Arylamine organic compound and application thereof in organic electronic device

Abstract

The invention relates to an organic compound containing arylamine and application of the organic compound in an organic electronic device. The organic compound provided by the invention has relatively high thermal stability, and can improve the luminous efficiency and the service life of a device.

Description

Aromatic amine organic compounds and their applications in organic electronic devices Technical Field

[0001] The present invention relates to the technical field of organic electronic materials and devices, and in particular to an aromatic amine organic compound, a mixture containing the aromatic amine organic compound, and applications thereof in organic electronic devices, in particular in organic light-emitting diodes. Background Art

[0002] Organic light-emitting diodes (OLEDs) have great potential for applications in optoelectronic devices such as flat-panel displays and lighting due to the synthetic diversity, relatively low manufacturing costs, and excellent optical and electrical properties of organic semiconductor materials.

[0003] Organic electroluminescence (OLED) refers to the conversion of electrical energy into light energy using organic substances. OLED elements that utilize this phenomenon typically have a positive electrode and a negative electrode with an organic layer between them. To improve the efficiency and lifespan of OLED elements, the organic layer has a multilayer structure, with each layer containing 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, and the like. In such an OLED element, when a voltage is applied between the two electrodes, holes are injected from the positive electrode into the organic layer, and electrons are injected from the negative electrode into the organic layer. When the injected holes and electrons meet, excitons are formed, which then emit light when they transition back to the ground state. Such OLED elements exhibit characteristics such as self-luminescence, high brightness, high efficiency, low driving voltage, wide viewing angle, high contrast, and high responsiveness. Typically, the large difference in the highest occupied molecular orbital (HOMO) energy levels between the hole transport layer and the light-emitting layer increases the difficulty of holes from the hole transport layer to the light-emitting layer, leading to hole accumulation at the interface between the hole transport layer and the light-emitting layer. To address these issues, a hole-assisting layer can be introduced between the hole transport layer and the light-emitting layer to promote hole transport.

[0004] Although existing technologies such as CN111146349A, CN111279502A, CN113135903A, and CN113461547A disclose some hole transport materials used as hole auxiliary layers, it is still necessary to design and develop new materials to reduce device voltage and improve device efficiency and life.

[0005] Summary of the Invention

[0006] In view of the above-mentioned deficiencies in the prior art, the present invention aims to provide a class of aromatic amine organic compounds, including mixtures thereof, and applications thereof in organic electronic devices, aiming to solve the problems of low efficiency and lifespan of existing organic electronic devices.

[0007] The technical solutions of the present invention are as follows:

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

[0009] wherein: A and B are independently selected from hydrogen or a group of formula (I-1) or formula (I-2), and only one of A and B is a group of formula (I-1) or formula (I-2);

[0010] “*” indicates the connection position;

[0011] X is O, S, NR1, CR2R3;

[0012] Y may be the same or different in each case and is represented by CR4 or N, wherein no more than two Y groups per ring are N; L1 is selected from a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms or a substituted or unsubstituted heteroarylene group having 2 to 30 ring carbon atoms; L2-L3 are each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms or a substituted or unsubstituted heteroarylene group having 2 to 30 ring carbon atoms;

[0013] Ar1-Ar2 are each independently selected from a substituted or unsubstituted aromatic or heteroaromatic group having 5 to 40 ring atoms, or an aryloxy or heteroaryloxy group having 5 to 40 ring atoms, or a combination of these groups, wherein one or more of the groups can form a monocyclic or polycyclic aliphatic or aromatic ring system with each other and / or the ring to which they are bonded;

[0014] R1-R4 are substituents which, at each occurrence, may be identical or different and are H, D, or a linear alkyl, alkoxy or thioalkoxy group having 1 to 20 C atoms, or a branched or cyclic alkyl, alkoxy or thioalkoxy group having 3 to 20 C atoms or a silyl group, or a substituted 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, or a cyano group (-CN), a carbamoyl group (-C(=O)NH2), a haloformyl group (- C(═O)—X, wherein X represents a halogen atom), a formyl group (—C(═O)—H), an isocyanate group, an isocyanate group, a thiocyanate group or an isothiocyanate group, a hydroxyl group, a nitro group, CF 3 , Cl, Br, F or a crosslinkable group, or a substituted or unsubstituted aromatic or heteroaromatic ring system having 5 to 40 ring atoms, or an aryloxy or heteroaryloxy group having 5 to 40 ring atoms, or a combination of these groups; any two adjacent substituents in R1 to R4 can form a monocyclic or polycyclic aliphatic or aromatic ring system with each other and / or with the ring to which the groups are bonded.

[0015] The above organic compound has a structure as shown in general formula (II):

[0016] Wherein: L2-L3 are each independently selected from a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms or a substituted or unsubstituted heteroarylene group having 2 to 30 ring carbon atoms; X, Y, L1, Ar1, and Ar2 are as defined above. Preferably, L2 and / or L3 are not fluorene.

[0017] A mixture comprising an organic compound as described above and at least another organic functional material, wherein the organic functional material is selected from one or more of hole injection materials, hole transport materials, electron transport materials, electron injection materials, electron blocking materials, hole blocking materials, luminescent materials, host materials, and organic dyes.

[0018] The present invention also provides an organic electronic device comprising a functional layer, wherein the functional layer comprises the organic compound or mixture as described above.

[0019] The above-mentioned organic electronic device is an organic electroluminescent device, which includes a first electrode; a hole transport region, which is arranged on the first electrode; a light-emitting layer, which is arranged on the hole transport region; an electron transport region, which is arranged on the light-emitting layer; and a second electrode, which is arranged on the electron transport region; wherein the hole transport region contains at least one organic compound or mixture as described above.

[0020] In the above organic electronic device, the hole transport region has a multilayer structure having a plurality of layers, and at least one layer in the multilayer structure that is in contact with the light-emitting layer comprises an organic compound or mixture as described above.

[0021] Beneficial effects: The organic compound of the present invention is used in the hole auxiliary layer of the organic electroluminescent device, which can effectively promote the hole transport from the hole transport layer to the light-emitting layer, thereby achieving high luminous efficiency and long life of the device. DETAILED DESCRIPTION

[0022] The present invention provides an aromatic amine organic compound and its use in an organic electroluminescent device, as well as an organic electronic device containing the aromatic amine organic compound and a method for preparing the same. To further clarify and define the objectives, technical solutions, and effects of the present invention, the present invention is described in further detail below. It should be understood that the specific embodiments described herein are intended solely to illustrate the present invention and are not intended to limit the present invention.

[0023] In the present invention, the energy level structure of organic materials, the singlet energy level S1, the triplet energy level T1, the HOMO, and the LUMO, play a key role. The determination of these energy levels is described below.

[0024] HOMO and LUMO energy levels can be measured by photoelectric effects, such as XPS (X-ray photoelectron spectroscopy) and UPS (ultraviolet photoelectron spectroscopy), or by cyclic voltammetry (CV). Recently, quantum chemical methods, such as density functional theory (DFT), have also become effective methods for calculating molecular orbital energy levels.

[0025] The singlet energy level S1 of an organic material can be determined by luminescence spectroscopy, and the triplet energy level T1 can be measured by low-temperature time-resolved luminescence spectroscopy. S1 and T1 can also be obtained by quantum simulation calculations (e.g., by time-dependent DFT), such as using the commercial software Gaussian 09W (Gaussian Inc.). Specific simulation methods can be found in WO2011141110 or described in the Examples below. ΔE ST Defined as (S1-T1).

[0026] It should be noted that the absolute values ​​of HOMO, LUMO, S1, and T1 depend on the measurement or calculation method used. Even for the same method, different evaluation methods, such as the onset and peak points on a CV curve, can give different HOMO / LUMO values. Therefore, reasonable and meaningful comparisons should be made using the same measurement and evaluation methods. In the description of the embodiments of the present invention, the values ​​of HOMO, LUMO, S1, and T1 are based on time-dependent DFT simulations, but this does not affect the application of other measurement or calculation methods.

[0027] In the present invention, (HOMO-1) is defined as the second-highest occupied molecular orbital energy level, (HOMO-2) is the third-highest occupied molecular orbital energy level, and so on. (LUMO+1) is defined as the second-lowest unoccupied molecular orbital energy level, (LUMO+2) is the third-lowest occupied molecular orbital energy level, and so on.

[0028] In the present invention, composition and printing ink, or ink have the same meaning and can be interchanged.

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

[0030] In the present invention, heteroaromatic group, heteroaromatic series and heteroaromatic ring system have the same meaning and can be interchanged.

[0031] In the present invention, "substituted" means that a hydrogen atom in a substituted group is replaced by a substituent.

[0032] In the present invention, the "number of ring atoms" refers to the number of atoms in the atoms that constitute the ring itself of a structural compound (e.g., a monocyclic compound, a condensed ring compound, a cross-linked compound, a carbocyclic compound, or a heterocyclic compound) formed by atoms bonded together to form a ring. When the ring is substituted with a substituent, the atoms contained in the substituent are not included in the ring atoms. The "number of ring atoms" described below also applies unless otherwise specified. For example, the number of ring atoms of a benzene ring is 6, the number of ring atoms of a naphthalene ring is 10, and the number of ring atoms of a thienyl group is 5.

[0033] In the present invention, an aromatic ring system or aromatic group refers to a hydrocarbon group containing at least one aromatic ring, including monocyclic groups and polycyclic ring systems. A heteroaromatic ring system or heteroaromatic group refers to a hydrocarbon group (containing heteroatoms) containing at least one heteroaromatic ring, including monocyclic groups and polycyclic ring systems. The heteroatoms are preferably selected from Si, N, P, O, S and / or Ge, particularly preferably from Si, N, P, O and / or S. These polycyclic rings can have two or more rings, in which two carbon atoms are shared by two adjacent rings, i.e., fused rings. At least one of these polycyclic ring species is aromatic or heteroaromatic. For the purposes of the present invention, an aromatic group or heteroaromatic group includes not only a system of aromatic or heteroaromatic groups, but also, wherein multiple aromatic or heteroaromatic groups may be interrupted by short non-aromatic units (<10% non-H atoms, preferably less than 5% non-H atoms, such as C, N or O atoms). Thus, for example, 9,9'-spirobifluorene, 9,9-diarylfluorene, triarylamines, diaryl ethers, etc., are also considered aromatic groups for the purposes of this invention.

[0034] Specific examples of the aromatic group include benzene, naphthalene, anthracene, phenanthrene, perylene, tetracene, pyrene, benzopyrene, triphenylene, acenaphthene, fluorene, and derivatives thereof.

[0035] Specific examples of heteroaromatic groups include furan, benzofuran, thiophene, benzothiophene, pyrrole, pyrazole, triazole, imidazole, oxazole, oxadiazole, thiazole, tetrazole, indole, carbazole, pyrroloimidazole, pyrrolopyrrole, thienopyrrole, thienothiophene, furopyrrole, furofuran, thienofuran, benzisoxazole, benzisothiazole, benzimidazole, pyridine, pyrazine, pyridazine, pyrimidine, triazine, quinoline, isoquinoline, o-naphthylidene, quinoxaline, phenanthridine, primary idine, quinazoline, quinazolinone, and derivatives thereof.

[0036] In the present invention, "alkyl" may refer to a linear, branched and / or cyclic alkyl group. The carbon number of the alkyl group may be 1 to 50, 1 to 30, 1 to 20, 1 to 10 or 1 to 6. Non-limiting examples of alkyl groups include methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, tert-butyl, isobutyl, 2-ethylbutyl, 3,3-dimethylbutyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, cyclopentyl, 1-methylpentyl, 3-methylpentyl, 2-ethylpentyl, 4-methyl-2-pentyl, n-hexyl, 1-methylhexyl, 2-ethylhexyl, 2-butylhexyl, cyclohexyl, 4-methylcyclohexyl, 4-tert-butylcyclohexyl, n-heptyl, 1-methylheptyl, 2,2-dimethylheptyl, 2-ethylheptyl, 2-butylheptyl, n-octyl, tert-octyl, 2-ethyloctyl, 2-butyloctyl, 2-hexyloctyl, 3,7-dimethyloctyl, cyclooctyl, n-nonyl, n-decyl, adamantyl, 2-ethyldecyl, 2-butyl decyl, 2-ethyldodecyl, 2-butyldodecyl, 2-hexyldodecyl, 2-octyldodecyl, n-tridecyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, 2-ethylhexadecyl, 2-butylhexadecyl, 2-hexylhexadecyl, 2-octylhexadecyl, n-heptadecyl, n-octadecyl, n-nonadecyl, n-eicosyl, 2-ethyleicosyl, 2-butyleicosyl, 2-hexyleicosyl, 2-octyleicosyl, n-heneicosyl, n-docosyl, n-tricosyl, n-tetracosyl, n-pentacosyl, n-hexacosyl, n-heptacosyl, n-octacosyl, n-nonacosyl, n-triacontyl, and the like.

[0037] An organic compound of the present invention has a structure as shown in general formula (I):

[0038] wherein: A and B are independently selected from hydrogen or a group of formula (I-1) or formula (I-2), and only one of A and B is a group of formula (I-1) or formula (I-2); "*" indicates the connection position; X is O, S, NR1, CR2R3; Y can be the same or different in each case and is represented by CR4 or N, wherein no more than two Y groups in each ring are N.

[0039] L1 is selected from a substituted or unsubstituted aromatic group having 6 to 30 ring carbon atoms or a substituted or unsubstituted heteroaromatic group having 2 to 30 ring carbon atoms; L2-L3 are each independently selected from a single bond, a substituted or unsubstituted aromatic group having 6 to 30 ring carbon atoms or a substituted or unsubstituted heteroaromatic group having 2 to 30 ring carbon atoms; Ar1-Ar2 are each independently selected from a substituted or unsubstituted aromatic group or heteroaromatic group having 5 to 40 ring atoms, or an aryloxy or heteroaryloxy group having 5 to 40 ring atoms, or a combination of these groups, wherein one or more of the groups can form a monocyclic or polycyclic aliphatic or aromatic ring system with each other and / or the ring bonded to the group; R1-R4 are substituents, which may be the same or different at each occurrence and are H, D, or a straight-chain alkyl, alkoxy or thioalkoxy group having 1 to 20 carbon atoms, or a branched or cyclic alkyl, alkoxy group having 3 to 20 carbon atoms or a thioalkoxy group or a silyl group, or a substituted 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, or a cyano group (-CN), a carbamoyl group (-C(=O)NH2), a haloformyl group (-C(=O)-X wherein X represents a halogen atom), a formyl group (-C(=O)-H), an isocyano group, an isocyanate an ester group, a thiocyanate group or an isothiocyanate group, a hydroxyl group, a nitro group, a CF3 group, Cl, Br, F or a crosslinkable group, or a substituted or unsubstituted aromatic or heteroaromatic ring system having 5 to 40 ring atoms, or an aryloxy or heteroaryloxy group having 5 to 40 ring atoms, or a combination of these groups; wherein any two adjacent substituents of R1 to R4 can form a monocyclic or polycyclic aliphatic or aromatic ring system with each other and / or with the ring to which they are bonded.

[0040] Further, each occurrence of R1-R4 is independently selected from D, cyano, straight-chain alkyl having 1 to 18 carbon atoms, or branched or cyclic alkyl, alkoxy, thioalkoxy or silyl having 3 to 18 carbon atoms, or substituted or unsubstituted aromatic, heteroaromatic, aryloxy or heteroaryloxy having 5 to 30 ring atoms; in a more preferred embodiment, each occurrence of R1-R4 is independently selected from D, straight-chain alkyl having 1 to 12 carbon atoms, or substituted or unsubstituted aromatic, heteroaromatic, aryloxy or heteroaryloxy having 5 to 20 ring atoms; in a most preferred embodiment, each occurrence of R1-R4 is independently selected from D, straight-chain alkyl having 1 to 6 carbon atoms, or substituted or unsubstituted aromatic, heteroaromatic, aryloxy or heteroaryloxy having 5 to 15 ring atoms, and adjacent R1 to R4 can form a monocyclic or polycyclic aliphatic or aromatic ring system with each other and / or the rings to which they are bonded.

[0041] In some preferred embodiments, each occurrence of R1-R4 is fully or partially deuterated.

[0042] In some preferred embodiments, the organic compound according to the present invention has a structure as shown in the general formula (II):

[0043] Wherein: L2-L3 are each independently selected from a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms or a substituted or unsubstituted heteroarylene group having 2 to 30 ring carbon atoms; X, Y, L1, Ar1, and Ar2 are as defined above. Preferably, L2 and / or L3 are not fluorene.

[0044] In some preferred embodiments, the organic compound according to the present invention, wherein: two adjacent Ys can be simultaneously bonded to a group represented by formula (I-3) or formula (I-4) and the remaining Ys are the same or different in each case and represent CR4 or N,

[0045] Wherein the dotted bond represents the bonding position, Z represents N or CR5, Q is selected from O, S, NR1, CR2R3, R4 has the same meaning as above, and R5 has the same meaning as R4.

[0046] In some preferred embodiments, the organic compound according to the present invention has a structure represented by the general formula (II-01) to (II-10):

[0047] Wherein, the dotted line represents a connecting bond; X, Q, Z, L1, and Ar1-Ar2 have the same meanings as above; L2-L3 are selected from substituted or unsubstituted arylene groups having 6 to 30 ring carbon atoms or substituted or unsubstituted heteroarylene groups having 2 to 30 ring carbon atoms. Preferably, L2 and / or L3 are not fluorene.

[0048] In some embodiments, L1 is independently selected from the following groups and combinations thereof:

[0049] Wherein: X1, at each occurrence, is independently selected from CR6 or N;

[0050] Each occurrence of Y1 is independently selected from NR7, CR8R9, O, S, SiR 10 R 11 , S=O, SO2;

[0051] R6-R 11Each occurrence is independently selected from: H, D, or straight-chain alkyl having 1 to 20 C atoms, or straight-chain alkoxy having 1 to 20 C atoms, or straight-chain thioalkoxy having 1 to 20 C atoms, or branched or cyclic alkyl having 3 to 20 C atoms, or branched or cyclic alkoxy having 3 to 20 C atoms, or branched or cyclic thioalkoxy having 3 to 20 C atoms, silyl, or keto having 1 to 20 C atoms, or alkoxycarbonyl having 2 to 20 C atoms, or an aryloxycarbonyl group having 7 to 20 C atoms, or a cyano group, a carbamoyl group, a haloformyl group, a formyl group, an isocyano group, an isocyanate group, a thiocyanate group, an isothiocyanate group, a hydroxyl group, a nitro group, CF3, Cl, Br, F, a crosslinkable group, or a substituted or unsubstituted aromatic group having 5 to 60 ring atoms, or a substituted or unsubstituted heteroaromatic group having 5 to 60 ring atoms, or an aryloxy group having 5 to 60 ring atoms, or a heteroaryloxy group having 5 to 60 ring atoms, or a combination of these groups, R6-R 11 Any two adjacent substituents in the group may form a monocyclic or polycyclic aliphatic or aromatic ring system with each other and / or with the ring to which they are bonded.

[0052] In some embodiments, L1 is independently selected from the following groups or combinations thereof:

[0053] Among them: The H atoms on the ring can be further substituted.

[0054] Specifically, L1 is selected from the following groups and combinations thereof:

[0055] Among them, R 12 -R 28 The meaning is the same as R1.

[0056] In some embodiments, L2-L3 are independently selected from the following groups and combinations thereof:

[0057] Where: Each time X2 appears, it is independently selected from CR 1 or N;

[0058] Each occurrence of Y2 is independently selected from NR 2 、O、S、SiR 3 R 4 、S=O、SO2、CR 5 R 6 ;

[0059] R 1 -R 6Each 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 or cyclic alkyl group having 3 to 20 C atoms, or a branched or cyclic alkoxy group having 3 to 20 C atoms, or a branched or cyclic thioalkoxy group, 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, or a cyano group, a carbamoyl group, a haloformyl group, a formyl group, an isocyano group, an isocyanate group, a thiocyanate group, an isothiocyanate group, a hydroxyl group, a nitro group, CF3, Cl, Br, F, a crosslinkable group, or a substituted or unsubstituted aromatic group having 5 to 60 ring atoms, or a substituted or unsubstituted heteroaromatic group having 5 to 60 ring atoms, or an aryloxy group having 5 to 60 ring atoms, or a heteroaryloxy group having 5 to 60 ring atoms, or a combination of these groups, R 1 -R 6 Any two adjacent substituents in the group may form a monocyclic or polycyclic aliphatic or aromatic ring system with each other and / or with the ring bonded to the group. Preferably, each occurrence of Y2 is independently selected from NR 2 、O、S、SiR 3 R 4 , S=O, SO2.

[0060] In some preferred embodiments, L2-L3 are each independently selected from the following groups and combinations thereof:

[0061] Among them, R 12 -R 28 has the same meaning as above.

[0062] In some embodiments, Ar1 and Ar2 are independently selected from the following groups and combinations thereof:

[0063] Where: Z1 is selected from N or CR 29 ; X3 is selected from O, S, S=O, SO2, NR 30 , CR 31 R 32 or SiR 33 R 34 ;

[0064] R 29 -R 34Each 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 or cyclic alkyl group having 3 to 20 C atoms, or a branched or cyclic alkoxy group having 3 to 20 C atoms, or a branched or cyclic thioalkoxy group, 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, or a cyano group, a carbamoyl group, a haloformyl group, a formyl group, an isocyanate group, an isocyanate group, a thiocyanate group, an isothiocyanate group, a hydroxyl group, a nitro group, CF3, Cl, Br, F, a crosslinkable group, or a substituted or unsubstituted aromatic group having 5 to 60 ring atoms, or a substituted or unsubstituted heteroaromatic group having 5 to 60 ring atoms, or an aryloxy group having 5 to 60 ring atoms, or a heteroaryloxy group having 5 to 60 ring atoms, or a combination of these groups.

[0065] Furthermore, Ar1 and Ar2 are independently selected from the following groups and combinations thereof:

[0066] The above groups are optionally substituted by 0, 1, 2 or 3 groups selected from D, F, Cl, Br, cyano, C1-C4 alkyl, C1-C3 haloalkyl, phenyl, naphthyl, fluorenyl, spirofluorenyl and C3-C10 cycloalkyl; the meaning of A1 is the same as that of R1 mentioned above.

[0067] In some embodiments, the organic compound according to the present invention is preferably selected from but not limited to the following structures:

[0068] In a preferred embodiment, the organic compound according to the present invention has a glass transition temperature (Tg) ≥ 100°C. In a preferred embodiment, the Tg is ≥ 120°C. In a more preferred embodiment, the Tg is ≥ 140°C. In a more preferred embodiment, the Tg is ≥ 160°C. In a most preferred embodiment, the Tg is ≥ 180°C.

[0069] In certain preferred embodiments, the organic compounds according to the present invention are those wherein ((HOMO-(HOMO-1))≥0.2eV, preferably ≥0.25eV, more preferably ≥0.3eV, even more preferably ≥0.35eV, very preferably ≥0.4eV, and most preferably ≥0.45eV.

[0070] In a more preferred embodiment, the organic compound according to the present invention is partially deuterated, preferably 10% of the H is deuterated, more preferably 20% of the H is deuterated, most preferably 30% of the H is deuterated, and most preferably 40% of the H is deuterated.

[0071] In a preferred embodiment, the organic compound according to the present invention is a small molecule material.

[0072] In a preferred embodiment, the organic compounds according to the present invention are used in vapor-deposited OLED devices. For this purpose, the organic compounds according to the present invention have a molecular weight of ≤1000 g / mol, preferably ≤900 g / mol, very preferably ≤850 g / mol, more preferably ≤800 g / mol, and most preferably ≤700 g / mol.

[0073] The invention further relates to a synthetic method for an organic compound of general formula (I) or general formula (II), wherein a raw material containing an active group is used to react. These active raw materials comprise at least one leaving group, for example, bromine, iodine, boric acid or boric ester. Suitable reactions for forming C-C connections are well known to those skilled in the art and are described in the literature, and particularly suitable and preferred coupling reactions are SUZUKI, STILLE and HECK coupling reactions.

[0074] The present invention also relates to a polymer, wherein at least one repeating unit comprises a structure as shown in general formula (I) or general formula (II). In certain embodiments, the polymer is a non-conjugated polymer, wherein the structural unit as shown in general formula (I) or general formula (II) is on the side chain. In another preferred embodiment, the polymer is a conjugated polymer. The term "small molecule" as defined herein refers to a molecule that is not a polymer, oligomer, dendrimer, or blend. In particular, there is no repeating structure in the small molecule. The molecular weight of the small molecule is ≤3000 g / mol, preferably ≤2000 g / mol, and most preferably ≤1500 g / mol.

[0075] Polymers include homopolymers, copolymers, and block copolymers. In the present invention, polymers also include dendrimers. For information on the synthesis and application of dendrimers, please refer to [Dendrimers and Dendrons, Wiley-VCH Verlag GmbH & Co. KGaA, 2002, Ed. George R. Newkome, Charles N. Moorefield, Fritz Vogtle.].

[0076] A conjugated polymer is a polymer whose main chain backbone is primarily composed of sp2 hybrid orbitals of carbon atoms. Well-known examples include polyacetylene and poly(phenylene vinylene). Carbon atoms in the main chain can be replaced by non-carbon atoms, and even when the sp2 hybridization in the main chain is interrupted by natural defects, it is still considered a conjugated polymer. In the present invention, conjugated polymers also include those containing arylamines, arylphosphine, other heteroaromatics, and organometallic complexes in the main chain.

[0077] In some preferred embodiments, the polymer is synthesized by a method selected from SUZUKI-, YAMAMOTO-, STILLE-, NIGESHI-, KUMADA-, HECK-, SONOGASHIRA-, HIYAMA-, FUKUYAMA-, HARTWIG-BUCHWALD- and ULLMAN.

[0078] In some preferred embodiments, the polymer according to the present invention has a glass transition temperature (Tg) ≥ 100°C, preferably ≥ 120°C, more preferably ≥ 140°C, even more preferably ≥ 160°C, and most preferably ≥ 180°C.

[0079] In a preferred embodiment, the molecular weight distribution (PDI) of the polymer according to the present invention is preferably in the range of 1 to 5, more preferably 1 to 4, more preferably 1 to 3, even more preferably 1 to 2, and most preferably 1 to 1.5.

[0080] In a preferred embodiment, the weight average molecular weight (Mw) of the polymer according to the present invention is preferably in the range of 10,000 to 1,000,000, more preferably 50,000 to 500,000, more preferably 100,000 to 400,000, even more preferably 150,000 to 300,000, and most preferably 200,000 to 250,000.

[0081] The present invention also relates to a mixture comprising an organic compound as described above and at least one other organic functional material, wherein the other organic functional material is selected from a hole injection material (HIM), a hole transport material (HTM), an electron transport material (ETM), an electron injection material (EIM), an electron blocking material (EBM), a hole blocking material (HBM), an emitter, a host material (Host), and an organic dye. For example, various organic functional materials are described in detail in WO2010135519A1, US20090134784A1, and WO2011110277A1, the entire contents of which are hereby incorporated by reference. The organic functional material can be a small molecule or a polymer.

[0082] In a preferred embodiment, the mixture comprises an organic compound according to the present invention and a phosphorescent emitter, wherein the organic compound according to the present invention can serve as the main component and the phosphorescent emitter has a weight percentage of ≤30 wt%, preferably ≤25 wt%, and more preferably ≤20 wt%.

[0083] In another preferred embodiment, the mixture comprises an organic compound according to the present invention, another host material, and a phosphorescent emitter. The organic compound according to the present invention serves as a co-host material and has a weight percentage of ≥10 wt %, preferably ≥20 wt %, more preferably ≥30 wt %, and most preferably ≥40 wt %.

[0084] In a preferred embodiment, the mixture comprises an organic compound according to the present invention, a phosphorescent emitter, and a host material. In this embodiment, the organic compound according to the present invention may serve as an auxiliary luminescent material, with the weight ratio of the organic compound to the phosphorescent emitter being from 1:2 to 2:1. In another preferred embodiment, the organic compound according to the present invention has a higher T1 than the phosphorescent emitter.

[0085] In certain embodiments, the mixture comprises an organic compound according to the present invention, and another TADF material.

[0086] In some more preferred embodiments, the mixture according to the present invention includes an organic functional material H1 selected from the organic compounds described above, and at least another organic functional material H2 selected from hole (also known as hole) injection or transport material (HIM / HTM) and organic host material (Host).

[0087] In certain preferred embodiments, according to the mixture of the present invention, at least one of H1 and H2 has ((LUMO+1)-LUMO) ≥ 0.2eV, preferably ≥ 0.25eV, better ≥ 0.3eV, even better ≥ 0.35eV, very best ≥ 0.4eV, and most preferably ≥ 0.45eV.

[0088] In a more preferred embodiment, the mixture according to the present invention, wherein ((LUMO+1)-LUMO) of H1 is ≥ 0.2 eV, preferably ≥ 0.25 eV, more preferably ≥ 0.3 eV, even more preferably ≥ 0.35 eV, very preferably ≥ 0.4 eV, most preferably ≥ 0.45 eV.

[0089] In certain preferred embodiments, according to the mixture of the present invention, at least one of H1 and H2 has ((HOMO-(HOMO-1)) ≥ 0.2 eV, preferably ≥ 0.25 eV, more preferably ≥ 0.3 eV, even better ≥ 0.35 eV, very preferably ≥ 0.4 eV, and most preferably ≥ 0.45 eV.

[0090] In a more preferred embodiment, according to the mixture of the present invention, the ((HOMO-(HOMO-1)) of H2 is ≥0.2eV, preferably ≥0.25eV, more preferably ≥0.3eV, even better ≥0.35eV, very preferably ≥0.4eV, and most preferably ≥0.45eV.

[0091] In certain more preferred embodiments, the mixture, wherein 1) ΔE(S1-T1) of H1 is ≤0.30 eV, preferably ≤0.25 eV, more preferably ≤0.20 eV, and most preferably ≤0.10 eV; and / or 2) the LUMO of H2 is higher than the LUMO of H1, and the HOMO of H2 is lower than the HOMO of H1.

[0092] In certain preferred embodiments, the mixture, wherein H1 and H2 have a type II semiconductor heterojunction structure, and min((LUMO(H1)-HOMO(H2), LUMO(H2)-HOMO(H1))≤min(ET(H1), ET(H2))+0.1eV, wherein LUMO(H1), HOMO(H1) and ET(H1) are the lowest unoccupied orbital, the highest occupied orbital, and the triplet energy level of H1, respectively, and LUMO(H2), HOMO( (H2) and ET(H2) are the lowest unoccupied molecular orbital (LUMO), highest occupied molecular orbital (HOMO), and triplet energy levels of H2, respectively. Preferably, min((LUMO(H1)-HOMO(H2), LUMO(H2)-HOMO(H1)) ≤ min(ET(H1), ET(H2)); even more preferably, min((LUMO(H1)-HOMO(H2), LUMO(H2)-HOMO(H1)) ≤ min(ET(H1), ET(H2)) - 0.1 eV.

[0093] In a preferred embodiment, H1 and H2 have a type I semiconductor heterojunction structure, and the difference between the singlet energy level and the triplet energy level of H1 or H2 (S1-T1) is less than or equal to 0.25 eV, preferably less than or equal to 0.20 eV, more preferably less than or equal to 0.15 eV, and most preferably less than or equal to 0.10 eV.

[0094] In a preferred embodiment, the mixture, wherein the molar ratio of H1 to H2 is from 1:9 to 9:1; a better molar ratio is 2:8 to 8:2; a preferred molar ratio is 3:7 to 7:3; a more preferred molar ratio is 4:6 to 6:4; and the most preferred molar ratio is 4.5:5.5 to 5.5:4.5.

[0095] In a preferred embodiment, the mixture, wherein the difference in molecular weight between H1 and H2 is no more than 100 Dalton, preferably no more than 80 Dalton, more preferably no more than 70 Dalton, even more preferably no more than 60 Dalton, very preferably no more than 40 Dalton, and most preferably no more than 30 Dalton.

[0096] In another preferred embodiment, in the mixture, the difference in sublimation temperature between H1 and H2 does not exceed 50K; more preferably, the difference in sublimation temperature does not exceed 30K; even more preferably, the difference in sublimation temperature does not exceed 20K; and most preferably, the difference in sublimation temperature does not exceed 10K.

[0097] In a preferred embodiment, at least one of H1 and H2 in the mixture of the present invention has a glass transition temperature Tg ≥ 100°C; in a preferred embodiment, at least one has a Tg ≥ 120°C; in a more preferred embodiment, at least one has a Tg ≥ 140°C; in a more preferred embodiment, at least one has a Tg ≥ 160°C; in a most preferred embodiment, at least one has a Tg ≥ 180°C.

[0098] The organic compounds of the present invention can be used as functional materials in the organic functional layers of electronic devices. Organic functional layers include, but are not limited to, hole injection layer (HIL), hole transport layer (HTL), electron transport layer (ETL), electron injection layer (EIL), electron blocking layer (EBL), hole blocking layer (HBL), and emissive layer (EML).

[0099] In some embodiments, organic compounds according to the present invention are used in a light-emitting layer.

[0100] In some embodiments, organic compounds according to the present invention are used in a hole transport layer.

[0101] The following is a detailed description of singlet host materials, singlet luminophores, TADF luminophores, and HTM (but not limited thereto).

[0102] 1. Singlet Host Material:

[0103] Examples of singlet host materials are not particularly limited, and any organic compound may be used as a host as long as its singlet energy is higher than that of a light emitter, particularly a singlet light emitter or a fluorescent light emitter.

[0104] Examples of organic compounds used as singlet host materials may be selected from aromatic hydrocarbon compounds containing rings, such as benzene, biphenyl, triphenyl, benzo, naphthalene, anthracene, phenanthrene, phenanthrene, fluorene, pyrene, chrysene, perylene, and azulene; aromatic heterocyclic compounds, such as dibenzothiophene, dibenzofuran, dibenzoselenophene, furan, thiophene, benzofuran, benzothiophene, benzoselenophene, carbazole, indole, carbazole, pyridine, indole, pyrrole, dipyridine, pyrazole, imidazole, triazole, isoxazole, thiazole, oxadiazole, oxatriazole, dioxazole, thiadiazole, pyridine, pyridazine, pyrimidine, pyrazine, triazine, oxazine, oxathiazine, oxadiazine, indole, benzimidazole, indazole, Indoleazine, benzoxazole, benzisoxazole, benzothiazole, quinoline, isoquinoline, cinnoline, quinazoline, quinoxaline, naphthalene, phthalide, pteridine, xanthene, acridine, phenazine, phenothiazine, phenoxazine, benzofuran pyridine, furandipyridine, benzothiophene pyridine, thiophene dipyridine, benzoselenophene pyridine and selenophene dipyridine; groups containing 2 to 10 ring structures, which can be cyclic aromatic hydrocarbon groups or aromatic heterocyclic groups of the same or different types, and are linked to each other directly or through at least one of the following groups, such as oxygen atoms, nitrogen atoms, sulfur atoms, silicon atoms, phosphorus atoms, boron atoms, chain structural units and aliphatic ring groups.

[0105] In some preferred embodiments, the singlet host material may be selected from compounds comprising at least one of the following groups:

[0106] Wherein, each occurrence of Y0 is independently selected from C(R) 2 or NR or O or S; X0, at each occurrence, is independently selected from CR or N, R, at each occurrence, is independently selected from the following groups: hydrogen, deuterium, halogen atoms (F, Cl, Br, I), cyano, alkyl, alkoxy, amino, alkenyl, alkynyl, aralkyl, heteroalkyl, aryl and heteroaryl, and n is selected from an integer from 1 to 20.

[0107] In some preferred embodiments, the singlet host is selected from anthracene derivatives, such as those disclosed in patent documents such as CN102224614 B, CN 100471827 C, CN 1914293 B, WO2015033559A1, US2014246657A1, WO2016117848A1, WO2016117861A1, WO2016171429A2, CN102369256B, and CN102428158B.

[0108] Some examples of anthracene-based singlet host materials are listed below:

[0109] In some more preferred embodiments, the anthracene-based singlet host material is deuterated, that is, the host material molecule contains at least one deuterium atom. Such examples are disclosed in patent documents such as CN102369256B, CN102428158B, CN102639671B, and US2015021586A1. Specific examples include:

[0110] 2. Singlet Emitter

[0111] Singlet emitters often have long conjugated π-electron systems. Many examples exist, such as styrylamines and their derivatives disclosed in JP2913116B and WO2001021729A1, indenofluorenes and their derivatives disclosed in WO2008 / 006449 and WO2007 / 140847, and triarylamine derivatives of pyrene disclosed in US7233019 and KR2006-0006760.

[0112] In a preferred embodiment, the singlet emitter can be selected from monostyrylamine, distyrylamine, tertiary styrylamine, tetrastyrylamine, styrylphosphine, styryl ether and aromatic amine.

[0113] A monostyrylamine is a compound comprising an unsubstituted or substituted styryl group and at least one amine, preferably an aromatic amine. A distyrylamine is a compound comprising two unsubstituted or substituted styryl groups and at least one amine, preferably an aromatic amine. A tert-styrylamine is a compound comprising three unsubstituted or substituted styryl groups and at least one amine, preferably an aromatic amine. A tetrastyrylamine is a compound comprising four unsubstituted or substituted styryl groups and at least one amine, preferably an aromatic amine. A preferred styrene is diphenylethylene, which may be further substituted. The corresponding phosphines and ethers are defined similarly to the amines. An arylamine or aromatic amine is a compound comprising three unsubstituted or substituted aromatic or heterocyclic rings directly attached to nitrogen. At least one of these aromatic or heterocyclic ring systems is preferably a fused ring system and preferably has at least 14 aromatic ring atoms. Preferred examples include aromatic anthracenamines, aromatic anthracenediamines, aromatic pyreneamines, aromatic pyrenediamines, aromatic chryseneamines, and aromatic chrysenediamines. An aromatic anthracenamine is a compound in which one diarylamine group is directly attached to anthracene, preferably at the 9-position. An aromatic anthracenediamine is a compound in which two diarylamine groups are directly attached to anthracene, preferably at the 9- and 10-positions. Aromatic pyreneamines, aromatic pyrenediamines, aromatic chrysamines, and aromatic chrysenediamines are similarly defined, with the diarylamine groups preferably attached to the 1- or 1,6-positions of the pyrene group.

[0114] Examples, also preferred examples, of singlet emitters based on vinylamines and aromatic amines can be found in the following patent documents: WO 2006 / 000388, WO 2006 / 058737, WO 2006 / 000389, WO 2007 / 065549, WO 2007 / 115610, US 7250532 B2, DE 102005058557 A1, CN 1583691 A, JP 08053397 A, US 6251531 B1, US 2006 / 210830 A, EP 1957606 A1 and US 2008 / 0113101 A1. The entire contents of the above-mentioned patent documents are hereby incorporated herein by reference.

[0115] Examples of singlet emitters based on stilbene and its derivatives are disclosed in US Pat. No. 5,121,029.

[0116] Further preferred singlet emitters can be selected from indenofluorene-amines and indenofluorene-diamines, as disclosed in WO 2006 / 122630, benzindenofluorene-amines and benzindenofluorene-diamines, as disclosed in WO 2008 / 006449, and dibenzoindenofluorene-amines and dibenzoindenofluorene-diamines, as disclosed in WO 2007 / 140847.

[0117] Further preferred singlet emitters can be selected from fluorene-based fused ring systems, such as those disclosed in US2015333277A1, US2016099411A1, and US2016204355A1.

[0118] More preferred singlet emitters can be selected from pyrene derivatives, such as the structure disclosed in US2013175509A1; triarylamine derivatives of pyrene, such as the triarylamine derivatives of pyrene containing dibenzofuran units disclosed in CN102232068B; other triarylamine derivatives of pyrene with specific structures, such as those disclosed in CN105085334A and CN105037173A. Other materials that can be used as singlet emitters are polycyclic aromatic hydrocarbon compounds, especially derivatives of the following compounds: anthracene such as 9,10-bis(2-naphthoanthracene), naphthalene, tetraphenyl, xanthene, phenanthrene, pyrene (such as 2,5,8,11-tetra-t-butylperylene), indenopyrene, phenylene such as (4,4'-bis(9-ethyl-3-carbazolylvinyl)-1,1'-biphenyl), diindenopyrene, decacyclopentane, hexabenzophenone, fluorene, spirobifluorene, Arylpyrene (such as US20060222886), arylene vinyl (such as US5121029, US5130603), cyclopentadiene such as tetraphenylcyclopentadiene, rubrene, coumarin, rhodamine, quinacridone, pyran such as 4 (dicyanomethylene) -6- (4-dimethylaminophenylvinyl-2-methyl) -4H-pyran (DCM), thiopyran, bis (azinyl) imine boron compounds (US 2007 / 0092753 A1), bis(azinyl)methylene compounds, carbostyryl compounds, oxazinones, benzoxazoles, benzothiazoles, benzimidazoles and dione pyrrolopyrroles, indolecarbazolyl derivatives (WO2019111971A1, WO2020250961A1, US2020212315A1). Some singlet emitter materials can be found in the following patent documents: US 20070252517 A1, US 4769292, US 6020078, US 2007 / 0252517 A1, US 2007 / 0252517 A1. The entire contents of the above-listed patent documents are hereby incorporated herein by reference.

[0119] Some examples of suitable singlet emitters are listed below:

[0120] 3.TADF materials

[0121] Traditional organic fluorescent materials can only utilize 25% of singlet excitons formed by electrical excitation to emit light, and the internal quantum efficiency of the device is low (up to 25%). Although phosphorescent materials enhance intersystem crossing due to the strong spin-orbit coupling of heavy atom centers, they can effectively utilize singlet excitons and triplet excitons formed by electrical excitation to emit light, so that the internal quantum efficiency of the device reaches 100%. However, the high cost of phosphorescent materials, poor material stability, and severe device efficiency roll-off limit their application in OLEDs. Thermally activated delayed fluorescence luminescent materials are the third generation of organic light-emitting materials developed after organic fluorescent materials and organic phosphorescent materials. This type of material generally has a small singlet-triplet energy level difference (ΔE ST ), triplet excitons can be converted to singlet excitons through antisystem crossing to emit light. This fully utilizes both singlet and triplet excitons formed by electrical excitation, achieving a device internal quantum efficiency of 100%. Furthermore, the material boasts controllable structure, stable properties, low cost, and the absence of precious metals, promising broad application prospects in the OLED field.

[0122] TADF materials need to have a small singlet-triplet energy level difference, preferably ΔE ST <0.3eV, the next best is ΔE ST <0.2eV, preferably ΔE ST <0.1eV. In a preferred embodiment, the TADF material has a relatively small ΔE STIn another preferred embodiment, TADF has a good fluorescence quantum efficiency. Some TADF luminescent materials can be found in the following patent documents: CN103483332(A), TW201309696(A), TW201309778(A), TW201343874(A), TW201350558(A), US20120217869(A1), WO2013133359(A1), WO2013154064(A1), Adachi, et.al. Adv. Mater.,21,2009,4802,Adachi,et.al.Appl.Phys.Lett.,98,2011,083302,Adachi,et.al.Appl.Phys.Lett.,101,2012,093306,Adachi,et.al.Chem.Commun.,48,2012,11392,Adachi,et.al.Nature Photonics,6,2012,253,Adachi,et.al.Nature,492,2012,234,Adachi,et.al.J.Am.Chem.Soc,134,2012,14706,Adachi,et.al.Angew.Chem. Int.Ed,51,2012,11311,Adachi,et.al.Chem.Commun.,48,2012,9580,Adachi,et.al.Chem.Commun.,48,2013,10385,Adachi,et.al.Adv.Mate r., 25, 2013, 3319, Adachi, et.al. Adv. Mater., 25, 2013, 3707, Adachi, et.al. Chem. Mater., 25, 2013, 3038, Adachi, et.al. Chem. Mater., 25, 2013, 3766, Adachi, et.al. J. Mater. Chem. C., 1, 2013, 4599, Adachi, et.al. J. Phys. Chem. A., 117, 2013, 5607, the entire contents of the above-listed patents or article documents are hereby incorporated herein by reference.

[0123] Some examples of suitable TADF emitters are listed below:

[0124] 4.HTM materials

[0125] Suitable organic HTM materials may include compounds having the following structural units: phthalocyanine, porphyrin, amine, aromatic amine, biphenyl triarylamine, thiophene, thiophene, pyrrole, aniline, carbazole, indolizine and fluorene, and their derivatives.

[0126] Examples of cyclic aromatic amine derivative compounds useful as HTMs include, but are not limited to, the following general structure:

[0127] Each Ar 1 -Ar 9 Can be independently selected from cyclic aromatic hydrocarbon compounds, such as benzene, biphenyl, triphenyl, benzo, naphthalene, anthracene, phenanthene, phenanthren, fluorene, pyrene, chrysene, perylene, azulene; aromatic heterocyclic compounds, such as dibenzothiophene, dibenzofuran, furan, thiophene, benzofuran, benzothiophene, carbazole, pyrazole, imidazole, triazole, isoxazole, thiazole, oxadiazole, oxatriazole, dioxazole, thiadiazole, pyridine, pyridazine, pyrimidine, pyrazine, triazine, oxazine, oxathiazine, oxadiazine, indole, benzimidazole, indazole, indoleazine, benzoxazole, benzisoxazole, benzothiazole, quinoline, isoquinoline, o-naphthylene, quinazoline, Quinoxaline, naphthalene, phthalide, pteridine, xanthene, acridine, phenazine, phenothiazine, phenoxazine, dibenzoselenophene, benzoselenophene, benzofuranpyridine, indolecarbazole, pyridineindole, pyrroledipyridine, furandipyridine, benzothiophenepyridine, thiophenepyridine, benzoselenophenepyridine and selenophenedipyridine; containing groups with 2 to 10 ring structures, which can be the same or different types of cyclic aromatic hydrocarbon groups or aromatic heterocyclic groups, and are directly or through at least one of the following groups linked together, such as oxygen atoms, nitrogen atoms, sulfur atoms, silicon atoms, phosphorus atoms, boron atoms, chain structure units and aliphatic ring groups. Among them, Ar 1 -Ar 9 It may be further substituted, and the substituents may be selected from hydrogen, deuterium, alkyl, alkoxy, amino, alkene, alkyne, aralkyl, heteroalkyl, aryl and heteroaryl.

[0128] In one aspect, Ar 1 -Ar 9 Can be independently selected from the group comprising the following structural units:

[0129] X 1 -X 8 is CH or N; Ar 10 Same definition as Ar 1 ; The definition of n is the same as above.

[0130] Additional examples of cyclic aromatic amine derivative compounds can be found in US Pat. Nos. 3,567,450, 4,720,432, 5,061,569, 3,615,404 and 5,061,569.

[0131] Examples of suitable HTM compounds are listed below:

[0132] The present invention also relates to a composition comprising at least one organic compound or mixture as described above, and at least one organic solvent; the at least one organic solvent is selected from aromatic or heteroaromatic compounds, esters, aromatic ketones or aromatic ethers, aliphatic ketones or aliphatic ethers, alicyclic or olefinic compounds, or borate or phosphate compounds, or a mixture of two or more solvents.

[0133] In a preferred embodiment, according to the composition of the present invention, the at least one organic solvent is selected from aromatic or heteroaromatic based solvents.

[0134] 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-methylisopropylbenzene, dipentylbenzene, tripentylbenzene, pentyltoluene, o-diethylbenzene, m-diethylbenzene, p-diethylbenzene, 1,2,3,4-tetramethylbenzene, 1,2,3,5-tetramethylbenzene, 1,2,4,5-tetramethylbenzene, butylbenzene, dodecylbenzene, dihexylbenzene, dibutylbenzene, p-diisopropylbenzene, cyclohexylbenzene, benzylbutylbenzene, dimethylnaphthalene, 3-Isopropylbiphenyl, p-methylisopropylbenzene, 1-methylnaphthalene, 1,2,4-trichlorobenzene, 4,4-difluorodiphenylmethane, 1,2-dimethoxy-4-(1-propenyl)benzene, diphenylmethane, 2-phenylpyridine, 3-phenylpyridine, N-methyldiphenylamine, 4-isopropylbiphenyl, α,α-dichlorodiphenylmethane, 4-(3-phenylpropyl)pyridine, benzyl benzoate, 1,1-bis(3,4-dimethylphenyl)ethane, 2-isopropylnaphthalene, quinoline, isoquinoline, methyl 2-furoate, ethyl 2-furoate, etc.

[0135] Examples of aromatic ketone-based solvents suitable for the present invention include, but are not limited to: 1-tetralone, 2-tetralone, 2-(phenylepoxy)tetralone, 6-(methoxy)tetralone, acetophenone, propiophenone, benzophenone, and their derivatives, such as 4-methylacetophenone, 3-methylacetophenone, 2-methylacetophenone, 4-methylpropiophenone, 3-methylpropiophenone, 2-methylpropiophenone, etc.

[0136] Examples of aromatic ether-based 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-ethylhexyl ether, 1,3-dipropoxybenzene, 1,2,4-trimethoxybenzene, 4-(1-propenyl)-1,2-dimethoxybenzene, 1,3-dimethoxybenzene, glycidyl phenyl ether, dibenzyl ether, 4-tert-butylanisole, trans-p-propenylanisole, 1,2-dimethoxybenzene, 1-methoxynaphthalene, diphenyl ether, 2-phenoxymethyl ether, 2-phenoxytetrahydrofuran, and ethyl-2-naphthyl ether.

[0137] In some preferred embodiments, according to the composition of the present invention, the at least one solvent can be selected from: aliphatic ketones, for example, 2-nonanone, 3-nonanone, 5-nonanone, 2-decanone, 2,5-hexanedione, 2,6,8-trimethyl-4-nonanone, fenchone, phorone, isophorone, di-n-amyl ketone, etc.; or aliphatic ethers, for example, amyl ether, hexyl ether, dioctyl ether, ethylene glycol dibutyl ether, diethylene glycol diethyl ether, diethylene glycol butyl methyl ether, diethylene glycol dibutyl ether, triethylene glycol dimethyl ether, triethylene glycol ethyl methyl ether, triethylene glycol butyl methyl ether, tripropylene glycol dimethyl ether, tetraethylene glycol dimethyl ether, etc.

[0138] In other preferred embodiments, according to the composition of the present invention, the at least one solvent can be selected from ester-based solvents: alkyl octanoate, alkyl sebacate, alkyl stearate, alkyl benzoate, alkyl phenylacetate, alkyl cinnamate, alkyl oxalate, alkyl maleate, alkyl lactone, alkyl oleate, etc. Octyl octanoate, diethyl sebacate, diallyl phthalate, and isononyl isononanoate are particularly preferred.

[0139] The solvent can be used alone or as a mixture of two or more organic solvents.

[0140] In certain preferred embodiments, a composition according to the present invention comprises at least one organic compound or polymer or mixture as described above and at least one organic solvent, and may further comprise another organic solvent. Examples of the other 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.

[0141] In some preferred embodiments, solvents particularly suitable for the present invention are solvents having a Hansen solubility parameter within the following ranges:

[0142] δd (dispersion force) is in the range of 17.0 to 23.2 MPa1 / 2, especially in the range of 18.5 to 21.0 MPa1 / 2;

[0143] δp (polar force) is in the range of 0.2 to 12.5 MPa1 / 2, especially in the range of 2.0 to 6.0 MPa1 / 2;

[0144] δh (hydrogen bond strength) is in the range of 0.9 to 14.2 MPa1 / 2, and particularly in the range of 2.0 to 6.0 MPa1 / 2.

[0145] In the composition of the present invention, the organic solvent should be selected based on its boiling point. In the present invention, the boiling point of the organic solvent is ≥150°C; preferably ≥180°C; more preferably ≥200°C; even more preferably ≥250°C; and most preferably ≥275°C or ≥300°C. Boiling points within these ranges are beneficial for preventing nozzle clogging in inkjet printheads. The organic solvent can be evaporated from the solvent system to form a film containing the functional material.

[0146] In a preferred embodiment, the composition according to the present invention is a solution.

[0147] In another preferred embodiment, the composition according to the present invention is a suspension.

[0148] The compositions of the present invention may comprise 0.01 to 10 wt % of the compound or mixture according to the present invention, preferably 0.1 to 15 wt %, more preferably 0.2 to 5 wt %, and most preferably 0.25 to 3 wt %.

[0149] The present invention also relates to the use of the composition as a coating or printing ink in the preparation of organic electronic devices, and particularly preferably a preparation method by printing or coating.

[0150] Suitable printing or coating techniques include, but are not limited to, inkjet printing, nozzle printing, letterpress printing, screen printing, dip coating, spin coating, doctor blade coating, roller printing, twist roll printing, offset printing, flexographic printing, rotary printing, spray coating, brush or pad printing, and slot extrusion coating. Gravure printing, nozzle printing, and inkjet printing are preferred. The solution or suspension may further include one or more components, such as surfactants, lubricants, wetting agents, dispersants, hydrophobic agents, and adhesives, to adjust viscosity, film-forming properties, and enhance adhesion. Relevant printing techniques and their associated requirements for the relevant solutions, such as solvent, concentration, and viscosity, are discussed in detail.

[0151] The present invention also provides use of the aromatic amine compound, mixture, or composition described above in an organic electronic device. The organic electronic device may be selected from, but not limited to, an organic light-emitting diode (OLED), an organic photovoltaic cell (OPV), an organic light-emitting cell (OLEEC), an organic field-effect transistor (OFET), an organic light-emitting field-effect transistor (OLED), an organic laser, an organic spintronic device, an organic sensor, and an organic plasmon emitting diode (OPED), with OLEDs being particularly preferred. In embodiments of the present invention, the aromatic amine compound is preferably used in the hole transport layer of an OLED device.

[0152] The present invention further relates to an organic electronic device comprising at least one functional layer, wherein the functional layer comprises an organic compound, mixture, or composition as described above. Furthermore, the organic electronic device comprises a cathode, an anode, and at least one functional layer, wherein the functional layer comprises an aromatic amine compound, mixture, or composition as described above. The functional layer is selected from a hole injection layer (HIL), a hole transport layer (HTL), an emissive layer (EML), an electron blocking layer (EBL), an electron injection layer (EIL), an electron transport layer (ETL), and a hole blocking layer (HBL); preferably, the functional layer is selected from a hole transport layer.

[0153] The organic electronic device can be selected from, but not limited to, organic light emitting diodes (OLEDs), organic photovoltaic cells (OPVs), organic light emitting cells (OLEECs), organic field effect transistors (OFETs), organic light emitting field effect transistors, organic lasers, organic spintronic devices, organic sensors, and organic plasmon emitting diodes (OPDs). Particularly preferred are organic electroluminescent devices, such as OLEDs, OLEECs, and organic light emitting field effect transistors.

[0154] The organic electronic device described above, especially the OLED, includes a substrate, an anode, at least one light-emitting layer, and a cathode.

[0155] The substrate can be opaque or transparent. A transparent substrate can be used to make a transparent light-emitting element. For example, see Bulovic et al. Nature 1996, 380, p29, and Gu et al., Appl. Phys. Lett. 1996, 68, p2606. The substrate can be rigid or elastic. The substrate can be plastic, metal, semiconductor wafer or glass. It is best if the substrate has a smooth surface. Substrates without surface defects are particularly ideal. In a preferred embodiment, the substrate is flexible and can be selected from a polymer film or plastic with a glass transition temperature Tg of above 150°C, preferably above 200°C, more preferably above 250°C, and most preferably above 300°C. Examples of suitable flexible substrates are polyethylene terephthalate (PET) and polyethylene (2,6-naphthalene) (PEN).

[0156] The anode may comprise a conductive metal or metal oxide, or a conductive polymer. The anode can readily inject holes into the hole injection layer (HIL), hole transport layer (HTL), or light-emitting layer. In a preferred embodiment, the absolute value of the difference between the work function of the anode and the HOMO energy level or valence band energy level of the light-emitting material 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), and the like. Other suitable anode materials are known and can be readily selected for use by one of ordinary skill in the art. The anode material can be deposited using any suitable technique, such as a suitable physical vapor deposition method, including radio frequency magnetron sputtering, vacuum thermal evaporation, electron beam (e-beam), and the like. In certain embodiments, the anode is patterned. Patterned ITO conductive substrates are commercially available and can be used to prepare devices according to the present invention.

[0157] The cathode may comprise a conductive metal or metal oxide. The cathode can readily inject electrons into the EIL or ETL or directly into the light-emitting layer. In one embodiment, the absolute value of the difference between the work function of the cathode and the LUMO energy level or conduction band energy level of the luminophore in the light-emitting layer or the n-type semiconductor material serving as the electron injection layer (EIL) or 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 cathodes in OLEDs may be used as cathode materials for the devices of the present invention. Examples of cathode materials include, but are not limited to, Al, Au, Ag, Ca, Ba, Mg, LiF / Al, MgAg alloys, BaF2 / Al, Cu, Fe, Co, Ni, Mn, Pd, Pt, ITO, and the like. The cathode material may be deposited using any suitable technique, such as a suitable physical vapor deposition method, including radio frequency magnetron sputtering, vacuum thermal evaporation, electron beam (e-beam), and the like.

[0158] OLEDs may also include other functional layers, such as a hole injection layer (HIL), a hole transport layer (HTL), an electron blocking layer (EBL), an electron injection layer (EIL), an electron transport layer (ETL), and a hole blocking layer (HBL). Materials suitable for use in these functional layers are described in detail above and in WO2010135519A1, US20090134784A1, and WO2011110277A1, the entire contents of which are hereby incorporated by reference.

[0159] Another aspect of the present invention relates to an organic electroluminescent device, comprising a first electrode, a second electrode, and one or more organic layers between the first electrode and the second electrode, wherein at least one organic layer comprises an organic compound represented by general formula (I) or general formula (II). In some preferred embodiments, the organic electroluminescent device comprises: a first electrode; a hole transport region disposed on the first electrode; a light-emitting layer disposed on the hole transport region; an electron transport region disposed on the light-emitting layer; and a second electrode disposed on the electron transport region; wherein the hole transport region comprises at least one organic compound or mixture as described above. In some more preferred embodiments, the hole transport region has a multilayer structure, and the layer in contact with the light-emitting layer in the multilayer structure comprises an organic compound or mixture as described above. In some more preferred embodiments, the hole transport region comprises: a hole injection layer disposed on the first electrode, a hole transport layer disposed on the hole injection layer, and a hole auxiliary layer disposed on the hole transport layer, wherein the hole auxiliary layer comprises an organic compound or mixture as described above.

[0160] The organic electroluminescent device can be manufactured using suitable materials known in the art by suitable methods known in the art, except that the organic compound of formula (I) or formula (II) forms the corresponding organic layer.

[0161] The organic layer of the organic electroluminescent device according to the present invention has a single layer or multilayer structure. For example, the organic layer can be a hole injection layer, a hole transport layer, a hole auxiliary layer, a light-emitting layer, an electron transport layer, and an electron injection layer. However, the number of organic layers is not limited and can be increased or decreased.

[0162] According to one embodiment of the present invention, an organic electroluminescent device may include a substrate, a first electrode, a first hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, and a second electrode, wherein a hole-assisting layer comprising a compound represented by general formula (I) or (II) is interposed between the hole transport layer and the light-emitting layer. The presence of the compound represented by general formula (I) or (II) facilitates hole transport to the light-emitting layer, thereby further improving the luminous efficiency and lifespan characteristics of the device.

[0163] A more detailed description will be given below on embodiments of the organic electroluminescent device according to the present invention.

[0164] The organic electroluminescent device of the present invention comprises an anode, a hole transport layer, a light-emitting layer, an electron transport layer, and a cathode. The organic electroluminescent device of the present invention may also optionally include a hole injection layer between the anode and the hole transport layer and an electron injection layer between the electron transport layer and the cathode. If necessary, the organic electroluminescent device of the present invention may also include one or two intermediate layers. The intermediate layer may be a hole blocking layer or an electron blocking layer. The organic electroluminescent device of the present invention may also include one or more organic layers having various functions according to the desired characteristics of the device.

[0165] The organic electroluminescent device of the present invention may further include a hole-assisting layer between the hole-transporting layer and the light-emitting layer, wherein the hole-assisting layer may include a compound represented by formula (I) or formula (II).

[0166] According to the organic electroluminescent device of the present invention, the emission wavelength is between 300 and 1200 nm, preferably between 350 and 1000 nm, more preferably between 400 and 900 nm, and most preferably between 450 and 650 nm.

[0167] The present invention also relates to applications of the organic electroluminescent 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.

[0168] 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 summarize the scope of the present invention. Under the guidance of the concept of the present invention, those skilled in the art should realize that certain changes made to the various embodiments of the present invention will be covered by the spirit and scope of the claims of the present invention.

[0169] Specific embodiments

[0170] 1. Synthesis of compounds

[0171] Synthesis of Compound 1-1: In a dry two-necked flask, 1-bromo-2-methoxynaphthalene (16 g, 67.48 mmol), 4-dibenzofuranboronic acid (17.16 g, 80.98 mmol), and tetrakistriphenylphosphine palladium (4.0 g, 3.46 mmol) were added. The mixture was dissolved in 50 mL of 2M potassium carbonate solution and 150 mL of 1,4-dioxane. The mixture was evacuated and refilled with nitrogen three times, and stirred at 80°C overnight. After the reaction, the mixture was cooled to room temperature, separated, and the organic phase was added to a silica gel column (n-hexane:dichloromethane = 4:1). The resulting mixture was concentrated to yield 18.4 g, with a yield of 84%. MS (ASAP) = 324.4.

[0172] Synthesis of Compound 1-2: Add compound 1-1 (16 g, 49.32 mmol) to a dry two-necked flask and dissolve in 500 mL of dichloromethane. Evacuate and replace the atmosphere with nitrogen three times. Cool to -50°C and slowly add boron tribromide (14.83 g, 17.80 mmol) dropwise. Allow to warm to room temperature and stir overnight. After the reaction, cool and quench the reaction by adding methanol. Concentrate the mixture, dissolve in dichloromethane, decolorize on silica gel, and concentrate the mother liquor to yield 15 g (100% yield). MS (ASAP) = 310.4.

[0173] Synthesis of Compound 1-3: Compound 1-2 (16 g, 51.55 mmol) was weighed into a reaction flask and dissolved in 250 mL of dichloromethane. The mixture was evacuated and purged with nitrogen three times. The temperature was lowered to -10°C, and triethylamine (10.43 g, 103.1 mmol) was added. Stir for 30 minutes, followed by trifluoromethanesulfonic anhydride (29.08 g, 103.1 mmol). The mixture was gradually warmed to room temperature and stirred overnight. After the reaction, 100 mL of water was added and stirred for 30 minutes. The aqueous layer was separated, and the organic layer was directly passed through a short silica gel column. The mother liquor was concentrated to yield 19.0 g, an 83% yield. MS (ASAP) = 442.41.

[0174] Synthesis of Compound 1: In a dry two-necked flask, N,N-bis(4-biphenyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (20.5 g, 39.16 mmol), compound 1-3 (19.06 g, 43.08 mmol), and tetrakistriphenylphosphine palladium (2.26 g, 1.96 mmol) were added. 80 mL of 2M aqueous potassium carbonate solution and 240 mL of 1,4-dioxane were then added. The mixture was evacuated and refilled with nitrogen three times, and stirred at 80°C overnight. After completion of the reaction, the mixture was cooled to room temperature. After separation, the organic phase was added with n-hexane until saturated, rapidly decolorized by passing through a short column of silica gel, and concentrated to obtain a solid. This solid was recrystallized from toluene to yield 14.0 g, a 52% yield. MS (ASAP) = 689.9.

[0175] Synthesis of Compound 2-1: 1-Bromo-2-methoxynaphthalene (16 g, 67.48 mmol), 1-dibenzofuranboronic acid (17.16 g, 80.98 mmol), and tetrakistriphenylphosphine palladium (4.0 g, 3.46 mmol) were added to a dry two-necked flask. The mixture was dissolved in 2M aqueous potassium carbonate (160 mL) and 1,4-dioxane (300 mL). The mixture was evacuated and refilled with nitrogen three times. The reaction was stirred at 80°C overnight. The aqueous phase was separated while hot, and the organic phase was concentrated onto a silica gel column using an 8:1 ratio of n-hexane:dichloromethane to flush out the impurities above. The product was then flushed out with a 5:1 ratio of n-hexane:dichloromethane. The product was concentrated to yield 17.7 g, with a yield of 81%. MS (ASAP) = 324.4.

[0176] Synthesis of Compound 2-2: Add Compound 2-1 (16 g, 49.32 mmol) to a dry two-necked flask and dissolve in 500 mL of dichloromethane. Evacuate and replace the atmosphere with nitrogen three times. Cool to -50°C and slowly add boron tribromide (14.83 g, 17.80 mmol) dropwise. Allow to warm to room temperature and stir overnight. After the reaction, cool and quench the reaction by adding methanol. Concentrate the mixture, dissolve in dichloromethane, decolorize on silica gel, and concentrate the mother liquor to yield 15 g (100% yield). MS (ASAP) = 310.4.

[0177] Synthesis of Compound 2-3: Compound 2-2 (16 g, 51.55 mmol) was weighed into a reaction flask and dissolved in 250 mL of dichloromethane. The mixture was evacuated and nitrogen was circulated three times. The temperature was lowered to -10°C, and triethylamine (10.43 g, 103.1 mmol) was added. Stir for 30 minutes, followed by trifluoromethanesulfonic anhydride (29.08 g, 103.1 mmol). The mixture was gradually warmed to room temperature and stirred overnight. After the reaction, 100 mL of water was added and stirred for 30 minutes. The aqueous layer was separated, and the organic layer was directly passed through a short silica gel column. The mother liquor was concentrated to yield 20.8 g, a 91% yield. MS (ASAP) = 442.41.

[0178] Synthesis of Compound 2: In a dry two-necked flask, N,N-bis(4-biphenyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (20.5 g, 39.16 mmol), compound 2-3 (19.06 g, 43.08 mmol), and tetrakistriphenylphosphine palladium (2.26 g, 1.96 mmol) were added. Then, 200 mL of 2M aqueous potassium carbonate solution and 500 mL of 1,4-dioxane were added. The mixture was evacuated and refilled with nitrogen three times, and the reaction was stirred at 80°C overnight. After the reaction, the mixture was cooled to room temperature. After separation, the organic phase was added with n-hexane until saturated, rapidly decolorized by passing through a short column of silica gel, and concentrated to obtain a solid. This solid was recrystallized from toluene to yield 18.4 g, a 68% yield. MS (ASAP) = 689.9.

[0179] Synthesis of Compound 3-1: In a dry reaction flask, add 4-bromobenzo[2,1-b:3,4-b']bisbenzofuran (synthesis method, see CN110655438A) (20.2g, 60mmol), pinacol diboron (16.8g, 66mol), potassium acetate (28.3g, 300mmol), [1,1'-bis(diphenylphosphino)ferrocene]palladium dichloride (2.18g, 3mmol), and 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl (1.43g, 3mmol). 250mL of 1,4-dioxane was added to dissolve the mixture. After evacuation and nitrogen replacement three times, the reaction was carried out at 85°C overnight. After completion of the reaction, the mixture was cooled to room temperature, filtered, and the mother liquor was concentrated. The solution was then cleared with dichloromethane and passed through a short silica gel column for decolorization. The mother liquor was then concentrated. After slurrying with ethanol, the product was filtered to obtain 19.6 g, with a yield of 85%. MS (ASAP) = 384.2.

[0180] Synthesis of Compound 3-2: 1-Bromo-2-methoxynaphthalene (11.8 g, 50 mmol), Compound 3-1 (19.2 g, 50 mmol), and tetrakistriphenylphosphine palladium (2.89 g, 2.5 mmol) were added to a dry two-necked flask. The mixture was dissolved in 25 mL of 2M aqueous potassium carbonate solution and 100 mL of 1,4-dioxane. The mixture was evacuated and filled with nitrogen three times. The reaction was stirred at 80°C overnight. After separation, the organic phase was added to a silica gel column (n-hexane:dichloromethane = 3:1) and concentrated to yield 18.0 g, with a yield of 87%. MS (ASAP) = 414.4

[0181] Synthesis of Compound 3-3: Compound 3-2 (16.6 g, 40 mmol) was added to a dry two-necked flask and dissolved in 250 mL of dichloromethane. The atmosphere was evacuated and replaced with nitrogen three times. The temperature was lowered to -50°C, and boron tribromide (12.0 g, 14.4 mmol) was slowly added dropwise. The temperature was naturally raised to room temperature, and the reaction was stirred overnight. After the reaction, the temperature was lowered and methanol was added to quench the reaction. The solution was concentrated, dissolved in dichloromethane, and decolorized on silica gel. The mother liquor was concentrated to yield 16.0 g (100% yield). MS (ASAP) = 400.4.

[0182] Synthesis of Compound 3-4: Compound 3-3 (16.0 g, 40 mmol) was weighed into a reaction flask and dissolved in 250 mL of dichloromethane. The mixture was evacuated and nitrogen was circulated three times. The temperature was lowered to -10°C, and triethylamine (8.10 g, 80 mmol) was added. Stir for 30 minutes, followed by trifluoromethanesulfonic anhydride (22.6 g, 80 mmol). The mixture was gradually warmed to room temperature and stirred overnight. After the reaction, 100 mL of water was added and stirred for 30 minutes. The aqueous layer was separated, and the organic layer was directly passed through a short silica gel column. The mother liquor was concentrated to yield 19.0 g, an 89% yield. MS (ASAP) = 532.5.

[0183] Synthesis of Compound 3: In a dry two-necked flask, N,N-bis(4-biphenyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (20.1 g, 38.5 mmol), compound 3-4 (18.6 g, 35 mmol), and tetrakistriphenylphosphine palladium (2.02 g, 1.75 mmol) were added. Then, 50 mL of 2M aqueous potassium carbonate solution and 250 mL of 1,4-dioxane were added. The mixture was evacuated and refilled with nitrogen three times, and stirred at 80°C overnight. After the reaction, the mixture was cooled to room temperature. The organic phase was separated and concentrated onto a silica gel column (n-hexane:dichloromethane = 2:1). The product was concentrated to yield 23.7 g, with a yield of 87%. MS (ASAP) = 779.9.

[0184] Synthesis of Compound 4-1: 1-Bromo-2-methoxynaphthalene (16 g, 67.48 mmol), 2-dibenzofuranboronic acid (17.16 g, 80.98 mmol), and tetrakistriphenylphosphine palladium (4.0 g, 3.46 mmol) were added to a dry two-necked flask. The mixture was dissolved in 120 mL of 2M aqueous potassium carbonate solution and 300 mL of 1,4-dioxane. The mixture was evacuated and refilled with nitrogen three times. The reaction was stirred at 80°C overnight. After separation, the organic phase was added to a silica gel column (n-hexane:dichloromethane = 5:1) and concentrated to yield 19.0 g, with a yield of 87%. MS (ASAP) = 324.4.

[0185] Synthesis of Compound 4-2: Add compound 4-1 (16 g, 49.32 mmol) to a dry two-necked flask and dissolve in 500 mL of dichloromethane. Evacuate and replace the atmosphere with nitrogen three times. Cool to -50°C and slowly add boron tribromide (14.83 g, 17.80 mmol) dropwise. Allow to warm to room temperature and stir overnight. After the reaction, cool and quench the reaction by adding methanol. Concentrate the mixture, dissolve in dichloromethane, decolorize on silica gel, and concentrate the mother liquor to yield 15 g (100% yield). MS (ASAP) = 310.4.

[0186] Synthesis of Compound 4-3: Compound 4-2 (16 g, 51.55 mmol) was weighed into a reaction flask and dissolved in 250 mL of dichloromethane. The mixture was evacuated and purged with nitrogen three times. The temperature was lowered to -10°C, and triethylamine (10.43 g, 103.1 mmol) was added. Stir for 30 minutes, followed by trifluoromethanesulfonic anhydride (29.08 g, 103.1 mmol). The mixture was gradually warmed to room temperature and stirred overnight. After the reaction, 100 mL of water was added and stirred for 30 minutes. The aqueous layer was separated, and the organic layer was directly passed through a short silica gel column. The mother liquor was concentrated to yield 19.4 g, an 85% yield. MS (ASAP) = 442.41.

[0187] Synthesis of Compound 4-4: 1-Bromo-4-chloro-2-iodobenzene (15.9 g, 50 mmol), phenylboronic acid (6.10 g, 50 mmol), and tetrakistriphenylphosphine palladium (2.89 g, 2.5 mmol) were added to a dry two-necked flask. 30 mL of 2M potassium carbonate solution and 120 mL of 1,4-dioxane were added to dissolve the mixture. The mixture was evacuated and refilled with nitrogen three times, and the reaction was stirred at 80°C overnight. After the reaction was completed, the mixture was cooled to room temperature, separated, and the solvent was removed by vacuum distillation. The mixture was then dissolved in dichloromethane, washed with water, and the organic phases were combined and dried over anhydrous sodium sulfate. Excess solvent was removed by vacuum distillation. The mixture was then purified by silica gel column chromatography (petroleum ether:dichloromethane = 4:1) to obtain 11.4 g of the desired product in an approximately 85% yield. MS (ASAP) = 267.6.

[0188] Synthesis of Compound 4-5: Compound 4-4 (10.7 g, 40 mmol), di(4-biphenylyl)amine (13.5 g, 42 mmol), tris(dibenzylideneacetone)dipalladium (1.83 g, 2 mmol), tri-tert-butylphosphine (0.81 g, 4 mmol), and sodium tert-butoxide (7.69 g, 80 mmol) were added to a dry two-necked flask and dissolved in 120 mL of anhydrous toluene. The mixture was evacuated and refilled with nitrogen three times, then heated to reflux and reacted overnight. After the reaction, the mixture was cooled to room temperature, separated, and the solvent was removed by vacuum distillation. The mixture was then dissolved in dichloromethane, washed with water, and the organic phases were combined, dried over anhydrous sodium sulfate, and the excess solvent was removed by vacuum distillation. The mixture was then purified by silica gel column chromatography (petroleum ether:dichloromethane = 3:1) to obtain 15.2 g of the desired product in an approximately 75% yield. MS (ASAP) = 508.1.

[0189] Synthesis of Compound 4-6: To a dry reaction flask were added Compound 4-5 (15.2 g, 30 mmol), pinacol diboron (8.38 g, 33 mol), potassium acetate (14.7 g, 150 mmol), [1,1'-bis(diphenylphosphino)ferrocene]palladium dichloride (1.09 g, 1.5 mmol), and 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl (0.72 g, 1.5 mmol). 150 mL of 1,4-dioxane was added for dissolution. The reaction was evacuated and replaced with nitrogen three times. The reaction was allowed to proceed at 85°C overnight. After completion of the reaction, the reaction was cooled to room temperature, filtered, and the mother liquor was concentrated. The mother liquor was then cleared with dichloromethane and passed through a short silica gel column for decolorization. The mother liquor was then concentrated. The mixture was slurried with ethanol and filtered to yield 14.0 g, with a yield of 78%. MS (ASAP) = 599.6.

[0190] Synthesis of Compound 4: Compound 4-6 (12.0 g, 20 mmol), compound 4-3 (9.73 g, 22 mmol), and tetrakistriphenylphosphine palladium (1.16 g, 1 mmol) were added to a dry two-necked flask. 25 mL of 2M potassium carbonate solution and 100 mL of 1,4-dioxane were added for dissolution. The mixture was vacuum-filled with nitrogen for three cycles and stirred at 85°C overnight. After the reaction, the mixture was cooled to room temperature, separated, and the solvent removed by vacuum distillation. The mixture was then dissolved in dichloromethane, washed with water, and the organic phases were combined and dried over anhydrous sodium sulfate. Excess solvent was removed by vacuum distillation. The mixture was then purified by silica gel column chromatography (petroleum ether:dichloromethane = 2:1) to obtain 11.8 g of the desired product in an approximately 77% yield. MS (ASAP) = 766.0.

[0191] Synthesis of Compound 5-1: 4-Bromo-1-chloro-2-iodobenzene (15.9 g, 50 mmol), phenylboronic acid (6.10 g, 50 mmol), and tetrakistriphenylphosphine palladium (2.89 g, 2.5 mmol) were added to a dry two-necked flask. 30 mL of 2M potassium carbonate solution and 120 mL of 1,4-dioxane were added to dissolve the mixture. The mixture was evacuated and filled with nitrogen three times, and the reaction was stirred at 80°C overnight. After the reaction was completed, the mixture was cooled to room temperature, separated, and the solvent was removed by vacuum distillation. The mixture was then dissolved in dichloromethane, washed with water, and the organic phases were combined and dried over anhydrous sodium sulfate. Excess solvent was removed by vacuum distillation. The mixture was then purified by silica gel column chromatography (petroleum ether:dichloromethane = 4:1) to obtain 11.6 g of the desired product in an approximately 87% yield. MS (ASAP) = 267.6.

[0192] Synthesis of Compound 5-2: Compound 5-1 (10.7 g, 40 mmol), di(4-biphenylyl)amine (13.5 g, 42 mmol), tris(dibenzylideneacetone)dipalladium (1.83 g, 2 mmol), tri-tert-butylphosphine (0.81 g, 4 mmol), and sodium tert-butoxide (7.69 g, 80 mmol) were added to a dry two-necked flask and dissolved in 120 mL of anhydrous toluene. The mixture was evacuated and refilled with nitrogen three times, then heated to reflux and reacted overnight. After the reaction, the mixture was cooled to room temperature, separated, and the solvent was removed by vacuum distillation. The mixture was then dissolved in dichloromethane, washed with water, and the organic phases were combined, dried over anhydrous sodium sulfate, and the excess solvent was removed by vacuum distillation. The mixture was then purified by silica gel column chromatography (petroleum ether:dichloromethane = 3:1) to obtain 15.2 g of the desired product in an approximately 75% yield. MS (ASAP) = 508.1.

[0193] Synthesis of Compound 5-3: In a dry reaction flask, compound 5-2 (15.2 g, 30 mmol), pinacol diboron (8.38 g, 33 mol), potassium acetate (14.7 g, 150 mmol), [1,1'-bis(diphenylphosphino)ferrocene]palladium dichloride (1.09 g, 1.5 mmol), and 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl (0.72 g, 1.5 mmol) were added. 150 mL of 1,4-dioxane was added to dissolve the mixture. The atmosphere was evacuated and replaced with nitrogen three times. The mixture was reacted at 85°C overnight. After completion of the reaction, the mixture was cooled to room temperature, filtered, and the mother liquor was concentrated. The mixture was then cleared with dichloromethane and passed through a short silica gel column for decolorization. The mother liquor was then concentrated. The mixture was slurried with ethanol and filtered to yield 14.6 g, with a yield of 81%. MS (ASAP) = 599.6.

[0194] Synthesis of Compound 5: Compound 5-3 (12.0 g, 20 mmol), compound 4-3 (9.73 g, 22 mmol), and tetrakistriphenylphosphine palladium (1.16 g, 1 mmol) were added to a dry two-necked flask. 25 mL of 2M potassium carbonate solution and 100 mL of 1,4-dioxane were added for dissolution. The mixture was evacuated and refilled with nitrogen three times, and the reaction was stirred at 85°C overnight. After the reaction was completed, the mixture was cooled to room temperature, separated, and the solvent was removed by vacuum distillation. The mixture was then dissolved in dichloromethane, washed with water, and the organic phases were combined and dried over anhydrous sodium sulfate. Excess solvent was removed by vacuum distillation. The mixture was then purified by silica gel column chromatography (petroleum ether:dichloromethane = 2:1) to obtain 11.8 g of the desired product in an approximately 77% yield. MS (ASAP) = 766.0.

[0195] Synthesis of Compound 6-1: To a dry reaction flask, 1-bromo-2,4-di(phenyl)benzene (18.6 g, 60 mmol), pinacol diboron (16.8 g, 66 mol), potassium acetate (28.3 g, 300 mmol), [1,1'-bis(diphenylphosphino)ferrocene]palladium dichloride (2.18 g, 3 mmol), and 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl (1.43 g, 3 mmol) were added. 250 mL of 1,4-dioxane was added to dissolve the mixture. The atmosphere was evacuated and replaced with nitrogen three times. The reaction was allowed to proceed at 85°C overnight. After completion of the reaction, the mixture was cooled to room temperature, filtered, and the mother liquor was concentrated. The mixture was then cleared with dichloromethane and passed through a short silica gel column for decolorization. The mother liquor was then concentrated. The mixture was slurried with ethanol and filtered to yield 19.5 g, with a yield of 91%. MS (ASAP) = 356.3.

[0196] Synthesis of Compound 6-2: Compound 6-1 (17.8 g, 50 mmol), 4,4'-4"-phenyl-dibromotriphenylamine (24.0 g, 50 mmol), and tetrakistriphenylphosphine palladium (2.89 g, 2.5 mmol) were added to a dry two-necked flask. 30 mL of 2M potassium carbonate solution and 120 mL of 1,4-dioxane were added for dissolution. The mixture was evacuated and filled with nitrogen three times, and the reaction was stirred at 80°C overnight. After the reaction was completed, the mixture was cooled to room temperature, separated, and the solvent was removed by vacuum distillation. The mixture was then dissolved in dichloromethane, washed with water, and the organic phases were combined and dried over anhydrous sodium sulfate. The excess solvent was removed by vacuum distillation. The desired product (24.8 g) was obtained with a yield of approximately 79%. MS (ASAP) = 628.6.

[0197] Synthesis of Compound 6-3: In a dry reaction flask, compound 6-2 (18.9 g, 30 mmol), pinacol diboron (8.38 g, 33 mol), potassium acetate (14.7 g, 150 mmol), [1,1'-bis(diphenylphosphino)ferrocene]palladium dichloride (1.09 g, 1.5 mmol), and 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl (0.72 g, 1.5 mmol) were added. 200 mL of 1,4-dioxane was added for dissolution. The atmosphere was evacuated and replaced with nitrogen three times. The reaction was allowed to proceed at 85°C overnight. After completion of the reaction, the mixture was cooled to room temperature, filtered, and the mother liquor was concentrated. The mixture was then cleared with dichloromethane and passed through a short silica gel column for decolorization. The mother liquor was then concentrated. The mixture was slurried with ethanol and filtered to yield 15.8 g, with a yield of 78%. MS (ASAP) = 675.7.

[0198] Synthesis of Compound 6: Compound 6-3 (13.5 g, 20 mmol), compound 1-3 (9.73 g, 22 mmol), and tetrakistriphenylphosphine palladium (1.16 g, 1 mmol) were added to a dry two-necked flask. 25 mL of 2M potassium carbonate solution and 100 mL of 1,4-dioxane were added for dissolution. The mixture was evacuated and refilled with nitrogen three times, and the reaction was stirred at 85°C overnight. After the reaction was completed, the mixture was cooled to room temperature, separated, and the solvent was removed by vacuum distillation. The mixture was then dissolved in dichloromethane, washed with water, and the organic phases were combined and dried over anhydrous sodium sulfate. Excess solvent was removed by vacuum distillation. The mixture was then purified by silica gel column chromatography (petroleum ether:dichloromethane = 2:1) to obtain 12.5 g of the desired product in an approximately 74% yield. MS (ASAP) = 842.1.

[0199] Synthesis of Compound 7: Compound 4-6 (12.0 g, 20 mmol), compound 1-3 (9.73 g, 22 mmol), and tetrakistriphenylphosphine palladium (1.16 g, 1 mmol) were added to a dry two-necked flask. 25 mL of 2M potassium carbonate solution and 100 mL of 1,4-dioxane were added for dissolution. The mixture was vacuum-filled with nitrogen for three cycles and stirred at 85°C overnight. After the reaction, the mixture was cooled to room temperature, separated, and the solvent removed by vacuum distillation. The mixture was then dissolved in dichloromethane, washed with water, and the organic phases were combined and dried over anhydrous sodium sulfate. Excess solvent was removed by vacuum distillation. The mixture was then purified by silica gel column chromatography (petroleum ether:dichloromethane = 2:1) to obtain 11.8 g of the desired product in an approximately 77% yield. MS (ASAP) = 766.0.

[0200] Synthesis of Compound 8: Compound 5-3 (12.0 g, 20 mmol), compound 1-3 (9.73 g, 22 mmol), and tetrakistriphenylphosphine palladium (1.16 g, 1 mmol) were added to a dry two-necked flask. 25 mL of 2M potassium carbonate solution and 100 mL of 1,4-dioxane were added for dissolution. The mixture was evacuated and refilled with nitrogen three times, and the reaction was stirred at 85°C overnight. After the reaction was completed, the mixture was cooled to room temperature, separated, and the solvent was removed by vacuum distillation. The mixture was then dissolved in dichloromethane, washed with water, and the organic phases were combined and dried over anhydrous sodium sulfate. Excess solvent was removed by vacuum distillation. The mixture was then purified by silica gel column chromatography (petroleum ether:dichloromethane = 2:1) to obtain 11.8 g of the desired product in an approximately 77% yield. MS (ASAP) = 766.0.

[0201] Synthesis of Compound 9: Compound 4-6 (12.0 g, 20 mmol), compound 2-3 (9.73 g, 22 mmol), and tetrakistriphenylphosphine palladium (1.16 g, 1 mmol) were added to a dry two-necked flask. 25 mL of 2M potassium carbonate solution and 100 mL of 1,4-dioxane were added for dissolution. The mixture was evacuated and refilled with nitrogen three times, and the reaction was stirred at 85°C overnight. After the reaction was completed, the mixture was cooled to room temperature, separated, and the solvent was removed by vacuum distillation. The mixture was then dissolved in dichloromethane, washed with water, and the organic phases were combined and dried over anhydrous sodium sulfate. Excess solvent was removed by vacuum distillation. The mixture was then purified by silica gel column chromatography (petroleum ether:dichloromethane = 2:1) to obtain 11.8 g of the desired product in an approximately 77% yield. MS (ASAP) = 766.0.

[0202] Synthesis of compound 10-1: To a dry two-necked flask, 4,4'-dibromo-4"-phenyltriphenylamine (24.0 g, 50 mmol), 4-dibenzofuranboronic acid (10.6 g, 50 mmol), and tetrakistriphenylphosphine palladium (2.89 g, 2.5 mmol) were added. 30 mL of 2M potassium carbonate solution and 120 mL of 1,4-dioxane were added for dissolution. Vacuum and nitrogen were cycled three times, and the reaction was stirred at 80°C overnight. After the reaction was completed, the mixture was cooled to room temperature, separated, and the solvent was removed by vacuum distillation. The mixture was then dissolved in dichloromethane, washed with water, and the organic phases were combined, dried over anhydrous sodium sulfate, and the excess solvent was removed by vacuum distillation. The desired product (22.9 g) was obtained with an approximately 81% yield by column chromatography on silica gel (petroleum ether:dichloromethane = 5:1). MS (ASAP) = 566.5.

[0203] Synthesis of Compound 10-2: Compound 10-1 (22.7 g, 40 mmol), 3-chlorophenylboronic acid (6.57 g, 42 mmol), and tetrakistriphenylphosphine palladium (2.31 g, 2 mmol) were added to a dry two-necked flask. 25 mL of 2M potassium carbonate solution and 100 mL of 1,4-dioxane were added to dissolve the mixture. The mixture was vacuum-filled with nitrogen for three cycles and stirred at 80°C overnight. After the reaction, the mixture was cooled to room temperature, separated, and the solvent was removed by vacuum distillation. The mixture was then dissolved in dichloromethane, washed with water, and the organic phases were combined and dried over anhydrous sodium sulfate. Excess solvent was removed by vacuum distillation. The mixture was then purified by silica gel column chromatography (petroleum ether:dichloromethane = 5:1) to obtain 20.3 g of the desired product in an approximately 85% yield. MS (ASAP) = 598.1.

[0204] Synthesis of Compound 10-3: To a dry reaction flask were added Compound 10-2 (17.9 g, 30 mmol), pinacol diboron (8.38 g, 33 mol), potassium acetate (14.7 g, 150 mmol), [1,1'-bis(diphenylphosphino)ferrocene]palladium dichloride (1.09 g, 1.5 mmol), and 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl (0.72 g, 1.5 mmol). 250 mL of 1,4-dioxane was added for dissolution. The atmosphere was evacuated and replaced with nitrogen three times. The reaction was allowed to proceed at 85°C overnight. After completion of the reaction, the mixture was cooled to room temperature, filtered, and the mother liquor was concentrated. The mixture was then cleared with dichloromethane and passed through a short silica gel column for decolorization. The mother liquor was then concentrated. The mixture was slurried with ethanol and filtered to yield 16.6 g, with a yield of 80%. MS (ASAP) = 689.7.

[0205] Synthesis of Compound 10: Compound 10-3 (13.8 g, 20 mmol), compound 1-3 (9.73 g, 22 mmol), and tetrakistriphenylphosphine palladium (1.16 g, 1 mmol) were added to a dry two-necked flask. 25 mL of 2M potassium carbonate solution and 100 mL of 1,4-dioxane were added for dissolution. The mixture was evacuated and nitrogen was refilled three times. The reaction was stirred at 85°C overnight. After the reaction was completed, the mixture was cooled to room temperature, separated, and the solvent was removed by vacuum distillation. The organic phases were then dissolved in dichloromethane, washed with water, and combined. The organic phases were dried over anhydrous sodium sulfate, and the excess solvent was removed by vacuum distillation. The product was then purified by silica gel column chromatography (petroleum ether:dichloromethane = 2:1) to obtain 13.0 g of the desired product in an approximately 76% yield. MS (ASAP) = 856.0.

[0206] 2. Energy structure of organic compounds

[0207] The energy levels of organic materials can be calculated through quantum calculations, such as using TD-DFT (time-dependent density functional theory) with Gaussian03W (Gaussian Inc.). For detailed simulation methods, see WO2011141110. The molecular geometry is first optimized using the semi-empirical method "Ground State / Semi-empirical / Default Spin / AM1" (Charge 0 / Spin Singlet). The energy structure of the organic molecule is then calculated using TD-DFT (time-dependent density functional theory) using the "TD-SCF / DFT / Default Spin / B3PW91" basis set "6-31G(d)" (Charge 0 / Spin Singlet). The HOMO and LUMO energy levels are calculated using the following calibration formulas, with S1 and T1 used directly.

[0208] HOMO(eV)=((HOMO(G)×27.212)-0.9899) / 1.1206

[0209] LUMO(eV)=((LUMO(G)×27.212)-2.0041) / 1.385

[0210] The HOMO(G) and LUMO(G) are the direct calculation results of Gaussian 03W, and the unit is Hartree. The results are shown in Table 1:

[0211] Table 1

[0212] 3. Preparation and Characterization of OLED Devices

[0213] The preparation process of the above-mentioned OLED device is described in detail below through a specific embodiment. The blue light device structure is HI(10) / HT-1(50) / HT-2(10) / BH:BD=100:3(25) / ET:LiQ=50:50(30) / LiQ(1) / Al(100).

[0214] a. Cleaning of ITO (Indium Tin Oxide) conductive glass substrates: Use various solvents (such as one or more of chloroform, acetone or isopropyl alcohol) to clean, and then perform ultraviolet ozone treatment.

[0215] b. Evaporation: Move the substrate into the vacuum vapor deposition equipment and place it in a high vacuum (1×10 -6At 100 mbar, the ratio of PD to HT-1 was controlled to be 3:100, forming a 10nm hole injection layer (HIL). Compound HT-1 was then evaporated on the hole injection layer to form a 50nm hole transport layer (HTL). The inventive compound was then evaporated on the hole transport layer to form a 10nm hole auxiliary layer. As the light-emitting layer, a 25nm light-emitting layer thin film was formed using a BH:BD ratio of 100:3. Next, a 5nm electron auxiliary layer ET-1 was evaporated. ET-2 and LiQ were then co-deposited in separate evaporation units at a 50wt% ratio, forming a 25nm electron transport layer. Subsequently, 1nm of LiQ was deposited as an electron injection layer. Finally, a 100nm thick Al cathode was deposited on the electron injection layer.

[0216] c. Packaging: The device is encapsulated with UV curable resin in a nitrogen glove box.

[0217] The device performance of the above embodiments and comparative examples was tested, as shown in Table 2. The driving voltage and current efficiency were tested at a current density of 10 mA / cm2. The device life of T95 refers to the time it takes for the brightness to decay to 95% at a constant current density of 50 mA / cm2.

[0218] Table 2

[0219] Compared with Comparative Examples 1 to 6, Device Examples 1 to 8 have lower driving voltages, while both current efficiency and lifespan are significantly improved. It is speculated that the reason is that the arylamine compound substituted at the 2-position of the naphthyl group of the present invention has a bulky naphthyl group substituted with a linking group, which reduces the symmetry of the molecule and inhibits crystallization, thereby improving the film quality. At the same time, the compound of the present invention introduces a specific substituent at the 1-position of the naphthyl group. This substituent has a spatial electron repulsion effect with other 1'-position hydrogen atoms, further reducing the planarity of the molecule, thereby improving hole transport and increasing the probability of hole and electron recombination in the light-emitting layer.

[0220] The above-described embodiments merely illustrate several implementations of the present invention, and their descriptions are relatively specific and detailed. However, they should not be construed as limiting the scope of the patent. It should be noted that a person skilled in the art may make various modifications and improvements without departing from the scope of the present invention, and these modifications and improvements fall within the scope of protection of the present invention. Therefore, the scope of protection of the patent for this invention shall be based on the appended claims.

Claims

1. An organic compound having a structure as shown in general formula (I): in: A and B are each independently selected from hydrogen or a group of formula (I-1) or formula (I-2), and only one of A and B is a group of formula (I-1) or formula (I-2); "*" indicates the connection position; X is O, S, NR1, CR2R3; Y may be identical or different in each case and may represent CR4 or N, wherein not more than two Ys per ring are N; L1 is selected from a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms or a substituted or unsubstituted heteroarylene group having 2 to 30 ring carbon atoms; L2-L3 are each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 30 ring carbon atoms; Ar1-Ar2 are each independently selected from a substituted or unsubstituted aromatic or heteroaromatic group having 5 to 40 ring atoms, or an aryloxy or heteroaryloxy group having 5 to 40 ring atoms, or a combination of these groups, wherein one or more of the groups can form a monocyclic or polycyclic aliphatic or aromatic ring system with each other and / or the ring to which they are bonded; R1-R4 are substituents which, at each occurrence, may be identical or different and are H, D, or a linear alkyl, alkoxy or thioalkoxy group having 1 to 20 C atoms, or a branched or cyclic alkyl, alkoxy or thioalkoxy group having 3 to 20 C atoms, or a silyl group, or a substituted 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, or a cyano group, a carbamoyl group, a halide a formyl group, a formyl group, an isocyano group, an isocyanate group, a thiocyanate group or an isothiocyanate group, a hydroxyl group, a nitro group, CF3, Cl, Br, F or a crosslinkable group, or a substituted or unsubstituted aromatic or heteroaromatic ring system having 5 to 40 ring atoms, or an aryloxy or heteroaryloxy group having 5 to 40 ring atoms, or a combination of these groups, any two adjacent substituents in R1-R4 can form a monocyclic or polycyclic aliphatic or aromatic ring system with each other and / or with the ring to which they are bonded.

2. The organic compound according to claim 1, having a structure as shown in general formula (II): in: L2-L3 are each independently selected from a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms or a substituted or unsubstituted heteroarylene group having 2 to 30 ring carbon atoms; the definitions of X, Y, L1, Ar1, and Ar2 are the same as those in claim 1.

3. The organic compound according to claim 1 or 2, wherein: Two adjacent Ys may be simultaneously bonded to a group represented by formula (I-3) or formula (I-4) and the remaining Ys are identical or different in each case and are represented by CR4 or N, Wherein, the dotted bond represents the bonding position, Z represents N or CR5, Q is selected from O, S, NR1, CR2R3, R4 has the same meaning as claim 1, and R5 has the same meaning as R4.

4. The organic compound according to any one of claims 1 to 3, wherein: L1 is selected from the following groups and combinations thereof: in, Each occurrence of X1 is independently selected from CR6 or N; Each occurrence of Y1 is independently selected from NR7, CR8R9, O, S, SiR 10 R 11 , S=O, SO2; R6-R 11 Each 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 or cyclic alkyl group having 3 to 20 C atoms, or a branched or cyclic alkoxy group having 3 to 20 C atoms, or a branched or cyclic thioalkoxy group, 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, or a cyano group, a carbamoyl group, a haloformyl group, a formyl group, an isocyano group, an isocyanate group, a thiocyanate group, an isothiocyanate group, a hydroxyl group, a nitro group, CF3, Cl, Br, F, a crosslinkable group, a substituted or unsubstituted aromatic group having 5 to 60 ring atoms, or a substituted or unsubstituted heteroaromatic group having 5 to 60 ring atoms, or an aryloxy group having 5 to 60 ring atoms, or a heteroaryloxy group having 5 to 60 ring atoms, or a combination of these groups, R6-R 11 Any two adjacent substituents in the group may form a monocyclic or polycyclic aliphatic or aromatic ring system with each other and / or with the ring to which they are bonded.

5. The organic compound according to any one of claims 1 to 4, wherein: L2-L3 are each independently selected from the following groups and combinations thereof: in, Each time X2 appears, it is independently selected from CR 1 or N; Each occurrence of Y2 is independently selected from NR 2 、O、S、SiR 3 R 4 、S=O、SO2、CR 5 R 6 ; R 1 -R 6 Each 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 or cyclic alkyl group having 3 to 20 C atoms, or a branched or cyclic alkoxy group having 3 to 20 C atoms, or a branched or cyclic thioalkoxy group, 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, or a cyano group, a carbamoyl group, a haloformyl group, a formyl group, an isocyano group, an isocyanate group, a thiocyanate group, an isothiocyanate group, a hydroxyl group, a nitro group, CF3, Cl, Br, F, a crosslinkable group, or a substituted or unsubstituted aromatic group having 5 to 60 ring atoms, or a substituted or unsubstituted heteroaromatic group having 5 to 60 ring atoms, or an aryloxy group having 5 to 60 ring atoms, or a heteroaryloxy group having 5 to 60 ring atoms, or a combination of these groups, R 1 -R 6 Any two adjacent substituents in the group may form a monocyclic or polycyclic aliphatic or aromatic ring system with each other and / or with the ring to which they are bonded.

6. The organic compound according to any one of claims 1 to 5, wherein: Ar1 and Ar2, when present, may be independently selected from the following groups and combinations thereof: The above groups are optionally substituted by 0, 1, 2 or 3 groups selected from D, F, Cl, Br, cyano, C1-C4 alkyl, C1-C3 haloalkyl, phenyl, naphthyl, fluorenyl, spirofluorenyl and C3-C10 cycloalkyl; A1 is a substituent which, on each occurrence, may be identical or different and is H, D, or a straight-chain alkyl, alkoxy or thioalkoxy group having 1 to 20 C atoms, or a branched or cyclic alkyl, alkoxy or thioalkoxy group having 3 to 20 C atoms, or a silyl group, or a substituted 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, or a cyano group, a carbamoyl group, a haloformyl group, a formyl group, an isocyano group, an isocyanate group, a thiocyanate group or an isothiocyanate group, a hydroxyl group, a nitro group, CF3, Cl, Br, F or a crosslinkable group, or a substituted or unsubstituted aromatic or heteroaromatic ring system having 5 to 40 ring atoms, or an aryloxy or heteroaryloxy group having 5 to 40 ring atoms, or a combination of these groups.

7. A mixture comprising an organic compound as described in any one of claims 1 to 6, and at least another organic functional material, wherein the organic functional material is selected from one or more of a hole injection material, a hole transport material, an electron transport material, an electron injection material, an electron blocking material, a hole blocking material, a luminescent material, a host material, and an organic dye.

8. An organic electronic device comprising a functional layer, characterized in that: The functional layer comprises an organic compound according to any one of claims 1 to 6, or a mixture according to claim 7.

9. The organic electronic device according to claim 8 is an organic electroluminescent device, comprising: a first electrode; a hole transport region, disposed on the first electrode; a light-emitting layer, disposed on the hole transport region; an electron transport region, disposed on the light-emitting layer; and a second electrode, disposed on the electron transport region; wherein the hole transport region comprises at least one organic compound according to any one of claims 1 to 6, or the mixture according to claim 7.

10. The organic electronic device according to claim 9, wherein the hole transport region has a multilayer structure, and the layer in contact with the light-emitting layer in the multilayer structure comprises an organic compound according to any one of claims 1 to 6, or the mixture according to claim 7.

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