Organic compound and organic electroluminescent device

By introducing cycloalkyl and phenyl substituting structures into trianyl triarylamine compounds, the problem of insufficient efficiency and lifetime of electronic barrier layer materials in existing OLED devices is solved, and higher luminescence efficiency and longer service life are achieved.

CN116640065BActive Publication Date: 2025-05-02SHANGHAI QUADRISTAR ELECTRONIC TECH CO LTD
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Patent Information

Application Number
CN202310611125.7
Authority / Receiving Office
CN · China
Patent Type
Patents(China)
Current Assignee / Owner
Filing Date
2023-05-26
Publication Date
2025-05-02
Estimated Expiration
2043-05-26

AI Technical Summary

Technical Problem

In the prior art, the electronic barrier layer materials of OLED devices have not yet fully met the display field's demand for high efficiency and long service life.

Method used

A triarylamine-based triarylamine compound is provided, which enhances molecular solubility and stability by introducing a substituted structure of cycloalkyl and phenyl on the tribyl fragment, and increases the stacking distance between molecules through the non-planar spatial configuration of the cycloalkyl group to form a uniform amorphous film.

Benefits of technology

It improves the luminous efficiency and service life of OLED devices, while reducing the sublimation temperature of molecules and increasing the glass transition temperature to ensure the stability of the film under high temperature conditions.

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Abstract

The present invention relates to the field of organic electroluminescent materials, and in particular to an organic compound and an organic electroluminescent device. The organic compound has a chemical structure as shown in formula (1): The organic compound provided by the present invention has a stable molecular structure, a high triplet energy level and excellent hole transport properties and electron blocking properties, and is applied to the organic layer of an OLED device, especially the electron blocking layer, to effectively improve the luminous efficiency and service life of the device.
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Description

Technical Field

[0001] The present invention relates to the field of organic electroluminescent materials, and in particular to an organic compound and an organic electroluminescent device. Background Art

[0002] Organic electroluminescent devices (OLEDs) are a type of self-luminous electronic components that convert electrical energy into light energy. Their advantages are that they can provide high contrast, wide viewing angle and fast response speed, and can be prepared into bendable or rollable displays on flexible substrates, thus attracting widespread attention from academia and industry.

[0003] OLED devices are mainly composed of three parts: anode, cathode, and organic layer between anode and cathode. Among them, the electron-blocking layer has the function of suppressing reverse current and assisting hole transmission, while also having the function of resisting high-energy excitons, which can effectively improve the luminous efficiency and service life of the device, so it is very important.

[0004] Triphenylene is a condensed aromatic hydrocarbon formed by the condensation of four benzene rings, which has good planarity, high aromaticity and conjugation, and is conducive to the transport of carriers. When a triphenylene fragment, especially an aryl-substituted triphenylene fragment, is introduced into a triarylamine system, the resulting compound not only has good hole mobility, but also has a high triplet energy level, and is suitable for electron blocking layer materials. For example, application publication number CN 110606808 A discloses 3-aryl-1-diarylamine-substituted triphenylene and 4-aryl-2-diarylamine-substituted triphenylene, which are used in the electron blocking layer of OLED devices to achieve improved efficiency and service life. In addition, application publication numbers CN 112020502 A and KR 102015033074 A also disclose triarylamine compounds containing triphenylene substituted with aryl groups at different positions.

[0005] Although there have been a large number of related studies and public reports, it is still necessary to further develop high-performance electron blocking layer materials to meet the display field's demand for high efficiency and long service life of OLED devices. Summary of the invention

[0006] In view of the above-mentioned shortcomings of the prior art, an object of the present invention is to provide an organic compound and an organic electroluminescent device comprising the same, so as to solve the problems in the prior art.

[0007] To achieve the above-mentioned and other related purposes, the present invention provides an organic compound having a chemical structure as shown in formula (1):

[0008]

[0009] in,

[0010] A1~A 12 are the same or different and are each independently selected from hydrogen, deuterium, tritium, a halogen group, a cyano group, a straight-chain or branched alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, a trialkylsilyl group having 3 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a group represented by formula (2), or a group represented by formula (3);

[0011] And meet the conditions: A1~A 12 Among them, at least one is selected from the group represented by formula (2), and at least one is selected from the group represented by formula (3);

[0012] In formula (2), R is selected from hydrogen, deuterium, methyl or deuterated methyl; n is selected from 1 or 2;

[0013] Among G1 to G4, there is only one bonding site, which is the same as A1 to A 12 The rest are the same or different and are independently selected from hydrogen, deuterium, a halogen group, a straight or branched alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 20 carbon atoms;

[0014] In formula (3), L0, L1, and L2 are the same or different and are each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 40 carbon atoms, and a substituted or unsubstituted heteroarylene group having 2 to 40 carbon atoms;

[0015] Ar1 and Ar2 are the same or different and are each independently selected from a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms, or a group represented by formula (2).

[0016] Another aspect of the present invention provides an organic electroluminescent material, which comprises the organic compound of the present invention.

[0017] Another aspect of the present invention provides an organic compound for use as a functional material in an organic electronic device, wherein the organic electronic device includes an organic electroluminescent device, an organic thin film transistor, an organic solar cell, an organic-inorganic hybrid solar cell, an optical sensor, a radio frequency identification tag or an electronic paper.

[0018] Another aspect of the present invention provides an organic electroluminescent device, comprising a first electrode, a second electrode and one or more light-emitting functional layers located between the first electrode and the second electrode, wherein the light-emitting functional layer contains the compound described in the present invention. Further, the light-emitting functional layer comprises a hole transport region, a light-emitting layer, and an electron transport region, wherein the hole transport region is formed on the anode layer, the cathode layer is formed on the electron transport region, and the light-emitting layer is between the hole transport region and the electron transport region; wherein the compound described in the first aspect of the present invention is contained in the hole transport region and / or the electron transport region and / or the light-emitting layer.

[0019] The present invention provides a triphenylene-based triarylamine compound, in which a cycloalkylphenyl substitution structure is introduced into the triphenylene fragment. Compared with the prior art, the present invention has the following effects: on the one hand, the molecular solubility is improved, which is beneficial to its synthesis and purification, and the development of OLED device technology based on solution processing; on the other hand, the cycloalkyl group has a non-planar spatial configuration, which increases the stacking distance between molecules to a certain extent, and the molecular sublimation temperature is reduced while the glass transition temperature is increased. It is more inclined to form a uniform amorphous film during the film forming process, and the morphology of the film is not easy to produce defects when the device is operated for a long time and the temperature is increased; thirdly, the cycloalkylphenylphenyl group can replace the more reactive hydrogen atoms on the triphenylene, and the CH bond can form n-π conjugation, which is beneficial to improve the stability of the molecule.

[0020] In summary, the organic compound provided by the present invention has a stable molecular structure, a high triplet energy level and excellent hole transport properties and electron blocking properties. It is applied to the organic layer of OLED devices, especially the electron blocking layer, and can effectively improve the luminous efficiency and service life of the device. BRIEF DESCRIPTION OF THE DRAWINGS

[0021] Figure 1 Schematic diagram of the structure of the organic electroluminescent device in the embodiment.

[0022] In the figure:

[0023] 101 Base

[0024] 102 first electrode

[0025] 103 Hole injection layer

[0026] 104 Hole transport layer

[0027] 105 Electron blocking layer

[0028] 106 Luminescent Layer

[0029] 107 Hole blocking layer

[0030] 108 Electron transport layer

[0031] 109 second electrode DETAILED DESCRIPTION

[0032] Hereinafter, the present disclosure will be described in detail. However, the following description is intended to explain the present invention and is not intended to limit the scope of the present invention in any way.

[0033] The present disclosure relates to an organic compound represented by the above formula (1), an organic electroluminescent material including the organic compound, and an organic electroluminescent device including the organic electroluminescent material.

[0034] The term "organic compound" in the present disclosure means a compound that can be used in an organic electroluminescent device and can be contained in any layer constituting the organic electroluminescent device as necessary.

[0035] The term "organic electroluminescent material" in the present disclosure means a material that can be used in an organic electroluminescent device and can contain at least one compound. If necessary, the organic electroluminescent material can be contained in any layer constituting the organic electroluminescent device. For example, the organic electroluminescent material can be a hole injection material, a hole transport material, a hole auxiliary material, a luminescence auxiliary material, an electron blocking material, a luminescent material (including a host material and a dopant material), an electron buffer material, a hole blocking material, an electron transport material, or an electron injection material, etc.

[0036] In the present disclosure, the term "a linear or branched alkyl group having 1 to 20 carbon atoms" means a linear or branched alkyl group having 1 to 20 carbon atoms constituting the chain, wherein the number of carbon atoms is preferably 1 to 15, the number of carbon atoms is further preferably 1 to 10, and more preferably 1 to 6. The above-mentioned alkyl group may include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, sec-butyl, and the like.

[0037] In the present disclosure, the term "cycloalkyl group having 3 to 20 carbon atoms" means a mono- or polycyclic hydrocarbon having 3 to 20 ring skeleton carbon atoms, wherein the number of carbon atoms is preferably 3 to 15, the number of carbon atoms is preferably 3 to 10, and more preferably 3 to 7. The above-mentioned cycloalkyl group may include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopentylmethyl, cyclohexylmethyl and the like.

[0038] In the present disclosure, the term "trialkylsilyl having 3 to 20 carbon atoms" includes 3 branched and / or linear alkyl groups connected to and through silicon atoms. Among them, the number of carbon atoms is preferably 3 to 15, the number of carbon atoms is further preferably 3 to 10, and more preferably 3 to 7. Such as trimethylsilyl, triethylsilyl and tert-butyldimethylsilyl.

[0039] In the present disclosure, the term "alkoxy" refers to -O(alkyl). Optionally, the alkyl portion of the alkoxy group may contain 1-20 carbon atoms, 1-15 carbon atoms, 1-10 carbon atoms, 1-6 carbon atoms, or 1-4 carbon atoms, etc. Alkoxy groups, for example, may include, but are not limited to, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, etc.

[0040] In the present disclosure, the term "substituted or unsubstituted (ene)aryl group having 6 to 50 carbon atoms" means a monocyclic or condensed ring group derived from an aromatic hydrocarbon having 6 to 50 ring skeleton carbon atoms, wherein the number of ring skeleton carbon atoms is preferably 6 to 40, 6 to 30, 6 to 20, more preferably 6 to 15, and may be partially saturated and may contain a spiro structure. Examples of aryl groups specifically include phenyl, biphenyl, terphenyl, quaterphenyl, naphthyl, binaphthyl, phenylnaphthyl, naphthylphenyl, fluorenyl, phenylfluorenyl, dimethylfluorenyl, diphenylfluorenyl, benzofluorenyl, diphenylbenzofluorenyl, dibenzofluorenyl, phenanthryl, triphenylenyl, phenylphenanthryl, anthracenyl, benzanthryl, indenyl, triphenylene, pyrenyl, naphthacene, peryl, mesityl, benzo, naphthacene, fluoranthenyl, benzofluoranthenyl, tolyl, xylyl, mesityl, cumenyl, spiro[fluorene-fluorenyl]yl, spiro[fluorene-benzofluorenyl]yl, azulenyl, tetramethyl-dihydrophenanthryl and the like. More specifically, the aryl group may be o-tolyl, m-tolyl, p-tolyl, 2,3-xylyl, 3,4-xylyl, 2,5-xylyl, mesityl, o-cumyl, m-cumyl, p-cumyl, p-tert-butylphenyl, p-(2-phenylpropyl)phenyl, 4'-methylbiphenyl, 4"-tert-butyl-p-terphenyl-4-yl, o-biphenyl, m-biphenyl, p-biphenyl, o-terphenyl, m-terphenyl-4-yl, m-terphenyl-3- yl, m-terphenyl-2-yl, p-terphenyl-4-yl, p-terphenyl-3-yl, p-terphenyl-2-yl, m-quaterphenyl, 1-naphthyl, 2-naphthyl, 1-fluorenyl, 2-fluorenyl, 3-fluorenyl, 4-fluorenyl, 9-fluorenyl, 9,9-dimethyl-1-fluorenyl, 9,9-dimethyl-2-fluorenyl, 9,9-dimethyl-3-fluorenyl, 9,9-dimethyl-4-fluorenyl, 9,9-diphenyl-1-fluorenyl, 9,9-diphenyl-2-fluorenyl, 9,9-diphenyl -3-fluorenyl, 9,9-diphenyl-4-fluorenyl, 1-anthryl, 2-anthryl, 9-anthryl, 1-phenanthrenyl, 2-phenanthrenyl, 3-phenanthrenyl, 4-phenanthrenyl, 9-phenanthrenyl, 1-yl, 2-yl, 3-yl, 4-yl, 5-yl, 6-yl, benzo[c]phenanthrenyl, benzo[g]yl, 1-triphenylene, 2-triphenylene, 3-triphenylene, 4-triphenylene, 3-fluoranthene, 4-fluoranthene, 8-fluoranthene, 9-fluoranthene, benzofluoranthene, 11,11-dimethyl-1-phenyl 11,11-dimethyl-2-benzo[a]fluorenyl, 11,11-dimethyl-3-benzo[a]fluorenyl, 11,11-dimethyl-4-benzo[a]fluorenyl, 11,11-dimethyl-5-benzo[a]fluorenyl, 11,11-dimethyl-6-benzo[a]fluorenyl, 11,11-dimethyl-7-benzo[a]fluorenyl, 11,11-dimethyl-8-benzo[a]fluorenyl, 11,11-dimethyl-9-benzo[a]fluorenyl, 11,11-dimethyl-12-benzo[a]fluorenyl, 11,11-dimethyl-2-benzo[a]fluorenyl, 11,11-dimethyl-3-benzo[a]fluorenyl, 11,11-dimethyl-4-benzo[a]fluorenyl, 11,11-dimethyl-5-benzo[a]fluorenyl, 11,11-dimethyl-6-benzo[a]fluorenyl, 11,11-dimethyl-7-benzo[a]fluorenyl, 11,11-dimethyl-8-benzo[a]fluorenyl, 11,11-dimethyl-9-benzo[a]fluorenyl, 11,11-dimethyl-11-dimethyl-10-benzo[a]fluorenyl, 11,11-dimethyl-1-benzo[b]fluorenyl, 11,11-dimethyl-2-benzo[b]fluorenyl, 11,11-dimethyl-3-benzo[b]fluorenyl, 11,11-dimethyl-4-benzo[b]fluorenyl, 11,11-dimethyl-5-benzo[b]fluorenyl, 11,11 -dimethyl-6-benzo[b]fluorenyl, 11,11-dimethyl-7-benzo[b]fluorenyl, 11,11-dimethyl-8-benzo[b]fluorenyl, 11,11-dimethyl-9-benzo[b]fluorenyl, 11,11-dimethyl-10-benzo[b]fluorenyl, 11,11-dimethyl-1-benzo[c]fluorenyl, 11,11-dimethyl- methyl-2-benzo[c]fluorenyl, 11,11-dimethyl-3-benzo[c]fluorenyl, 11,11-dimethyl-4-benzo[c]fluorenyl, 11,11-dimethyl-5-benzo[c]fluorenyl, 11,11-dimethyl-6-benzo[c]fluorenyl, 11,11-dimethyl-7-benzo[c]fluorenyl, 11,11-dimethyl- 8-benzo[c]fluorenyl, 11,11-dimethyl-9-benzo[c]fluorenyl, 11,11-dimethyl-10-benzo[c]fluorenyl, 11,11-diphenyl-1-benzo[a]fluorenyl, 11,11-diphenyl-2-benzo[a]fluorenyl, 11,11-diphenyl-3-benzo[a]fluorenyl, 11,11-diphenyl-4- Benzo[a]fluorenyl, 11,11-diphenyl-5-benzo[a]fluorenyl, 11,11-diphenyl-6-benzo[a]fluorenyl, 11,11-diphenyl-7-benzo[a]fluorenyl, 11,11-diphenyl-8-benzo[a]fluorenyl, 11,11-diphenyl-9-benzo[a]fluorenyl, 11,11-diphenyl-10-benzo[a]fluorenyl [a] fluorenyl, 11,11-diphenyl-1-benzo[b] fluorenyl, 11,11-diphenyl-2-benzo[b] fluorenyl, 11,11-diphenyl-3-benzo[b] fluorenyl, 11,11-diphenyl-4-benzo[b] fluorenyl, 11,11-diphenyl-5-benzo[b] fluorenyl, 11,11-diphenyl-6-benzo[b] Fluorenyl, 11,11-diphenyl-7-benzo[b]fluorenyl, 11,11-diphenyl-8-benzo[b]fluorenyl, 11,11-diphenyl-9-benzo[b]fluorenyl, 11,11-diphenyl-10-benzo[b]fluorenyl, 11,11-diphenyl-1-benzo[c]fluorenyl, 11,11-diphenyl-2-benzo[c]fluorenyl , 11,11-diphenyl-3-benzo[c]fluorenyl, 11,11-diphenyl-4-benzo[c]fluorenyl, 11,11-diphenyl-5-benzo[c]fluorenyl, 11,11-diphenyl-6-benzo[c]fluorenyl, 11,11-diphenyl-7-benzo[c]fluorenyl, 11,11-diphenyl-8-benzo[c]fluorenyl, 11,11-diphenyl-11-diphenyl-9-benzo[c]fluorenyl, 11,11-diphenyl-10-benzo[c]fluorenyl, 9,9,10,10-tetramethyl-9,10-dihydro-1-phenanthryl, 9,9,10,10-tetramethyl-9,10-dihydro-2-phenanthryl, 9,9,10,10-tetramethyl-9,10-dihydro-3-phenanthryl, 9,9,10,10-tetramethyl-9,10-dihydro-4-phenanthryl, etc.

[0041] In the present disclosure, the term "substituted or unsubstituted (sub)heteroaryl having 2 to 50 carbon atoms" refers to an aryl group having a ring skeleton atom, wherein the ring skeleton atom includes at least one heteroatom selected from the group consisting of B, N, O, S, Si, P, Se and Ge, preferably at least one heteroatom selected from N, O and S, wherein the number of ring skeleton carbon atoms is preferably 2 to 40, 2 to 30, 2 to 25, 2 to 20. The number of heteroatoms in the heteroaryl group is preferably 1 to 4. The above heteroaryl group may be a monocyclic ring or a condensed ring condensed with at least one benzene ring; and may be partially saturated. In addition, herein, the above heteroaryl group may be a heteroaryl group formed by connecting at least one heteroaryl group or aryl group to a heteroaryl group via one or more single bonds. Examples of heteroaryl groups include monocyclic heteroaryl groups, including furanyl, thienyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetrazinyl, triazolyl, tetrazolyl, furazanyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, and the like, and fused ring heteroaryl groups, including benzofuranyl, benzothienyl, isobenzofuranyl, dibenzofuranyl, thiophene, dibenzothiophene, dibenzoselenophene, benzofuranoquinolyl, benzofuranoquinazolinyl, benzofurano naphthyridinyl, benzofuranopyrimidinyl, naphthyridinyl, benzothiophenoquinolyl, benzothiophenoquinazolinyl, benzothiophenonaphthyridinyl, benzothiophenopyrimidinyl, naphthyridinyl, pyrimidoindolyl, benzopyrimidoindolyl, benzofuranopyrazinyl, naphthyridinyl, pyrazinyl, benzothienopyrazinyl, naphthienopyrazinyl, pyrazinoindolyl, benzopyrazinoindolyl, benzimidazolyl, benzothiazolyl, benzisothiazolyl, benzisoxazolyl, benzoxazolyl, imidazopyridinyl, isoindolyl, indolyl, benzindolyl, indazolyl, benzothiadiazolyl, quinolyl, isoquinolyl, cinnolinyl, quinazolinyl, quinoxalinyl, carbazolyl, azacarbazolyl, benzocarbazolyl The heteroaryl group may be 1-pyrrolyl, 2-pyrrolyl, 3-pyrrolyl, 2-pyridyl, 3-pyridyl, 4-pyridyl, 2-pyrimidyl, 4-pyrimidyl, 5-pyrimidyl, 6-pyrimidyl, 1,2,3-triazine-4-yl, 1,2,4-triazine-3-yl, 1,3,5-triazine-2-yl, 1-imidazolyl, 2-imidazolyl, 1-pyrazolyl, 1-indolizidinyl, 2-indolizidinyl, 3-indolizidinyl, 5-indolizidinyl, 6-indolizidinyl, 7-indolizidinyl, 8-indolizidinyl, 2-imidazopyridinyl, 3-imidazopyridinyl, 5-imidazopyridinyl, 6-imidazopyridinyl yl, 7-imidazopyridinyl, 8-imidazopyridinyl, 1-indolyl, 2-indolyl, 3-indolyl, 4-indolyl, 5-indolyl, 6-indolyl, 7-indolyl, 1-isoindolyl, 2-isoindolyl, 3-isoindolyl, 4-isoindolyl, 5-isoindolyl, 6-isoindolyl, 7-isoindolyl, 2-furyl, 3-furyl, 2- benzofuranyl, 3-benzofuranyl, 4-benzofuranyl, 5-benzofuranyl, 6-benzofuranyl, 7-benzofuranyl, 1-isobenzofuranyl, 3-isobenzofuranyl, 4-isobenzofuranyl, 5-isobenzofuranyl, 6-isobenzofuranyl, 7-isobenzofuranyl, 2-quinolyl, 3-quinolyl, 4-quinolyl, 5-quinolyl, 6-quinolyl, 7-quinolyl, 8-quinolyl, 1-isoquinolyl, 3-isoquinolyl, 4-isoquinolyl, 5-isoquinolyl, 6-isoquinolyl, 7-isoquinolyl, 8-isoquinolyl, 2-quinoxalinyl, 5-quinoxalinyl, 6-quinoxalinyl, 1-carbazolyl, 2-carbazolyl, 3-carbazolyl, 4-carbazolyl, 9-carbazolyl, azacarbazolyl-1 -yl, azacarbazole-2-yl, azacarbazole-3-yl, azacarbazole-4-yl, azacarbazole-5-yl, azacarbazole-6-yl, azacarbazole-7-yl, azacarbazole-8-yl, azacarbazole-9-yl, 1-phenanthridinyl, 2-phenanthridinyl, 3-phenanthridinyl, 4-phenanthridinyl, 6-phenanthridinyl, 7-phenanthridinyl, 8-phenanthridinyl, 9-phenanthridin ... 0-phenanthridinyl, 1-acridinyl, 2-acridinyl, 3-acridinyl, 4-acridinyl, 9-acridinyl, 2-oxazolyl, 4-oxazolyl, 5-oxazolyl, 2-oxadiazolyl, 5-oxadiazolyl, 3-furazanyl, 2-thienyl, 3-thienyl, 2-methylpyrrol-1-yl, 2-methylpyrrol-3-yl, 2-methylpyrrol-4-yl, 2-methylpyrrol -5-yl, 3-methylpyrrol-1-yl, 3-methylpyrrol-2-yl, 3-methylpyrrol-4-yl, 3-methylpyrrol-5-yl, 2-tert-butylpyrrol-4-yl, 3-(2-phenylpropyl)pyrrol-1-yl, 2-methyl-1-indolyl, 4-methyl-1-indolyl, 2-methyl-3-indolyl, 4-methyl-3-indolyl, 2-tert-butyl-1-indolyl, 4-tert-butyl-1-indolyl, 2-tert-butyl-3-indolyl, 4-tert-butyl-3-indolyl, 1-dibenzofuranyl, 2-dibenzofuranyl, 3-dibenzofuranyl, 4-dibenzofuranyl, 1-dibenzothiophenyl, 2-dibenzothiophenyl, 3-dibenzothiophenyl, 4-dibenzothiophenyl, 1-naphtho-[1,2-b]-benzofuranyl, 2-naphtho-[1,2-b]-benzofuranyl, 3-naphtho-[1,2-b]-benzofuranyl, 4-naphtho-[1,2-b]-benzofuranyl, 5-naphtho-[1,2-b]-benzofuranyl, 6-naphtho-[1,2-b]-benzofuranyl, 7-naphtho-[1,2-b]-benzofuranyl , 8-naphtho-[1,2-b]-benzofuranyl, 9-naphtho-[1,2-b]-benzofuranyl, 10-naphtho-[1,2-b]-benzofuranyl, 1-naphtho-[2,3-b]-benzofuranyl, 2-naphtho-[2,3-b]-benzofuranyl, 3-naphtho-[2,3-b]-benzofuranyl, 4-naphtho-[2, 3-b]-benzofuranyl, 5-naphtho-[2,3-b]-benzofuranyl, 6-naphtho-[2,3-b]-benzofuranyl, 7-naphtho-[2,3-b]-benzofuranyl, 8-naphtho-[2,3-b]-benzofuranyl, 9-naphtho-[2,3-b]-benzofuranyl, 10-naphtho-[2,3-b]-benzofuranyl 1-naphtho-[2,1-b]-benzofuranyl, 2-naphtho-[2,1-b]-benzofuranyl, 3-naphtho-[2,1-b]-benzofuranyl, 4-naphtho-[2,1-b]-benzofuranyl, 5-naphtho-[2,1-b]-benzofuranyl, 6-naphtho-[2,1-b]-benzofuranyl, 7-naphtho-[2,1-b]-benzofuranyl, 1-b]-benzofuranyl, 8-naphtho-[2,1-b]-benzofuranyl, 9-naphtho-[2,1-b]-benzofuranyl, 10-naphtho-[2,1-b]-benzofuranyl, 1-naphtho-[1,2-b]-benzothiophene, 2-naphtho-[1,2-b]-benzothiophene, 3-naphtho-[1,2-b]-benzothiophene 4-naphtho-[1,2-b]-benzothiophenyl, 5-naphtho-[1,2-b]-benzothiophenyl, 6-naphtho-[1,2-b]-benzothiophenyl, 7-naphtho-[1,2-b]-benzothiophenyl, 8-naphtho-[1,2-b]-benzothiophenyl, 9-naphtho-[1,2-b]-benzothiophenyl, 10-naphtho-[1 ,2-b]-benzothiophene, 1-naphtho-[2,3-b]-benzothiophene, 2-naphtho-[2,3-b]-benzothiophene, 3-naphtho-[2,3-b]-benzothiophene, 4-naphtho-[2,3-b]-benzothiophene, 5-naphtho-[2,3-b]-benzothiophene, 1-naphtho-[2,1-b]-benzothiophene 1-b-benzothiophene, 2-naphtho-[2,1-b]-benzothiophene, 3-naphtho-[2,1-b]-benzothiophene, 4-naphtho-[2,1-b]-benzothiophene, 5-naphtho-[2,1-b]-benzothiophene, 6-naphtho-[2,1-b]-benzothiophene, 7-naphtho-[2,1-b]-benzothiophene, 8-naphtho-[2,1-b]-benzothiophene,1-b]-benzothiophenyl, 9-naphtho-[2,1-b]-benzothiophenyl, 10-naphtho-[2,1-b]-benzothiophenyl, 2-benzofurano[3,2-d]pyrimidinyl, 6-benzofurano[3,2-d]pyrimidinyl, 7-benzofurano[3,2-d]pyrimidinyl, 8-benzofurano[3,2-d]pyrimidinyl, 9-benzofurano[3,2-d]pyrimidinyl, 2-benzothio[3,2-d]pyrimidinyl, 6-benzothio[3,2-d]pyrimidinyl, 7-benzothio[3,2-d]pyrimidinyl, 8-benzothio[3,2-d]pyrimidinyl, 9-benzothio[3,2-d]pyrimidinyl, 2-benzofurano[3,2-d]pyrimidinyl, , 6-benzofurano[3,2-d]pyrazinyl, 7-benzofurano[3,2-d]pyrazinyl, 8-benzofurano[3,2-d]pyrazinyl, 9-benzofurano[3,2-d]pyrazinyl, 2-benzothio[3,2-d]pyrazinyl, 6-benzothio[3,2-d]pyrazinyl, 7-benzothio[3,2-d]pyrazinyl oxazine, 8-benzothio[3,2-d]pyrazine, 9-benzothio[3,2-d]pyrazine, 1-silicon fluorenyl, 2-silicon fluorenyl, 3-silicon fluorenyl, 4-silicon fluorenyl, 1-germanium fluorenyl, 2-germanium fluorenyl, 3-germanium fluorenyl, 4-germanium fluorenyl, 1-dibenzoselenophene, 2-dibenzoselenophene, 3-dibenzoselenophene, 4-dibenzoselenophene, etc.

[0042] In the present disclosure, the term "halogen" includes F, Cl, Br and I.

[0043] In the present disclosure, the term "bonded to each other to form a cycloalkyl group having 5 to 12 carbon atoms, or bonded to form a substituted or unsubstituted aryl or heteroaryl group having 12 to 30 carbon atoms" takes R3 and R4 bonded to each other to form a cycloalkyl group having 5 carbon atoms as an example, then That is Y, then combined with In the formula, Ar1 is Other explanations are the same here.

[0044] In addition, the term "substituted" in the expression "substituted or unsubstituted" means that a hydrogen atom in a functional group is replaced by another atom or functional group (i.e., a substituent). For example, the substituent is deuterium, a halogen group, a cyano group, a straight or branched alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, a trialkylsilyl group having 3 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 20 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 20 carbon atoms. The substituent substituted in the substituted or unsubstituted heteroaryl group having 2 to 20 carbon atoms and the substituted or unsubstituted aryl group having 6 to 20 carbon atoms is selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 10 carbon atoms, and an alkoxy group having 1 to 10 carbon atoms.

[0045] Hereinafter, the organic compound according to the present invention will be described.

[0046] The organic compound has a chemical structure as shown in formula (1):

[0047]

[0048] in,

[0049] A1~A 12 are the same or different and are each independently selected from hydrogen, deuterium, tritium, a halogen group, a cyano group, a straight-chain or branched alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, a trialkylsilyl group having 3 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a group represented by formula (2), or a group represented by formula (3);

[0050] And meet the conditions: A1~A 12 Among them, at least one is selected from the group represented by formula (2), and at least one is selected from the group represented by formula (3);

[0051] In formula (2), R is selected from hydrogen, deuterium, methyl or deuterated methyl; n is selected from 1 or 2;

[0052] Among G1 to G4, there is only one bonding site, which is the same as A1 to A 12 The rest are the same or different and are independently selected from hydrogen, deuterium, a halogen group, a straight or branched alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 20 carbon atoms.

[0053] In formula (3), L0, L1, and L2 are the same or different and are each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 40 carbon atoms, and a substituted or unsubstituted heteroarylene group having 2 to 40 carbon atoms;

[0054] Ar1 and Ar2 are the same or different and are each independently selected from a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms, or a group represented by formula (2);

[0055] * is the bonding site.

[0056] In this application, A1~A 12In the above, the substituent in the substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms or the substituted or unsubstituted aryl group having 6 to 30 carbon atoms is selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 10 carbon atoms, or an alkoxy group having 1 to 10 carbon atoms.

[0057] In the present application, the "substituted" substituents in L0, L1, L2, Ar1 and Ar2 are the same or different and are each independently selected from deuterium, a halogen group, a cyano group, a straight or branched alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, a trialkylsilyl group having 3 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, a heteroaryl group having 2 to 20 carbon atoms, or an aryl group having 6 to 20 carbon atoms.

[0058] In some embodiments, A1-A 12 are the same or different and are each independently selected from hydrogen.

[0059] In some embodiments, A1-A 12 are the same or different and are each independently selected from deuterium.

[0060] In some embodiments, A1-A 12 The same or different, each independently selected from a halogen group, such as fluorine, chlorine, bromine, iodine and the like.

[0061] In some embodiments, A1-A 12 are the same or different and are each independently selected from cyano.

[0062] In some embodiments, A1-A 12 are the same or different and are independently selected from a linear or branched alkyl group having 1 to 20 carbon atoms. 12 The same or different, each independently selected from a linear or branched alkyl group having 1 to 15, 1 to 10, 1 to 8, or 1 to 6 carbon atoms. Further, the alkyl group may include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, sec-butyl, etc.

[0063] In some embodiments, A1-A 12 are the same or different and are independently selected from a cycloalkyl group having 3 to 20 carbon atoms. 12 The same or different, each independently selected from a cycloalkyl group having 3 to 15, 3 to 10, 3 to 8, or 3 to 6 carbon atoms. Further, the cycloalkyl group may include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopentylmethyl, cyclohexylmethyl, and the like.

[0064] In some embodiments, A1-A 12are the same or different and are independently selected from trialkylsilyl groups having 3 to 20 carbon atoms. 12 The same or different groups are each independently selected from a trialkylsilyl group having 3 to 15, 3 to 10, 3 to 8, or 3 to 6 carbon atoms.

[0065] In some embodiments, A1-A 12 are the same or different and are independently selected from an alkoxy group having 1 to 20 carbon atoms. 12 The same or different, each independently selected from carbon atoms having 1 to 15, 1 to 10, 1 to 8, or 1 to 6. Further, alkoxy groups may include, but are not limited to, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, and the like.

[0066] In some embodiments, A1-A 12 are the same or different and are each independently selected from a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms.

[0067] In some embodiments, A1-A 12 are the same or different and are each independently selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

[0068] In some embodiments, A1-A 12 The same or different, each independently selected from the group represented by formula (2)

[0069] In some embodiments, in formula (2), R is selected from hydrogen.

[0070] In some embodiments, in formula (2), R is selected from deuterium.

[0071] In some embodiments, in formula (2), R is selected from methyl.

[0072] In some embodiments, in formula (2), R is selected from deuterated methyl.

[0073] In some embodiments, in formula (2), n is selected from 1, or 2;

[0074] In some embodiments, in formula (2), among G1 to G4, there is only one bonding site, and it is the same as A1 to A4 in formula (1). 12The rest are the same or different from each other, and are independently selected from hydrogen, deuterium, halogen groups, straight or branched alkyl groups with 1 to 10 carbon atoms, cycloalkyl groups with 3 to 10 carbon atoms, alkoxy groups with 1 to 10 carbon atoms, and aromatic groups with 6 to 20 carbon atoms. Optionally, the rest are the same or different from each other, and are independently selected from hydrogen, deuterium, fluorine, chlorine, bromine, iodine, straight or branched alkyl groups with 1 to 6 carbon atoms, cycloalkyl groups with 3 to 6 carbon atoms, alkoxy groups with 1 to 6 carbon atoms, and aromatic groups with 6 to 12 carbon atoms. Preferably, G1 to G4 have and only have one bonding site, and the rest are independently selected from hydrogen, deuterium, alkyl groups with 1 to 4 carbon atoms, or phenyl groups.

[0075] In some embodiments, A1-A 12 The same or different, each independently selected from the group represented by formula (3)

[0076] In some embodiments, in formula (3), Ar1 and Ar2 are the same or different and are independently selected from substituted or unsubstituted aryl groups having 6 to 50 carbon atoms. In specific embodiments, Ar1 and Ar2 are independently selected from substituted or unsubstituted aryl groups having 6 to 40, 6 to 30, 6 to 20, or 6 to 15 carbon atoms.

[0077] In some embodiments, in formula (3), Ar1 and Ar2 are the same or different and are independently selected from substituted or unsubstituted heteroaryl groups having 2 to 50 carbon atoms. In specific embodiments, Ar1 and Ar2 are independently selected from substituted or unsubstituted heteroaryl groups having 2 to 40, 2 to 30, 2 to 20, or 2 to 15 carbon atoms.

[0078] In some embodiments, in formula (3), Ar1 and Ar2 are the same or different and are independently selected from the group represented by formula (2). Formula (2) has the same definition as above.

[0079] In some embodiments, in formula (3), Ar1 and Ar2 are the same or different from each other and are independently selected from any one of the following groups:

[0080]

[0081] Wherein, each occurrence of X is independently selected from N, CH, CR1 or C *a ; and the condition is met: there is only one X selected from C *a , *a is the bonding site;

[0082] R1 is selected from deuterium, a halogen group, a cyano group, a straight or branched alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, a trialkylsilyl group having 3 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 20 carbon atoms, and a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, wherein the aforementioned "substituted" substituent is selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, and a phenyl group. Optionally, R1 is selected from deuterium, fluorine, chlorine, bromine, iodine, cyano, straight or branched alkyl with 1 to 6 carbon atoms, cycloalkyl with 3 to 6 carbon atoms, trialkylsilyl with 3 to 6 carbon atoms, alkoxy with 1 to 6 carbon atoms, substituted or unsubstituted heteroaryl with 2 to 15 carbon atoms, substituted or unsubstituted aryl with 6 to 12 carbon atoms, wherein the aforementioned "substituted" substituent is selected from deuterium, fluorine, chlorine, bromine, iodine, cyano, alkyl with 1 to 6 carbon atoms, alkoxy with 1 to 6 carbon atoms, etc. In a specific embodiment, the unsubstituted aryl with 6 to 20 carbon atoms is such as phenyl, naphthyl, biphenyl, etc., and the substituted aryl with 6 to 20 carbon atoms can also be substituted by an alkyl group, such as methylphenyl, tert-butylphenyl, etc.

[0083] Y is selected from O, S, NR2, CR3R4, or SiR5R6; R2~R6 are each independently selected from a straight chain or branched alkyl group having 1 to 12 carbon atoms, a cycloalkyl group having 3 to 12 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 20 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, and the substituents in the heteroaryl or aryl group are selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 10 carbon atoms, and an alkoxy group having 1 to 10 carbon atoms; or, R3 and R4 are bonded to each other to form a cycloalkyl group having 5 to 12 carbon atoms, or are bonded to form a substituted or unsubstituted aryl or heteroaryl group having 12 to 30 carbon atoms, and the "substituted" substituents are selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 10 carbon atoms, and an alkoxy group having 1 to 10 carbon atoms. Optionally, R2 to R6 are each independently selected from a straight chain or branched alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 15 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 12 carbon atoms, and the substituents in the heteroaryl or aryl group are selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 5 carbon atoms, or an alkoxy group having 1 to 10 carbon atoms; or, R3 and R4 are bonded to each other to form a cycloalkyl group having 5 to 8 carbon atoms, or are bonded to form a substituted or unsubstituted aryl or heteroaryl group having 12 to 20 carbon atoms, wherein the "substituted" substituents are selected from deuterium, fluorine, chlorine, bromine, iodine, cyano group, an alkyl group having 1 to 6 carbon atoms, or an alkoxy group having 1 to 6 carbon atoms. In a specific embodiment, the unsubstituted aryl group having 6 to 20 carbon atoms may be, for example, phenyl, naphthyl, biphenyl, etc., and the substituted aryl group having 6 to 20 carbon atoms may be substituted by an alkyl group, for example, methylphenyl, tert-butylphenyl, etc.

[0084] Ar1 and Ar2 are the same or different and are independently selected from any one of the following groups:

[0085]

[0086] In any of the above groups, any and only one carbon on the aromatic ring or heteroaromatic ring is a bonding site, and / or any hydrogen atom may be unsubstituted or substituted. When any hydrogen atom is substituted, it may be substituted by one of deuterium, fluorine, chlorine, bromine, cyano, methoxy, ethoxy, methyl, deuterated methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, phenyl, tolyl, tert-butylphenyl, biphenyl, naphthyl, pyridyl, fluorenyl, carbazolyl, dibenzofuranyl, and dibenzothiophenyl.

[0087] In some embodiments, in formula (3), L0, L1, and L2 are the same or different and are each independently selected from a single bond.

[0088] In some embodiments, in formula (3), L0, L1, and L2 are the same or different and are each independently selected from a substituted or unsubstituted arylene group having 6 to 40 carbon atoms. In specific embodiments, L0, L1, and L2 are each independently selected from a substituted or unsubstituted arylene group having 6 to 30, 6 to 20, or 6 to 15 carbon atoms.

[0089] In some embodiments, in formula (3), L0, L1, and L2 are the same or different and are each independently selected from a substituted or unsubstituted heteroarylene group having 2 to 40 carbon atoms. In specific embodiments, L0, L1, and L2 are each independently selected from a substituted or unsubstituted heteroarylene group having 2 to 30, 2 to 20, or 2 to 15 carbon atoms.

[0090] In some embodiments, L0, L1, and L2 are the same or different from each other, and are each independently selected from a single bond or the following group:

[0091]

[0092] Wherein, U is independently selected from N, CH, CR 7 or C *b , and satisfies that there are only two U selected from C *b , *b is the bonding site;

[0093] R7 is selected from deuterium, a halogen group, a cyano group, a straight or branched alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, a trialkylsilyl group having 3 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 20 carbon atoms, and a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, wherein the aforementioned "substituted" substituent is selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 10 carbon atoms, and an alkoxy group having 1 to 10 carbon atoms. Optionally, R7 is selected from deuterium, fluorine, chlorine, bromine, iodine, cyano, straight or branched alkyl with 1 to 6 carbon atoms, cycloalkyl with 3 to 6 carbon atoms, trialkylsilyl with 3 to 6 carbon atoms, alkoxy with 1 to 6 carbon atoms, substituted or unsubstituted heteroaryl with 2 to 15 carbon atoms, substituted or unsubstituted aryl with 6 to 12 carbon atoms, wherein the aforementioned "substituted" substituent is selected from deuterium, halogen group, cyano, alkyl with 1 to 10 carbon atoms, alkoxy with 1 to 10 carbon atoms, etc. In a specific embodiment, the unsubstituted aryl with 6 to 20 carbon atoms is such as phenyl, naphthyl, biphenyl, etc., and the substituted aryl with 6 to 20 carbon atoms can also be substituted by an alkyl group, such as methylphenyl, tert-butylphenyl, etc.

[0094] V is selected from O, S, NR8, CR9R 10 , or SiR 11 R12 ; R8~R 12 Each is independently selected from a straight chain or branched alkyl group having 1 to 12 carbon atoms, a cycloalkyl group having 3 to 12 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 20 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, wherein the substituent in the heteroaryl or aryl group is selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 10 carbon atoms, or an alkoxy group having 1 to 10 carbon atoms; or, R9, R 10 Bonded to each other to form a cycloalkyl group with 5 to 12 carbon atoms, or bonded to form a substituted or unsubstituted aryl or heteroaryl group with 12 to 30 carbon atoms, wherein the "substituted" substituent is selected from deuterium, a halogen group, a cyano group, an alkyl group with 1 to 10 carbon atoms, and an alkoxy group with 1 to 10 carbon atoms. Optionally, V is selected from O, S, NR8, CR9R 10 , or SiR 11 R 12 ; R8~R 12 Each is independently selected from a straight chain or branched alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 15 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 12 carbon atoms, wherein the substituent in the heteroaryl or aryl group is selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 10 carbon atoms, or an alkoxy group having 1 to 10 carbon atoms; or, R9, R 10 Bonded to each other to form a cycloalkyl group with 5 to 8 carbon atoms, or bonded to form a substituted or unsubstituted aryl or heteroaryl group with 12 to 15 carbon atoms, wherein the "substituted" substituent is selected from deuterium, a halogen group, a cyano group, an alkyl group with 1 to 6 carbon atoms, and an alkoxy group with 1 to 6 carbon atoms. In a specific embodiment, the unsubstituted aryl group with 6 to 20 carbon atoms is such as phenyl, naphthyl, biphenyl, etc., and the substituted aryl group with 6 to 20 carbon atoms can also be substituted by an alkyl group, such as methylphenyl, tert-butylphenyl, etc.

[0095] In some embodiments, L0, L1, and L2 are the same or different from each other, and are each independently selected from a single bond or the following group:

[0096]

[0097] In any of the above groups, any two and only two carbon atoms on the aromatic ring or heteroaromatic ring are bonding sites, or any hydrogen atom may be unsubstituted or substituted. When any hydrogen atom is substituted, it may be substituted by one of deuterium, fluorine, chlorine, bromine, cyano, methoxy, ethoxy, methyl, deuterated methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, phenyl, tolyl, tert-butylphenyl, biphenyl, naphthyl, pyridyl, fluorenyl, carbazolyl, dibenzofuranyl, and dibenzothiophenyl.

[0098] According to one embodiment, the chemical formula (1) has a structure shown in any one of formulas (1-1) to (1-32):

[0099]

[0100]

[0101]

[0102] In formulas (1-1) to (1-32), A1 to A 12 , G1~G4 are as defined in formula (1).

[0103] According to some embodiments, the organic compound represented by the above formula (1), or formulas (1-1) to (1-32) may be more specifically illustrated by the following compounds, but is not limited thereto.

[0104]

[0105]

[0106]

[0107]

[0108]

[0109] Hereinafter, an organic electroluminescent device using the above-mentioned organic electroluminescent compound and / or the above-mentioned organic electroluminescent material will be described.

[0110] An organic electroluminescent device according to one embodiment includes a first electrode; a second electrode; and at least one organic layer inserted between the first electrode and the second electrode. The organic layer may include at least one layer selected from the following: a hole transport layer, a hole injection layer, an electron blocking layer, a hole auxiliary layer, a luminescent auxiliary layer, a light-emitting layer, an electron transport layer, an electron injection layer, an intermediate layer, a hole blocking layer, and an electron auxiliary layer, and each layer may be further composed of several layers. In addition, the organic layer may further include at least one compound selected from the group consisting of: an arylamine-based compound and a styrylarylamine-based compound, and further include at least one metal selected from the group consisting of: a metal of Group 1 of the periodic table, a metal of Group 2, a transition metal of the 4th period, a transition metal of the 5th period, an organic metal of a lanthanide element and a d-transition element, or at least one complex compound containing such a metal.

[0111] The compound represented by formula (1) in the present disclosure may be included in one or more layers constituting an organic electroluminescent device. According to one embodiment, the organic layer includes a hole transport region and / or an electron transport region and / or a light-emitting layer comprising an organic electroluminescent compound according to the present invention, for example, a hole transport layer and / or a hole auxiliary layer and / or a hole blocking layer and / or an electron auxiliary layer and / or a light-emitting layer. For example, when a compound having formula (1) is contained in a hole transport layer and / or a hole auxiliary layer and / or a hole blocking layer and / or an electron auxiliary layer and / or a light-emitting layer, the compound having formula (1) may be included as a hole transport material and / or a hole auxiliary material and / or a hole blocking material and / or an electron auxiliary material and / or a host material, respectively. The hole transport layer and / or the hole auxiliary layer and / or the hole blocking layer and / or the electron auxiliary layer and / or the light-emitting layer may include, for example, a single organic electroluminescent compound of the present disclosure or a mixture of at least two organic electroluminescent compounds, and may further include conventional materials contained in the organic electroluminescent material.

[0112] One of the first electrode and the second electrode may be an anode, and the other may be a cathode. The first electrode and the second electrode may each be formed as a transmissive conductive material, a semi-transmissive reflective conductive material, or a reflective conductive material. Depending on the type of material forming the first electrode and the second electrode, the organic electroluminescent device may be a top-emitting type, a bottom-emitting type, or a double-sided emitting type.

[0113] A hole injection layer, a hole transport layer, an electron blocking layer, or a combination thereof can be used between the anode and the light-emitting layer. The hole injection layer can be a multilayer to reduce the hole injection barrier (or hole injection voltage) from the anode to the hole transport layer or the electron blocking layer, wherein each of the multilayers can use two compounds at the same time. The hole injection layer can be doped with a p-type dopant. In addition, the electron blocking layer can be placed between the hole transport layer (or hole injection layer) and the light-emitting layer, and the excitons can be confined in the light-emitting layer by blocking the electrons from overflowing from the light-emitting layer to prevent light leakage. The hole transport layer or the electron blocking layer can be a multilayer, and each layer can use a variety of compounds.

[0114] An electron buffer layer, a hole blocking layer, an electron transport layer, an electron injection layer, or a combination thereof may be used between the light-emitting layer and the cathode. The electron buffer layer may be a multilayer to control the injection of electrons and improve the interface characteristics between the light-emitting layer and the electron injection layer, wherein each of the multilayers may use two compounds at the same time. The hole blocking layer or the electron transport layer may also be a multilayer, wherein each of the multilayers may use a variety of compounds. In addition, the electron injection layer may be doped with an n-type dopant.

[0115] The luminescence auxiliary layer can be placed between the anode and the light-emitting layer, or between the cathode and the light-emitting layer. When the luminescence auxiliary layer is placed between the anode and the light-emitting layer, it can be used to promote hole injection and / or hole transport, or to prevent electron overflow. When the luminescence auxiliary layer is placed between the cathode and the light-emitting layer, it can be used to promote electron injection and / or electron transport, or to prevent hole overflow. In addition, the hole auxiliary layer can be placed between the hole transport layer (or hole injection layer) and the light-emitting layer, and can effectively promote or limit the hole transport rate (or hole injection rate), so that the charge balance can be controlled. When the organic electroluminescent device includes two or more hole transport layers, the hole transport layer further included can be used as a hole auxiliary layer or an electron blocking layer. The luminescence auxiliary layer, the hole auxiliary layer, or the electron blocking layer can have the effect of improving the efficiency and / or life of the organic electroluminescent device.

[0116] In the organic electroluminescent device disclosed in the present invention, at least one layer selected from a chalcogenide layer, a metal halide layer and a metal oxide layer (hereinafter referred to as a "surface layer") may preferably be placed on one or more inner surfaces of one or both electrodes. Specifically, a chalcogenide (including oxide) layer of silicon and aluminum is preferably placed on the anode surface of the electroluminescent medium layer, and a metal halide layer or a metal oxide layer is preferably placed on the cathode surface of the electroluminescent medium layer. The operational stability of the organic electroluminescent device can be obtained through the surface layer. Preferably, the chalcogenide includes SiOX (1≤X≤2), AlOX (1≤X≤1.5), SiON, SiAlON, etc.; the metal halide includes LiF, MgF2, CaF2, rare earth metal fluorides, etc.; and the metal oxide includes Cs2O, Li2O, MgO, SrO, BaO, CaO, etc.

[0117] In addition, in the organic electroluminescent device of the present disclosure, it is preferred that a mixed region of an electron transport compound and a reductive dopant, or a mixed region of a hole transport compound and an oxidative dopant be placed on at least one surface of a pair of electrodes. In this case, the electron transport compound is reduced to anions, and thus it becomes easier to inject and transport electrons from the mixed region to the electroluminescent medium. In addition, the hole transport compound is oxidized to cations, and thus it becomes easier to inject and transport holes from the mixed region to the electroluminescent medium. Preferably, the oxidative dopant includes various Lewis acids and acceptor compounds, and the reductive dopant includes alkali metals, alkali metal compounds, alkaline earth metals, rare earth metals, and mixtures thereof. The reductive dopant layer can be used as a charge generation layer to prepare an organic electroluminescent device having two or more light-emitting layers and emitting white light.

[0118] In order to form each layer of the organic electroluminescent device disclosed in the present invention, a dry film-forming method such as vacuum evaporation, sputtering, plasma, ion plating method, etc., or a wet film-forming method such as inkjet printing, nozzle printing, slit coating, spin coating, dip coating, flow coating method, etc. can be used.

[0119] When a wet film-forming method is used, a thin film can be formed by dissolving or diffusing the material forming each layer in any suitable solvent such as ethanol, chloroform, tetrahydrofuran, dioxane, etc. The solvent may be any solvent in which the material forming each layer can be dissolved or diffused and which has no problem in film-forming ability.

[0120] When a layer is formed by an organic electroluminescent compound according to an embodiment, the layer can be formed by the methods listed above, and can generally be formed by co-deposition or mixed deposition. Co-deposition is a mixed deposition method in which two or more materials are put into a corresponding single crucible source and current is applied to two chambers at the same time to evaporate the materials and perform mixed deposition; and mixed deposition is a mixed deposition method in which two or more materials are mixed in one crucible source before being deposited and then current is applied to one chamber to evaporate the materials.

[0121] According to one embodiment, the organic electroluminescent device of the present disclosure can be used to manufacture display devices such as smartphones, tablet computers, notebook computers, PCs, TVs, or display devices for vehicles, or lighting devices such as outdoor or indoor lighting.

[0122] Hereinafter, the preparation method of the compound according to the present disclosure will be explained with reference to representative compounds or intermediate compounds in order to understand the present disclosure in detail.

[0123] Synthesis Example:

[0124] The specific preparation method of the above-mentioned new compound of the present invention will be described in detail below by taking multiple synthesis examples as examples, but the preparation method of the present invention is not limited to these multiple synthesis examples. Those skilled in the art can make any modifications, equivalent substitutions, improvements, etc. on this basis without departing from the principles of the present invention, and expand the method to the scope of the technical solution claimed for protection by the claims of the present invention.

[0125] Unless otherwise specified, the compounds not mentioned in the present invention are all commercially available products; the mass spectrum in the present invention is measured by a ZABHS mass spectrometer (manufactured by Micromass, UK), and the nuclear magnetic resonance is measured by a Bruker 400 MHz nuclear magnetic resonance instrument (manufactured by Bruker, Germany).

[0126] Synthesis of compound H1:

[0127] To synthesize compound H1, the intermediate compound M1 (structure shown below) must first be synthesized, and its synthesis route is as follows:

[0128]

[0129] Synthesis of compound iii-M1:

[0130] Under nitrogen atmosphere, 1,2-dichloro-4,5-diiodobenzene (compound i-M1, 16.0 g, 40.0 mmol, 1 eq), phenylboric acid (compound ii-M1, 4.9 g, 40.0 mmol, 1 eq), tetrakis(triphenylphosphine)palladium (462.2 mg, 0.8 mmol, 1% eq) and degassed tetrahydrofuran (50 mL) were added to a three-necked flask in sequence, and the above system was mixed evenly, followed by adding potassium carbonate (50.0 mL, 2M deionized water solution, 100.0 mmol, 2.5 eq). Stirring was continued, and reflux reaction was carried out under nitrogen atmosphere for 6 hours. Thin layer chromatography analysis showed that there was basically no raw material remaining. The reaction system was cooled to room temperature, ethyl acetate (150 mL) was added, and the layers were separated after standing. The organic phase was collected, the aqueous phase was extracted with ethyl acetate (3x50 mL), the organic phases were combined, dried over anhydrous magnesium sulfate, filtered, and the solvent was removed by reduced pressure distillation. The obtained crude product was separated by rapid silica gel column chromatography (the mobile phase was a mixed solvent of n-hexane / ethyl acetate) and recrystallized from ethanol to obtain compound iii-M1 (11.0 g, yield 78.8%).

[0131] Synthesis of compound v-M1:

[0132] Compound v-M1 was synthesized by referring to the preparation method of compound iii-M1, except that the raw materials compound iii-M1 and compound iv-M1 were used in equivalent amounts to replace compound i-M1 and compound ii-M1, respectively. The reaction yield was 82.5%.

[0133] Synthesis of compound vi-M1:

[0134] In a nitrogen atmosphere, N, N-dimethylformamide (DMF, 100 mL) and compound v-M1 (8.6 g, 25.0 mmol, 1 eq) were added to a three-necked flask in sequence. After thorough mixing, reduced iron powder (7.0 g, 125.0 mmol, 5 eq) was added while stirring, followed by slow addition of concentrated hydrochloric acid (11 mL, mass fraction 37%), and heating to 80 ° C for 3 hours under a nitrogen atmosphere. Thin layer chromatography analysis showed that there was basically no raw material remaining. The temperature was lowered to room temperature, and a solution of sodium carbonate (18.0 g) in water (100 mL) was slowly poured into the reaction solution. After stirring for 30 minutes, a large amount of precipitate was precipitated. Filter by suction, collect the filter cake, and dissolve it in ethyl acetate (120 mL), stirring at 60 ° C for 30 minutes. Filter by suction again, collect the filtrate, dry it with anhydrous magnesium sulfate, filter it, and remove the solvent by reduced pressure distillation. The obtained crude product was separated by rapid silica gel column chromatography (the mobile phase was a mixed solvent of n-hexane / ethyl acetate) to obtain compound vi-M1 (6.4 g, yield 81.4%).

[0135] Synthesis of compound M1:

[0136] Under nitrogen atmosphere, anhydrous tetrahydrofuran (30mL), isoamyl nitrite (7.0g, 60.0mmol, 3eq) and copper powder (381.3mg, 6.0mmol, 10%eq) were added to a three-necked flask in sequence. Stirring was started, and then a tetrahydrofuran (25mL) solution of compound M-a6 (6.2g, 20.0mmol, 1eq) was added dropwise for 5 minutes. After the addition was completed, the reaction system was heated to reflux and reacted for 1 hour under nitrogen atmosphere. Thin layer chromatography analysis showed that there was basically no raw material remaining. The temperature was lowered to room temperature, and a saturated sodium chloride aqueous solution (70mL) was added to the reaction solution, stirred for 5 minutes, and allowed to stand for stratification. The organic phase was collected with a separatory funnel, the aqueous phase was extracted with ethyl acetate (2×50mL), the organic phases were combined, dried over anhydrous magnesium sulfate, filtered, and the solvent was removed by reduced pressure distillation. The crude product was separated by rapid silica gel column chromatography (the mobile phase was a mixed solvent of n-hexane / ethyl acetate) and recrystallized from ethanol to obtain compound M1 (5.0 g, yield 84.2%). The total yield of the four-step reaction was 44.5%. Mass spectrum (m / z) = 297.02 [M+H] + . 1 H NMR (400MHz, DMSO-d6) δ8.54(s,2H),7.93–7.89(m,4H),7.61–7.52(m,4H).

[0137] Using the intermediate compound M1 as the starting material, compound H1 was synthesized. The synthetic route is as follows:

[0138]

[0139] Synthesis of compound ii-H1:

[0140] Under nitrogen atmosphere, compound M1 (4.5 g, 15.0 mmol, 1 eq), compound i-H1 (3.5 g, 15.0 mmol, 1 eq), tetrakis(triphenylphosphine)palladium (346.7 g, 0.3 mmol, 2% eq), degassed toluene (120 mL) and ethanol (80 mL) were added to a three-necked flask in sequence. The above system was mixed evenly, and potassium carbonate (37.5 mL, 2M deionized water solution, 75.0 mmol, 5 eq) was then added. Stirring was continued, and the reaction was refluxed under nitrogen atmosphere for 8 hours. There was basically no raw material remaining by thin layer chromatography analysis. The reaction system was cooled to room temperature and separated after standing. The organic phase was collected, the aqueous phase was extracted with toluene (3x30 mL), the organic phases were combined, dried over anhydrous magnesium sulfate, filtered and the solvent was removed by distillation under reduced pressure. The obtained crude product was separated by rapid silica gel column chromatography (the mobile phase was a mixed solvent of n-hexane / ethyl acetate) and recrystallized from ethanol to obtain compound ii-H1 (5.2 g, yield 77.2%).

[0141] Synthesis of compound H1

[0142] In a nitrogen atmosphere, compound ii-H1 (5.0 g, 11.1 mmol, 1 eq), compound iii-H1 (4.0 g, 11.1 mmol, 1 eq) and degassed toluene (50 mL) were added to a dry three-necked flask in sequence, and stirred thoroughly. Then sodium tert-butoxide (1.6 g, 16.7 mmol, 1.5 eq), bis(dibenzylideneacetone palladium) (63.2 mg, 0.11 mmol, 1% eq), and tri-tert-butylphosphine (0.55 mL, 10% n-hexane solution, 0.22 mmol, 2% eq) were added respectively. Stirring was started, the above reaction system was fully mixed, and the temperature was raised to reflux under a nitrogen atmosphere. After reacting for 10 hours, there was basically no raw material remaining by thin layer chromatography analysis, and heating was stopped. After the temperature of the reaction system dropped to room temperature, a mixed solution of 5 mL of concentrated hydrochloric acid (37% aqueous solution) and 100 mL of deionized water was added thereto, and the layers were allowed to stand for separation. The organic phase was retained, and the aqueous phase was extracted with toluene (3×20 mL), combined with the above-retained organic phase, and the solvent was removed by vacuum distillation. The crude product was successively separated by silica gel column chromatography (the mobile phase was a mixed solvent of n-hexane / toluene), and recrystallized from a mixed solvent of toluene / ethanol to obtain the target compound H1 (7.2 g, yield 83.5%). The total yield of the two-step reaction was 64.5%. Mass spectrum (m / z) = 774.40 [M+H] + . 1 H NMR (400MHz, DMSO-d6) δ8.86(s,1H),8.41(s,1H),8.30(dd,J=7.5,1.5Hz,1H),7.82(dd,J=7.5,1.5Hz ,1H),7.79(dt,J=7.4,1.2Hz,1H),7.72(dd,J=7.3,1.4Hz,1H),7.70(d,J=7.5Hz,1H),7.68–7.64(m,2 H),7.61–7.52(m,7H),7.48–7.45(m,1H),7.43–7.29(m,7H),7.23(dd,J=7.5,1.5Hz,1H),7.19(d,J=7 .6Hz,1H),7.17–7.13(m,2H),6.97–6.96(m,1H),1.74(s,4H),1.59(s,6H),1.29(s,6H),1.28(s,6H).

[0143] Synthesis of compound H175:

[0144]

[0145] Referring to the preparation method of compound ii-H1, compound H175 was finally obtained by two-step Suzuki coupling reaction and intermediate compound ii-H175. Compound iii-H175 was synthesized by referring to the method described in application publication number CN 110526825 A. The total yield of the two-step reaction was 63.8%. Mass spectrum (m / z) = 904.48 [M+H] + . 1 H NMR (400MHz, DMSO-d6) δ9.78(s,1H),9.09(s,1H),7.82(dd,J=7.5,1.5Hz,2H),7.72(dd,J=7.5,1.5Hz ,2H),7.69(d,J=7.4Hz,2H),7.62(td,J=7.1,2.3Hz,2H),7.59–7.53(m,6H),7.47–7.43(m,3H),7.37( td,J=7.4,1.7Hz,2H),7.30(td,J=7.4,1.5Hz,2H),7.23(dd,J=7.5,1.6Hz,2H),7.17(dt,J=7.6,1.6H z,3H),7.05(d,J=1.4Hz,1H),6.97–6.95(m,2H),1.59(s,12H),1.31(s,6H),1.29(s,6H),1.04(s,6H).

[0146] The following compounds involved in the present invention were synthesized with reference to the preparation method of compound H1 or H175. Among them, the synthesis of the key intermediate dihalogenated triphenylene was referenced to the preparation method of compound M1, and its chemical structure and the raw material compounds used are shown in Table 1. The compound structure of the target product and the raw material compounds used are shown in Table 2.

[0147] Table 1

[0148]

[0149]

[0150]

[0151]

[0152]

[0153] Table 2

[0154]

[0155]

[0156]

[0157]

[0158]

[0159]

[0160]

[0161] The NMR data of the representative compounds involved in the synthesis examples are shown in Table 3.

[0162] Table 3

[0163]

[0164]

[0165]

[0166] Device Example:

[0167] The compounds used in the device are all purified by sublimation, and the purity is greater than 99.98%.

[0168] The compound involved in the present invention can be used as an electron blocking layer material for various color light OLED devices. The specific device manufacturing method and test results are given below.

[0169] Preparation of red organic electroluminescent devices

[0170] Red light device embodiment 1:

[0171] According to Figure 1The structure shown is used to make a red bottom-emitting organic electroluminescent device, and the preparation process is as follows: on a glass substrate 101, a transparent ITO film layer (thickness 150nm) is formed by a magnetron sputtering process to obtain a first electrode 102 as an anode. A mixed material of compound 1 and compound 2 is evaporated on the surface of the anode as a hole injection layer 103, with a mixing ratio of 3:97 (mass ratio) and a thickness of 10nm; then compound 2 (thickness 100nm) and compound H12 of the present invention (thickness 20nm) are sequentially evaporated on the surface of the hole injection layer to obtain a hole transport layer 104 and an electron blocking layer 105, respectively. Next, on the surface of the electron blocking layer 105, compound 3 and compound 4 are co-evaporated at a mass ratio of 95:5 to form an organic light-emitting layer 106 (thickness 40nm). Subsequently, compound 5 is sequentially evaporated on the surface of the organic light-emitting layer to form a hole blocking layer 107 (thickness 10nm), and compound 6 and LiQ with a mixing ratio of 4:6 (mass ratio) form an electron transport layer 108 (thickness 30nm). Finally, magnesium (Mg) and silver (Ag) are mixed and deposited on the surface of the electron transport layer 108 at an evaporation rate of 1:9 to form a second electrode 109 with a thickness of 10 nm as a cathode, thereby completing the manufacture of the organic light-emitting device.

[0172] The chemical structures of compounds 1 to 6 and LiQ are shown in Table 4.

[0173] Table 4

[0174]

[0175] Red light device embodiments 2 to 24

[0176] The organic electroluminescent device was prepared by the same method as in Example 1 of the red light device, except that the compound H12 was replaced by the compounds in Table 5 below when forming the electron blocking layer.

[0177] Comparative Examples 1-2

[0178] The organic electroluminescent device was prepared by the same method as in Example 1 of the red light device, except that compound EB-1 and compound EB-2 (chemical structures are shown below) were used to replace compound H12 when forming the electron blocking layer.

[0179]

[0180] The operating voltage and efficiency of the organic electroluminescent device prepared as above were calculated by a computer-controlled Keithley 2400 test system (test current was 20 mA / cm 2The device lifetime under dark conditions was obtained using a Polaronix (McScience Co.) lifetime measurement system equipped with a power supply and a photodiode as a detection unit (test conditions: constant current 20 mA / cm 2 LT95 refers to the time required for the brightness to decrease from the initial brightness to 95%. The test results are shown in Table 5.

[0181] Table 5

[0182]

[0183]

[0184] Preparation of green organic electroluminescent devices

[0185] Green light device embodiment 1:

[0186] According to Figure 1 The structure shown is used to make a green bottom-emitting organic electroluminescent device, and the preparation process is as follows: on a glass substrate 101, a transparent ITO film layer (thickness 150nm) is formed by a magnetron sputtering process to obtain a first electrode 102 as an anode. A mixed material of compound 1 and compound 2 is evaporated on the surface of the anode as a hole injection layer 103, with a mixing ratio of 3:97 (mass ratio) and a thickness of 10nm; then compound 2 (thickness 100nm) and compound H1 of the present invention (thickness 40nm) are sequentially evaporated on the surface of the hole injection layer to obtain a hole transport layer 104 and an electron blocking layer 105, respectively. Next, on the surface of the electron blocking layer 105, compound 3-3A, compound 3-3B and compound 3-4 are co-evaporated at a mass ratio of 45:45:10 to form an organic light-emitting layer 106 (thickness 40nm). Subsequently, compound 5 is sequentially evaporated on the surface of the organic light-emitting layer to form a hole blocking layer 107 (thickness 10 nm), and compound 6 and LiQ with a mixing ratio of 4:6 (mass ratio) are formed into an electron transport layer 108 (thickness 30 nm). Finally, magnesium (Mg) and silver (Ag) are mixed and deposited on the surface of the electron transport layer 108 at an evaporation rate of 1:9 to form a second electrode 109 with a thickness of 10 nm as a cathode, completing the manufacture of the organic light-emitting device.

[0187] The chemical structures of compounds 1, 5, 6 and LiQ are described above, and the chemical structures of compounds 3-3A, 3-3B and 3-4 are shown in Table 6.

[0188] Table 6

[0189]

[0190] Green light device embodiments 2 to 22

[0191] The organic electroluminescent device was prepared by the same method as in Example 1 of the green light device, except that the compound H1 was replaced by the compounds in Table 9 below when forming the electron blocking layer.

[0192] Comparative Examples 3-5

[0193] The organic electroluminescent device was prepared in the same manner as in Example 1 of the green light device, except that the compound EB-3, EB-4, and EB-5 (chemical structures shown below) were used to replace the compound H1 when forming the electron blocking layer.

[0194]

[0195] The operating voltage and efficiency of the organic electroluminescent device prepared as above were calculated by a computer-controlled Keithley 2400 test system (test current was 20 mA / cm 2 The device lifetime under dark conditions was obtained using a Polaronix (McScience Co.) lifetime measurement system equipped with a power supply and a photodiode as a detection unit (test conditions: constant current 20 mA / cm 2 LT95 refers to the time required for the brightness to decrease from the initial brightness to 95%. The test results are shown in Table 7.

[0196] Table 7

[0197]

[0198]

[0199] Referring to Table 5, it can be seen that the red light device embodiments 1 to 24 using the compounds of the present invention as electron blocking layer materials for organic electroluminescent red light devices, compared with comparative examples 1 to 2, the device voltage is reduced by at least 3.9%, the device efficiency is increased by at least 15.1%, and the life is increased by at least 23.8%.

[0200] Referring to Table 7, it can be seen that the green light device embodiments 1 to 22 using the compounds of the present invention as electron blocking layer materials for organic electroluminescent green light devices, compared with comparative examples 3 to 5, the device voltage is reduced by at least 5.0%, the device efficiency is increased by at least 8.3%, and the life is increased by at least 66.7%.

[0201] The compounds of the present invention, compared with the comparative example compounds EB-1, EB-2, EB-3 and EB-4, the substituents on the triphenylene fragment are changed from phenyl to cycloalkylphenylene, which can regulate the intermolecular interaction, facilitate the formation of a stable, amorphous, uniform film morphology, and are not easily affected by the temperature and significantly changed macroscopically, so that the efficiency and life of the device are greatly improved. In the device comparative example 5, although its life is comparable to that of the device embodiment of the present invention, the voltage is high and the luminous efficiency is low. The reason may be that in the comparative example compound EB-5, the cycloalkylphenylene is connected to the phenylene. Since the aromaticity of triphenylene is stronger than benzene, when the cycloalkylphenylene of the same electron-donating property is connected, the "push-pull electron effect" formed by triphenylene is stronger than phenyl, which is more conducive to the transfer of holes from one molecule to another molecule, so that the device has higher efficiency and can be driven at a lower voltage.

[0202] The above description is only a preferred specific implementation manner of the present invention, but the protection scope of the present invention is not limited thereto. Any technician familiar with the technical field can make equivalent replacements or changes according to the technical scheme and inventive concept of the present invention within the technical scope disclosed by the present invention, which should be covered by the protection scope of the present invention.

Claims

1. An organic compound having a chemical structure as shown in formula (1): in, A1~A 12 are the same or different and are each independently selected from hydrogen, a group represented by formula (2), or a group represented by formula (3); And meet the conditions: A1~A 12 Among them, at least one is selected from the group represented by formula (2), and at least one is selected from the group represented by formula (3); In formula (2), R is selected from hydrogen, deuterium, methyl or deuterated methyl; n is selected from 1 or 2; Among G1 to G4, there is only one bonding site, which is the same as A1 to A 12 The rest are the same or different and are independently selected from hydrogen, methyl, methoxy and phenyl; In formula (3), L0, L1, and L2 are the same or different and are each independently selected from a single bond, In any of the above groups, any two and only two carbon atoms on the aromatic or heteroaromatic rings are bonding sites, or any hydrogen atom is unsubstituted or substituted, and when any hydrogen atom is substituted, it is substituted by phenyl; Ar1 and Ar2 are the same or different and are independently selected from In any of the above groups, any and only one carbon on the aromatic ring or heteroaromatic ring is a bonding site, and / or any hydrogen atom is unsubstituted or substituted, and when any hydrogen atom is substituted, it is substituted by one of methoxy, deuterated methyl, and phenyl.

2. An organic compound, characterized in that The organic compound is selected from any of the following chemical structures:

3. An organic electroluminescent material comprising the organic compound according to any one of claims 1 to 2.

4. The organic compound according to any one of claims 1 to 2, characterized in that Its application is as a functional material in organic electronic devices, including organic electroluminescent devices, organic thin film transistors, organic solar cells, organic-inorganic hybrid solar cells, optical sensors, radio frequency identification tags or electronic paper.

5. An organic electroluminescent device, comprising a first electrode, a second electrode and one or more light-emitting functional layers located between the first electrode and the second electrode, wherein the light-emitting functional layer contains the organic compound described in any one of claims 1 to 2; the light-emitting functional layer comprises a hole transport region, a light-emitting layer and an electron transport region, wherein the hole transport region is formed on an anode layer, the cathode layer is formed on the electron transport region, and the light-emitting layer is between the hole transport region and the electron transport region; wherein, The organic compound described in any one of claims 1 to 2 is contained in a hole transport region and / or an electron transport region and / or a light emitting layer.

Citation Information

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