Organic compound, organic light-emitting device and display device

Abstract

An organic compound, an organic light-emitting device and a display device. The organic compound has a general structural formula as represented by formula 1-1 below.

Description

Organic compound, organic light-emitting device and display device

[0001] This application claims priority to the Chinese patent application filed with the China Patent Office on March 29, 2024, with application number 202410383345.3, the entire contents of which are incorporated by reference into this application. Technical Field

[0002] The present application relates to the field of display technology, and in particular to an organic compound, an organic light-emitting device and a display apparatus. Background Art

[0003] The excellent optoelectronic properties of organic light-emitting diodes (OLEDs) have led to their rapid development in optoelectronic devices for displays, lighting, and other applications. Numerous improvements have been made to the device structure of OLEDs, such as the anode and cathode electrodes on a substrate, along with a hole transport layer (HTL), an electron transport layer (ETL), and an emitting layer (EML). Within this device structure, the performance of the emitting layer is crucial for developing long-life, high-efficiency OLEDs.

[0004] Organic light-emitting materials have undergone three generations of evolution: traditional fluorescent materials, phosphorescent materials, and thermally activated delayed fluorescence materials. Although phosphorescent materials and thermally activated delayed fluorescence (TADF) materials can achieve 100% exciton utilization and high device efficiency, phosphorescent materials generally require precious metal elements, which is costly. TADF, while not requiring precious metal elements, suffers from a wide spectral half-width, which is inconsistent with the current development trend of high color purity and high resolution.

[0005] In related technologies, the main method for improving the color purity of electroluminescence is to use filters or construct special optical microcavity structures. However, this approach causes energy loss and reduces device efficiency. Therefore, from the perspective of organic light-emitting materials, the design and synthesis of organic light-emitting molecules with narrow half-width is the fundamental solution to the problem of device light impurity. Technical Solutions

[0006] The embodiments of the present application provide an organic compound, an organic light-emitting device, and a display device, which can obtain a light-emitting material with a narrow half-width.

[0007] The present invention provides an organic compound, the general structural formula of which is shown in Formula 1-1 below:

[0008] Wherein, M is selected from a substituted or unsubstituted aromatic group having 5 to 40 carbon atoms;

[0009] Ar1 and Ar2 are each independently selected from a substituted or unsubstituted heteroaryl group having 4 to 20 carbon atoms;

[0010] R1, R2, R3, R4, R5 and R6 are each independently selected from one of an electron-donating group and an electron-withdrawing group, and any two adjacent ones of R1, R2, R3, R4, R5 and R6 may form a ring or not.

[0011] According to the above-mentioned object of the present application, an embodiment of the present application further provides an organic light-emitting device, comprising a first electrode, a second electrode, and a light-emitting layer disposed between the first electrode and the second electrode, wherein the light-emitting layer comprises at least one of organic compounds;

[0012] The general structural formula of the organic compound is shown in Formula 1-1 below:

[0013] Wherein, M is selected from a substituted or unsubstituted aromatic group having 5 to 40 carbon atoms;

[0014] Ar1 and Ar2 are each independently selected from a substituted or unsubstituted heteroaryl group having 4 to 20 carbon atoms;

[0015] R1, R2, R3, R4, R5 and R6 are each independently selected from one of an electron-donating group and an electron-withdrawing group, and any two adjacent ones of R1, R2, R3, R4, R5 and R6 may form a ring or not.

[0016] According to the above-mentioned object of the present application, an embodiment of the present application further provides a display device, the display device including an organic light-emitting device, the organic light-emitting device including a first electrode, a second electrode, and a light-emitting layer disposed between the first electrode and the second electrode, wherein the light-emitting layer includes at least one of organic compounds;

[0017] The general structural formula of the organic compound is shown in Formula 1-1 below:

[0018] Wherein, M is selected from a substituted or unsubstituted aromatic group having 5 to 40 carbon atoms;

[0019] Ar1 and Ar2 are each independently selected from a substituted or unsubstituted heteroaryl group having 4 to 20 carbon atoms;

[0020] R1, R2, R3, R4, R5 and R6 are each independently selected from one of an electron-donating group and an electron-withdrawing group, and any two adjacent ones of R1, R2, R3, R4, R5 and R6 may form a ring or not. BRIEF DESCRIPTION OF THE DRAWINGS

[0021] The following detailed description of the specific embodiments of the present application in conjunction with the accompanying drawings will make the technical solutions and other beneficial effects of the present application apparent.

[0022] FIG1 is a graph showing the luminescence spectrum of an organic compound provided in an embodiment of the present application;

[0023] FIG2 is a schematic structural diagram of an organic light-emitting device provided in an embodiment of the present application. Modes for Carrying Out the Invention

[0024] The following will clearly and completely describe the technical solutions in the embodiments of this application in conjunction with the accompanying drawings. Obviously, the described embodiments are only some of the embodiments of this application, not all of the embodiments. Based on the embodiments of this application, all other embodiments obtained by those skilled in the art without inventive work are within the scope of protection of this application. In addition, it should be understood that the specific embodiments described herein are only for the purpose of illustrating and explaining this application and are not intended to limit this application. In this application, unless otherwise stated, directional words such as "upper" and "lower" generally refer to the upper and lower parts of the device in actual use or operation, specifically the directions in the drawings in the accompanying drawings; while "inner" and "outer" refer to the outline of the device. In this application, "optionally", "optional", and "optional" mean optional, that is, they can be selected from either of the two parallel options of "with" or "without". If multiple "optional" items appear in a technical solution, unless otherwise specified and there are no contradictions or mutual constraints, each "optional" item is independent. In this application, the technical features described in an open manner include closed technical solutions composed of the listed features, and also include open technical solutions containing the listed features.

[0025] In this application, aromatic group, aromatic series, and aromatic ring system have the same meaning and are interchangeable. "Aryl or aromatic group or aromatic ring system" refers to an aromatic hydrocarbon group derived from an aromatic ring compound by removing a hydrogen atom, which can be a monocyclic aromatic group, a condensed aromatic group, or a polycyclic aromatic group. For polycyclic rings, at least one is an aromatic ring system. For example, "substituted or unsubstituted aryl having 6 to 40 ring atoms" refers to an aryl group containing 6 to 40 ring atoms, preferably a substituted or unsubstituted aryl group having 6 to 30 ring atoms, more preferably a substituted or unsubstituted aryl group having 6 to 18 ring atoms, and particularly preferably a substituted or unsubstituted aryl group having 6 to 14 ring atoms, and the aryl group is optionally further substituted; suitable examples include, but are not limited to: phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthrenyl, fluoranthenyl, triphenylene, pyrenyl, perylenyl, naphthphenyl, fluorenyl, perylene, acenaphthenyl, and derivatives thereof. It is understood that multiple aromatic groups may also be interrupted by short non-aromatic units (e.g. <10% non-H atoms, such as C, N or O atoms), specifically acenaphthene, fluorene, or 9,9-diarylfluorene, triarylamine, diaryl ether systems should also be included in the definition of aromatic groups.

[0026] In the present application, heteroaromatic group, heteroaromatic series, and heteroaromatic ring system have the same meaning and can be interchanged. "Heteroaromatic group or heteroaromatic group or heteroaromatic ring system" means that at least one carbon atom on the basis of aromatic group is replaced by non-carbon atom, and non-carbon atom can be N atom, O atom, S atom, etc. For example, "substituted or unsubstituted heteroaryl having 5 to 40 ring atoms" refers to heteroaryl having 5 to 40 ring atoms, preferably substituted or unsubstituted heteroaryl having 6 to 30 ring atoms, more preferably substituted or unsubstituted heteroaryl having 6 to 18 ring atoms, particularly preferably substituted or unsubstituted heteroaryl having 6 to 14 ring atoms, and heteroaryl is optionally further substituted, and suitable examples include but are not limited to: thienyl, furyl, pyrrolyl, oxadiazolyl, triazolyl, imidazolyl, pyridyl, bipyridyl, pyrimidinyl, Triazine, acridinyl, pyridazinyl, pyrazinyl, quinolyl, isoquinolyl, quinazolinyl, quinoxalinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, benzothiophenyl, benzofuranyl, indolyl, pyrroloimidazolyl, pyrrolopyrrolyl, thienopyrrolyl, thienothiphenyl, furopyrrolyl, furofuranyl, thienofuranyl, benzisoxazolyl, benzisothiazolyl, benzimidazolyl, o-naphthyl, phenanthridinyl, primary pyridyl, quinazolinone, dibenzothiophenyl, dibenzofuranyl, carbazolyl and derivatives thereof.

[0027] In the present application, "substituted" means that one or more hydrogen atoms in the substituted group are replaced by a substituent. When the same substituent appears multiple times, it can be independently selected from different groups. For example, if the general formula contains multiple R, then R can be independently selected from different groups. In the embodiments of the present application, "substituted or unsubstituted" means that the defined group can be substituted or not substituted; when the defined group is substituted, it should be understood that the defined group can be substituted by one or more substituents R, and the substituents R are selected from but not limited to: deuterium atoms, cyano groups, isocyano groups, nitro groups or halogens, alkyl groups containing 1-20 C atoms, heterocyclic groups containing 3-20 ring atoms, aromatic groups containing 6-20 ring atoms, heteroaromatic groups containing 5-20 ring atoms, -NR'R", silane groups, carbonyl groups, alkoxycarbonyl groups, aryloxycarbonyl groups, carbamoyl groups, haloformyl groups, formyl groups, isocyanate groups, thiocyanate groups, isothiocyanate groups, hydroxyl groups, trifluoromethyl groups, and the above groups can also be further substituted by substituents acceptable in the art; wherein, R in -NR'R" ' and R" are independently selected from, but not limited to, H, a deuterium atom, a cyano group, an isocyano group, a nitro group or a halogen, an alkyl group containing 1 to 10 C atoms, a heterocyclic group containing 3 to 20 ring atoms, an aromatic group containing 6 to 20 ring atoms, and a heteroaromatic group containing 5 to 20 ring atoms. Preferably, R is selected from, but not limited to, a deuterium atom, a cyano group, an isocyano group, a nitro group or a halogen, an alkyl group containing 1 to 10 C atoms, a heterocyclic group containing 3 to 10 ring atoms, an aromatic group containing 6 to 20 ring atoms, a heteroaromatic group containing 5 to 20 ring atoms, a silane group, a carbonyl group, an alkoxycarbonyl group, an aryloxycarbonyl group, a carbamoyl group, a haloformyl group, a formyl group, an isocyanate group, a thiocyanate group, an isothiocyanate group, a hydroxyl group, and a trifluoromethyl group, and the above groups may also be further substituted by substituents acceptable in the art.

[0028] In the present application, "amino group" refers to an amine derivative having a structural feature of the formula -NR'R", where R' and R" have the same meanings as described above.

[0029] In the present application, the "number of ring atoms" refers to the number of atoms among the atoms constituting the ring itself of a structural compound (for example, a monocyclic compound, a condensed ring compound, a cross-linked compound, a carbocyclic compound, a heterocyclic compound) obtained by atoms being bonded together to form a ring; when the ring is substituted by a substituent, the atoms contained in the substituent are not included in the ring atoms. The same applies to the "number of ring atoms" described below unless otherwise specified. For example, the number of ring atoms of a benzene ring is 6, the number of ring atoms of a naphthalene ring is 10, and the number of ring atoms of a thienyl group is 5.

[0030] In this application, "*" connected to a single bond indicates a connection or fusion site.

[0031] In the present application, when a linking site is not specified in a group, it means that any linking site in the group can be used as the linking site.

[0032] In the present application, when no fusion site is specified in a group, it means that any fusion site in the group can be used as the fusion site, and preferably two or more sites in the adjacent position in the group are fusion sites.

[0033] In this application, when a group contains multiple substituents with the same symbol, the substituents may be the same or different from each other, for example The six Rs on the benzene ring may be the same as or different from each other.

[0034] In the present application, the single bond connecting the substituent runs through the corresponding ring, indicating that the substituent can be connected to any position of the ring, for example In which R is connected to any substitutable position of the benzene ring; express Can be used with The benzene ring can be fused at any position.

[0035] The cyclic alkyl group or cycloalkyl group described in the present application have the same meaning and can be interchanged.

[0036] In the present application, "adjacent groups" refers to two substituents with no substitutable sites between them.

[0037] In the present application, "two adjacent R1 or R3 or R5 form a ring with each other" means a ring system formed by two adjacent R1 or R3 or R5 connected to each other, and the ring system can be selected from aliphatic hydrocarbon ring, aliphatic heterocycle, aromatic hydrocarbon ring or aromatic heterocycle. Preferably,

[0038] The present invention provides an organic compound, the general structural formula of which is shown in Formula 1-1 below:

[0039] Wherein, M is selected from a substituted or unsubstituted aromatic group having 5 to 40 carbon atoms;

[0040] Ar1 and Ar2 are each independently selected from a substituted or unsubstituted heteroaryl group having 4 to 20 carbon atoms;

[0041] R1, R2, R3, R4, R5 and R6 are each independently selected from one of an electron-donating group and an electron-withdrawing group, and any two adjacent ones of R1, R2, R3, R4, R5 and R6 may form a ring or not.

[0042] During the implementation and application process, in the organic compounds provided in the embodiments of the present application, by introducing heteroaryl groups into carbon-nitrogen compounds and increasing the n-conjugated plane of the organic compounds, the energy gap is reduced to cause the spectrum to red-shift, and the fluorescence quantum yield of the organic compounds is improved, so as to obtain high-efficiency, narrow-spectrum green light materials. The rigid molecular structure of the organic compounds is conducive to improving thermal stability. When the organic compounds are applied to organic light-emitting devices, the luminous efficiency, color purity and life of the organic light-emitting devices can be improved.

[0043] Furthermore, in one embodiment, M is selected from a substituted or unsubstituted aromatic group having 10 to 35 carbon atoms. For example, the number of carbon atoms in the aromatic group can be 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34 or 35, and the above number of carbon atoms is for example only and is not limited thereto.

[0044] In one embodiment, Ar1 and Ar2 are each independently selected from a substituted or unsubstituted heteroaryl group having 4 to 10 carbon atoms. For example, the number of carbon atoms in the heteroaryl group can be 4, 5, 6, 7, 8, 9 or 10, and the above carbon number is for example only and is not limited thereto.

[0045] It can be understood that any two adjacent ones of R1, R2, R3, R4, R5 and R6 refer to the two adjacent Cs of R1, R2, R3, R4, R5 and R6.

[0046] Furthermore, in one embodiment, Ar1 and Ar2 are respectively selected from heteroaryl groups having 4 to 20 carbon atoms and being substituted or unsubstituted, and the heteroatoms are selected from at least one of N, O, S, Se and Te; specifically, when Ar1 and Ar2 are selected from heteroaryl groups having 4 to 20 carbon atoms and being substituted or unsubstituted, or when Ar1 and Ar2 are selected from heteroaryl groups having 4 to 10 carbon atoms and being substituted or unsubstituted, the heteroatoms in the heteroaryl groups are selected from at least one of N, O, S, Se and Te.

[0047] In one embodiment, R1, R2, R3, R4, R5 and R6 are each independently selected from at least one of H, D, a straight-chain hydrocarbon group having 1 to 60 carbon atoms, a branched hydrocarbon group having 1 to 60 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted aryl group having 5 to 40 carbon atoms, a substituted or unsubstituted heteroaryl group having 4 to 25 carbon atoms, a substituted or unsubstituted ether group having 5 to 20 carbon atoms, a carbonyl group, a carboxyl group, a nitro group and a cyano group.

[0048] In one embodiment, the general structural formula of the organic compound is shown in Formula 1-2 below:

[0049] Among them, R7, R8, R9 and R 10 Each is independently selected from a single bond, H, D, a straight-chain hydrocarbon group having 1 to 60 carbon atoms, a branched hydrocarbon group having 1 to 60 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted aryl group having 5 to 40 carbon atoms, a substituted or unsubstituted heteroaryl group having 4 to 25 carbon atoms, a substituted or unsubstituted ether group having 5 to 20 carbon atoms, a carbonyl group, a carboxyl group, a nitro group, and a cyano group, and the heteroatom in the substituted or unsubstituted heteroaryl group having 4 to 25 carbon atoms is selected from at least one of Si, N, O, S, and Se; and R7, R8, R9, and R 10 Any two adjacent ones in the ring may form a ring or not; it is understood that R7, R8, R9 and R 10 Any two adjacent ones refer to R7, R8, R9 and R 10 The two connected to adjacent C.

[0050] In one embodiment, when R7, R8, R9 and R 10 When R7, R8, R9 and R are each independently selected from a linear hydrocarbon group having 1 to 60 carbon atoms, a branched hydrocarbon group having 1 to 60 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted aryl group having 5 to 40 carbon atoms, a substituted or unsubstituted heteroaryl group having 4 to 25 carbon atoms, and a substituted or unsubstituted ether group having 5 to 20 carbon atoms, 10 The two adjacent ones are connected to form a ring.

[0051] X is selected from one of -NL1-, -O-, -S-, -Se- and -Te-; L1 is selected from one of H, D, a straight-chain hydrocarbon group having 1 to 60 carbon atoms, a branched hydrocarbon group having 1 to 60 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted aryl group having 5 to 40 carbon atoms, and a substituted or unsubstituted heteroaryl group having 4 to 20 carbon atoms; and the heteroatom in the substituted or unsubstituted heteroaryl group having 4 to 20 carbon atoms is selected from at least one of Si, N, O, S, Se and Te.

[0052] When X is selected from -NL1-, L1 and R7, R8, R9 and R 10 One of them is cyclic or not.

[0053] Furthermore, in one embodiment, when X is selected from -NL1-, L1 is selected from a substituted or unsubstituted heteroaryl group having 4 to 20 carbon atoms, L1 and R7, R8, R9 and R 10 One of them forms a ring.

[0054] In one embodiment, L1 is selected from a substituted or unsubstituted heteroaryl group having 4 to 10 carbon atoms. For example, the carbon atoms in the heteroaryl group can be 4, 5, 6, 7, 8, 9 or 10, and the above carbon number is for example only and is not limited thereto.

[0055] In one embodiment of the present application, in order to improve the molecular structural rigidity of the organic compound, that is, to improve the thermal stability of the organic compound, L1 and R7 may be connected to form a ring. Therefore, the general structural formula of the organic compound may be as shown in Formulas 1-3 below:

[0056] Ar3 is selected from a substituted or unsubstituted heteroaryl group having 4 to 20 carbon atoms, and in the substituted or unsubstituted heteroaryl group having 4 to 20 carbon atoms, the heteroatom is selected from at least one of N, O, S, Se and Te.

[0057] In one embodiment, Ar3 is selected from a substituted or unsubstituted heteroaryl group having 4 to 10 carbon atoms. For example, the heteroaryl group may have 4, 5, 6, 7, 8, 9 or 10 carbon atoms, and the above carbon number is for example only and is not limited thereto.

[0058] In one embodiment, at least two of Ar1, Ar2, and Ar3 are the same group; further preferably, Ar1, Ar2, and Ar3 are all the same group, thereby simplifying the preparation process and reducing the synthesis cost; when Ar1, Ar2, and Ar3 are all the same group, the general structural formula of the organic compound is as follows:

[0059] Ar is selected from a substituted or unsubstituted heteroaryl group having 4 to 20 carbon atoms, and the heteroatom in the substituted or unsubstituted heteroaryl group having 4 to 20 carbon atoms is selected from N, O, S, Se or Te.

[0060] In one embodiment, Ar is selected from a substituted or unsubstituted heteroaryl group having 4 to 10 carbon atoms. For example, the heteroaryl group may have 4, 5, 6, 7, 8, 9 or 10 carbon atoms, and the above carbon number is for example only and is not limited thereto.

[0061] In one embodiment, Ar1, Ar2 and Ar3 are each independently selected from at least one of a substituted or unsubstituted furyl group, a substituted or unsubstituted thienyl group, a substituted or unsubstituted pyrrolyl group, a substituted or unsubstituted benzofuranyl group, a substituted or unsubstituted benzothienyl group, and a substituted or unsubstituted indolyl group.

[0062] Specifically, Ar1, Ar2 and Ar3 are each independently selected from furyl, thienyl, pyrrolyl, benzofuranyl, benzothienyl, indolyl, as well as One of them.

[0063] Specifically, the organic compound can be selected from one of the following compounds:

[0064] Furthermore, the luminescence spectrum peak value of the organic compound provided in the embodiment of the present application is 500-580nm, and the luminescence spectrum half-peak width is less than 50nm; specifically, the organic compound can be dissolved in toluene to prepare 10 -5 M solution and tested its photoluminescence spectrum.

[0065] In addition, the embodiments of the present application provide specific examples of the organic compounds described in the above embodiments, including specific structures and corresponding preparation processes.

[0066] Example 1

[0067] Organic compound M1:

[0068] The synthesis process of organic compound M1 is as follows:

[0069] Synthesis of 1a: Indole (585 mg, 5 mmol), Cu(OAc)2 (45 mg, 0.25 mmol), and toluene (20 mL) were added to a 100 mL single-necked round-bottom flask. [Bis(trifluoroacetoxy)iodo]benzene (2.15 g, 5 mmol) dissolved in toluene (30 mL) was then added dropwise at 0°C. After the addition was complete, the reaction mixture was allowed to react at 0°C for 2 h. After completion of the reaction, the mixture was neutralized with saturated sodium bicarbonate solution, extracted with dichloromethane, and the solvent removed in vacuo. The product was purified by column chromatography to afford intermediate 1a as a white solid (yield 69%).

[0070] Elemental analysis: theoretical value C: 83.46; H: 4.38; N: 12.17; measured value C: 83.43; H: 4.38; N: 12.15.

[0071] Synthesis of 1b: Under nitrogen, a 100 mL two-necked round-bottom flask was charged with intermediate 1a (1.725 g, 5 mmol), 2-iodothiophene (3.318 g, 15.8 mmol), palladium acetate (180 mg, 0.788 mmol), tri-tert-butylphosphine tetrafluoroborate (686 mg, 2.34 mmol), sodium tert-butoxide (2.880 g, 30 mmol), and 50 mL of toluene. The mixture was heated to 110°C and reacted overnight. The reaction mixture was then cooled to room temperature, extracted with dichloromethane, and the solvent removed in vacuo. The product was purified by column chromatography to afford intermediate 1b as a white solid (yield 50%).

[0072] Elemental analysis: theoretical value C: 73.07; H: 3.58; N: 7.10; S: 16.25; tested value C: 73.06; H: 3.57; N: 7.11; S: 16.24.

[0073] Synthesis of Organic Compound M1: Under nitrogen, intermediate 1b (2.561 g, 5 mmol), palladium acetate (339 mg, 1.5 mmol), silver oxide (122 mg, 1.5 mmol), and 25 mL of pivalic acid were added to a 100 mL two-necked round-bottom flask. The mixture was reacted at 160°C for 24 h. After cooling to room temperature, the mixture was neutralized with saturated sodium bicarbonate solution, extracted with dichloromethane, and the solvent removed in vacuo. The product was purified by column chromatography to obtain product M1 as a yellow solid (yield 20%).

[0074] Elemental analysis: C: 73.82; H: 2.58; N: 7.17; S: 16.42; Test value C: 73.80; H: 2.59; N: 7.15; S: 16.42.

[0075] Example 2

[0076] Organic compound M2:

[0077] Synthesis process of organic compound M2:

[0078] Synthesis of 2a: 5-Chloro-1H-indole (758 mg, 5 mmol), Cu(OAc)2 (45 mg, 0.25 mmol), and toluene (20 mL) were added to a 100 mL single-necked round-bottom flask. [Bis(trifluoroacetoxy)iodo]benzene (2.15 g, 5 mmol) dissolved in toluene (30 mL) was then added dropwise at 0°C. After the addition was complete, the reaction mixture was allowed to react at 0°C for 2 h. After completion of the reaction, the mixture was neutralized with saturated sodium bicarbonate solution, extracted with dichloromethane, and the solvent removed in vacuo. The product was purified by column chromatography to afford intermediate 2a as a white solid (yield 75%).

[0079] Elemental analysis: theoretical value C: 64.24; H: 2.70; Cl: 23.70; N: 9.36; tested value C: 64.23; H: 2.70; Cl: 23.71; N: 9.35.

[0080] Synthesis of 2b: Under nitrogen, a 100 mL two-necked round-bottom flask was charged with intermediate 2a (2.244 g, 5 mmol), 2-bromothiophene (2.568 g, 15.8 mmol), palladium acetate (180 mg, 0.788 mmol), tri-tert-butylphosphine tetrafluoroborate (686 mg, 2.34 mmol), sodium tert-butoxide (2.880 g, 30 mmol), and 50 mL of toluene. The mixture was heated to 110° C. and reacted overnight. The reaction mixture was then cooled to room temperature, extracted with dichloromethane, and the solvent removed in vacuo. The product was purified by column chromatography to afford intermediate 2b as a white solid (yield 50%).

[0081] Elemental analysis: theoretical value C: 62.21; H: 2.61; Cl: 15.30; N: 6.15; S: 13.84; tested value C: 62.21; H: 2.62; Cl: 15.31; N: 6.15; S: 13.85.

[0082] Synthesis of 2c: Under nitrogen, intermediate 2b (3.476 g, 5 mmol), palladium acetate (339 mg, 1.5 mmol), silver oxide (122 mg, 1.5 mmol), and 25 mL of pivalic acid were added to a 100 mL two-necked round-bottom flask. The mixture was reacted at 160°C for 24 h. After cooling to room temperature, the mixture was neutralized with saturated sodium bicarbonate solution, extracted with dichloromethane, and the solvent was removed in vacuo. The product was purified by column chromatography to obtain intermediate 2c as a yellow solid (yield 25%).

[0083] Elemental analysis: theoretical value C: 62.75; H: 1.76; Cl: 15.43; N: 6.10; S: 13.96; tested value C: 62.77; H: 1.75; Cl: 15.43; N: 6.11; S: 13.97.

[0084] Synthesis of organic compound M2: Under nitrogen, a 100 mL two-necked round-bottom flask was charged with intermediate 2c (2.561 g, 5 mmol), tetrakistriphenylphosphine palladium (339 mg, 1.5 mmol), phenylboronic acid (2.847 g, 18 mmol), potassium carbonate (2.44 g, 30 mmol), 25 mL of toluene, 5 mL of ethanol, and 2 mL of water. The reaction was incubated at 90°C for 24 h. After cooling to room temperature, the mixture was neutralized with saturated sodium bicarbonate solution, extracted with dichloromethane, and the solvent removed in vacuo. The product was purified by column chromatography to obtain product M2 as a yellow solid (yield 30%).

[0085] Elemental analysis: theoretical value C: 79.68; H: 3.34; N: 5.16; S: ​​11.82; tested value C: 79.68; H: 3.34; N: 5.16; S: ​​11.82.

[0086] Example 3

[0087] Organic compound M3:

[0088] Synthesis process of organic compound M3:

[0089] Synthesis of 3a: 5-Bromo-1H-indole (980 mg, 5 mmol), Cu(OAc)2 (45 mg, 0.25 mmol), and toluene (20 mL) were added to a 100 mL single-necked round-bottom flask. [Bis(trifluoroacetoxy)iodo]benzene (2.15 g, 5 mmol) dissolved in toluene (30 mL) was then added dropwise at 0°C. After the addition was complete, the reaction mixture was allowed to react at 0°C for 2 h. After completion of the reaction, the mixture was neutralized with saturated sodium bicarbonate solution, extracted with dichloromethane, and the solvent removed in vacuo. The product was purified by column chromatography to afford intermediate 3a as a white solid (yield 70%).

[0090] Elemental analysis: theoretical value C: 49.52; H: 2.08; Br: 41.18; N: 7.22; found value C: 49.53; H: 2.06; Br: 41.19; N: 7.24.

[0091] Synthesis of 3b: Under nitrogen, a 100 mL two-necked round-bottom flask was charged with 3a (2.911 g, 5 mmol), 2-bromothiophene (2.568 g, 15.8 mmol), palladium acetate (180 mg, 0.788 mmol), tri-tert-butylphosphine tetrafluoroborate (686 mg, 2.34 mmol), sodium tert-butoxide (2.880 g, 30 mmol), and 50 mL of toluene. The mixture was heated to 110°C and reacted overnight. The reaction mixture was then cooled to room temperature, extracted with dichloromethane, and the solvent removed in vacuo. The product was purified by column chromatography to afford intermediate 3b as a yellow solid (yield 30%).

[0092] Elemental analysis: theoretical value C: 52.19; H: 2.18; Br: 28.93; N: 5.07; S: 11.61; tested value C: 52.17; H: 2.19; Br: 28.91; N: 5.08; S: 11.63.

[0093] Synthesis of 3c: Under nitrogen, intermediate 3b (4.143 g, 5 mmol), palladium acetate (339 mg, 1.5 mmol), silver oxide (122 mg, 1.5 mmol), and 25 mL of pivalic acid were added to a 100 mL two-necked round-bottom flask. The reaction was incubated at 160°C for 24 h. After cooling to room temperature, the mixture was neutralized with saturated sodium bicarbonate solution, extracted with dichloromethane, and the solvent removed in vacuo. The product was purified by column chromatography to afford intermediate 3c as a yellow solid (yield 27%).

[0094] Elemental analysis: theoretical value C: 52.28; H: 1.47; Br: 29.15; N: 5.11; S: 11.69; tested value C: 52.27; H: 1.47; Br: 29.13; N: 5.12; S: 11.70.

[0095] Synthesis of organic compound M3: Under nitrogen, a 100 mL two-necked round-bottom flask was charged with intermediate 3c (4.112 g, 5 mmol), diphenylamine (2.670 g, 15.8 mmol), palladium acetate (180 mg, 0.788 mmol), tri-tert-butylphosphine tetrafluoroborate (686 mg, 2.34 mmol), sodium tert-butoxide (2.880 g, 30 mmol), and 50 mL of toluene. The mixture was heated to 90°C and reacted overnight. The reaction mixture was then cooled to room temperature, extracted with dichloromethane, and the solvent removed in vacuo. The product was purified by column chromatography to obtain product M3 as a yellow solid (yield 20%).

[0096] Elemental analysis: Theoretical value: C: 79.53; H: 3.89; N: 7.73; S: 8.85; Measured value C: 79.53; H: 3.87; N: 7.74; S: 8.85.

[0097] Example 4

[0098] Organic Compound M4:

[0099] Synthesis process of organic compound M4:

[0100] Synthesis of 4a: 5-Fluoro-1H-indole (675 mg, 5 mmol), Cu(OAc)2 (45 mg, 0.25 mmol), and toluene (20 mL) were added to a 100 mL single-necked round-bottom flask. [Bis(trifluoroacetoxy)iodo]benzene (2.15 g, 5 mmol) dissolved in toluene (30 mL) was then added dropwise at 0°C. After the addition was complete, the reaction mixture was allowed to react at 0°C for 2 h. After completion of the reaction, the mixture was neutralized with saturated sodium bicarbonate solution, extracted with dichloromethane, and the solvent removed in vacuo. The product was purified by column chromatography to afford intermediate 4a as a white solid (yield 60%).

[0101] Elemental analysis: Theoretical value: C: 72.18; H: 3.03; F: 14.27; N: 10.52; Measured value C: 72.16; H: 3.04; F: 14.26; N: 10.53.

[0102] Synthesis of 4b: Under nitrogen, a 100 mL two-necked round-bottom flask was charged with intermediate 4a (1.997 g, 5 mmol), 2-bromothiophene (2.568 g, 15.8 mmol), palladium acetate (180 mg, 0.788 mmol), tri-tert-butylphosphine tetrafluoroborate (686 mg, 2.34 mmol), sodium tert-butoxide (2.880 g, 30 mmol), and 50 mL of toluene. The mixture was heated to 110°C and reacted overnight. The reaction mixture was then cooled to room temperature, extracted with dichloromethane, and the solvent removed in vacuo. The product was purified by column chromatography to afford intermediate 4b as a white solid (yield 40%).

[0103] Elemental analysis: Theoretical value: C: 66.96; H: 2.81; F: 8.83; N: 6.51; S: 14.89; Test value C: 66.96; H: 2.82; F: 8.83; N: 6.50; S: 14.90.

[0104] Synthesis of 4c: Under nitrogen, intermediate 4b (3.274 g, 5 mmol), palladium acetate (339 mg, 1.5 mmol), silver oxide (122 mg, 1.5 mmol), and 25 mL of pivalic acid were added to a 100 mL two-necked round-bottom flask. The mixture was reacted at 160°C for 24 h. After cooling to room temperature, the mixture was neutralized with saturated sodium bicarbonate solution, extracted with dichloromethane, and the solvent was removed in vacuo. The product was purified by column chromatography to obtain intermediate 4c as a yellow solid (yield 25%).

[0105] Elemental analysis: Theoretical value: C: 67.57; H: 1.89; F: 8.91; N: 6.57; S: 15.04; Measured value: C: 67.58; H: 1.91; F: 8.91; N: 6.53; S: 15.04.

[0106] Synthesis of Organic Compound M4: Under nitrogen, a 100 mL two-necked round-bottom flask was charged with intermediate 4c (3.198 g, 5 mmol), carbazole (1.670 g, 10 mmol), cesium carbonate (6.516 g, 20 mmol), and 30 mL of N,N-dimethylformamide. The mixture was heated to 145°C overnight, then cooled to room temperature, extracted with dichloromethane, and the solvent removed in vacuo. The product was purified by column chromatography to afford product M4 as a white solid (30% yield).

[0107] Elemental analysis: Theoretical value: C: 79.98; H: 3.36; N: 7.77; S: 8.89; Measured value: C: 79.99; H: 3.35; N: 7.78; S: 8.89.

[0108] Example 5

[0109] Organic compound M5:

[0110] Synthesis process of organic compound M5:

[0111] Synthesis of 5a: Under nitrogen, a 100 mL two-necked round-bottom flask was charged with indolo[2,3-a]carbazole (1.268 g, 5 mmol), 2-bromothiophene (1.712 g, 10.5 mmol), palladium acetate (119 mg, 0.525 mmol), tri-tert-butylphosphine tetrafluoroborate (457 mg, 1.56 mmol), sodium tert-butoxide (1.920 g, 20 mmol), and 50 mL of toluene. The mixture was heated to 110°C overnight, then cooled to room temperature, extracted with dichloromethane, and the solvent removed in vacuo. The product was purified by column chromatography to afford intermediate 5a as a white solid (yield 75%).

[0112] Elemental analysis: Theoretical value: C: 74.26; H: 3.83; N: 6.66; S: ​​15.25; Measured value: C: 74.24; H: 3.85; N: 6.63; S: 15.24.

[0113] Synthesis of 5b: Intermediate 5a (2.1 g, 5 mmol) was dissolved in 50 mL of dichloromethane. A solution prepared by dissolving N-bromosuccinimide (890 mg, 5 mol) in dimethylformamide was slowly added over 4 hours while stirring the solution at 0°C. The reaction was stirred at room temperature for 2 hours and then extracted with distilled water and dichloromethane. The solvent was removed in vacuo. The product was purified by column chromatography to afford intermediate 5b as a white solid (95% yield).

[0114] Elemental analysis: Theoretical value: C: 62.53; H: 3.03; Br: 16.00; N: 5.61; S: 12.84; Measured value: C: 62.53; H: 3.01; Br: 16.01; N: 5.62; S: 12.82.

[0115] Synthesis of 5c: Under nitrogen, a 100 mL two-necked round-bottom flask was charged with intermediate 5b (2.489 g, 5 mmol), phenol (479 mg, 5.25 mmol), cuprous iodide (480 mg, 0.5 mmol), Cs2CO3 (3.575 g, 11 mmol), and 50 mL of N,N-dimethylformamide. The mixture was heated to 160°C for 16 hours, after which the reaction mixture was cooled to room temperature, extracted with dichloromethane, and the solvent removed in vacuo. The product was purified by column chromatography to afford intermediate 5c as a white solid (yield 75%).

[0116] Elemental analysis: Theoretical value: C: 74.97; H: 3.93; N: 5.46; O: 3.12; S: 12.51; Measured value: C: 74.95; H: 3.94; N: 5.46; O: 3.13; S: 12.51.

[0117] Synthesis of Organic Compound M5: Under nitrogen, intermediate 5c (2.561 g, 5 mmol), palladium acetate (339 mg, 1.5 mmol), silver oxide (122 mg, 1.5 mmol), and 25 mL of pivalic acid were added to a 100 mL two-necked round-bottom flask. The mixture was reacted at 160°C for 24 h. After cooling to room temperature, the mixture was neutralized with saturated sodium bicarbonate solution, extracted with dichloromethane, and the solvent was removed in vacuo. The product was purified by column chromatography to obtain product M5 as a white solid (yield 20%).

[0118] Elemental analysis: Theoretical value: C: 75.87; H: 2.79; N: 5.53; O: 3.16; S: ​​12.66; Measured value: C: 75.88; H: 2.77; N: 5.53; O: 3.17; S: 12.65.

[0119] Example 6

[0120] Organic compound M6:

[0121] Synthesis process of organic compound M6:

[0122] Synthesis of 6a: Under nitrogen, a 50 mL two-necked round-bottom flask was charged with intermediate 5b (2.489 g, 5 mmol), thiophenol (550 mg, 5.25 mmol), cuprous iodide (144 mg, 0.15 mmol), sodium tert-butoxide (2.275 g, 7 mmol), and 25 mL of DMSO. The reaction mixture was heated to 100°C for 16 hours, after which the reaction mixture was cooled to room temperature, extracted with dichloromethane, and the solvent removed in vacuo. The product was purified by column chromatography to afford intermediate 6a as a white solid (yield 75%).

[0123] Elemental analysis: Theoretical value: C: 72.70; H: 3.81; N: 5.30; S: 18.19; Measured value: C: 72.70; H: 3.82; N: 5.31; S: 18.19.

[0124] Synthesis of organic compound M6: Under nitrogen, intermediate 6a (1.056 g, 5 mmol), palladium acetate (339 mg, 1.5 mmol), silver oxide (122 mg, 1.5 mmol), and 25 mL of pivalic acid were added to a 100 mL two-necked round-bottom flask. The mixture was reacted at 160°C for 24 h. After cooling to room temperature, the mixture was neutralized with saturated sodium bicarbonate solution, extracted with dichloromethane, and the solvent was removed in vacuo. The product was purified by column chromatography to obtain product M6 as a white solid (yield 25%).

[0125] Elemental analysis: Theoretical value: C: 73.54; H: 2.70; N: 5.36; S: ​​18.40; Measured value: C: 73.53; H: 2.71; N: 5.35; S: 18.42.

[0126] Example 7

[0127] Organic compound M7:

[0128] Synthesis process of organic compound M7:

[0129] Synthesis of 7a: Under nitrogen, a 50 mL two-necked round-bottom flask was charged with intermediate 5b (2.489 g, 5 mmol), phenylselenol (825 mg, 5.25 mmol), cuprous iodide (144 mg, 0.15 mmol), sodium tert-butoxide (2.275 g, 7 mmol), and 25 mL of DMSO. The mixture was heated to 100°C for 16 hours, after which the reaction mixture was cooled to room temperature, extracted with dichloromethane, and the solvent removed in vacuo. The product was purified by column chromatography to afford intermediate 7a as a white solid (yield 75%).

[0130] Elemental analysis: Theoretical value: C: 66.77; H: 3.50; N: 4.87; S: 11.14; Se: 13.72; Measured value: C: 66.79; H: 3.49; N: 4.88; S: 11.15; Se: 13.70.

[0131] Synthesis of organic compound M7: Under nitrogen, intermediate 7a (785 mg, 5 mmol), palladium acetate (339 mg, 1.5 mmol), silver oxide (122 mg, 1.5 mmol), and 25 mL of pivalic acid were added to a 100 mL two-necked round-bottom flask. The mixture was reacted at 160°C for 24 h. After cooling to room temperature, the mixture was neutralized with saturated sodium bicarbonate solution, extracted with dichloromethane, and the solvent was removed in vacuo. The product was purified by column chromatography to obtain product M5 as a white solid (yield 15%).

[0132] Elemental analysis: Theoretical value: C: 67.48; H: 2.48; N: 4.92; S: 11.26; Se: 13.87: Measured value: C: 67.47; H: 2.49; N: 4.94; S: 11.25; Se: 13.87.

[0133] Continuing from the above, the following Table 1 is a verification data table of the above-mentioned organic compounds M1 to M7 provided in the Examples of this application.

[0134] Table 1 Organic compound analysis data

[0135] Furthermore, in order to verify the photoluminescence spectra of the organic compounds M1 to M7, the organic compounds M1 to M7 were dissolved in toluene to prepare 10 -5 M solution, and tested its photoluminescence spectrum respectively, and obtained the curve graph shown in Figure 1, wherein the abscissa in Figure 1 is wavelength and the ordinate is normalized EL. After comparative analysis, the luminescence spectrum parameter table of organic compounds M1 to M7 shown in Table 2 below is obtained from Figure 1.

[0136] Table 2 Luminescence parameters of organic compounds

[0137] As can be seen from Table 2 above, the organic compounds M1 to M7 prepared in the examples of the present application have a narrow half-width emission spectrum that can be less than or equal to 21 nm, and a high fluorescence quantum yield, thereby obtaining a high-efficiency, narrow-spectrum green light material.

[0138] Furthermore, an embodiment of the present application also provides an organic light-emitting device, and the organic light-emitting device may include at least one of the organic compounds described in the above embodiments.

[0139] Specifically, referring to Figure 2, the organic light-emitting device 10 includes a first electrode 11, a second electrode 19, and a light-emitting layer 15 arranged between the first electrode 11 and the second electrode 19, and the light-emitting layer 15 includes at least one of the organic compounds, that is, the light-emitting layer 15 may include one or more of the compounds shown in the general formula 1-1 in the above embodiment, which is not limited here.

[0140] In one embodiment, the organic light-emitting device 10 includes a first electrode 11, a hole injection layer 12, a hole transport layer 13, an electron blocking layer 14, a light-emitting layer 15, a hole blocking layer 16, an electron transport layer 17, an electron injection layer 18, and a second electrode 19, which are sequentially disposed on the first electrode 11.

[0141] In the embodiment of the present application, the light-emitting layer 15 includes a host material, a sensitizer, and a light-emitting guest material, and the light-emitting guest material includes at least one of the organic compounds described in the above embodiments.

[0142] The HOMO energy level of the luminescent guest material ranges from -6.0 eV to -5.0 eV, and the LUMO energy level ranges from -3.0 eV to -4.0 eV.

[0143] In one embodiment, the triplet energy level of the host material is higher than the triplet energy level of other materials in the light-emitting layer 15; further, the host material transfers energy to the sensitizer, the triplet energy level of the sensitizer is higher than the triplet energy level of the light-emitting guest material, and the host material and the sensitizer transfer energy to the light-emitting guest material, and the sensitizer can be selected from a phosphorescent material or a thermally activated delayed fluorescent material.

[0144] In one embodiment, the sensitizer is a phosphorescent material containing metal atoms such as Ir, Pd, Pt, Cu, Ag, and Au, with an emission peak at 500-580 nm and phosphorescence lifetime ranging from 1 μs to 100 ms. The HOMO energy level ranges from -6.0 eV to -5.0 eV, and the LUMO energy level ranges from -3.0 eV to -4.0 eV.

[0145] In one embodiment, the absorption spectrum of the luminescent guest material at least partially overlaps with the photoluminescence spectrum of the sensitizer, and the minimum wavelength of the photoluminescence spectrum of the sensitizer is smaller than the maximum wavelength of the absorption spectrum of the luminescent guest material.

[0146] Furthermore, in one embodiment, the first electrode 11 is an anode, whose primary function is to inject holes into the hole injection layer 12, the hole transport layer 13, or the light-emitting layer 15. Preferably, the anode layer 11 is made of a material having high conductivity, a high work function, and an energy level that matches the HOMO energy level of the hole injection material. The material of the anode layer 11 is preferably selected from indium tin oxide (ITO), indium gallium zinc oxide (IGZO), silver, and the like.

[0147] The main function of the hole injection layer 12 is to promote hole injection into the hole transport layer 13 or the light-emitting layer 15 to reduce the voltage of the organic light-emitting device and improve the luminance and device life. Acceptor-type organic materials with deep LUMO energy levels can be selected.

[0148] The main function of the hole transport layer 13 is to transport holes to the light emitting layer 15. The hole transport layer 13 may be composed of one layer of organic material or two layers of organic material. An aromatic amine compound is preferably used.

[0149] The function of the electron blocking layer 14 is to block electrons from diffusing toward the anode, thereby increasing the probability of electrons and holes recombination in the light-emitting layer 15 . The LUMO energy level of the electron blocking layer 14 is higher than that of the light-emitting layer 15 , creating a large energy gap with the light-emitting layer 15 .

[0150] The light-emitting layer 15 includes at least one of the organic compounds provided in the embodiments of the present application.

[0151] The hole blocking layer 16 blocks holes from diffusing toward the second electrode 19 and increases the probability of electrons and holes being recombined in the light-emitting layer 15 .

[0152] The main function of the electron transport layer 17 is to transport electrons from the second electrode 19 to the light-emitting layer 15. Such materials have properties such as a large energy gap, a low HOMO energy level, high electron mobility, and good thermal stability, and aromatic heterocyclic compounds are preferred.

[0153] The main function of the electron injection layer 18 is to promote the injection of electrons from the second electrode 19 into the electron transport layer 17 or the light-emitting layer 15, thereby improving the device's luminance and lifetime. The material of the electron injection layer 18 can preferably be selected from at least one of an alkali metal compound, lithium 8-hydroxyquinolinate (LiQ), and the like.

[0154] The second electrode 19 is a cathode layer, and its main function is to inject electrons into the organic functional layer. It is preferably made of an alloy material with a small work function.

[0155] In addition, the examples of the present application are verified by using organic light-emitting devices prepared with different light-emitting guest materials to demonstrate the improvement effect of the organic compounds provided in the examples of the present application on the performance of organic light-emitting devices.

[0156] The embodiments of the present application provide comparative examples and embodiments 1 to 7, wherein in the comparative examples and embodiments 1 to 7, except for the different luminescent guest materials in the luminescent layer 15 , the other structures and materials of the organic light-emitting devices are the same.

[0157] Specifically, in the comparative example and Examples 1 to 7, the first electrode 11 in the organic light-emitting device is prepared using ITO; the hole injection layer 12 is prepared using HATCN (2,3,6,7,10,11-hexacyano-1,4,5,8,9,12-hexaazatriphenylene) with a thickness of 5 nm; the hole transport layer 13 is prepared using TAPC (4,4'-cyclohexylbis[N,N-di(4-methylphenyl)aniline]) with a thickness of 30 nm; the electron blocking layer 14 is prepared using TCTA (4,4',4"-tris(carbazol-9-yl)triphenylamine) with a thickness of 15 nm; the light-emitting layer 1 5 has a thickness of 20 nm, and is obtained by co-evaporation of a luminescent guest material, Ir(ppy)3 and mCBP in a mass ratio of 2:20:178, while the luminescent guest material in the comparative example is compound ref, and the luminescent guest materials in Examples 1 to 7 are organic compounds 1 to 7, respectively; the hole blocking layer 16 is prepared by using POT2T (ruthenium (II) polypyridine complex) and has a thickness of 10 nm; the electron transport layer 17 is prepared by using ANT-BIZ and has a thickness of 40 nm; the electron injection layer 18 is prepared by using Liq and has a thickness of 1.5 nm; the second electrode is prepared by using Al and has a thickness of 100 nm.

[0158] The structural formulas of the compounds HATCN, TAPC, TCTA, Ir(ppy)3, mCBP, POT2T and ANT-BIZ used in the above-mentioned organic light-emitting devices are shown below.

[0159] Furthermore, in the preparation process of each of the above-mentioned organic light-emitting devices, under high vacuum conditions, the hole injection layer 12, hole transport layer 13, electron blocking layer 14, light-emitting layer 15, hole blocking layer 16, electron transport layer 17, electron injection layer 18 and second electrode 19 are sequentially deposited on a cleaned conductive glass (ITO) substrate, i.e., on the first electrode 11. Then, at a current density of 10 mA / cm 2 The luminescence characteristics of the prepared device were recorded under the following conditions, and the data shown in Table 3 were obtained.

[0160] Table 3 Performance data of organic light-emitting devices

[0161] As can be seen from Table 3 above, compared to the comparative example, in Examples 1 to 7, under the same driving current, the voltage is reduced to below 3.5 V, the external quantum efficiency (EQE) is increased to above 28.5%, and the service life (LT95) is increased to above 60 hr. This indicates that the organic light-emitting devices prepared using the organic compounds provided in the examples of the present application can effectively improve the external quantum efficiency and service life of the organic light-emitting devices, reduce the operating voltage, and improve the thermal stability of the organic light-emitting devices.

[0162] In summary, in the organic compounds provided in the embodiments of the present application, by introducing heteroaryl groups into carbon nitrogen compounds, by increasing the n-conjugated plane of the organic compound, the energy gap is reduced to cause the spectrum to red-shift, and at the same time the fluorescence quantum yield of the organic compound is improved to obtain a high-efficiency, narrow-spectrum green light material. The rigid molecular structure of the organic compound is conducive to improving thermal stability. When the organic compound is applied to an organic light-emitting device, the luminous efficiency, color purity and life of the organic light-emitting device can be improved.

[0163] In addition, an embodiment of the present application further provides a display device, which includes the organic light-emitting device described in the above embodiment.

[0164] The display device can be used for lighting or display, and can be specifically used for mobile, vehicle-mounted, AR / VR, notebook, monitor, television and other displays.

[0165] It is understandable that since the display device provided in the embodiment of the present application includes the organic light-emitting device described in the above embodiment, the display device has the same beneficial effects as the above organic light-emitting device, which will not be described in detail here.

[0166] In the above embodiments, the description of each embodiment has its own focus. For parts that are not described in detail in a certain embodiment, reference can be made to the relevant descriptions of other embodiments.

[0167] The above is a detailed introduction to an organic compound, an organic light-emitting device and a display device provided in the embodiments of the present application. Specific examples are used herein to illustrate the principles and implementation methods of the present application. The description of the above embodiments is only used to help understand the technical solutions and core ideas of the present application. Ordinary technicians in this field should understand that they can still modify the technical solutions recorded in the aforementioned embodiments, or make equivalent replacements for some of the technical features therein; and these modifications or replacements do not cause the essence of the corresponding technical solutions to deviate from the scope of the technical solutions of the embodiments of the present application.

Claims

1. An organic compound, the general structural formula of the organic compound is shown in Formula 1-1 below: in, M is selected from a substituted or unsubstituted aromatic group having 5 to 40 carbon atoms; Ar1 and Ar2 are each independently selected from a substituted or unsubstituted heteroaryl group having 4 to 20 carbon atoms; R1, R2, R3, R4, R5 and R6 are each independently selected from one of an electron-donating group and an electron-withdrawing group, and any two adjacent ones of R1, R2, R3, R4, R5 and R6 may form a ring or not.

2. The organic compound according to claim 1, wherein Ar1 and Ar2 are each selected from a substituted or unsubstituted heteroaryl group having 4 to 20 carbon atoms, and the heteroatom is selected from at least one of N, O, S, Se and Te.

3. The organic compound according to claim 1, wherein R1, R2, R3, R4, R5 and R6 are each independently selected from at least one of H, D, a straight-chain hydrocarbon group having 1 to 60 carbon atoms, a branched hydrocarbon group having 1 to 60 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted aryl group having 5 to 40 carbon atoms, a substituted or unsubstituted heteroaryl group having 4 to 25 carbon atoms, a substituted or unsubstituted ether group having 5 to 20 carbon atoms, a carbonyl group, a carboxyl group, a nitro group and a cyano group.

4. The organic compound according to claim 1, wherein The general structural formula of the organic compound is shown in Formula 1-2 below: Among them, R7, R8, R9 and R 10 Each independently selected from a single bond, H, D, a linear hydrocarbon group having 1 to 60 carbon atoms, a branched hydrocarbon group having 1 to 60 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted aryl group having 5 to 40 carbon atoms, a substituted or unsubstituted heteroaryl group having 4 to 25 carbon atoms, at least one of a substituted or unsubstituted ether group having 5 to 20 carbon atoms, a carbonyl group, a carboxyl group, a nitro group, and a cyano group; the heteroatom in the substituted or unsubstituted heteroaryl group having 4 to 25 carbon atoms is at least one selected from Si, N, O, S, and Se; R7, R8, R9, and R 10 Any two adjacent ones form a ring or not; X is selected from one of -NL1-, -O-, -S-, -Se- and -Te-; L1 is selected from one of H, D, a linear hydrocarbon group having 1 to 60 carbon atoms, a branched hydrocarbon group having 1 to 60 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted aryl group having 5 to 40 carbon atoms, and a substituted or unsubstituted heteroaryl group having 4 to 20 carbon atoms; the heteroatom in the substituted or unsubstituted heteroaryl group having 4 to 20 carbon atoms is selected from at least one of Si, N, O, S, Se and Te; When X is selected from -NL1-, L1 and R7, R8, R9 and R 10 One of them is cyclic or not.

5. The organic compound according to claim 4, wherein The general structural formula of the organic compound is shown in Formula 1-3 below: Ar3 is selected from a substituted or unsubstituted heteroaryl group having 4 to 20 carbon atoms, and in the substituted or unsubstituted heteroaryl group having 4 to 20 carbon atoms, the heteroatom is selected from at least one of N, O, S, Se and Te.

6. The organic compound according to claim 5, wherein At least two of Ar1, Ar2 and Ar3 are selected from the same group.

7. The organic compound according to claim 5, wherein Ar1, Ar2 and Ar3 are each independently selected from at least one of a substituted or unsubstituted furyl group, a substituted or unsubstituted thienyl group, a substituted or unsubstituted pyrrolyl group, a substituted or unsubstituted benzofuranyl group, a substituted or unsubstituted benzothienyl group, and a substituted or unsubstituted indolyl group.

8. The organic compound according to any one of claims 1 to 7, wherein The organic compound is selected from one of the following compounds:

9. An organic light-emitting device, comprising a first electrode, a second electrode, and a light-emitting layer disposed between the first electrode and the second electrode, wherein the light-emitting layer comprises at least one organic compound; The general structural formula of the organic compound is shown in Formula 1-1 below: in, M is selected from a substituted or unsubstituted aromatic group having 5 to 40 carbon atoms; Ar1 and Ar2 are each independently selected from a substituted or unsubstituted heteroaryl group having 4 to 20 carbon atoms; R1, R2, R3, R4, R5 and R6 are each independently selected from one of an electron-donating group and an electron-withdrawing group, and any two adjacent ones of R1, R2, R3, R4, R5 and R6 may form a ring or not.

10. The organic light emitting device according to claim 9, wherein Ar1 and Ar2 are each selected from a substituted or unsubstituted heteroaryl group having 4 to 20 carbon atoms, and the heteroatom is selected from at least one of N, O, S, Se and Te.

11. The organic light emitting device according to claim 9, wherein R1, R2, R3, R4, R5 and R6 are each independently selected from at least one of H, D, a straight-chain hydrocarbon group having 1 to 60 carbon atoms, a branched hydrocarbon group having 1 to 60 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted aryl group having 5 to 40 carbon atoms, a substituted or unsubstituted heteroaryl group having 4 to 25 carbon atoms, a substituted or unsubstituted ether group having 5 to 20 carbon atoms, a carbonyl group, a carboxyl group, a nitro group and a cyano group.

12. The organic light emitting device according to claim 9, wherein The general structural formula of the organic compound is shown in Formula 1-2 below: Among them, R7, R8, R9 and R 10 Each independently selected from a single bond, H, D, a linear hydrocarbon group having 1 to 60 carbon atoms, a branched hydrocarbon group having 1 to 60 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted aryl group having 5 to 40 carbon atoms, a substituted or unsubstituted heteroaryl group having 4 to 25 carbon atoms, at least one of a substituted or unsubstituted ether group having 5 to 20 carbon atoms, a carbonyl group, a carboxyl group, a nitro group, and a cyano group; the heteroatom in the substituted or unsubstituted heteroaryl group having 4 to 25 carbon atoms is at least one selected from Si, N, O, S, and Se; R7, R8, R9, and R 10 Any two adjacent ones form a ring or not; X is selected from one of -NL1-, -O-, -S-, -Se- and -Te-; L1 is selected from one of H, D, a linear hydrocarbon group having 1 to 60 carbon atoms, a branched hydrocarbon group having 1 to 60 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted aryl group having 5 to 40 carbon atoms, and a substituted or unsubstituted heteroaryl group having 4 to 20 carbon atoms; the heteroatom in the substituted or unsubstituted heteroaryl group having 4 to 20 carbon atoms is selected from at least one of Si, N, O, S, Se and Te; When X is selected from -NL1-, L1 and R7, R8, R9 and R 10 One of them is cyclic or not.

13. The organic light emitting device according to claim 12, wherein: The general structural formula of the organic compound is shown in Formula 1-3 below: Ar3 is selected from a substituted or unsubstituted heteroaryl group having 4 to 20 carbon atoms, and in the substituted or unsubstituted heteroaryl group having 4 to 20 carbon atoms, the heteroatom is selected from at least one of N, O, S, Se and Te.

14. The organic light emitting device according to claim 13, wherein: At least two of Ar1, Ar2 and Ar3 are selected from the same group.

15. The organic light emitting device according to claim 13, wherein Ar1, Ar2 and Ar3 are each independently selected from at least one of a substituted or unsubstituted furyl group, a substituted or unsubstituted thienyl group, a substituted or unsubstituted pyrrolyl group, a substituted or unsubstituted benzofuranyl group, a substituted or unsubstituted benzothienyl group, and a substituted or unsubstituted indolyl group.

16. The organic light emitting device according to claim 9, wherein: The light-emitting layer includes a host material, a sensitizer, and a light-emitting guest material, and the light-emitting guest material includes at least one of the organic compounds.

17. The organic light emitting device according to claim 9, wherein: The absorption spectrum of the luminescent guest material at least partially overlaps with the photoluminescence spectrum of the sensitizer.

18. A display device comprising an organic light-emitting device, the organic light-emitting device comprising a first electrode, a second electrode, and a light-emitting layer disposed between the first electrode and the second electrode, wherein the light-emitting layer comprises at least one organic compound; The general structural formula of the organic compound is shown in Formula 1-1 below: in, M is selected from a substituted or unsubstituted aromatic group having 5 to 40 carbon atoms; Ar1 and Ar2 are each independently selected from a substituted or unsubstituted heteroaryl group having 4 to 20 carbon atoms; R1, R2, R3, R4, R5 and R6 are each independently selected from one of an electron-donating group and an electron-withdrawing group, and any two adjacent ones of R1, R2, R3, R4, R5 and R6 may form a ring or not.

19. The display device according to claim 18, wherein Ar1 and Ar2 are each selected from a substituted or unsubstituted heteroaryl group having 4 to 20 carbon atoms, and the heteroatom is selected from at least one of N, O, S, Se and Te.

20. The display device according to claim 18, wherein R1, R2, R3, R4, R5 and R6 are each independently selected from at least one of H, D, a straight-chain hydrocarbon group having 1 to 60 carbon atoms, a branched hydrocarbon group having 1 to 60 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted aryl group having 5 to 40 carbon atoms, a substituted or unsubstituted heteroaryl group having 4 to 25 carbon atoms, a substituted or unsubstituted ether group having 5 to 20 carbon atoms, a carbonyl group, a carboxyl group, a nitro group and a cyano group.

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