Organic compounds and mixtures, compositions and organic electronic devices thereof

Abstract

This application discloses an organic compound having the following structure: Ar1 is selected from another source. This application also discloses a mixture, a composition, and an organic electronic device. This application provides anthracene derivatives containing heterocyclic fused rings that can be used as host materials in the light-emitting layer of organic electronic devices. These organic compounds exhibit fluorescence emission at blue light wavelengths and can be used as luminescent materials in blue organic light-emitting electronic devices, resulting in higher device luminous efficiency and longer device lifetime.

Description

Technical Field

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

[0002] Organic semiconductor materials offer diverse synthesis options, relatively low manufacturing costs, and excellent optical and electrical properties. Organic light-emitting diodes (OLEDs) possess advantages such as wide viewing angles, fast response times, low operating voltages, and thin panel thicknesses in optoelectronic devices (e.g., flat panel displays and lighting), thus demonstrating broad development potential.

[0003] Organic electroluminescence (OEC) refers to the phenomenon of converting electrical energy into light energy using organic materials. OEC devices typically have a positive electrode, a negative electrode, and an organic layer between them. To improve the efficiency and lifetime of OEC devices, the organic layer has a multi-layered structure, with each layer containing a different organic material. Specifically, it can include a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, and an electron injection layer. In such OEC devices, applying a voltage between the two electrodes injects holes into the organic layer from the positive electrode and electrons from the negative electrode. When the injected holes and electrons meet, excitons are formed, and these excitons emit light when they transition back to the ground state. Such OEC devices possess characteristics such as self-illumination, high brightness, high efficiency, low driving voltage, wide viewing angle, high contrast, and high responsiveness.

[0004] To improve the luminous efficiency of organic light-emitting diodes (OLEDs), various fluorescent and phosphorescent luminescent material systems have been developed. However, the development of excellent blue light-emitting materials, whether fluorescent or phosphorescent, remains a significant challenge. Generally speaking, OLEDs using blue fluorescent materials exhibit higher reliability. However, most current blue fluorescent materials have excessively broad emission spectra and poor color purity, which are detrimental to high-end displays. Furthermore, the synthesis of these materials is complex, hindering large-scale mass production. Additionally, the stability of OLEDs using these blue fluorescent materials needs further improvement. Therefore, developing blue fluorescent materials with narrow-band emission spectra and good stability is beneficial for obtaining longer-life, more efficient blue light-emitting devices, and for improving the color gamut, thereby enhancing display performance.

[0005] Current blue organic light-emitting diodes (OLEDs) employ a host-guest doped structure for their emissive layers, with the blue host material mostly being anthracene-based fused-ring derivatives. However, the poor stability of these emissive layer materials leads to short device lifespans. Furthermore, these materials struggle to achieve deep blue light emission, failing to meet the demands of full-color displays.

[0006] Therefore, further improvements to the materials are still needed to enhance the performance of organic electroluminescent devices. Summary of the Invention

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

[0008] This application is achieved through the following technical solution:

[0009] An organic compound having a structure as shown in general formula (1):

[0010]

[0011] in:

[0012] Ar1 is selected from the structure shown in general formula (2):

[0013] Ar2 is selected from substituted or unsubstituted aromatic groups containing 6 to 60 ring atoms, or substituted or unsubstituted heteroaromatic groups containing 5 to 60 ring atoms, or combinations of these groups;

[0014] G is selected from straight-chain alkyl groups having 1 to 20 carbon atoms, branched alkyl groups having 3 to 20 carbon atoms, cyclic alkyl groups having 3 to 20 carbon atoms, substituted or unsubstituted aromatic groups having 6 to 60 ring atoms, substituted or unsubstituted heteroaromatic groups having 5 to 60 ring atoms, or combinations of these groups.

[0015] L1 and L2 are independently selected from single-bonded, substituted or unsubstituted aromatic groups containing 6 to 60 ring atoms, or substituted or unsubstituted heteroaromatic groups containing 5 to 60 ring atoms.

[0016] R1, R2, and R3, each appearing independently, are selected from -D, or straight-chain alkyl groups having 1 to 20 carbon atoms, straight-chain alkoxy groups having 1 to 20 carbon atoms, or straight-chain thioalkoxy groups having 1 to 20 carbon atoms, or branched alkyl groups having 3 to 20 carbon atoms, or branched alkoxy groups having 3 to 20 carbon atoms, or branched thioalkoxy groups having 3 to 20 carbon atoms, or cyclic alkyl groups having 3 to 20 carbon atoms, or cyclic alkoxy groups having 3 to 20 carbon atoms, or cyclic thioalkoxy groups having 3 to 20 carbon atoms, or silyl groups, or ketone groups having 1 to 20 carbon atoms, or groups having 2 to 20 carbon atoms. An alkoxy carbonyl group having 7 to 20 carbon atoms, or an aryloxy carbonyl group having 7 to 20 carbon atoms, a cyano group, a carbamoyl group, a haloformyl group, a formyl group, an isocyano group, an isocyanate group, a thiocyanate group, or an isothiocyanate group, a hydroxyl group, a nitro group, a substituted or unsubstituted amino group, -CF3, -Cl, -Br, -F, -I, or a substituted or unsubstituted aromatic group having 6 to 60 ring atoms, or a substituted or unsubstituted heteroaromatic group having 5 to 60 ring atoms, or a substituted or unsubstituted aryloxy group having 5 to 60 ring atoms, or a substituted or unsubstituted heteroaromatic group having 5 to 60 ring atoms, or a combination of these groups;

[0017] m1 is 0, 1, 2, 3, 4, 5, 6, 7 or 8;

[0018] m2 can be 0, 1, 2, or 3;

[0019] m3 can be 0, 1, 2 or 3.

[0020] Accordingly, this application also provides a mixture comprising the above-mentioned organic compound and at least one organic functional material, wherein the organic functional material is selected from hole injection materials, hole transport materials, electron transport materials, electron injection materials, electron blocking materials, hole blocking materials, luminescent materials, host materials, guest materials or organic dyes.

[0021] Accordingly, this application also provides a composition comprising the above-mentioned organic compound or mixture thereof, and at least one organic solvent.

[0022] Accordingly, this application also provides an organic electronic device comprising at least one functional layer, wherein the functional layer contains the above-mentioned organic compound or mixture thereof, or the functional layer is prepared from the above-mentioned composition.

[0023] Compared with the prior art, the organic compounds of this application have the following beneficial effects:

[0024] The anthracene derivatives containing heterocyclic fused rings described in this application can be used as host materials in the light-emitting layer of organic electronic devices. These organic compounds exhibit fluorescence emission at blue light wavelengths, thus they can be used in blue organic light-emitting electronic devices, exhibiting high device luminous efficiency and long device lifetime. Attached Figure Description

[0025] To more clearly illustrate the technical solutions in the embodiments of this application, the accompanying drawings used in the description of the embodiments will be briefly introduced below. Obviously, the accompanying drawings described below are only some embodiments of this application. For those skilled in the art, other drawings can be obtained based on these drawings without creative effort.

[0026] Figure 1 This is a schematic diagram of the OLED device shown in Embodiment 1 of this application;

[0027] In this design, 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. Detailed Implementation

[0028] The technical solutions of the embodiments of this application will be clearly and completely described below with reference to the accompanying drawings. Obviously, the described embodiments are only some embodiments of this application, and not all embodiments. Based on the embodiments of this application, all other embodiments obtained by those skilled in the art without creative effort are within the scope of protection of this application. Furthermore, it should be understood that the specific embodiments described herein are only for illustration and explanation of this application and are not intended to limit this application.

[0029] In the description of this application, the term "comprising" means "including but not limited to," and the term "a plurality of" means "two or more." Various embodiments of this application may exist in the form of a range; it should be understood that the description in the form of a range is merely for convenience and brevity and should not be construed as a rigid limitation on the scope of this application; therefore, it should be considered that the range description has specifically disclosed all possible sub-ranges and single numerical 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 the range, such as 1, 2, 3, 4, 5, and 6, regardless of the range. Furthermore, whenever a numerical range is indicated herein, it means including any referenced number (fraction or integer) within the indicated range.

[0030] Unless otherwise defined, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this application belongs. The terminology used herein is for the purpose of describing particular embodiments only and is not intended to be limiting of the application. The term "and / or" as used herein includes any and all combinations of one or more of the associated listed items.

[0031] In this application, the terms "composition," "printing ink," and "ink" have the same meaning and are interchangeable.

[0032] In this application, aromatic groups, aromatic families, and aromatic ring systems have the same meaning and can be used interchangeably.

[0033] In this application, heteroaromatic groups, heteroaromatic families, and heteroaromatic ring systems have the same meaning and can be used interchangeably.

[0034] In this application, "substitution" means that the hydrogen atom in the substituent is replaced by the substituent.

[0035] In this application, "substituted or unsubstituted" means that the defined group may or may not be substituted. When the defined group is substituted, it should be understood that the defined group can be substituted by one or more substituents R, wherein R is selected from, but not limited to, deuterium, cyano, isocyano, nitro, halogen, alkyl containing 1-20 C atoms, heterocyclic group containing 3-20 ring atoms, aromatic group containing 6-20 ring atoms, heteroaromatic group containing 5-20 ring atoms, -NR'R", silyl, carbonyl, alkoxycarbonyl, aryloxycarbonyl, carbamoyl, halocarbamoyl, formyl, isocyanate, thiocyanate, isothiocyanate, hydroxyl, and trifluoromethyl, and the above groups may also be further substituted by substituents acceptable in the art; it is understood that R' and R" in -NR'R" are independently selected from, but not limited to, H and deuterium. The group R is selected from, but is not limited to, deuterium, cyano, isocyano, nitro or halogen, alkyl containing 1-10 carbon atoms, heterocyclic group containing 3-20 ring atoms, aromatic group containing 6-20 ring atoms, and heteroaromatic group containing 5-20 ring atoms. Preferably, R is selected from, but is not limited to, deuterium, cyano, isocyano, nitro or halogen, alkyl containing 1-10 carbon atoms, heterocyclic group containing 3-10 ring atoms, aromatic group containing 6-20 ring atoms, heteroaromatic group containing 5-20 ring atoms, silyl, carbonyl, alkoxycarbonyl, aryloxycarbonyl, carbamoyl, haloformyl, formyl, isocyanate, thiocyanate, isothiocyanate, hydroxyl, and trifluoromethyl, and the above groups may be further substituted with substituents acceptable in the art.

[0036] In this application, "ring atom number" refers to the number of atoms in the ring itself of a structural compound (e.g., a monocyclic compound, a fused-ring compound, a cross-linked compound, a carbocyclic compound, or a heterocyclic compound) obtained by atomic bonding to form a ring. When the ring is substituted by a substituent, the atoms contained in the substituent are not included in the ring-forming atoms. The same applies to the "ring atom number" described below unless otherwise specified. For example, a benzene ring has 6 ring atoms, a naphthalene ring has 10 ring atoms, and a thiophene group has 5 ring atoms.

[0037] "Aryl or aromatic group" refers to an aromatic hydrocarbon group derived from an aromatic ring compound by removing one hydrogen atom. It can be a monocyclic aryl, a fused-ring aryl, or a polycyclic aryl, and in the case of a polycyclic ring, at least one of the rings is an aromatic ring system. For example, "substituted or unsubstituted aryl having 6 to 40 ring atoms" means an aryl containing 6 to 40 ring atoms, preferably a substituted or unsubstituted aryl having 6 to 30 ring atoms, more preferably a substituted or unsubstituted aryl having 6 to 18 ring atoms, and particularly preferably a substituted or unsubstituted aryl having 6 to 14 ring atoms, and optionally further substituted on the aryl group; suitable examples include, but are not limited to, phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthryl, fluoranyl, triphenylene, pyrene, perylene, tetraphenyl, fluorenyl, dinaphthylphenyl, acenaphthyl and their derivatives. It is understandable that multiple aryl groups can also be interrupted by short non-aromatic units (e.g., <10% non-H atoms, such as C, N or O atoms), specifically acenaphthene, fluorene, 9,9-diarylfluorene, triarylamine or diaryl ether systems should also be included in the definition of aryl.

[0038] "Heteroaryl or heteroaromatic group" refers to an aryl group in which at least one carbon atom is replaced by a non-carbon atom, which can be an N atom, O atom, S atom, etc. For example, "substituted or unsubstituted heteroaryl group having 5 to 40 ring atoms" refers to a heteroaryl group having 5 to 40 ring atoms, preferably a substituted or unsubstituted heteroaryl group having 6 to 30 ring atoms, more preferably a substituted or unsubstituted heteroaryl group having 6 to 18 ring atoms, and particularly preferably a substituted or unsubstituted heteroaryl group having 6 to 14 ring atoms. The heteroaryl group may optionally be further substituted, and suitable examples include, but are not limited to, thiophene, furanyl, pyrrole, diazolyl, triazolyl, imidazole, pyridyl, bipyridyl, pyrimidinyl, and triazolyl groups. Azinyl, acridineyl, pyridazinyl, pyrazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, phthalazinyl, pyridinylpyrimidinyl, pyridinylpyrazinyl, benzothiopheneyl, benzofuranyl, indolyl, pyrroloimidazolyl, pyrrolopyrrololyl, thienopyrrololyl, thienopyrrololyl, furanolololyl, furanolol, thienofuranyl, benzoisoxazolyl, benzoisothiazolyl, benzoimidazolyl, o-diazonaphthyl, phenanthridine, primidyl, quinazolinone, dibenzothiopheneyl, dibenzofuranyl, carbazoleyl and their derivatives.

[0039] In this application, "alkyl" can mean straight-chain, branched, and / or cyclic alkyl. The number of carbon atoms in an alkyl group can be 1 to 50, 1 to 30, 1 to 20, 1 to 10, or 1 to 6. Non-limiting examples of alkyl groups include methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, tert-butyl, isobutyl, 2-ethylbutyl, 3,3-dimethylbutyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, cyclopentyl, 1-methylpentyl, 3-methylpentyl, 2-ethylpentyl, 4-methyl-2-pentyl, n-hexyl, 1-methylhexyl, 2-ethylhexyl, 2-butylhexyl, cyclohexyl, adamantyl, etc.

[0040] In this application, "halogen" or "halogen group" refers to F, Cl, Br or I.

[0041] In this application, the term "alkoxy" refers to a group having an -O-alkyl group, i.e., an alkyl group as defined above that is attached to the parent nucleus via an oxygen atom. Suitable examples of phrases containing this term include, but are not limited to: methoxy (-O-CH3 or -OMe), ethoxy (-O-CH2CH3 or -OEt), and tert-butoxy (-OC(CH3)3 or -OtBu).

[0042] In this application, "*" indicates a connection site.

[0043] In this application, when the same group contains multiple substituents with the same symbol, the substituents can be the same as or different from each other, for example... The six R's on the benzene ring 1 They can be the same as or different from each other.

[0044] In this application, the single bond connecting the substituents extends through the corresponding ring, indicating that the substituent can be attached to any position on the ring, for example... R is attached to any substituted site on the benzene ring; such as express Can be with A fused ring can be formed at any position on the benzene ring.

[0045] The cyclic alkyl or cycloalkyl groups used in this application have the same meaning and are interchangeable.

[0046] The technical solution of this application is as follows:

[0047] An organic compound having a structure as shown in general formula (1):

[0048]

[0049] in:

[0050] Ar1 is selected from the structure shown in general formula (2):

[0051] Ar2 is selected from substituted or unsubstituted aromatic groups containing 6 to 60 ring atoms, or substituted or unsubstituted heteroaromatic groups containing 5 to 60 ring atoms, or combinations of these groups;

[0052] G is selected from straight-chain alkyl groups having 1 to 20 carbon atoms, branched alkyl groups having 3 to 20 carbon atoms, cyclic alkyl groups having 3 to 20 carbon atoms, substituted or unsubstituted aromatic groups having 6 to 60 ring atoms, substituted or unsubstituted heteroaromatic groups having 5 to 60 ring atoms, or combinations of these groups.

[0053] L1 and L2 are independently selected from single-bonded, substituted or unsubstituted aromatic groups containing 6 to 60 ring atoms, or substituted or unsubstituted heteroaromatic groups containing 5 to 60 ring atoms.

[0054] R1, R2, and R3, each appearing independently, are selected from -D, or straight-chain alkyl groups having 1 to 20 carbon atoms, straight-chain alkoxy groups having 1 to 20 carbon atoms, or straight-chain thioalkoxy groups having 1 to 20 carbon atoms, or branched alkyl groups having 3 to 20 carbon atoms, or branched alkoxy groups having 3 to 20 carbon atoms, or branched thioalkoxy groups having 3 to 20 carbon atoms, or cyclic alkyl groups having 3 to 20 carbon atoms, or cyclic alkoxy groups having 3 to 20 carbon atoms, or cyclic thioalkoxy groups having 3 to 20 carbon atoms, or silyl groups, or ketone groups having 1 to 20 carbon atoms, or groups having 2 to 20 carbon atoms. An alkoxy carbonyl group having 7 to 20 carbon atoms, or an aryloxy carbonyl group having 7 to 20 carbon atoms, a cyano group, a carbamoyl group, a haloformyl group, a formyl group, an isocyano group, an isocyanate group, a thiocyanate group, or an isothiocyanate group, a hydroxyl group, a nitro group, a substituted or unsubstituted amino group, -CF3, -Cl, -Br, -F, -I, or a substituted or unsubstituted aromatic group having 6 to 60 ring atoms, or a substituted or unsubstituted heteroaromatic group having 5 to 60 ring atoms, or a substituted or unsubstituted aryloxy group having 5 to 60 ring atoms, or a substituted or unsubstituted heteroaromatic group having 5 to 60 ring atoms, or a combination of these groups;

[0055] m1 is 0, 1, 2, 3, 4, 5, 6, 7 or 8;

[0056] m2 can be 0, 1, 2, or 3;

[0057] m3 can be 0, 1, 2 or 3.

[0058] In one embodiment, the organic compound is selected from the structure shown in general formula (3-1) or general formula (3-2):

[0059]

[0060] In some embodiments, R1, R2, and R3, each appearing independently, are selected from -D, or a straight-chain alkyl group having 1 to 10 carbon atoms, or a straight-chain alkoxy group having 1 to 10 carbon atoms, or a straight-chain thioalkoxy group having 1 to 10 carbon atoms, or a branched alkyl group having 3 to 10 carbon atoms, or a branched alkoxy group having 3 to 10 carbon atoms, or a branched thioalkoxy group having 3 to 10 carbon atoms, or a cyclic alkyl group having 3 to 20 carbon atoms, or a cyclic alkoxy group having 3 to 10 carbon atoms, or a cyclic thioalkoxy group having 3 to 10 carbon atoms, or a silyl group, or a group having 1 to 10 carbon atoms. The group may contain a ketone group, or an alkoxycarbonyl group having 2 to 10 carbon atoms, or an aryloxycarbonyl group having 7 to 10 carbon atoms, a cyano group, a carbamoyl group, a haloformyl group, a formyl group, an isocyano group, an isocyanate group, a thiocyanate group, or an isothiocyanate group, a hydroxyl group, a nitro group, an amino group, a CF3 group, a Cl group, a Br group, a F group, an I group, or a substituted or unsubstituted aromatic group having 6 to 30 ring atoms, or a substituted or unsubstituted heteroaromatic group having 6 to 30 ring atoms, or a substituted or unsubstituted aryloxy group having 6 to 30 ring atoms, or a substituted or unsubstituted heteroaromatic group having 6 to 30 ring atoms, or a combination of these groups.

[0061] In some embodiments, R1, R2, and R3 each appear independently selected from -D, a straight-chain alkyl group having 1 to 8 carbon atoms, a branched 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, an aromatic group having 6 to 10 substituted or unsubstituted ring atoms, a heteroaromatic group having 5 to 10 substituted or unsubstituted ring atoms, or a combination of these groups.

[0062] In some embodiments, R1, R2, and R3 each appear independently selected from -D, a straight-chain alkyl group having 1 to 4 carbon atoms, a branched alkyl group having 3 to 6 carbon atoms, a cyclic alkyl group having 3 to 6 carbon atoms, a silyl group, a cyano group, an isocyano group, a hydroxyl group, a nitro group, -CF3, -Cl, -Br, -F, an aromatic group having 6 to 10 substituted or unsubstituted cyclic atoms, a heteroaromatic group having 6 to 10 substituted or unsubstituted cyclic atoms, or a combination of these groups.

[0063] In some specific embodiments, R1, R2, and R3, each time appearing, are 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, anthracene, phenanthryl, triazine, pyridyl, pyrimidinyl, imidazolyl, furanyl, thiophene, benzofuranyl, benzothiophene, indolyl, carbazolyl, dibenzothiophene, dibenzofuranyl, phenyl-substituted carbazolyl, fluorenyl, or fluorenyl substituted with an alkyl group having 1-6 carbon atoms, or phenyl substituted with an alkyl group having 1-6 carbon atoms, or naphthyl substituted with an alkyl group having 1-6 carbon atoms, or phenyl substituted with one or more D atoms, or naphthyl substituted with one or more D atoms, or naphthyl substituted with phenyl.

[0064] In one embodiment, m2 is 0 or 1; each occurrence of R2 is independently selected from -D, methyl, isopropyl, tert-butyl, phenyl, biphenyl, naphthyl, phenyl-substituted carbazolyl, dibenzofuranyl, dibenzothiophene, fluorenyl substituted with one or more methyl groups, phenanthryl, pyrene, fluoranyl, pyridyl, pyrimidinyl, phenyl substituted with an alkyl group having 1-6 carbon atoms, or naphthyl substituted with an alkyl group having 1-6 carbon atoms, or phenyl substituted with one or more D groups, or naphthyl substituted with one or more D groups, or naphthyl substituted with phenyl groups.

[0065] In one embodiment, m3 is 0 or 1. Each occurrence of R3 is independently selected from -D, methyl, isopropyl, tert-butyl, phenyl, biphenyl, naphthyl, phenyl-substituted carbazolyl, dibenzofuranyl, dibenzothiophene, fluorenyl substituted with one or more methyl groups, phenanthrene, pyrene, fluoranyl, pyridyl, pyrimidinyl, phenyl substituted with an alkyl group having 1-6 carbon atoms, or naphthyl substituted with an alkyl group having 1-6 carbon atoms, or phenyl substituted with one or more D groups, or naphthyl substituted with one or more D groups, or naphthyl substituted with phenyl groups.

[0066] In some embodiments, Ar2 is selected from substituted or unsubstituted aromatic groups containing 6 to 30 ring atoms, or substituted or unsubstituted heteroaromatic groups containing 6 to 30 ring atoms.

[0067] In some embodiments, Ar2 is selected from substituted or unsubstituted aromatic groups containing 6 to 16 ring atoms, or substituted or unsubstituted heteroaromatic groups containing 6 to 16 ring atoms.

[0068] In some embodiments, the Ar2 is selected from any of the following structures:

[0069]

[0070] in:

[0071] Each time X appears, it is independently selected from CR5 or N;

[0072] Y is selected from NR6, CR7R8, SiR7R8, O, S, S=O or SO2;

[0073] R5, R6, R7, and R8, each appearing independently, are selected from -H, -D, or straight-chain alkyl groups having 1 to 20 carbon atoms, straight-chain alkoxy groups having 1 to 20 carbon atoms, or straight-chain thioalkoxy groups having 1 to 20 carbon atoms, or branched alkyl groups having 3 to 20 carbon atoms, or branched alkoxy groups having 3 to 20 carbon atoms, or branched thioalkoxy groups having 3 to 20 carbon atoms, or cyclic alkyl groups having 3 to 20 carbon atoms, or cyclic alkoxy groups having 3 to 20 carbon atoms, or cyclic thioalkoxy groups having 3 to 20 carbon atoms, or silyl groups, or ketone groups having 1 to 20 carbon atoms, or groups having 2 to 20 carbon atoms. An alkoxy carbonyl group having 7 to 20 carbon atoms, or an aryloxy carbonyl group having 7 to 20 carbon atoms, a cyano group, a carbamoyl group, a haloformyl group, a formyl group, an isocyano group, an isocyanate group, a thiocyanate group, or an isothiocyanate group, a hydroxyl group, a nitro group, an amino group, -CF3, -Cl, -Br, -F, -I, or a substituted or unsubstituted aromatic group having 6 to 60 ring atoms, or a substituted or unsubstituted heteroaromatic group having 5 to 60 ring atoms, or a substituted or unsubstituted aryloxy group having 5 to 60 ring atoms, or a substituted or unsubstituted heteroaromatic group having 5 to 60 ring atoms, or a combination of these groups; R7 and R8 may be cyclic or acyclic with each other.

[0074] Understandably, in this application, when X is a connection site, X is C; when Y is a connection site, Y is N.

[0075] In some specific embodiments, the structure of the organic compound is selected from any of the structures shown in general formulas (4-1)-(4-10):

[0076]

[0077]

[0078] In some specific examples, each time R5 appears, it is independently selected from: -H, -D, straight-chain alkyl with 1 to 10 carbon atoms, branched alkyl with 3 to 10 carbon atoms, cyclic alkyl with 3 to 10 carbon atoms, silyl, cyano, isocyano, nitro, -CF3, -Cl, -Br, -F, -I, substituted or unsubstituted aromatic groups with 6 to 20 ring atoms, substituted or unsubstituted heteroaromatic groups with 5 to 20 ring atoms, or combinations of these groups.

[0079] Furthermore, each occurrence of R5 is independently selected from: -H, -D, a straight-chain alkyl group having 1 to 8 carbon atoms, a branched alkyl group having 3 to 8 carbon atoms, a cyclic alkyl group having 3 to 8 carbon 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. The definition of the substituent is given in the preceding description and will not be repeated here. Preferably, the substituent is selected from -D, a straight-chain alkyl group having 1 to 4 carbon atoms, a branched alkyl group having 3 to 4 carbon atoms, or a phenyl group, or a pyridyl group.

[0080] In one embodiment, X in general formulas (4-1)-(4-10) is selected from CR5; each time R5 appears, it is independently selected from: -H, -D, straight-chain alkyl with 1 to 6 C atoms, branched alkyl with 3 to 6 C atoms, and cyclic alkyl with 3 to 6 C atoms.

[0081] In one embodiment, each occurrence of R6 is independently selected from: a straight-chain alkyl group having 1 to 10 carbon atoms, a branched alkyl group having 3 to 10 carbon atoms, a cyclic alkyl group having 3 to 10 carbon 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 R6 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. Alternatively, each occurrence of R6 is independently selected from: methyl, ethyl, isopropyl, tert-butyl, phenyl, pyridyl, pyrimidinyl, triazine, biphenyl, terphenyl, or naphthyl.

[0082] In some specific examples, each time R7 and R8 appear, they are independently selected from: -H, -D, a straight-chain alkyl group having 1 to 8 carbon atoms, a branched alkyl group having 3 to 8 carbon atoms, a cyclic alkyl group having 3 to 8 carbon 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; furthermore, each time R7 and R8 appear, they are independently selected from: -H, -D, methyl, ethyl, isopropyl, phenyl, pyridyl, pyrimidinyl, triazine, biphenyl, terphenyl, or naphthyl.

[0083] In a particular embodiment, Ar2 is selected from any of the following structures:

[0084]

[0085] Where: * indicates a connection site.

[0086] In one embodiment, G is selected from straight-chain alkyl groups having 1 to 10 C atoms, branched alkyl groups having 3 to 10 C atoms, cyclic alkyl groups having 3 to 10 C atoms, substituted or unsubstituted aromatic groups containing 6 to 30 cyclic atoms, substituted or unsubstituted heteroaromatic groups containing 6 to 30 cyclic atoms, or combinations of these groups.

[0087] In one embodiment, G is selected from substituted or unsubstituted aromatic groups containing 6 to 16 ring atoms, or substituted or unsubstituted heteroaromatic groups containing 6 to 16 ring atoms.

[0088] In one specific embodiment, G is selected from any of the following structures:

[0089]

[0090] in:

[0091] The meanings of X and Y are the same as described above.

[0092] Specifically, in general formula (3-1) or general formulas (4-1)-(4-5), G can be selected from the following groups:

[0093]

[0094] In general formula (3-2) or general formulas (4-6)-(4-10), G is selected from the following groups:

[0095]

[0096] Where: * indicates a connection site.

[0097] Preferably, in general formulas (A-1)-(A-7) and / or general formulas (B-1)-(B-4), each occurrence of X is independently selected from CR5 or N; each occurrence of R5 is independently selected from: -H, -D, a straight-chain alkyl group having 1 to 8 carbon atoms, a branched alkyl group having 3 to 8 carbon atoms, a cyclic alkyl group having 3 to 8 carbon 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. The substituents are defined as described above. Preferably, the substituents may be selected from -D, a straight-chain alkyl group having 1 to 4 carbon atoms, a branched alkyl group having 3 to 4 carbon atoms, or a phenyl group, or a pyridyl group.

[0098] In general formulas (A-1)-(A-7) and / or general formulas (B-1)-(B-4), R5 is selected independently each time it appears: -H, -D, a straight-chain alkyl group having 1 to 6 carbon atoms, a branched alkyl group having 3 to 6 carbon atoms, a cyclic alkyl group having 3 to 6 carbon atoms, or a phenyl group.

[0099] In one embodiment, L1 and L2 are independently selected from single bonds, or substituted or unsubstituted aromatic groups containing 6 to 20 ring atoms, or substituted or unsubstituted heteroaromatic groups containing 6 to 20 ring atoms; further, L1 and L2 are independently selected from single bonds, or substituted or unsubstituted aromatic groups containing 6 to 14 ring atoms, or substituted or unsubstituted heteroaromatic groups containing 6 to 14 ring atoms.

[0100] Furthermore, in some embodiments, L1 and L2 are each independently selected from a single bond or any of the structures shown below:

[0101]

[0102] in:

[0103] Each time X1 appears, it is independently selected from CR4 or N;

[0104] Each time R4 appears, it is independently selected from -H, -D, or a straight-chain alkyl group having 1 to 20 carbon atoms, a straight-chain alkoxy group having 1 to 20 carbon atoms, or a straight-chain thioalkoxy group having 1 to 20 carbon atoms, or a branched alkyl group having 3 to 20 carbon atoms, or a branched alkoxy group having 3 to 20 carbon atoms, or a branched thioalkoxy group having 3 to 20 carbon atoms, or a cyclic alkyl group having 3 to 20 carbon atoms, or a cyclic alkoxy group having 3 to 20 carbon atoms, or a cyclic thioalkoxy group having 3 to 20 carbon atoms, or a silyl group, or a ketone group having 1 to 20 carbon atoms, or a group having 2 to 20 carbon atoms. An alkoxycarbonyl group with 20 carbon atoms, or an aryloxycarbonyl group with 7 to 20 carbon atoms, a cyano group, a carbamoyl group, a haloformyl group, a formyl group, an isocyano group, an isocyanate group, a thiocyanate group, or an isothiocyanate group, a hydroxyl group, a nitro group, an amino group, -CF3, -Cl, -Br, -F, -I, or a substituted or unsubstituted aromatic group with 6 to 60 ring atoms, or a substituted or unsubstituted heteroaromatic group with 5 to 60 ring atoms, or a substituted or unsubstituted aryloxy group with 5 to 60 ring atoms, or a substituted or unsubstituted heteroaromatic group with 5 to 60 ring atoms, or a combination of these groups.

[0105] Understandably, in this application, when X1 is a connection site, X1 is C.

[0106] In some specific examples, each occurrence of R4 is independently selected from: -H, -D, a straight-chain alkyl group having 1 to 4 carbon atoms, a branched 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 substituted with a straight-chain alkyl group having 1 to 4 carbon atoms or a branched 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 alkyl group having 3 to 6 carbon atoms.

[0107] In some embodiments, L1 and L2 are each independently selected from a single bond or any of the following groups:

[0108]

[0109]

[0110] As an example, the organic compounds of this application may be selected from, but are not limited to, any of the following structures:

[0111]

[0112]

[0113]

[0114]

[0115]

[0116] In some embodiments, the organic compounds of this application can be used as organic functional materials in the functional layers of organic electronic devices, particularly OLED devices. The functional materials can be, but are not limited to, hole injection materials (HIM), hole transport materials (HTM), electron transport materials (ETM), electron injection materials (EIM), electron blocking materials (EBM), hole blocking materials (HBM), emitters, host materials, or organic dyes.

[0117] In some embodiments, the organic compounds of this application can be used as luminescent materials in the luminescent layer of organic electronic devices. In some preferred embodiments, the organic compounds of this application are used as host materials in the luminescent layer of organic electronic devices.

[0118] This application also relates to a mixture comprising at least one of the described organic compounds and at least one other organic functional material. The other organic functional material may be, but is not limited to, hole injection materials, hole transport materials, electron transport materials, electron injection materials, electron blocking materials, hole blocking materials, luminescent materials, host materials, guest materials, and organic dyes known in the art for use in organic electronic devices.

[0119] 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 can have the structure shown in the following general formula (5).

[0120] This application also relates to a composition comprising at least one organic compound or mixture as described above, and at least one organic solvent.

[0121] Specifically, the at least one organic solvent is selected from aromatic or heteroaromatic solvents, ester-based solvents, aromatic ketone-based solvents, aromatic ether-based solvents, aliphatic ketones, aliphatic ethers, alicyclic compounds, olefin compounds, borate esters, or phosphate esters.

[0122] The aromatic or heteroaromatic solvents may be selected from, but are not limited to, p-diisopropylbenzene, pentobenzene, tetrahydronaphthalene, cyclohexylbenzene, chloronaphthalene, 1,4-dimethylnaphthalene, 3-isopropylbiphenyl, p-methylisopropylbenzene, dipentylbenzene, tripentylbenzene, pentyltoluene, o-diethylbenzene, m-diethylbenzene, p-diethylbenzene, 1,2,3,4-tetramethylbenzene, 1,2,3,5-tetramethylbenzene, 1,2,4,5-tetramethylbenzene, butylbenzene, dodecylbenzene, dihexylbenzene, dibutylbenzene, p-diisopropylbenzene, cyclohexylbenzene, benzylbutylbenzene, dimethylnaphthalene, 3-isopropylbenzene. At least one of the following: biphenyl, p-methylisopropylbenzene, 1-methylnaphthalene, 1,2,4-trichlorobenzene, 4,4-difluorodiphenylmethane, 1,2-dimethoxy-4-(1-propenyl)benzene, diphenylmethane, 2-phenylpyridine, 3-phenylpyridine, N-methyldiphenylamine, 4-isopropylbiphenyl, α,α-dichlorodiphenylmethane, 4-(3-phenylpropyl)pyridine, benzyl benzoate, 1,1-bis(3,4-dimethylphenyl)ethane, 2-isopropylnaphthalene, quinoline, isoquinoline, methyl 2-furanoate, and ethyl 2-furanoate.

[0123] The ester-based solvent may be selected from, but is not limited to, alkyl octanoate, alkyl sebacate, alkyl stearate, alkyl benzoate, alkyl phenylacetate, alkyl cinnamate, alkyl oxalate, alkyl maleate, alkyl lactone, alkyl oleate, etc. At least one of octanoate, diethyl sebacate, diallyl phthalate, and isononyl isononanoate is particularly preferred.

[0124] The aromatic ketone-based solvent may be selected from, but is not limited to, 1-tetrahydronaphthone, 2-tetrahydronaphthone, 2-(phenylepoxy)tetrahydronaphthone, 6-(methoxy)tetrahydronaphthone, acetophenone, phenylacetone, benzophenone, and their derivatives, such as at least one of 4-methylacetophenone, 3-methylacetophenone, 2-methylacetophenone, 4-methylphenylacetone, 3-methylphenylacetone, and 2-methylphenylacetone.

[0125] The aromatic ether-based solvent may be selected from, but is not limited to, at least one of 3-phenoxytoluene, butoxybenzene, p-anisaldehyde dimethyl acetal, tetrahydro-2-phenoxy-2H-pyran, 1,2-dimethoxy-4-(1-propenyl)benzene, 1,4-benzodioxane, 1,3-dipropylbenzene, 2,5-dimethoxytoluene, 4-ethylbenzene, 1,3-dipropoxybenzene, 1,2,4-trimethoxybenzene, 4-(1-propenyl)-1,2-dimethoxybenzene, 1,3-dimethoxybenzene, glycidylphenyl ether, dibenzyl ether, 4-tert-butylanisole, trans-p-propenylanisole, 1,2-dimethoxybenzene, 1-methoxynaphthalene, diphenyl ether, 2-phenoxymethyl ether, 2-phenoxytetrahydrofuran, and ethyl-2-naphthyl ether.

[0126] The aliphatic ketone-based solvent may be selected from, but is not limited to, 2-nonanone, 3-nonanone, 5-nonanone, 2-decanone, 2,5-hexanedione, 2,6,8-trimethyl-4-nonanone, frankinc, phorone, isophorone, di-n-pentyl ketone, etc.; or aliphatic ethers, such as pentyl ether, hexyl ether, dioctyl ether, ethylene glycol dibutyl ether, diethylene glycol diethyl ether, diethylene glycol butyl methyl ether, diethylene glycol dibutyl ether, triethylene glycol dimethyl ether, triethylene glycol ethyl methyl ether, triethylene glycol butyl methyl ether, tripropylene glycol dimethyl ether, and tetraethylene glycol dimethyl ether.

[0127] It is understood that the organic solvent can be used alone or as a mixture of two or more organic solvents.

[0128] In some embodiments, the composition of this 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.

[0129] The other organic solvent may be selected from, but is not limited to, methanol, ethanol, 2-methoxyethanol, dichloromethane, trichloromethane, chlorobenzene, o-dichlorobenzene, tetrahydrofuran, anisole, morpholine, toluene, o-xylene, m-xylene, p-xylene, 1,4-dioxane, acetone, methyl ethyl ketone, 1,2-dichloroethane, 3-phenoxytoluene, 1,1,1-trichloroethane, 1,1,2,2-tetrachloroethane, ethyl acetate, butyl acetate, dimethylformamide, dimethylacetamide, dimethyl sulfoxide (DMSO), tetrahydronaphthalene, naphthane, and indene.

[0130] In some preferred embodiments, the organic solvents suitable for this application are solvents with Hansen solubility parameters within the following ranges:

[0131] 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;

[0132] 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;

[0133] δh (hydrogen bond strength) is in the range of 0.9-14.2 MPa1 / 2, especially in the range of 2.0-6.0 MPa1 / 2.

[0134] In some embodiments, the boiling point of the organic solvent is considered when selecting the composition according to this application. In at least some embodiments, the boiling point of the organic solvent is ≥150°C; preferably ≥180°C; more preferably ≥200°C; even more preferably ≥250°C; and most preferably ≥300°C. Boiling points within these ranges are beneficial for preventing nozzle clogging of the inkjet printhead.

[0135] It is understood that the organic solvent can evaporate from the composition system to form a thin film containing the organic compound of this application.

[0136] In some embodiments, the composition is a solution. In other embodiments, the composition is a suspension.

[0137] In the composition, the content of the organic compound or mixture can be 0.01-10 wt%, preferably 0.1-8 wt%, more preferably 0.2-5 wt%, and even more preferably 0.25-3 wt%.

[0138] This application also relates to the use of the composition as a coating or printing ink in the preparation of organic electronic devices. In some embodiments, the composition is used to prepare organic electronic devices by a printing or coating method. The printing or coating method may include, but is not limited to, inkjet printing, gravure printing, inkjet printing, letterpress printing, screen printing, dip coating, spin coating, doctor blade coating, roller printing, torsional roller printing, offset printing, flexographic printing, rotary printing, spraying, brushing, pad printing, slot extrusion coating, etc. Gravure printing, inkjet printing, and inkjet printing are preferred.

[0139] The solution or suspension may further include additives for adjusting viscosity, film-forming properties, and improving adhesion. These additives may be selected from, but are not limited to, at least one of surfactants, lubricants, wetting agents, dispersants, hydrophobic agents, and adhesives. Different printing or coating methods may have different requirements for coatings or printing inks; therefore, the concentration, viscosity, etc., of the solution or suspension can be adjusted accordingly to suit different printing or coating methods.

[0140] This application also provides the application of the organic compound, mixture, or composition as described above in organic electronic devices. The technical solution is as follows:

[0141] An organic electronic device comprising, or prepared from, the organic compound or mixture described above.

[0142] Furthermore, 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, wherein the organic functional layers comprise organic compounds, mixtures, or compositions as described above.

[0143] The organic functional layer is selected from hole injection layer (HIL), hole transport layer (HTL), light emission layer (EML), electron blocking layer (EBL), electron injection layer (EIL), electron transport layer (ETL), and hole blocking layer (HBL).

[0144] The organic electronic device can be, but is not limited to, organic light-emitting diodes (OLED devices), organic photovoltaic cells (OPV), organic light-emitting cells (OLEEC), organic field-effect transistors (OFETs), organic light-emitting field-effect transistors, organic lasers, organic spintronic devices, organic sensors, and organic plasmon emitting diodes (OLEDs). Preferably, the organic electronic device is an OLED device. Further, in one embodiment, the organic compound is preferably used in the light-emitting layer of the OLED device, and the light-emitting layer comprises the organic compound or mixture described above, or is prepared from the composition.

[0145] In some embodiments, one or more organic functional layers of the organic electronic device include at least a light-emitting layer. The material of the light-emitting layer includes a host material and a guest material. The host material includes organic compounds as described above, and the guest material includes pyrene-based organic compounds.

[0146] This application further relates to an organic electronic device comprising: a cathode, an anode, and one or more organic functional layers located between the cathode and the anode, wherein the organic functional layer comprises at least one light-emitting layer, the light-emitting layer material comprising a host material and a guest material, the host material comprising an organic compound of formula (1), and the guest material comprising a pyrene-based organic compound of formula (5).

[0147] The structure of the general formula (5) is as follows:

[0148]

[0149] in:

[0150] Ar4, Ar5, Ar6, and Ar7 are each independently selected from substituted or unsubstituted aromatic groups containing 6 to 60 ring atoms, or substituted or unsubstituted heteroaromatic groups containing 6 to 60 ring atoms, or combinations of these groups.

[0151] Each occurrence of R9 is independently selected from -H, -D, or a straight-chain alkyl group having 1 to 20 carbon atoms, a straight-chain alkoxy group having 1 to 20 carbon atoms, or a straight-chain thioalkoxy group having 1 to 20 carbon atoms, or a branched alkyl group having 3 to 20 carbon atoms, or a branched alkoxy group having 3 to 20 carbon atoms, or a branched thioalkoxy group having 3 to 20 carbon atoms, or a cyclic alkyl group having 3 to 20 carbon atoms, or a cyclic alkoxy group having 3 to 20 carbon atoms, or a cyclic thioalkoxy group having 3 to 20 carbon atoms, or a silyl group, or a ketone group having 1 to 20 carbon atoms, or a group having -H, -D, or a straight-chain alkyl group having 1 to 20 carbon atoms, or a branched alkyl group having 3 to 20 carbon atoms, or a branched alkoxy group having 3 to 20 carbon atoms, or a branched thioalkoxy group having 3 to 20 carbon atoms, or a branched thioalkoxy group having 3 to 20 carbon atoms, or a branched alkyl ... An alkoxycarbonyl group having 2 to 20 carbon atoms, or an aryloxycarbonyl group having 7 to 20 carbon atoms, a cyano group, a carbamoyl group, a haloformyl group, a formyl group, an isocyano group, an isocyanate group, a thiocyanate group, or an isothiocyanate group, a hydroxyl group, a nitro group, an amino group, a CF3 group, a Cl group, a Br group, a F group, an I group, or a substituted or unsubstituted aromatic group having 6 to 60 ring atoms, or a substituted or unsubstituted heteroaromatic group having 5 to 60 ring atoms, or a substituted or unsubstituted aryloxy group having 5 to 60 ring atoms, or a substituted or unsubstituted heteroaromatic group having 5 to 60 ring atoms, or a combination of these groups;

[0152] s is any integer selected from 0 to 8.

[0153] Further description of the organic compounds represented by general formula (1) is as described above.

[0154] In some embodiments, Ar4, Ar5, Ar6, and Ar7 are each independently selected from substituted or unsubstituted aromatic groups containing 6 to 14 ring atoms, or substituted or unsubstituted heteroaromatic groups containing 6 to 14 ring atoms, or combinations of these groups.

[0155] Furthermore, in some embodiments, Ar4, Ar5, Ar6, and Ar7 each independently include any of the structures shown below:

[0156]

[0157] in:

[0158] Each time V appears, it is independently selected from CR. 10 Or N;

[0159] W is selected from NR 11 CR 11 R 12 SiR 11 R 12 , O, S, S=O or SO2;

[0160] R 10 R 11 R 12Each occurrence is independently selected from -H, -D, or a straight-chain alkyl group having 1 to 20 carbon atoms, a straight-chain alkoxy group having 1 to 20 carbon atoms, or a straight-chain thioalkoxy group having 1 to 20 carbon atoms, or a branched alkyl group having 3 to 20 carbon atoms, or a branched alkoxy group having 3 to 20 carbon atoms, or a branched thioalkoxy group having 3 to 20 carbon atoms, or a cyclic alkyl group having 3 to 20 carbon atoms, or a cyclic alkoxy group having 3 to 20 carbon atoms, or a cyclic thioalkoxy group having 3 to 20 carbon atoms, or a silyl group, or a ketone group having 1 to 20 carbon atoms, or a group having -H, -D, or a straight-chain alkyl group having 1 to 20 carbon atoms, or a branched alkyl group having 3 to 20 carbon atoms, or a branched alkoxy group having 3 to 20 carbon atoms, or a branched thioalkoxy group having 3 to 20 carbon atoms, or a branched alkyl ... An alkoxycarbonyl group having 2 to 20 carbon atoms, or an aryloxycarbonyl group having 7 to 20 carbon atoms, a cyano group, a carbamoyl group, a haloformyl group, a formyl group, an isocyano group, an isocyanate group, a thiocyanate group, or an isothiocyanate group, a hydroxyl group, a nitro group, an amino group, a CF3 group, a Cl group, a Br group, a F group, an I group, or a substituted or unsubstituted aromatic group having 6 to 60 ring atoms, or a substituted or unsubstituted heteroaromatic group having 5 to 60 ring atoms, or a substituted or unsubstituted aryloxy group having 5 to 60 ring atoms, or a substituted or unsubstituted heteroaromatic group having 5 to 60 ring atoms, or a combination of these groups.

[0161] Furthermore, in some embodiments, R9, R 10 R 11 R 12 Each occurrence is independently selected from -H, -D, straight-chain alkyl with 1 to 10 carbon atoms, branched alkyl or cyclic alkyl or phenyl with 3 to 10 carbon atoms.

[0162] Furthermore, in some embodiments, R 13 R 14 R 15 R 16 Each time it appears, it is independently selected from -H, -D, straight-chain alkyl with 1 to 10 carbon atoms, branched alkyl or cyclic alkyl or phenyl with 3 to 10 carbon atoms.

[0163] Understandably, in this application, when V is a connection site, V is C; when W is a connection site, W is N.

[0164] In some embodiments, the pyrene-based organic compounds are selected from the following general structural formulas:

[0165]

[0166] Among them, R 10 Each time it appears, it is independently selected from -H, -D, straight-chain alkyl with 1 to 10 carbon atoms, or branched alkyl or cyclic alkyl or phenyl with 3 to 10 carbon atoms.

[0167] Furthermore, in some embodiments, the general formula (4) of the pyrene organic compound is selected from the following general formulas:

[0168]

[0169] Among them, R 10 Each time it appears, it is independently selected from -H, -D, straight-chain alkyl with 1 to 10 carbon atoms, or branched alkyl or cyclic alkyl or phenyl with 3 to 10 carbon atoms; W is as described above.

[0170] As an example, the organic compound of general formula (4) of this application may be selected from, but is not limited to, any of the following structures:

[0171]

[0172]

[0173] It is understood that the organic electronic device may also have some functional layers that are conventionally used in organic electronic devices and help improve device performance, such as electron transport layer, electron injection layer, electron blocking layer, hole blocking layer, hole transport layer, hole injection layer, hole blocking layer, light extraction layer, etc.

[0174] 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.

[0175] 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.

[0176] 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.

[0177] Materials suitable for use in these functional layers are described in detail above and in WO2010135519A1, US20090134784A1 and WO2011110277A1, the entire contents of which are hereby incorporated herein by reference.

[0178] In some embodiments, the organic electronic device further includes a substrate. The substrate may be located on the side of the anode away from the light-emitting layer, or on the side of the cathode away from the light-emitting layer. The substrate may be opaque or transparent. It is understood that when the substrate is transparent, the organic electronic device is a transparent light-emitting device. The substrate may also be rigid or flexible; for example, the substrate material may be plastic, metal, semiconductor wafer, or glass. Preferably, the substrate has a smooth surface, and a substrate without surface defects is particularly desirable. In a preferred embodiment, the substrate is a flexible substrate. The flexible substrate material 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 flexible substrate material may be polyethylene terephthalate (PET) or polyethylene glycol (2,6-naphthalene) (PEN).

[0179] The anode material is anode material known in the art for use in organic electronic devices, such as conductive metals, conductive metal oxides, or conductive polymers. In some embodiments, the absolute value of the difference between the work function of the anode material and the HOMO level or valence band level of the light emitter in the light-emitting layer or the p-type semiconductor material serving as a hole injection layer, hole transport layer, or 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 anode material may be selected from, but is 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 can be readily selected and used by those skilled in the art. The anode material can be deposited using any suitable technique, such as a suitable physical vapor deposition method, including radio frequency magnetron sputtering, vacuum thermal evaporation, electron beam (e-beam), etc. In some embodiments, the anode is patterned. Patterned ITO conductive substrates are commercially available and can be used to fabricate devices according to this application.

[0180] The cathode material is a cathode material known in the art for use in organic electronic devices, such as a conductive metal or conductive metal oxide. In some embodiments, the absolute value of the difference between the work function of the cathode material and the LUMO level or conduction band level of the luminescent material or the n-type semiconductor material serving as an electron injection layer, electron transport layer, or hole blocking layer in the light-emitting layer is less than 0.5 eV, preferably less than 0.3 eV, and most preferably less than 0.2 eV. In principle, all materials suitable for use as cathodes in OLEDs can be used as cathode materials for the devices of this application. As an example, the cathode material may be selected from, but is 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 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.

[0181] The material of the hole transport layer is a material known in the art for hole transport layers, for example, it may be selected from, but is not limited to, poly[bis(4-phenyl)(2,4,6-trimethylphenyl)amine] (PTXX), 2,2',7,7'-tetratetra[N,N-di(4-methoxyphenyl)amino]-9,9'-spiro-bisfluorene (spiro-omeTXD), 4,4'-cyclohexylbis[N,N-di(4-methylphenyl)aniline] (TXPC), N,N′-bis(1-naphthyl)-N,N′-diphenyl-1,1′-diphenyl-4, At least one of 4′-diamine (NPB), 4,4'-bis(N-carbazole)-1,1'-biphenyl (CBP), poly[(9,9-dioctylfluorenyl-2,7-diyl)-co-(4,4'-(N-(p-butylphenyl))diphenylamine)] (TFB), poly(9-vinylcarbazole) (PVK), polytriphenylamine (Poly-TPD), poly(3,4-ethylenedioxythiophene)-poly(styrenesulfonic acid) (PEDOT:PSS), and 4,4',4”-tris(carbazole-9-yl)triphenylamine (TCTX).

[0182] The material of the electron transport layer is a material known in the art for use in electron transport layers, for example, it may be selected from, but is not limited to, at least one of ET and Liq, PBD (2-(4-biphenyl)-5-phenyloxadiazole), 8-hydroxyquinoline aluminum (Xlq3) and graphene.

[0183] The chemical structural formulas of ET and Liq are as follows:

[0184]

[0185] The material of the hole injection layer is a material known in the art for hole injection layers, for example, it may be selected from, but is not limited to, at least one of 2,3,6,7,10,11-hexacyano-1,4,5,8,9,12-hexaazabenzophenanthrene (HXT-CN), PEDOT (polyethylene dioxythiophene), PEDOT:PSS and its derivatives doped with s-MoO3 (PEDOT:PSS:s-MoO3).

[0186] 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.

[0187] The light emission wavelength of the organic electronic device is between 300nm and 1000nm, preferably between 350nm and 900nm, and even more preferably between 400nm and 800nm.

[0188] This application also relates to electronic devices incorporating the aforementioned organic electronic devices. The electronic devices may be, but are not limited to, display devices, lighting devices, light sources, and sensors.

[0189] The present application will be specifically described below through specific embodiments. The following embodiments are only some embodiments of the present application and are not intended to limit the present application.

[0190] Example 1

[0191] The synthetic route of compound 1 in this embodiment is as follows:

[0192]

[0193] Synthesis of intermediate 1-1:

[0194] 2-Nitro-4-bromoiodobenzene (3.3 g, 10 mmol) and pinacol ester of o-hydroxyphenylboronic acid (2.2 g, 10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (100 ml / 10 ml), and Pd(PPh3)4 (0.12 g, 0.1 mmol) and potassium carbonate (5.5 g, 40 mmol) were added. The mixture was stirred at 100 °C for 12 h under a nitrogen atmosphere. After cooling, most of the solvent was removed by rotary evaporation, followed by extraction, washing with water, and separation. The organic phase was then subjected to column chromatography (eluent: PE) and recrystallized to give intermediate 1-1, yield: 83%. MS (ASAP) = 293.0.

[0195] Synthesis of intermediates 1-2:

[0196] In a 250 mL two-necked flask, intermediate 1-1 (2.9 g, 10 mmol), Pd(OAc)2 (0.22 g, 1.0 mmol), 3-nitropyridine (0.12 g, 1.0 mmol), and tert-butyl peroxide (3.9 g, 20 mmol) were placed, along with 100 mL of hexafluorobenzene and 10 mL of 1,3-dimethyl-2-imidazolinone. The reaction mixture was reacted at 100 °C for 12 h. After cooling, most of the solvent was removed by rotary evaporation, followed by extraction and washing with water. The organic phase was dried over MgSO4, filtered, and concentrated under vacuum. Column chromatography of the organic phase (eluent: PE:DCM = 5:1) yielded a pale yellow solid, intermediate 1-2, in 34% yield. MS (ASAP) = 291.0.

[0197] Synthesis of intermediates 1-3:

[0198] Intermediate 1-2 (5.8 g, 20 mmol) was placed in a 100 mL two-necked flask, and 30 mL of dichlorobenzene was added until completely dissolved. Triphenylphosphine (15.7 g, 60 mmol) was then added, and the mixture was stirred at 180 °C for 12 h under a nitrogen atmosphere. After cooling, the solvent was removed by vacuum distillation, followed by the addition of dichloromethane and washing with water. The mixture was then subjected to organic phase column chromatography (eluent: PE) and recrystallized to give intermediate 1-3 in 55% yield. MS (ASAP) = 259.0.

[0199] Synthesis of intermediates 1-4:

[0200] Intermediate 1-3 (10 g, 38.6 mmol), iodobenzene (20.4 g, 100 mmol), Pd2(dba)3 (2.9 g, 3.2 mmol), t-Bu3P (0.78 g, 3.9 mmol), and sodium tert-butoxide (15.5 g, 162 mmol) were weighed into a 500 mL three-necked flask. 200 mL of toluene was added, and the atmosphere was purged with nitrogen. The reaction was carried out at 80 °C for 12 h. The mixture was evaporated to dryness, washed with water, and subjected to column chromatography (eluent: PE) to give a white solid, which was intermediate 1-4. The yield of intermediate 1-4 was 80%. MS (ASAP) = 335.0.

[0201] Synthesis of intermediates 1-5:

[0202] Intermediate 1-4 (5 g, 15 mmol), (Bpin)2 (4.6 g, 18 mmol), AcOK (7.4 g, 75 mmol), and Pd(dppf)Cl2 (0.74 g, 1.0 mmol) were weighed into a 250 mL three-necked flask. 100 mL of 1,4-dioxane was added, and the mixture was purged with nitrogen. The reaction was carried out at 100 °C for 12 h. The mixture was evaporated to dryness, washed with water, and subjected to column chromatography (eluent: PE:DCM = 3:1) to obtain a colorless oil, which was intermediate 1-5. The yield of intermediate 1-5 was 93%. MS (ASAP) = 383.2.

[0203] Synthesis of Compound 1:

[0204] Intermediate 1-5 (3.8 g, 10 mmol) and 9-bromo-10-(1-naphthyl)anthracene (5.4 g, 14 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (100 ml / 10 ml), and Pd(PPh3)4 (0.81 g, 0.7 mmol) and potassium carbonate (5.5 g, 40 mmol) were added. The mixture was stirred at 100 °C for 12 h under a nitrogen atmosphere. After cooling, most of the solvent was removed by rotary evaporation, followed by extraction, washing with water, and separation. Organic phase column chromatography (eluent: PE) and recrystallization gave compound 1 in 63% yield. MS (ASAP) = 559.2.

[0205] Example 2

[0206] The synthetic route of compound 2 in this embodiment is as follows:

[0207]

[0208] Synthesis of intermediate 2-1:

[0209] 2-Nitroiodobenzene (2.5 g, 10 mmol) and pinacol ester of o-hydroxyphenylboronic acid (2.2 g, 10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (100 / 10 ml), and Pd(PPh3)4 (0.12 g, 0.1 mmol) and potassium carbonate (5.5 g, 40 mmol) were added. The mixture was stirred at 100 °C for 12 h under a nitrogen atmosphere. After cooling, most of the solvent was removed by rotary evaporation, followed by extraction, washing with water, and separation. The organic phase was then subjected to column chromatography (eluent: PE) and recrystallized to give intermediate 2-1, yield: 76%. MS (ASAP) = 215.1.

[0210] Synthesis of intermediate 2-2:

[0211] In a 250 mL two-necked flask, intermediate 2-1 (2.2 g, 10 mmol), Pd(OAc)2 (0.22 g, 1.0 mmol), 3-nitropyridine (0.12 g, 1.0 mmol), and tert-butyl peroxide (3.9 g, 20 mmol) were added, along with 100 mL of hexafluorobenzene and 10 mL of 1,3-dimethyl-2-imidazolinone. The reaction mixture was reacted at 100 °C for 12 h. After cooling, most of the solvent was removed by rotary evaporation, followed by extraction and washing with water. The organic phase was dried over MgSO4, filtered, and the filtrate was concentrated under vacuum. The organic phase was subjected to column chromatography (eluent: PE:DCM = 5:1) to give a pale yellow solid, intermediate 2-2, in 37% yield. MS (ASAP) = 213.0.

[0212] Synthesis of intermediates 2-3:

[0213] Intermediate 2-2 (6.4 g, 30 mmol) was added to a 100 mL two-necked flask, followed by 30 mL of dichlorobenzene until completely dissolved. Triphenylphosphine (26.2 g, 100 mmol) was then added, and the mixture was stirred at 180 °C for 12 h under a nitrogen atmosphere. After cooling, the solvent was removed by vacuum distillation, followed by the addition of dichloromethane and washing with water. The organic phase was subjected to column chromatography (eluent: PE) and recrystallized to give intermediate 2-3, yield: 58%. MS (ASAP) = 181.1.

[0214] Synthesis of intermediates 2-4:

[0215] Intermediate 2-3 (9.1 g, 50 mmol), p-bromoiodobenzene (28 g, 100 mmol), Pd2(dba)3 (2.9 g, 3.2 mmol), t-Bu3P (0.78 g, 3.9 mmol), and sodium tert-butoxide (15.5 g, 162 mmol) were weighed into a 500 mL three-necked flask. 200 mL of toluene was added, and the atmosphere was purged with nitrogen. The reaction was carried out at 80 °C for 12 h. The mixture was evaporated to dryness, washed with water, and subjected to column chromatography (eluent: PE) to give a white solid, intermediate 2-4, in 48% yield. MS (ASAP) = 335.0.

[0216] Synthesis of intermediates 2-5:

[0217] Weigh intermediate 2-4 (10 g, 30 mmol), (Bpin)2 (9.2 g, 36 mmol), AcOK (15 g, 150 mmol), and Pd(dppf)Cl2 (1.5 g, 2.0 mmol) into a 250 mL three-necked flask. Add 100 mL of 1,4-dioxane, displace nitrogen, and react at 100 °C for 12 h. Dry by rotary evaporation, wash with water, and perform column chromatography (eluent: PE:DCM = 3:1) to obtain a colorless oily substance, i.e., intermediate 2-5, in 82% yield. MS (ASAP) = 383.2.

[0218] Synthesis of compound 2:

[0219] Intermediate 2-5 (7.7 g, 20 mmol) and 9-bromo-10-(phenyl)anthracene (6.7 g, 20 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 mmol) and potassium carbonate (8.3 g, 60 mmol) were added. The mixture was stirred at 100 °C for 12 h under a nitrogen atmosphere. After cooling, most of the solvent was removed by rotary evaporation, followed by extraction and washing with water. The organic phase was subjected to column chromatography (eluent: PE) and recrystallized to give compound 2, yield: 67%. MS (ASAP) = 509.2.

[0220] Example 3

[0221] The synthetic route of compound 3 in this embodiment is as follows:

[0222]

[0223] Synthesis of intermediate 3-1:

[0224] 9-Bromo-10-(1-phenyl)anthracene (10 g, 30 mmol) and 4-bromo-1-phenylboronic acid (6.0 g, 30 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (200 ml / 20 ml), and Pd(PPh3)4 (3.5 g, 3 mmol) and potassium carbonate (21 g, 150 mmol) were added. The mixture was stirred at 100 °C for 12 h under a nitrogen atmosphere. After cooling, most of the solvent was removed by rotary evaporation, followed by extraction, washing with water, and separation. The organic phase was then subjected to column chromatography and recrystallization to give intermediate 3-1, yield: 89%. MS (ASAP) = 408.1.

[0225] Synthesis of compound 3:

[0226] Intermediate 3-1 (6.1 g, 15 mmol) and intermediate 1-5 (7.7 g, 20 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (100 mL / 10 mL), and Pd(PPh3)4 (0.87 g, 0.75 mmol) and potassium carbonate (6.2 g, 45 mmol) were added. The mixture was stirred at 100 °C for 12 h under a nitrogen atmosphere. After cooling, most of the solvent was removed by rotary evaporation, followed by extraction, washing with water, separation, organic phase column chromatography, and recrystallization to give compound 3, yield: 61%. MS (ASAP) = 585.2.

[0227] Example 4

[0228] The synthetic route of compound 4 in this embodiment is as follows:

[0229]

[0230] Synthesis of intermediate 4-1:

[0231] 9-Bromo-10-(2-naphthyl)anthracene (3.8 g, 10 mmol) and 4-bromo-2,3,5,6-tetramethyl-1-phenylboronic acid (3.1 g, 12 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (100 mL / 10 mL), and Pd(PPh3)4 (1.15 g, 1 mmol) and potassium carbonate (4.1 g, 30 mmol) were added. The mixture was stirred at 100 °C for 12 h under a nitrogen atmosphere. After cooling, most of the solvent was removed by rotary evaporation, followed by extraction, washing with water, and separation. The organic phase was then subjected to column chromatography and recrystallization to give intermediate 4-1, yield: 42%. MS (ASAP) = 514.1.

[0232] Synthesis of compound 4:

[0233] Intermediate 2-3 (9.1 g, 50 mmol), intermediate 4-1 (25.7 g, 50 mmol), Pd2(dba)3 (2.9 g, 3.2 mmol), t-Bu3P (0.78 g, 3.9 mmol), and sodium tert-butoxide (15.5 g, 162 mmol) were weighed into a 500 mL three-necked flask. 200 mL of toluene was added, and the atmosphere was purged with nitrogen. The reaction was carried out at 80 °C for 12 h. The product was evaporated to dryness, washed with water, and subjected to column chromatography (eluent: PE) to give a white solid in 88% yield. MS (ASAP) = 615.3.

[0234] Example 5

[0235] The synthetic route of the compound in this embodiment is as follows:

[0236]

[0237] Synthesis of intermediate 5-1:

[0238] 9,10-Dibromoanthracene (6.8 g, 20 mmol) and deuterated phenylboronic acid (3.0 g, 24 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (100 mL / 10 mL), and Pd(PPh3)4 (2.3 g, 2 mmol) and potassium carbonate (8.3 g, 60 mmol) were added. The mixture was stirred at 100 °C for 12 h under a nitrogen atmosphere. After cooling, most of the solvent was removed by rotary evaporation, followed by extraction, washing with water, and separation. The organic phase was then subjected to column chromatography and recrystallization to give intermediate 5-1, yield: 73%. MS (ASAP) = 337.1.

[0239] Synthesis of compound 5:

[0240] Intermediate 5-1 (3.4 g, 10 mmol) and intermediate 2-5 (3.8 g, 10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (100 mL / 10 mL), and Pd(PPh3)4 (1.15 g, 1 mmol) and potassium carbonate (4.1 g, 30 mmol) were added. The mixture was stirred at 100 °C for 12 h under a nitrogen atmosphere. After cooling, most of the solvent was removed by rotary evaporation, followed by extraction, washing with water, separation, organic phase column chromatography, and recrystallization to give compound 5, yield: 73%. MS (ASAP) = 514.2.

[0241] Example 6

[0242] The synthetic route of compound 6 in this embodiment is as follows:

[0243]

[0244] Synthesis of intermediate 6-1:

[0245] 9,10-Dibromoanthracene (3.4 g, 10 mmol) and deuterated 1-naphthoboric acid (1.8 g, 10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (100 mL / 10 mL), and Pd(PPh3)4 (1.15 g, 1 mmol) and potassium carbonate (8.3 g, 60 mmol) were added. The mixture was stirred at 100 °C for 12 h under a nitrogen atmosphere. After cooling, most of the solvent was removed by rotary evaporation, followed by extraction, washing with water, and separation. The organic phase was then subjected to column chromatography and recrystallization to give intermediate 6-1, yield: 76%. MS (ASAP) = 389.1.

[0246] Synthesis of compound 6:

[0247] Intermediate 6-1 (3.9 g, 10 mmol) and intermediate 1-5 (4.6 g, 12 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (100 mL / 10 mL), and Pd(PPh3)4 (1.15 g, 1 mmol) and potassium carbonate (4.1 g, 30 mmol) were added. The mixture was stirred at 100 °C for 12 h under a nitrogen atmosphere. After cooling, most of the solvent was removed by rotary evaporation, followed by extraction, washing with water, separation, organic phase column chromatography, and recrystallization to give compound 6, yield: 53%. MS (ASAP) = 566.2.

[0248] Example 7

[0249] The synthetic route of compound 7 in this embodiment is as follows:

[0250]

[0251] Synthesis of intermediate 7-1:

[0252] 9-Bromo-10-(2-Naphthyl)anthracene (3.8 g, 10 mmol) and 2-bromo-pyridine-5-boronic acid (2.0 g, 10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (100 mL / 10 mL), and Pd(PPh3)4 (1.15 g, 1 mmol) and potassium carbonate (4.1 g, 30 mmol) were added. The mixture was stirred at 100 °C for 12 h under a nitrogen atmosphere. After cooling, most of the solvent was removed by rotary evaporation, followed by extraction, washing with water, and separation. The organic phase was then subjected to column chromatography and recrystallization to give intermediate 7-1, yield: 81%. MS (ASAP) = 459.1.

[0253] Synthesis of Organic Compound 7:

[0254] Intermediate 2-3 (5.4 g, 30 mmol), intermediate 7-1 (13.8 g, 30 mmol), Pd2(dba)3 (2.9 g, 3.2 mmol), t-Bu3P (0.78 g, 3.9 mmol), and sodium tert-butoxide (15.5 g, 162 mmol) were weighed into a 500 mL three-necked flask. 200 mL of toluene was added, and the atmosphere was purged with nitrogen. The reaction was carried out at 80 °C for 12 h. The product was evaporated to dryness, washed with water, and subjected to column chromatography (eluent: PE) to give a white solid in 83% yield. MS (ASAP) = 560.2.

[0255] Example 8

[0256] The synthetic route of compound 8 in this embodiment is as follows:

[0257]

[0258] Synthesis of intermediate 8-1:

[0259] 9,10-Dibromoanthracene (3.4 g, 10 mmol) and 3,5-diphenyl-phenylboronic acid (2.8 g, 10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (100 mL / 10 mL), and Pd(PPh3)4 (1.15 g, 1 mmol) and potassium carbonate (8.3 g, 60 mmol) were added. The mixture was stirred at 100 °C for 12 h under a nitrogen atmosphere. After cooling, most of the solvent was removed by rotary evaporation, followed by extraction, washing with water, and separation. The organic phase was then subjected to column chromatography and recrystallization to give intermediate 8-1, yield: 63%. MS (ASAP) = 484.1.

[0260] Synthesis of compound 8:

[0261] Intermediate 8-1 (4.9 g, 10 mmol) and intermediate 1-5 (3.8 g, 10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (100 mL / 10 mL), and Pd(PPh3)4 (1.15 g, 1 mmol) and potassium carbonate (4.1 g, 30 mmol) were added. The mixture was stirred at 100 °C for 12 h under a nitrogen atmosphere. After cooling, most of the solvent was removed by rotary evaporation, followed by extraction, washing with water, separation, organic phase column chromatography, and recrystallization to give compound 8, yield: 55%. MS (ASAP) = 661.2.

[0262] Example 9

[0263] The synthetic route of compound 9 in this embodiment is as follows:

[0264]

[0265] Synthesis of intermediate 9-1:

[0266] Intermediate 9,10-dibromoanthracene (6.7 g, 20 mmol) and dibenzo[b,d]furan-2-boronic acid (4.3 g, 20 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 mmol) and potassium carbonate (14 g, 100 mmol) were added. The mixture was stirred at 100 °C for 12 h under a nitrogen atmosphere. After cooling, most of the solvent was removed by rotary evaporation, followed by extraction, washing with water, and separation. Organic phase column chromatography and recrystallization yielded intermediate 9-1, yield: 55%. MS (ASAP) = 422.0.

[0267] Synthesis of compound 9:

[0268] Intermediate 9-1 (4.2 g, 10 mmol) and intermediate 1-5 (3.8 g, 10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (100 mL / 10 mL), and Pd(PPh3)4 (1.15 g, 1 mmol) and potassium carbonate (4.1 g, 30 mmol) were added. The mixture was stirred at 100 °C for 12 h under a nitrogen atmosphere. After cooling, most of the solvent was removed by rotary evaporation, followed by extraction, washing with water, separation, organic phase column chromatography, and recrystallization to give compound 9, yield: 74%. MS (ASAP) = 599.2.

[0269] Example 10

[0270] The synthetic route of the compound in this embodiment is as follows:

[0271]

[0272] Synthesis of intermediate 10-1:

[0273] 9,10-Dibromoanthracene (3.4 g, 10 mmol) and fluoranthene-3-boronic acid (2.5 g, 10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (100 mL / 10 mL), and Pd(PPh3)4 (1.15 g, 1 mmol) and potassium carbonate (8.3 g, 60 mmol) were added. The mixture was stirred at 100 °C for 12 h under a nitrogen atmosphere. After cooling, most of the solvent was removed by rotary evaporation, followed by extraction, washing with water, and separation. The organic phase was then subjected to column chromatography and recrystallization to give intermediate 10⁻¹, yield: 64%. MS (ASAP) = 456.1.

[0274] Synthesis of compound 10:

[0275] Intermediate 10-1 (4.6 g, 10 mmol) and intermediate 10-11-5 (3.8 g, 10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (100 mL / 10 mL), and Pd(PPh3)4 (1.15 g, 1 mmol) and potassium carbonate (4.1 g, 30 mmol) were added. The mixture was stirred at 100 °C for 12 h under a nitrogen atmosphere. After cooling, most of the solvent was removed by rotary evaporation, followed by extraction, washing with water, separation, organic phase column chromatography, and recrystallization to give compound 10, yield: 48%. MS (ASAP) = 633.2.

[0276] Example 11

[0277] The synthetic route of compound 11 in this embodiment is as follows:

[0278]

[0279] Synthesis of intermediate 11-1:

[0280] 9,10-Dibromoanthracene (3.4 g, 10 mmol) and 1-pyreneboronic acid (2.5 g, 10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (100 mL / 10 mL), and Pd(PPh3)4 (1.15 g, 1 mmol) and potassium carbonate (8.3 g, 60 mmol) were added. The mixture was stirred at 100 °C for 12 h under a nitrogen atmosphere. After cooling, most of the solvent was removed by rotary evaporation, followed by extraction, washing with water, and separation. The organic phase was then subjected to column chromatography and recrystallization to give intermediate 11-1, yield: 73%. MS (ASAP) = 456.1.

[0281] Synthesis of compound 11:

[0282] Intermediate 11-1 (6.8 g, 15 mmol) and intermediate 2-5 (7.7 g, 20 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (100 ml / 10 ml), and Pd(PPh3)4 (1.7 g, 1.5 mmol) and potassium carbonate (6.2 g, 45 mmol) were added. The mixture was stirred at 100 °C for 12 h under a nitrogen atmosphere. After cooling, most of the solvent was removed by rotary evaporation, followed by extraction, washing with water, separation, organic phase column chromatography, and recrystallization to give compound 11, yield: 59%. MS (ASAP) = 633.2.

[0283] Example 12

[0284] The synthetic route of compound 12 in this embodiment is as follows:

[0285]

[0286] Synthesis of intermediate 12-1:

[0287] 9-Bromo-10-(4-tert-butylphenyl)anthracene (3.9 g, 10 mmol) and 6-bromo-2-naphthylboronic acid (2.5 g, 10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (100 ml / 10 ml), and Pd(PPh3)4 (1.15 g, 1 mmol) and potassium carbonate (4.1 g, 30 mmol) were added. The mixture was stirred at 100 °C for 12 h under a nitrogen atmosphere. After cooling, most of the solvent was removed by rotary evaporation, followed by extraction, washing with water, and separation. The organic phase was then subjected to column chromatography and recrystallization to give intermediate 12-1, yield: 71%. MS (ASAP) = 514.1.

[0288] Synthesis of organic compound 12:

[0289] Intermediate 2-3 (3.6 g, 20 mmol), intermediate 12-1 (10.3 g, 20 mmol), Pd2(dba)3 (1.8 g, 2.0 mmol), t-Bu3P (0.51 g, 2.5 mmol), and sodium tert-butoxide (9.6 g, 100 mmol) were weighed into a 500 mL three-necked flask. 200 mL of toluene was added, and the atmosphere was purged with nitrogen. The reaction was carried out at 80 °C for 12 h. The product was evaporated to dryness, washed with water, and subjected to column chromatography (eluent: PE) to give a white solid in 83% yield. MS (ASAP) = 560.2.

[0290] Example 13

[0291] The synthetic route of compound 13 in this embodiment is as follows:

[0292]

[0293] Synthesis of intermediate 13-1:

[0294] Intermediate 1-3 (13 g, 50 mmol), 2-iododibenzofuran (29.4 g, 100 mmol), Pd2(dba)3 (4.6 g, 5 mmol), t-Bu3P (1.2 g, 6.0 mmol), and sodium tert-butoxide (9.6 g, 100 mmol) were weighed into a 500 mL three-necked flask. 200 mL of toluene was added, and the atmosphere was purged with nitrogen. The reaction was carried out at 80 °C for 12 h. The solution was evaporated to dryness, washed with water, and subjected to column chromatography (eluent: PE) to give a white solid in 78% yield. MS (ASAP) = 425.0.

[0295] Synthesis of intermediate 13-2:

[0296] Weigh intermediate 13-1 (8.5 g, 20 mmol), (Bpin)2 (6.4 g, 25 mmol), AcOK (9.8 g, 100 mmol), and Pd(dppf)Cl2 (1.5 g, 2.0 mmol) into a 250 mL three-necked flask. Add 100 mL of 1,4-dioxane, displace nitrogen, and react at 100 °C for 12 h. Dry by rotary evaporation, wash with water, and perform column chromatography (eluent: PE:DCM = 3:1) to give a colorless oily substance in 92% yield. MS (ASAP) = 473.2.

[0297] Synthesis of compound 13:

[0298] Intermediate 13-2 (9.5 g, 20 mmol) and intermediate 6-1 (7.8 g, 20 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 mmol) and potassium carbonate (8.3 g, 60 mmol) were added. The mixture was stirred at 100 °C for 12 h under a nitrogen atmosphere. After cooling, most of the solvent was removed by rotary evaporation, followed by extraction, washing with water, and separation. Organic phase column chromatography (eluent: PE) and recrystallization were performed to give compound 13 in 69% yield. MS (ASAP) = 656.3.

[0299] Example 14

[0300] The synthetic route of compound 14 in this embodiment is as follows:

[0301]

[0302] Synthesis of intermediate 14-1:

[0303] Intermediate 1-3 (13 g, 50 mmol), 2-iodonaphthalene (25.4 g, 100 mmol), Pd2(dba)3 (4.6 g, 5 mmol), t-Bu3P (1.2 g, 6.0 mmol), and sodium tert-butoxide (9.6 g, 100 mmol) were weighed into a 500 mL three-necked flask. 200 mL of toluene was added, and the atmosphere was purged with nitrogen. The reaction was carried out at 80 °C for 12 h. The solution was evaporated to dryness, washed with water, and subjected to column chromatography (eluent: PE) to give a white solid in 73% yield. MS (ASAP) = 385.0.

[0304] Synthesis of intermediate 14-2:

[0305] Weigh intermediate 14-1 (7.7 g, 20 mmol), (Bpin)2 (6.4 g, 25 mmol), AcOK (9.8 g, 100 mmol), and Pd(dppf)Cl2 (1.5 g, 2.0 mmol) into a 250 mL three-necked flask. Add 100 mL of 1,4-dioxane, displace nitrogen, and react at 100 °C for 12 h. Dry by rotary evaporation, wash with water, and perform column chromatography (eluent: PE:DCM = 3:1) to give a colorless oily substance in 87% yield. MS (ASAP) = 433.2.

[0306] Synthesis of intermediate 14-3:

[0307] 9,10-Dibromoanthracene (6.8 g, 20 mmol) and 9,9-dimethylfluorene-2-boronic acid (4.8 g, 20 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (100 mL / 10 mL), and Pd(PPh3)4 (2.3 g, 2 mmol) and potassium carbonate (14 g, 100 mmol) were added. The mixture was stirred at 100 °C for 12 h under a nitrogen atmosphere. After cooling, most of the solvent was removed by rotary evaporation, followed by extraction, washing with water, and separation. The organic phase was then subjected to column chromatography and recrystallization to give intermediate 14-3, yield: 65%. MS (ASAP) = 448.1.

[0308] Synthesis of compound 14:

[0309] Intermediate 14-2 (8.7 g, 20 mmol) and intermediate 14-3 (9.0 g, 20 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 (14 g, 100 mmol) were added. The mixture was stirred at 100 °C for 12 h under a nitrogen atmosphere. After cooling, most of the solvent was removed by rotary evaporation, followed by extraction, washing with water, and separation. Organic phase column chromatography and recrystallization gave compound 14 in 55% yield. MS (ASAP) = 675.3.

[0310] Example 15

[0311] The synthetic route of compound 15 in this embodiment is as follows:

[0312]

[0313] Synthesis of intermediate 15-1:

[0314] 2-Nitro-4-bromoiodobenzene (3.3 g, 10 mmol) and pinacol ester of 2-hydroxy-4-bromophenylboronic acid (3.0 g, 10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (100 ml / 10 ml), and Pd(PPh3)4 (0.12 g, 0.1 mmol) and potassium carbonate (5.5 g, 40 mmol) were added. The mixture was stirred at 100 °C for 12 h under a nitrogen atmosphere. After cooling, most of the solvent was removed by rotary evaporation, followed by extraction, washing with water, and separation. The organic phase was then subjected to column chromatography (eluent: PE) and recrystallized to give intermediate 15-1, yield: 78%. MS (ASAP) = 372.9.

[0315] Synthesis of intermediate 15-2:

[0316] In a 250 mL two-necked flask, intermediate 15-1 (3.7 g, 10 mmol), Pd(OAc)2 (0.22 g, 1.0 mmol), 3-nitropyridine (0.12 g, 1.0 mmol), and tert-butyl peroxide (3.9 g, 20 mmol) were added, along with 100 mL of hexafluorobenzene and 10 mL of 1,3-dimethyl-2-imidazolinone. The reaction mixture was reacted at 100 °C for 12 h. After cooling, most of the solvent was removed by rotary evaporation, followed by extraction, washing with water, drying (MgSO4), filtration, and vacuum concentration. Organic phase column chromatography (eluent: PE:DCM = 5:1) yielded a pale yellow solid in 37% yield. MS (ASAP) = 370.9.

[0317] Synthesis of intermediate 15-3:

[0318] Intermediate 15-2 (7.4 g, 20 mmol) was added to a 100 mL two-necked flask, followed by 30 mL of dichlorobenzene until completely dissolved. Triphenylphosphine (15.7 g, 60 mmol) was then added, and the mixture was stirred at 180 °C for 12 h under a nitrogen atmosphere. After cooling, the solvent was removed by pressure distillation, followed by the addition of dichloromethane and washing with water. The mixture was then subjected to organic phase column chromatography (eluent: PE) and recrystallized to give intermediate 15-3, yield: 58%. MS (ASAP) = 338.9.

[0319] Synthesis of intermediate 15-4:

[0320] Weigh 10 g (38.6 mmol) of intermediate 15-3, 11.4 g (80 mmol) of iodomethane, and 14 g (100 mmol) of K₂CO₃ into a 500 mL three-necked flask. Add 200 mL of tetrahydrofuran, displace the nitrogen atmosphere, and react at 70 °C for 12 h. Dry by rotary evaporation, wash with water, and perform column chromatography (eluent: PE) to give a white solid in 92% yield. MS (ASAP) = 352.9.

[0321] Synthesis of intermediate 15-5:

[0322] Intermediate 15-4 (3.5 g, 10 mmol) and 10-(1-naphthyl)-9-anthraboronic acid (3.5 g, 10 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 (6.9 g, 50 mmol) were added. The mixture was stirred at 100 °C for 12 h under a nitrogen atmosphere. After cooling, most of the solvent was removed by rotary evaporation, followed by extraction, washing with water, and separation. The organic phase was then subjected to column chromatography (eluent: PE) and recrystallized to give intermediate 15-5, yield: 53%. MS (ASAP) = 575.1.

[0323] Synthesis of compound 15:

[0324] Intermediate 15-5 (5.8 g, 10 mmol) and 1-naphthoboric acid (3.4 g, 20 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (100 ml / 10 ml), and Pd(PPh3)4 (0.81 g, 0.7 mmol) and potassium carbonate (5.5 g, 40 mmol) were added. The mixture was stirred at 100 °C for 12 h under a nitrogen atmosphere. After cooling, most of the solvent was removed by rotary evaporation, followed by extraction, washing with water, and separation. Organic phase column chromatography (eluent: PE) and recrystallization were performed to give compound 15 in 92% yield. MS (ASAP) = 623.2.

[0325] Comparative Example

[0326] The organic compound in this comparative example is BH-Ref, and its chemical structural formula is as follows:

[0327]

[0328] The fabrication process of the OLED device comprising the above-described compounds is described in detail below through specific embodiments. The structure of the OLED device is: ITO / HIL / HTL / EML / ETL / cathode, and a schematic diagram of the OLED device is shown below. Figure 1As shown, 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.

[0329] The structural formulas of Liq, ET, and BD-1, compounds that may be involved in OLED fabrication, are as follows:

[0330]

[0331] The fabrication steps of OLED-1 are as follows:

[0332] a. Cleaning of ITO (Indium Tin Oxide) conductive glass substrate: Clean with various solvents (such as chloroform, acetone or isopropanol or one or more of these), and then perform ultraviolet ozone treatment.

[0333] b. HIL (hole injection layer, 40nm): 40nm PEDOT (polyethylene dioxythiophene, Clevios) TM AI4083 was spin-coated as HIL in a cleanroom and treated on a hot plate at 180°C for 10 minutes.

[0334] c. HTL (Hole Transport Layer, 20nm): 20nm 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 at a concentration of 5mg / ml, followed by treatment on a hot plate at 180°C for 60 minutes.

[0335] d. EML (Organic Light Emitting Layer, 40nm): The EML was formed by spin coating in a nitrogen glove box. The solution used was a methyl benzoate solution with different host and guest components (the weight ratio of host and guest components was 95:5), with a solution concentration of 15mg / ml. The solution was then treated on a hot plate at 140°C for 10 minutes. The host component was compound 1 from Example 1, and the guest material was selected from BD-1.

[0336] e. Electron transport layer and cathode: The heat-treated substrate is transferred to a vacuum chamber, and then ET and Liq are placed in different evaporation units and co-deposited in a high vacuum (1×10-6 mbar) at a ratio of 50% by weight to form a 20 nm electron transport layer on the light-emitting layer, followed by the deposition of an Al cathode with a thickness of 100 nm.

[0337] f. Encapsulation: The device is encapsulated in a nitrogen glove box using UV-cured resin.

[0338] The fabrication schemes for devices OLED-2, OLED-15, and OLED-Ref are the same as those for OLED-1, except that compound 1 in OLED-1 is replaced with the compound corresponding to the main material in Table 1.

[0339] The current-voltage (JV) characteristics of each OLED device were characterized using a characterization device, and the color efficiency (CE@1knits) and lifetime (LT90@1knits) were recorded. The results are shown in Table 1 below.

[0340] Table 1:

[0341]

[0342]

[0343] As shown in Table 1, compared with the blue OLED devices prepared using the organic compounds in the comparative example as the main material in the light-emitting layer, the OLED devices prepared using the organic compounds 1-15 in Examples 1-15 as the main material in the light-emitting layer have better color coordinates and longer lifespan.

[0344] Furthermore, the blue OLED devices fabricated using compounds 1-15 from Examples 1-15 as the host material in the emitting layer all exhibit luminous efficiencies in the range of 5-8 cd / A, demonstrating superior luminous efficiency. Moreover, devices OLED-5 and OLED-6 outperform other devices. The superiority of OLED-5 and OLED-6 may be attributed to the presence of deuterium in the host material of the emitting layer, which promotes luminescence.

[0345] The anthracene organic compounds containing heterocyclic fused rings exhibit fluorescence emission at blue light wavelengths and can be used as host materials in the light-emitting layer of organic electronic devices. Furthermore, organic electronic devices made using these organic compounds exhibit high luminous efficiency and long device lifespan.

[0346] The organic compounds, mixtures, compositions, and organic electronic devices provided in the embodiments of this application have been described in detail above. Specific examples have been used to illustrate the principles and implementation methods of this application. The descriptions of the above embodiments are only for the purpose of helping to understand the methods and core ideas of this application. At the same time, for those skilled in the art, there will be changes in the specific implementation methods and application scope based on the ideas of this application. Therefore, the content of this specification should not be construed as a limitation of this application.

Claims

1. An organic compound characterized in that, The organic compound is selected from any one of the following structures: 。 2. A mixture characterized in that: The mixture comprises the organic compound of claim 1 and at least one organic functional material selected from a hole injection material, a hole transport material, an electron transport material, an electron injection material, an electron blocking material, a hole blocking material, a host material, or a guest material.

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

4. An organic electronic device comprising at least one light-emitting layer, characterized in that: The light-emitting layer comprises the organic compound of claim 1.

Images