Organic compound and organic layer and application thereof, organic electroluminescent device and display or lighting device

Abstract

The invention discloses an organic compound, an organic layer, application of the organic compound and the organic layer, an organic electroluminescent device and a display or lighting device, the structural formula of the organic compound is shown in the formula I: # imgabs0 #, in the formula I, Ar is selected from substituted or unsubstituted C6-C60 aryl and substituted or unsubstituted C3-C60 heteroaryl; r1 is selected from an unsubstituted, substituted or unsubstituted straight chain or branched chain alkyl group of C1-C60, a substituted or unsubstituted cycloalkyl group of C3-C60, a substituted or unsubstituted hetero-alkyl group of C1-C60, a substituted or unsubstituted hetero-cycloalkyl group of C1-C60, a substituted or unsubstituted aryl group of C6-C60, or a substituted or unsubstituted hetero-aryl group of C3-C60; and X is selected from O, S, N and CR2R3. When the organic compound is applied to the organic electroluminescent device, the working voltage of the device can be reduced, the current efficiency of the device is improved, the service life of the device is prolonged, and the organic compound has excellent color purity.

Description

Technical Field

[0001] The present application relates to the technical field of organic electroluminescent materials, and in particular to an organic compound and an organic layer and applications thereof, an organic electroluminescent device, and a display or lighting device. Background Art

[0002] Organic Light-Emitting Diode (OLED) is a type of self-luminous electronic component. Compared with liquid crystal display (LCD), organic electroluminescent displays are usually driven at low voltage and do not require an additional backlight source, so they have advantages in power consumption and manufacturing process. In addition, organic electroluminescent displays also have the characteristics of high brightness, high contrast, excellent color expression, wide viewing angle, and fast response speed, and have received widespread attention from academia and industry. Although the research progress of organic electroluminescent devices is very rapid, there are still many problems that need to be solved, such as the operating voltage, current efficiency and life of the device, which still need to be improved.

[0003] Organic electroluminescent materials are primarily composed of a mixture of a host material and a guest material. Holes and electrons are injected from the anode and cathode, respectively, through the hole transport layer and electron transport layer, into the host of the light-emitting layer, where they recombine to form excitons. The exciton energy is then transferred from the host to the guest, causing the light to be emitted. Generally, the host accounts for 85% to 99% of the mass of the light-emitting layer. Therefore, the properties of the host material are crucial to the performance of OLEDs. Summary of the Invention

[0004] The purpose of this application is to provide an organic compound and an organic layer and their applications, an organic electroluminescent device, a display or lighting device, which can significantly improve the current efficiency, luminous efficiency and life of the organic electroluminescent device, reduce the operating voltage of the device, and at the same time have excellent color purity.

[0005] To achieve the above objectives, the technical solution of the present application provides an organic compound, the structural formula of which is shown in Formula I: In the formula I, Ar is selected from substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl; R1 is selected from none, substituted or unsubstituted linear or branched C1-C60 alkyl, substituted or unsubstituted C3-C60 cycloalkyl, substituted or unsubstituted C1-C60 heteroalkyl, substituted or unsubstituted C1-C60 heterocycloalkyl, substituted or unsubstituted C6-C60 aryl, or substituted or unsubstituted C3-C6 0 heteroaryl; X is selected from O, S, N, CR2R3, wherein: R2 and R3 are independently selected from hydrogen, substituted or unsubstituted linear or branched C1-C60 alkyl, substituted or unsubstituted C3-C60 cycloalkyl, substituted or unsubstituted C1-C60 heteroalkyl, substituted or unsubstituted C1-C60 heterocycloalkyl, substituted or unsubstituted C6-C60 aryl, or substituted or unsubstituted C3-C60 heteroaryl, or R2 and R3 are bonded to form a ring.

[0006] In some embodiments of the present application, Ar is a group The structural formula of the organic compound is shown in Formula II: In Formula II, L1 is selected from a single bond, a substituted or unsubstituted C6-C30 arylene group, or a substituted or unsubstituted C3-C30 heteroarylene group; Ar1 and Ar2 are independently selected from a substituted or unsubstituted C6-C30 arylene group, or a substituted or unsubstituted C3-C30 heteroarylene group; and n is an integer from 0 to 4.

[0007] In some embodiments of the present application, L1 is selected from a single bond or a substituted or unsubstituted group: phenyl, biphenyl, naphthyl, phenanthrenyl, spirofluorenyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, triphenylene, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, one or more combinations thereof; Ar1 and Ar2 are independently selected from a substituted or unsubstituted group: phenyl, biphenyl, naphthyl, phenanthrenyl, spirofluorenyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, triphenylene, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, one or more combinations thereof.

[0008] In some embodiments of the present application, the organic compound represented by Formula II is represented by any one of the structural formulas of Formula 1 to Formula 84.

[0009] In some embodiments of the present application, the organic compound represented by Formula II is compounds H-1 to H-14.

[0010] In some embodiments of the present application, Ar is a group L2-EA; the structural formula of the organic compound is shown in Formula III: In the formula III, L2 is selected from a single bond, a substituted or unsubstituted C6-C30 arylene group, or a substituted or unsubstituted C3-C30 heteroarylene group; EA is selected from one or a combination of cyano derivatives, trifluoromethyl, fluoroaryl, fluoroalkyl, nitrogen-containing aromatic groups, and phosphorus oxide derivatives.

[0011] In some embodiments of the present application, L2 is selected from a single bond or a substituted or unsubstituted group: phenyl, biphenyl, naphthyl, phenanthrenyl, spirofluorenyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, triphenylene, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, one or more combinations thereof; and EA is selected from a triazine derivative, a cyano derivative, or a phosphorus oxide derivative or a combination thereof.

[0012] In some embodiments of the present application, the EA is And Ar9 and Ar 10 Independently selected from the following substituted or unsubstituted groups: phenyl, naphthyl, benzonaphthyl, biphenyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, fluorenyl, spirofluorene, triphenylene, phenanthrenyl or phenanthrenyl derivatives.

[0013] In some embodiments of the present application, the organic compound represented by Formula III is represented by any one of the structural formulas of Formula 85 to Formula 183.

[0014] In some embodiments of the present application, the organic compound represented by formula III is compounds E-1 to E-14.

[0015] In some embodiments of the present application, Ar is a group The structural formula of the organic compound is shown in Formula IV: In the formula IV, L3 is selected from a single bond, a substituted or unsubstituted C6-C30 arylene group, or a substituted or unsubstituted C3-C30 heteroarylene group; Ar3 is selected from a substituted or unsubstituted C6-C30 aryl group, or a substituted or unsubstituted C3-C30 heteroaryl group.

[0016] In some embodiments of the present application, L3 is selected from a single bond or a substituted or unsubstituted group: phenyl, biphenyl, naphthyl, phenanthrenyl, spirofluorenyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, triphenylene, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, one or more combinations thereof; Ar3 is selected from a substituted or unsubstituted group: phenyl, biphenyl, naphthyl, phenanthrenyl, spirofluorenyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, triphenylene, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, one or more combinations thereof.

[0017] In some embodiments of the present application, the organic compound represented by Formula IV is represented by any one of the structural formulas of Formula B-1 to Formula B-14.

[0018] The present application also provides an organic compound, the structural formula of which is shown in Formula V: In the formula V, Ar4 to Ar8 are independently selected from substituted or unsubstituted C6 to C30 arylene groups, substituted or unsubstituted C3-C30 heteroarylene groups, and at least one of Ar4 to Ar8 comprises a structural formula of formula VI; and in the formula VI: * is a connection site, and the connection site is one or more; R1 is selected from none, substituted or unsubstituted straight or branched C1 to C60 alkyl groups, substituted or unsubstituted C3 to C60 cycloalkyl groups, substituted or unsubstituted C1 to C60 heteroalkyl groups, substituted or unsubstituted C1 to C60 heterocycloalkyl groups. R2 and R3 are independently selected from hydrogen, substituted or unsubstituted linear or branched C1-C60 alkyl, substituted or unsubstituted C3-C60 cycloalkyl, substituted or unsubstituted C1-C60 heteroalkyl, substituted or unsubstituted C1-C60 heterocycloalkyl, substituted or unsubstituted C6-C60 aryl, or substituted or unsubstituted C3-C60 heteroaryl, or R2 and R3 are bonded to form a ring.

[0019] In some embodiments of the present application, Ar4 to Ar8 are independently selected from the following substituted or unsubstituted groups: phenyl, biphenyl, naphthyl, phenanthrenyl, spirofluorenyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, triphenylene, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, or a combination of several thereof.

[0020] In some embodiments of the present application, the organic compound represented by Formula V is represented by any one of the structural formulas of Formula D-1 to Formula D-14.

[0021] The present application also provides an organic layer, comprising any one of the aforementioned organic compounds.

[0022] The present application also provides use of any of the aforementioned organic compounds and / or the aforementioned organic layers in an organic electroluminescent device.

[0023] The present application also provides an organic electroluminescent device, comprising a first electrode, a second electrode and the aforementioned organic layer, wherein the organic layer is 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.

[0024] The present application also provides a display or lighting device, comprising the aforementioned organic electroluminescent device.

[0025] The organic compound of the present application adopts a spirobiindene structure and an aromatic ring as a parent core structure. The conjugated effect formed thereby enables the organic compound to improve various properties of an organic electroluminescent device when used as an organic electroluminescent material. BRIEF DESCRIPTION OF THE DRAWINGS

[0026] The following figures describe in detail exemplary embodiments disclosed in this application. Identical reference numerals denote similar structures in several views of the drawings. Those skilled in the art will appreciate that these embodiments are non-limiting, exemplary embodiments, and that the drawings are for illustration and description purposes only and are not intended to limit the scope of this application. Other embodiments may also achieve the same inventive intent as described in this application. It should be understood that the drawings are not drawn to scale. Among them:

[0027] Figure 1 Schematic diagram of the structure of the organic electroluminescent device in device embodiment 1;

[0028] Figure 2 Schematic diagram of the structure of the organic electroluminescent device in device embodiment 15;

[0029] Figure 3 Schematic diagram of the structure of the organic electroluminescent device in device embodiment 29;

[0030] Figure 4 This is a schematic structural diagram of the organic electroluminescent device in device example 43. DETAILED DESCRIPTION

[0031] The following description provides specific application scenarios and requirements of the present application, with the purpose of enabling those skilled in the art to make and use the content of this application. Various local modifications to the disclosed embodiments will be apparent to those skilled in the art, and the general principles defined herein may be applied to other embodiments and applications without departing from the spirit and scope of this application. Therefore, this application is not limited to the embodiments shown, but is intended to be of the widest scope consistent with the claims.

[0032] Based on the current demand for improving the various performances of organic electroluminescent devices, the inventors of this application have obtained an organic compound after extensive exploration and research. This organic compound uses a spirobiindene structure and an aromatic ring cyclic structure as the parent core structure, which can form a strong conjugation effect. When used as a hole transport material, electron transport material, host material and doping material, it can significantly improve the current efficiency and luminous efficiency of the device, reduce the operating voltage of the device, and extend the device life.

[0033] The following are examples of substituents that may appear in this application, but the substituents are not limited thereto:

[0034] Substituted or unsubstituted: refers to being substituted with one or more substituents selected from the group consisting of deuterium, a halogen group, a nitrile group, a nitro group, a hydroxyl group, a carbonyl group, an ester group, an imide group, an amino group, a phosphine oxide group, an alkoxy group, an aryloxy group, an alkylthio group, an arylthio group, an alkylsulfonyl group, an arylsulfonyl group, a silyl group, a boron group, a linear or branched or cyclic alkyl group, an alkenyl group, an aryl group, an aralkyl group, an aralkenyl group, an alkylaryl group, an alkylamino group, an aralkylamino group, a heteroarylamino group, an arylamino group, an arylphosphino group, a heterocyclic group, or being unsubstituted; or being substituted with a substituent that connects two or more of the substituents listed above, or being unsubstituted. For example, a “substituent that connects two or more substituents” may include a biphenyl group, i.e., a biphenyl group may be an aryl group, or a substituent that connects two phenyl groups. The linear, branched or cyclic alkyl group is preferably a C1 to C30 alkyl group, such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl, methyl-substituted isobutyl, methyl-substituted tert-butyl, etc.

[0035] Aryl: There are no particular limitations and the aryl group may be a monocyclic aryl group or a polycyclic aryl group. In some embodiments, monocyclic aryl groups include, but are not limited to, phenyl, biphenyl, terphenyl, quaterphenyl, pentphenyl, and the like. Polycyclic aryl groups include, but are not limited to, naphthyl, anthracenyl, phenanthrenyl, pyrenyl, perylenyl, and fluorenyl. The fluorenyl group may be substituted, such as 9,9'-dimethylfluorenyl and fluorenyl. Furthermore, two of the substituents may combine to form a spirocyclic structure, such as 9,9'-spirobifluorenyl.

[0036] The above description of the aryl group applies to the arylene group, except that the arylene group is divalent.

[0037] The above description of the aryl group can be applied to the aryl group in the aryloxy group, arylthio group, arylsulfonyl group, arylphosphino group, arylalkyl group, arylalkylamino group, arylalkenyl group, alkylaryl group, arylamino group and arylheteroarylamino group.

[0038] Heterocyclic group: contains one or more of B, N, O, P, S, Si and Se as heteroatoms. Heterocyclic groups include, but are not limited to, pyridyl, pyrrolyl, pyrimidinyl, pyridazinyl, furyl, thienyl, imidazolyl, pyrazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, triazolyl, oxadiazolyl, thiadiazolyl, dithiazolyl, tetrazolyl, pyranyl, thiopyranyl, pyrazinyl, azinyl, thiazinyl, dioxinyl, triazinyl, tetrazinyl, quinolyl, isoquinolyl, quinolyl, quinazolinyl, quinoxalinyl, naphthyridinyl, acridinyl, xanthanenyl, phenanthridinyl, naphthyridinyl, triazaindenyl, indolyl, dihydroindolinyl, indolizinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, Pyrazinopyrazinyl, benzothiazolyl, benzoxazolyl, benzimidazolyl, benzothiophenyl, dibenzothiophenyl, dibenzofuranyl, carbazolyl, benzocarbazolyl, dibenzocarbazolyl, indolocarbazolyl, indenocarbazolyl, phenazinyl, imidazopyridinyl, phenazinyl, phenanthridinyl, phenanthrolinyl, phenothiazinyl, imidazopyridinyl, imidazophenanthridinyl, benzimidazoquinazolinyl, benzimidazophenanthridinyl, spiro[fluorene-9,9'-xanthene], benzobinaphthyl, dinaphthofuranyl, naphthylbenzofuranyl, dinaphthothienyl, naphthylbenzothienyl, triphenylphosphine oxide, triphenylborane, etc.

[0039] The above description of heterocyclyl groups applies to heteroaryl groups, except that the heteroaryl group is aromatic.

[0040] The above description of the heterocyclic group can be applied to the heteroaryl group in the heteroaryl group, the heteroarylamine group and the arylheteroarylamine group.

[0041] The above description of the heterocyclyl group applies to the heteroarylene group, except that the heteroarylene group is divalent.

[0042] Alkyl group: may be linear, branched or cyclic, and the number of carbon atoms is not particularly limited. In some embodiments, alkyl groups include, but are 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, 5-methylhexyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, and the like.

[0043] The above description of the alkyl group can be applied to the alkyl group in the alkylthio group, alkylsulfonyl group, aralkyl group, aralkylamino group, alkylaryl group and alkylamino group.

[0044] One aspect of the present application provides an organic compound having the structural formula shown in Formula I:

[0045] In Formula I, Ar is selected from a substituted or unsubstituted C6-C60 aryl group or a substituted or unsubstituted C3-C60 heteroaryl group. R1 is selected from a null, substituted or unsubstituted linear or branched C1-C60 alkyl group, a substituted or unsubstituted C3-C60 cycloalkyl group, a substituted or unsubstituted C1-C60 heteroalkyl group, a substituted or unsubstituted C1-C60 heterocycloalkyl group, a substituted or unsubstituted C6-C60 aryl group, or a substituted or unsubstituted C3-C60 heteroaryl group. The substitution positions of Ar and R1 are not limited; both can be substituted at any substitutable position in Formula I.

[0046] In some preferred embodiments, R1 is selected from a null, substituted or unsubstituted linear or branched C1-C60 alkyl group, a substituted or unsubstituted C6-C60 aryl group, or a substituted or unsubstituted C3-C60 heteroaryl group.

[0047] In Formula I, X is selected from O, S, N, CR2R3, wherein: R2 and R3 are independently selected from hydrogen, substituted or unsubstituted linear or branched C1-C60 alkyl, substituted or unsubstituted C3-C60 cycloalkyl, substituted or unsubstituted C1-C60 heteroalkyl, substituted or unsubstituted C1-C60 heterocycloalkyl, substituted or unsubstituted C6-C60 aryl, or substituted or unsubstituted C3-C60 heteroaryl, or R2 and R3 are bonded to form a ring. Further preferably, R2 and R3 are independently selected from hydrogen, substituted or unsubstituted linear or branched C1-C60 alkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl, or R2 and R3 are bonded to form a ring.

[0048] In some embodiments, Ar is a group The structural formula of the organic compound is shown in Formula II: In Formula II, L1 is selected from a single bond, a substituted or unsubstituted C6-C30 arylene group, or a substituted or unsubstituted C3-C30 heteroarylene group. Ar1 and Ar2 are independently selected from a substituted or unsubstituted C6-C30 arylene group, or a substituted or unsubstituted C3-C30 heteroarylene group. n is an integer from 0 to 4.

[0049] In some preferred embodiments, L1 is selected from a single bond or a substituted or unsubstituted group consisting of one or more of the following: phenyl, biphenyl, naphthyl, phenanthrenyl, spirofluorenyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, triphenylene, 9,9-dimethylfluorenyl, and 9,9-diphenylfluorenyl. Ar1 and Ar2 are independently selected from a substituted or unsubstituted group consisting of one or more of the following: phenyl, biphenyl, naphthyl, phenanthrenyl, spirofluorenyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, triphenylene, 9,9-dimethylfluorenyl, and 9,9-diphenylfluorenyl.

[0050] In some preferred embodiments, the organic compound represented by Formula II is represented by any one of the following structural formulas:

[0051]

[0052]

[0053]

[0054]

[0055] In Formulae 1 to 84, Ar2 is selected from the following groups:

[0056]

[0057] In some more preferred embodiments, the organic compound represented by Formula II is the following compound:

[0058]

[0059] Device experiments have shown that when the organic compound represented by Formula II is used in hole transport materials, the operating voltage of the device can be significantly reduced, the luminous efficiency can be improved, and the service life can be extended.

[0060] In some embodiments, Ar is a group L2-EA, and the structural formula of the organic compound is shown in Formula III: In Formula III, L2 is selected from a single bond, a substituted or unsubstituted C6-C30 arylene group, or a substituted or unsubstituted C3-C30 heteroarylene group. EA is selected from one or a combination of a cyano derivative, a trifluoromethyl group, a fluoroaryl group, a fluoroalkyl group, a nitrogen-containing aromatic group, and a phosphorus-oxygen derivative.

[0061] In some preferred embodiments, L2 is selected from a single bond or a substituted or unsubstituted group consisting of phenyl, biphenyl, naphthyl, phenanthrenyl, spirofluorenyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, triphenylene, 9,9-dimethylfluorenyl, and 9,9-diphenylfluorenyl, or a combination thereof. EA is selected from a triazine derivative, a cyano derivative, or a phosphorus oxide derivative, or a combination thereof.

[0062] Furthermore, the EA is preferably And Ar9 and Ar 10 Independently selected from the following substituted or unsubstituted groups: phenyl, naphthyl, benzonaphthyl, biphenyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, fluorenyl, spirofluorene, triphenylene, phenanthrenyl or phenanthrenyl derivatives.

[0063] In some preferred embodiments, the organic compound represented by Formula III is represented by any one of the following structural formulas 85 to 183:

[0064]

[0065]

[0066]

[0067]

[0068] In formulas 85 to 183, Ar 10 Selected from the following groups:

[0069]

[0070] In some more preferred embodiments, the organic compound represented by Formula III is the following compound:

[0071]

[0072] The basic core group of the present application is combined with a specific electron-deficient group so that when the organic compound represented by Formula III is used in an electron transport material, the operating voltage of the device can be significantly reduced, and the current efficiency and life of the device can be improved.

[0073] In some embodiments, in Formula I, Ar is a group At this time, the structural formula of the organic compound is shown in Formula IV: In Formula IV, L3 is selected from a single bond, a substituted or unsubstituted C6-C30 arylene group, or a substituted or unsubstituted C3-C30 heteroarylene group. Ar3 is selected from a substituted or unsubstituted C6-C30 aryl group, or a substituted or unsubstituted C3-C30 heteroaryl group.

[0074] In some preferred embodiments, L3 is selected from a single bond or a substituted or unsubstituted group consisting of one or more of the following: phenyl, biphenyl, naphthyl, phenanthrenyl, spirofluorenyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, triphenylene, 9,9-dimethylfluorenyl, and 9,9-diphenylfluorenyl. Ar3 is selected from a substituted or unsubstituted group consisting of one or more of the following: phenyl, biphenyl, naphthyl, phenanthrenyl, spirofluorenyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, triphenylene, 9,9-dimethylfluorenyl, and 9,9-diphenylfluorenyl.

[0075] In some preferred embodiments, the organic compound represented by Formula IV is represented by any one of the following structural formulas:

[0076]

[0077] When the organic compound represented by Formula IV is used as the host material of the light-emitting layer, it can significantly reduce the operating voltage of the device, improve the luminous efficiency, and also extend the life of the device.

[0078] In some embodiments, the organic compound has a structural formula as shown in Formula V: In Formula V, Ar4 to Ar8 are independently selected from substituted or unsubstituted C6-C30 arylene groups and substituted or unsubstituted C3-C30 heteroarylene groups, and at least one of Ar4 to Ar8 comprises the following structural formula: In Formula VI, * represents a linking site, which may be one or more. R1 is selected from the group consisting of a zero, substituted or unsubstituted linear or branched C1-C60 alkyl group, a substituted or unsubstituted C3-C60 cycloalkyl group, a substituted or unsubstituted C1-C60 heteroalkyl group, a substituted or unsubstituted C1-C60 heterocycloalkyl group, a substituted or unsubstituted C6-C60 aryl group, or a substituted or unsubstituted C3-C60 heteroaryl group. X is selected from O, S, N, CR2R3, wherein: R2 and R3 are independently selected from hydrogen, substituted or unsubstituted linear or branched C1-C60 alkyl, substituted or unsubstituted C3-C60 cycloalkyl, substituted or unsubstituted C1-C60 heteroalkyl, substituted or unsubstituted C1-C60 heterocycloalkyl, substituted or unsubstituted C6-C60 aryl, or substituted or unsubstituted C3-C60 heteroaryl, or R2 and R3 are bonded to form a ring.

[0079] In some preferred embodiments, Ar4 to Ar8 are independently selected from the following substituted or unsubstituted groups: phenyl, biphenyl, naphthyl, phenanthrenyl, spirofluorenyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, triphenylene, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, or a combination thereof.

[0080] In some more preferred embodiments, the organic compound represented by Formula V is represented by any one of the following structural formulas D-1 to D-14:

[0081]

[0082] When the organic compound represented by Formula V is used as a doping material for a light-emitting layer, it can significantly reduce the operating voltage of the device, improve the luminous efficiency, and extend the life of the device.

[0083] Another aspect of the present application provides an organic layer, which includes any one of the aforementioned organic compounds. Any one of the aforementioned organic compounds and the organic layer can be used in an organic electroluminescent device.

[0084] The present application also provides an organic electroluminescent device comprising a first electrode, a second electrode, and the aforementioned organic layer. As an example, the first electrode is an anode, the second electrode is a cathode, and the cathode can be one or more layers. The organic layer is located between the first and second electrodes. The organic layer can be a single layer or a multilayer tandem structure comprising two or more organic layers. The organic layer can be 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.

[0085] In some specific embodiments, the structure of the organic electroluminescent device can be selected from one of the following:

[0086] (1) An organic electroluminescent device includes an anode, a hole injection layer, a first hole transport layer, a light-emitting layer, a first electron transport layer, and a cathode stacked in sequence, i.e., anode / hole injection layer / first hole transport layer / light-emitting layer / first electron transport layer / cathode. The device structure will be expressed in this simplified manner below.

[0087] (2) Anode / hole injection layer / second hole transport layer / first hole transport layer / light-emitting layer / first electron transport layer / cathode.

[0088] (3) Anode / hole injection layer / second hole transport layer / first hole transport layer / light-emitting layer / first electron transport layer / second electron transport layer / cathode.

[0089] (4) Anode / hole injection layer / second hole transport layer / first hole transport layer / light-emitting layer / first electron transport layer / second electron transport layer / electron injection layer / cathode.

[0090] (5) Anode / hole injection layer / second hole transport layer / first hole transport layer / light-emitting layer / first electron transport layer / second electron transport layer / multilayer cathode.

[0091] (6) Anode / hole injection layer / first hole transport layer / first light-emitting layer / carrier generation layer / first hole transport layer / second light-emitting layer / first electron transport layer / cathode.

[0092] (7) Anode / hole injection layer / first hole transport layer / first light-emitting layer / carrier generation layer / first hole transport layer / second light-emitting layer / first electron transport layer / second electron transport layer / cathode.

[0093] (8) Anode / hole injection layer / second hole transport layer / first hole transport layer / first light-emitting layer / carrier generation layer / first hole transport layer / second light-emitting layer / first electron transport layer / cathode.

[0094] (9) Anode / hole injection layer / second hole transport layer / first hole transport layer / first light-emitting layer / carrier generation layer / first hole transport layer / second light-emitting layer / first electron transport layer / second electron transport layer / cathode.

[0095] (10) Anode / hole injection layer / hole transport layer / electron blocking layer / light-emitting layer / electron transport layer / electron injection layer / cathode.

[0096] (11) Anode / hole injection layer / first hole transport layer / second hole transport layer / light-emitting layer / hole blocking layer / electron transport layer / cathode.

[0097] (12) Anode / hole injection layer / hole transport layer / electron blocking layer / light-emitting layer / electron transport layer / cathode.

[0098] (13) Anode / hole injection layer / hole transport layer / electron blocking layer / light-emitting layer / hole blocking layer / electron transport layer / cathode.

[0099] The light emission direction of the organic electroluminescent device can be emitted from the anode side or the cathode side. In some specific embodiments, if the light emission direction is the cathode side, it is necessary to add a cover layer on the cathode side. The specific structure is as follows:

[0100] 1) Anode / hole injection layer / first hole transport layer / light-emitting layer / first electron transport layer / cathode / covering layer.

[0101] 2) Anode / hole injection layer / second hole transport layer / first hole transport layer / light-emitting layer / first electron transport layer / cathode / covering layer.

[0102] 3) Anode / hole injection layer / second hole transport layer / first hole transport layer / light-emitting layer / first electron transport layer / second electron transport layer / cathode / covering layer.

[0103] 4) Anode / hole injection layer / second hole transport layer / first hole transport layer / light-emitting layer / first electron transport layer / second electron transport layer / electron injection layer / cathode / covering layer.

[0104] 5) Anode / hole injection layer / second hole transport layer / first hole transport layer / light-emitting layer / first electron transport layer / second electron transport layer / multilayer cathode / covering layer.

[0105] 6) Anode / hole injection layer / first hole transport layer / first light-emitting layer / carrier generation layer / first hole transport layer / second light-emitting layer / first electron transport layer / cathode / covering layer.

[0106] 7) Anode / hole injection layer / first hole transport layer / first light-emitting layer / carrier generation layer / first hole transport layer / second light-emitting layer / first electron transport layer / second electron transport layer / cathode / covering layer.

[0107] 8) Anode / hole injection layer / second hole transport layer / first hole transport layer / first light-emitting layer / carrier generation layer / first hole transport layer / second light-emitting layer / first electron transport layer / cathode / covering layer.

[0108] 9) Anode / hole injection layer / second hole transport layer / first hole transport layer / first light-emitting layer / carrier generation layer / first hole transport layer / second light-emitting layer / first electron transport layer / second electron transport layer / cathode / covering layer.

[0109] 10) Anode / hole injection layer / hole transport layer / electron blocking layer / light-emitting layer / electron transport layer / electron injection layer / cathode / covering layer.

[0110] 11) Anode / hole injection layer / first hole transport layer / second hole transport layer / light-emitting layer / hole blocking layer / electron transport layer / cathode / covering layer.

[0111] 12) Anode / hole injection layer / hole transport layer / electron blocking layer / light-emitting layer / electron transport layer / cathode / covering layer.

[0112] 13) Anode / hole injection layer / hole transport layer / electron blocking layer / light-emitting layer / hole blocking layer / electron transport layer / cathode / covering layer.

[0113] Some specific functional layers in the organic electroluminescent device are described below.

[0114] Substrate:

[0115] The substrate is typically located below the anode and can be made of plastic or glass, and can be rigid or flexible. The substrate has a driver unit that drives the corresponding pixel to emit light.

[0116] anode:

[0117] Organic EL (Organic Electro-Luminescence) components typically require the anode to have good conductivity, a flat surface, and be resistant to cracks. They also have certain requirements for the work function, primarily to ensure that it matches the hole injection layer and maximizes the hole injection effect.

[0118] When top emission is used (light emitting from the cathode side), the anode uses a metal compound with a work function of 4.2eV or more, such as indium tin oxide alloy, tin oxide, indium zinc oxide, gold, silver, platinum, copper, carbon nanotubes, carbon nanowires, graphene, etc. The thickness is 10nm to 200nm, preferably 10nm to 50nm. A reflective electrode is set below the anode (near the substrate end). The reflective electrode is generally made of metal or metal alloy, such as silver metal, copper metal, aluminum metal, gold metal, or alloys of these metals with other metals. The reflective electrode has a high reflectivity, which is required to be above 90%. The thickness is usually used in the range of 100nm to 500nm, preferably in the range of 80nm to 150nm.

[0119] When using a bottom emission method (light emitting from the cathode substrate side), the anode is made of a metal compound with a work function of 4.2 eV or higher, such as indium tin oxide alloy, tin oxide, indium zinc oxide, gold, silver, platinum, copper, carbon nanotubes, carbon nanowires, graphene, etc. The thickness is 10 nm to 1 μm, preferably 50 nm to 200 nm.

[0120] The anode can be produced by forming an electrode material into a thin film by a method such as vapor deposition, sputtering, or coating.

[0121] Hole injection layer:

[0122] The thickness of the hole injection layer is generally 3nm to 20nm. The hole injection layer uses a mixture of P-type material and hole transport material. The purpose of using P-type material is to accept holes from the anode and transfer them to the hole transport material. The weight proportion of P-type material in the hole injection layer is generally 0.5% to 10%. When the weight proportion is 0.5% to 3%, the absolute value of the difference between the lowest unoccupied molecular orbital (LUMO) energy level of the P-type material and the highest occupied molecular orbital (HOMO) energy level of the HTL material shall not exceed 0.3eV. When the weight proportion is 3% to 5%, the absolute value of the difference between the lowest unoccupied molecular orbital (LUMO) energy level of the P-type material and the highest occupied molecular orbital (HOMO) energy level of the HTL material shall not exceed 0.5eV. When the weight proportion is 5% to 10%, the absolute value of the difference between the lowest unoccupied molecular orbital (LUMO) energy level of the P-type material and the highest occupied molecular orbital (HOMO) energy level of the HTL material shall not exceed 1eV.

[0123] The P-type material can be a metal oxide, such as molybdenum oxide, vanadium oxide, tungsten oxide, etc.; it can also be an organic material, such as 4,4',4"-((1E,1'E,1"E)-cyclopropane-1,2,3-trimethylenetris(cyanoformylidene))tris(2,3,5,6-tetrafluorobenzyl) (PD1, CAS No.: 1224447-88-4), tetracyanoquinodimethane (TCNQ), 2,3,5,6-tetrafluoro-tetracyano-1,4-benzoquinodimethane (F4-TCNQ), 2,3,6,7,10,11-hexacyano-1,4,5,8,9,12-hexaazatriphenylene (HAT-CN), and is not limited thereto. The hole transport material used in combination with the P-type material can be selected from the material of the second hole transport layer and can be the same as or different from the material of the second hole transport layer.

[0124] Second hole transport layer:

[0125] The second hole transport layer is typically 40nm to 150nm thick and typically uses compounds containing aromatic amines, either monoamines or polyamines. The hole transport material must have high hole mobility, reduce driving voltage, and a glass transition temperature exceeding 100°C to avoid crystallization at high temperatures.

[0126] First hole transport layer:

[0127] The thickness of the first hole transport layer is generally 3nm to 220nm. When there is no second hole transport layer, the thickness of the first hole transport layer is generally 40nm to 150nm; when there is a second hole transport layer, the thickness of the first hole transport layer is generally 3nm to 120nm. Generally, red light, green light, blue light, yellow light, etc. need to be adjusted in thickness according to the "microcavity effect", and the thickness selection is also different. Taking the top-emitting light-emitting device as an example, the formula for the microcavity is as follows:

[0128] where n i and d i Respectively represent the refractive index coefficient and thickness of the i-th layer, m is an integer, which is the modulus of the microcavity, and is commonly taken as 1 or 2; θ1 and θ2 represent the phase shift generated by light at the anode interface and cathode interface, respectively.

[0129] Red light, green light, blue light or other colors of light have different wavelengths, so each color has its optimal thickness. Taking the modulus of 2 as an example, when red light is present, when there is no second hole transport layer, the thickness of the first hole transport layer is generally 160nm~220nm; when there is a second hole transport layer, the thickness of the first hole transport layer is generally 8nm~120nm. When green light is present, when there is no second hole transport layer, the thickness of the first hole transport layer is generally 100nm~180nm; when there is a second hole transport layer, the thickness of the first hole transport layer is generally 30nm~70nm. When blue light is present, when there is no second hole transport layer, the thickness of the first hole transport layer is generally 80nm~130nm; when there is a second hole transport layer, the thickness of the first hole transport layer is generally 3nm~30nm. When other colors are selected, there will be different optimal "microcavity adjustment thicknesses".

[0130] Electron blocking layer:

[0131] The electron blocking layer can have both hole transport and electron blocking functions. At the same time, the higher triplet excitation energy level of the electron blocking layer can lock excitons generated in the light-emitting layer in the light-emitting layer, thereby improving the luminous efficiency of the device.

[0132] Luminous layer:

[0133] The materials of the light-emitting layer generally include a host material and a guest dopant material. The content of the host material is greater than that of the guest dopant material. Optionally, the mass percentage of the guest dopant material in the light-emitting layer is 1% to 20%.

[0134] The guest dopant material used as the luminescent material may include a phosphorescent or fluorescent material or a thermally activated delayed fluorescent material. Red, green, and blue light can be selected from the above three types of guest dopant materials. For example, the guest dopant material for the luminescent layer corresponding to the red luminescent unit and the luminescent layer corresponding to the green luminescent unit is a phosphorescent material, while the guest dopant material for the luminescent layer corresponding to the blue luminescent unit is a fluorescent material.

[0135] Or for example, the guest doping material of the light-emitting layer corresponding to the light-emitting unit with red light emission color and the light-emitting layer corresponding to the light-emitting unit with green light emission color is a phosphorescent material, and the guest doping material of the light-emitting layer corresponding to the light-emitting unit with blue light emission color is a phosphorescent material.

[0136] Or for example, the guest doping material of the light-emitting layer corresponding to the light-emitting unit with red light-emitting color and the light-emitting layer corresponding to the light-emitting unit with green light-emitting color is a thermally activated delayed fluorescent material, and the guest doping material of the light-emitting layer corresponding to the light-emitting unit with blue light-emitting color is a fluorescent material.

[0137] Or for example, the guest doping material of the light-emitting layer corresponding to the light-emitting unit with red light-emitting color and the light-emitting layer corresponding to the light-emitting unit with green light-emitting color is a thermally activated delayed fluorescent material, and the guest doping material of the light-emitting layer corresponding to the light-emitting unit with blue light-emitting color is a phosphorescent material.

[0138] In order to reduce the power consumption of the organic light-emitting display panel in the organic electroluminescent device, the guest doping material can be selected to have excellent luminescence performance. Taking the top-emitting device as an example, the red light-emitting unit can be selected to have a luminous brightness of 1000 cd / m 2 The current efficiency is greater than 30cd / A, and the luminous unit with green luminous color has a luminous brightness of 6000cd / m 2 The current efficiency is greater than 100cd / A, and the light-emitting unit with a fluorescent blue light color has a light brightness of 1000cd / m 2 The current efficiency is greater than 5cd / A as the standard, and the appropriate guest doping material is selected. The luminous color of the luminescent unit is phosphorescent blue and the luminous brightness is 1000cd / m 2 The current efficiency is greater than 10cd / A. When the current efficiency is higher, the power consumption can be reduced.

[0139] As the light-emitting host material, one light-emitting host material or two light-emitting host materials can be selected.

[0140] Hole blocking layer:

[0141] To enhance the balance between hole and electron concentrations, a hole-blocking layer is inserted to balance carrier concentrations and prevent exciton quenching. Typically, the hole-blocking layer is located between the light-emitting layer and the electron-transporting layer. The hole-blocking layer material must meet requirements such as high stability, good film-forming properties, and a high maximum molecular orbital.

[0142] First electron transport layer:

[0143] The thickness of the first electron transport layer can generally be 3nm to 40nm, 3nm to 10nm, 10nm to 20nm, 20nm to 30nm, 30nm to 40nm, or 20nm to 40nm. When there is no second electron transport layer, the thickness of the first electron transport layer is generally 20nm to 50nm. When a second electron transport layer is present, the thickness of the first electron transport layer is generally 40nm to 20nm. The first electron transport layer is in direct contact with the light-emitting layer. Therefore, similar to the first hole transport layer, it will also undergo electronic changes during the electron transport process, resulting in increased molecular vibration and molecular deformation. The excitons of the light-emitting layer will also interact with the polarons of the electron transport material. This interaction can easily generate active free radicals that destroy the electron transport material. The electron transport material can be a single compound or mixed with other metals or metal compounds. It can include a mixture of an organic electron transport material and a metal compound, or a mixture of an organic electron transport material and a metal.

[0144] When the organic electron transport material is mixed with a metal compound material, for example, with an alkali metal compound, an alkaline earth metal compound, or a rare earth metal compound, more specifically, with a lithium metal compound, a calcium metal compound, a magnesium metal compound, a samarium metal compound, or a ytterbium metal compound, and more specifically, with lithium 8-hydroxyquinoline, lithium fluoride, magnesium fluoride, ytterbium fluoride, or calcium fluoride. When mixed with the metal compound, the weight proportion of the organic electron transport material can be 20% to 80%, 20% to 40%, 40% to 60%, or 60% to 80%.

[0145] When the organic electron transport material is mixed with a metal, for example, with an alkali metal, an alkaline earth metal, or a rare earth metal, more specifically, with lithium metal, magnesium metal, calcium metal, ytterbium metal, samarium metal, etc., when mixed with a metal, the mass proportion of the organic electron transport material can be 80% to 99%, 80% to 89%, 89% to 99%, 80% to 85%, 85% to 90%, 90% to 95%, or 95% to 99%, etc.

[0146] Second electron transport layer:

[0147] The thickness of the second electron transport layer is generally 10 nm to 40 nm. The material of the second electron transport layer may include a mixture of an organic electron transport material and a metal compound, or a mixture of an organic electron transport material and a metal.

[0148] When the organic electron transport material is mixed with a metal compound material, for example, with an alkali metal compound, an alkaline earth metal compound, or a rare earth metal compound, more specifically, with a lithium metal compound, a calcium metal compound, a magnesium metal compound, a samarium metal compound, or a ytterbium metal compound, and more specifically, with lithium 8-hydroxyquinoline, lithium fluoride, magnesium fluoride, ytterbium fluoride, or calcium fluoride. When mixed with the metal compound, the weight proportion of the organic electron transport material can be 20% to 80%, 20% to 40%, 40% to 60%, or 60% to 80%.

[0149] When the organic electron transport material is mixed with a metal, for example, with an alkali metal, an alkaline earth metal, or a rare earth metal, more specifically, with lithium metal, magnesium metal, calcium metal, ytterbium metal, samarium metal, etc., when mixed with a metal, the mass proportion of the organic electron transport material can be 80% to 99%, 80% to 89%, 89% to 99%, 80% to 85%, 85% to 90%, 90% to 95%, or 95% to 99%, etc.

[0150] Charge generation layer:

[0151] When using a single-layer light-emitting device, holes and electrons are injected from the anode and cathode, respectively, eliminating the need for a charge generation layer. When using a dual-layer or multi-layer light-emitting device, a charge generation layer is required between the light-emitting layers to achieve charge generation, injection, and transport. The charge generation layer is located between the two light-emitting layers and is typically composed of a P / N-type dual-layer material. The P-type material is selected from the hole-injection materials mentioned above, and the N-type material is a mixture of an organic electron transport material doped with a metal. The organic electron transport layer material is selected from the second electron transport layer mentioned above, and the metal is selected from alkali metals, alkaline earth metals, and rare earth metals, with lithium, magnesium, calcium, ytterbium, and samarium being more specific examples. When the organic electron transport material is mixed with the metal, the weight proportion of the organic electron transport material can range from 80% to 99%, 80% to 89%, 89% to 99%, 80% to 85%, 85% to 90%, 90% to 95%, or 95% to 99%, etc.

[0152] cathode:

[0153] The cathode requires a material with good electrical conductivity and surface flatness. To improve electron injection, materials with a low work function are generally selected. The cathode material can be a single-layer cathode, or a double-layer or multi-layer cathode, typically made of a metal or metal alloy. For a single-layer cathode, silver, copper, aluminum, gold, or alloys of these metals with other metals, such as rare earth metals, alkali metals, and alkaline earth metals, can be used. Examples include magnesium-indium alloys, magnesium-aluminum alloys, aluminum-potassium alloys, aluminum-scandium-potassium alloys, magnesium-silver alloys, silver-ytterbium alloys, and silver-samarium alloys. If a double-layer cathode is used, the cathode layer closer to the light-emitting layer can be made of alkali metals, alkaline earth metals, or rare earth metals, such as lithium, calcium, magnesium, and ytterbium, to enhance electron injection. The cathode layer farther from the light-emitting layer, primarily to enhance conductivity, can typically be made of silver, copper, aluminum, or gold, or alloys of these metals with other metals, such as rare earth metals, alkali metals, and alkaline earth metals. Examples include magnesium-indium alloys, magnesium-aluminum alloys, aluminum-potassium alloys, aluminum-scandium-potassium alloys, magnesium-silver alloys, silver-ytterbium alloys, and silver-samarium alloys. The cathode can also be formed as a thin film by methods such as evaporation and sputtering.

[0154] When light comes out from the anode side, the cathode is required to be opaque, and a cathode thicker than 100nm can be evaporated. When light comes out from the cathode side, the cathode is required to be transparent, with a transmittance greater than 40% and a thickness of 10nm to 20nm.

[0155] Covering:

[0156] The refractive index n and absorption coefficient of the single-layer cover layer need to meet the following conditions:

[0157] The refractive index between the wavelengths of 450 and 650 nm is n(450-650 nm)>1.8, and the extinction coefficient between the wavelengths of 450 and 650 nm is below 0.1; the extinction coefficient at 380 nm is greater than 0.2; the difference between the refractive index of 450 nm and the refractive index of 530 nm is n(450 nm)-n(530 nm)<0.5, more preferably n(450 nm)-n(530 nm)<0.3; the difference between the refractive index of 510 nm and the refractive index of 620 nm is n(510 nm)-n(620 nm)<0.4, more preferably the difference between the refractive index of 510 nm and the refractive index of 620 nm is n(510 nm)-n(620 nm)<0.2.

[0158] Materials that can meet the requirements of the cover layer for the refractive index n can further achieve high luminous efficiency of the device, while at the same time achieving more balanced light extraction efficiency and viewing angles for red, green, and blue light.

[0159] In some specific embodiments, the thickness of the covering layer is 50nm to 90nm, for example, 50nm, 55nm, 57nm, 59nm, 62nm, 64nm, 67nm, 68nm, 70nm, 75nm, 77nm, 79nm, 80nm, 82nm, 85nm, 88nm, 90nm, etc.

[0160] After the covering layer is formed on the side of the semi-transparent cathode of the OLED display panel away from the substrate, the light transmittance of the stacked layer formed by the covering layer and the semi-transparent cathode between 450nm and 650nm can be ≥65%, for example, 68%, 69%, 73%, 77%, 79%, 83%, 88%, 93%, etc.

[0161] When two covering layers are used, the refractive index n and absorption coefficient need to meet the following conditions:

[0162] The covering layer close to the cathode side (the first covering layer) has a refractive index n450~650nm<1.8 between 450 and 650nm, and an extinction coefficient between 450 and 650nm below 0.1; the maximum coefficient at any wavelength between 250nm and 350nm is greater than 0.3, and optimally greater than 0.6.

[0163] The covering layer away from the cathode side (the second covering layer) has a refractive index n450~650nm>1.8 between wavelengths of 450~650nm, and an extinction coefficient between wavelengths of 450~650nm is below 0.1; the extinction coefficient at 380nm is greater than 0.1, and more preferably greater than 0.2.

[0164] The difference between the refractive index at 450 nm and the refractive index at 530 nm, n(450 nm)-n(530 nm), is less than 0.5, and more preferably, the difference between the refractive index at 450 nm and the refractive index at 530 nm, n(450 nm)-n(530 nm), is less than 0.3;

[0165] The difference between the refractive index at 510 nm and the refractive index at 620 nm is n(510 nm)-n(620 nm)<0.4, and more preferably, the difference between the refractive index at 450 nm and the refractive index at 530 nm is n(450 nm)-n(530 nm)<0.2.

[0166] The total thickness of the double-layer covering layer is 50nm to 90nm, for example: 50nm, 55nm, 57nm, 59nm, 62nm, 64nm, 67nm, 68nm, 70nm, 75nm, 77nm, 79nm, 80nm, 82nm, 85nm, 88nm, 90nm, etc.

[0167] The thickness of the covering layer close to the cathode side (first covering layer) is 5nm to 40nm, for example: 5nm, 7nm, 10nm, 12nm, 15nm, 18nm, 20nm, 22nm, 25nm, 27nm, 30nm, 32nm, 34nm, 36nm, 38nm, 40nm, etc.

[0168] The thickness of the covering layer away from the cathode side (the second covering layer) is 35nm to 85nm, for example: 35nm, 40nm, 43nm, 45nm, 48nm, 50nm, 55nm, 57nm, 59nm, 62nm, 64nm, 67nm, 68nm, 70nm, 75nm, 77nm, 79nm, 80nm, 82nm, 85nm, etc.

[0169] On the other hand, the present application further provides a display or lighting device, comprising the above-mentioned organic electroluminescent device.

[0170] The organic compounds of the present application can be synthesized using known methods. For example, cross-coupling reactions using transition metals such as nickel and palladium, or CC or CN coupling reactions using transition metals such as magnesium and zinc, can also be used. Preferably, the Suzuki or Buchwald reaction is used, which has mild reaction conditions and excellent selectivity for various functional groups.

[0171] In some embodiments, the reactants are heated in an organic solvent in the presence of a cross-coupling catalyst (catalytic amount) in an inert atmosphere, and the reaction is stirred under reflux. After the desired reaction time, a reaction system is obtained, cooled, and water is added. The precipitated solid is washed and then vacuum-dried to obtain a crude product. The obtained crude product is refined (including but not limited to silica gel column chromatography) to obtain an organic compound product.

[0172] The technical solutions of the present application will be described clearly and completely below in conjunction with the specific examples of the present application. Unless otherwise specified, the reagents and raw materials used can be purchased through commercial channels. The experimental methods for which specific conditions are not specified in the following specific examples are generally determined in accordance with national standards. If there are no corresponding national standards, then the methods are based on general international standards, conventional methods and conditions, or the conditions recommended by the manufacturer, or selected according to the product specifications. Unless otherwise specified, all parts are parts by weight and all percentages are percentages by weight. The following examples only illustrate some of the organic compounds and their preparation methods of the present application and should not be regarded as limitations on the organic compounds and their preparation methods of the present application.

[0173] The starting materials and solvents used in the following examples were purchased from Shanghai Titan Technology Co., Ltd. Commonly used OLED intermediates and other products were purchased from domestic OLED intermediate manufacturers. Various palladium catalysts and ligands were purchased from Shaanxi Ruike New Materials Co., Ltd. HPLC data were measured using a Waters Corporation UPLC ultra-high performance liquid chromatograph. 1 HNMR data were measured using a 400 MHz nuclear magnetic resonance spectrometer (manufactured by Bruker, Germany). LC-MS (liquid chromatography-mass spectrometry) was performed on a UPLC+SQD2 instrument from Waters Corporation.

[0174] Example 1

[0175] Synthesis of compound H-1

[0176]

[0177] (1) Synthesis of intermediate H-1-1

[0178] Under an argon atmosphere, a reaction vessel was charged with 38.9 g (100 mmol) of organic compound H-1-A, 16.9 g (100 mmol) of organic compound H-1-B, 23.4 g (240 mmol) of sodium tert-butoxide, 575 mg (1 mmol%) of bisdibenzylideneacetone palladium, 348 mg (1.2 mmol%) of tri-tert-butylphosphine tetrafluoroborate, and 1000 mL of xylene. The mixture was heated and stirred at 140°C for 15 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 a large amount of water and dried under vacuum. The crude product was purified by silica gel column chromatography (eluent: ethyl acetate / hexane) to obtain 40.6 g of organic compound H-1-1 with an HPLC purity of 99.6% and a yield of 85%. LC MS: M / Z 477.21 (M+).

[0179] (2) Synthesis of Compound H-1

[0180] The synthesis of intermediate H-1-1 was the same as that of intermediate H-1-1, except that the starting materials were replaced with H-1-1 and H-1-C. LC MS: M / Z 629.27 (M+). HPLC purity: 99.9%, yield: 79%.

[0181] Examples 2 to 14

[0182] The reaction raw materials and products of Examples 2 to 14 can be referred to as shown in Table 1, and the specific synthesis method can be referred to Example 1.

[0183] Table 1 Reaction materials and products of Examples 2 to 14

[0184]

[0185]

[0186] Example 15 Synthesis of Compound E-1

[0187] Under an argon atmosphere, a reaction vessel was charged with 38.9 g (101 mmol) of organic compound E-1-A, 27.7 g (100 mmol) of organic compound E-1-B, 787 mg (1 mmol%) of XPhos Pd G3, 50 mL (300 mmol) of 1.5 M potassium phosphate, and 1000 mL of tetrahydrofuran (THF). The mixture was stirred under reflux for 12 hours. After cooling to room temperature, 800 mL of water was added. A large amount of solid precipitated and was filtered. The filter cake was washed three times with water and dried under vacuum. The crude product was purified by silica gel column chromatography (eluent: ethyl acetate / hexane) to obtain 54.1 g of organic compound E-1, a yield of 75%, and a HPLC purity of 99.9%. LC MS: M / Z 643.29 (M+).

[0188] Examples 16 to 28

[0189] The reaction raw materials and products of Examples 16 to 28 can be referred to as shown in Table 2, and the specific synthesis method can be referred to Example 15.

[0190] Table 2 Reaction materials and products of Examples 16 to 28

[0191]

[0192]

[0193] Example 29

[0194] Synthesis of compound B-1

[0195]

[0196] (1) Synthesis of intermediate B-1-1

[0197] Under an argon atmosphere, a reaction vessel was charged with 33.6 g (100 mmol) of compound B-1-A, 17.2 g (100 mmol) of compound B-1-B, 1.4 g (2 mmol) of Pd(PPh3)2Cl2, 200 mL (300 mmol) of 1.5 M sodium carbonate solution, and 1000 mL of ethylene glycol dimethyl ether (DME). The mixture was heated and stirred at 80°C for 5 hours. After cooling to room temperature, 800 mL of water was added. A large amount of solid precipitated and was filtered. The filter cake was washed three times with water and dried under vacuum. The crude product was purified by silica gel column chromatography (eluent: ethyl acetate / hexane) to obtain 14.0 g of compound B-1-1, with a yield of 42% and an HPLC purity of 99.3%. LC MS: M / Z 382.04 (M+).

[0198] (2) Synthesis of Compound B-1

[0199] The synthesis of intermediate B-1-1 was the same as that of intermediate B-1-1, except that the starting materials were replaced with B-1-1 and B-1-C. LC MS: M / Z 612.25 (M+). HPLC purity: 99.9%, yield: 72%.

[0200] Examples 30 to 42

[0201] The reaction raw materials and products of Examples 30 to 42 can be referred to as shown in Table 3, and the specific synthesis method can be referred to Example 29.

[0202] Table 3 Reaction materials and products of Examples 30 to 42

[0203]

[0204]

[0205] Example 43

[0206] Synthesis of compound D-1

[0207]

[0208] Under an argon atmosphere, a reaction vessel was charged with 69.4 g (101 mmol) of compound D-1-A, 21.3 g (100 mmol) of compound D-1-B, 787 mg (1 mmol%) of XPhos Pd G3, 50 mL (300 mmol) of 1.5 M potassium phosphate, and 1000 mL of tetrahydrofuran (THF). The mixture was stirred under reflux for 12 hours. After cooling to room temperature, 800 mL of water was added. A large amount of solid precipitated and was filtered. The filter cake was washed three times with water and dried under vacuum. The crude product was purified by silica gel column chromatography (eluent: ethyl acetate / hexane) to obtain 75.4 g of compound D-1, a yield of 65%, with an HPLC purity of 99.9%. LC-MS: M / Z 1159.56 (M+).

[0209] Examples 44 to 56

[0210] The reaction raw materials and products of Examples 44 to 56 can be referred to as shown in Table 4, and the specific synthesis method can be referred to Example 43.

[0211] Table 4 Reaction materials and products of Examples 44 to 56

[0212]

[0213]

[0214]

[0215] Preparation of organic electroluminescent devices

[0216] The organic electroluminescent device is prepared using the compound of the present application as a hole transport material. In addition to the compound of the present application, other compounds involved are as follows:

[0217]

[0218]

[0219] Device Example 1

[0220] refer to Figure 1 The method for preparing an organic electroluminescent device according to the present device embodiment includes:

[0221] (1) A transparent anode ITO film layer (thickness 150 nm) is formed on a glass substrate 101 to obtain a first electrode as the anode 102 .

[0222] (2) A mixture of compound T-1 and compound T-2 was deposited on the surface of the anode 102 by vacuum evaporation as the hole injection layer 103 , with a mixing ratio of 3:97 (mass ratio) and a thickness of 10 nm.

[0223] (3) Compound T-2 was evaporated onto the hole injection layer 103 to a thickness of 100 nm to obtain the first hole transport layer 104 .

[0224] (4) Compound H-1 of the present application was evaporated to a thickness of 10 nm on the first hole transport layer 104 to obtain a second hole transport layer 105 .

[0225] (5) On the second hole transport layer 105 , compound T-3 and compound T-4 were co-evaporated at a mass ratio of 95:5 to form an organic light-emitting layer 106 with a thickness of 40 nm.

[0226] (6) Compound T-5 was sequentially evaporated on the organic light-emitting layer 106 to form a hole blocking layer 107 (thickness 10 nm), and compound T-6 and LiQ with a mixing ratio of 4:6 (mass ratio) were formed into an electron transport layer 108 (thickness 30 nm).

[0227] (7) Magnesium (Mg) and silver (Ag) are mixed at a deposition rate of 1:9 and vacuum evaporated on the electron transport layer 108 to serve as the second electrode 109, thereby completing the manufacture of the organic electroluminescent device.

[0228] Device Examples 2 to 14

[0229] The organic electroluminescent device was manufactured by the same method as in Device Example 1, except that Compounds H-2 to H-14 were used instead of Compound H-1 when forming the second hole transport layer 105 .

[0230] Device Comparison Examples 1-2, 3A

[0231] An organic electroluminescent device was prepared by the same method as in Device Example 1, except that Compound HT-1, Compound HT-2, and Compound HT-3 were used instead of Compound H-1 when forming the second hole transport layer 105 .

[0232] The organic electroluminescent device prepared above was tested by a computer-controlled Keithley 2400 test system at a test current of 10 mA / cm 2 , the operating voltage and current efficiency are calculated.

[0233] The LT95 device lifetime under dark conditions was measured using a Flustar lifetime measurement system equipped with a power supply and a photodiode as a detection unit. The LT95 device lifetime is the time it takes for the luminance at initial brightness to decrease to 95% of its initial brightness. A longer time indicates a longer device lifetime.

[0234] The devices of each group of device embodiments and device comparative examples were produced and tested in the same batch. The operating voltage, current efficiency, and LT95 life of the device of device comparative example 1 were all recorded as 1. The ratios of the corresponding indicators of device embodiments 1 to 10, device comparative example 2, and device comparative example 3A to device comparative example 1 were calculated to obtain the relative operating voltage, relative current efficiency, and relative life as shown in Table 5.

[0235] Table 5 Test results of device embodiments 1 to 14 and device comparative examples 1 to 2

[0236] Device Second hole transport layer Relative working voltage Relative current efficiency Relative lifespan Device Comparative Example 1 HT-1 1 1 1 Device Comparative Example 2 HT-2 1.079 1.037 1.461 Device Comparative Example 3A HT-3 1.056 1.065 1.561 Device Example 1 Compound H-1 0.946 1.201 1.852 Device Example 2 Compound H-2 0.955 1.168 1.803 Device Example 3 Compound H-3 0.956 1.173 1.902 Device Example 4 Compound H-4 0.940 1.189 1.816 Device Example 5 Compound H-5 0.953 1.174 1.773 Device Example 6 Compound H-6 0.950 1.158 1.782 Device Example 7 Compound H-7 0.962 1.169 1.923 Device Example 8 Compound H-8 0.942 1.192 1.802 Device Example 9 Compound H-9 0.957 1.175 1.987 Device Example 10 Compound H-10 0.932 1.181 1.894 Device Example 11 Compound H-11 0.945 1.192 1.696 Device Example 12 Compound H-12 0.957 1.174 1.796 Device Example 13 Compound H-13 0.963 1.166 1.876 Device Example 14 Compound H-14 0.958 1.187 1.916

[0237] Compared with the devices formed by using the compounds used as hole transport materials in device comparative examples 1 to 2 and 3A, the devices made by using the compounds of the present application as hole transport materials have lower operating voltage, higher current efficiency and longer life.

[0238] The following organic electroluminescent devices are prepared using the compounds of the present application as electron transport materials. In addition to the compounds of the present application, other compounds involved are as follows:

[0239]

[0240] Device Example 15

[0241] refer to Figure 2 The method for preparing an organic electroluminescent device according to the present device embodiment includes:

[0242] (1) A transparent anode ITO (indium tin oxide) glass substrate (with a surface resistivity of 10 Ω / sq) was ultrasonically cleaned with acetone, ethanol, and distilled water in sequence, and then treated with ozone plasma for 15 minutes. The transparent anode ITO (indium tin oxide) glass substrate included an ITO glass substrate 100 and an anode 110 located on the ITO glass substrate 100.

[0243] (2) After installing the transparent anode ITO glass substrate 100 on the substrate holder of the vacuum vapor deposition equipment, control the system pressure at 10 -6 Then, 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 on the transparent anode ITO glass substrate to form a hole injection layer 120, a hole transport layer 130 and an electron blocking layer 140 respectively.

[0244] (3) A light-emitting layer (EML) 150 with a thickness of 40 nm was evaporated on the TCTA. The composition of the light-emitting layer 150 included RH-1 and RD in a mass ratio of 94:6.

[0245] (4) Compound E-1 of the present application was evaporated on the light-emitting layer 150 to a thickness of 30 nm to serve as the electron transport layer (ETL) 160 .

[0246] (5) LiF was evaporated to a thickness of 1 nm on the electron transport layer 160 to form the electron injection layer 170 .

[0247] (6) Al with a thickness of 80 nm was evaporated on the electron injection layer 170 to form the cathode 180 , and the device was encapsulated using a glass encapsulation cap 190 .

[0248] Device Examples 16 to 28

[0249] An organic electroluminescent device was prepared by the same method as in Device Example 15, except that Compounds E-2 to E-14 were used instead of Compound E-1 when forming the electron transport layer 160 .

[0250] Device Comparative Example 3

[0251] An organic electroluminescent device was manufactured using the same method as in Device Example 15, except that Compound ETL-1 was used instead of Compound E-1 when forming the electron transport layer 160 .

[0252] The organic electroluminescent devices produced in Device Examples 15-28 and Comparative Example 3 were tested using the same testing methods as described above to determine the operating voltage, current efficiency, and LT95. The devices of Device Examples 15-28 and Comparative Example 3 were produced and tested in the same batch. The operating voltage, current efficiency, and lifetime of the device in Comparative Example 3 were all recorded as 1. The ratios of the corresponding indicators for Device Examples 15-28 to Comparative Example 3 were calculated to obtain the relative operating voltage, relative current efficiency, and relative lifetime shown in Table 6.

[0253] Table 5 Test results of device examples 15 to 28 and device comparative example 3

[0254]

[0255]

[0256] According to the results in Table 5, compared with the organic electroluminescent device prepared in Comparative Example 3, the operating voltage of the organic electroluminescent device prepared using the compound of the present application as the electron transport material is reduced, the current efficiency is significantly improved, and the device life is also improved.

[0257] The following organic electroluminescent devices are prepared using the compounds of the present application as blue light host materials. In addition to the compounds of the present application, other compounds involved are as follows:

[0258]

[0259] Device Example 29

[0260] refer to Figure 3 The method for preparing an organic electroluminescent device according to the present device embodiment includes:

[0261] (1) A transparent anode ITO film layer (thickness 150 nm) is formed on a glass substrate 10 to obtain a first electrode as the anode 11 .

[0262] (2) Compound F4-TCNQ was evaporated on the surface of the anode 11 by vacuum evaporation to form a hole injection layer 12 with a thickness of 10 nm, and compound NPB was vacuum evaporated on the hole injection layer 12 to form a hole transport layer (HTL) 13 with a thickness of 110 nm.

[0263] (3) Compound EB-01 was evaporated to a thickness of 10 nm on the hole injection layer 13 to obtain the electron blocking layer 14 .

[0264] (4) Compound B-1 was used as the main component on the electron blocking layer 14 and BD-1 was co-doped at a film thickness ratio of 100:3 to form a light-emitting layer (EML) 15 with a thickness of 10 nm.

[0265] (5) ET-01 and LiQ were evaporated on the light-emitting layer 15 at a film thickness ratio of 1:1 to form an electron transport layer (ETL) 16 with a thickness of 30 nm, and Yb was evaporated on the electron transport layer 16 to form an electron injection layer (EIL) 17 with a thickness of 15 angstroms.

[0266] (6) Magnesium (Mg) and silver (Ag) were vacuum-deposited on the electron injection layer 17 at a film thickness ratio of 1:9 to form a cathode 18 with a thickness of 11 nm.

[0267] (7) CP-1 with a thickness of 65 nm was evaporated on the cathode 18 as an organic cover layer (CPL) 19 to complete the preparation of the organic electroluminescent device.

[0268] Device Examples 30 to 42

[0269] An organic electroluminescent device was prepared by the same method as in Device Example 29, except that Compound B-2 to B-14 were used instead of Compound B-1 when forming the light-emitting layer 15 .

[0270] Device Comparative Examples 4-5

[0271] An organic electroluminescent device was prepared by the same method as in Device Example 29, except that Compound BH-1 and Compound BH-2 were used instead of Compound B-1 when forming the light-emitting layer 15 .

[0272] The organic electroluminescent devices produced in Examples 29-42 and Comparative Examples 4-5 were tested using the same testing methods as described above to determine their operating voltage, current efficiency, and LT95. The devices in Examples 29-42 and Comparative Examples 4-5 were produced and tested in the same batch. The operating voltage, current efficiency, and lifetime of the device in Comparative Example 4 were all recorded as 1. The ratios of the corresponding indicators for Examples 29-42 and Comparative Example 5 were calculated to obtain the relative operating voltage, relative current efficiency, and relative lifetime shown in Table 6. Color purity was tested using existing color purity testing methods.

[0273] Table 6 Test results of device examples 29 to 42 and device comparative examples 4 to 5

[0274]

[0275]

[0276] According to the results in Table 6, compared with the commercial products used in device comparison examples 4 to 5, the devices formed using the compounds used in device examples 29 to 42 as the main material have lower operating voltage, higher current efficiency and longer device life, while also showing color purity comparable to that of the commercial products.

[0277] The following organic electroluminescent devices are prepared using the compounds of the present application as blue light doping materials. In addition to the compounds of the present application, other compounds involved are as follows:

[0278]

[0279] Device Example 43

[0280] refer to Figure 4 The method for preparing an organic electroluminescent device according to the present device embodiment includes:

[0281] (1) A 15Ω / cm 2 An ITO (anode 2) glass substrate 1 (Corning Incorporated) was cut into a size of 50 mm x 50 mm x 0.75 mm, and cleaned using acetone, isopropyl alcohol, and pure water, each subjected to ultrasonic treatment for 15 minutes, followed by ultraviolet irradiation and ozone exposure for 30 minutes. The resulting glass substrate 1 was then mounted on a vacuum deposition apparatus.

[0282] (2) G-1 and G-2 were vacuum deposited on the anode 2 at a mass ratio of 3:97 to form a hole injection layer 3 with a thickness of 10 nm, and G-1 and G-2 were vacuum deposited on the hole injection layer 3 at a mass ratio of 5:1 to form a hole transport layer 4 with a thickness of 120 nm.

[0283] (3) Compound BH-3 (host) and compound D-1 (dopant) were vacuum-deposited on the hole transport layer 4 at a weight ratio of 98:2 to form a light-emitting layer 5 having a thickness of 20 nm.

[0284] (4) G-4 and LiQ were vacuum deposited on the light-emitting layer 5 at a mass ratio of 4:6 to form an electron transport layer 6 with a thickness of 40 nm, and KI and Yb were vacuum deposited on the electron transport layer 6 at a weight ratio of 8:2 to form an electron injection layer 7 with a thickness of 1 nm. Ag and Mg were vacuum deposited on the electron injection layer 7 at a weight ratio of 90:10 to form a cathode 8 with a thickness of 10 nm, thereby completing the preparation of the organic electroluminescent device.

[0285] Device Examples 44 to 56

[0286] An organic electroluminescent device was prepared by the same method as in Device Example 43, except that Compound D-2 to D-14 were used instead of Compound D-1 when forming the light-emitting layer 5.

[0287] Device Comparative Examples 6-7

[0288] An organic electroluminescent device was prepared by the same method as in Device Example 43, except that Compound BD-2 and Compound BD-3 were used instead of Compound D-1 when forming the light-emitting layer 5 .

[0289] The organic electroluminescent devices prepared in Examples 43 to 56 and Comparative Examples 6 to 7 were tested using the same testing methods as described above to determine the operating voltage, current efficiency, and LT95. The devices in Examples 43 to 56 and Comparative Examples 6 to 7 were produced and tested in the same batch. The operating voltage, current efficiency, and lifetime of the device in Comparative Example 6 were all recorded as 1. The ratios of the corresponding indicators for Examples 43 to 56 and Comparative Example 7 were calculated to obtain the relative operating voltage, relative current efficiency, and relative lifetime shown in Table 7.

[0290] Table 7 Test results of device examples 43 to 56 and device comparative examples 6 to 7

[0291] Example Doping materials Relative working voltage Relative current efficiency Relative lifespan Comparative Example 6 BD-2:BH-3=2:98 1 1 1 Comparative Example 7 BD-3:BH-3=2:98 0.968 1.269 1.305 Example 43 D-1:BH-3=2:98 0.943 1.425 1.523 Example 44 D-2:BH-3=2:98 0.925 1.446 1.615 Example 45 D-3:BH-3=2:98 0.914 1.396 1.743 Example 46 D-4:BH-3=2:98 0.945 1.479 1.672 Example 47 D-5:BH-3=2:98 0.936 1.510 1.581 Example 48 D-6:BH-3=2:98 0.928 1.487 1.498 Example 49 D-7:BH-3=2:98 0.941 1.495 1.517 Example 50 D-8:BH-3=2:98 0.937 1.398 1.479 Example 51 D-9:BH-3=2:98 0.926 1.412 1.432 Example 52 D-10:BH-3=2:98 0.938 1.437 1.513

[0292] According to Table 7, the operating voltage of the devices formed by using the compounds used in device Examples 43 to 56 as doping materials is reduced, and the current efficiency and life are improved compared with the commercial products used in device Comparative Examples 6 to 7.

[0293] The above description of the embodiments is intended to facilitate understanding and application of the present application by those skilled in the art. It will be apparent that those skilled in the art can readily make various modifications to these embodiments and apply the general principles described herein to other embodiments without expending any creative effort. Therefore, the present application is not limited to the embodiments described herein, and improvements and modifications made by those skilled in the art based on the disclosure of this application without departing from the scope and spirit of this application are within the scope of this application.

Claims

1. An organic compound, characterized in that Its structural formula is shown in Formula I: In the formula I, Ar is selected from substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl; R1 is selected from none, substituted or unsubstituted linear or branched C1-C60 alkyl, substituted or unsubstituted C3-C60 cycloalkyl, substituted or unsubstituted C1-C60 heteroalkyl, substituted or unsubstituted C1-C60 heterocycloalkyl, substituted or unsubstituted C6-C60 aryl, or substituted or unsubstituted C3-C60 heteroaryl; X is selected from O, S, N, CR2R3, wherein: R2 and R3 are independently selected from hydrogen, substituted or unsubstituted linear or branched C1-C60 alkyl, substituted or unsubstituted C3-C60 cycloalkyl, substituted or unsubstituted C1-C60 heteroalkyl, substituted or unsubstituted C1-C60 heterocycloalkyl, substituted or unsubstituted C6-C60 aryl, or substituted or unsubstituted C3-C60 heteroaryl, or R2 and R3 are bonded to form a ring.

2. The organic compound according to claim 1, characterized in that The Ar is a group The structural formula of the organic compound is shown in Formula II: In the formula II, L1 is selected from a single bond, a substituted or unsubstituted C6-C30 arylene group, or a substituted or unsubstituted C3-C30 heteroarylene group; Ar1 and Ar2 are independently selected from substituted or unsubstituted C6-C30 arylene groups, or substituted or unsubstituted C3-C30 heteroarylene groups; n is an integer from 0 to 4.

3. The organic compound according to claim 2, characterized in that The L1 is selected from a single bond or a substituted or unsubstituted group: phenyl, biphenyl, naphthyl, phenanthrenyl, spirofluorenyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, triphenylene, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, or a combination thereof; Ar1 and Ar2 are independently selected from the following substituted or unsubstituted groups: phenyl, biphenyl, naphthyl, phenanthrenyl, spirofluorenyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, triphenylene, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, or a combination thereof.

4. The organic compound according to claim 3, characterized in that The organic compound represented by Formula II is represented by any one of the following structural formulas: In Formulae 1 to 84, Ar2 is selected from the following groups:

5. The organic compound according to claim 4, characterized in that The organic compound represented by formula II is the following compound:

6. The organic compound according to claim 1, characterized in that The Ar is a group L2-EA; the structural formula of the organic compound is shown in Formula III: In the formula III, L2 is selected from a single bond, a substituted or unsubstituted C6-C30 arylene group, or a substituted or unsubstituted C3-C30 heteroarylene group; EA is selected from one or a combination of cyano derivatives, trifluoromethyl, fluoroaryl, fluoroalkyl, nitrogen-containing aromatic groups, and phosphorus oxide derivatives.

7. The organic compound according to claim 6, characterized in that The L2 is selected from a single bond or a substituted or unsubstituted group: phenyl, biphenyl, naphthyl, phenanthrenyl, spirofluorenyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, triphenylene, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, one or more combinations thereof; the EA is selected from a triazine derivative, a cyano derivative, and a phosphorus oxide derivative, one or more combinations thereof.

8. The organic compound according to claim 7, characterized in that The EA is And Ar9 and Ar 10 Independently selected from the following substituted or unsubstituted groups: phenyl, naphthyl, benzonaphthyl, biphenyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, fluorenyl, spirofluorene, triphenylene, phenanthrenyl or phenanthrenyl derivatives.

9. The organic compound according to claim 8, characterized in that The organic compound represented by Formula III is represented by any one of the following structural formulas: In formulas 85 to 183, Ar 10 Selected from the following groups:

10. The organic compound according to claim 9, characterized in that The organic compound represented by formula III is the following compound:

11. The organic compound according to claim 1, characterized in that Ar is a group The structural formula of the organic compound is shown in Formula IV: In the formula IV, L3 is selected from a single bond, a substituted or unsubstituted C6-C30 arylene group, or a substituted or unsubstituted C3-C30 heteroarylene group; Ar3 is selected from substituted or unsubstituted C6-C30 aryl and substituted or unsubstituted C3-C30 heteroaryl.

12. The organic compound according to claim 11, characterized in that The L3 is selected from a single bond or a substituted or unsubstituted group: phenyl, biphenyl, naphthyl, phenanthrenyl, spirofluorenyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, triphenylene, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, or a combination thereof; The Ar3 is selected from the following substituted or unsubstituted groups: phenyl, biphenyl, naphthyl, phenanthrenyl, spirofluorenyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, triphenylene, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, or a combination thereof.

13. The organic compound according to claim 12, characterized in that The organic compound represented by Formula IV is represented by any one of the following structural formulas B-1 to B-14:

14. An organic compound, characterized in that Its structural formula is shown in Formula V: In Formula V, Ar4 to Ar8 are independently selected from substituted or unsubstituted C6-C30 arylene groups and substituted or unsubstituted C3-C30 heteroarylene groups, and at least one of Ar4 to Ar8 comprises a structural formula of Formula VI; and in Formula VI: * is a connection site, and there is one or more connection sites; R1 is selected from none, substituted or unsubstituted linear or branched C1-C60 alkyl, substituted or unsubstituted C3-C60 cycloalkyl, substituted or unsubstituted C1-C60 heteroalkyl, substituted or unsubstituted C1-C60 heterocycloalkyl, substituted or unsubstituted C6-C60 aryl, or substituted or unsubstituted C3-C60 heteroaryl; X is selected from O, S, N, CR2R3, wherein: R2 and R3 are independently selected from hydrogen, substituted or unsubstituted linear or branched C1-C60 alkyl, substituted or unsubstituted C3-C60 cycloalkyl, substituted or unsubstituted C1-C60 heteroalkyl, substituted or unsubstituted C1-C60 heterocycloalkyl, substituted or unsubstituted C6-C60 aryl, or substituted or unsubstituted C3-C60 heteroaryl, or R2 and R3 are bonded to form a ring.

15. The organic compound according to claim 14, characterized in that Ar4 to Ar8 are independently selected from the following substituted or unsubstituted groups: phenyl, biphenyl, naphthyl, phenanthrenyl, spirofluorenyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, triphenylene, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, or a combination thereof.

16. The organic compound according to claim 15, wherein the organic compound represented by formula V is represented by any one of the following structural formulas D-1 to D-14:

17. An organic layer, characterized in that The organic compound comprises the organic compound according to any one of claims 1 to 16.

18. Use of the organic compound according to any one of claims 1 to 16 and / or the organic layer according to claim 17 in an organic electroluminescent device.

19. An organic electroluminescent device, characterized in that: The device comprises a first electrode, a second electrode and the organic layer according to claim 17, wherein the organic layer is 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.

20. A display or lighting device, characterized in that: The organic electroluminescent device according to claim 19 is included.

Images