, a yield of 73.8%, and MS (ASAP) = 775.5.

[0122] Synthesis of compound (4): 10 mmol of intermediate 4-4 and 100 ml of dry tert-butylbenzene were added to a 250 ml three-necked flask, cooled to -30 degrees Celsius in a N2 atmosphere, and (21 mmol) of t-BuLi n-hexane solution was added dropwise. The temperature was raised to 60 degrees Celsius for reaction for 2 hours, and the n-hexane solvent was evaporated under reduced pressure. The reaction solution was cooled to -30 degrees Celsius again, 21 mmol of boron tribromide solution was added, and the mixture was heated to room temperature and stirred for 0.5 hours. The reaction solution was then cooled to 0 degrees Celsius, and 42 mmol of N,N-diisopropylethylamine was added. After the addition was complete, the mixture was heated to room temperature and stirred, and then the temperature was continued to be raised to 120 degrees Celsius and stirred for 3 hours. The reaction solution was cooled to room temperature. Sodium carbonate aqueous solution and ethyl acetate were added to quench the reaction. The aqueous phase was extracted with ethyl acetate and the organic phase was combined, and the solvent was evaporated to obtain a crude product, which was purified by rapid silica gel column to obtain a pure product. Recrystallization was performed with toluene and ethyl acetate to obtain a light yellow solid powder. The yield was 63.1%, MS (ASAP) = 749.6.

[0123] Example 5

[0124]

[0125] Synthesis of intermediate 5-2:

[0126] Compound 4-1 (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 and stirred at 50°C for 6 h under nitrogen atmosphere. After cooling, the solvent was removed by rotary evaporation, and the mixture was extracted and washed with water. The organic phase was subjected to column chromatography to obtain the intermediate 5-2 with a molar weight of 7.25 mmol, a yield of 72.5%, and MS (ASAP) = 489.1.

[0127] Synthesis of intermediate 5-3:

[0128] Compound 1-3 (20 mmol), compound 5-2 (10 mmol), Pd-132 (0.1 mmol), SPhos (0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100°C for 6 h under nitrogen atmosphere. After cooling, the solvent was removed by rotary evaporation, and the mixture was extracted and washed with water. The organic phase was subjected to column chromatography to obtain the intermediate 5-3 with a molar weight of 4.17 mmol, a yield of 41.7%, and MS (ASAP) = 897.6.

[0129] Synthesis of compound (5): 10 mmol of intermediate 5-3 and 100 ml of dry tert-butylbenzene were added to a 250 ml three-necked flask, cooled to -30 degrees Celsius in a N2 atmosphere, and (21 mmol) of t-BuLi n-hexane solution was added dropwise. The temperature was raised to 60 degrees Celsius for reaction for 2 hours, and the n-hexane solvent was evaporated under reduced pressure. The reaction solution was cooled to -30 degrees Celsius again, 21 mmol of boron tribromide solution was added, and the mixture was heated to room temperature and stirred for 0.5 hours. The reaction solution was then cooled to 0 degrees Celsius, and 42 mmol of N,N-diisopropylethylamine was added. After the addition was complete, the mixture was heated to room temperature and stirred, and then the temperature was continued to be raised to 120 degrees Celsius and stirred for 3 hours. The reaction solution was cooled to room temperature. Sodium carbonate aqueous solution and ethyl acetate were added to quench the reaction. The aqueous phase was extracted with ethyl acetate and the organic phase was combined, and the solvent was evaporated to obtain a crude product, which was purified by rapid silica gel column to obtain a pure product. Recrystallization was performed with toluene and ethyl acetate to obtain a light yellow solid powder. The yield was 32.7%, MS (ASAP) = 871.5.

[0130] Example 6

[0131]

[0132] Synthesis of intermediate 6-2:

[0133] Compound 4-1 (10 mmol), compound 6-1 (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 50°C for 6 h under nitrogen atmosphere. After cooling, the solvent was removed by rotary evaporation, and the mixture was extracted and washed with water. The organic phase was subjected to column chromatography to obtain the intermediate 6-2 with a molar weight of 7.89 mmol, a yield of 78.9%, and MS (ASAP) = 432.9.

[0134] Synthesis of intermediate 6-3:

[0135] Compound 2-2 (20 mmol), compound 6-2 (10 mmol), Pd-132 (0.1 mmol), SPhos (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, and the mixture was extracted and washed with water. The organic phase was subjected to column chromatography to obtain the intermediate 6-3 with a molar weight of 3.78 mmol, a yield of 37.8%, and MS (ASAP) = 869.5.

[0136] Synthesis of compound (6): 10 mmol of intermediate 6-3 and 100 ml of dry tert-butylbenzene were added to a 250 ml three-necked flask, cooled to -30 degrees Celsius in a N2 atmosphere, and (21 mmol) of t-BuLi n-hexane solution was added dropwise. The temperature was raised to 60 degrees Celsius for reaction for 2 hours, and the n-hexane solvent was evaporated under reduced pressure. The reaction solution was cooled to -30 degrees Celsius again, 21 mmol of boron tribromide solution was added, and the mixture was heated to room temperature and stirred for 0.5 hours. The reaction solution was then cooled to 0 degrees Celsius, and 42 mmol of N,N-diisopropylethylamine was added. After the addition was complete, the mixture was heated to room temperature and stirred, and then the temperature was continued to be raised to 120 degrees Celsius and stirred for 3 hours. The reaction solution was cooled to room temperature. Sodium carbonate aqueous solution and ethyl acetate were added to quench the reaction. The aqueous phase was extracted with ethyl acetate and the organic phase was combined, and the solvent was evaporated to obtain a crude product, which was purified by rapid silica gel column to obtain a pure product. Recrystallization was performed with toluene and ethyl acetate to obtain a light yellow solid powder. The yield was 40.8%, MS (ASAP) = 843.5.

[0137] Example 7

[0138]

[0139] Synthesis of intermediate 7-2:

[0140] Compound 1-1 (10 mmol), compound 7-1 (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 50°C for 6 h under nitrogen atmosphere. After cooling, the solvent was removed by rotary evaporation, and the mixture was extracted and washed with water. The organic phase was subjected to column chromatography to obtain the intermediate 7-2 with a molar weight of 7.12 mmol, a yield of 71.2%, and MS (ASAP) = 384.5.

[0141] Synthesis of intermediate 7-4:

[0142] Compound 4-1 (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 and stirred at 50°C for 6 h under nitrogen atmosphere. After cooling, the solvent was removed by rotary evaporation, and the mixture was extracted and washed with water. The organic phase was subjected to column chromatography to obtain intermediate 7-4 with a molar weight of 5.49 mmol, a yield of 54.9%, and MS (ASAP) = 491.0.

[0143] Synthesis of intermediate 7-5:

[0144] Compound 7-2 (20 mmol), compound 7-4 (10 mmol), Pd-132 (0.1 mmol), SPhos (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, and the mixture was extracted and washed with water. The organic phase was subjected to column chromatography to obtain the intermediate 7-5 with a molar weight of 4.98 mmol, a yield of 49.8%, and MS (ASAP) = 1099.7.

[0145] Synthesis of compound (7): 10 mmol of intermediate 7-5 and 100 ml of dry tert-butylbenzene were added to a 250 ml three-necked flask, cooled to -30 degrees Celsius in a N2 atmosphere, and (21 mmol) of t-BuLi n-hexane solution was added dropwise. The temperature was raised to 60 degrees Celsius for reaction for 2 hours, and the n-hexane solvent was evaporated under reduced pressure. The reaction solution was cooled to -30 degrees Celsius again, 21 mmol of boron tribromide solution was added, and the mixture was heated to room temperature and stirred for 0.5 hours. The reaction solution was then cooled to 0 degrees Celsius, and 42 mmol of N,N-diisopropylethylamine was added. After the addition was complete, the mixture was heated to room temperature and stirred, and then the temperature was continued to be raised to 120 degrees Celsius and stirred for 3 hours. The reaction solution was cooled to room temperature. Sodium carbonate aqueous solution and ethyl acetate were added to quench the reaction. The aqueous phase was extracted with ethyl acetate and the organic phase was combined, and the solvent was evaporated to obtain a crude product, which was purified by rapid silica gel column to obtain a pure product. Recrystallization was performed with toluene and ethyl acetate to obtain a light yellow solid powder. The yield was 62.5%, MS (ASAP) = 1073.6.

[0146] Example 8

[0147]

[0148] Synthesis of intermediate 8-2:

[0149] Compound 1-1 (10 mmol), compound 8-1 (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 50°C for 6 h under nitrogen atmosphere. After cooling, the solvent was removed by rotary evaporation, and the mixture was extracted and washed with water. The organic phase was subjected to column chromatography to obtain intermediate 8-2 with a molar weight of 8.48 mmol, a yield of 84.8%, and MS (ASAP) = 384.7.

[0150] Synthesis of intermediate 8-4:

[0151] Compound 4-1 (10 mmol), compound 8-3 (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 50°C for 6 h under nitrogen atmosphere. After cooling, the solvent was removed by rotary evaporation, and the mixture was extracted and washed with water. The organic phase was subjected to column chromatography to obtain intermediate 8-4 with a molar weight of 5.05 mmol, a yield of 50.5%, and MS (ASAP) = 575.3.

[0152] Synthesis of intermediate 8-5:

[0153] Compound 8-2 (20 mmol), compound 8-4 (10 mmol), Pd-132 (0.1 mmol), Sphos (0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100°C for 6 h under nitrogen atmosphere. After cooling, the solvent was removed by rotary evaporation, and the liquid was extracted and washed with water. The organic phase was subjected to column chromatography to obtain the intermediate 8-5 with a molar weight of 3.56 mmol and a yield of 35.6%. MS (ASAP) = 1183.6

[0154] Synthesis of compound (8): 10 mmol of intermediate 8-5 and 100 ml of dry tert-butylbenzene were added to a 250 ml three-necked flask, cooled to -30 degrees Celsius in a N2 atmosphere, and (21 mmol) of t-BuLi n-hexane solution was added dropwise. The temperature was raised to 60 degrees Celsius for reaction for 2 hours, and the n-hexane solvent was evaporated under reduced pressure. The reaction solution was cooled to -30 degrees Celsius again, 21 mmol of boron tribromide solution was added, and the mixture was heated to room temperature and stirred for 0.5 hours. The reaction solution was then cooled to 0 degrees Celsius, and 42 mmol of N,N-diisopropylethylamine was added. After the addition was complete, the mixture was heated to room temperature and stirred, and then the temperature was continued to be raised to 120 degrees Celsius and stirred for 3 hours. The reaction solution was cooled to room temperature. Sodium carbonate aqueous solution and ethyl acetate were added to quench the reaction. The aqueous phase was extracted with ethyl acetate and the organic phase was combined, and the solvent was evaporated to obtain a crude product, which was purified by rapid silica gel column to obtain a pure product. Recrystallization was performed with toluene and ethyl acetate to obtain a light yellow solid powder. The yield was 30.6%, MS (ASAP) = 1157.2.

[0155] Example 9

[0156]

[0157] Synthesis of intermediate 9-2:

[0158] Compound 1-1 (10 mmol), compound 9-1 (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 50°C for 6 h under nitrogen atmosphere. After cooling, the solvent was removed by rotary evaporation, and the mixture was extracted and washed with water. The organic phase was subjected to column chromatography to obtain intermediate 9-2 with a molar weight of 8.33 mmol, a yield of 83.3%, and MS (ASAP) = 334.4.

[0159] Synthesis of intermediate 9-4:

[0160] Compound 9-2 (20 mmol), compound 9-3 (10 mmol), Pd-132 (0.1 mmol), Sphos (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, and the mixture was extracted and washed with water. The organic phase was subjected to column chromatography to obtain intermediate 9-4 with a molar weight of 2.87 mmol, a yield of 28.7%, and MS (ASAP) = 840.5.

[0161] Synthesis of compound (9): 10 mmol of intermediate 9-4 and 100 ml of dry tert-butylbenzene were added to a 250 ml three-necked flask, cooled to -30 degrees Celsius in a N2 atmosphere, and (21 mmol) of t-BuLi n-hexane solution was added dropwise. The temperature was raised to 60 degrees Celsius for reaction for 2 hours, and the n-hexane solvent was evaporated under reduced pressure. The reaction solution was cooled to -30 degrees Celsius again, 21 mmol of boron tribromide solution was added, and the mixture was heated to room temperature and stirred for 0.5 hours. The reaction solution was then cooled to 0 degrees Celsius, and 42 mmol of N,N-diisopropylethylamine was added. After the addition was complete, the mixture was heated to room temperature and stirred, and then the temperature was continued to be raised to 120 degrees Celsius and stirred for 3 hours. The reaction solution was cooled to room temperature. Sodium carbonate aqueous solution and ethyl acetate were added to quench the reaction. The aqueous phase was extracted with ethyl acetate and the organic phase was combined, and the solvent was evaporated to obtain a crude product, which was purified by rapid silica gel column to obtain a pure product. Recrystallization was performed with toluene and ethyl acetate to obtain a light yellow solid powder. The yield was 43.9%, MS (ASAP) = 814.6.

[0162] Example 10

[0163]

[0164] Synthesis of intermediate 10-1:

[0165] Compound 1-3 (20 mmol), compound 9-3 (10 mmol), Pd-132 (0.1 mmol), SPhos (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, and the mixture was extracted and washed with water. The organic phase was subjected to column chromatography to obtain the intermediate 10-1 with a molar weight of 4.69 mmol, a yield of 46.9%, and MS (ASAP) = 740.5.

[0166] Synthesis of compound (10): 10 mmol of intermediate 10-1 and 100 ml of dry tert-butylbenzene were added to a 250 ml three-necked flask, cooled to -30 degrees Celsius in a N2 atmosphere, and (21 mmol) of t-BuLi n-hexane solution was added dropwise. The temperature was raised to 60 degrees Celsius for reaction for 2 hours, and the n-hexane solvent was evaporated under reduced pressure. The reaction solution was cooled to -30 degrees Celsius again, 21 mmol of boron tribromide solution was added, and the mixture was stirred at room temperature for 0.5 hours, then the reaction solution was cooled to 0 degrees Celsius, 42 mmol of N,N-diisopropylethylamine was added, and after the addition was complete, the mixture was heated to room temperature and stirred, and then the temperature was continued to be raised to 120 degrees Celsius and stirred for 3 hours, and the reaction solution was cooled to room temperature. Sodium carbonate aqueous solution and ethyl acetate were added to quench the reaction. The aqueous phase was extracted with ethyl acetate and the organic phase was combined, and the solvent was evaporated to obtain a crude product, which was purified by rapid silica gel column to obtain a pure product. Recrystallization was performed with toluene and ethyl acetate to obtain a light yellow solid powder. The yield was 51.3%, MS (ASAP) = 714.7.

[0167] Embodiment 11

[0168]

[0169] Synthesis of intermediate 11-2:

[0170] Compound 1-3 (20 mmol), compound 11-1 (10 mmol), Pd-132 (0.1 mmol), Sphos (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, and the mixture was extracted and washed with water. The organic phase was subjected to column chromatography to obtain the intermediate 11-2 with a molar weight of 5.08 mmol, a yield of 50.8%, and MS (ASAP) = 726.6.

[0171] Synthesis of compound (11): 10 mmol of intermediate 11-2 and 100 ml of dry tert-butylbenzene were added to a 250 ml three-necked flask, cooled to -30 degrees Celsius in a N2 atmosphere, and (21 mmol) of t-BuLi n-hexane solution was added dropwise. The temperature was raised to 60 degrees Celsius for reaction for 2 hours, and the n-hexane solvent was evaporated under reduced pressure. The reaction solution was cooled to -30 degrees Celsius again, 21 mmol of boron tribromide solution was added, and the mixture was heated to room temperature and stirred for 0.5 hours. The reaction solution was then cooled to 0 degrees Celsius, and 42 mmol of N,N-diisopropylethylamine was added. After the addition was complete, the mixture was heated to room temperature and stirred, and then the temperature was continued to be raised to 120 degrees Celsius and stirred for 3 hours. The reaction solution was cooled to room temperature. Sodium carbonate aqueous solution and ethyl acetate were added to quench the reaction. The aqueous phase was extracted with ethyl acetate and the organic phase was combined, and the solvent was evaporated to obtain a crude product, which was purified by rapid silica gel column to obtain a pure product. Recrystallization was performed with toluene and ethyl acetate to obtain a light yellow solid powder. The yield was 46.7%, MS (ASAP) = 700.4.

[0172] Example 12

[0173]

[0174] Synthesis of intermediate 12-2:

[0175] Compound 12-1 (10 mmol), compound 1-2 (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 nitrogen atmosphere. After cooling, the solvent was removed by rotary evaporation, and the mixture was extracted and washed with water. The organic phase was subjected to column chromatography to obtain the intermediate 12-2 with a molar weight of 7.15 mmol, a yield of 71.5%, and MS (ASAP) = 520.3.

[0176] Synthesis of intermediate 12-3:

[0177] Compound 12-2 (20 mmol), compound 1-4 (10 mmol), Pd-132 (0.1 mmol), Sphos (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, and the mixture was extracted and washed with water. The organic phase was subjected to column chromatography to obtain the intermediate 12-3 with a molar weight of 3.58 mmol, a yield of 35.8%, and MS (ASAP) = 1148.4.

[0178] Synthesis of compound (12): 10 mmol of intermediate 12-3 and 100 ml of dry tert-butylbenzene were added to a 250 ml three-necked flask, cooled to -30 degrees Celsius in a N2 atmosphere, and (21 mmol) of t-BuLi n-hexane solution was added dropwise. The temperature was raised to 60 degrees Celsius for reaction for 2 hours, and the n-hexane solvent was removed under reduced pressure. The reaction solution was cooled to -30 degrees Celsius again, 21 mmol of boron tribromide solution was added, and the mixture was heated to room temperature and stirred for 0.5 hours. The reaction solution was then cooled to 0 degrees Celsius, and 42 mmol of N,N-diisopropylethylamine was added. After the addition was complete, the mixture was heated to room temperature and stirred, and then the temperature was continued to be raised to 120 degrees Celsius and stirred for 3 hours. The reaction solution was cooled to room temperature. Sodium carbonate aqueous solution and ethyl acetate were added to quench the reaction. The aqueous phase was extracted with ethyl acetate and the organic phase was combined, and the solvent was evaporated to obtain a crude product, which was purified by rapid silica gel column to obtain a pure product. Recrystallization was performed with toluene and ethyl acetate to obtain a light yellow solid powder. The yield was 40.1%, MS (ASAP) = 1122.6.

[0179] Example 13

[0180]

[0181] Synthesis of intermediate 13-2:

[0182] Compound 13-1 (10 mmol), compound 9-1 (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 50°C for 6 h under nitrogen atmosphere. After cooling, the solvent was removed by rotary evaporation, and the mixture was extracted and washed with water. The organic phase was subjected to column chromatography to obtain intermediate 13-2 with a molar weight of 8.57 mmol, a yield of 85.7%, and MS (ASAP) = 368.4.

[0183] Synthesis of intermediate 13-4:

[0184] Compound 13-2 (10 mmol), compound 13-3 (10 mmol), Pd-132 (0.1 mmol), SPhos (0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100°C for 6 h under nitrogen atmosphere. After cooling, the solvent was removed by rotary evaporation, and the liquid was extracted and washed with water. The organic phase was subjected to column chromatography to obtain the intermediate 13-4 with a molar weight of 5.71 mmol and a yield of 51.7%. MS (ASAP) = 377.4

[0185] Synthesis of intermediate 13-5:

[0186] Compound 13-4 (20 mmol), compound 1-4 (10 mmol), Pd-132 (0.1 mmol), SPhos (0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100°C for 6 h under nitrogen atmosphere. After cooling, the solvent was removed by rotary evaporation, and the mixture was extracted and washed with water. The organic phase was subjected to column chromatography to obtain intermediate 13-5 with a molar weight of 4.68 mmol and a yield of 46.8%. MS (ASAP) = 862.5.

[0187] Synthesis of compound (13): 10 mmol of intermediate 13-5 and 100 ml of dry tert-butylbenzene were added to a 250 ml three-necked flask, cooled to -30 degrees Celsius in a N2 atmosphere, and (21 mmol) of t-BuLi n-hexane solution was added dropwise. The temperature was raised to 60 degrees Celsius for reaction for 2 hours, and the n-hexane solvent was evaporated under reduced pressure. The reaction solution was cooled to -30 degrees Celsius again, 21 mmol of boron tribromide solution was added, and the mixture was heated to room temperature and stirred for 0.5 hours. The reaction solution was then cooled to 0 degrees Celsius, and 42 mmol of N,N-diisopropylethylamine was added. After the addition was complete, the mixture was heated to room temperature and stirred, and then the temperature was continued to be raised to 120 degrees Celsius and stirred for 3 hours. The reaction solution was cooled to room temperature. Sodium carbonate aqueous solution and ethyl acetate were added to quench the reaction. The aqueous phase was extracted with ethyl acetate and the organic phase was combined, and the solvent was evaporated to obtain a crude product, which was purified by rapid silica gel column to obtain a pure product. Recrystallization was performed with toluene and ethyl acetate to obtain a light yellow solid powder. The yield was 37.6%, MS (ASAP) = 836.7.

[0188] Embodiment 14

[0189]

[0190] Synthesis of intermediate 14-2:

[0191] Compound 14-1 (10 mmol), compound 1-2 (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 nitrogen atmosphere. After cooling, the solvent was removed by rotary evaporation, and the mixture was extracted and washed with water. The organic phase was subjected to column chromatography to obtain the intermediate 14-2 with a molar weight of 7.11 mmol, a yield of 71.1%, and MS (ASAP) = 334.

[0192] Synthesis of intermediate 14-3:

[0193] Compound 14-2 (20 mmol), compound 11-1 (10 mmol), Pd-132 (0.1 mmol), SPhos (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, and the mixture was extracted and washed with water. The organic phase was subjected to column chromatography to obtain the intermediate 14-3 with a molar weight of 5.67 mmol, a yield of 56.7%, and MS (ASAP) = 826.

[0194] Synthesis of compound (14): 10 mmol of intermediate 11-2 and 100 ml of dry tert-butylbenzene were added to a 250 ml three-necked flask, cooled to -30 degrees Celsius in a N2 atmosphere, and (21 mmol) of t-BuLi n-hexane solution was added dropwise. The temperature was raised to 60 degrees Celsius for reaction for 2 hours, and the n-hexane solvent was evaporated under reduced pressure. The reaction solution was cooled to -30 degrees Celsius again, 21 mmol of boron tribromide solution was added, and the mixture was heated to room temperature and stirred for 0.5 hours. The reaction solution was then cooled to 0 degrees Celsius, and 42 mmol of N,N-diisopropylethylamine was added. After the addition was complete, the mixture was heated to room temperature and stirred, and then the temperature was continued to be raised to 120 degrees Celsius and stirred for 3 hours. The reaction solution was cooled to room temperature. Sodium carbonate aqueous solution and ethyl acetate were added to quench the reaction. The aqueous phase was extracted with ethyl acetate and the organic phase was combined, and the solvent was evaporated to obtain a crude product, which was purified by rapid silica gel column to obtain a pure product. Recrystallization was performed with toluene and ethyl acetate to obtain a light yellow solid powder. The yield was 46.7%, MS (ASAP)=800.

[0195] Preparation and performance characterization of OLED devices

[0196]

[0197] The above materials BH, ET, Liq, and BD-Ref are all commercially available, or their synthesis methods are prior art, which are detailed in the references in the prior art and will not be described here. Among them, BH is used as the host material, ET is used as the electron transport material, and Liq is used as the electron injection material.

[0198] The following is a detailed description of the preparation process of an OLED device using the above compounds through a specific embodiment. The structure of the OLED device is: ITO / HIL / HTL / EML / ETL / cathode, and its structural schematic diagram is shown in FIG. Figure 1 As shown, 101 is a substrate, 102 is an anode, 103 is a hole injection layer (HIL), 104 is a hole transport layer (HTL), 105 is a light emitting layer, 106 is an electron transport layer (ETL), and 107 is a cathode. The preparation steps are as follows:

[0199] a. Cleaning of ITO (indium tin oxide) conductive glass substrates: using various solvents (such as one or more of chloroform, acetone or isopropyl alcohol) for cleaning, followed by ultraviolet ozone treatment;

[0200] b. HIL (hole injection layer, 40nm): 60nm PEDOT (polyethylenedioxythiophene, Clevios TM AI4083) was spin-coated as HIL in a clean room and treated on a hot plate at 180 °C for 10 min;

[0201] c. HTL (hole transport layer, 20 nm): 20 nm of TFB or PVK (Sigma Aldrich, average Mn 25,000-50,000) was prepared by spin coating in a nitrogen glove box. The solution used was TFB or PVK added to toluene solvent at a concentration of 5 mg / ml, followed by treatment on a hot plate at 180 °C for 60 min.

[0202] d. EML (organic light-emitting layer, 40 nm): EML is formed by spin coating in a nitrogen glove box. The solution used is a methyl benzoate solution of different host and guest (the weight ratio of host and guest is 95:5), the solution solubility is 15 mg / ml, and then it is treated on a hot plate at 140°C for 10 minutes. The host material is BH, and the guest uses the compounds listed in the examples of this patent and the comparative compounds. Other implementation schemes are the same.

[0203] e. Electron transport layer and cathode: The heat-treated substrate was transferred to a vacuum chamber, and then ET and LiQ were placed in different evaporation units under high vacuum (1×10 -6 The two layers were co-deposited at a ratio of 50 wt % in 400 mbar (0.1 wt %) to form an electron transport layer with a thickness of 20 nm on the light-emitting layer, and then an Al cathode with a thickness of 100 nm was deposited.

[0204] f. Packaging: The device is packaged with UV-curable resin in a nitrogen glove box.

[0205] The current-voltage (JV) characteristics of each OLED device were characterized using a characterization device, while recording important parameters such as efficiency, lifetime, and external quantum efficiency, as shown in Table 1:

[0206] Table 1

[0207]

[0208] The current-voltage (JV) characteristics of each OLED device are characterized by characterization equipment, and important parameters such as efficiency, lifespan and external quantum efficiency are recorded at the same time. After testing, the color coordinates CIE of the blue light device prepared using compound 1-compound 14 as the guest material in the EML layer light-emitting layer is better than that of the blue light device prepared using the comparative compound 1 as the guest material in the EML layer light-emitting layer. In addition, the luminous efficiency CE of the blue light device prepared using compound 1-compound 14 as the main material in the EML layer light-emitting layer is in the range of 5.6-6.2cd / A, with more excellent luminous efficiency. The luminous efficiency CE of the blue light device prepared using compounds 2, 3, 6, and 13 as the main material in the EML layer light-emitting layer is in the range of 6.0-6.2cd / A, and the lifespan LT is about 160h, with the best luminous efficiency and lifespan. This is because an alkyl chain is introduced at the 2 and 3 positions of the indole in the compound, which makes the overall molecule more soluble and facilitates compound purification, thereby improving the purity of the compound and further improving the device performance; since diphenylamine groups are introduced into the benzene rings on both sides of the boron in the comparison compound 1, the hole transport ability of the molecule is enhanced, so the lifespan of the blue light device prepared using compounds 1 to 14 as the main materials in the EML layer light-emitting layer is better than that of the comparison compound 1 (generally increased by 90%-100%).

[0209] The technical features of the above-described embodiments may be arbitrarily combined. To make the description concise, not all possible combinations of the technical features in the above-described embodiments are described. However, as long as there is no contradiction in the combination of these technical features, they should be considered to be within the scope of this specification.

[0210] The above-described embodiments only express several implementation methods of the present invention, which are convenient for understanding the technical solutions of the present invention in detail, but they cannot be understood as limiting the scope of protection of the invention patent. It should be pointed out that for ordinary technicians in this field, several modifications and improvements can be made without departing from the concept of the present invention, which all belong to the protection scope of the present invention. It should be understood that the technical solutions obtained by those skilled in the art through logical analysis, reasoning or limited experiments on the basis of the technical solutions provided by the present invention are all within the protection scope of the claims attached to the present invention. Therefore, the protection scope of the patent of the present invention shall be based on the contents of the attached claims, and the description and drawings can be used to interpret the contents of the claims.

Claims

1. An organic compound, characterized in that The organic compound is a boron-containing indole diphenylamine organic compound, and the organic compound is selected from compounds 2, 3, 6 and 13. The structures of compounds 2, 3, 6 and 13 are shown in the following general formula:

2. A mixture, characterized in that It comprises the organic compound as described in claim 1 and at least one organic functional material, wherein the organic functional material is selected from at least one of hole injection materials, hole transport materials, electron transport materials, electron injection materials, electron blocking materials, hole blocking materials, luminophores, luminescent host materials and organic dyes.

3. A composition, characterized in that The method comprises the organic compound as claimed in claim 1 or the mixture as claimed in claim 2 and at least one organic solvent.

4. An organic electronic device, characterized in that: Comprising the organic compound as claimed in claim 1 or the mixture as claimed in claim 2.

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