Organic compounds and mixtures, compositions and organic electronic devices comprising the same

Abstract

The present application discloses an organic compound having the following structure: #imgabs0# Ar1 is selected from an aryl group, a heteroaryl group, or a combination of these groups; L1 and L2 are each independently selected from a single bond, an aryl group, or a heteroaryl group; R1, R2, and R3 are each independently selected from -D, a linear alkyl group, a linear alkoxy group, a linear thioalkoxy group, a branched alkyl group, a branched alkoxy group, a branched thioalkoxy group, a cyclic alkyl group, a cyclic alkoxy group, a cyclic thioalkoxy group, a silyl group, a keto group, an alkoxycarbonyl group, an aryloxycarbonyl 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, an aryl group, a heteroaryl group, an aryloxy group, a heteroaryloxy group, or a combination of these groups; m1 is an integer selected from 0 to 8, and m2 and m3 are each independently an integer selected from 0 to 4. Additionally, the present application also discloses a mixture, a composition, and an organic electronic device.

Description

Technical Field

[0001] This application relates to the technical field of luminescent materials, and particularly to an organic compound, a mixture, a composition, and an organic electronic device including the organic compound. 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 such as wide viewing angles, fast response times, low operating voltages, and thin panel thicknesses in the applications of optoelectronic devices (such as flat panel displays and lighting), and thus have broad development potential.

[0003] Organic electroluminescence refers to the phenomenon of converting electrical energy into light energy using organic substances. An organic electroluminescent element using the organic electroluminescence phenomenon usually has a structure including a positive electrode and a negative electrode and an organic layer between them. To improve the efficiency and lifespan of the organic electroluminescent element, the organic layer has a multi-layer structure, and each layer contains different organic substances. Specifically, it may include a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, etc. In such an organic electroluminescent element, when a voltage is applied between the two electrodes, holes are injected into the organic layer from the positive electrode, and electrons are injected into the organic layer from the negative electrode. When the injected holes and electrons meet, excitons are formed, and light is emitted when the excitons transition back to the ground state. Such an organic electroluminescent element has characteristics such as self-luminescence, high brightness, high efficiency, low driving voltage, wide viewing angle, high contrast, and high responsiveness.

[0004] To improve the luminous efficiency of organic electroluminescent elements, various luminescent material systems based on fluorescence and phosphorescence have been developed. However, for both fluorescent materials and phosphorescent materials, the development of excellent blue light materials is a huge challenge. Currently, most blue fluorescent materials have broad emission spectra and poor color purity, which is not conducive to high-end displays. Moreover, the synthesis of such fluorescent materials is relatively complex, which is not conducive to large-scale production. At the same time, the stability of organic electroluminescent elements using such blue fluorescent materials needs to be further improved.

[0005] Currently, the light-emitting layer of blue organic electroluminescent elements adopts a host-guest doping structure. Although most blue host materials are based on anthracene-fused ring derivatives, the material stability of these compounds is poor, resulting in poor device lifespan. At the same time, it is difficult for these compounds to achieve deep blue light emission. Therefore, there are problems in realizing full-color displays.

[0006] Therefore, there is still a need to further improve the materials to improve the performance of organic electroluminescent devices. Summary of the Invention

[0007] In view of this, the present application provides a blue-light fluorescent organic compound, aiming to improve the problems of low luminous efficiency and short lifespan of existing blue-light fluorescent organic electronic devices.

[0008] The present application is achieved through the following technical solutions:

[0009] An organic compound having a structure represented by the general formula (1):

[0010]

[0011] Wherein:

[0012] Ar1 is independently selected from a substituted or unsubstituted aromatic group containing 6 to 60 ring atoms, a substituted or unsubstituted heteroaromatic group containing 6 to 60 ring atoms, or a combination of these groups;

[0013] L1 and L2 are each independently selected from a single bond, a substituted or unsubstituted aromatic group containing 6 to 60 ring atoms, or a substituted or unsubstituted heteroaromatic group containing 6 to 60 ring atoms;

[0014] Each occurrence of R1, R2, and R3 is independently selected from -D, a straight-chain alkyl group having 1 to 20 C atoms, a straight-chain alkoxy group having 1 to 20 C atoms, a straight-chain thioalkoxy group having 1 to 20 C atoms, a branched-chain alkyl group having 3 to 20 C atoms, a branched-chain alkoxy group having 3 to 20 C atoms, a branched-chain thioalkoxy group having 3 to 20 C atoms, a cyclic alkyl group having 3 to 20 C atoms, a cyclic alkoxy group having 3 to 20 C atoms, a cyclic thioalkoxy group having 3 to 20 C atoms, a silyl group, a keto group having 1 to 20 C atoms, an alkoxycarbonyl group having 2 to 20 C atoms, an aryloxycarbonyl group having 7 to 20 C atoms, 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, a substituted or unsubstituted aromatic group having 6 to 60 ring atoms, a substituted or unsubstituted heteroaromatic group having 5 to 60 ring atoms, a substituted or unsubstituted aryloxy group having 5 to 60 ring atoms, a substituted or unsubstituted heteroaryloxy group having 5 to 60 ring atoms, or a combination of these groups;

[0015] m1 is 0, 1, 2, 3, 4, 5, 6, 7, or 8;

[0016] m2 is 0, 1, 2, 3, or 4;

[0017] m3 is 0, 1, 2, 3, or 4.

[0018] Correspondingly, the present application also provides a mixture, comprising the above-mentioned organic compound and at least one organic functional material, and the organic functional material is selected from a hole injection material, a hole transport material, an electron transport material, an electron injection material, an electron blocking material, a hole blocking material, a light-emitting material, a host material, a guest material or an organic dye.

[0019] Correspondingly, the present application also provides a composition, comprising the above-mentioned organic compound or the above-mentioned mixture, and at least one organic solvent.

[0020] Correspondingly, the present application also provides an organic electronic device, comprising at least one functional layer, and the functional layer contains the above-mentioned organic compound or the above-mentioned mixture, or the functional layer is prepared from the above-mentioned composition.

[0021] Compared with the prior art, the organic compound of the present invention has the following beneficial effects:

[0022] The anthracene derivative containing a heterocyclic fused ring of the present invention can be used as a host material in the light-emitting layer of an organic electronic device. Such an organic compound has fluorescence emission at a blue light wavelength, so this kind of substance can be used in a blue light organic light-emitting electronic device, and has a high device luminous efficiency and a long device life. Description of the Drawings

[0023] In order to more clearly illustrate the technical solutions in the embodiments of the present application, the following will briefly introduce the drawings required for the description of the embodiments. Obviously, the following drawings are only some embodiments of the present application. For those skilled in the art, without creative efforts, other drawings can be obtained according to these drawings.

[0024] Figure 1 It is a schematic diagram of the OLED device shown in Embodiment 1 of the device of the present invention;

[0025] Among them, 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. Detailed Embodiments

[0026] Next, the technical solutions in the embodiments of the present application will be clearly and completely described in conjunction with the accompanying drawings in the embodiments of the present application. Obviously, the described embodiments are only a part of the embodiments of the present application, rather than all the embodiments. Based on the embodiments in the present application, all other embodiments obtained by those skilled in the art without creative efforts belong to the scope of protection of the present application. In addition, it should be understood that the specific implementation manners described herein are only used to illustrate and explain the present application, and are not used to limit the present application. In the description of the present application, the term "including" means "including but not limited to", and the term "a plurality of" means "two or more". The various embodiments of the present application may exist in the form of a range; it should be understood that the description in the form of a range is only for convenience and brevity, and should not be construed as a rigid limitation on the scope of the present application; therefore, it should be considered that the described range description has specifically disclosed all possible sub-ranges and single values within that range. For example, it should be considered that the range description from 1 to 6 has specifically disclosed sub-ranges such as from 1 to 3, from 1 to 4, from 1 to 5, from 2 to 4, from 2 to 6, from 3 to 6, etc., and single numbers within that range, such as 1, 2, 3, 4, 5, and 6, regardless of the range. Additionally, whenever a numerical range is indicated herein, it means including any cited number (fraction or integer) within the indicated range.

[0027] Unless otherwise defined, all technical and scientific terms used herein have the same meaning as commonly understood by those of ordinary skill in the technical field to which this application belongs. The terms used in the description of this application herein 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 of the related listed items.

[0028] In the present application, the terms "composition", "printing ink", and "ink" have the same meaning and can be used interchangeably.

[0029] In the present application, the terms "aromatic group", "aromatic", and "aromatic ring system" have the same meaning and can be used interchangeably.

[0030] In the present application, the terms "heteroaromatic group", "heteroaromatic", and "heteroaromatic ring system" have the same meaning and can be used interchangeably.

[0031] In the present application, "substituted" means that a hydrogen atom in a substituent is replaced by a substituent. In the present application, "substituted or unsubstituted" means that the defined group may be substituted or may not be substituted. When the defined group is substituted, it should be understood that the defined group may be substituted by one or more substituents R, where R is selected from, but not limited to, a deuterium atom, a cyano group, an isocyano group, a nitro group, a halogen, an alkyl group containing 1-30 C atoms, 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 silyl group, a carbonyl group, an alkoxycarbonyl group, an aryloxycarbonyl group, a carbamoyl group, a halocarbonyl group, a formyl group, an isocyanate group, a thiocyanate group, an isothiocyanate group, a hydroxyl group, and a trifluoromethyl group, and the above groups may also be further substituted by substituents acceptable in the art; it can be understood that R’ and R” in -NR’R” are each independently selected from, but not limited to, H, a deuterium atom, a cyano group, an isocyano group, a nitro group, or a halogen, a C 1-10 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. 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 C 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 halocarbonyl group, a formyl group, an isocyanate group, a thiocyanate group, an isothiocyanate group, a hydroxyl group, and a trifluoromethyl group, and the above groups may also be further substituted by substituents acceptable in the art.

[0032] In the present application, "number of ring atoms" means the number of atoms among the atoms constituting the ring itself in a structural compound obtained by bonding atoms in a ring (for example, a monocyclic compound, a fused-ring compound, a crosslinked compound, a carbocyclic compound, a heterocyclic compound). When the ring is substituted by a substituent, the atoms contained in the substituent are not included in the ring-forming atoms. The same applies to the "number of ring atoms" described below under the condition of no special description. For example, the number of ring atoms in a benzene ring is 6, the number of ring atoms in a naphthalene ring is 10, and the number of ring atoms in a thienyl group is 5.

[0033] "Aryl or aromatic group" refers to an aromatic hydrocarbon group derived by removing one hydrogen atom from an aromatic ring compound, which can be a monocyclic aryl group, a fused-ring aryl group, or a polycyclic aryl group. For a polycyclic ring, at least one is an aromatic ring system. For example, "substituted or unsubstituted aryl group having 6 to 40 ring atoms" refers to an aryl group containing 6 to 40 ring atoms, preferably a substituted or unsubstituted aryl group having 6 to 30 ring atoms, more preferably a substituted or unsubstituted aryl group having 6 to 18 ring atoms, and particularly preferably a substituted or unsubstituted aryl group having 6 to 14 ring atoms; suitable examples include, but are not limited to, phenyl, biphenyl, terphenyl, naphthyl, anthryl, phenanthryl, fluoranthenyl, triphenylenyl, pyrenyl, perylenyl, tetracenyl, fluorenyl, dibenzofluorenyl, acenaphthylenyl and their derivatives. It is understood that multiple aryl groups can also be interrupted by short non-aromatic units (e.g., <10% non-H atoms such as C, N or O atoms), specifically, acenaphthene, fluorene, 9,9-diarylfluorene, triarylamine or diaryl ether systems should also be included in the definition of aryl groups.

[0034] "Heteroaryl or heteroaromatic group" refers to a group in which at least one carbon atom in an aryl group is replaced by a non-carbon atom, and the non-carbon atom can be an N atom, an O atom, an S atom, etc. For example, "substituted or unsubstituted heteroaryl 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, and the heteroaryl group is optionally further substituted. Suitable examples include, but are not limited to, thienyl, furyl, pyrrolyl, imidazolyl, oxadiazolyl, triazolyl, imidazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, acridinyl, pyridazinyl, pyrazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, benzothienyl, benzofuryl, indolyl, pyrroloimidazolyl, pyrrolopyrrolyl, thienopyrrolyl, thienothienyl, furanopyrrolyl, furanofuryl, thienofuryl, benzisoxazolyl, benzisothiazolyl, benzimidazolyl, phthalazinyl, phenanthridinyl, perimidinyl, quinazolinone, dibenzothienyl, dibenzofuryl, carbazolyl and their derivatives.

[0035] In the present application, "alkyl" may represent straight-chain, branched-chain, and / or cyclic alkyl. The number of carbon atoms in the alkyl may be 1 to 50, 1 to 30, 1 to 20, 1 to 10, or 1 to 6. Non-limiting examples of alkyl 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, adamantyl, etc.

[0036] In the present application, "halogen" or "halo group" refers to F, Cl, Br, or I.

[0037] In the present application, the term "alkoxy" refers to a group having -O-alkyl, that is, the alkyl as defined above is connected to the parent nucleus structure via an oxygen atom. Suitable examples of phrases containing this term include, but are not limited to: methoxy (-O-CH3 or -OMe), ethoxy (-O-CH2CH3 or -OEt), and tert-butoxy (-O-C(CH3)3 or -OtBu).

[0038] In the present application, "amino group" refers to a derivative of an amine, having a structural feature of the formula -N(X)2, where each "X" is independently H, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted heterocyclic group, etc. Non-limiting types of amino groups include -NH2, -N(alkyl)2, -NH(alkyl), -N(cycloalkyl)2, -NH(cycloalkyl), -N(heterocyclic group)2, -NH(heterocyclic group), -N(aryl)2, -NH(aryl), -N(alkyl)(aryl), -N(alkyl)(heterocyclic group), -N(cycloalkyl)(heterocyclic group), -N(aryl)(heteroaryl), -N(alkyl)(heteroaryl), etc.

[0039] In the present application, unless otherwise defined, hydroxy refers to -OH, carboxy refers to -COOH, carbonyl refers to -C(=O)-, amino refers to -NH2, formyl refers to -C(=O)H, halocarbonyl refers to -C(=O)Z (where Z represents halogen), carbamoyl refers to -C(=O)NH2, isocyanate group refers to -NCO, and isothiocyanate group refers to -NCS.

[0040] In the present application, "*" represents the connection site.

[0041] In the present application, when there are multiple substituents with the same symbol on the same group, each substituent may be the same or different from each other. For example the 6 Rs on the benzene ring 1 may be the same or different from each other.

[0042] In the present application, the single bond to which the substituent is attached passes through the corresponding ring, indicating that the substituent can be attached to any optional position of the ring. For example in , R is attached to any substitutable site of the benzene ring; as represents can form a fused ring with any optional position on the benzene ring in .

[0043] In the embodiments of the present application, the energy level structure of the organic material, the triplet energy level ET, HOMO, and LUMO play a key role. The determination of these energy levels is introduced below.

[0044] The HOMO and LUMO energy levels can be measured by the photoelectric effect, such as XPS (X-ray photoelectron spectroscopy) and UPS (ultraviolet photoelectron spectroscopy) or by cyclic voltammetry (hereinafter referred to as CV). Recently, quantum chemical methods, such as density functional theory (hereinafter referred to as DFT), have also become effective methods for calculating the energy levels of molecular orbitals.

[0045] The triplet energy level ET1 of the organic material can be measured by low-temperature time-resolved luminescence spectroscopy or obtained by quantum simulation calculations (such as by Time-dependent DFT), such as through the commercial software Gaussian 09W (Gaussian Inc.). The specific simulation method can be referred to WO2011141110 or as described in the following examples.

[0046] It should be noted that the absolute values of HOMO, LUMO, and ET1 depend on the measurement method or calculation method used. Even for the same method, different evaluation methods, such as the starting point and peak point on the CV curve, can give different HOMO / LUMO values. Therefore, reasonable and meaningful comparisons 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 it does not affect the application of other measurement or calculation methods.

[0047] In the 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.

[0048] The cyclic alkyl or cycloalkyl as described in the present application has the same meaning and can be interchanged.

[0049] The technical solution of the present application is as follows:

[0050] ​An anthracene organic compound containing a heterocyclic fused ring has a structure shown in the general formula (1):

[0051]

[0052] Wherein:

[0053] Ar1 is selected from a substituted or unsubstituted aromatic group containing 6 to 60 ring atoms, a substituted or unsubstituted heteroaromatic group containing 6 to 60 ring atoms, or a combination of these groups;

[0054] L1 and L2 are each independently selected from a single bond, a substituted or unsubstituted aromatic group containing 6 to 60 ring atoms, or a substituted or unsubstituted heteroaromatic group containing 6 to 60 ring atoms;

[0055] Each occurrence of R1, R2, and R3 is independently selected from -D (deuterium), a straight-chain alkyl group having 1 to 20 C atoms, a straight-chain alkoxy group having 1 to 20 C atoms, a straight-chain thioalkoxy group having 1 to 20 C atoms, a branched-chain alkyl group having 3 to 20 C atoms, a branched-chain alkoxy group having 3 to 20 C atoms, a branched-chain thioalkoxy group having 3 to 20 C atoms, a cyclic alkyl group having 3 to 20 C atoms, a cyclic alkoxy group having 3 to 20 C atoms, a cyclic thioalkoxy group having 3 to 20 C atoms, a silyl group, a ketone group having 1 to 20 C atoms, an alkoxycarbonyl group having 2 to 20 C atoms, an aryloxycarbonyl group having 7 to 20 C atoms, 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, a substituted or unsubstituted aromatic group having 6 to 60 ring atoms, a substituted or unsubstituted heteroaromatic group having 5 to 60 ring atoms, a substituted or unsubstituted aryloxy group having 5 to 60 ring atoms, a substituted or unsubstituted heteroaryloxy group having 5 to 60 ring atoms, or a combination of these groups;

[0056] m1 is 0, 1, 2, 3, 4, 5, 6, 7, or 8;

[0057] m2 is 0, 1, 2, 3, or 4;

[0058] m3 is 0, 1, 2, 3, or 4.

[0059] In some preferred embodiments, each occurrence of R1, R2 and R3 is independently selected from -D, a straight-chain alkyl group having 1 to 10 carbon atoms, a straight-chain alkoxy group having 1 to 10 carbon atoms, a straight-chain thioalkoxy group having 1 to 10 carbon atoms, a branched-chain alkyl group having 3 to 10 carbon atoms, a branched-chain alkoxy group having 3 to 10 carbon atoms, a branched-chain thioalkoxy group having 3 to 10 carbon atoms, a cyclic alkyl group having 3 to 20 carbon atoms, a cyclic alkoxy group having 3 to 10 carbon atoms, a cyclic thioalkoxy group having 3 to 10 carbon atoms, a silyl group, a keto group having 1 to 10 carbon atoms, an alkoxycarbonyl group having 2 to 10 carbon atoms, an aryloxycarbonyl group having 7 to 10 carbon atoms, 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, a substituted or unsubstituted aromatic group having 6 to 30 ring atoms, a substituted or unsubstituted heteroaromatic group having 6 to 30 ring atoms, a substituted or unsubstituted aryloxy group having 6 to 30 ring atoms, a substituted or unsubstituted heteroaryloxy group having 6 to 30 ring atoms, or a combination of these groups.

[0060] In some more preferred embodiments, each occurrence of R1, R2 and R3 is independently selected from -D, a straight-chain alkyl group having 1 to 8 carbon atoms, a branched-chain alkyl group having 3 to 8 carbon atoms, a cyclic alkyl group having 3 to 8 carbon atoms, a silyl group, a cyano group, an isocyano group, a hydroxyl group, a nitro group, -CF3, -Cl, -Br, -F, a substituted or unsubstituted aromatic group having 6 to 10 ring atoms, a substituted or unsubstituted heteroaromatic group having 5 to 10 ring atoms, or a combination of these groups.

[0061] In some specific embodiments, each occurrence of R1, R2 and R3 is independently selected from -D, 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, adamantyl, phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthryl, triazinyl, pyridyl, pyrimidinyl, imidazolyl, furyl, thienyl, benzofuryl, benzothienyl, indolyl, carbazolyl, dibenzothiophenyl, dibenzofuryl, phenyl-substituted carbazolyl, fluorenyl, or a fluorenyl group substituted with an alkyl group having 1-10 carbon atoms.

[0062] In some embodiments, m2 is 0, 1 or 2.

[0063] In some embodiments, each occurrence of R2 is independently selected from -D, methyl, isopropyl, tert-butyl, or phenyl.

[0064] In some preferred embodiments, Ar1 is selected from substituted or unsubstituted aromatic groups having 6 to 30 ring atoms, or substituted or unsubstituted heteroaromatic groups having 6 to 30 ring atoms.

[0065] In some more preferred embodiments, Ar1 is selected from substituted or unsubstituted aromatic groups having 6 to 16 ring atoms, or substituted or unsubstituted heteroaromatic groups having 6 to 16 ring atoms.

[0066] In some even more preferred embodiments, Ar1 is selected from the structures shown below:

[0067]

[0068] Wherein:

[0069] Each occurrence of X is independently selected from CR4 or N;

[0070] Y is selected from NR5, CR6R7, SiR6R7, O, S, S=O, or SO2;

[0071] Each occurrence of R4, R5, R6, and R7 is independently selected from -H, -D, straight-chain alkyls having 1 to 20 C atoms, straight-chain alkoxys having 1 to 20 C atoms, straight-chain thioalkoxys having 1 to 20 C atoms, branched-chain alkyls having 3 to 20 C atoms, branched-chain alkoxys having 3 to 20 C atoms, branched-chain thioalkoxys having 3 to 20 C atoms, cyclic alkyls having 3 to 20 C atoms, cyclic alkoxys having 3 to 20 C atoms, cyclic thioalkoxys having 3 to 20 C atoms, silyl, ketones having 1 to 20 C atoms, alkoxycarbonyls having 2 to 20 C atoms, aryloxycarbonyls having 7 to 20 C atoms, cyano, carbamoyl, halocarbonyl, formyl, isocyano, isocyanate, thiocyanate, isothiocyanate, hydroxyl, nitro, amino, CF3, Cl, Br, F, I, substituted or unsubstituted aromatic groups having 6 to 60 ring atoms, substituted or unsubstituted heteroaromatic groups having 5 to 60 ring atoms, substituted or unsubstituted aryloxys having 5 to 60 ring atoms, substituted or unsubstituted heteroaryloxys having 5 to 60 ring atoms, or combinations of these groups.

[0072] R6 and R7 may form a ring with each other or not.

[0073] It is understood that when X is a connection site, X is selected from C; when Y is a connection site, Y is selected from N.

[0074] In some specific examples, the structure of the organic compound is selected from the structures represented by any of the general formulas (2-1)-(2-6):

[0075]

[0076] In some specific examples, each occurrence of R4 is independently selected from: -H, -D, a straight-chain alkyl group having 1 to 10 C atoms, a branched-chain alkyl group having 3 to 10 C atoms, a cyclic alkyl group having 3 to 10 C atoms, a silyl group, an isocyano group, a nitro group, an amino group, -CF3, -Cl, -Br, -F, -I, a substituted or unsubstituted aromatic group having 6 to 20 ring atoms, a substituted or unsubstituted heteroaromatic group having 5 to 20 ring atoms, or a combination of these groups. Further, each occurrence of R4 is independently selected from: -H, -D, a straight-chain alkyl group having 1 to 8 C atoms, a branched-chain alkyl group having 3 to 8 C atoms, a cyclic alkyl group having 3 to 8 C atoms, a substituted or unsubstituted aromatic group having 6 to 10 ring atoms, a substituted or unsubstituted heteroaromatic group having 5 to 10 ring atoms, or a combination of these groups.

[0077] The definition of the substituent is as described above. Preferably, the substituent is selected from -D, a straight-chain alkyl group having 1 to 4 C atoms, a branched-chain alkyl group having 3 to 4 C atoms, or a phenyl group, or a pyridyl group.

[0078] Furthermore, each occurrence of R4 is independently selected from: -H or -D or a phenyl group. In some embodiments, at least one R4 is selected from -D; in still some other embodiments, both R4s in the general formula (2-1) or (2-2) are selected from -D.

[0079] In some specific examples, each occurrence of R5 is independently selected from: a straight-chain alkyl group having 1 to 10 C atoms, a branched-chain alkyl group having 3 to 10 C atoms, a cyclic alkyl group having 3 to 10 C atoms, a substituted or unsubstituted aromatic group having 6 to 20 ring atoms, a substituted or unsubstituted heteroaromatic group having 5 to 20 ring atoms, or a combination of these groups; further, each occurrence of R5 is independently selected from: a substituted or unsubstituted aromatic group having 6 to 13 ring atoms, a substituted or unsubstituted heteroaromatic group having 6 to 13 ring atoms, or a combination of these groups; furthermore, each occurrence of R5 is independently selected from: a methyl group, an ethyl group, an isopropyl group, a tert-butyl group, a phenyl group, a pyridyl group, a pyrimidinyl group, a triazinyl group, a biphenyl group, a terphenyl group, or a naphthyl group.

[0080] In some specific examples, each occurrence of R6 and R7 is independently selected from: -H, -D, a straight-chain alkyl group having 1 to 8 C atoms, a branched-chain alkyl group having 3 to 8 C atoms, or a cyclic alkyl group having 3 to 8 C atoms, a substituted or unsubstituted aromatic group having 6 to 10 ring atoms, a substituted or unsubstituted heteroaromatic group having 5 to 10 ring atoms, or a combination of these groups; further, each occurrence of R6 and R7 is independently selected from: -H, -D, methyl, ethyl, isopropyl, phenyl, pyridyl, pyrimidinyl, triazinyl, biphenyl, terphenyl, or naphthyl.

[0081] In some embodiments, Ar1 is selected from any of the following groups:

[0082]

[0083] Wherein: * represents the connection site.

[0084] In some embodiments, L1 and L2 are independently selected from a single bond, a substituted or unsubstituted aromatic group having 6 to 14 ring atoms, or a substituted or unsubstituted heteroaromatic group having 6 to 14 ring atoms.

[0085] Further, L1 and L2 are independently selected from a single bond or any of the following structures:

[0086]

[0087] Wherein:

[0088] Each occurrence of X1 is independently selected from CR8 or N;

[0089] Y1 is selected from NR9, CR 10 R 11 、SiR 10 R 11 、O, S, S=O or SO2;

[0090] R8, R9, R 10 、R 11Each occurrence is independently selected from -H, -D, a straight-chain alkyl group having 1 to 20 carbon atoms, a straight-chain alkoxy group having 1 to 20 carbon atoms, a straight-chain thioalkoxy group having 1 to 20 carbon atoms, a branched-chain alkyl group having 3 to 20 carbon atoms, a branched-chain alkoxy group having 3 to 20 carbon atoms, a branched-chain thioalkoxy group having 3 to 20 carbon atoms, a cyclic alkyl group having 3 to 20 carbon atoms, a cyclic alkoxy group having 3 to 20 carbon atoms, a cyclic thioalkoxy group having 3 to 20 carbon atoms, a silyl group, a keto group having 1 to 20 carbon atoms, an alkoxycarbonyl group having 2 to 20 carbon atoms, an aryloxycarbonyl group having 7 to 20 carbon atoms, a cyano group, a carbamoyl group, a halocarbonyl 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, a substituted or unsubstituted aromatic group having 6 to 60 ring atoms, a substituted or unsubstituted heteroaromatic group having 5 to 60 ring atoms, a substituted or unsubstituted aryloxy group having 5 to 60 ring atoms, a substituted or unsubstituted heteroaryloxy group having 5 to 60 ring atoms, or a combination of these groups.

[0091] It is understood that when X1 is a linking site, X1 is C; when Y1 is a linking site, Y1 is selected from N.

[0092] In some specific examples, R8, R9, R 10 、R 11 Each occurrence is independently selected from: -H, -D, a straight-chain alkyl group having 1 to 10 carbon atoms, a branched-chain alkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted aromatic group having 6 to 14 ring atoms, a substituted or unsubstituted heteroaromatic group having 6 to 14 ring atoms, or a combination of these groups.

[0093] The definition of the substituents is as described above.

[0094] In some specific examples, each occurrence of R8 is independently selected from: -H, -D, a straight-chain alkyl group having 1 to 4 carbon atoms, a branched-chain alkyl group having 3 to 4 carbon atoms, an aromatic group having 6 to 14 ring atoms, a heteroaromatic group having 6 to 14 ring atoms, an aromatic group having 6 to 14 ring atoms substituted with a straight-chain alkyl group having 1 to 4 carbon atoms or a branched-chain alkyl group having 3 to 4 carbon atoms, or a heteroaromatic group having 6 to 14 ring atoms substituted with a straight-chain alkyl group having 1 to 4 carbon atoms or a branched-chain alkyl group having 3 to 4 carbon atoms.

[0095] In some embodiments, L1 and L2 are independently selected from a single bond or any of the following groups:

[0096]

[0097] In some embodiments, L1 and L2 are each independently selected from a single bond or a phenyl group.

[0098] In some embodiments, the is selected from

[0099] As an example, the organic compound may be selected from, but not limited to, any one of the following structures:

[0100]

[0101]

[0102]

[0103]

[0104]

[0105]

[0106] In some embodiments, the organic compound of the present application can be used as an organic functional material in the functional layer of an organic electronic device, particularly in the functional layer of an OLED device. The organic functional material can be, but not limited to, 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, or an organic dye.

[0107] In some embodiments, the organic compound of the present application is used as a light-emitting material in the light-emitting layer of an organic electronic device. In some preferred embodiments, the organic compound of the present application is used as a host material in the light-emitting layer of an organic electronic device.

[0108] The present application also relates to a mixture comprising at least one of the above-described organic compounds and at least one other organic functional material. The other organic functional material can be, but not limited to, a hole injection material, a hole transport material, an electron transport material, an electron injection material, an electron blocking material, a hole blocking material, a light-emitting material, a host material, a guest material, and an organic dye known in the art for use in organic electronic devices.

[0109] In some embodiments, the other organic functional material is selected from guest materials. Further, the other organic functional material is selected from blue light guest materials. Further, the blue light guest is as shown in the following general formula (3).

[0110] This application also relates to a composition comprising at least one of the organic compounds or mixtures as described above, and at least one organic solvent.

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

[0112] The aromatic or heteroaromatic-based solvent may be selected from, but not limited to, at least one of p-diisopropylbenzene, pentylbenzene, tetralin, cyclohexylbenzene, chloronaphthalene, 1,4-dimethylnaphthalene, 3-isopropylbiphenyl, p-methylcumene, dipentylbenzene, tripentylbenzene, amyltoluene, o-diethylbenzene, m-diethylbenzene, p-diethylbenzene, 1,2,3,4-tetramethylbenzene, 1,2,3,5-tetramethylbenzene, 1,2,4,5-tetramethylbenzene, butylbenzene, dodecylbenzene, dihexylbenzene, dibutylbenzene, p-diisopropylbenzene, cyclohexylbenzene, benzyl butylbenzene, dimethylnaphthalene, 3-isopropylbiphenyl, p-methylcumene, 1-methylnaphthalene, 1,2,4-trichlorobenzene, 4,4-difluorodiphenylmethane, 1,2-dimethoxy-4-(1-propenyl)benzene, diphenylmethane, 2-phenylpyridine, 3-phenylpyridine, N-methyldiphenylamine, 4-isopropylbiphenyl, α,α-dichlorodiphenylmethane, 4-(3-phenylpropyl)pyridine, benzyl benzoate, 1,1-bis(3,4-dimethylphenyl)ethane, 2-isopropylnaphthalene, quinoline, isoquinoline, methyl 2-furoate and ethyl 2-furoate.

[0113] The ester-based solvent may be selected from, but not limited to, alkyl octanoates, alkyl sebacates, alkyl stearates, alkyl benzoates, alkyl phenylacetates, alkyl cinnamates, alkyl oxalates, alkyl maleates, alkanolactones, alkyl oleates, etc. At least one of octyl octanoate, diethyl sebacate, diallyl phthalate and isononyl isononanoate is particularly preferred.

[0114] The aromatic ketone-based solvent may be selected from, but not limited to, at least one of 1-tetralone, 2-tetralone, 2-(phenyl epoxy)tetralone, 6-(methoxy)tetralone, acetophenone, propiophenone, benzophenone, and their derivatives such as 4-methylacetophenone, 3-methylacetophenone, 2-methylacetophenone, 4-methylpropiophenone, 3-methylpropiophenone and 2-methylpropiophenone.

[0115] The aromatic ether-based solvent may be selected from, but 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-ethylbenzyl 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.

[0116] The aliphatic ketone-based solvent may be selected from, but not limited to, at least one of 2-nonanone, 3-nonanone, 5-nonanone, 2-decanone, 2,5-hexanedione, 2,6,8-trimethyl-4-nonanone, fenchone, phorone, isophorone, di-n-pentyl ketone, etc.; or aliphatic ethers, 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.

[0117] It can be understood that the organic solvent may be used alone or as a mixed solvent of two or more organic solvents.

[0118] In some embodiments, the composition of the present application comprises at least one organic compound or mixture as described above, and at least one organic solvent, and may further comprise another organic solvent.

[0119] The another organic solvent may be selected from, but not limited to, at least one of 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), tetralin, decalin, and indene.

[0120] In some preferred embodiments, the organic solvent suitable for the present application is a solvent with a Hansen solubility parameter in the following range:

[0121] 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;

[0122] 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;

[0123] δh (hydrogen bond force) is in the range of 0.9 - 14.2 MPa1 / 2, especially in the range of 2.0 - 6.0 MPa1 / 2.

[0124] In some embodiments, for the composition according to the present application, the organic solvent is selected considering its boiling point. In at least some embodiments, the boiling point of the organic solvent ≥ 150 °C; preferably ≥ 180 °C; more preferably ≥ 200 °C; still more preferably ≥ 250 °C; most preferably ≥ 300 °C. Boiling points within these ranges are beneficial for preventing nozzle clogging of the inkjet print head.

[0125] It can be understood that the organic solvent can evaporate from the composition system to form a thin film containing the organic compound of the present application.

[0126] In some embodiments, the composition is a solution. In still some other embodiments, the composition is a suspension. The solution or suspension may further include additives for adjusting viscosity, adjusting film-forming properties, improving adhesion, etc. The additives may be selected from but not limited to at least one of surface active compounds, lubricants, wetting agents, dispersants, water repellents, and adhesives.

[0127] In the composition, the content of the organic compound or mixture is 0.01 - 10 wt%, preferably 0.1 - 8 wt%, more preferably 0.2 - 5 wt%, still more preferably 0.25 - 3 wt%.

[0128] The present application also relates to the use of the composition as a coating or printing ink in the preparation of organic electronic devices. In some embodiments, the composition is used to prepare organic electronic devices by a preparation method of printing or coating. The preparation method of printing or coating may be but not limited to inkjet printing, gravure printing, spraying, letterpress printing, screen printing, dip coating, spin coating, knife coating, roller printing, reverse roller printing, lithographic printing, flexographic printing, rotary printing, spraying, brush coating, pad printing, slot die coating, etc. Preferred are gravure printing, spraying, and inkjet printing.

[0129] The present application also provides an application of the above-mentioned organic compound, mixture or composition in an organic electronic device. The technical solution is as follows:

[0130] An organic electronic device, comprising the above-mentioned organic compound or mixture, or prepared from the composition.

[0131] Further, an organic electronic device includes a first electrode, a second electrode, and one or more organic functional layers located between the first electrode and the second electrode. The organic functional layer contains the organic compound, mixture, or composition prepared from the above-mentioned composition.

[0132] The organic functional layer is selected from a hole injection layer (HIL), a hole transport layer (HTL), a light-emitting layer (EML), an electron blocking layer (EBL), an electron injection layer (EIL), an electron transport layer (ETL), and a hole blocking layer (HBL).

[0133] The organic electronic device can be, but is not limited to, an organic light-emitting diode (OLED device), an organic photovoltaic cell (OPV), an organic light-emitting electrochemical cell (OLEEC), an organic field-effect transistor (OFET), an organic light-emitting field-effect transistor, an organic laser, an organic spintronic device, an organic sensor, and an organic plasmon emitting diode, etc. The organic electronic device is preferably an OLED device. Further, in the embodiments of the present application, the organic compound is preferably used in the light-emitting layer of the OLED device.

[0134] In some embodiments, at least a light-emitting layer is included in one or more organic functional layers of the organic electronic device. The material of the light-emitting layer includes a host material and a guest material. The host material includes the organic compound as described above, and the guest material includes a pyrene-based organic compound.

[0135] The present invention further relates to an organic electronic device, which includes: a cathode, an anode, and one or more organic functional layers located between the cathode and the anode. The organic functional layer at least includes a light-emitting layer. The material of the light-emitting layer includes a host material and a guest material. The host material includes the organic compound of formula (1), and the guest material includes the pyrene-based organic compound of formula (3):

[0136] The structure of formula (3) is:

[0137]

[0138] Wherein:

[0139] s is selected from any integer from 0 to 8;

[0140] Ar2, Ar3, Ar4, and Ar5 are each independently selected from a substituted or unsubstituted aromatic group containing 6 to 60 ring atoms, a substituted or unsubstituted heteroaromatic group containing 6 to 60 ring atoms, or a combination of these groups;

[0141] R 12Each occurrence is independently selected from -D, a straight-chain alkyl group having 1 to 20 carbon atoms, a straight-chain alkoxy group having 1 to 20 carbon atoms, a straight-chain thioalkoxy group having 1 to 20 carbon atoms, a branched-chain alkyl group having 3 to 20 carbon atoms, a branched-chain alkoxy group having 3 to 20 carbon atoms, a branched-chain thioalkoxy group having 3 to 20 carbon atoms, a cyclic alkyl group having 3 to 20 carbon atoms, a cyclic alkoxy group having 3 to 20 carbon atoms, a cyclic thioalkoxy group having 3 to 20 carbon atoms, a silyl group, a keto group having 1 to 20 carbon atoms, an alkoxycarbonyl group having 2 to 20 carbon atoms, an aryloxycarbonyl group having 7 to 20 carbon atoms, 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, a substituted or unsubstituted aromatic group having 6 to 60 ring atoms, a substituted or unsubstituted heteroaromatic group having 5 to 60 ring atoms, a substituted or unsubstituted aryloxy group having 5 to 60 ring atoms, a substituted or unsubstituted heteroaryloxy group having 5 to 60 ring atoms, or a combination of these groups.

[0142] The further description of the organic compound represented by the formula (1) is as described above.

[0143] In some embodiments, Ar2, Ar3, Ar4, and Ar5 are each independently selected from a substituted or unsubstituted aromatic group having 6 to 14 ring atoms, a substituted or unsubstituted heteroaromatic group having 6 to 14 ring atoms, or a combination of these groups.

[0144] In some embodiments, Ar2, Ar3, Ar4, and Ar5 are each independently selected from the structures represented by any of the following:

[0145]

[0146] Wherein:

[0147] Each occurrence of V is independently selected from CR 13 or N;

[0148] W is selected from NR 14 , CR 15 R 16 , SiR 15 R 16 , O, S, S=O or SO2;

[0149] R 13 、R 14 、R 15 、R 16Each occurrence is independently selected from -H, -D, a straight-chain alkyl group having 1 to 20 C atoms, a straight-chain alkoxy group having 1 to 20 C atoms, a straight-chain thioalkoxy group having 1 to 20 C atoms, a branched-chain alkyl group having 3 to 20 C atoms, a branched-chain alkoxy group having 3 to 20 C atoms, a branched-chain thioalkoxy group having 3 to 20 C atoms, a cyclic alkyl group having 3 to 20 C atoms, a cyclic alkoxy group having 3 to 20 C atoms, a cyclic thioalkoxy group having 3 to 20 C atoms, a silyl group, a ketone group having 1 to 20 C atoms, an alkoxycarbonyl group having 2 to 20 C atoms, an aryloxycarbonyl group having 7 to 20 C atoms, a cyano group, a carbamoyl group, a halocarbonyl 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, a substituted or unsubstituted aromatic group having 6 to 60 ring atoms, a substituted or unsubstituted heteroaromatic group having 5 to 60 ring atoms, a substituted or unsubstituted aryloxy group having 5 to 60 ring atoms, a substituted or unsubstituted heteroaryloxy group having 5 to 60 ring atoms, or a combination of these groups.

[0150] Furthermore, in some embodiments, R 13 , R 14 , R 15 , R 16 Each occurrence is independently selected from -H, -D, a straight-chain alkyl group having 1 to 10 C atoms, a branched-chain alkyl group having 3 to 10 C atoms, a cyclic alkyl group having 3 to 10 C atoms, a substituted or unsubstituted aromatic group having 6 to 30 ring atoms, a substituted or unsubstituted heteroaromatic group having 5 to 30 ring atoms, or a combination of these groups.

[0151] Even further, in some embodiments, R 13 , R 14 , R 15 , R 16 Each occurrence is independently selected from -H, -D, a straight-chain alkyl group having 1 to 10 C atoms, a branched-chain alkyl group having 3 to 10 C atoms, a cyclic alkyl group, or a phenyl group.

[0152] In some embodiments, the general formula (3) of the pyrene-based organic compound is selected from the following structural general formulas:

[0153]

[0154] Wherein, R 13 Each occurrence is independently selected from -H, -D, a straight-chain alkyl group having 1 to 10 C atoms, or a branched-chain alkyl group having 3 to 10 C atoms, a cyclic alkyl group, or a phenyl group.

[0155] Further, in some embodiments, the general formula (3) of the pyrene-based organic compound is selected from the following general formulas:

[0156]

[0157] wherein R 13 each occurrence is independently selected from -H, -D, a straight-chain alkyl group having 1 to 10 C atoms, or a branched-chain alkyl group, a cyclic alkyl group or a phenyl group having 3 to 10 C atoms; W is as described above.

[0158] As an example, the organic compound may be selected from, but not limited to, any one of the following structures:

[0159]

[0160]

[0161] It can be understood that some conventional functional layers that are helpful for improving the device performance and are commonly used in organic electronic devices may be added to the organic electronic device, such as an electron injection layer, an electron blocking layer, a hole blocking layer, a light extraction layer, etc.

[0162] In one embodiment, the organic electronic device includes a cathode, an anode, a hole transport layer, a light-emitting layer, and an electron transport layer.

[0163] In one embodiment, the organic electronic device includes a cathode, an anode, a hole transport layer, a hole injection layer, a light-emitting layer, and an electron transport layer.

[0164] In one embodiment, the organic electronic device includes a cathode, an anode, a hole transport layer, a hole injection layer, a light-emitting layer, an electron blocking layer, and an electron transport layer.

[0165] Materials suitable for use in these functional layers are described in detail above and in WO2010135519A1, US20090134784A1, and WO2011110277A1, and the entire contents of these 3 patent documents are hereby incorporated herein by reference.

[0166] In some embodiments, the organic electronic device further includes a substrate. The substrate may be located on a side of the anode away from the light-emitting layer. The substrate may be opaque or transparent. It can be understood that when the substrate is transparent, the organic electronic device is a transparent device. The substrate may also be rigid or flexible. For example, the material of the substrate may be plastic, metal, semiconductor wafer or glass. Preferably, the substrate has a smooth surface, and a substrate without surface defects is a particularly ideal choice. In a preferred embodiment, the substrate is a flexible substrate. The material of the flexible substrate may be a polymer film or plastic. The glass transition temperature Tg of the flexible substrate is above 150 °C, preferably above 200 °C, more preferably above 250 °C, and most preferably above 300 °C. As an example, the material of the flexible substrate may be polyethylene terephthalate (PET) or polyethylene glycol (2,6-naphthalene) (PEN).

[0167] The material of the anode is an anode material known in the art for use in organic electronic devices, such as a conductive metal, a conductive metal oxide, or a conductive polymer. In some embodiments, the absolute value of the difference between the work function of the material 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 serving as a hole injection layer, a hole transport layer, or an electron blocking layer is less than 0.5 eV, preferably less than 0.3 eV, and most preferably less than 0.2 eV. As an example, the material of the anode may be selected from, but not limited to, at least one of Al, Cu, Au, Ag, Mg, Fe, Co, Ni, Mn, Pd, Pt, ITO, and aluminum-doped zinc oxide (AZO). Other suitable anode materials are known, and those of ordinary skill in the art can easily select and use them. The anode material can be deposited using any suitable technique, such as a suitable physical vapor deposition method, including radio frequency magnetron sputtering, vacuum thermal evaporation, electron beam (e-beam), etc. In certain embodiments, the anode is pattern-structured. Patterned ITO conductive substrates are commercially available and can be used to fabricate the devices according to the present invention.

[0168] The material of the cathode is a cathode material known in the art for use in organic electronic devices, such as a conductive metal or a conductive metal oxide. In some embodiments, the absolute value of the difference between the work function of the material of the cathode and the LUMO energy level or the conduction band energy level of the lumophore in the light-emitting layer or the n-type semiconductor material serving as the electron injection layer or the electron transport layer or the hole blocking layer is less than 0.5 eV, preferably less than 0.3 eV, and most preferably less than 0.2 eV. In principle, all materials that can be used as the cathode of an OLED may be used as the cathode material of the device of the present application. By way of example, the material of the cathode may be selected from, but not limited to, at least one of Al, Au, Ag, Ca, Ba, Mg, LiF / Al, MgAg alloy, BaF2 / Al, Cu, Fe, Co, Ni, Mn, Pd, Pt, and ITO. The cathode material may 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.

[0169] The material of the hole transport layer is a hole transport layer material known in the art. For example, it may be selected from, but not limited to, at least one of poly[bis(4-phenyl)(2,4,6-trimethylphenyl)amine] (PTXX), 2,2',7,7'-tetra[N,N-bis(4-methoxyphenyl)amino]-9,9'-spirobifluorene (spiro-omeTXD), 4,4'-cyclohexylbis[N,N-bis(4-methylphenyl)aniline] (TXPC), N,N′-bis(1-naphthyl)-N,N′-diphenyl-1,1′-biphenyl-4,4′-diamine (NPB), 4,4'-bis(N-carbazolyl)-1,1'-biphenyl (CBP), poly[(9,9-dioctylfluorene-2,7-diyl)-co-(4,4'-(N-(butylphenyl))diphenylamine)] (TFB), poly(9-vinylcarbazole) (PVK), poly(triphenylamine) (Poly-TPD), poly(3,4-ethylenedioxythiophene)-poly(styrenesulfonic acid) (PEDOT:PSS), and 4,4',4”-tris(carbazol-9-yl)triphenylamine (TCTX).

[0170] The material of the electron transport layer is a material known in the art for use in the electron transport layer. For example, it may be selected from, but not limited to, at least one of ET and Liq, PBD (2-(4-biphenylyl)-5-phenyloxadiazole), aluminum 8-hydroxyquinolate (Xlq3), and graphene.

[0171] Among them, the chemical structural formulas of ET and Liq are as follows:

[0172]

[0173] The material of the hole injection layer is a material known in the art for hole injection layers. For example, it can be selected from but not limited to at least one of 2,3,6,7,10,11 - hexacyano - 1,4,5,8,9,12 - hexaazatriphenylene (HXT - CN), PEDOT (polyethylenedioxythiophene), PEDOT:PSS, and its derivative doped with s - MoO3 (PEDOT:PSS:s - MoO3).

[0174] In at least one preferred embodiment, the organic electronic device is an OLED device. More preferably, the organic electronic device is a solution - type OLED.

[0175] The emission wavelength of the organic electronic device is between 300 nm and 1000 nm, preferably between 350 nm and 900 nm, and more preferably between 400 nm and 800 nm.

[0176] This application also relates to an electronic device comprising the organic electronic device. The electronic device can be but not limited to a display device, a lighting device, a light source, and a sensor, etc.

[0177] The following will specifically illustrate this application through specific examples. The following examples are only partial examples of this application and do not limit this application.

[0178] Example 1

[0179] The synthesis route of Compound 1 in this example is as follows:

[0180]

[0181] Synthesis of Intermediate 1 - 1:

[0182] 40 mL of N - methylpyrrolidone was added to a 250 - mL round - bottom flask containing 2 - fluoro - 4 - chloroacetophenone (10 g, 58 mmol), 2 - bromophenol (20 g, 116 mmol), and CsF (18 g, 116 mmol). The mixture was heated at 140 °C for 24 hours to obtain a reaction solution. Water was added to the reaction solution, and it was extracted with ethyl acetate, dried using the desiccant MgSO4, filtered, and concentrated in vacuo. The organic phase was subjected to column chromatography (the eluent was petroleum ether PE:ethyl acetate EA = 49:1) to obtain a colorless oil, namely Intermediate 1 - 1. Among them, the yield of Intermediate 1 - 1 was 61%, and MS(ASAP)=324.0.

[0183] Synthesis of Intermediate 1 - 2:

[0184] In a 250 mL two-necked flask, add intermediate 1-1 (10 g, 31 mmol), Pd2(dba)3 (0.7 g, 0.77 mmol), 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (0.89 g, 1.5 mmol) and Cs2CO3 (30 g, 93 mmol), and add 100 mL of toluene. React at 100 °C for 40 minutes to obtain a reaction solution. After cooling the reaction solution to room temperature, add 1 mol / L HCl (10 mL) to the reaction solution, extract with EA, dry with the desiccant MgSO4, filter, and concentrate under vacuum. Column chromatography of the organic phase (eluent: PE:EA = 49:1) gives a colorless oil, which is intermediate 1-2. Among them, the yield of intermediate 1-2 is 34%, and MS(ASAP) = 244.0.

[0185] Synthesis of intermediate 1-3:

[0186] Add intermediate 1-2 (5 g, 20 mmol) to a 100 mL two-necked flask, add 30 mL of dichloromethane solution until completely dissolved. Place the reaction solution in an ice bath. Weigh bromine (3.3 g, 20 mmol) and dissolve it in 20 mL of dichloromethane solution, and then slowly add it dropwise to the dichloromethane solution of intermediate 1-2. After slowly rising to room temperature, react for 12 hours to obtain a reaction solution. Slowly pour the reaction solution into an aqueous solution of sodium thiosulfate, extract with DCM (dichloromethane), collect the organic layer, wash with water, and perform column chromatography (eluent: PE) to obtain a white solid, which is intermediate 1-3. Among them, the yield of intermediate 1-3 is 80%, and MS(ASAP) = 321.9.

[0187] Synthesis of intermediate 1-4:

[0188] Add 1,2-dihydroxybenzene (10 g, 91 mmol) and triethylamine (18 g, 182 mmol) to a 250 mL two-necked flask, and then add 100 mL of dimethylformamide until all the solids are dissolved. Place the reaction system in an ice bath. Weigh intermediate 1-3 (22 g, 68 mmol) and place it in a constant pressure dropping funnel, dissolve it with 50 mL of DMF, slowly add it dropwise, and after slowly rising to room temperature, react for 12 hours to obtain a reaction solution. Slowly pour the reaction solution into an aqueous solution of sodium bicarbonate, extract with ethyl acetate, collect the organic layer, wash with water, and perform column chromatography (eluent: PE:DCM = 3:1) to obtain a white solid, which is intermediate 1-4. Among them, the yield of intermediate 1-4 is 65%, and MS(ASAP) = 352.1.

[0189] Synthesis of intermediate 1-5:

[0190] Weigh the intermediate 1-4 (5 g, 14.2 mmol) and place it in a 100-ml two-necked flask. Add 20 ml of SOCl2 and heat to 40 °C for reaction for 12 hours to obtain a reaction solution. Slowly pour the reaction solution into an aqueous sodium bicarbonate solution, extract with ethyl acetate, collect the organic layer, wash with water, and perform column chromatography (the eluent is PE:DCM = 10:1) to obtain a white solid, which is intermediate 1-5. Among them, the yield of intermediate 1-5 is 42%, and MS(ASAP) = 334.0.

[0191] Synthesis of intermediate 1-6:

[0192] Add intermediate 1-5 (5 g, 15 mmol), bis(pinacolato)diboron (4.6 g, 18 mmol), potassium acetate (7.4 g, 75 mmol), and dichloro[1,1'-bis(diphenylphosphino)ferrocene]palladium(II) (0.74 g, 1.0 mmol) to a 250-mL three-necked flask. Add 100 ml of 1,4-dioxane, displace nitrogen, and react at 100 °C for 12 h. Rotavapor to dryness, wash with water, and perform column chromatography (the eluent is PE:DCM = 3:1) to obtain a colorless oil, which is intermediate 1-6. Among them, the yield of intermediate 1-6 is 83%, and MS(ASAP) = 426.2.

[0193] Synthesis of compound 1:

[0194] Dissolve intermediate 1-6 (6 g, 14 mmol) and 9-bromo-10-(1-naphthyl)anthracene (5.4 g, 14 mmol) in a mixed solvent of 1,4-dioxane and water (100 ml / 10 ml), and add Pd(PPh3)4 (0.81 g, 0.7 mmol) and potassium carbonate (5.5 g, 40 mmol). Stir at 100 °C for 12 h under a nitrogen atmosphere. After cooling, rotary evaporate to remove most of the solvent, then extract and wash and separate the liquid. Perform column chromatography on the organic phase (the eluent is PE), and recrystallize to obtain compound 1. The yield of compound 1 is 63%, and MS(ASAP) = 602.2.

[0195] Example 2

[0196] The synthetic route of compound 2 in this example is as follows:

[0197]

[0198] Synthesis of intermediate 2-1:

[0199] In a 250 mL round-bottom flask containing 2-fluoro-5-chloroacetophenone (10 g, 58 mmol), 2-bromophenol (20 g, 116 mmol) and CsF (18 g, 116 mmol), NMP (40 mL) was added. The mixture was heated at 140 °C for 24 hours to obtain a reaction solution. Water was added to the reaction solution, and it was extracted with ethyl acetate, dried over anhydrous MgSO4, filtered, and concentrated in vacuo. The organic phase was purified by column chromatography (eluent: PE:EA = 49:1) to obtain a colorless oil, namely intermediate 2-1. The yield of intermediate 2-1 was 58%, and MS (ASAP) = 324.0.

[0200] Synthesis of intermediate 2-2:

[0201] In a 250 mL two-necked flask, intermediate 2-1 (5 g, 15.5 mmol), Pd2(dba)3 (0.35 g, 0.39 mmol), XantPhos (0.45 g, 0.75 mmol) and Cs2CO3 (30 g, 93 mmol) were added, and 100 mL of toluene was added. The reaction was carried out at 100 °C for 40 minutes to obtain a reaction solution. After the reaction solution was cooled to room temperature, 1 M HCl (10 mL) was added, and it was extracted with EA, dried over anhydrous MgSO4, filtered, and concentrated in vacuo. The organic phase was purified by column chromatography (eluent: PE:EA = 49:1) to obtain a colorless oil, namely intermediate 2-2. The yield of intermediate 2-2 was 28%, and MS (ASAP) = 244.0.

[0202] Synthesis of intermediate 2-3:

[0203] In a 100 mL two-necked flask, intermediate 2-2 (8 g, 33 mmol) was added, and 30 mL of dichloromethane solution was added until completely dissolved. The flask was placed in an ice bath. Bromine (5.2 g, 33 mmol) was weighed and dissolved in 20 mL of dichloromethane solution, and then slowly added dropwise to the dichloromethane solution of intermediate 2-2. After slowly warming to room temperature, the reaction was carried out for 12 hours to obtain a reaction solution. The reaction solution was slowly poured into an aqueous solution of sodium thiosulfate, extracted with DCM, the organic layer was collected, washed with water, and purified by column chromatography (eluent: PE) to obtain a white solid, namely intermediate 2-3. The yield of intermediate 2-3 was 82%, and MS (ASAP) = 321.9.

[0204] Synthesis of intermediate 2-4:

[0205] In a 250 ml two-necked flask, add 1,2-dihydroxybenzene (5.0 g, 46 mmol) and triethylamine (9.0 g, 91 mmol). Add 100 ml of DMF until all the solids are dissolved. Place the reaction system in an ice bath. Weigh the intermediate 2-3 (11 g, 34 mmol) and place it in a constant pressure dropping funnel. Dissolve it with 50 ml of DMF and slowly add it dropwise. After slowly rising to room temperature, react for 12 hours to obtain a reaction solution. Slowly pour the reaction solution into an aqueous sodium bicarbonate solution, extract with ethyl acetate, collect the organic layer, wash with water, and perform column chromatography (the eluent is PE:DCM = 3:1) to obtain a white solid, which is the intermediate 2-4. Among them, the yield of the intermediate 2-4 is 61%, and MS(ASAP) = 352.1.

[0206] Synthesis of intermediate 2-5:

[0207] Weigh the intermediate 2-4 (8 g, 23 mmol) and place it in a 100 ml two-necked flask. Add 20 ml of SOCl2 and heat to 40 °C for reaction for 12 hours to obtain a reaction solution. Slowly pour the reaction solution into an aqueous sodium bicarbonate solution, extract with ethyl acetate, collect the organic layer, wash with water, and perform column chromatography (the eluent is PE:DCM = 10:1) to obtain a white solid, which is the intermediate 2-5. Among them, the yield of the intermediate 2-5 is 37%, and MS(ASAP) = 334.0.

[0208] Synthesis of intermediate 2-6:

[0209] Weigh the intermediate 2-5 (4 g, 12 mmol), (Bpin)2 (3.6 g, 14 mmol), AcOK (5.9 g, 60 mmol), and Pd(dppf)Cl2 (0.88 g, 1.2 mmol) into a 250 mL three-necked flask. Add 100 ml of 1,4-dioxane, displace nitrogen, react at 100 °C for 12 h, spin-dry, wash with water, and perform column chromatography (the eluent is PE:DCM = 3:1) to obtain a colorless oily substance, which is the intermediate 2-6. Among them, the yield of the intermediate 2-6 is 88%, and MS(ASAP) = 426.2.

[0210] Synthesis of compound 2:

[0211] Intermediate 2-6 (8 g, 19 mmol) and 9-bromo-10-(1-phenyl)anthracene (6.3 g, 19 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (100 ml / 10 ml), and Pd(PPh3)4 (1.2 g, 1.0 mmol) and potassium carbonate (8.3 g, 60 mmol) were added. Under a nitrogen atmosphere, the mixture was stirred at 100 °C for 12 h. After cooling, most of the solvent was removed by rotary evaporation, and then the mixture was extracted, washed with water, and separated by liquid-liquid extraction. The organic phase was purified by column chromatography (eluent: PE) and recrystallized to obtain Compound 2. The yield of Compound 2 was 67%, and MS (ASAP) = 552.2.

[0212] Example 3

[0213] The synthetic route of Compound 3 in this example is as follows:

[0214]

[0215] Synthesis of Intermediate 3-1:

[0216] 9-Bromo-10-(1-phenyl)anthracene (3.3 g, 10 mmol) and 4-bromo-1-phenylboronic acid (2.0 g, 10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (100 / 10 ml), and Pd(PPh3)4 (1.15 g, 1 mmol) and potassium carbonate (4.1 g, 30 mmol) were added. Under a nitrogen atmosphere, the mixture was stirred at 100 °C for 12 h. After cooling, most of the solvent was removed by rotary evaporation, and then the mixture was extracted, washed with water, and separated by liquid-liquid extraction. The organic phase was purified by column chromatography and recrystallized to obtain Intermediate 3-1. The yield of Intermediate 3-1 was 89%, and MS (ASAP) = 408.1.

[0217] Synthesis of Compound 3:

[0218] Intermediate 3-1 (6 g, 15 mmol) and Intermediate 1-6 (7.5 g, 18 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (100 / 10 ml), and Pd(PPh3)4 (0.87 g, 0.75 mmol) and potassium carbonate (6.2 g, 45 mmol) were added. Under a nitrogen atmosphere, the mixture was stirred at 100 °C for 12 h. After cooling, most of the solvent was removed by rotary evaporation, and then the mixture was extracted, washed with water, and separated by liquid-liquid extraction. The organic phase was purified by column chromatography and recrystallized to obtain Compound 3. The yield of Compound 3 was 64%, and MS (ASAP) = 628.2.

[0219] Example 4

[0220] The synthetic route of Compound 4 in this example is as follows:

[0221]

[0222] Synthesis of Intermediate 4-1:

[0223] Dissolve 9-bromo-10-(1-phenyl)anthracene (3.3 g, 10 mmol) and 4-bromo-2,3,5,6-tetramethylphenylboronic acid (3.1 g, 12 mmol) in a mixed solvent of 1,4-dioxane and water (100 / 10 ml), add Pd(PPh3)4 (1.15 g, 1 mmol) and potassium carbonate (4.1 g, 30 mmol), stir at 100 °C for 12 h under a nitrogen atmosphere. After cooling, most of the solvent is removed by rotary evaporation, then extracted, washed with water and separated by liquid-liquid extraction. The organic phase is purified by column chromatography and recrystallization to obtain Intermediate 4-1. Among them, the yield of Intermediate 4-1 is 42%, and MS(ASAP) = 464.1.

[0224] Synthesis of Compound 4:

[0225] Dissolve Intermediate 4-1 (7.6 g, 16 mmol) and Intermediate 2-6 (8.4 g, 20 mmol) in a mixed solvent of 1,4-dioxane and water (100 / 10 ml), add Pd(PPh3)4 (0.92 g, 0.8 mmol) and potassium carbonate (6.6 g, 48 mmol), stir at 100 °C for 12 h under a nitrogen atmosphere. After cooling, most of the solvent is removed by rotary evaporation, then extracted, washed with water and separated by liquid-liquid extraction. The organic phase is purified by column chromatography and recrystallization to obtain Compound 4. Among them, the yield of Compound 4 is 69%, and MS(ASAP) = 684.3.

[0226] Example 5

[0227] The synthetic route of the compound in this example is as follows:

[0228]

[0229] Synthesis of Intermediate 5-1:

[0230] Dissolve 9,10-dibromoanthracene (10 g, 30 mmol) and dibenzo[b,d]furan-2-boronic acid (6.3 g, 30 mmol) in a mixed solvent of 1,4-dioxane and water (100 / 10 ml), add Pd(PPh3)4 (1.7 g, 1.5 mmol) and potassium carbonate (20.7 g, 150 mmol), stir at 100 °C for 12 h under a nitrogen atmosphere. After cooling, most of the solvent is removed by rotary evaporation, then extracted, washed with water and separated by liquid-liquid extraction. The organic phase is purified by column chromatography and recrystallization to obtain Intermediate 5-1. Among them, the yield of Intermediate 5-1 is 95%, and MS(ASAP) = 422.0.

[0231] Synthesis of Compound 5:

[0232] Intermediate 5-1 (4.2 g, 10 mmol), intermediate 2-6 (4.3 g, 10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (100 / 10 ml), and Pd(PPh3)4 (1.15 g, 1 mmol) and potassium carbonate (4.1 g, 30 mmol) were added. Under a nitrogen atmosphere, the mixture was stirred at 100 °C for 12 h. After cooling, most of the solvent was removed by rotary evaporation, and then extraction and washing with water were carried out for liquid separation. The organic phase was subjected to column chromatography and recrystallization to obtain compound 5. Among them, the yield of compound 5 was 71%, and MS(ASAP) = 642.2.

[0233] Example 6

[0234] The synthetic route of compound 6 in this example is as follows:

[0235]

[0236] Synthesis of intermediate 6-1:

[0237] 9,10-Dibromoanthracene (3.4 g, 10 mmol) and deuterated phenylboronic acid (1.5 g, 12 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (100 / 10 ml), and Pd(PPh3)4 (1.15 g, 1 mmol) and potassium carbonate (4.1 g, 30 mmol) were added. Under a nitrogen atmosphere, the mixture was stirred at 100 °C for 12 h. After cooling, most of the solvent was removed by rotary evaporation, and then extraction and washing with water were carried out for liquid separation. The organic phase was subjected to column chromatography and recrystallization to obtain intermediate 6-1. Among them, the yield of intermediate 6-1 was 78%, and MS(ASAP) = 337.1.

[0238] Synthesis of compound 6:

[0239] Intermediate 6-1 (3.4 g, 10 mmol) and intermediate 1-6 (4.3 g, 10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (100 / 10 ml), and Pd(PPh3)4 (1.15 g, 1 mmol) and potassium carbonate (4.1 g, 30 mmol) were added. Under a nitrogen atmosphere, the mixture was stirred at 100 °C for 12 h. After cooling, most of the solvent was removed by rotary evaporation, and then extraction and washing with water were carried out for liquid separation. The organic phase was subjected to column chromatography and recrystallization to obtain compound 6. Among them, the yield of compound 6 was 79%, and MS(ASAP) = 557.2.

[0240] Example 7

[0241] The synthetic route of compound 7 in this example is as follows:

[0242]

[0243] Synthesis of intermediate 7-1:

[0244] Dissolve 9,10-dibromoanthracene (6.8 g, 20 mmol) and deuterated 1-naphthylboronic acid (3.6 g, 20 mmol) in a mixed solvent of 1,4-dioxane and water (100 / 10 ml), add Pd(PPh3)4 (1.15 g, 1 mmol) and potassium carbonate (8.3 g, 60 mmol), stir at 100 °C for 12 h under a nitrogen atmosphere. After cooling, most of the solvent was removed by rotary evaporation, and then extraction and washing with water were carried out for liquid separation. The organic phase was subjected to column chromatography and recrystallization to obtain intermediate 7-1. Among them, the yield of intermediate 7-1 was 73%, and MS(ASAP) = 389.1.

[0245] Synthesis of organic compound 7:

[0246] Dissolve intermediate 7-1 (3.9 g, 10 mmol) and intermediate 1-6 (4.3 g, 10 mmol) in a mixed solvent of 1,4-dioxane and water (100 / 10 ml), add Pd(PPh3)4 (1.15 g, 1 mmol) and potassium carbonate (4.1 g, 30 mmol), stir at 100 °C for 12 h under a nitrogen atmosphere. After cooling, most of the solvent was removed by rotary evaporation, and then extraction and washing with water were carried out for liquid separation. The organic phase was subjected to column chromatography and recrystallization to obtain compound 7. Among them, the yield of compound 7 was 66%, and MS(ASAP) = 609.2.

[0247] Example 8

[0248] The synthetic route of compound 8 in this example is as follows:

[0249]

[0250] Synthesis of intermediate 8-1:

[0251] Dissolve 9-bromo-10-(2-naphthyl)anthracene (3.8 g, 10 mmol) and 2-bromo-pyridine-5-boronic acid (2.0 g, 10 mmol) in a mixed solvent of 1,4-dioxane and water (100 / 10 ml), add Pd(PPh3)4 (1.15 g, 1 mmol) and potassium carbonate (4.1 g, 30 mmol), stir at 100 °C for 12 h under a nitrogen atmosphere. After cooling, most of the solvent was removed by rotary evaporation, and then extraction and washing with water were carried out for liquid separation. The organic phase was subjected to column chromatography and recrystallization to obtain intermediate 8-1. Among them, the yield of intermediate 8-1 was 86%, and MS(ASAP) = 459.1.

[0252] Synthesis of compound 8:

[0253] The intermediate 8-1 (4.6 g, 10 mmol) and the intermediate 1-6 (4.3 g, 10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (100 / 10 ml), and Pd(PPh3)4 (1.15 g, 1 mmol) and potassium carbonate (4.1 g, 30 mmol) were added. Under a nitrogen atmosphere, the mixture was stirred at 100 °C for 12 h. After cooling, most of the solvent was removed by rotary evaporation, and then the mixture was extracted, washed with water, and separated by liquid-liquid extraction. The organic phase was purified by column chromatography and recrystallization to obtain compound 8. Among them, the yield of compound 8 was 49%, and MS(ASAP) = 679.2.

[0254] Example 9

[0255] The synthetic route of compound 9 in this example is as follows:

[0256]

[0257] Synthesis of intermediate 9-1:

[0258] 9,10-Dibromoanthracene (3.4 g, 10 mmol) and 3,5-diphenylphenylboronic acid (2.8 g, 10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (100 / 10 ml), and Pd(PPh3)4 (1.15 g, 1 mmol) and potassium carbonate (8.3 g, 60 mmol) were added. Under a nitrogen atmosphere, the mixture was stirred at 100 °C for 12 h. After cooling, most of the solvent was removed by rotary evaporation, and then the mixture was extracted, washed with water, and separated by liquid-liquid extraction. The organic phase was purified by column chromatography and recrystallization to obtain intermediate 9-1. Among them, the yield of intermediate 9-1 was 95%, and MS(ASAP) = 484.1.

[0259] Synthesis of compound 9:

[0260] The intermediate 9-1 (4.9 g, 10 mmol) and the intermediate 1-6 (4.3 g, 10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (100 / 10 ml), and Pd(PPh3)4 (1.15 g, 1 mmol) and potassium carbonate (4.1 g, 30 mmol) were added. Under a nitrogen atmosphere, the mixture was stirred at 100 °C for 12 h. After cooling, most of the solvent was removed by rotary evaporation, and then the mixture was extracted, washed with water, and separated by liquid-liquid extraction. The organic phase was purified by column chromatography and recrystallization to obtain compound 9. Among them, the yield of compound 9 was 51%, and MS(ASAP) = 704.2.

[0261] Example 10

[0262] The synthetic route of the compound in this example is as follows:

[0263]

[0264] Synthesis of intermediate 10-1:

[0265] Dissolve 9,10-dibromoanthracene (3.4 g, 10 mmol) and fluoranthene-3-boronic acid (2.5 g, 10 mmol) in a mixed solvent of 1,4-dioxane and water (100 / 10 ml), add Pd(PPh3)4 (1.15 g, 1 mmol) and potassium carbonate (8.3 g, 60 mmol), stir at 100 °C for 12 h under a nitrogen atmosphere. After cooling, most of the solvent is removed by rotary evaporation, and then extraction, washing, and liquid separation are carried out. The organic phase is subjected to column chromatography and recrystallization to obtain intermediate 10-1. Among them, the yield of intermediate 10-1 is 84%, and MS(ASAP)=456.1.

[0266] Synthesis of compound 10:

[0267] Dissolve intermediate 10-1 (4.6 g, 10 mmol) and intermediate 2-6 (4.3 g, 10 mmol) in a mixed solvent of 1,4-dioxane and water (100 / 10 ml), add Pd(PPh3)4 (1.15 g, 1 mmol) and potassium carbonate (4.1 g, 30 mmol), stir at 100 °C for 12 h under a nitrogen atmosphere. After cooling, most of the solvent is removed by rotary evaporation, and then extraction, washing, and liquid separation are carried out. The organic phase is subjected to column chromatography and recrystallization to obtain compound 10. Among them, the yield of compound 10 is 53%, and MS(ASAP)=676.2.

[0268] Example 11

[0269] The synthetic route of compound 11 in this example is as follows:

[0270]

[0271] Synthesis of intermediate 11-1:

[0272] Dissolve 9,10-dibromoanthracene (3.4 g, 10 mmol) and 1-pyreneboronic acid (2.5 g, 10 mmol) in a mixed solvent of 1,4-dioxane and water (100 / 10 ml), add Pd(PPh3)4 (1.15 g, 1 mmol) and potassium carbonate (8.3 g, 60 mmol), stir at 100 °C for 12 h under a nitrogen atmosphere. After cooling, most of the solvent is removed by rotary evaporation, and then extraction, washing, and liquid separation are carried out. The organic phase is subjected to column chromatography and recrystallization to obtain intermediate 11-1. Among them, the yield of intermediate 11-1 is 73%, and MS(ASAP)=456.1.

[0273] Synthesis of compound 11:

[0274] Intermediate 11-1 (6 g, 13 mmol) and Intermediate 1-6 (6.7 g, 16 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (100 / 10 ml), and Pd(PPh3)4 (1.5 g, 1.3 mmol) and potassium carbonate (5.4 g, 39 mmol) were added. Under a nitrogen atmosphere, the mixture was stirred at 100 °C for 12 h. After cooling, most of the solvent was removed by rotary evaporation, and then the mixture was extracted, washed with water, and separated by liquid-liquid extraction. The organic phase was purified by column chromatography and recrystallization to obtain Compound 11. The yield of Compound 11 was 55%, and MS (ASAP) = 676.2.

[0275] Example 12

[0276] The synthetic route of Compound 12 in this example is as follows:

[0277]

[0278] Synthesis of Intermediate 12-1:

[0279] 9,10-Dibromoanthracene (6.8 g, 20 mmol) and 3-pyridineboronic acid (2.5 g, 20 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (100 / 10 ml), and Pd(PPh3)4 (1.15 g, 1 mmol) and potassium carbonate (14 g, 100 mmol) were added. Under a nitrogen atmosphere, the mixture was stirred at 100 °C for 12 h. After cooling, most of the solvent was removed by rotary evaporation, and then the mixture was extracted, washed with water, and separated by liquid-liquid extraction. The organic phase was purified by column chromatography and recrystallization to obtain Intermediate 12-1. The yield of Intermediate 12-1 was 68%, and MS (ASAP) = 333.0.

[0280] Synthesis of Organic Compound 12:

[0281] Intermediate 12-1 (8 g, 24 mmol) and Intermediate 1-6 (12 g, 29 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (100 / 10 ml), and Pd(PPh3)4 (1.4 g, 1.2 mmol) and potassium carbonate (9.9 g, 72 mmol) were added. Under a nitrogen atmosphere, the mixture was stirred at 100 °C for 12 h. After cooling, most of the solvent was removed by rotary evaporation, and then the mixture was extracted, washed with water, and separated by liquid-liquid extraction. The organic phase was purified by column chromatography and recrystallization to obtain Compound 12. The yield of Compound 12 was 59%, and MS (ASAP) = 553.2.

[0282] Example 13

[0283] The synthetic route of Compound 13 in this example is as follows:

[0284]

[0285] Synthesis of Intermediate 13-1:

[0286] Dissolve 4-bromophenylboronic acid (2.0 g, 10 mmol) and deuterated iodobenzene (2.1 g, 10 mmol) in a mixed solvent of 1,4-dioxane and water (100 / 10 ml), add Pd(PPh3)4 (1.15 g, 1 mmol) and potassium carbonate (14 g, 100 mmol), stir at 100 °C for 12 h under a nitrogen atmosphere. After cooling, most of the solvent is removed by rotary evaporation, then extracted, washed with water and separated by liquid separation. The organic phase is subjected to column chromatography and recrystallization to obtain Intermediate 13-1. Among them, the yield of Intermediate 13-1 is 63%, and MS(ASAP) = 237.0.

[0287] Synthesis of Intermediate 13-2:

[0288] Weigh Intermediate 13-1 (10 g, 42 mmol), (Bpin)2 (13 g, 51 mmol), AcOK (21 g, 210 mmol), and Pd(dppf)Cl2 (0.49 g, 0.42 mmol) into a 250 mL three-necked flask, add 100 ml of 1,4-dioxane, displace nitrogen, react at 100 °C for 12 h, spin dry, wash with water, and perform column chromatography (eluent: PE:DCM = 3:1) to obtain a colorless oil, which is Intermediate 13-2. Among them, the yield of Intermediate 13-2 is 83%, and MS(ASAP) = 285.2.

[0289] Synthesis of Intermediate 13-3:

[0290] Dissolve Intermediate 13-2 (10 g, 35 mmol) and 9,10-dibromoanthracene (12 g, 35 mmol) in a mixed solvent of 1,4-dioxane and water (100 / 10 ml), add Pd(PPh3)4 (0.4 g, 0.35 mmol) and potassium carbonate (14 g, 100 mmol), stir at 100 °C for 12 h under a nitrogen atmosphere. After cooling, most of the solvent is removed by rotary evaporation, then extracted, washed with water and separated by liquid separation. The organic phase is subjected to column chromatography and recrystallization to obtain Intermediate 13-3. Among them, the yield of Intermediate 13-3 is 59%, and MS(ASAP) = 413.1.

[0291] Synthesis of Compound 13:

[0292] Intermediate 13-3 (8 g, 19.4 mmol) and Intermediate 1-6 (9.9 g, 23.2 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (100 / 10 ml), and Pd(PPh3)4 (0.23 g, 0.2 mmol) and potassium carbonate (14 g, 100 mmol) were added. Under a nitrogen atmosphere, the mixture was stirred at 100 °C for 12 h. After cooling, most of the solvent was removed by rotary evaporation, and then the mixture was extracted, washed with water, and separated by liquid-liquid extraction. The organic phase was purified by column chromatography and recrystallization to obtain Compound 13. The yield of the compound was 53%, and MS (ASAP) = 633.2.

[0293] Example 14

[0294] The synthetic route of Compound 14 in this example is as follows:

[0295]

[0296] Synthesis of Intermediate 14-1:

[0297] 9-Bromo-10-(1-naphthyl)anthracene (3.8 g, 10 mmol) and 4-bromo-1-naphthylboronic acid (2.5 g, 10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (100 / 10 ml), and Pd(PPh3)4 (1.15 g, 1 mmol) and potassium carbonate (4.1 g, 30 mmol) were added. Under a nitrogen atmosphere, the mixture was stirred at 100 °C for 12 h. After cooling, most of the solvent was removed by rotary evaporation, and then the mixture was extracted, washed with water, and separated by liquid-liquid extraction. The organic phase was purified by column chromatography and recrystallization to obtain Intermediate 14-1. The yield of Intermediate 14-1 was 73%, and MS (ASAP) = 508.1.

[0298] Synthesis of Organic Compound 14:

[0299] Intermediate 14-1 (5.1 g, 10 mmol) and Intermediate 1-6 (4.3 g, 10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (100 / 10 ml), and Pd(PPh3)4 (1.15 g, 1 mmol) and potassium carbonate (4.1 g, 30 mmol) were added. Under a nitrogen atmosphere, the mixture was stirred at 100 °C for 12 h. After cooling, most of the solvent was removed by rotary evaporation, and then the mixture was extracted, washed with water, and separated by liquid-liquid extraction. The organic phase was purified by column chromatography and recrystallization to obtain Compound 14. The yield of Compound 14 was 43%, and MS (ASAP) = 728.2.

[0300] Example 15

[0301] The synthetic route of Compound 15 in this example is as follows:

[0302]

[0303] Synthesis of Intermediate 15-1:

[0304] Dissolve 9,10-dibromoanthracene (6.8 g, 20 mmol) and 9,9-dimethylfluorene-2-boronic acid (4.8 g, 20 mmol) in a mixed solvent of 1,4-dioxane and water (100 / 10 ml), add Pd(PPh3)4 (2.3 g, 2 mmol) and potassium carbonate (14 g, 100 mmol), stir at 100 °C for 12 h under a nitrogen atmosphere. After cooling, most of the solvent is removed by rotary evaporation, then extracted, washed with water and separated by liquid separation. The organic phase is purified by column chromatography and recrystallization to obtain Intermediate 15-1. Among them, the yield of Intermediate 15-1 is 65%, and MS(ASAP) = 448.1.

[0305] Synthesis of Compound 15:

[0306] Dissolve Intermediate 15-1 (10 g, 22 mmol) and Intermediate 1-6 (12 g, 27 mmol) in a mixed solvent of 1,4-dioxane and water (100 / 10 ml), add Pd(PPh3)4 (1.4 g, 1.2 mmol) and potassium carbonate (9.9 g, 72 mmol), stir at 100 °C for 12 h under a nitrogen atmosphere. After cooling, most of the solvent is removed by rotary evaporation, then extracted, washed with water and separated by liquid separation. The organic phase is purified by column chromatography and recrystallization to obtain Compound 15. Among them, the yield of Compound 15 is 51%, and MS(ASAP) = 668.2.

[0307] Comparative Example

[0308] The organic compound in this comparative example is BH-Ref, and its chemical structural formula is as follows:

[0309]

[0310] The preparation process of the OLED-1 device using the above compounds is described in detail below through specific examples. The structure of the OLED device is: ITO / HIL / HTL / EML / ETL / cathode. The schematic diagram of the OLED device is as Figure 1 shown, where 101 is the substrate, 102 is the anode, 103 is the hole injection layer (HIL), 104 is the hole transport layer (HTL), 105 is the light-emitting layer, 106 is the electron transport layer (ETL), and 107 is the cathode.

[0311] a. Cleaning of the ITO (indium tin oxide) conductive glass substrate: Clean it with various solvents (such as one or several of chloroform, acetone or isopropanol), and then perform ultraviolet ozone treatment;

[0312] b. HIL (Hole Injection Layer, 40 nm): 60 nm of PEDOT (Poly(3,4-ethylenedioxythiophene), Clevios AI4083) was spin-coated as the HIL in a cleanroom and treated on a hot plate at 180 °C for 10 minutes; TM AI4083) was spin-coated as the HIL in a cleanroom and treated on a hot plate at 180 °C for 10 minutes;

[0313] c. HTL (Hole Transport Layer, 20 nm): 20 nm of PVK (Sigma Aldrich, average Mn 25,000 - 50,000) was spin-coated in a nitrogen glove box. The solution used was PVK added to toluene solvent with a solution concentration of 5 mg / ml, and then treated on a hot plate at 180 °C for 60 minutes;

[0314] d. EML (Emissive Layer, 40 nm): The EML was spin-coated in a nitrogen glove box. The solution used was a solution of methyl benzoate with different host - guest materials (the weight ratio of host - guest is 95:5), with a solution concentration of 15 mg / ml. Then it was treated on a hot plate at 140 °C for 10 minutes. The host used was Compound 1 of Example 1, and the guest material was selected from BD - 1.

[0315] e. Electron Transport Layer and Cathode: The heat - treated substrate was transferred to a vacuum chamber. Then ET and Liq were placed in different evaporation units and co - deposited at a ratio of 50 wt% each in a high vacuum (1×10 - 6 mbar) to form a 20 - nm electron transport layer on the emissive layer. Subsequently, an Al cathode with a thickness of 100 nm was deposited.

[0316] f. Encapsulation: The device was encapsulated with ultraviolet - curable resin in a nitrogen glove box.

[0317] The preparation schemes of OLED - 2 - OLED - 15 and OLED - Ref are the same as that of OLED - 1, except that Compound 1 in Example OLED - 1 was replaced with the corresponding compound of the host material in Table 1.

[0318] The current - voltage (J - V) characteristics of each OLED device were characterized by a characterization device, and the color efficiency (CE@1 knits) and lifetime (LT90@1 knits) were recorded simultaneously. The results are shown in Table 1 below.

[0319] Table 1:

[0320] Device embodiment Host material CE@1knits[cd / A] LT90@1knits[h] OLED-1 Compound 1 5.1 329 OLED-2 Compound 2 5.4 366 OLED-3 Compound 3 5.8 385 OLED-4 Compound 4 5.9 373 OLED-5 Compound 5 6.4 413 OLED-6 Compound 6 6.6 422 OLED-7 Compound 7 6.1 409 OLED-8 Compound 8 5.5 362 OLED-9 Compound 9 5.2 323 OLED-10 Compound 10 5.7 358 OLED-11 Compound 11 5.3 377 OLED-12 Compound 12 5.8 369 OLED-13 Compound 13 6.2 418 OLED-14 Compound 14 5.6 322 OLED-15 Compound 15 5.3 318 OLED-Ref BH-ref 4.9 289

[0321] As can be seen from Table 1:

[0322] Compared with the blue OELD device prepared by using the organic compound of the comparative example as the host material in the light-emitting layer, the OELD device prepared by using the organic compounds 1-15 of Examples 1-15 as the host material in the light-emitting layer has better color efficiency and longer lifespan.

[0323] In addition, the luminous efficiency of the blue OELD devices prepared by using the organic compounds 1-15 of Examples 1-15 as the host material in the light-emitting layer is in the range of 5-7 cd / A, having more excellent luminous efficiency, and the effects of devices OLED-5, OLED-6, OLED-7 and OLED-13 are better than those of other devices.

[0324] For device OLED-5, dibenzofuran is introduced into the molecule of the organic compound, which enhances the hole transport ability of the device, enabling the device to reach a more ideal electrical balance state, thereby improving the device performance.

[0325] For devices OLED-6, OLED-7 and OLED-13, some of the hydrogen atoms in the molecule of the organic compound are deuterated, which increases the molecular structure stability of the organic compound, thereby improving the overall device performance.

[0326] The heterocyclic-fused-ring-containing anthracene organic compound has fluorescence emission at the blue light wavelength, can be used as a host material in the light-emitting layer of an organic electronic device, and the organic electronic device prepared by using the organic compound has good high luminous efficiency and long device lifespan.

[0327] The above has introduced in detail the organic compounds, mixtures, compositions and organic electronic devices provided by the embodiments of the present application. Specific examples are used herein to elaborate on the principles and implementation manners of the present application. The description of the above embodiments is only used to help understand the method and its core idea of the present application; at the same time, for those skilled in the art, according to the idea of the present application, there will be changes in the specific implementation manners and application scopes. In summary, the content of this specification should not be construed as a limitation to the present application.

Claims

1. An organic compound, characterized in that, It has a structure shown in the general formula (1): Wherein: Ar1 is selected from the structures shown by any of the following: Each occurrence of X is independently selected from CR4 or N; Y is selected from CR6R7, O, S; Each occurrence of R4 is independently selected from -H, -D or phenyl; R6 and R7 are selected from methyl; L1 and L2 are each independently selected from a single bond or the structures shown by any of the following: Each occurrence of X1 is independently selected from CR8 or N; Each occurrence of R8 is independently selected from -H or methyl; R1, R2 and R3 are selected from -H; m1 is 8; m2 is 4; m3 is 4.

2. The organic compound according to claim 1, characterized in that, The structure of the organic compound is selected from the structures shown by any of the general formulas (2-1)-(2-6):

3. The organic compound according to claim 1, wherein Ar1 is selected from the groups shown by any of the following:

4. The organic compound according to claim 1, characterized in that, L1 and L2 are each independently selected from a single bond or the groups shown by any of the following:

5. The organic compound according to claim 1, characterized in that, The organic compound is selected from any one of the following structures:

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

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

8. An organic electronic device includes at least one functional layer, characterized in that: The at least one functional layer includes a light-emitting layer, the light-emitting layer includes a host material and a guest material, the host material contains the organic compound according to any one of claims 1-5, or the mixture according to claim 6, or the light-emitting layer is prepared from the composition according to claim 7.

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