A compound, an organic optoelectronic device and a display or illumination device

Abstract

The present application relates to the field of organic electroluminescent materials, in particular to a kind of compound, organic optoelectronic device and display or lighting device.The chemical structure of the compound is as shown in formula (I)-(VI):The compound of the present application is applied to organic device, can make device have higher luminous efficiency, thereby improving the efficiency of device, while molecule has high stability, can further improve the luminous efficiency and service life of device.

Description

Technical Field

[0001] This invention relates to the field of organic electroluminescent materials, and in particular to a compound, an organic optoelectronic device, and a display or lighting device. Background Technology

[0002] Organic light-emitting diodes (OLEDs) are a type of device with a sandwich-like structure, consisting of positive and negative electrode layers and an organic functional material layer sandwiched between them. Currently, this technology is widely used in display panels for new lighting fixtures, smartphones, and tablets, and is expected to expand further into large-size display products such as televisions. It is a rapidly developing and technologically demanding new display technology. The application of OLED materials in information display materials and organic optoelectronic materials has significant research value and promising application prospects. With the development of multimedia information technology, the performance requirements for flat panel display devices are becoming increasingly stringent. Currently, the main display technologies include plasma display devices, field emission display devices, and organic light-emitting diodes (OLEDs). Among them, OLEDs possess a series of advantages such as self-illumination, low-voltage DC drive, all-solid-state operation, wide viewing angle, and rich colors. Compared with liquid crystal displays (LCDs), OLEDs do not require a backlight, have a wider viewing angle, lower power consumption, and a response speed 1000 times faster than LCDs. Therefore, OLEDs have a broader application prospect. Since OLEDs were first reported, many scholars have dedicated themselves to researching how to improve device efficiency and stability. Forrest and Thompson's research group discovered that transition metal complexes can be applied to phosphorescent OLEDs. Phosphorescent materials exhibit strong spin-orbit coupling, simultaneously utilizing singlet and triplet excitons, theoretically achieving 100% quantum efficiency within phosphorescent OLED devices. In recent years, research on metal complex phosphorescent materials (Ph-OLEDs) has progressed rapidly. For example, the luminescence properties of metal coordination compounds such as rhenium (I), ruthenium (II), osmium (II), iridium (I, III), and platinum (II) have been extensively studied theoretically and experimentally, demonstrating excellent luminescence properties and broad application prospects. Metal complexes absorb electrons in the ultraviolet region and emit electrons in the visible light region, making them excellent luminescent materials. Currently, phosphorescent materials suffer from low lifetimes and poor device stability; designing materials with better performance remains a pressing issue for researchers. Summary of the Invention

[0003] In order to overcome the defects existing in the prior art, the purpose of this invention is to provide a compound, an organic optoelectronic device and a display or lighting device, wherein the organic optoelectronic device has high luminous efficiency and improved lifespan.

[0004] To achieve the above and other related objectives, the present invention provides a compound, the chemical structure of which is shown in formulas (I) to (VI):

[0005]

[0006] In equations (Ⅰ) to (Ⅵ):

[0007] M is selected from beryllium, magnesium, aluminum, calcium, titanium, manganese, cobalt, copper, zinc, gallium, germanium, zirconium, ruthenium, rhodium, palladium, silver, rhenium, platinum, or gold;

[0008] L1-L4 are independently selected from single bonds, O, S, NR1, CR2R3, BR4, SiR5R6, Se, R7R8P=O, SO, or SO2;

[0009] X1-X4 are independently selected from single bonds, O, S, or NR9;

[0010] A, B, C, D, and E are each independently selected from O, S, and COO. - Phosphoryl derivatives, substituted or unsubstituted C6-C60 aryl groups, substituted or unsubstituted C5-C60 heteroaryl groups, or fused cyclic groups as shown below; and at least one of A, B, C, D, and E is selected from the fused cyclic groups shown below:

[0011]

[0012] Among them, Z1-Z9 are each independently selected from -CR 10 R 11 -、-NR 12 -, O or S; Ar is selected from substituted or unsubstituted C6-C60 aryl or substituted or unsubstituted C5-C60 heteroaryl;

[0013] R1-R 12 It is selected from hydrogen, deuterium, halogen, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C1-C12 alkoxy, substituted or unsubstituted C1-C12 alkylthio, substituted or unsubstituted C3-C18 cycloalkyl, substituted or unsubstituted C3-C18 heterocycloalkyl, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C2-C30 heteroaryl.

[0014] Another aspect of the present invention provides an organic layer comprising the compounds described above.

[0015] Another aspect of the present invention provides an organic optoelectronic device, which includes a first electrode, a second electrode and an organic layer as described in the present invention, wherein the organic layer is a light-emitting layer.

[0016] Another aspect of the present invention provides a display or lighting device, including organic optoelectronic devices as described above.

[0017] Compared with the prior art, the beneficial effects of the present invention are as follows:

[0018] The compounds provided by this invention, due to the introduction of fused ring groups, not only adjust the HOMO and LUMO energy levels of the compounds but also make the molecular packing more loosely. This not only lowers the sublimation temperature, making the vapor deposition process more convenient, but also reduces the intermolecular quenching process, thereby improving the device lifetime. Furthermore, fused rings offer better stability compared to ordinary alkyl rings, resulting in better thermal stability for the compounds of this invention. When applied to organic devices, the compounds of this invention enable devices to possess high efficiency, while the molecules exhibit high stability, further enhancing the luminous efficiency and lifespan of the devices. Detailed Implementation

[0019] The following details specific embodiments of the disclosed compounds and their applications in organic optoelectronic devices. Those skilled in the art can easily understand other advantages and effects of the present invention from the content disclosed in this specification. The present invention can also be implemented or applied through other different specific embodiments, and various details in this specification can be modified or changed based on different viewpoints and applications without departing from the spirit of the present invention.

[0020] Before further describing specific embodiments of the present invention, it should be understood that the scope of protection of the present invention is not limited to the specific embodiments described below; it should also be understood that the terminology used in the embodiments of the present invention is for describing specific embodiments and not for limiting the scope of protection of the present invention; in the specification and claims of the present invention, unless otherwise expressly stated in the text, the singular forms "a", "an" and "this" include the plural forms.

[0021] When numerical ranges are given in the embodiments, it should be understood that, unless otherwise stated in the present invention, both endpoints of each numerical range and any value between the two endpoints may be selected. Unless otherwise defined, all technical and scientific terms used in this invention have the same meaning as commonly understood by one of ordinary skill in the art. In addition to the specific methods, apparatus, and materials used in the embodiments, based on the knowledge of the prior art possessed by one of ordinary skill in the art and the description of this invention, any prior art methods, apparatus, and materials similar to or equivalent to those described, apparatus, and materials in the embodiments of this invention may be used to implement the present invention.

[0022] Through extensive research and exploration, the inventors of this invention have provided a cycloalkane compound. When applied to organic devices, this compound enables the devices to possess high efficiency, while the molecules exhibit high stability, further enhancing the luminous efficiency and lifespan of the devices. Based on this, this invention was completed.

[0023] Examples of substituents in this invention are described below, but the substituents are not limited thereto:

[0024] "Substituted or unsubstituted" means substituted with one or more substituents selected from the following: deuterium, halogen group, nitrile group, nitro group, hydroxyl group, carbonyl group, ester group, imide group, amino group, phosphine oxide group, alkoxy group, aryloxy group, alkylthio group, arylthio group, alkylsulfonyl group, arylsulfonyl group, silyl group, boron group, alkyl group, cycloalkyl group, alkenyl group, aryl group, aralkyl group, aryl-alkenyl group, alkylaryl group, alkylamine group, aralkylamine group, heteroarylamine group, arylamine group, arylphosphinyl group and heteroaryl group, acenaphthyl group, compound group, or unsubstituted; or substituted with a substituent that connects two or more substituents from the examples above, or unsubstituted. For example, "substituent that connects two or more substituents" can include biphenyl, that is, biphenyl can be aryl, or a substituent that connects two phenyl groups.

[0025] [Alkyl] may be straight-chain or branched, and the number of carbon atoms is not particularly limited. In some embodiments, alkyl includes, but is not limited to, methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, n-heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 1-ethyl-propyl, 1,1-dimethyl-propyl, isohexyl, 4-methylhexyl, and 5-methylhexyl.

[0026] The above description of alkyl groups can also be used for alkyl groups in aralkyl, aralkylamine, alkylaryl, and alkylamine groups.

[0027] [Heteroalkyl] can be a straight-chain or branched alkyl group containing heteroatoms, and the number of carbon atoms is not particularly limited. In some embodiments, heteroalkyl includes, but is not limited to, alkoxy, alkylthio, alkylsulfonyl, etc. Alkoxy may include, for example, methoxy, ethoxy, n-propoxy, isopropoxy, i-propyloxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentoxy, neopentoxy, isopentoxy, n-hexyloxy, 3,3-dimethylbutoxy, 2-ethylbutoxy, n-octoxy, n-nonoxy, n-decoxy, benzyloxy, p-methylbenzyloxy, etc. Alkylthio groups may include, but are not limited to, methylthio, ethylthio, n-propylthio, isopropylthio, isopropylthio, n-butylthio, isobutylthio, tert-butylthio, sec-butylthio, n-pentylthio, neopentylthio, isopentylthio, n-hexylthio, 3,3-dimethylbutylthio, 2-ethylbutylthio, n-octylthio, n-nonylthio, n-decylthio, benzylthio, etc.

[0028]

Cycloalkyl

[0029] [Heterocyclic alkyl] can be a cycloalkyl group containing heteroatoms, and the number of carbon atoms is not particularly limited. In some embodiments, heterocyclic alkyl groups include, but are not limited to, those containing heteroatoms. wait.

[0030]

Aryl

[0031] The above description of aryl can be applied to arylene, the difference being that arylene is divalent.

[0032] The above description of aryl groups can be applied to aryl groups in the following categories: aryloxy, arylthio, arylsulfonyl, arylphosphinyl, aralkyl, arylalkylamine, arylenyl, alkylaryl, arylamine, and arylheteroarylamine.

[0033] [Heteroaryl] Contains one or more of N, O, P, S, Si, and Se as heteroatoms. Heteroaryl groups include, but are not limited to, pyridinyl, pyrroloyl, pyrimidinyl, pyridazinyl, furanyl, thiopheneyl, imidazolyl, pyrazolyl, azole, isozolyl, thiazolyl, isothiazolyl, triazolyl, diazolyl, thiadiazolyl, dithiazolyl, tetrazolyl, pyranyl, thiaranyl, pyrazinyl, azinyl, thiazolyl, dioxazinyl, dioxazinyl, triazinyl, tetraazinyl, quinolinyl, isoquinolinyl, quinolinyl, quinazolinyl, quinoxalinyl, naphridinyl, acridineyl, xanthyl, phenanthridineyl, diazanaphthyl, triazaindenyl, indoleyl, dihydroindoleyl, nitro-indenyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinyl Pyrazinyl, benzothiazolyl, benzoxazolyl, benzoimidazolyl, benzothiophene, benzofuranyl, dibenzothiophene, dibenzofuranyl, carbazoleyl, benzocarbazoleyl, dibenzocarbazoleyl, indolocarbazoleyl, indocarbazoleyl, phenazinyl, imidazopyridyl, phenazinyl, phenanthrinyl, phenthiazolyl, imidazopyridyl, imidazophenanthrinyl, benzoimidazoquinazolinyl, benzoimidazophenanthrinyl, spiro[fluorene-9,9'-oxazanthracene], phenylbinaphthyl, dinaphthofuranyl, naphthobenzofuranyl, dinaphthiophene, naphthobenzothiophene, triphenylphosphine oxide, triphenylborane, etc.

[0034] The above description of heteroaryl groups can be applied to heteroaryl groups in heteroaryl amines and aryl heteroaryl amines.

[0035] The above description of heteroaryl groups can be applied to hypoaryl groups, the difference being that hypoaryl groups are divalent.

[0036] In one aspect, the present invention provides a compound, the chemical structure of which is shown in formulas (I) to (VI):

[0037]

[0038] In equations (Ⅰ) to (Ⅵ):

[0039] M is selected from beryllium, magnesium, aluminum, calcium, titanium, manganese, cobalt, copper, zinc, gallium, germanium, zirconium, ruthenium, rhodium, palladium, silver, rhenium, platinum, or gold.

[0040] L1-L4 are independently selected from single bonds, O, S, NR1, CR2R3, BR4, SiR5R6, Se, R7R8P=O, SO, or SO2.

[0041] X1-X4 are independently selected from single bonds, O, S, or NR9.

[0042] A, B, C, D, and E are each independently selected from O, S, and COO. -Phosphoryl derivatives, substituted or unsubstituted C6-C60 aryl groups, substituted or unsubstituted C5-C60 heteroaryl groups, or fused cyclic groups as shown below; and at least one of A, B, C, and D is selected from the fused cyclic groups shown below:

[0043]

[0044] Among them, Z1-Z9 are each independently selected from -CR 10 R 11 -、-NR 12 -, O, or S; Ar is selected from substituted or unsubstituted C6-C60 aryl groups or substituted or unsubstituted C5-C60 heteroaryl groups. Taking A as an example, the atom on Ar in the above-mentioned fused cyclic group can be bonded to X1, L1, L2.

[0045] R1-R 12 It is selected from hydrogen, deuterium, halogen, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C1-C12 alkoxy, substituted or unsubstituted C1-C12 alkylthio, substituted or unsubstituted C3-C18 cycloalkyl, substituted or unsubstituted C3-C18 heterocycloalkyl, substituted or unsubstituted C6-C30 aryl, or substituted or unsubstituted C2-C30 heteroaryl.

[0046] Phosphorus oxy derivatives, for example, can be R 15 R 16 P = O. R 15 R 16 Each is selected from hydrogen, deuterium, halogen, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C1-C12 alkoxy, substituted or unsubstituted C1-C12 alkylthio, substituted or unsubstituted C3-C18 cycloalkyl, substituted or unsubstituted C3-C18 heterocycloalkyl, substituted or unsubstituted C6-C30 aryl, or substituted or unsubstituted C2-C30 heteroaryl. More, for example, R 15 R 16 Each is selected from phenyl, etc.

[0047] The compounds of the present invention may be selected from one or more of the structures shown in formulas (I) to (VI).

[0048] In some embodiments of the present invention, at least one of A, B, C, D, and E is selected from the following cyclic groups:

[0049]

[0050]

[0051] Ar is selected from substituted or unsubstituted C6-C60 aryl groups and substituted or unsubstituted C5-C60 heteroaryl groups; the atoms on Ar in the above-mentioned cyclic groups can be bonded to X1, L1, and L2. In some embodiments, Ar is selected from the following groups, substituted or unsubstituted: phenyl, biphenyl, terphenyl, tetraphenyl, pentaphenyl, naphthyl, anthracene, phenanthryl, pyrene, peryl, fluorenyl, pyridyl, pyrrole, pyrimidinyl, pyridazinyl, furanyl, thiophene, imidazolyl, pyrazolyl, azole, isozolyl, thiazolyl, isothiazolyl, triazolyl, diazolyl, thiadiazolyl, dithiazolyl, tetrazolyl, pyranyl, thiaranyl, pyrazinyl, azinyl, thiazolyl, dioxazinyl, dioxazinyl, triazinyl, tetraazinyl, quinolinyl, isoquinolinyl, quinolinyl, quinazolinyl, quinoxolinyl, naphthidyl, acridineyl, xanthyl, phenanthridineyl, diazanaphthyl, triazaindenyl, indoleyl, dihydroindoleyl The following are listed: [List of compounds, including] ...

[0052] R 13 R 14 Each is independently selected from hydrogen, deuterium, halogen, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C1-C12 alkoxy, substituted or unsubstituted C1-C12 alkylthio, substituted or unsubstituted C3-C18 cycloalkyl, substituted or unsubstituted C3-C18 heterocycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl.

[0053] In a preferred embodiment, at least one of A, B, C, D, and E is selected from the following structural groups:

[0054] Among them, Ar and R 13 R 14The choices are the same as before. At most three of A, B, C, D, and E are selected from O, S, carboxyl, phosphorooxy derivatives (further selection of phosphorooxy derivatives is as before), or substituted or unsubstituted benzene rings, substituted or unsubstituted naphthyl rings, substituted or unsubstituted phenanthrene rings, substituted or unsubstituted phenanthroline derivatives, substituted or unsubstituted biphenyls, substituted or unsubstituted terphenyls, substituted or unsubstituted pyridines, substituted or unsubstituted imidazoles, substituted or unsubstituted thiazoles, substituted or unsubstituted oxazoles, substituted or unsubstituted benzimidazoles, substituted or unsubstituted benzothiazoles, substituted or unsubstituted benzoxazoles, substituted or unsubstituted pyrazines, substituted or... Unsubstituted phenazines, substituted or unsubstituted pyridazines, substituted or unsubstituted triazines, substituted or unsubstituted triazoles, substituted or unsubstituted phosphorus oxides, substituted or unsubstituted phenols, substituted or unsubstituted naphthols, substituted or unsubstituted benzoic acid derivatives, substituted or unsubstituted thiophenes, substituted or unsubstituted naphthiophenes, substituted or unsubstituted carbazoles, substituted or unsubstituted pyrroles, substituted or unsubstituted azafluorene derivatives, substituted or unsubstituted azaspirofluorenes, substituted or unsubstituted azadibenzofurans, substituted or unsubstituted azasubstituted or unsubstituted dibenzothiophenes, or substituted or unsubstituted azacarbazoles, etc.

[0055] More preferably, at least one of A, B, C, D, and E is selected from the following cyclic groups:

[0056]

[0057]

[0058] R 30 ~R 31 Each is independently selected from hydrogen, deuterium, halogen, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C1-C12 alkoxy, substituted or unsubstituted C1-C12 alkylthio, substituted or unsubstituted C3-C18 cycloalkyl, substituted or unsubstituted C3-C18 heterocycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl; preferably, R 30 ~R 31 Each is independently selected from hydrogen, deuterium, methyl, ethyl, isopropyl, tert-butyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, etc.

[0059] m and n are independently selected from 0 to 10 and are integers. Specifically, m and n are independently selected from 0 to 4, 4 to 8, or 8 to 10, etc. More specifically, m and n are independently selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10, etc. When m is greater than or equal to 2, multiple R... 30 They can be the same or different. When n is greater than or equal to 2, multiple R... 31 They can be the same or different.

[0060] X6 and X7 are each independently selected from O, S, and NR. 32 R 32 Each is independently selected from hydrogen, deuterium, halogen, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C1-C12 alkoxy, substituted or unsubstituted C1-C12 alkylthio, substituted or unsubstituted C3-C18 cycloalkyl, substituted or unsubstituted C3-C18 heterocycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl; preferably, R 32 Selected from hydrogen, deuterium, methyl, ethyl, isopropyl, tert-butyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, etc.

[0061] The compounds provided by this invention have chemical structures as shown in formulas (VII) to (XXVII):

[0062]

[0063]

[0064] M is selected from beryllium, magnesium, aluminum, calcium, titanium, manganese, cobalt, copper, zinc, gallium, germanium, zirconium, ruthenium, rhodium, palladium, silver, rhenium, platinum, or gold.

[0065] L5-L7 are independently selected from single bonds, O, S, and NR. 19 CR 20 R 21 BR 22 SiR 23 R 24 、Se、R 25 R 26 P=O, SO, or SO2.

[0066] X5 is selected from single bond, O, S, NR. 27 or CR 28 R 29 .

[0067] R 15 -R 18 It is selected from hydrogen, deuterium, halogen, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C1-C12 alkoxy, substituted or unsubstituted C1-C12 alkylthio, substituted or unsubstituted C3-C18 cycloalkyl, substituted or unsubstituted C3-C18 heterocycloalkyl, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C2-C30 heteroaryl.

[0068] The compounds of the present invention may be selected from one or more of the structures shown in formulas (VII) to (XXVII).

[0069] A1~A22, B1~B22, C1~C22, D1~D22, E1~E21, F1~F20, and G1~G19 are each independently selected from substituted or unsubstituted aryl groups of C6-C60 or substituted or unsubstituted heteroaryl groups of C5-C60, or the following cyclic groups; and at least one of them is selected from the following cyclic groups:

[0070]

[0071] Among them, Z1-Z9 are each independently selected from -CR 10 R 11 -、-NR 12 -, O or S; Ar is selected from substituted or unsubstituted C6-C60 aryl groups or substituted or unsubstituted C5-C60 heteroaryl groups.

[0072] In a preferred embodiment, at least one of A1-A22, B1-B22, C1-C22, D1-D22, E1-E21, F1-F20, and G1-G19 is selected from the following cyclic groups;

[0073]

[0074] The atom on Ar in the aforementioned cyclic group can be bonded to adjacent groups in formulas (VI) to (XXVII). Ar, R 13 R 14 Choose the same option as before.

[0075] Furthermore, at most three of A1~A22, B1~B22, C1~C22, D1~D22, E1~E21, F1~F20, and G1~G19 are selected from O, S, carboxyl, phosphooxy derivatives (further selection of phosphooxy derivatives is as above), or substituted or unsubstituted benzene rings, substituted or unsubstituted naphthyl rings, substituted or unsubstituted phenanthrene rings, substituted or unsubstituted phenanthroline derivatives, substituted or unsubstituted biphenyls, substituted or unsubstituted terphenyls, substituted or unsubstituted pyridines, substituted or unsubstituted imidazoles, substituted or unsubstituted thiazoles, substituted or unsubstituted oxazoles, substituted or unsubstituted benzimidazoles, substituted or unsubstituted benzothiazoles, substituted or unsubstituted... Substituted benzoxazoles, substituted or unsubstituted pyrazines, substituted or unsubstituted phenazines, substituted or unsubstituted pyridazines, substituted or unsubstituted triazines, substituted or unsubstituted triazoles, substituted or unsubstituted phosphorus oxides, substituted or unsubstituted phenols, substituted or unsubstituted naphthols, substituted or unsubstituted benzoic acid derivatives, substituted or unsubstituted thiophenes, substituted or unsubstituted naphthiophenes, substituted or unsubstituted carbazoles, substituted or unsubstituted pyrroles, substituted or unsubstituted azafluorene derivatives, substituted or unsubstituted azaspirofluorenes, substituted or unsubstituted azadibenzofurans, substituted or unsubstituted azasubstituted or unsubstituted dibenzothiophenes, or substituted or unsubstituted azacarbazoles. The atom on Ar in the group can be bonded to an adjacent group in formulas (VII) to (XXVII).

[0076] In the compounds provided by this invention, M is selected from Pt, Pd, Zn or Cu.

[0077] The compounds provided by this invention are selected from one or more of the following chemical structures:

[0078]

[0079]

[0080]

[0081]

[0082]

[0083]

[0084]

[0085]

[0086]

[0087]

[0088]

[0089]

[0090]

[0091]

[0092]

[0093] Specifically, the above structure can be unsubstituted or substituted with one or more substituents selected from the following. For example, it can be deuterium, halogen group, nitrile group, nitro group, hydroxyl group, carbonyl group, ester group, imide group, amino group, phosphine oxide group, alkoxy group, aryloxy group, alkyl thio group, aryl thio group, alkyl sulfonyl group, aryl sulfonyl group, silyl group, boron group, alkyl group, cycloalkyl group, alkenyl group, aryl group, aralkyl group, aryl-alkenyl group, alkylaryl group, alkylamine group, aralkylamine group, heteroarylamine group, arylamine group, arylheteroarylamine group, arylphosphyl group, and heteroaryl group, etc.

[0094] The aforementioned organic compounds are polycyclic cyclic compounds. This structure exhibits good thermal stability, suitable HOMO and LUMO energy levels and Eg, high triplet energy level, good carrier mobility, and can match adjacent energy levels, resulting in novel OLED materials with high thermal stability and film formation stability. Applying these compounds to OLED devices as phosphorescent doping materials can effectively improve device efficiency and lifetime.

[0095] Another aspect of the present invention provides an organic layer comprising the compounds described above.

[0096] Another aspect of the present invention provides the use of the compounds and / or organic layers described above in organic optoelectronic devices.

[0097] The organic optoelectronic device provided by this invention includes a first electrode, a second electrode, and one or more organic layers disposed between the first and second electrodes. It is a bottom- or top-emitting device structure. The organic layers can be a single-layer structure or a multilayer tandem structure with two or more organic layers. The organic layers may include at least one of a hole injection layer, a hole transport layer, a light-emitting layer, an electron injection layer, or an electron transport layer. It can be prepared using common methods and materials for preparing organic optoelectronic devices. The organic optoelectronic device of this invention uses a compound as the organic layer.

[0098] In the organic optoelectronic device provided by this invention, the first electrode serves as the anode layer. The anode material can be, for example, a material with a high work function, allowing holes to be smoothly injected into the organic layer. More specifically, it can be a metal, a metal oxide, a combination of metal and oxide, a conductive polymer, etc. The metal oxide can be, for example, indium tin oxide (ITO), zinc oxide, indium oxide, and indium zinc oxide (IZO).

[0099] In the organic optoelectronic device provided by this invention, the second electrode serves as the cathode layer. The cathode material can be, for example, a material with a small work function, allowing electrons to be smoothly injected into the organic layer. The cathode material can be, for example, a metal or a multilayer structure material. Metals can be, for example, magnesium, silver, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, tin, and lead, or alloys thereof. The cathode material is preferably selected from magnesium and silver.

[0100] In the organic optoelectronic device provided by the present invention, the material of the hole injection layer is preferably a material whose highest occupied molecular orbital (HOMO) is between the work function of the anode material and the HOMO of the surrounding organic layer, as a material that can advantageously receive holes from the anode at low voltage.

[0101] In the organic optoelectronic device provided by this invention, the material of the hole transport layer is a material with high hole mobility, suitable for receiving holes from the anode or hole injection layer and transporting the holes to the light-emitting layer. The materials of the hole transport layer include, but are not limited to, organic materials of aryl amines, conductive polymers, and block copolymers having both conjugated and non-conjugated portions.

[0102] In the organic optoelectronic device provided by this invention, the compound provided by this invention can be applied to the light-emitting layer of the device.

[0103] In the organic optoelectronic device provided by the present invention, the material of the electron transport layer is a material with high electron mobility, which is suitable as an advantageous material for receiving electrons from the cathode and transporting electrons to the light-emitting layer.

[0104] In the organic optoelectronic device provided by the present invention, the material of the capping layer usually has a high refractive index, which can help improve the light efficiency of the organic light-emitting device, especially the external light-emitting efficiency.

[0105] The organic optoelectronic devices provided by this invention include organic photovoltaic devices, organic light-emitting devices, organic solar cells, electronic paper, organic photoreceptors, organic thin-film transistors, etc.

[0106] Another aspect of the present invention provides a display or lighting device, including the organic optoelectronic device described in the present invention.

[0107] The following specific examples illustrate the implementation of the present invention.

[0108] Synthesis Example:

[0109] The compounds shown in formulas (I) to (VI) above can be synthesized using known methods. For example, cross-coupling reactions of transition metals such as nickel and palladium can be used. Other synthetic methods use CC-CN coupling reactions of transition metals such as magnesium or zinc. The Suzuki-Buchwald reaction is preferred due to its mild reaction conditions and superior selectivity for various functional groups. The compounds of the present invention are illustrated by the following examples, but are not limited to the compounds and synthetic methods exemplified in these examples. The initial raw materials and solvents of the present invention, as well as some commonly used OLED intermediates, were purchased from domestic OLED intermediate manufacturers; various palladium catalysts, ligands, etc., were purchased from Sigma-Aldrich. 1 H-NMR data were determined using a JEOL (400MHz) nuclear magnetic resonance spectrometer; HPLC data were determined using a Shimadzu LC-20AD high-performance liquid chromatograph.

[0110] The synthesized compound in the examples is:

[0111]

[0112]

[0113] Example 1

[0114] Synthesis of Compound 10

[0115]

[0116] 1) Synthesis of intermediate 10-1

[0117] Under an argon atmosphere, 41.5 g (100 mmol) of compound 10-A, 21.9 g (110 mmol) of compound 10-B, 701 mg of bis(triphenylphosphine)palladium(II) chloride catalyst, 200 mL (300 mmol) of 1.5 M sodium carbonate aqueous solution, and 1000 mL of ethylene glycol dimethyl ether (DME) were added to a reaction vessel. The mixture was heated and stirred overnight at 80 °C. After cooling to room temperature, 800 mL of water was added, and a solid precipitated. The solid was filtered, and the crude product was purified by silica gel column chromatography (eluent: ethyl acetate / petroleum ether) to give 39.8 g of compound 10-1, yield 78%, HPLC purity 99.4%. LC MS: M / Z 509.25 (M+).

[0118] 1H NMR(400MHz,DMSO-d6)δ1.22(d,12H),2.06(s,2H),6.29(m,1H),6.55(m,1H),7.03(m,1H),7.19– 7.34(m,2H),7.39(t,1H),7.47–7.59(m,4H),7.65–7.77(m,2H),8.27(s,1H),8.32–8.43(m,4H).

[0119] 2) Synthesis of Compound 10

[0120] Under an argon atmosphere, 51.0 g (100 mmol) of compound 10-B, 45.7 g (110 mmol) of K₂PtCl₄, 2100 mL of acetic acid, and 300 mL of chloroform were added sequentially to a reaction vessel, and the mixture was refluxed for 4 days. After the reaction was completed, the mixture was neutralized with potassium carbonate and extracted with dichloromethane. The solvent was removed by vacuum extraction of the organic phase. The obtained solid was separated using a silica gel column with a mobile phase of n-hexane / dichloromethane, and then recrystallized from methanol to give 23.2 g of the target compound 10-B with an HPLC purity of 99.9% and a yield of 33%. LC MS: M / Z 702.20 (M+).

[0121] 1 H NMR(400MHz,DMSO-d6)δ1.22(d,12H),2.06(s,2H),6.29(m,1H),6.93(m,1H),7.10–7.27(m,4H),7.29– 7.37(m,1H),7.47–7.57(m,3H),7.81–7.87(m,1H),8.32–8.43(m,2H),8.55–8.63(m,1H),9.22(d,1H).

[0122] Example 2

[0123] Synthesis of Compound 39

[0124]

[0125] Except for the replacement of the starting materials with 39-A and 39-B, the results were the same as in Example 1. LC MS: M / Z 1062.48 (M+). Overall yield: 30%; HPLC purity: 99.9%.

[0126] 1H NMR(400MHz,DMSO-d6)δ1.22(s,12H),1.31(s,8H),1.38(s,8H),1.43(s,8H),1.50(s,4H),7.17–7.26(m,2H),7. 27–7.35(m,2H),7.35–7.54(m,8H),7.69–7.82(m,5H),7.83–7.90(m,2H),8.19(m,1H),8.66(m,1H),9.48(m,1H).

[0127] Example 3

[0128] Synthesis of Compound 54

[0129]

[0130] Except for the change of starting materials to 39-A and 54-B, the synthesis was identical to that in Example 1. LC MS: M / Z 944.40 (M+). Overall yield: 32%; HPLC purity: 99.9%.

[0131] 1 H NMR(400MHz, DMSO-d6)δ1.31(s,8H),1.38(s,8H),1.43(s,8H),1.68–1.91(m,7H),2.77–2.89(m,4H),7.17–7.26(m,3H),7.27–7.3 5(m,3H),7.35–7.46(m,4H),7.46–7.54(m,2H),7.83–7.90(m,3H),8.07–8.18(m,2H),8.19(m,1H),8.66(m,1H),9.26–9.32(m,1H).

[0132] Example 4

[0133] Synthesis of Compound 86

[0134]

[0135] Except for the replacement of the starting materials with 86-A and 86-B, the synthesis was identical to that in Example 1. LC MS: M / Z 875.28 (M+). Overall yield: 31%; HPLC purity: 99.9%.

[0136] 1H NMR (400MHz, DMSO-d6) δ1.22(d,12H),1.48(d,10H),4.63(s,2H),6.55(s,1H),6.74(d,1H),7.23–7.33(m,2H),7.53(m,1H),7.57–7.63( m,1H),7.77(d,1H),7.82–7.90(m,2H),8.13(s,1H),8.24(m,1H),8.27(s,1H),8.29(m,1H),8.69(m,1H),9.00(m,1H),9.43–9.49(m,1H).

[0137] Example 5

[0138] Synthesis of Compound 114

[0139]

[0140] Except for the change of starting materials to 114-A and 114-B, the synthesis was identical to that in Example 1. LC MS: M / Z 835.21 (M+). Overall yield: 31%; HPLC purity: 99.9%.

[0141] 1 H NMR(400MHz,DMSO-d6)δ1.40(s,6H),1.57–1.75(m,2H),1.78–1.96(m,2H),2.64 –2.86(m,2H),3.42–3.64(m,2H),4.24(s,2H),6.55(s,1H),6.74(d,1H),7.01(s ,1H),7.19(m,1H),7.29(t,1H),7.32–7.40(m,1H),7.65(s,1H),7.77(d,1H),7. 82–7.90(m,2H),8.17–8.28(m,3H),8.69(m,1H),9.00(m,1H),9.43–9.49(m,1H).

[0142] Example 6

[0143] Synthesis of Compound 129

[0144]

[0145] 1) Synthesis of intermediate 129-1

[0146] Under an argon atmosphere, 51.0 g (100 mmol) of compound 129-A, 39.6 g (100 mmol) of compound 129-B, 23.4 g (240 mmol) of sodium tert-butoxide, 575 mg (1 mmol%) of bis(benzylacetone)palladium, 580 mg (2 mmol%) of tri-tert-butylphosphine tetrafluoroborate, and 1000 mL of xylene were added to a reaction vessel, and the mixture was heated and stirred at 140 °C for 20 hours. The reaction mixture was cooled to room temperature, 1000 mL of water was added, and the mixture was filtered. The filter cake was washed with copious amounts of water, dried under vacuum, and the crude product was purified by silica gel column chromatography (eluent: ethyl acetate / petroleum ether = 1:100) to give 65.2 g of compound 129-1, with an HPLC purity of 99.5% and a yield of 79%. LC MS: M / Z 515.10 (824.28 M+).

[0147] 1 H NMR(400MHz,DMSO-d6)δ4.27(s,4H),6.79(m,1H),6.97(d,1H),7.19(t,1H),7.18–7.28(m,2H),7.24–7.33(m,3H),7.30–7.36(m,1H),7.33–7.4 2(m,6H),7.40(d,1H),7.44–7.57(m,5H),7.57–7.67(m,2H),7.74–7.84 (m,2H),7.87–7.96(m,4H),8.41(d,1H),8.53–8.59(m,1H),8.62(s,1H).

[0148] 2) Synthesis of compound 129

[0149] Except for the change of starting material to 129-1, the process was identical to step two of Example 1. LC MS: M / Z 1017.23 (M+). Overall yield: 32%; HPLC purity: 99.9%.

[0150] 1 H NMR(400MHz, DMSO-d6)δ4.27(s,4H),6.79(d,1H),6.97(d,1H),7.12(m,1H),7.19–7.26(m,1H),7.23–7.32(m,3H),7.31(d,1H),7.30–7.36(m ,1H),7.33–7.43(m,7H),7.43–7.53(m,5H),7.57–7.65(m,2H),7.77(m ,1H),7.87–7.94(m,3H),8.41(d,1H),8.53–8.59(m,1H),9.57(d,1H).

[0151] Example 7

[0152] Synthesis of Compound 162

[0153]

[0154] Except for the replacement of the starting materials with 162-A and 162-B, the results were the same as in Example 6. LC MS: M / Z 889.24 (M+). Overall yield: 31%; HPLC purity: 99.9%.

[0155] 1 H NMR(400MHz,DMSO-d6)δ1.22(d,12H),1.48(d,4H),6.67(m,1H),6.79(d,1H),6.91–7.00(m,4H),7.07(m,1 H),7.26–7.44(m,3H),7.46–7.66(m,8H),7.70(m,1H),8.09(m,1H),8.16–8.27(m,2H),8.37–8.45(m,1H).

[0156] Example 8

[0157] Synthesis of Compound 170

[0158]

[0159] Except for the starting materials being replaced with 170-A and 170-B, the results were identical to those in Example 6. LC MS: M / Z 887.22 (M+). Overall yield: 30%; HPLC purity: 99.9%.

[0160] 1 H NMR (400MHz, DMSO-d6) δ1.08–1.23(m,2H),1.33–1.70(m,8H),3.42–3.64(m,2H),6.67(m,1H),6.79(d,1H),6.95(m,4H ),7.07(m,1H),7.26–7.67(m,13H),7.75(m,1H),8.09–8.16(m,1H),8.16–8.24(m,1H),8.27(m,1H),8.37–8.45(m,1H).

[0161] Example 9

[0162] Synthesis of Compound 178

[0163]

[0164] Except for the change of starting materials to 178-A and 178-B, the synthesis was identical to that in Example 1. LC MS: M / Z 822.23 (M+). Overall yield: 33%; HPLC purity: 99.9%.

[0165] 1 H NMR (400MHz, DMSO-d6) δ1.68–1.92(m,7H),2.83(m,4H),7.12–7.23(m,2H),7.31(m,3H),7.38(m,2H),7.41–7.50(m,3H),7.49(d,1H ),7.63(m,1H),7.66–7.75(m,2H),7.77(m,1H),7.87–7.96(m,3H),8.17–8.26(m,1H),8.48–8.54(m,1H),8.59(m,2H),9.34(m,1H).

[0166] Example 10

[0167] Synthesis of Compound 207

[0168]

[0169] Except for the replacement of the starting materials with 207-A and 207-B, the results were the same as in Example 1. LC MS: M / Z 743.17 (M+). Overall yield: 32%; HPLC purity: 99.9%.

[0170] 1 H NMR(400MHz,DMSO-d6)δ1.22(d,12H),1.80(s,2H),6.99–7.08(m,2H),7.26–7.35(m,2H),7.3 8–7.49(m,2H),7.49–7.62(m,4H),7.73(m,1H),7.79(m,1H),7.95–8.02(m,1H),9.29(d,1H).

[0171] Example 11

[0172] Synthesis of Compound 215

[0173]

[0174] Except for the starting materials being changed to 215-A and 215-B, everything else was the same as in Example 1. LC MS: M / Z 539.63 (M+). Overall yield: 52%; HPLC purity: 99.9%.

[0175] 1H NMR(400MHz,DMSO-d6)δ1.32–1.51(m,4H),1.59–1.78(m,4H),2.80(m,2H,),6.98–7.09(m,2H), 7.26–7.36(m,2H),7.38–7.63(m,6H),7.73(m,1H),7.79(m,1H),7.94–8.02(m,1H),9.29(d,1H).

[0176] Example 12

[0177] Synthesis of Compound 234

[0178]

[0179] Except for the replacement of the starting materials with 234-A and 234-B, the results were the same as in Example 1. LC MS: M / Z 741.16 (M+). Overall yield: 32%; HPLC purity: 99.9%.

[0180] 1 H NMR(400MHz,DMSO-d6)δ1.50–1.61(m,2H),1.56–1.70(m,4H'),1.80–1.96(m,4H),2.63–2.8 1(m,2H),7.22(s,1H),7.26–7.63(m,6H),7.67–7.91(m,5H),7.94–8.02(m,1H),9.29(d,1H).

[0181] Example 13

[0182] Synthesis of Compound 257

[0183]

[0184] Except for the replacement of the starting materials with 257-A and 257-B, the results were the same as in Example 6. LC MS: M / Z 1227.48 (M+). Overall yield: 31%; HPLC purity: 99.9%.

[0185] 1 H NMR(400MHz,DMSO-d6)δ1.23(d,24H),1.50(s,8H),6.58(m,2H),6.91–7.02(m,4H),7.15(m,4H),7.1 5–7.23(m,2H),7.31(m,4H),7.38(m,4H),7.43(m,2H),7.48(m,4H),7.87–7.93(m,4H),8.82(dd,2H).

[0186] Example 14

[0187] Synthesis of Compound 280

[0188]

[0189] Except for the starting materials being replaced with 280-A and 280-B, the results were the same as in Example 6. LC MS: M / Z 723.16 (M+). Overall yield: 31%; HPLC purity: 99.9%.

[0190] 1 H NMR (400MHz, DMSO-d6) δ1.57–1.76(m,2H),1.76–1.96(m,2H),2.64–2.86(m,2H),3.42–3.65(m,2H),6.81(m,1H),7.12–7.24(m,3H ),7.29–7.40(m,2H),7.44(m,1H),7.59(m,1H),7.85(m,1H),8.16–8.25(m,3H),8.28(d,1H),8.47–8.54(m,1H),8.54–8.64(m,2H).

[0191] Example 15

[0192] Synthesis of Compound 306

[0193]

[0194] Except for the replacement of the starting materials with 306-A and 306-B, the results were the same as in Example 6. LC MS: M / Z 727.12 (M+). Overall yield: 31%; HPLC purity: 99.9%.

[0195] 1 H NMR(400MHz,DMSO-d6)δ4.27(s,4H),6.83–6.93(m,1H),7.19(m,1H),7.32(d,1H),7.36(m,1H),7.44(m,1H),7.60(s,1H ),7.62–7.71(m,2H),7.97–8.03(m,2H),8.17–8.24(m,2H),8.28(d,1H),8.38(m,1H),8.48–8.54(m,1H),8.59(dd,1H).

[0196] Example 16

[0197] Synthesis of Compound 317

[0198]

[0199] Except for the replacement of the starting materials with 317-A and 317-B, the results were the same as in Example 6. LC MS: M / Z 777.21 (M+). Overall yield: 31%; HPLC purity: 99.9%.

[0200] 1 H NMR(400MHz,DMSO-d6)δ1.42–1.55(m,2H),1.50–1.61(m,1H),1.60(s,1H),1.5 6–1.71(m,4H),1.66–1.84(m,1H),1.80–1.96(m,3H),3.42–3.64(m,2H),6.83–6 .93(m,1H),7.12–7.24(m,3H),7.29–7.41(m,2H),7.61–7.72(m,2H),8.00(d,1H ),8.16–8.25(m,3H),8.28(d,1H),8.38(m,1H),8.54–8.64(m,1H),8.69(s,1H).

[0201] Example 17

[0202] Synthesis of Compound 334

[0203]

[0204] Except for the starting materials being changed to 334-A and 334-B, the results were the same as in Example 6. LC MS: M / Z 1027.44 (M+). Overall yield: 33%; HPLC purity: 99.9%.

[0205] 1 H NMR(400MHz,DMSO-d6)δ1.20–1.28(m,32H),1.38(s,5H),1.49(d,12H),7.04(s,1H),7.12–7.23( m,2H),7.32(d,1H),7.36(m,1H),8.13(s,1H),8.17–8.24(m,3H),8.28(d,1H),8.56–8.62(m,1H).

[0206] Example 18

[0207] Synthesis of Compound 359

[0208]

[0209] Except for the replacement of the starting materials with 359-A and 359-B, the results were the same as in Example 1. LC MS: M / Z 798.20 (M+). Overall yield: 31%; HPLC purity: 99.9%.

[0210] 1 H NMR (400MHz, DMSO-d6) δ2.21–2.35(m,2H),2.88–2.98(m,2H),3.71(m,2H),7.02(m,1H),7.15(s,1H),7.23(m,1H),7.25–7.35(m,2H),7.36(m ,1H),7.44–7.66(m,7H),7.68–7.80(m,2H),7.79(d,1H),7.87(d,2H), 8.17–8.23(m,1H),8.38(m,1H),8.46(m,1H),8.69(d,1H),9.48(m,1H).

[0211] Example 19

[0212] Synthesis of Compound 380

[0213]

[0214] Except for the replacement of the starting materials with 380-A and 380-B, the results were the same as in Example 1. LC MS: M / Z 944.31 (M+). Overall yield: 32%; HPLC purity: 99.9%.

[0215] 1 H NMR(400MHz,DMSO-d6)δ1.22(d,12H),1.48(s,4H),6.92(s,1H),7.25–7.44(m,3H),7.39(s,2H),7.44–7.66(m ,10H),7.68–7.80(m,4H),7.79(d,1H),7.87(d,2H),8.17–8.23(m,1H),8.46(m,1H),8.69(m,1H),9.48(m,1H).

[0216] Example 20

[0217] Synthesis of Compound 399

[0218]

[0219] Except for the change of starting materials to 399-A and 399-B, the synthesis was identical to that in Example 1. LC MS: M / Z 826.23 (M+). Overall yield: 31%; HPLC purity: 99.9%.

[0220] 1 H NMR (400MHz, DMSO-d6) δ1.68–1.92(m,6H),2.77–2.88(m,2H),3.55–3.66(m,2H),7.02(m,1H),7.15(s,1H),7.23(m,1H),7.25–7.35(m,2H),7.36 (m,1H),7.44–7.66(m,7H),7.72(m,1H),7.72–7.82(m,2H),7.87(d,2H) ,8.17–8.23(m,1H),8.38(m,1H),8.46(m,1H),8.69(d,1H),9.48(m,1H).

[0221] Example 21

[0222] Synthesis of Compound 412

[0223]

[0224] Except for the replacement of the starting materials with 412-A and 412-B, the results were the same as in Example 1. LC MS: M / Z 910.23 (M+). Overall yield: 32%; HPLC purity: 99.9%.

[0225] 1 H NMR (400MHz, DMSO-d6) δ1.93–2.08(m,2H),2.71–2.97(m,4H),6.97(m,1H),7.19–7.53(m,15H),7.56–7 .66(m,1H),7.67–7.80(m,3H),7.83(m,1H),7.83–7.94(m,3H),8.19(m,1H),8.66(m,1H),9.40(s,1H).

[0226] Example 22

[0227] Synthesis of Compound 439

[0228]

[0229] Except for the replacement of the starting materials with 439-A and 439-B, the results were the same as in Example 1. LC MS: M / Z 938.26 (M+). Overall yield: 33%; HPLC purity: 99.9%.

[0230] 1H NMR (400MHz, DMSO-d6) δ1.68–1.91(m,6H),2.83(m,4H),6.95(t,1H),7.20–7.53(m,14H),7.57–7.65(m,2H ),7.68–7.78(m,2H),7.77(m,1H),7.83(m,1H),7.84–7.93(m,3H),8.19(m,1H),8.66(m,1H),9.40(s,1H).

[0231] Example 23

[0232] Synthesis of Compound 457

[0233]

[0234] Except for the replacement of the starting materials with 457-A and 457-B, the results were the same as in Example 6. LC MS: M / Z 926.27 (M+). Overall yield: 45%; HPLC purity: 99.9%.

[0235] 1 H NMR(400MHz,DMSO-d6)δ1.69(s,6H),1.94–2.08(m,2H),2.63–2.74(m,1H) ,2.70–2.79(m,1H),2.84(m,2H),6.62–6.70(m,1H),6.95(m,1H),7.08–7.2 4(m,9H),7.31–7.41(m,2H),7.44(m,1H),7.44–7.54(m,2H),7.57–7.67(m, 2H),8.14–8.25(m,2H),8.47–8.54(m,1H),8.59(m,3H),8.81–8.87(m,1H).

[0236] Example 24

[0237] Synthesis of Compound 480

[0238]

[0239] Except for the starting materials being changed to 480-A and 480-B, the results were the same as in Example 6. LC MS: M / Z 996.35 (M+). Overall yield: 31%; HPLC purity: 99.9%.

[0240] 1H NMR (400MHz, DMSO-d6) δ1.22(d,12H),1.48(s,4H),1.69(s,5H),6.63–6.69(m,1H),6.95(m,1H),7.08–7.24(m,9H),7.32–7. 41(m,3H),7.41–7.53(m,2H),7.57–7.66(m,3H),8.14–8.24(m,3H),8.48–8.54(m,1H),8.56–8.63(m,2H),8.81–8.87(m,1H).

[0241] Example 25

[0242] Synthesis of Compound 501

[0243]

[0244] Except for the starting materials being changed to 501-A and 501-B, everything else was the same as in Example 1. LC MS: M / Z 996.35 (M+). Overall yield: 34%; HPLC purity: 99.9%.

[0245] 1 H NMR(400MHz,DMSO-d6)δ1.69(s,6H),2.20–2.35(m,2H),2.88–2.98(m,2H),3.71(m,2H),6.95(m,1H),7.10–7.24(m,3H), 7.31–7.41(m,5H),7.58–7.68(m,3H),7.73–7.81(m,1H),8.07(d,1H),8.11–8.16(m,1H),8.16–8.25(m,2H),8.77(s,1H).

[0246] Example 26

[0247] Synthesis of Compound 523

[0248]

[0249] Except for the replacement of the starting materials with 523-A and 523-B, the results were the same as in Example 1. LC MS: M / Z 873.26 (M+). Overall yield: 31%; HPLC purity: 99.9%.

[0250] 1H NMR (400MHz, DMSO-d6) δ1.48(m,4H),1.69(s,6H),1.66–1.82(m,4H),2.41(d,3H),2.70(t,4H),6.62–6.71(m,1H),6.90–7.04(m ,4H),7.07–7.24(m,4H),7.35(d,1H),7.49(m,1H),7.62(d,2H),7.73–7.81(m,1H),8.07(d,1H),8.10–8.18(m,1H),8.84(m,1H).

[0251] Example 27

[0252] Synthesis of Compound 537

[0253]

[0254] Except for the replacement of the starting materials with 537-A and 537-B, the results were the same as in Example 21. LC MS: M / Z 809.16 (M+). Overall yield: 33%; HPLC purity: 99.9%.

[0255] 1 H NMR(400MHz,DMSO-d6)δ1.69(s,6H),5.98(d,1H),6.02(d,1H),6.63–6.69(m,1H),6.89(d,1H),6.95(m,1H),7.08–7.23(m,5H),7.3 2–7.40(m,2H),7.49(m,1H),7.59–7.66(m,2H),7.74–7.80(m,1H),8.07(d,1H),8.11–8.17(m,1H),8.17–8.24(m,1H),8.84(m,1H).

[0256] Example 28

[0257] Synthesis of Compound 555

[0258]

[0259] Except for the replacement of the starting materials with 555-A and 555-B, the results were the same as in Example 6. LC MS: M / Z 876.25 (M+). Overall yield: 36%; HPLC purity: 99.9%.

[0260] 1H NMR (400MHz, DMSO-d6) δ1.57–1.77(m,4H),1.86(m,4H),2.63–2.86(m,4H),3.42–3.65(m,4H),7.12–7.24(m,2H),7.31 (s,1H),7.36(m,2H),7.49–7.59(m,4H),7.63(m,2H),8.16–8.26(m,3H),8.54–8.64(m,3H),8.69(s,1H),9.39(s,1H).

[0261] Example 29

[0262] Synthesis of Compound 581

[0263]

[0264] Except for the starting materials being changed to 581-A and 581-B, everything else was the same as in Example 6. LC MS: M / Z 1030.33 (M+). Overall yield: 33%; HPLC purity: 99.9%.

[0265] 1 H NMR (400MHz, DMSO-d6) δ1.22(d,12H),1.48(s,4H),7.12–7.23(m,2H),7.27(m,1H),7.31–7.59(m,10H),7.59–7.67(m,2H),7.69–7. 76(m,2H),7.76–7.83(m,2H),7.93–8.04(m,2H),8.12(m,1H),8.16–8.26(m,2H),8.26–8.33(m,1H),8.54–8.65(m,3H),9.65(m,1H).

[0266] Example 30

[0267] Synthesis of Compound 599

[0268]

[0269] Except for the starting materials being replaced with 599-A and 599-B, the synthesis was identical to that in Example 6. LC MS: M / Z 924.25 (M+). Overall yield: 36%; HPLC purity: 99.9%.

[0270] 1H NMR(400MHz,DMSO-d6)δ1.63–1.83(m,4H),2.61–2.81(m,4H),3.80(s,1H),6.72(d,1H),6.95(m,2H),7.00–7.17(m,3H),7.23–7.59 (m,10H),7.63(m,1H),7.68–7.78(m,2H),8.01(d,1H),8.12(m,1H),8.16–8.28(m,2H),8.35(m,1H),8.59(m,1H),9.61–9.69(m,1H).

[0271] Example 31

[0272] Synthesis of Compound 615

[0273]

[0274] Except for the starting materials being changed to 615-A and 615-B, the results were the same as in Example 6. LC MS: M / Z 904.29 (M+). Overall yield: 36%; HPLC purity: 99.9%.

[0275] 1 H NMR(400MHz,DMSO-d6)δ1.20(d,6H),1.25(d,6H),1.45–1.52(m,1H),1.49(s,3H),3.80(s,1H),6.95(m,2H),7.06(m,1H),7.07–7.15(m,2H), 7.19(m,1H),7.27(d,1H),7.30–7.45(m,5H),7.49–7.59(m,2H),7.60– 7.68(m,3H),8.20(m,2H),8.21–8.27(m,1H),8.59(m,1H),9.45(d,1H).

[0276] Example 32

[0277] Synthesis of Compound 639

[0278]

[0279] Except for the replacement of the starting materials with 639-A and 639-B, the results were the same as in Example 6. LC MS: M / Z 958.19 (M+). Overall yield: 30%; HPLC purity: 99.9%.

[0280] 1H NMR(400MHz,DMSO-d6)δ3.80(s,1H),5.90(s,2H),5.98(d,1H),6.02(d,1H),6.65 (m,1H),6.75(d,1H),6.79–6.90(m,2H),6.95(m,2H),7.07–7.16(m,2H),7.27(d,1 H),7.32–7.43(m,2H),7.43–7.59(m,3H),7.60–7.66(m,1H),7.69–7.77(m,2H),8 .01(d,1H),8.08–8.16(m,2H),8.17–8.27(m,2H),8.59(m,1H),9.62–9.68(m,1H).

[0281] Example 33

[0282] Synthesis of Compound 658

[0283]

[0284] Except for the change of starting materials to 658-A and 658-B, the results were the same as in Example 6. LC MS: M / Z 871.23 (M+). Overall yield: 30%; HPLC purity: 99.9%.

[0285] 1 H NMR (400MHz, DMSO-d6) δ1.94–2.08(m,2H),2.63–2.79(m,2H),2.84(m,2H),7.08–7.17(m,2H),7.17(m,1H),7.31–7.43(m,3H),7 .43–7.57(m,5H),7.58–7.67(m,2H),7.69–7.83(m,7H),8.01(d,1H),8.12(m,1H),8.16–8.25(m,2H),9.03(d,1H),9.65(m,1H).

[0286] Example 34

[0287] Synthesis of Compound 679

[0288]

[0289] Except for the replacement of the starting materials with 679-A and 679-B, the results were the same as in Example 6. LC MS: M / Z 899.35 (M+). Overall yield: 30%; HPLC purity: 99.9%.

[0290] 1H NMR (400MHz, DMSO-d6) δ1.19–1.27(m,18H),1.38(s,6H),1.48(d,8H),7.08–7.24(m,3H),7.36( m,2H),7.48–7.58(m,2H),7.58–7.67(m,2H),7.73–7.84(m,2H),8.16–8.25(m,4H),9.03(s,1H).

[0291] Example 35

[0292] Synthesis of Compound 699

[0293]

[0294] Except for the starting materials being changed to 699-A and 699-B, everything else was the same as in Example 1. LC MS: M / Z 938.45 (M+). Overall yield: 30%; HPLC purity: 99.9%.

[0295] 1 H NMR(400MHz,DMSO-d6)δ1.20–1.27(m,26H),1.32(s,8H),1.43(s,8H),1.48(t,8H),6.91(m,1H),7.02(m,1H), 7.10(d,1H),7.23(m,1H),7.27–7.35(m,2H),7.76(d,1H),8.33–8.41(m,2H),8.47(s,1H),8.92–8.98(m,1H).

[0296] Example 36

[0297] Synthesis of Compound 720

[0298]

[0299] Except for the change of starting materials to 720-A and 720-B, the synthesis was identical to that in Example 1. LC MS: M / Z 954.38 (M+). Overall yield: 30%; HPLC purity: 99.9%.

[0300] 1H NMR (400MHz, DMSO-d6) δ1.22(d,12H),1.32(s,8H),1.46(d,13H),6.91(m,1H),6.92(s,1H),7.10(d,1H),7.34–7.43(m,1H),7. 43–7.55(m,4H),7.57(s,1H),7.67–7.85(m,5H),7.87–7.95(m,1H),8.06(m,1H),8.32–8.39(m,2H),8.58(m,1H),8.95(d,1H).

[0301] Example 37

[0302] Synthesis of Compound 741

[0303]

[0304] Except for the replacement of the starting materials with 741-A and 741-B, the results were the same as in Example 1. LC MS: M / Z 1124.43 (M+). Overall yield: 32%; HPLC purity: 99.9%.

[0305] 1 H NMR(400MHz,DMSO-d6)δ1.20–1.27(m,24H),1.80(d,4H),6.81(d,2H),6.88 (m,2H),6.98(m,2H),7.13(m,2H),7.19–7.32(m,3H),7.32–7.40(m,4H),7. 43–7.53(m,2H),7.53–7.66(m,3H),7.66–7.73(m,2H),7.77–7.86(m,1H),7 .86–7.93(m,1H),8.05–8.16(m,2H),8.53–8.59(m,1H),9.37–9.43(m,1H).

[0306] Example 38

[0307] Synthesis of Compound 760

[0308]

[0309] Except for the starting materials being replaced with 760-A and 760-B, everything else was the same as in Example 1. LC MS: M / Z 1054.30 (M+). Overall yield: 31%; HPLC purity: 99.9%.

[0310] 1H NMR(400MHz,DMSO-d6)δ1.41(s,8H),4.27(d,8H),6.81(d,2H),7.00(m,2H),7.04–7.12(m,4H),7.19–7.32(m ,8H),7.32–7.40(m,2H),7.44–7.52(m,2H),7.57–7.65(m,3H),7.68(m,1H),8.53–8.59(m,1H),9.30(m,1H).

[0311] Example 39

[0312] Synthesis of Compound 781

[0313]

[0314] Except for the starting materials being changed to 781-A and 781-B, everything else was the same as in Example 1. LC MS: M / Z 898.30 (M+). Overall yield: 33%; HPLC purity: 99.9%.

[0315] 1 H NMR(400MHz,DMSO-d6)δ1.22(d,12H),1.41(s,8H),1.50(s,4H),6.74(d,2H),6.90(m,1H),7.00(d,1 H),7.04(d,1H),7.17–7.33(m,6H),7.56–7.73(m,4H),8.08(m,1H),8.52–8.60(m,1H),9.30(m,1H).

[0316] Example 40

[0317] Synthesis of Compound 796

[0318]

[0319] Except for the starting materials being changed to 796-A and 796-B, the results were the same as in Example 6. LC MS: M / Z 1068.37 (M+). Overall yield: 32%; HPLC purity: 99.9%.

[0320] 1H NMR (400MHz, DMSO-d6) δ1.22(d,12H),1.50(s,4H),6.81(d,2H),6.90(dd,1H),6.96–7.12(m,8H),7.19–7.32(m,7H),7.32–7.37( m,2H),7.34–7.43(m,1H),7.43–7.53(m,2H),7.57–7.63(m,1H),7.66–7.82(m,5H),8.08(d,1H),8.53–8.59(m,1H),9.48(m,1H).

[0321] Example 41

[0322] Synthesis of Compound 807

[0323]

[0324] Except for the starting materials being changed to 807-A and 807-B, everything else was the same as in Example 1. LC MS: M / Z 918.27 (M+). Overall yield: 31%; HPLC purity: 99.9%.

[0325] 1 H NMR(400MHz,DMSO-d6)δ1.22(d,12H),1.50(s,4H),6.74(d,2H),6.90(m,1H),6.97–7.08(m,2H),7.20(s,1H),7.19–7.33(m,4 H),7.34–7.43(m,1H),7.43–7.53(m,2H),7.56–7.64(m,1H),7.65–7.82(m,5H),8.08(m,1H),8.52–8.60(m,1H),9.48(m,1H).

[0326] Example 42

[0327] Synthesis of Compound 840

[0328]

[0329] Except for the replacement of the starting materials with 840-A and 840-B, the results were the same as in Example 1. LC MS: M / Z 893.27 (M+). Overall yield: 32%; HPLC purity: 99.9%.

[0330] 1H NMR (400MHz, DMSO-d6) δ1.22(d,12H),1.80(s,2H),6.79(d,1H),7.02(m,1H),7.26–7.58(m,12H),7.60–7. 70(m,2H),7.70–7.78(m,2H),8.01(d,1H),8.08–8.20(m,2H),8.20(m,1H),8.38–8.44(m,1H),9.65(m,1H).

[0331] Example 43

[0332] Synthesis of Compound 858

[0333]

[0334] Except for the replacement of the starting materials with 858-A and 858-B, the synthesis was identical to that in Example 1. LC MS: M / Z 716.21 (M+). Overall yield: 31%; HPLC purity: 99.9%.

[0335] 1 H NMR(400MHz,DMSO-d6)δ1.22(d,12H),1.48(s,4H),6.83(d,1H),7.01(t,2H),7.31(m,1H),7.50–7.59( m,2H),7.57–7.68(m,2H),7.84(m,1H),7.87–7.97(m,3H),8.03(m,1H),8.33(d,1H),9.29–9.35(m,1H).

[0336] Example 44

[0337] Synthesis of Compound 878

[0338]

[0339] Except for the starting materials being changed to 878-A and 878-B, the synthesis was identical to that in Example 6. LC MS: M / Z 772.27 (M+). Overall yield: 31%; HPLC purity: 99.9%.

[0340] 1H NMR(400MHz,DMSO-d6)δ1.36(s,18),1.43(s,4H),2.61–2.88(m,4H),6.86–6.96(m,2H),7.18(t,1H),7.56–7.69 (m,2H),7.76(d,1H),7.84(m,1H),7.86–7.98(m,2H),8.03(m,1H),8.29(s,1H),8.95(d,1H),9.28–9.36(m,1H).

[0341] Example 45

[0342] Synthesis of Compound 900

[0343]

[0344] Except for the starting materials being replaced with 900-A and 900-B, the synthesis was identical to that in Example 6. LC MS: M / Z 848.31 (M+). Overall yield: 32%; HPLC purity: 99.9%.

[0345] 1 H NMR(400MHz,DMSO-d6)δ1.36(s,18H),2.64–2.86(d,4H),3.42–3.64(m,4H),6.91(m,1H),7.01(t,2H),7.31(m,1H),7.3 5–7.43(m,1H),7.43–7.57(m,3H),7.69–7.80(m,4H),8.29(s,1H),8.51(d,1H),8.71(m,1H),8.95(d,1H),9.25(d,1H).

[0346] Example 46

[0347] Synthesis of Compound 915

[0348]

[0349] Except for the starting materials being changed to 915-A and 915-B, the results were the same as in Example 6. LC MS: M / Z 904.37 (M+). Overall yield: 31%; HPLC purity: 99.9%.

[0350] 1H NMR(400MHz,DMSO-d6)δ1.36(s,18H),1.43(s,12H),6.91(m,1H),6.96–7.08(m,3H),7.31(m,1H),7.35–7.43(m,1H) ,7.43–7.57(m,5H),7.69–7.80(m,5H),7.90(m,1H),8.29(s,1H),8.72–8.78(m,1H),8.95(d,1H),9.47–9.55(m,1H).

[0351] Example 47

[0352] Synthesis of Compound 936

[0353]

[0354] Except for the replacement of the starting materials with 936-A and 936-B, the results were the same as in Example 6. LC MS: M / Z 993.39 (M+). Overall yield: 33%; HPLC purity: 99.9%.

[0355] 1 H NMR(400MHz, DMSO-d6)δ1.36(s,18H),1.43(s,12H),1.48(d,4H),6.91(m,1H),7.01(t,2H),7.27–7.40(m,5H),7.50–7.60(m,2 H),7.60–7.67(m,2H),7.76(d,1H),8.16–8.24(m,2H),8.29(s,1H),8.47(d,1H),8.62(m,1H),8.95(m,1H),9.43–9.49(m,1H).

[0356] Example 48

[0357] Synthesis of Compound 960

[0358]

[0359] Except for the starting materials being replaced with 960-A and 960-B, the synthesis was identical to that in Example 6. LC MS: M / Z 1184.47 (M+). Overall yield: 30%; HPLC purity: 99.9%.

[0360] 1H NMR(400MHz,DMSO-d6)δ1.36(s,24H),1.48(s,4H),1.69(s,6H),6.67(m,1H),6.78–6.86(m,4H),6.94(m,1H), 7.00(m,1H),7.04–7.36(m,15H),7.45(m,2H),7.53(m,1H),7.97(d,1H),8.18–8.24(m,1H),8.56–8.65(m,3H).

[0361] Example 49

[0362] Synthesis of Compound 979

[0363]

[0364] Except for the starting materials being replaced with 979-A and 979-B, everything else was the same as in Example 1. LC MS: M / Z 703.15 (M+). Overall yield: 32%; HPLC purity: 99.9%.

[0365] 1 H NMR(400MHz,DMSO-d6)δ1.64–1.82(m,4H),2.64–2.80(m,4H),6.49(s,2H),6.69(d,1H),6.89–7.02(m,2H),7 .23(t,1H),7.29(m,1H),7.34–7.43(m,2H),7.43–7.53(m,2H),7.69–7.79(m,3H),8.11(m,1H),8.86(m,1H).

[0366] Example 50

[0367] Synthesis of Compound 999

[0368]

[0369] Except for the starting materials being replaced with 999-A and 999-B, everything else was the same as in Example 1. LC MS: M / Z 703.15 (M+). Overall yield: 32%; HPLC purity: 99.9%.

[0370] 1H NMR(400MHz,DMSO-d6)δ1.19–1.28(m,24H),1.49(d,8H),6.49(s,2H),6.60(d,1H),6.67(m,1H),6.80(d,1H),6.9 3(m,1H),7.14(m,1H),7.23(t,1H),7.23–7.33(m,2H),7.38(m,1H),7.74(m,1H),8.11(m,1H),8.82–8.90(m,1H).

[0371] Example 51

[0372] Synthesis of Compound 1020

[0373]

[0374] Except for replacing the starting materials with 1020-A and 1020-B and replacing potassium tetrachloroplatinate with palladium acetate, the synthesis was identical to that in Example 1. LC MS: M / Z 957.38 (M+). Overall yield: 31%; HPLC purity: 99.9%.

[0375] 1 H NMR(400MHz,DMSO-d6)δ1.09–1.21(m,2H),1.31(s,8H),1.41(d,20H),1.49–1.69(m,4H),2.80(d,4H),7.17–7.27(m,2H),7.2 7–7.35(m,2H),7.35–7.54(m,9H),7.69–7.82(m,4H),7.83–7.91(m,2H),8.00(s,1H),8.19(m,1H),8.66(m,1H),9.13(m,1H).

[0376] Example 52

[0377] Synthesis of Compound 1031

[0378]

[0379] Except for replacing the starting materials with 1031-A and 1031-B and replacing potassium tetrachloroplatinate with palladium acetate, the synthesis was identical to that in Example 1. LC MS: M / Z 654.11 (M+). Overall yield: 33%; HPLC purity: 99.9%.

[0380] 1H NMR(400MHz,DMSO-d6)δ1.22(d,12H),1.80(s,2H),6.98–7.09(m,2H),7.26–7.36(m,2H),7.3 8–7.49(m,2H),7.49–7.62(m,4H),7.73(m,1H),7.79(m,1H),7.94–8.02(m,1H),8.94(d,1H).

[0381] Example 53

[0382] Synthesis of Compound 1049

[0383]

[0384] Except for replacing the starting materials with 1049-A and 1049-B and replacing potassium tetrachloroplatinate with copper acetate, the synthesis was identical to that in Example 1. LC MS: M / Z 621.18 (M+). Overall yield: 33%; HPLC purity: 99.9%.

[0385] 1 H NMR (400MHz, DMSO-d6) δ1.94–2.08(m,2H),2.63–2.74(m,1H),2.70–2.79(m,1H,),2.84(m,2H),6.94–7.06(m,2H),7.3 1(m,1H),7.32–7.40(m,2H),7.43–7.53(m,3H),7.56–7.66(m,1H),7.67–7.87(m,5H),8.19–8.26(m,1H),8.75(m,1H).

[0386] Example 54

[0387] Synthesis of Compound 1066

[0388]

[0389] Except for replacing the starting materials with 1066-A and 1066-B and replacing potassium tetrachloroplatinate with copper acetate, the synthesis was identical to that in Example 1. LC MS: M / Z 736.24 (M+). Overall yield: 31%; HPLC purity: 99.9%.

[0390] 1H NMR(400MHz,DMSO-d6)δ1.22(d,12H),1.48(d,4H),7.02(m,1H),7.15(s,1H),7.23(m,1H),7.25–7.35(m,2H),7.36(m,1H), 7.44–7.66(m,7H),7.68–7.80(m,2H),7.79(d,1H),8.17–8.25(m,3H),8.38(m,1H),8.46(m,1H),8.69(m,1H),8.75(m,1H).

[0391] Example 55

[0392] Synthesis of Compound 1088

[0393]

[0394] Except for replacing the starting materials with 1088-A and 1088-B and replacing potassium tetrachloroplatinate with zinc acetate, the synthesis was identical to that in Example 1. LC MS: M / Z 784.31 (M+). Overall yield: 33%; HPLC purity: 99.9%.

[0395] 1 H NMR(400MHz,DMSO-d6)δ1.19–1.28(m,25H),1.48(d,8H),6.55(s,1H),6.74(d,1H),7.19(m,1H),7.29(t,1H), 7.32–7.45(m,3H),7.77(d,1H),7.86(m,1H),8.02(d,1H),8.16–8.29(m,2H),8.65–8.77(m,2H),9.00(m,1H).

[0396] Example 56

[0397] Synthesis of Compound 1098

[0398]

[0399] Except for replacing the starting materials with 1098-A and 1098-B and replacing potassium tetrachloroplatinate with zinc acetate, the synthesis was identical to that in Example 1. LC MS: M / Z 823.23 (M+). Overall yield: 32%; HPLC purity: 99.9%.

[0400] 1H NMR(400MHz,DMSO-d6)δ2.85(s,6H),3.59–3.76(m,4H),6.94–7.06(m,2H),7.20–7.53(m,15H),7.5 6–7.66(m,2H),7.70(d,1H),7.78(m,2H),7.86–7.94(m,2H),8.19(m,1H),8.66(m,1H),8.73(d,1H).

[0401] Device Example 1: Fabrication of Organic Electroluminescent Devices

[0402]

[0403] The basic structural model of the organic optoelectronic device of the present invention is: ITO / HAT-CN (10nm) / TAPC (40nm) / TCTA (10nm) / EML:GD (compound 10 of the present invention) = 94:6 (40nm) / ETL (30nm) / LiF (1nm) / Al (80nm).

[0404] The method for manufacturing organic optoelectronic devices of the present invention:

[0405] (1) The transparent anodic indium tin oxide (ITO) 20 (10Ω / sq) glass substrate was ultrasonically cleaned with acetone, ethanol and distilled water in sequence, and then treated with ozone plasma for 15 minutes.

[0406] (2) After mounting the ITO substrate on the substrate holder of the vacuum vapor deposition equipment, control the system pressure at 10. -6 Next, HAT-CN with a thickness of 10 nm, TAPC with a thickness of 40 nm, and TCTA with a thickness of 10 nm are sequentially deposited onto the ITO substrate.

[0407] (3) A light-emitting layer (EML) with a thickness of 40 nm is deposited on the above TCTA, wherein the mass ratio of compound 10 of the present invention to EML is 6:94.

[0408] (4) An electron transport layer (ETL) material with a thickness of 30 nm is deposited on the above-mentioned light-emitting layer.

[0409] (5) A 1 nm thick LiF layer is deposited on the electron transport layer as an electron injection layer.

[0410] (6) Finally, an Al layer with a thickness of 80 nm is deposited on the electron injection layer as a cathode, and the device is encapsulated using a glass cover.

[0411] Device Examples 2-56

[0412] In addition to the formation of the luminescent layer, compounds 39, 54, 86, 114, 129, 162, 170, 178, 207, 215, 234, 257, 280, 306, 317, 334, 359, 380, 399, 412, 439, 457, 480, 501, 523, 537, 555, 581, 599, 615, and 639 were used respectively. Organic electroluminescent devices were fabricated using the same method as in Device Example 1, except that compounds 658, 679, 699, 720, 741, 760, 781, 796, 807, 840, 858, 878, 900, 915, 936, 960, 979, 999, 1020, 1031, 1049, 1066, 1088, and 1098 were used to replace compound 10.

[0413] Device Comparison Example 1

[0414] Except that compound 10 was replaced with compound Pt-ref when forming the light-emitting layer, the organic electroluminescent device was fabricated using the same method as in Device Example 1.

[0415] The operating voltage and efficiency of the organic electroluminescent devices prepared above were calculated using a computer-controlled Keithley 2400 testing system. The device lifetime under dark conditions was obtained using a Polaronix (McScience Co.) lifetime measurement system equipped with a power supply and photodiodes as detection units. Each set of device examples and Device Comparative Example 1 were produced and tested in the same batch, as shown in Table 1.

[0416] Table 1 Test results of Device Examples 1-56 and Device Comparative Example 1

[0417]

[0418]

[0419]

[0420] According to the results in Table 1, when used as the light-emitting layer of a light-emitting device, the compounds used in Device Examples 1 to 56 all showed improved luminous efficiency (up to 29%) and increased lifetime by more than 40% compared to the devices formed by the compounds used in Device Comparative Example 1.

[0421] Accordingly, the device structures in the above embodiments and comparative examples are identical except for the light-emitting layer. Based on the device performance of Pt-ref, the current efficiency of the device containing the compound of the present invention is significantly improved, and its lifetime is also improved.

[0422] The above description is only a preferred embodiment of the present invention, but the scope of protection of the present invention is not limited thereto. Any equivalent substitutions or modifications made by those skilled in the art within the scope of the technology disclosed in the present invention, based on the technical solution and inventive concept of the present invention, should be covered within the scope of protection of the present invention.

Claims

1. A compound having the chemical structure shown in formula XXVII: ； (XXVII) In formula (XXⅦ): M is selected from Pt, Pd, Zn, or Cu; L5-L7 are independently selected from single bonds; X5 is selected from O and NR. 27 ; R 27 Each is independently selected from substituted or unsubstituted phenyl groups, and the substituents are tert-butyl or phenyl. A22, B22, C22, and D22 are each independently selected from the following substituted or unsubstituted groups: The substituent is tert-butyl, phenyl, or deuterated phenyl, or a cyclic group as shown below; and at least one of A22 and D22 is selected from the following cyclic groups. in, The atom on the phenyl group in the cyclic group is bonded to the adjacent group in formula (XXⅦ).

2. A compound, characterized in that, The compound is selected from one or more of the following chemical structures: 。 3. A compound, said compound being selected from one or more of the following chemical structures: 。 4. An organic layer comprising the compound as described in any one of claims 1 to 3.

5. The use of the compound as described in any one of claims 1 to 3 and / or the organic layer as described in claim 4 in organic optoelectronic devices.

6. An organic optoelectronic device comprising a first electrode, a second electrode, and an organic layer as described in claim 5, wherein, The organic layer is a light-emitting layer.

7. The organic optoelectronic device as described in claim 6, characterized in that, The light-emitting layer contains one or more compounds as described in claims 1 to 3.

8. The organic optoelectronic device as described in claim 6, characterized in that, The organic optoelectronic devices include organic photovoltaic devices, organic light-emitting devices, organic solar cells, electronic paper, organic photoreceptors, and organic thin-film transistors.

9. A display or lighting device comprising the organic optoelectronic device as described in any one of claims 7 to 8.

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