Organic Compounds, Mixtures, Compositions, and Organic Electronic Devices

Abstract

The present invention relates to an organic compound, a mixture, a composition and an organic electronic device. The organic compound has a structure represented by the general formula (1). It can be used as a novel blue light host material with good thermal stability. When it is used in an organic electronic device, the stability, efficiency and lifespan of the device can be improved.

Description

Technical Field

[0001] The present invention relates to the technical field of organic electroluminescence, and particularly to organic compounds, mixtures, compositions and organic electronic devices. Background Art

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

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

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

[0005] The light-emitting layer of traditional blue organic electroluminescent elements adopts a host-guest doping structure. The luminescent material (guest) can be used together with the matrix material (host) as a luminescent material to improve color purity, luminous efficiency, and stability. Since when using the host material / guest system as the light-emitting layer of a light-emitting device, the host material has a great influence on the efficiency and characteristics of the electroluminescent device, the selection of the host material is very important. Traditional blue host materials have poor stability, resulting in short device lifespan. At the same time, it is difficult for these compounds to achieve deep blue luminescence, thus posing problems in realizing full-color displays. Summary of the Invention

[0006] Based on this, the object of the present invention is to provide an organic compound, a mixture, a composition and an organic electronic device, which can be used as a new type of blue light host material with good thermal stability. When used in an organic electronic device, it can improve the stability, efficiency and lifespan of the device and achieve deep blue light emission.

[0007] The technical solution of the present invention is as follows:

[0008] An organic compound having a structure represented by the general formula (1):

[0009]

[0010] Wherein:

[0011] Ar1 is selected from a substituted or unsubstituted aromatic group containing 6 to 60 ring atoms, or a substituted or unsubstituted heteroaromatic group containing 6 to 60 ring atoms, or a combination of these groups;

[0012] L1 and L2 are independently selected from a single bond, or a substituted or unsubstituted aromatic group containing 6 to 60 ring atoms, or a substituted or unsubstituted heteroaromatic group containing 6 to 60 ring atoms, or a combination of these groups;

[0013] Each occurrence of R1, R2 and R3 is independently selected from -D, or a straight-chain alkyl group having 1 to 20 C atoms, or a straight-chain alkoxy group having 1 to 20 C atoms, or a straight-chain thioalkoxy group having 1 to 20 C atoms, or a branched-chain alkyl group having 3 to 20 C atoms, or a branched-chain alkoxy group having 3 to 20 C atoms, or a branched-chain thioalkoxy group having 3 to 20 C atoms, or a cyclic alkyl group having 3 to 20 C atoms, or a cyclic alkoxy group having 3 to 20 C atoms, or a cyclic thioalkoxy group having 3 to 20 C atoms, or a silyl group, or a ketone group having 1 to 20 C atoms, or an alkoxycarbonyl group having 2 to 20 C atoms, or an aryloxycarbonyl group having 7 to 20 C atoms, a cyano group, a carbamoyl group, a halocarbonyl group, a formyl group, an isocyano group, an isocyanate group, a thiocyanate group, or an isothiocyanate group, a hydroxyl group, a nitro group, an amino group, CF3, Cl, Br, F, I, 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 heteroaryloxy group having 5 to 60 ring atoms, or a combination of these groups; two adjacent R1s may or may not form a ring with each other;

[0014] m1 is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; m2 is selected from 0, 1, 2 or 3; m3 is selected from 0, 1, 2 or 3;

[0015] Each occurrence of R4 and R5 is independently selected from -H, -D, or a straight-chain alkyl group having 1 to 20 C atoms, or a branched-chain alkyl group having 3 to 20 C atoms, or a cyclic alkyl group having 3 to 20 C atoms, or a substituted or unsubstituted aromatic group having 6 to 20 ring atoms, or a substituted or unsubstituted heteroaromatic group having 5 to 20 ring atoms, or a combination of these groups.

[0016] The present invention further relates to a mixture comprising the above-mentioned organic compound and at least one organic functional material.

[0017] The present invention further relates to a composition comprising the above-mentioned organic compound or the above-mentioned mixture and at least one organic solvent.

[0018] The present invention further relates to an organic electronic device comprising the above-mentioned organic compound, or the above-mentioned mixture, or prepared from the above-mentioned composition.

[0019] Advantageous effects:

[0020] The organic compound of the present invention is an anthracene derivative containing a seven-membered fused heterocycle, which can be used as a host material in the light-emitting layer of an organic electronic device, enabling the device to achieve an ideal electrical balance state and improving the stability, efficiency, and lifespan of the device. Description of the drawings

[0021] Figure 1 It is a schematic structural diagram of an OLED device according to an embodiment of the present invention. Detailed implementation manners

[0022] To facilitate the understanding of the present invention, the present invention will be described more comprehensively below with reference to relevant embodiments. Preferred embodiments of the present invention are given in the embodiments. However, the present invention can be implemented in many different forms and is not limited to the embodiments described herein. On the contrary, these embodiments are provided to make the understanding of the disclosure of the present invention more thorough and comprehensive.

[0023] As used herein, the terms "and / or", "or / and", and "and / or" include any one of two or more related listed items, as well as any and all combinations of the related listed items. The any and all combinations include combinations of any two related listed items, any more than two related listed items, or all related listed items. It should be noted that when at least three items are connected by at least two conjunctions selected from "and / or", "or / and", and "and / or", it should be understood that in this application, this technical solution undoubtedly includes the technical solution connected by "logical AND", and also undoubtedly includes the technical solution connected by "logical OR". For example, "A and / or B" includes three parallel solutions: A, B, and A + B. Another example is the technical solution of "A, and / or, B, and / or, C, and / or, D", which includes any one of A, B, C, and D (that is, the technical solution connected by "logical OR"), and also includes any and all combinations of A, B, C, and D, that is, combinations of any two or any three of A, B, C, and D, and also includes the four-item combination of A, B, C, and D (that is, the technical solution connected by "logical AND").

[0024] In the present invention, the composition and the printing ink, or the ink have the same meaning and can be interchanged.

[0025] In the present invention, the aromatic group, the aromatic, and the aromatic ring system have the same meaning and can be interchanged.

[0026] In the present invention, the heteroaromatic group, the heteroaromatic, and the heteroaromatic ring system have the same meaning and can be interchanged.

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

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

[0029] In the present invention, when the same substituent appears multiple times, it can be independently selected from different groups. For example, if the general formula contains multiple R1s, then R1 can be independently selected from different groups.

[0030] In the present invention, "substituted or unsubstituted" means that the defined group may be substituted or may not be substituted. When the defined group is substituted, it should be understood that the defined group may be substituted by one or more substituents R, where R is selected from, but not limited to: deuterium atom, cyano group, isocyano group, nitro group or halogen, alkyl group containing 1 - 30 C atoms, heterocyclic group containing 3 - 20 ring atoms, aromatic group containing 6 - 20 ring atoms, heteroaromatic group containing 5 - 20 ring atoms, -NR’R”, silyl group, carbonyl group, alkoxycarbonyl group, aryloxycarbonyl group, carbamoyl group, halocarbonyl group, formyl group, isocyanate group, thiocyanate group, isothiocyanate group, hydroxyl group, trifluoromethyl group, and the above groups may also be further substituted by substituents acceptable in the art; it is understandable that R’ and R” in -NR’R” are each independently selected from, but not limited to: H, deuterium atom, cyano group, isocyano group, nitro group or halogen, C 1-10 alkyl group, heterocyclic group containing 3 - 20 ring atoms, aromatic group containing 6 - 20 ring atoms, heteroaromatic group containing 5 - 20 ring atoms. Preferably, R is selected from, but not limited to: deuterium atom, cyano group, isocyano group, nitro group or halogen, alkyl group containing 1 - 10 C atoms, heterocyclic group containing 3 - 10 ring atoms, aromatic group containing 6 - 20 ring atoms, heteroaromatic group containing 5 - 20 ring atoms, silyl group, carbonyl group, alkoxycarbonyl group, aryloxycarbonyl group, carbamoyl group, halocarbonyl group, formyl group, isocyanate group, thiocyanate group, isothiocyanate group, hydroxyl group, trifluoromethyl group, and the above groups may also be further substituted by substituents acceptable in the art.

[0031] In the present invention, "number of ring atoms" means the number of atoms among the atoms constituting the ring itself of a structural compound obtained by bonding atoms into a ring (for example, monocyclic compound, fused-ring compound, crosslinked compound, carbocyclic compound, heterocyclic compound). When the ring is substituted by a substituent, the atoms contained in the substituent are not included in the ring-forming atoms. The same applies to the "number of ring atoms" described below under the condition of no special explanation. For example, the number of ring atoms of a benzene ring is 6, the number of ring atoms of a naphthalene ring is 10, and the number of ring atoms of a thiophenyl group is 5.

[0032] "Aryl or aromatic group" refers to an aromatic hydrocarbon group derived by removing one hydrogen atom from an aromatic ring compound, which can be a monocyclic aryl group, a fused-ring aryl group, or a polycyclic aryl group. For a polycyclic ring system, at least one is an aromatic ring system. For example, "substituted or unsubstituted aryl group having 6 to 40 ring atoms" refers to an aryl group containing 6 to 40 ring atoms, preferably a substituted or unsubstituted aryl group having 6 to 30 ring atoms, more preferably a substituted or unsubstituted aryl group having 6 to 18 ring atoms, particularly preferably a substituted or unsubstituted aryl group having 6 to 14 ring atoms, and the aryl group is optionally further substituted; suitable examples include but are not limited to: phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthryl, fluoranthenyl, triphenylenyl, pyrenyl, perylenyl, tetracenyl, fluorenyl, binaphthyl, acenaphthylenyl and their derivatives. It can be understood that multiple aryl groups can also be interrupted by short non-aromatic units (e.g., <10% non-H atoms, such as C, N or O atoms), specifically such as acenaphthene, fluorene, or 9,9-diarylfluorene, triarylamine, diaryl ether systems should also be included in the definition of aryl groups.

[0033] "Heteroaryl or heteroaromatic group" refers to a group in which at least one carbon atom in the aryl group is replaced by a non-carbon atom, and the non-carbon atom can be an N atom, an O atom, an S atom, etc. For example, "substituted or unsubstituted heteroaryl 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, particularly preferably a substituted or unsubstituted heteroaryl group having 6 to 14 ring atoms, and the heteroaryl group is optionally further substituted. Suitable examples include but are not limited to: thienyl, furyl, pyrrolyl, imidazolyl, oxadiazolyl, triazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, acridinyl, pyridazinyl, pyrazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, benzothienyl, benzofuryl, indolyl, pyrroloimidazolyl, pyrrolopyrrolyl, thienopyrrolyl, thienothienyl, furanopyrrolyl, furanofuryl, thienofuryl, benzisoxazolyl, benzisothiazolyl, benzimidazolyl, phthalazinyl, phenanthridinyl, perimidinyl, quinazolinone, dibenzothienyl, dibenzofuryl, carbazolyl and their derivatives.

[0034] In the present invention, "alkyl" may represent linear, branched and / or cyclic alkyl. The number of carbon atoms of the alkyl may be 1 to 50, 1 to 30, 1 to 20, 1 to 10 or 1 to 6. Non-limiting examples of the alkyl include methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, tert-butyl, isobutyl, 2-ethylbutyl, 3,3-dimethylbutyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, cyclopentyl, 1-methylpentyl, 3-methylpentyl, 2-ethylpentyl, 4-methyl-2-pentyl, n-hexyl, 1-methylhexyl, 2-ethylhexyl, 2-butylhexyl, cyclohexyl, adamantyl, etc.

[0035] In the present invention, "halogen" or "halo group" refers to F, Cl, Br or I.

[0036] In the present invention, "alkoxy" refers to a group having -O-alkyl, that is, the alkyl as defined above is connected to the parent nuclear structure via an oxygen atom. Suitable examples of the phrase containing this term include, but are not limited to: methoxy (-O-CH3 or -OMe), ethoxy (-O-CH2CH3 or -OEt) and tert-butoxy (-O-C(CH3)3 or -OtBu).

[0037] "Amino group" refers to a derivative of amine, having a structural feature of the formula -N(X)2, wherein each "X" is independently H, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted heterocyclic group, etc. Non-limiting types of the amino group include -NH2, -N(alkyl)2, -NH(alkyl), -N(cycloalkyl)2, -NH(cycloalkyl), -N(heterocyclic group)2, -NH(heterocyclic group), -N(aryl)2, -NH(aryl), -N(alkyl)(aryl), -N(alkyl)(heterocyclic group), -N(cycloalkyl)(heterocyclic group), -N(aryl)(heteroaryl), -N(alkyl)(heteroaryl), etc.

[0038] In the present invention, unless otherwise defined, hydroxyl group refers to -OH, carboxyl group refers to -COOH, carbonyl group refers to -C(=O)-, amino group refers to -NH2, formyl group refers to -C(=O)H, halocarbonyl group refers to -C(=O)Z (wherein, Z represents halogen), carbamoyl group refers to -C(=O)NH2, isocyanate group refers to -NCO, and isothiocyanate group refers to -NCS.

[0039] In the present invention, "*" represents the connection site.

[0040] In the present invention, when there are multiple substituents with the same symbol on the same group, each substituent may be the same as or different from each other. For example 6 Rs on the benzene ring 1 may be the same as or different from each other.

[0041] In the present invention, the single bond to which the substituent is connected runs through the corresponding ring, indicating that the substituent can be connected to any position of the ring, for example In which R is connected to any substitutable position of the benzene ring; express Can be used with The benzene ring can be fused at any position.

[0042] According to the present invention, the cyclic alkyl or cycloalkyl group has the same meaning and can be interchanged.

[0043] In the present invention, "two adjacent R's form a ring with each other" means a ring system formed by two adjacent R's connecting with each other, and the ring system can be selected from aliphatic hydrocarbon rings, aliphatic heterocycles, aromatic hydrocarbon rings or aromatic heterocycles.

[0044] The “combinations thereof”, “any combinations thereof”, “any combination thereof” etc. used in the present invention include all suitable combinations of any two or more of the listed items.

[0045] In the present invention, “further”, “furthermore”, “particularly”, etc. are used for descriptive purposes to indicate differences in content, but should not be construed as limiting the scope of protection of the present invention.

[0046] In the present invention, "optionally", "optional", and "optional" mean optional, that is, any one of the two parallel solutions of "yes" or "no". If multiple "options" appear in a technical solution, unless otherwise specified and there is no contradiction or mutual restriction, each "optional" is independent.

[0047] In the present invention, the technical features described in an open manner include closed technical solutions composed of the listed features, and also include open technical solutions containing the listed features.

[0048] The technical solution of the present invention is as follows:

[0049] An organic compound having a structure as shown in general formula (1):

[0050]

[0051] in:

[0052] Ar1 is selected from a substituted or unsubstituted aromatic group containing 6 to 60 ring atoms, or a substituted or unsubstituted heteroaromatic group containing 6 to 60 ring atoms, or a combination of these groups;

[0053] L1 and L2 are independently selected from a single bond, or a substituted or unsubstituted aromatic group containing 6 to 60 ring atoms, or a substituted or unsubstituted heteroaromatic group containing 6 to 60 ring atoms, or a combination of these groups;

[0054] Each occurrence of R1, R2, and R3 is independently selected from -D, or a straight-chain alkyl group having 1 to 20 C atoms, or a straight-chain alkoxy group having 1 to 20 C atoms, or a straight-chain thioalkoxy group having 1 to 20 C atoms, or a branched-chain alkyl group having 3 to 20 C atoms, or a branched-chain alkoxy group having 3 to 20 C atoms, or a branched-chain thioalkoxy group having 3 to 20 C atoms, or a cyclic alkyl group having 3 to 20 C atoms, or a cyclic alkoxy group having 3 to 20 C atoms, or a cyclic thioalkoxy group having 3 to 20 C atoms, or a silyl group, or a keto group having 1 to 20 C atoms, or an alkoxycarbonyl group having 2 to 20 C atoms, or an aryloxycarbonyl group having 7 to 20 C atoms, a cyano group, a carbamoyl group, a halocarbonyl group, a formyl group, an isocyano group, an isocyanate group, a thiocyanate group, or an isothiocyanate group, a hydroxyl group, a nitro group, an amino group, CF3, Cl, Br, F, I, 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 heteroaryloxy group having 5 to 60 ring atoms, or a combination of these groups; two adjacent R1 groups may or may not form a ring with each other;

[0055] m1 is selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8; m2 is selected from 0, 1, 2, or 3; m3 is selected from 0, 1, 2, or 3;

[0056] Each occurrence of R4 and R5 is independently selected from -H, -D, or a straight-chain alkyl group having 1 to 20 C atoms, or a branched-chain alkyl group having 3 to 20 C atoms, or a cyclic alkyl group having 3 to 20 C atoms, or a substituted or unsubstituted aromatic group having 6 to 20 ring atoms, or a substituted or unsubstituted heteroaromatic group having 5 to 20 ring atoms, or a combination of these groups.

[0057] In one embodiment, Ar1 is selected from a substituted or unsubstituted aromatic group containing 6 to 30 ring atoms, or a substituted or unsubstituted heteroaromatic group containing 6 to 30 ring atoms. In one embodiment, Ar1 is selected from a substituted or unsubstituted aromatic group containing 6 to 16 ring atoms, or a substituted or unsubstituted heteroaromatic group containing 6 to 16 ring atoms.

[0058] In one embodiment, the said Ar1 is selected from one or a combination of several of the following groups:

[0059]

[0060] Wherein:

[0061] Each occurrence of X is independently selected from CR6 or N; preferably, each occurrence of X is independently selected from CR6;

[0062] Y is selected from NR7, CR8R9, SiR8R9, O, S, S=O or SO2;

[0063] Each occurrence of R6, R7, R8, and R9 is independently selected from -H, -D, or a straight-chain alkyl group having 1 to 20 carbon atoms, or 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-chain alkyl group having 3 to 20 carbon atoms, or a branched-chain alkoxy group having 3 to 20 carbon atoms, or a branched-chain 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 keto group having 1 to 20 carbon atoms, or an alkoxycarbonyl group having 2 to 20 carbon atoms, or an aryloxycarbonyl group having 7 to 20 carbon atoms, cyano, carbamoyl, halocarbonyl, formyl, isocyano, isocyanate, thiocyanate, or isothiocyanate, hydroxy, nitro, amino, 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 heteroaryloxy group having 5 to 60 ring atoms, or a combination of these groups; R8 and R9 may or may not form a ring with each other.

[0064] It is understood that in the present invention, when X is a linking site, X is C; when Y is a linking site, Y is N.

[0065] In a specific example, the structure of the organic compound is selected from the structures shown in any one of the general formulas (2-1) to (2-4):

[0066]

[0067] In a specific example, each occurrence of R6 is independently selected from -H, -D, a linear alkyl group having 1 to 10 C atoms, a branched alkyl group having 3 to 10 C atoms, a cyclic alkyl group having 3 to 10 C atoms, a silyl group, an isocyano group, a nitro group, an amino group, -CF3, -Cl, -Br, -F, -I, a substituted or unsubstituted aromatic group having 6 to 20 ring atoms, a substituted or unsubstituted heteroaromatic group having 5 to 20 ring atoms, or a combination of these groups; further, each occurrence of R6 is independently selected from: -H, -D, a linear alkyl group having 1 to 8 C atoms, a branched alkyl group having 3 to 8 C atoms, a cyclic alkyl group having 3 to 8 C atoms, a substituted or unsubstituted aromatic group having 6 to 10 ring atoms, a substituted or unsubstituted heteroaromatic group having 5 to 10 ring atoms, or a combination of these groups.

[0068] Preferably, the substituent is selected from -D, a linear alkyl group having 1 to 4 C atoms, a branched alkyl group having 3 to 4 C atoms, or a phenyl group, or a pyridyl group.

[0069] Still further, each occurrence of R6 is independently selected from -H or -D, or a linear alkyl group having 1 to 4 C atoms, a branched alkyl group having 3 to 4 C atoms, or a phenyl group, or a naphthyl group.

[0070] In a certain embodiment, at least one R6 is selected from D.

[0071] In a specific example, each occurrence of R7 is independently selected from a linear alkyl group having 1 to 10 C atoms, a branched alkyl group having 3 to 10 C atoms, a cyclic alkyl group having 3 to 10 C atoms, a substituted or unsubstituted aromatic group having 6 to 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 R7 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; still further, each occurrence of R7 is independently selected from: methyl, ethyl, isopropyl, tert-butyl, phenyl, pyridyl, pyrimidinyl, triazinyl, biphenyl, terphenyl, or naphthyl.

[0072] In a specific example, each occurrence of R8 and R9 is independently selected from -H, -D, a straight-chain alkyl group having 1 to 8 C atoms, a branched-chain alkyl group having 3 to 8 C atoms, or a cyclic alkyl group having 3 to 8 C atoms, a substituted or unsubstituted aromatic group having 6 to 10 ring atoms, a substituted or unsubstituted heteroaromatic group having 5 to 10 ring atoms, or a combination of these groups; further, each occurrence of R8 and R9 is independently selected from: -H, -D, methyl, ethyl, isopropyl, phenyl, pyridyl, pyrimidyl, triazinyl, biphenyl, terphenyl, or naphthyl.

[0073] In some preferred embodiments, Ar1 is selected from one of the following groups:

[0074]

[0075] Wherein: * represents the connection site.

[0076] In one embodiment, each occurrence of R1, R2, and R3 is independently selected from -D, or a straight-chain alkyl group having 1 to 10 C atoms, or a straight-chain alkoxy group having 1 to 10 C atoms, or a straight-chain thioalkoxy group having 1 to 10 C atoms, or a branched-chain alkyl group having 3 to 10 C atoms, or a branched-chain alkoxy group having 3 to 10 C atoms, or a branched-chain thioalkoxy group having 3 to 10 C atoms, or a cyclic alkyl group having 3 to 20 C atoms, or a cyclic alkoxy group having 3 to 10 C atoms, or a cyclic thioalkoxy group having 3 to 10 C atoms, or a silyl group, or a keto group having 1 to 10 C atoms, or an alkoxycarbonyl group having 2 to 10 C atoms, or an aryloxycarbonyl group having 7 to 10 C atoms, cyano, carbamoyl, halocarbonyl, formyl, isocyano, isocyanate, thiocyanate, or isothiocyanate, hydroxy, nitro, amino, CF3, Cl, Br, F, I, or a substituted or unsubstituted aromatic group having 6 to 30 ring atoms, or a substituted or unsubstituted heteroaromatic group having 6 to 30 ring atoms, or a substituted or unsubstituted aryloxy group having 6 to 30 ring atoms, or a substituted or unsubstituted heteroaryloxy group having 6 to 30 ring atoms, or a combination of these groups.

[0077] Further, each occurrence of R1, R2, and R3 is independently selected from -D, or a straight-chain alkyl group having 1 to 8 C atoms, or a straight-chain alkoxy group having 1 to 8 C atoms, or a branched-chain alkyl group having 3 to 8 C atoms, or a cyclic alkyl group having 3 to 8 C atoms, or a silyl group, -CN, isocyano, hydroxy, nitro, -CF3, -Cl, -Br, -F, or a substituted or unsubstituted aromatic group having 6 to 10 ring atoms, or a substituted or unsubstituted heteroaromatic group having 5 to 10 ring atoms, or a combination of these groups.

[0078] In one embodiment, each occurrence of R1 is independently selected from: -D, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, tert-butyl, isobutyl, 2-ethylbutyl, 3,3-dimethylbutyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, cyclopentyl, 1-methylpentyl, 3-methylpentyl, 2-ethylpentyl, 4-methyl-2-pentyl, n-hexyl, 1-methylhexyl, 2-ethylhexyl, 2-butylhexyl, methoxy, ethoxy, hydroxy, cyclohexyl, adamantyl, phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthryl, triazinyl, pyridyl, pyrimidyl, imidazolyl, furyl, thienyl, benzofuryl, benzothienyl, indolyl, substituted or unsubstituted carbazolyl, dibenzothiophenyl, dibenzofuryl, substituted or unsubstituted fluorenyl, or a straight-chain alkoxy group having 1 to 4 C atoms.

[0079] In one embodiment, each occurrence of R2 and R3 is independently selected from: -D, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, tert-butyl, isobutyl, 2-ethylbutyl, 3,3-dimethylbutyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, cyclopentyl, 1-methylpentyl, 3-methylpentyl, 2-ethylpentyl, 4-methyl-2-pentyl, n-hexyl, 1-methylhexyl, 2-ethylhexyl, 2-butylhexyl, methoxy, ethoxy, hydroxy, cyclohexyl, adamantyl, phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthryl, triazinyl, pyridyl, pyrimidyl, imidazolyl, furyl, thienyl, benzofuryl, benzothienyl, indolyl, substituted or unsubstituted carbazolyl, dibenzothiophenyl, dibenzofuryl, substituted or unsubstituted fluorenyl.

[0080] Further, the substituted carbazolyl is phenyl-substituted carbazolyl.

[0081] Further, the substituted fluorenyl is an alkyl-substituted fluorenyl having 1 to 10 C atoms.

[0082] In one embodiment, m1 is 2, 3, 4, 5, 6, 7 or 8, and for each occurrence of two adjacent R1s, the structure of the ring formed therebetween is: wherein, * represents the connection site.

[0083] In one embodiment, m1, m2 and m3 are all selected from 0.

[0084] In one embodiment, each occurrence of R4 and R5 is independently selected from -H, -D, or a straight-chain alkyl group having 1 to 10 C atoms, or a branched-chain alkyl group having 3 to 10 C atoms, or a cyclic alkyl group having 3 to 10 C atoms, or a substituted or unsubstituted aromatic group having 6 to 14 ring atoms, or a substituted or unsubstituted heteroaromatic group having 6 to 14 ring atoms, or a combination of these groups.

[0085] Further, each occurrence of R4 and R5 is independently selected from -H, -D, a linear alkyl group having 1 to 4 C atoms, a branched alkyl group having 3 to 5 C atoms, a cyclic alkyl group having 3 to 5 C atoms, an unsubstituted aromatic group having 6 to 14 ring atoms, an unsubstituted heteroaromatic group having 6 to 14 ring atoms, an aromatic group having 6 to 14 ring atoms substituted with an alkyl group having 1 to 5 C atoms, or a heteroaromatic group having 6 to 14 ring atoms substituted with an alkyl group having 1 to 5 C atoms.

[0086] In one embodiment, each occurrence of R4 and R5 is independently selected from -H, -D, a linear alkyl group having 1 to 4 C atoms, a branched alkyl group having 3 to 5 C atoms, a cyclic alkyl group having 3 to 5 C atoms, or one of the following groups:

[0087]

[0088] Wherein:

[0089] Each occurrence of X1 is independently selected from CR 10 or N;

[0090] Y1 is selected from NR 11 、CR 12 R 13 、SiR 12 R 13 、O, S, S=O or SO2;

[0091] R 10 、R 11 、R 12 、R 13 Each occurrence is independently selected from -H, -D, a linear alkyl group having 1 to 10 C atoms, a branched alkyl group having 3 to 20 C atoms, a cyclic alkyl group having 3 to 20 C atoms, a silyl group, a cyano group, an isocyano group, a hydroxyl group, a nitro group, -CF3, -Cl, -Br, -F, -I, or a substituted or unsubstituted aromatic group having 6 to 10 ring atoms, or a substituted or unsubstituted heteroaromatic group having 5 to 10 ring atoms; R 12 and R 13 either form a ring or do not form a ring with each other.

[0092] It is understood that in the present invention, when X1 is a connection site, X1 is C.

[0093] In some preferred embodiments, each occurrence of R4 and R5 is independently selected from -H, -D, a linear alkyl group having 1 to 4 C atoms, a branched alkyl group having 3 to 4 C atoms, or one of the following groups:

[0094]

[0095] Wherein: * represents a linking site.

[0096] In one embodiment, each occurrence of R4 and R5 is independently selected from the same group;

[0097] In another embodiment, each occurrence of R4 and R5 is independently selected from different groups.

[0098] In one embodiment, L1 and L2 are each independently selected from a single bond, a substituted or unsubstituted aromatic group having 6 to 14 ring atoms, and a substituted or unsubstituted heteroaromatic group having 6 to 14 ring atoms.

[0099] Furthermore, L1 and L2 are independently selected from a single bond or a combination of one or more of the following groups:

[0100]

[0101] Wherein:

[0102] Each occurrence of X2 is independently selected from CR 14 or N;

[0103] Y2 is selected from NR 15 、CR 16 R 17 、SiR 16 R 17 、O, S, S=O or SO2;

[0104] R 14 、R 15 、R 16 、R 17Each occurrence is independently selected from -H, -D, or a straight-chain alkyl group having 1 to 20 C atoms, or a straight-chain alkoxy group having 1 to 20 C atoms, or a straight-chain thioalkoxy group having 1 to 20 C atoms, or a branched-chain alkyl group having 3 to 20 C atoms, or a branched-chain alkoxy group having 3 to 20 C atoms, or a branched-chain thioalkoxy group having 3 to 20 C atoms, or a cyclic alkyl group having 3 to 20 C atoms, or a cyclic alkoxy group having 3 to 20 C atoms, or a cyclic thioalkoxy group having 3 to 20 C atoms, or a silyl group, or a keto group having 1 to 20 C atoms, or an alkoxycarbonyl group having 2 to 20 C atoms, or an aryloxycarbonyl group having 7 to 20 C atoms, a cyano group, a carbamoyl group, a halocarbonyl group, a formyl group, an isocyano group, an isocyanate group, a thiocyanate group, or an isothiocyanate group, a hydroxyl group, a nitro group, an amino group, CF3, Cl, Br, F, I, 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 heteroaryloxy group having 5 to 60 ring atoms, or a combination of these groups.

[0105] It is understood that in the present invention, when X2 is a linking site, X2 is C.

[0106] In a specific example, R 14 , R 15 , R 16 , R 17 Each occurrence is independently selected from: -H, -D, a straight-chain alkyl group having 1 to 4 C atoms, a branched-chain alkyl group having 3 to 4 C atoms, a substituted or unsubstituted aromatic group having 6 to 10 ring atoms, a substituted or unsubstituted heteroaromatic group having 5 to 10 ring atoms, or a combination of these groups.

[0107] The definition of the substituents is as described above.

[0108] In some preferred embodiments, L1 and L2 are independently selected from a single bond, or from one of the following groups:

[0109]

[0110] The structures of the organic compounds according to the present invention are listed below, but are not limited thereto:

[0111]

[0112]

[0113]

[0114]

[0115]

[0116]

[0117]

[0118] The organic compounds according to the present invention can be used as functional materials in the functional layers of electronic devices, especially in OLED devices. The functional materials can be classified into 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, and organic dyes.

[0119] In one embodiment, the organic compounds according to the present invention can be used as light-emitting materials in the light-emitting layer. Preferably, they can be used as the host material of the light-emitting layer in the light-emitting layer.

[0120] The present invention further relates to a mixture comprising at least one of the above-mentioned organic compounds and at least one other organic functional material, and the other organic functional material can be selected from hole injection materials (HIM), hole transport materials (HTM), electron transport materials (ETM), electron injection materials (EIM), electron blocking materials (EBM), hole blocking materials (HBM), light-emitting materials, host materials, and organic dyes.

[0121] In one embodiment, the other organic functional material is selected from guest materials; further, the other organic functional material is selected from blue light guest materials. Preferably, the blue light guest material is selected from pyrene-based organic compounds.

[0122] The present invention also relates to a composition comprising at least one of the above-mentioned organic compounds or mixtures and at least one organic solvent; the at least one organic solvent is selected from aromatic or heteroaromatic, esters, aromatic ketones or aromatic ethers, aliphatic ketones or aliphatic ethers, cycloaliphatic or olefinic compounds, or borate or phosphate compounds, or a mixture of two or more solvents.

[0123] Examples of aromatic or heteroaromatic solvents suitable for the present invention include, but are not limited to: p-diisopropylbenzene, pentylbenzene, tetralin, cyclohexylbenzene, chloronaphthalene, 1,4-dimethylnaphthalene, 3-isopropylbiphenyl, p-methylcumene, dipentylbenzene, tripentylbenzene, amyltoluene, o-diethylbenzene, m-diethylbenzene, p-diethylbenzene, 1,2,3,4-tetramethylbenzene, 1,2,3,5-tetramethylbenzene, 1,2,4,5-tetramethylbenzene, butylbenzene, dodecylbenzene, dihexylbenzene, dibutylbenzene, p-diisopropylbenzene, cyclohexylbenzene, benzyl butylbenzene, dimethylnaphthalene, 3-isopropylbiphenyl, p-methylcumene, 1-methylnaphthalene, 1,2,4-trichlorobenzene, 4,4-difluorodiphenylmethane, 1,2-dimethoxy-4-(1-propenyl)benzene, diphenylmethane, 2-phenylpyridine, 3-phenylpyridine, N-methyldiphenylamine, 4-isopropylbiphenyl, α,α-dichlorodiphenylmethane, 4-(3-phenylpropyl)pyridine, benzyl benzoate, 1,1-bis(3,4-dimethylphenyl)ethane, 2-isopropylnaphthalene, quinoline, isoquinoline, methyl 2-furoate, ethyl 2-furoate, etc.

[0124] Examples of aromatic ketone solvents suitable for the present invention include, but are not limited to: 1-tetralone, 2-tetralone, 2-(phenyloxiranyl)tetralone, 6-(methoxy)tetralone, acetophenone, propiophenone, benzophenone, and their derivatives such as 4-methylacetophenone, 3-methylacetophenone, 2-methylacetophenone, 4-methylpropiophenone, 3-methylpropiophenone, 2-methylpropiophenone, etc.

[0125] Examples of aromatic ether solvents suitable for the present invention include, but are not limited to: 3-phenoxytoluene, butoxybenzene, p-anisaldehyde dimethyl acetal, tetrahydro-2-phenoxy-2H-pyran, 1,2-dimethoxy-4-(1-propenyl)benzene, 1,4-benzodioxane, 1,3-dipropylbenzene, 2,5-dimethoxytoluene, 4-ethylbenzyl ethyl ether, 1,3-dipropoxybenzene, 1,2,4-trimethoxybenzene, 4-(1-propenyl)-1,2-dimethoxybenzene, 1,3-dimethoxybenzene, glycidyl phenyl ether, dibenzyl ether, 4-tert-butylanisole, trans-p-anisalacetophenone, 1,2-dimethoxybenzene, 1-methoxynaphthalene, diphenyl ether, 2-phenoxymethyl ether, 2-phenoxytetrahydrofuran, ethyl 2-naphthyl ether.

[0126] Examples of aliphatic ketone solvents suitable for the present invention include, but are not limited to: 2-nonanone, 3-nonanone, 5-nonanone, 2-decanone, 2,5-hexanedione, 2,6,8-trimethyl-4-nonanone, fenchone, phorone, isophorone, di-n-pentyl ketone, etc.; or aliphatic ethers, 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, tetraethylene glycol dimethyl ether, etc.

[0127] Examples of ester solvents suitable for the present invention include, but are not limited to: alkyl octanoates, alkyl sebacates, alkyl stearates, alkyl benzoates, alkyl phenylacetates, alkyl cinnamates, alkyl oxalates, alkyl maleates, alkanolactones, alkyl oleates, etc. Octyl octanoate, diethyl sebacate, diallyl phthalate, and isononyl isononanoate are particularly preferred.

[0128] The solvents described above can be used alone or as a mixture of two or more organic solvents.

[0129] In certain preferred embodiments, a composition according to the present invention comprises at least one organic compound or mixture as described above and at least one organic solvent, and may further comprise another organic solvent. Examples of another organic solvent include (but are not limited to): methanol, ethanol, 2-methoxyethanol, dichloromethane, chloroform, chlorobenzene, o-dichlorobenzene, tetrahydrofuran, anisole, morpholine, toluene, o-xylene, m-xylene, p-xylene, 1,4-dioxane, acetone, methyl ethyl ketone, 1,2-dichloroethane, 3-phenoxytoluene, 1,1,1-trichloroethane, 1,1,2,2-tetrachloroethane, ethyl acetate, butyl acetate, dimethylformamide, dimethylacetamide, dimethyl sulfoxide, tetralin, decalin, indene, and / or mixtures thereof.

[0130] In some preferred embodiments, solvents particularly suitable for the present invention are solvents having Hansen solubility parameters in the following ranges:

[0131] δd (dispersion force) ranges from 17.0 to 23.2 MPa1 / 2, especially from 18.5 to 21.0 MPa1 / 2;

[0132] δp (polar force) ranges from 0.2 to 12.5 MPa1 / 2, especially from 2.0 to 6.0 MPa1 / 2;

[0133] δh (hydrogen bonding force) ranges from 0.9 to 14.2 MPa1 / 2, especially from 2.0 to 6.0 MPa1 / 2.

[0134] A composition according to the present invention, wherein the organic solvent is selected considering its boiling point parameter. In the present invention, the boiling point of the organic solvent is ≥150 °C; preferably ≥180 °C; more preferably ≥200 °C; still more preferably ≥250 °C; most preferably ≥300 °C. Boiling points within these ranges are beneficial for preventing nozzle clogging of an inkjet print head. The organic solvent can evaporate from the solvent system to form a thin film containing the functional material.

[0135] In a preferred embodiment, the composition according to the present invention is a solution.

[0136] In another preferred embodiment, the composition according to the present invention is a suspension.

[0137] The composition in the examples of the present invention may include 0.01 wt% to 10 wt% of the compound or mixture according to the present invention, preferably 0.1 wt% to 8 wt%, more preferably 0.2 wt% to 5 wt%, and most preferably 0.25 wt% to 3 wt%.

[0138] The present invention also relates to the use of the composition as a coating or printing ink in the preparation of organic electronic devices, particularly preferably by a preparation method of printing or coating.

[0139] Among them, suitable printing or coating techniques include (but are not limited to) inkjet printing, letterpress printing, screen printing, dip coating, spin coating, knife coating, roller printing, reverse roll printing, lithographic printing, flexographic printing, rotary printing, spraying, brush coating or pad printing, slot die coating, etc. The preferred ones are gravure printing, inkjet printing and inkjet printing. The solution or suspension may additionally include one or more components such as surface active compounds, lubricants, wetting agents, dispersants, water repellents, adhesives, etc. for adjusting viscosity, film-forming properties, improving adhesion, etc. Regarding printing techniques and their related requirements for relevant solutions, such as solvents and concentrations, viscosities, etc.

[0140] The present invention also provides an application of the above-mentioned organic compound, mixture or composition in an organic electronic device. The technical solution is as follows:

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

[0142] In some preferred embodiments, the organic electronic device includes a first electrode, a second electrode, and one or more organic functional layers located between the first electrode and the second electrode. The organic functional layer contains the organic compound, mixture, or composition prepared from the above-mentioned components as described above. The functional layer is selected from a hole injection layer (HIL), a hole transport layer (HTL), a light-emitting layer (EML), an electron blocking layer (EBL), an electron injection layer (EIL), an electron transport layer (ETL), and a hole blocking layer (HBL).

[0143] In the present invention, the organic electronic device may be, but is not limited to, an organic light-emitting diode (OLED), an organic photovoltaic cell, an organic light-emitting battery, an organic field-effect transistor, an organic light-emitting field-effect transistor, an organic laser, an organic spintronic device, an organic sensor, and an organic plasmonic emission diode, etc. Particularly preferably, it is an OLED.

[0144] Furthermore, the present invention relates to an organic electronic device, which includes: a cathode, an anode, and one or more organic functional layers located between the cathode and the anode. The organic functional layer includes at least one light-emitting layer. The light-emitting layer material contains the organic compound having the structure shown in Formula (1) as described above, and the organic compound having the structure shown in Formula (3):

[0145]

[0146] Wherein:

[0147] Ar4 - Ar7 are independently selected from a substituted or unsubstituted aromatic group containing 6 to 60 ring atoms, a substituted or unsubstituted heteroaromatic group containing 6 to 60 ring atoms, or a combination of these groups;

[0148] R 18Each occurrence is independently selected from -H, -D, or a straight-chain alkyl group having 1 to 20 C atoms, or a straight-chain alkoxy group having 1 to 20 C atoms, or a straight-chain thioalkoxy group having 1 to 20 C atoms, or a branched-chain alkyl group having 3 to 20 C atoms, or a branched-chain alkoxy group having 3 to 20 C atoms, or a branched-chain thioalkoxy group having 3 to 20 C atoms, or a cyclic alkyl group having 3 to 20 C atoms, or a cyclic alkoxy group having 3 to 20 C atoms, or a cyclic thioalkoxy group having 3 to 20 C atoms, or a silyl group, or a keto group having 1 to 20 C atoms, or an alkoxycarbonyl group having 2 to 20 C atoms, or an aryloxycarbonyl group having 7 to 20 C atoms, a cyano group, a carbamoyl group, a halocarbonyl group, a formyl group, an isocyano group, an isocyanate group, a thiocyanate group, or an isothiocyanate group, a hydroxyl group, a nitro group, an amino group, -CF3, -Cl, -Br, -F, -I, 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 heteroaryloxy group having 5 to 60 ring atoms, or a combination of these groups;

[0149] s is selected from any integer from 0 to 8.

[0150] In the above-mentioned organic electronic device, the organic compound having the structure shown in formula (1) can be used as the host material of the light-emitting layer, and the organic compound having the structure shown in formula (3) can be used as the guest material of the light-emitting layer.

[0151] The further description of the organic compound having the structure shown in formula (1) is as described above.

[0152] In one embodiment, Ar4 - Ar7 are independently selected from a substituted or unsubstituted aromatic group containing 6 to 14 ring atoms, or a substituted or unsubstituted heteroaromatic group containing 6 to 14 ring atoms, or a combination of these groups.

[0153] In one embodiment, the aforementioned Ar4 - Ar7 includes any of the following structures:

[0154]

[0155] Wherein:

[0156] Each occurrence of V is independently selected from CR 19 or N;

[0157] W is selected from NR 20 , CR 20 R 21 , SiR 20 R 21 , O, S, S=O or SO2;

[0158] R 19 、R 20 、R 21 Each occurrence is independently selected from -H, -D, or a straight-chain alkyl group having 1 to 20 carbon atoms, or 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-chain alkyl group having 3 to 20 carbon atoms, or a branched-chain alkoxy group having 3 to 20 carbon atoms, or a branched-chain 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 keto group having 1 to 20 carbon atoms, or an alkoxycarbonyl group having 2 to 20 carbon atoms, or an aryloxycarbonyl group having 7 to 20 carbon atoms, cyano, carbamoyl, halocarbonyl, formyl, isocyano, isocyanate, thiocyanate, or isothiocyanate, hydroxy, nitro, amino, 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 heteroaryloxy group having 5 to 60 ring atoms, or a combination of these groups.

[0159] It should be noted that when V is a connection site, V is selected from C.

[0160] Furthermore, R 19 -R 21 Each occurrence is independently selected from -H, -D, or a straight-chain alkyl group having 1 to 10 carbon atoms, or a branched-chain alkyl group having 3 to 10 carbon atoms, or a cyclic alkyl group having 3 to 10 carbon atoms, or a substituted or unsubstituted aromatic group having 6 to 30 ring atoms, or a substituted or unsubstituted heteroaromatic group having 5 to 30 ring atoms, or a combination of these groups.

[0161] Furthermore, R 19 -R 21 Each occurrence is independently selected from -H, -D, a straight-chain alkyl group having 1 to 10 carbon atoms, or a branched-chain alkyl group or cyclic alkyl group or phenyl group having 3 to 10 carbon atoms.

[0162] In one embodiment, formula (3) is selected from the following general formulas:

[0163]

[0164] Preferably, R 19Each occurrence is independently selected from -H, -D, a straight-chain alkyl group having 1 to 10 C atoms, or a branched-chain alkyl group, a cyclic alkyl group, or a phenyl group having 3 to 10 C atoms.

[0165] Furthermore, formula (3) is selected from the following general formulas:

[0166]

[0167] Wherein: W has the same meaning as described above.

[0168] The structures of the organic compounds according to formula (3) of the present invention are listed below, but are not limited thereto:

[0169]

[0170]

[0171] 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.

[0172] 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.

[0173] The materials suitable for use in these functional layers are described in detail above and in WO2010135519A1, US20090134784A1, and WO2011110277A1, and the entire contents of these three patent documents are hereby incorporated herein by reference.

[0174] In the light-emitting device described above, particularly in an OLED, it includes a substrate, an anode, at least one light-emitting layer, and a cathode.

[0175] The substrate can be opaque or transparent. A transparent substrate can be used to fabricate a transparent light-emitting component. For example, see Bulovic et al., Nature 1996, 380, p29, and Gu et al., Appl. Phys. Lett. 1996, 68, p2606. The substrate can be rigid or flexible. The substrate can be plastic, metal, semiconductor wafer, or glass. Preferably, the substrate has a smooth surface. A substrate without surface defects is a particularly ideal choice. In a preferred embodiment, the substrate is flexible and can be selected from polymer films or plastics having a glass transition temperature Tg of 150 °C or higher, preferably exceeding 200 °C, more preferably exceeding 250 °C, and most preferably exceeding 300 °C. Examples of suitable flexible substrates include poly(ethylene terephthalate) (PET) and poly(ethylene 2,6-naphthalate) (PEN).

[0176] The anode may include a conductive metal or metal oxide, or a conductive polymer. The anode can easily inject holes into the hole injection layer (HIL), hole transport layer (HTL), or light-emitting layer. In one embodiment, the absolute value of the difference between the work function of the anode and the HOMO level or valence band level of the light-emitting body in the light-emitting layer or the p-type semiconductor material serving as the HIL, HTL, or electron blocking layer (EBL) is less than 0.5 eV, preferably less than 0.3 eV, and most preferably less than 0.2 eV. Examples of anode materials include, but are not limited to: Al, Cu, Au, Ag, Mg, Fe, Co, Ni, Mn, Pd, Pt, ITO, aluminum-doped zinc oxide (AZO), etc. Other suitable anode materials are known, and those of ordinary skill in the art can easily select and use them. The anode material can be deposited using any suitable technique, such as a suitable physical vapor deposition method, including radio frequency magnetron sputtering, vacuum thermal evaporation, electron beam (e-beam), etc. In some embodiments, the anode is pattern-structured. Patterned ITO conductive substrates are commercially available and can be used to fabricate the devices according to the present invention.

[0177] The cathode may include a conductive metal or metal oxide. The cathode can easily inject electrons into the EIL, ETL, or directly into the light-emitting layer. In one embodiment, the absolute value of the difference between the work function of the cathode and the LUMO level or conduction band level of the light-emitting body in the light-emitting layer or the n-type semiconductor material serving as the electron injection layer (EIL), electron transport layer (ETL), or hole blocking layer (HBL) is less than 0.5 eV, preferably less than 0.3 eV, and most preferably less than 0.2 eV. In principle, all materials that can be used as the cathode of an OLED can potentially be used as the cathode material of the devices of the present invention. Examples of cathode materials include, but are not limited to: Al, Au, Ag, Ca, Ba, Mg, LiF / Al, MgAg alloy, BaF2 / Al, Cu, Fe, Co, Ni, Mn, Pd, Pt, ITO, etc. The cathode material can be deposited using any suitable technique, such as a suitable physical vapor deposition method, including radio frequency magnetron sputtering, vacuum thermal evaporation, electron beam (e-beam), etc.

[0178] The material of the hole transport layer is a material known in the art for hole transport layers. For example, it can be selected from, but not limited to, poly[bis(4-phenyl)(2,4,6-trimethylphenyl)amine] (PTXX), 2,2',7,7'-tetrakis[N,N-bis(4-methoxyphenyl)amino]-9,9'-spirobifluorene (spiro-omeTXD), 4,4'-cyclohexylidenebis[N,N-bis(4-methylphenyl)aniline] (TXPC), N,N'-bis(1-naphthyl)-N,N'-diphenyl-1,1'-biphenyl-4,4'-diamine (NPB), 4,4'-bis(N-carbazolyl)-1,1'-biphenyl (CBP), poly[(9,9-dioctylfluorenyl-2,7-diyl)-co-(4,4'-(N-(p-butylphenyl))diphenylamine)] (TFB), poly(9-vinylcarbazole) (PVK), poly(triphenylamine) (Poly-TPD), poly(3,4-ethylenedioxythiophene)-poly(styrenesulfonic acid) (PEDOT:PSS), and 4,4',4''-tris(carbazol-9-yl)triphenylamine (TCTX), etc., at least one of them.

[0179] The material of the electron transport layer is a material known in the art for electron transport layers. For example, it can be selected from, but not limited to, ET and Liq, PBD (2-(4-biphenylyl)-5-phenyloxadiazole), tris(8-hydroxyquinoline)aluminum (Xlq3), and graphene, etc., at least one of them.

[0180] Among them, the chemical structural formulas of ET and Liq are as follows:

[0181]

[0182] The material of the hole injection layer is a material known in the art for hole injection layers. For example, it can be selected from, but not limited to, 2,3,6,7,10,11-hexacyano-1,4,5,8,9,12-hexaazatriphenylene (HXT-CN), PEDOT (polyethylenedioxythiophene), PEDOT:PSS, and its derivative doped with s-MoO3 (PEDOT:PSS:s-MoO3), etc., at least one of them.

[0183] In a preferred embodiment, the organic electronic device according to the present invention is selected from solution-based OLEDs.

[0184] In a preferred embodiment, in the light-emitting device according to the present invention, its light-emitting layer is prepared from the composition according to the present invention.

[0185] For the light-emitting device according to the present invention, its emission wavelength is between 300 and 1000 nm, preferably between 350 and 900 nm, and more preferably between 400 and 800 nm.

[0186] The present invention also relates to the use of the organic electronic device according to the present invention in various electronic devices, including, but not limited to, display devices, lighting devices, light sources, sensors and the like.

[0187] The present invention also relates to an electronic device comprising the organic electronic device according to the present invention, including, but not limited to, display devices, lighting devices, light sources, sensors and the like.

[0188] The present invention will be described below in conjunction with preferred embodiments, but the present invention is not limited to the following embodiments. It should be understood that the appended claims define the scope of the present invention. Under the guidance of the inventive concept, those skilled in the art should realize that certain changes made to the embodiments of the present invention will be covered by the spirit and scope of the claims of the present invention. Specific Embodiments

[0190] 1. Synthesis of Compounds

[0191] Synthesis of Compound 1 in Example 1

[0192]

[0193] Synthesis of Intermediate 1-1:

[0194] Dissolve 1,9-dibromodibenzofuran (10 g, 31 mmol) and phenylboronic acid (3.8 g, 31 mmol) in a mixed solvent of 1,4-dioxane and water (1000 / 10 ml), and add Pd(PPh3)4 (1.8 g, 1.5 mmol) and potassium carbonate (21 g, 154 mmol). Stir at 100 °C for 12 h under a nitrogen atmosphere. After cooling, most of the solvent was removed by rotary evaporation, and then extracted and washed with water for liquid separation. The organic phase was subjected to column chromatography (eluent: PE) to obtain a white solid with a yield of 66%. MS(ASAP) = 322.0

[0195] Synthesis of Intermediate 1-2:

[0196] Prepare a dry 250 mL three-necked flask, set up the reaction device, evacuate and introduce nitrogen; keep the nitrogen flowing in the reaction flask, weigh 1-1 (5.0 g, 16 mmol), and add THF (100 ml), evacuate and introduce nitrogen three times in a cycle, cool down to -78 °C; slowly add n-butyllithium solution (6.2 ml, 16 mmol) to the reaction flask, react at -78 °C for 60 min, and then quickly add benzophenone (3.4 g, 19 mmol). Let the reaction system slowly rise to room temperature and react for 12 h. Add water, extract with DCM, after evaporating the solvent, triturate with PE to obtain a white solid. The yield is 43%. MS(ASAP) = 426.2

[0197] Synthesis of Intermediate 1-3:

[0198] Place intermediate 1-2 (5 g, 12 mmol) in a 100-ml two-necked flask, add 20 ml of H2SO4 until all the solid is dissolved, and stir at 100 °C for 12 h. After the reaction is completed, the reaction solution is slowly poured into ice water, extracted with DCM, the organic layer is collected, washed with water, and column chromatography (eluent: PE) gives a white solid with a yield of 49%. MS (ASAP) = 408.2

[0199] Synthesis of intermediate 1-4:

[0200] Place intermediate 1-3 (5 g, 12.3 mmol) in a 250-ml two-necked flask, add 100 ml of DMF until all the solid is dissolved, weigh NBS (2.2 g, 12.3 mmol) and place it in a constant-pressure dropping funnel, dissolve it with 20 ml of DMF, slowly add dropwise, and react at room temperature for 12 h. Rotavapor to dryness, wash with water, and column chromatography (eluent: PE) gives a white solid with a yield of 85%. MS (ASAP) = 486.1

[0201] Synthesis of intermediate 1-5:

[0202] Weigh 1-4 (5 g, 10.3 mmol), (Bpin)2 (3.1 g, 12.3 mmol), AcOK (9.8 g, 100 mmol), and Pd(dppf)Cl2 (0.74 g, 1.0 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. Rotavapor to dryness, wash with water, and column chromatography (eluent: PE:DCM = 5:1) gives a colorless oily substance with a yield of 73%. MS (ASAP) = 534.2

[0203] Synthesis of compound 1:

[0204] Dissolve intermediate 1-5 (4 g, 7.5 mmol) and 9-bromo-10-(1-naphthyl)anthracene (3.4 g, 9.0 mmol) in a mixed solvent of 1,4-dioxane and water (100 / 10 ml), and add Pd(PPh3)4 (0.87 g, 0.75 mmol) and potassium carbonate (5.2 g, 38 mmol). Stir at 100 °C for 12 h under a nitrogen atmosphere. After cooling, most of the solvent is removed by rotary evaporation, then extracted and washed and separated by liquid separation. The organic phase is subjected to column chromatography (eluent: PE) and recrystallization to obtain compound 1 with a yield of 58%. MS (ASAP) = 710.3

[0205] Synthesis of compound 2 in Example 2

[0206]

[0207] Synthesis of Intermediate 2-1:

[0208] Dissolve intermediate 9-bromo-10-(1-naphthyl)anthracene (3.8 g, 10 mmol) and 4'-bromo-4-biphenylboronic acid (2.7 g, 10 mmol) in a mixed solvent of 1,4-dioxane and water (100 / 10 ml), and add Pd(PPh3)4 (1.15 g, 1 mmol) and potassium carbonate (4.1 g, 30 mmol). Stir at 100 °C for 12 h under a nitrogen atmosphere. After cooling, most of the solvent is removed by rotary evaporation, and then extraction and washing with water for liquid separation are carried out. The organic phase is subjected to column chromatography and recrystallization to obtain intermediate 2-1, yield: 88%. MS(ASAP)=534.1

[0209] Synthesis of Compound 2:

[0210] Dissolve intermediate 2-1 (5.3 g, 10 mmol) and 1-5 (5.3 g, 10 mmol) in a mixed solvent of 1,4-dioxane and water (100 / 10 ml), and add Pd(PPh3)4 (1.15 g, 1 mmol) and potassium carbonate (4.1 g, 30 mmol). Stir at 100 °C for 12 h under a nitrogen atmosphere. After cooling, most of the solvent is removed by rotary evaporation, and then extraction and washing with water for liquid separation are carried out. The organic phase is subjected to column chromatography and recrystallization to obtain compound 2, yield: 73%. MS(ASAP)=862.3

[0211] Synthesis of Compound 3 in Example 3

[0212]

[0213] Synthesis of Intermediate 3-1:

[0214] Dissolve intermediate 9-bromo-10-(1-naphthyl)anthracene (3.8 g, 10 mmol) and 4-bromo-1-naphthaleneboronic acid (2.5 g, 10 mmol) in a mixed solvent of 1,4-dioxane and water (100 / 10 ml), and add Pd(PPh3)4 (1.15 g, 1 mmol) and potassium carbonate (4.1 g, 30 mmol). Stir at 100 °C for 12 h under a nitrogen atmosphere. After cooling, most of the solvent is removed by rotary evaporation, and then extraction and washing with water for liquid separation are carried out. The organic phase is subjected to column chromatography and recrystallization to obtain intermediate 3-1, yield: 82%. MS(ASAP)=508.1

[0215] Synthesis of Compound 3:

[0216] Dissolve intermediate 3-1 (5.1 g, 10 mmol) and 1-5 (5.3 g, 10 mmol) in a mixed solvent of 1,4-dioxane and water (100 / 10 ml), and add Pd(PPh3)4 (1.15 g, 1 mmol) and potassium carbonate (4.1 g, 30 mmol). Stir at 100 °C for 12 h under a nitrogen atmosphere. After cooling, most of the solvent was removed by rotary evaporation, and then extracted, washed with water and separated by liquid separation. The organic phase was purified by column chromatography and recrystallized to obtain compound 3, yield: 79%. MS(ASAP)=836.3

[0217] Synthesis of Compound 4 in Example 4

[0218]

[0219] Synthesis of Intermediate 4-1:

[0220] Dissolve intermediate 9,10-dibromoanthracene (3.4 g, 10 mmol) and deuterated 1-naphthaleneboronic acid (1.8 g, 10 mmol) in a mixed solvent of 1,4-dioxane and water (100 / 10 ml), and add Pd(PPh3)4 (1.15 g, 1 mmol) and potassium carbonate (4.1 g, 30 mmol). Stir at 100 °C for 12 h under a nitrogen atmosphere. After cooling, most of the solvent was removed by rotary evaporation, and then extracted, washed with water and separated by liquid separation. The organic phase was purified by column chromatography and recrystallized to obtain intermediate 4-1, yield: 63%. MS(ASAP)=389.1

[0221] Synthesis of Compound 4:

[0222] Dissolve intermediate 4-1 (3.9 g, 10 mmol) and 1-5 (5.3 g, 10 mmol) in a mixed solvent of 1,4-dioxane and water (100 / 10 ml), and add Pd(PPh3)4 (1.15 g, 1 mmol) and potassium carbonate (4.1 g, 30 mmol). Stir at 100 °C for 12 h under a nitrogen atmosphere. After cooling, most of the solvent was removed by rotary evaporation, and then extracted, washed with water and separated by liquid separation. The organic phase was purified by column chromatography and recrystallized to obtain compound 4, yield: 63%. MS(ASAP)=717.3

[0223] Synthesis of Compound 5 in Example 5

[0224]

[0225] Synthesis of Intermediate 5-1:

[0226] Dissolve the intermediate 9-bromo-10-(phenyl)anthracene (3.3 g, 10 mmol) and 10-bromo-9-anthraceneboronic acid (3.0 g, 10 mmol) in a mixed solvent of 1,4-dioxane and water (100 / 10 ml), and add Pd(PPh3)4 (1.15 g, 1 mmol) and potassium carbonate (4.1 g, 30 mmol). Stir at 100 °C for 12 h under a nitrogen atmosphere. After cooling, most of the solvent is removed by rotary evaporation, and then extraction and washing with water are carried out for liquid separation. The organic phase is subjected to column chromatography and recrystallization to obtain the intermediate 5-1, yield: 61%. MS(ASAP)=558.1

[0227] Synthesis of Compound 5:

[0228] Dissolve the intermediate 5-1 (5.1 g, 10 mmol) and 1-5 (5.3 g, 10 mmol) in a mixed solvent of 1,4-dioxane and water (100 / 10 ml), and add Pd(PPh3)4 (1.15 g, 1 mmol) and potassium carbonate (4.1 g, 30 mmol). Stir at 100 °C for 12 h under a nitrogen atmosphere. After cooling, most of the solvent is removed by rotary evaporation, and then extraction and washing with water are carried out for liquid separation. The organic phase is subjected to column chromatography and recrystallization to obtain Compound 5, yield: 55%. MS(ASAP)=836.3

[0229] Synthesis of Compound 6 in Example 6

[0230]

[0231] Synthesis of Intermediate 6-1:

[0232] Dissolve the intermediate 9-bromo-10-(1-naphthyl)anthracene (3.8 g, 10 mmol) and 10-(4-bromo-1-naphthyl)-9-anthraceneboronic acid (4.3 g, 10 mmol) in a mixed solvent of 1,4-dioxane and water (100 / 10 ml), and add Pd(PPh3)4 (1.15 g, 1 mmol) and potassium carbonate (4.1 g, 30 mmol). Stir at 100 °C for 12 h under a nitrogen atmosphere. After cooling, most of the solvent is removed by rotary evaporation, and then extraction and washing with water are carried out for liquid separation. The organic phase is subjected to column chromatography and recrystallization to obtain the intermediate 6-1, yield: 64%. MS(ASAP)=684.2

[0233] Synthesis of Compound 6:

[0234] Intermediate 6-1 (6.8 g, 10 mmol) and 1-5 (5.3 g, 10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (100 / 10 ml), and Pd(PPh3)4 (1.15 g, 1 mmol) and potassium carbonate (4.1 g, 30 mmol) were added. Under a nitrogen atmosphere, the mixture was stirred at 100 °C for 12 h. After cooling, most of the solvent was removed by rotary evaporation, and then the mixture was extracted, washed with water, and separated by liquid-liquid extraction. The organic phase was purified by column chromatography and recrystallization to obtain Compound 6, yield: 43%. MS (ASAP) = 1012.4

[0235] Synthesis of Compound 7 in Example 7

[0236]

[0237] Synthesis of Intermediate 7-1:

[0238] Intermediate 9-bromo-10-(1-naphthyl)anthracene (3.8 g, 10 mmol) and 2,3,5,6-tetramethyl-4-bromobenzeneboronic acid (2.6 g, 10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (100 / 10 ml), and Pd(PPh3)4 (1.15 g, 1 mmol) and potassium carbonate (4.1 g, 30 mmol) were added. Under a nitrogen atmosphere, the mixture was stirred at 100 °C for 12 h. After cooling, most of the solvent was removed by rotary evaporation, and then the mixture was extracted, washed with water, and separated by liquid-liquid extraction. The organic phase was purified by column chromatography and recrystallization to obtain Intermediate 7-1, yield: 44%. MS (ASAP) = 514.1

[0239] Synthesis of Compound 7:

[0240] Intermediate 7-1 (5.1 g, 10 mmol) and 1-5 (5.3 g, 10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (100 / 10 ml), and Pd(PPh3)4 (1.15 g, 1 mmol) and potassium carbonate (4.1 g, 30 mmol) were added. Under a nitrogen atmosphere, the mixture was stirred at 100 °C for 12 h. After cooling, most of the solvent was removed by rotary evaporation, and then the mixture was extracted, washed with water, and separated by liquid-liquid extraction. The organic phase was purified by column chromatography and recrystallization to obtain Compound 7, yield: 48%. MS (ASAP) = 842.4

[0241] Synthesis of Compound 8 in Example 8

[0242]

[0243] Synthesis of Intermediate 8-1:

[0244] Dissolve the intermediate 9-bromo-10-(phenyl)anthracene (3.3 g, 10 mmol) and 3-(10-bromo-9-anthryl)-phenylboronic acid (3.8 g, 10 mmol) in a mixed solvent of 1,4-dioxane and water (100 / 10 ml), and add Pd(PPh3)4 (1.15 g, 1 mmol) and potassium carbonate (4.1 g, 30 mmol). Stir at 100 °C for 12 h under a nitrogen atmosphere. After cooling, most of the solvent was removed by rotary evaporation, then extracted, washed with water and separated by liquid-liquid extraction. The organic phase was purified by column chromatography and recrystallized to obtain intermediate 8-1, yield: 49%. MS(ASAP)=584.1

[0245] Synthesis of Compound 8:

[0246] Dissolve the intermediate 8-1 (5.8 g, 10 mmol) and 1-5 (5.3 g, 10 mmol) in a mixed solvent of 1,4-dioxane and water (100 / 10 ml), and add Pd(PPh3)4 (1.15 g, 1 mmol) and potassium carbonate (4.1 g, 30 mmol). Stir at 100 °C for 12 h under a nitrogen atmosphere. After cooling, most of the solvent was removed by rotary evaporation, then extracted, washed with water and separated by liquid-liquid extraction. The organic phase was purified by column chromatography and recrystallized to obtain Compound 8, yield: 38%. MS(ASAP)=912.3

[0247] Synthesis of Compound 9 in Example 9

[0248]

[0249] Synthesis of Intermediate 9-1:

[0250] Dissolve the intermediate 9-bromo-10-(1-naphthyl)anthracene (3.8 g, 10 mmol) and 2-methyl-4-bromo-naphthaleneboronic acid (2.6 g, 10 mmol) in a mixed solvent of 1,4-dioxane and water (100 / 10 ml), and add Pd(PPh3)4 (1.15 g, 1 mmol) and potassium carbonate (4.1 g, 30 mmol). Stir at 100 °C for 12 h under a nitrogen atmosphere. After cooling, most of the solvent was removed by rotary evaporation, then extracted, washed with water and separated by liquid-liquid extraction. The organic phase was purified by column chromatography and recrystallized to obtain intermediate 9-1, yield: 77%. MS(ASAP)=522.1

[0251] Synthesis of Compound 9:

[0252] Dissolve intermediate 9-1 (5.2 g, 10 mmol) and 1-5 (5.3 g, 10 mmol) in a mixed solvent of 1,4-dioxane and water (100 / 10 ml), and add Pd(PPh3)4 (1.15 g, 1 mmol) and potassium carbonate (4.1 g, 30 mmol). Stir at 100 °C for 12 h under a nitrogen atmosphere. After cooling, most of the solvent was removed by rotary evaporation, then extracted, washed with water and separated by liquid separation. The organic phase was purified by column chromatography and recrystallized to obtain compound 9, yield: 52%. MS(ASAP)=850.3

[0253] Synthesis of Compound 10 in Example 10

[0254]

[0255] Synthesis of Intermediate 10-1:

[0256] Dissolve intermediate 9,10-dibromoanthracene (3.3 g, 10 mmol) and deuterated phenylboronic acid (1.3 g, 10 mmol) in a mixed solvent of 1,4-dioxane and water (100 / 10 ml), and add Pd(PPh3)4 (1.15 g, 1 mmol) and potassium carbonate (4.1 g, 30 mmol). Stir at 100 °C for 12 h under a nitrogen atmosphere. After cooling, most of the solvent was removed by rotary evaporation, then extracted, washed with water and separated by liquid separation. The organic phase was purified by column chromatography and recrystallized to obtain intermediate 10-1, yield: 82%. MS(ASAP)=337.1

[0257] Synthesis of Compound 10:

[0258] Dissolve intermediate 10-1 (3.4 g, 10 mmol) and 1-5 (5.3 g, 10 mmol) in a mixed solvent of 1,4-dioxane and water (100 / 10 ml), and add Pd(PPh3)4 (1.15 g, 1 mmol) and potassium carbonate (4.1 g, 30 mmol). Stir at 100 °C for 12 h under a nitrogen atmosphere. After cooling, most of the solvent was removed by rotary evaporation, then extracted, washed with water and separated by liquid separation. The organic phase was purified by column chromatography and recrystallized to obtain compound 10, yield: 51%. MS(ASAP)=665.3

[0259] Synthesis of Compound 11 in Example 11

[0260]

[0261] Synthesis of Intermediate 11-1:

[0262] Prepare a dry 250 mL three-necked flask, set up the reaction apparatus, evacuate it, and then introduce nitrogen. Keep the nitrogen flowing in the reaction flask. Weigh 1-1 (5.0 g, 16 mmol), add THF (100 mL), evacuate and introduce nitrogen three times in a cycle, and cool down to -78 °C. Slowly drip the n-butyllithium solution (6.2 mL, 16 mmol) into the reaction flask. After reacting at -78 °C for 60 min, quickly add 2-benzoylnaphthalene (3.4 g, 19 mmol). Let the reaction system slowly warm up to room temperature and react for 12 h. Add water, extract with DCM. After rotary evaporation of the solvent, triturate with PE to obtain a white solid. The yield is 43%. MS (ASAP) = 476.2

[0263] Synthesis of Intermediate 11-2:

[0264] Place Intermediate 11-1 (4.8 g, 10 mmol) in a 100 mL two-necked flask, add 20 mL of H2SO4 until the solid completely dissolves, and stir at 100 °C for 12 h. After the reaction is completed, slowly pour the reaction solution into ice water, extract with DCM, collect the organic layer, wash it with water, and perform column chromatography (the eluent is PE) to obtain a white solid. The yield is 33%. MS (ASAP) = 458.2

[0265] Synthesis of Intermediate 11-3:

[0266] Place Intermediate 11-2 (5 g, 10.9 mmol) in a 250 mL two-necked flask, add 100 mL of DMF until the solid completely dissolves. Weigh NBS (1.9 g, 10.9 mmol) and place it in a constant pressure dropping funnel, dissolve it with 20 mL of DMF, slowly drip it in, and react at room temperature for 12 h. Rotary evaporate, wash with water, and perform column chromatography (the eluent is PE) to obtain a white solid. The yield is 78%. MS (ASAP) = 536.1

[0267] Synthesis of Intermediate 11-4:

[0268] Weigh 11-3 (5 g, 9.3 mmol), (Bpin)2 (2.8 g, 11.1 mmol), AcOK (9.1 g, 93 mmol), and Pd(dppf)Cl2 (0.68 g, 0.93 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. Rotary evaporate, wash with water, and perform column chromatography (the eluent is PE:DCM = 3:1) to obtain a colorless oil. The yield is 63%. MS (ASAP) = 584.3

[0269] Synthesis of Compound 11:

[0270] Intermediate 11-4 (3 g, 5.1 mmol) and 9-bromo-10-(1-naphthyl)anthracene (2.4 g, 6.2 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (100 / 10 ml), and Pd(PPh3)4 (0.59 g, 0.51 mmol) and potassium carbonate (7.0 g, 51 mmol) were added. Under a nitrogen atmosphere, the mixture was stirred at 100 °C for 12 h. After cooling, most of the solvent was removed by rotary evaporation, and then the mixture was extracted, washed with water, and separated by liquid separation. The organic phase was subjected to column chromatography (eluent: PE) and recrystallization to obtain Compound 11, yield: 53%. MS (ASAP) = 760.3

[0271] Synthesis of Compound 12 in Example 12

[0272]

[0273] Synthesis of Intermediate 12-1:

[0274] A dry 250 mL three-necked flask was prepared, the reaction apparatus was set up, evacuated, and filled with nitrogen; nitrogen was kept flowing in the reaction flask. 1-1 (5.0 g, 16 mmol) was weighed and THF (100 ml) was added. The mixture was evacuated and filled with nitrogen three times, and the temperature was lowered to -78 °C; n-butyllithium solution (6.2 ml, 16 mmol) was slowly added dropwise to the reaction flask. After reacting at -78 °C for 60 min, 4-phenyldiphenyl ketone (4.8 g, 19 mmol) was quickly added. The reaction system was slowly warmed to room temperature and reacted for 12 h. Water was added, and the mixture was extracted with DCM. After the solvent was evaporated to dryness, it was slurried with PE to obtain a white solid. Yield 58%. MS (ASAP) = 502.2

[0275] Synthesis of Intermediate 12-2:

[0276] Intermediate 12-1 (4 g, 8.7 mmol) was placed in a 100 ml two-necked flask, and 20 ml of H2SO4 was added until the solid was completely dissolved. The mixture was stirred at 100 °C for 12 h. After the reaction was completed, the reaction solution was slowly poured into ice water, extracted with DCM, the organic layer was collected, washed with water, and column chromatography (eluent: PE) was performed to obtain a white solid, yield 33%. MS (ASAP) = 484.2

[0277] Synthesis of Intermediate 12-3:

[0278] Intermediate 12-2 (5 g, 10.3 mmol) was placed in a 250 mL two-necked flask, and 100 mL of DMF was added until the solid was completely dissolved. NBS (1.8 g, 10.3 mmol) was weighed and placed in a constant-pressure dropping funnel, dissolved in 20 mL of DMF, and slowly added dropwise. The reaction was carried out at room temperature for 12 h. The solvent was evaporated under reduced pressure, washed with water, and column chromatography (eluent: PE) was used to obtain a white solid with a yield of 72%. MS (ASAP) = 562.1

[0279] Synthesis of Intermediate 12-4:

[0280] 12-3 (5 g, 8.9 mmol), (Bpin)2 (2.7 g, 10.7 mmol), AcOK (8.7 g, 89 mmol), and Pd(dppf)Cl2 (0.65 g, 0.89 mmol) were weighed and placed in a 250 mL three-necked flask. 100 mL of 1,4-dioxane was added, the nitrogen was displaced, and the reaction was carried out at 100 °C for 12 h. The solvent was evaporated under reduced pressure, washed with water, and column chromatography (eluent: PE:DCM = 3:1) was used to obtain a colorless oily substance with a yield of 58%. MS (ASAP) = 610.3

[0281] Synthesis of Compound 12:

[0282] Intermediate 12-4 (5 g, 8.2 mmol) and 9-bromo-10-(1-naphthyl)anthracene (3.8 g, 9.8 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (100 / 10 mL), and Pd(PPh3)4 (0.95 g, 0.82 mmol) and potassium carbonate (5.6 g, 41 mmol) were added. Under a nitrogen atmosphere, the mixture was stirred at 100 °C for 12 h. After cooling, most of the solvent was removed by rotary evaporation, and then extraction and washing with water were carried out for liquid separation. The organic phase was subjected to column chromatography (eluent: PE) and recrystallization to obtain Compound 12 with a yield of 51%. MS (ASAP) = 786.3

[0283] Synthesis of Compound 13 in Example 13

[0284]

[0285] Synthesis of Intermediate 13-1:

[0286] Prepare a dry 250 mL three-necked flask, set up the reaction apparatus, evacuate it, and then introduce nitrogen. Keep the nitrogen flowing in the reaction flask. Weigh 1-1 (5.0 g, 16 mmol), add THF (100 mL), evacuate and introduce nitrogen three times in a cycle, and cool down to -78 °C. Slowly drip the n-butyllithium solution (6.2 mL, 16 mmol) into the reaction flask. After reacting at -78 °C for 60 min, quickly add 4,4'-di-tert-butylbenzophenone (5.5 g, 19 mmol). Let the reaction system slowly warm up to room temperature and react for 12 h. Add water, extract with DCM. After rotary evaporation of the solvent, triturate with PE to obtain a white solid. The yield is 51%. MS (ASAP) = 538.3

[0287] Synthesis of Intermediate 13-2:

[0288] Place Intermediate 13-1 (5 g, 9.3 mmol) in a 100 mL two-necked flask, add 20 mL of H2SO4 until all the solid is dissolved, and stir at 100 °C for 12 h. After the reaction is completed, slowly pour the reaction solution into ice water, extract with DCM, collect the organic layer, wash it with water, and perform column chromatography (the eluent is PE) to obtain a white solid. The yield is 42%. MS (ASAP) = 520.3

[0289] Synthesis of Intermediate 13-3:

[0290] Place Intermediate 13-2 (5 g, 9.6 mmol) in a 250 mL two-necked flask, add 100 mL of DMF until all the solid is dissolved. Weigh NBS (1.7 g, 9.6 mmol) and place it in a constant-pressure dropping funnel, dissolve it with 20 mL of DMF, slowly drip it, and react at room temperature for 12 h. Rotary evaporate, wash with water, and perform column chromatography (the eluent is PE) to obtain a white solid. The yield is 66%. MS (ASAP) = 598.2

[0291] Synthesis of Intermediate 13-4:

[0292] Weigh 13-3 (5 g, 8.4 mmol), (Bpin)2 (2.6 g, 10.0 mmol), AcOK (8.2 g, 84 mmol), Pd(dppf)Cl2 (0.61 g, 0.84 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. Rotary evaporate, wash with water, and perform column chromatography (the eluent is PE:DCM = 3:1) to obtain a colorless oily substance. The yield is 54%. MS (ASAP) = 646.4

[0293] Synthesis of Compound 13:

[0294] Intermediate 13-4 (5 g, 7.7 mmol) and 9-bromo-10-(1-naphthyl)anthracene (3.5 g, 9.3 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (100 / 10 ml), and Pd(PPh3)4 (0.89 g, 0.77 mmol) and potassium carbonate (5.3 g, 39 mmol) were added. Under a nitrogen atmosphere, the mixture was stirred at 100 °C for 12 h. After cooling, most of the solvent was removed by rotary evaporation, and then the mixture was extracted, washed with water, and separated by liquid-liquid extraction. The organic phase was purified by column chromatography (eluent: PE) and recrystallized to obtain Compound 13, yield: 59%. MS (ASAP) = 822.4

[0295] Synthesis of Compound 14 in Example 14

[0296]

[0297] Synthesis of Intermediate 14-1:

[0298] Intermediate 9-bromo-10-(1-naphthyl)anthracene (3.8 g, 10 mmol) and 2-bromopyridine-5-boronic acid (2.1 g, 10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (100 / 10 ml), and Pd(PPh3)4 (1.15 g, 1 mmol) and potassium carbonate (4.1 g, 30 mmol) were added. Under a nitrogen atmosphere, the mixture was stirred at 100 °C for 12 h. After cooling, most of the solvent was removed by rotary evaporation, and then the mixture was extracted, washed with water, and separated by liquid-liquid extraction. The organic phase was purified by column chromatography and recrystallized to obtain Intermediate 14-1, yield: 92%. MS (ASAP) = 459.1

[0299] Synthesis of Compound 14:

[0300] Intermediate 14-1 (4.6 g, 10 mmol) and 13-4 (6.5 g, 10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (100 / 10 ml), and Pd(PPh3)4 (1.15 g, 1 mmol) and potassium carbonate (4.1 g, 30 mmol) were added. Under a nitrogen atmosphere, the mixture was stirred at 100 °C for 12 h. After cooling, most of the solvent was removed by rotary evaporation, and then the mixture was extracted, washed with water, and separated by liquid-liquid extraction. The organic phase was purified by column chromatography and recrystallized to obtain Compound 14, yield: 74%. MS (ASAP) = 899.4

[0301] Synthesis of Compound 15 in Example 15

[0302]

[0303] Synthesis of Intermediate 15-1:

[0304] Dissolve intermediate 9,10-dibromoanthracene (10 g, 30 mmol) and dibenzo[b,d]furan-2-boronic acid (6.3 g, 30 mmol) in a mixed solvent of 1,4-dioxane and water (100 / 10 ml), and add Pd(PPh3)4 (1.7 g, 1.5 mmol) and potassium carbonate (20.7 g, 150 mmol). Stir at 100 °C for 12 h under a nitrogen atmosphere. After cooling, most of the solvent is removed by rotary evaporation, and then extraction, washing, and liquid separation are carried out. The organic phase is subjected to column chromatography and recrystallization to obtain intermediate 15-1, yield: 95%. MS(ASAP)=422.0

[0305] Synthesis of compound 15:

[0306] Dissolve intermediate 15-1 (4.2 g, 10 mmol) and 13-4 (6.5 g, 10 mmol) in a mixed solvent of 1,4-dioxane and water (100 / 10 ml), and add Pd(PPh3)4 (1.15 g, 1 mmol) and potassium carbonate (4.1 g, 30 mmol). Stir at 100 °C for 12 h under a nitrogen atmosphere. After cooling, most of the solvent is removed by rotary evaporation, and then extraction, washing, and liquid separation are carried out. The organic phase is subjected to column chromatography and recrystallization to obtain compound 15, yield: 63%. MS(ASAP)=862.4

[0307] Synthesis of compound 16 in Example 16

[0308]

[0309] Synthesis of intermediate 16-1:

[0310] Prepare a dry 250 mL three-necked flask, set up the reaction device, evacuate, and introduce nitrogen; keep the nitrogen flowing in the reaction flask, weigh 1-1 (5.0 g, 16 mmol), and add THF (100 ml), evacuate and introduce nitrogen three times in a cycle, and cool down to -78 °C; slowly dropwise add n-butyllithium solution (6.2 ml, 16 mmol) to the reaction flask, and after reacting at -78 °C for 60 min, quickly add anhydrous acetone (2.8 g, 48 mmol). Let the reaction system slowly rise to room temperature and react for 12 h. Add water, extract with DCM, after rotary evaporation of the solvent, triturate with PE to obtain a white solid. Yield 59%. MS(ASAP)=302.1

[0311] Synthesis of intermediate 16-2:

[0312] Place intermediate 16-1 (10 g, 33 mmol) in a 100 ml two-necked flask. Add 20 ml of H2SO4 until all the solid is dissolved, and stir at 100 °C for 12 h. After the reaction is completed, slowly pour the reaction solution into ice water, extract with DCM, collect the organic layer, wash with water, and perform column chromatography (eluent: PE) to obtain a white solid with a yield of 52%. MS (ASAP) = 284.1

[0313] Synthesis of intermediate 16-3:

[0314] Place intermediate 16-2 (4.8 g, 17 mmol) in a 250 ml two-necked flask. Add 100 ml of DMF until all the solid is dissolved. Weigh NBS (3.1 g, 17 mmol) and place it in a constant pressure dropping funnel, dissolve it with 20 ml of DMF, slowly add dropwise, and react at room temperature for 12 h. Evaporate to dryness, wash with water, and perform column chromatography (eluent: PE) to obtain a white solid with a yield of 78%. MS (ASAP) = 362.0

[0315] Synthesis of intermediate 16-4:

[0316] Weigh 16-3 (5.0 g, 13.8 mmol), (Bpin)2 (4.2 g, 16.5 mmol), AcOK (6.8 g, 69 mmol), and Pd(dppf)Cl2 (0.20 g, 0.28 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. Evaporate to dryness, wash with water, and perform column chromatography (eluent: PE:DCM = 6:1) to obtain a colorless oil with a yield of 78%. MS (ASAP) = 410.2

[0317] Synthesis of intermediate 16-5:

[0318] Dissolve intermediate 9,10-dibromoanthracene (3.4 g, 10 mmol) and dibenzothiophene-2-boronic acid (2.3 g, 10 mmol) in a mixed solvent of 1,4-dioxane and water (100 / 10 ml), and add Pd(PPh3)4 (0.58 g, 0.5 mmol) and potassium carbonate (6.9 g, 50 mmol). Stir at 100 °C for 12 h under a nitrogen atmosphere. After cooling, rotary evaporate to remove most of the solvent, then extract and wash and separate the liquid. The organic phase is subjected to column chromatography (eluent: PE) and recrystallization to obtain compound 16-5 with a yield of 83%. MS (ASAP) = 438.0

[0319] Synthesis of compound 16:

[0320] Dissolve intermediate Intermediate 16-4 (4.1 g, 10 mmol) and Intermediate 16-5 (4.4 g, 10 mmol) in a mixed solvent of 1,4-dioxane and water (100 / 10 ml), and add Pd(PPh3)4 (0.58 g, 0.5 mmol) and potassium carbonate (6.9 g, 50 mmol). Stir at 100 °C for 12 h under a nitrogen atmosphere. After cooling, most of the solvent was removed by rotary evaporation, then extracted, washed with water and separated by liquid separation. The organic phase was subjected to column chromatography (the eluent was PE) and recrystallized to obtain Compound 16, yield: 68%. MS(ASAP)=642.2

[0321] Synthesis of Compound 17 in Example 17

[0322]

[0323] Synthesis of Intermediate 17-1:

[0324] Dissolve intermediate 9,10-dibromoanthracene (10 g, 30 mmol) and fluoranthene-3-boronic acid (7.4 g, 30 mmol) in a mixed solvent of 1,4-dioxane and water (100 / 10 ml), and add Pd(PPh3)4 (1.7 g, 1.5 mmol) and potassium carbonate (20.7 g, 150 mmol). Stir at 100 °C for 12 h under a nitrogen atmosphere. After cooling, most of the solvent was removed by rotary evaporation, then extracted, washed with water and separated by liquid separation. The organic phase was subjected to column chromatography and recrystallized to obtain Intermediate 17-1, yield: 82%. MS(ASAP)=456.1

[0325] Synthesis of Compound 17:

[0326] Dissolve Intermediate 17-1 (4.6 g, 10 mmol) and 13-4 (6.5 g, 10 mmol) in a mixed solvent of 1,4-dioxane and water (100 / 10 ml), and add Pd(PPh3)4 (1.15 g, 1 mmol) and potassium carbonate (4.1 g, 30 mmol). Stir at 100 °C for 12 h under a nitrogen atmosphere. After cooling, most of the solvent was removed by rotary evaporation, then extracted, washed with water and separated by liquid separation. The organic phase was subjected to column chromatography and recrystallized to obtain Compound 17, yield: 53%. MS(ASAP)=896.4

[0327] Synthesis of Compound 18 in Example 18

[0328]

[0329] Synthesis of Intermediate 18-1:

[0330] Dissolve intermediate 9,10-dibromoanthracene (6.7 g, 20 mmol) and 4-biphenylboronic acid (4.0 g, 20 mmol) in a mixed solvent of 1,4-dioxane and water (100 / 10 ml), and add Pd(PPh3)4 (1.2 g, 1.0 mmol) and potassium carbonate (14 g, 100 mmol). Stir at 100 °C for 12 h under a nitrogen atmosphere. After cooling, most of the solvent is removed by rotary evaporation, and then extraction, washing, and liquid separation are carried out. The organic phase is subjected to column chromatography and recrystallization to obtain intermediate 18-1, yield: 84%. MS(ASAP) = 408.1

[0331] Synthesis of Compound 18:

[0332] Dissolve intermediate 18-1 (4.1 g, 10 mmol) and 16-4 (4.1 g, 10 mmol) in a mixed solvent of 1,4-dioxane and water (100 / 10 ml), and add Pd(PPh3)4 (0.58 g, 0.5 mmol) and potassium carbonate (6.9 g, 50 mmol). Stir at 100 °C for 12 h under a nitrogen atmosphere. After cooling, most of the solvent is removed by rotary evaporation, and then extraction, washing, and liquid separation are carried out. The organic phase is subjected to column chromatography and recrystallization to obtain Compound 18, yield: 57%. MS(ASAP) = 612.3

[0333] Synthesis of Compound 19 in Example 19

[0334]

[0335] Synthesis of Intermediate 19-1:

[0336] Dissolve intermediate 9-bromo-10-(1-phenyl)anthracene (3.3 g, 10 mmol) and 4-bromophenylboronic acid (2.0 g, 10 mmol) in a mixed solvent of 1,4-dioxane and water (100 / 10 ml), and add Pd(PPh3)4 (1.2 g, 1.0 mmol) and potassium carbonate (14 g, 100 mmol). Stir at 100 °C for 12 h under a nitrogen atmosphere. After cooling, most of the solvent is removed by rotary evaporation, and then extraction, washing, and liquid separation are carried out. The organic phase is subjected to column chromatography and recrystallization to obtain intermediate 19-1, yield: 77%. MS(ASAP) = 408.1

[0337] Synthesis of Compound 19:

[0338] Intermediate 19-1 (4.1 g, 10 mmol) and 1-5 (5.4 g, 10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (100 / 10 ml), and Pd(PPh3)4 (0.58 g, 0.5 mmol) and potassium carbonate (6.9 g, 50 mmol) were added. Under a nitrogen atmosphere, the mixture was stirred at 100 °C for 12 h. After cooling, most of the solvent was removed by rotary evaporation, and then the mixture was extracted, washed with water, and separated by liquid-liquid extraction. The organic phase was purified by column chromatography and recrystallization to obtain Compound 19 with a yield of 66%. MS (ASAP) = 736.3

[0339] 2. Preparation of OLED Devices

[0340] The chemical structures of the compounds involved in the preparation of OLED devices are as follows:

[0341]

[0342] The preparation process of the OLED device using the above compounds is described in detail below by specific examples. The structure of the OLED device is: ITO / HIL / HTL / EML / ETL / Cathode. The schematic diagram of the OLED device is shown in Figure 1 Figure [Figure number not provided in the original text], where 101 is the substrate, 102 is the anode, 103 is the hole injection layer (HIL), 104 is the hole transport layer (HTL), 105 is the emitting layer (EML), 106 is the electron transport layer (ETL), and 107 is the cathode.

[0343] The preparation steps of OLED-1 are as follows:

[0344] a. Cleaning of the ITO (indium tin oxide) conductive glass substrate: The substrate was cleaned with various solvents (such as chloroform, acetone, or isopropanol, or a combination of them), and then treated with ultraviolet ozone;

[0345] b. HIL (hole injection layer, 40 nm): 60 nm of PEDOT (poly(3,4-ethylenedioxythiophene), Clevios TM AI4083) was spin-coated as the HIL in a cleanroom and treated on a hot plate at 180 °C for 10 minutes;

[0346] c. HTL (hole transport layer, 20 nm): 20 nm of PVK (Sigma Aldrich, average Mn 25,000 - 50,000) was spin-coated in a nitrogen glove box. The solution used was PVK added to toluene solvent with a concentration of 5 mg / ml, and then treated on a hot plate at 180 °C for 60 minutes;

[0347] d, EML (Organic Light-Emitting Layer, 40 nm): The EML was formed by spin coating in a nitrogen glove box. The solution used was a solution of the host and guest in methyl benzoate (the weight ratio of the host to the guest was 95:5), with a solution concentration of 15 mg / ml. Subsequently, it was treated on a hot plate at 140 °C for 10 minutes. The host used was Compound 1 of Example 1, and the guest material was selected from BD-1.

[0348] e, Electron Transport Layer and Cathode: The heat-treated substrate was transferred to a vacuum chamber. Then, ET and Liq were placed in different evaporation units and co-deposited at a ratio of 50 wt% each in a high vacuum (1×10 -6 mbar) to form a 20-nm electron transport layer on the light-emitting layer. Subsequently, an Al cathode with a thickness of 100 nm was deposited.

[0349] f, Encapsulation: The device was encapsulated with ultraviolet curable resin in a nitrogen glove box.

[0350] The other device implementation schemes were the same, except that Compound 1 in OLED-1 was replaced with the corresponding compound of the host material in Table 2.

[0351] The current-voltage (J-V) characteristics of each OLED device were characterized by a characterization device, and important parameters such as efficiency, lifetime, and external quantum efficiency were recorded simultaneously. The results are shown in Table 1.

[0352] Table 1

[0353]

[0354]

[0355] Upon detection, the color coordinates of the blue light devices prepared using Compounds 1 - 19 as the host material of the EML layer are superior to those of Comparative Compound 1, and deep blue emission can be achieved. In addition, the luminous efficiencies of the blue light devices prepared using Compounds 1 - 19 as the host material of the EML layer are all in the range of 5 - 7 cd / A, with more excellent luminous efficiency. Moreover, the lifetimes of the blue light devices prepared using Compounds 1 - 19 as the host material of the EML layer are high; the performance of devices OLED-4, 10, 15, 16 is better than that of other devices. For devices OLED-15, 16, more hole transport groups are introduced into the molecule, making the device reach a more ideal electrical balance state, thus improving the device performance. For devices OLED-4, 10, part of the molecule is deuterated, increasing the molecular stability and thus improving the overall device performance.

[0356] The technical features of the above-described embodiments can be combined arbitrarily. For the sake of brevity of description, not all possible combinations of the technical features in the above embodiments are described. However, as long as there is no contradiction in the combination of these technical features, it should be considered as the scope recorded in this specification.

[0357] The above-described embodiments only express several implementation manners of the present invention. The description is relatively specific and detailed, but it should not be construed as a limitation on the scope of the invention patent. It should be noted that for those of ordinary skill in the art, without departing from the concept of the present invention, several modifications and improvements can still be made, and these all belong to the protection scope of the present invention. Therefore, the protection scope of the present invention patent shall be subject to the appended claims.

Claims

1. An organic compound, characterized in that, It has a structure shown in general formula (1): Wherein: Ar1 is selected from one of the following groups: X is selected from CR6, and each occurrence of R6 is independently selected from -H, -D or an unsubstituted aromatic group having 6 to 10 ring atoms. When X is a connection site, X is C; Y is selected from O, S; L1 and L2 are independently selected from a single bond or one of the following groups: Each occurrence of X2 is independently selected from CR 14 or N, R 14 Each occurrence is independently selected from -H, -D, a straight-chain alkyl group having 1 to 4 C atoms, an unsubstituted aromatic group having 6 to 10 ring atoms, and when X2 is a linking site, X2 is C; Each occurrence of R4 and R5 is independently selected from a straight-chain alkyl group having 1 to 4 C atoms, a branched-chain alkyl group having 3 to 5 C atoms, an unsubstituted aromatic group having 6 to 14 ring atoms, or an aromatic group having 6 to 14 ring atoms substituted by an alkyl group having 1 to 5 C atoms; m1 is selected from 0, m2 is selected from 0, and m3 is selected from 0.

2. The organic compound according to claim 1, characterized in that, The organic compound has a structure shown in any one of general formulas (2-1) to (2-4): Wherein, X, Y, L1, L2, m1, m2, m3, R4 and R5 are defined as described in claim 1.

3. The organic compound according to claim 1, characterized in that, The Ar1 is selected from one of the following groups: Wherein: * represents a connection site.

4. The organic compound according to claim 1, wherein Each occurrence of the R4 and R5 is independently selected from a straight-chain alkyl group having 1 to 4 C atoms, or a branched-chain alkyl group having 3 to 5 C atoms, or one of the following groups: Wherein: Each occurrence of X1 is independently selected from CR 10 When X1 is a linking site, X1 is C; R 10 Each occurrence is independently selected from -H, methyl, propyl, tert-butyl.

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

6. An organic compound, characterized in that, The organic compound is selected from one of the following structures:

7. A mixture, characterized in that, It contains the organic compound described in any one of claims 1-5 or the organic compound described in claim 6, and at least one other organic functional material.

8. A composition, characterized in that, It contains the organic compound described in any one of claims 1-5 or the organic compound described in claim 6 or the mixture described in claim 7, and at least one organic solvent.

9. An organic electronic device, characterized in that, It includes a cathode, an anode, and one or more organic functional layers located between the cathode and the anode. The organic functional layer contains the organic compound described in any one of claims 1-5, or the organic compound described in claim 6, or the mixture described in claim 7, or is prepared from the composition described in claim 8.

10. The organic electronic device according to claim 9, wherein The organic functional layer at least includes a light-emitting layer, and the material of the light-emitting layer contains an organic compound having a structure shown in formula (3); Wherein: Ar4 - Ar7 includes a structure shown in any of the following: Wherein: Each occurrence of V is independently selected from CR 19 or N, and when V is a linking site, V is selected from C; W is selected from NR 20 , CR 20 R 21 , SiR 20 R 21 , O, S, S=O or SO2; R 19 -R 21 Each occurrence is independently selected from -H, -D, or a straight-chain alkyl group having 1 to 10 carbon atoms, or a branched-chain alkyl group having 3 to 10 carbon atoms, or a cyclic alkyl group having 3 to 10 carbon atoms, or an aromatic group having 6 to 30 ring atoms substituted with any one of D, methyl, propyl, tert-butyl, or an unsubstituted aromatic group having 6 to 30 ring atoms, or an unsubstituted heteroaromatic group having 5 to 30 ring atoms; R 18 Each occurrence is independently selected from -H, methyl, propyl; s is selected from 0, 1 or 2.

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