Organic compound, and electronic element and electronic device using the same

Abstract

The present application relates to an organic compound, and an electronic element and an electronic device using the same. The organic compound of the present application has a structure represented by Formula 1, and application of the organic compound represented by Formula 1 to an organic electroluminescence device can significantly improve the performance of the device.

Description

Technical Field

[0001] This application relates to the field of organic electroluminescence technology, specifically to an organic compound and electronic components and devices using the same. Background Technology

[0002] With the development of electronic technology and the advancement of materials science, the application range of electronic components used to achieve electroluminescence or photoelectric conversion is becoming increasingly wide. Taking organic electroluminescent devices (OLEDs) as an example, they typically include a cathode and an anode arranged opposite each other, and a functional layer disposed between the cathode and the anode. This functional layer consists of multiple organic or inorganic film layers, and generally includes an energy conversion layer, a hole transport layer located between the energy conversion layer and the anode, and an electron transport layer located between the energy conversion layer and the cathode. When a voltage is applied to the anode and cathode, an electric field is generated between the two electrodes. Under the action of the electric field, electrons on the cathode side move towards the electroluminescent layer, and holes on the anode side also move towards the light-emitting layer. Electrons and holes combine in the electroluminescent layer to form excitons. The excitons are in an excited state and release energy outward, thereby causing the electroluminescent layer to emit light.

[0003] OLED technology has been widely used in the display field due to its advantages such as high color saturation, wide viewing angle, and low power consumption. In recent years, to obtain high-efficiency organic electroluminescent devices, technologies related to phosphorescence emission utilizing triplet energy or fluorescence emission utilizing triplet-triplet annihilation (TTA) where singlet excitons are generated through collisions of triplet excitons are developed. Thermally activated delayed fluorescence (TADF) materials utilizing delayed fluorescence phenomena are also under development. However, the color performance of OLED screens is highly dependent on the performance of the luminescent materials, especially red luminescent materials, as red is key to achieving a high color gamut and natural display effect.

[0004] In OLED devices, dopant materials, used as the organic light-emitting layer, affect the device's luminous efficiency, lifetime, and color purity. Currently, traditional red dopant materials still have many limitations in performance, such as insufficient luminous efficiency, limited lifetime, and poor color purity. These problems hinder further breakthroughs in OLED display technology. With the development of flexible displays and high dynamic range imaging technologies, there is an urgent need to develop novel red dopant materials that combine narrow-band emission, high exciton utilization, and excellent stability to overcome the barriers to synergistic optimization of red light efficiency, color gamut, and lifetime, and to promote the industrialization of next-generation self-emissive displays. Summary of the Invention

[0005] The purpose of this application is to provide an organic compound and electronic components and devices using the same, wherein using the organic compound in an organic electroluminescent device can improve the device's performance.

[0006] A first aspect of this application provides an organic compound having the structure shown in Formula 1:

[0007]

[0008] Among them, Z1, Z2, Z3, and Z4 may be the same or different, and each is independently selected from C(R). a R b ), N(R c ), O or S;

[0009] p1 is the number of Z1s. p1 is 0 or 1. When p1 is 0, it means that Z1 does not exist.

[0010] p2 is the number of Z2s. p2 is 0 or 1. When p2 is 0, it means that Z2 does not exist.

[0011] p3 is the number of Z3s. p3 is 0 or 1. When p3 is 0, it means that Z3 does not exist.

[0012] p4 is the number of Z4s. p4 is 0 or 1. When p4 is 0, it means that Z4 does not exist.

[0013] R a R b and R c They may be the same or different, and each is independently selected from alkyl groups having 1 to 10 carbon atoms, deuterated alkyl groups having 1 to 10 carbon atoms, haloalkyl groups having 1 to 10 carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, and substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms.

[0014] R1, R2, R3, R4, R5, and R6 may be the same or different, and each is independently selected from hydrogen, deuterium, halogen groups, cyano, alkyl groups with 1 to 10 carbon atoms, deuterated alkyl groups with 1 to 10 carbon atoms, haloalkyl groups with 1 to 10 carbon atoms, trialkylsilyl groups with 3 to 12 carbon atoms, triphenylsilyl groups, cycloalkyl groups with 3 to 10 carbon atoms, substituted or unsubstituted aryl groups with 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups with 3 to 30 carbon atoms, or... The structure shown;

[0015] Ar a Ar b Ar1, Ar2, Ar3 and Ar4 may be the same or different, and each is independently selected from substituted or unsubstituted aryl groups with 6 to 30 carbon atoms, or substituted or unsubstituted heteroaryl groups with 3 to 30 carbon atoms;

[0016] R a R b R c Ar a Arb The substituents in Ar1, Ar2, Ar3, Ar4, R1, R2, R3, R4, R5, and R6 may be the same or different, and each is independently selected from deuterium, halogen groups, cyano, alkyl with 1 to 10 carbon atoms, deuterated alkyl with 1 to 10 carbon atoms, haloalkyl with 1 to 10 carbon atoms, trialkylsilyl with 3 to 12 carbon atoms, triphenylsilyl, cycloalkyl with 3 to 10 carbon atoms, aryl with 6 to 20 carbon atoms, deuterated aryl with 6 to 20 carbon atoms, or heteroaryl with 3 to 20 carbon atoms;

[0017] n1 is the number of R1s, and n1 is selected from 1, 2, 3 or 4. When n1 is greater than 1, any two R1s are the same or different.

[0018] n2 is the number of R2, which can be selected from 1, 2, 3 or 4. When n2 is greater than 1, any two R2 are the same or different.

[0019] n3 is the number of R3s, and n1 is selected from 1, 2, 3 or 4. When n3 is greater than 1, any two R3s are the same or different.

[0020] n4 is the number of R4s, and n2 is selected from 1, 2, 3 or 4. When n4 is greater than 1, any two R4s are the same or different.

[0021] n5 is the number of R5s, which can be selected from 1, 2, 3 or 4. When n5 is greater than 1, any two R5s can be the same or different.

[0022] n6 is the number of R6s, and n2 is selected from 1, 2, 3 or 4. When n6 is greater than 1, any two R6s are the same or different.

[0023] A second aspect of this application provides an electronic component including an anode and a cathode disposed opposite to each other, and a functional layer disposed between the anode and the cathode; the functional layer comprising the aforementioned organic compound.

[0024] A third aspect of this application provides an electronic device including the electronic components described in the second aspect of this application.

[0025] This application provides for These compounds, based on a polycyclic fused framework of alternating boron and nitrogen (BN) atoms, construct a multiple resonance system by bridging BNB and NBN units through a central BN single bond. The push-pull electron effect of boron and nitrogen atoms enables atomic-level spatial separation of HOMO / LUMO orbitals, resulting in narrow-band emission with both high color purity and thermally activated delayed fluorescence (TADF) characteristics. Simultaneously, the single-bond connection imparts local flexibility to the molecule, breaking the rigid planar structure and reducing concentration quenching caused by π-π stacking, while maintaining the rigidity of the main framework to ensure radiative transition efficiency. Therefore, using these compounds as doping materials for organic light-emitting layers can improve exciton generation and utilization, thereby enhancing the luminous efficiency and lifetime of the device.

[0026] Other features and advantages of this application will be described in detail in the following detailed description section. Attached Figure Description

[0027] The accompanying drawings are provided to further understand this application and form part of the specification. They are used together with the following detailed description to explain this application, but do not constitute a limitation thereof.

[0028] Figure 1 This is a schematic diagram of the structure of an organic electroluminescent device according to one embodiment of this application.

[0029] Figure 2 This is a schematic diagram of a first electronic device according to one embodiment of this application.

[0030] Explanation of reference numerals in the attached figures

[0031] 100, Anode; 200, Cathode; 300, Functional layer; 310, Hole injection layer; 320, Hole transport layer; 321, First hole transport layer; 322, Second hole transport layer; 330, Organic light-emitting layer; 340, Electron transport layer; 350, Electron injection layer; 400, Electronic device Detailed Implementation

[0032] Exemplary embodiments will now be described more fully with reference to the accompanying drawings. However, exemplary embodiments can be implemented in many forms and should not be construed as limited to the examples set forth herein; rather, these embodiments are provided so that this application will be more comprehensive and complete, and will fully convey the concept of exemplary embodiments to those skilled in the art. The described features, structures, or characteristics may be combined in any suitable manner in one or more embodiments. In the following description, numerous specific details are provided to give a full understanding of embodiments of this application.

[0033] In a first aspect, this application provides an organic compound having the structure shown in Formula 1:

[0034]

[0035] Among them, Z1, Z2, Z3, and Z4 may be the same or different, and each is independently selected from C(R). a R b ), N(R c ), O or S;

[0036] p1 is the number of Z1s. p1 is 0 or 1. When p1 is 0, it means that Z1 does not exist.

[0037] p2 is the number of Z2s. p2 is 0 or 1. When p2 is 0, it means that Z2 does not exist.

[0038] p3 is the number of Z3s. p3 is 0 or 1. When p3 is 0, it means that Z3 does not exist.

[0039] p4 is the number of Z4s. p4 is 0 or 1. When p4 is 0, it means that Z4 does not exist.

[0040] R a R b and R c They may be the same or different, and each is independently selected from alkyl groups having 1 to 10 carbon atoms, deuterated alkyl groups having 1 to 10 carbon atoms, haloalkyl groups having 1 to 10 carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, and substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms.

[0041] R1, R2, R3, R4, R5, and R6 may be the same or different, and each is independently selected from hydrogen, deuterium, halogen groups, cyano, alkyl groups with 1 to 10 carbon atoms, deuterated alkyl groups with 1 to 10 carbon atoms, haloalkyl groups with 1 to 10 carbon atoms, trialkylsilyl groups with 3 to 12 carbon atoms, triphenylsilyl groups, cycloalkyl groups with 3 to 10 carbon atoms, substituted or unsubstituted aryl groups with 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups with 3 to 30 carbon atoms, or... The structure shown;

[0042] Ar a Ar b Ar1, Ar2, Ar3 and Ar4 may be the same or different, and each is independently selected from substituted or unsubstituted aryl groups with 6 to 30 carbon atoms, or substituted or unsubstituted heteroaryl groups with 3 to 30 carbon atoms;

[0043] R a R b R c Ar a Ar bThe substituents in Ar1, Ar2, Ar3, Ar4, R1, R2, R3, R4, R5, and R6 may be the same or different, and each is independently selected from deuterium, halogen groups, cyano, alkyl with 1 to 10 carbon atoms, deuterated alkyl with 1 to 10 carbon atoms, haloalkyl with 1 to 10 carbon atoms, trialkylsilyl with 3 to 12 carbon atoms, triphenylsilyl, cycloalkyl with 3 to 10 carbon atoms, aryl with 6 to 20 carbon atoms, deuterated aryl with 6 to 20 carbon atoms, or heteroaryl with 3 to 20 carbon atoms;

[0044] n1 is the number of R1s, and n1 is selected from 1, 2, 3 or 4. When n1 is greater than 1, any two R1s are the same or different.

[0045] n2 is the number of R2, which can be selected from 1, 2, 3 or 4. When n2 is greater than 1, any two R2 are the same or different.

[0046] n3 is the number of R3s, and n1 is selected from 1, 2, 3 or 4. When n3 is greater than 1, any two R3s are the same or different.

[0047] n4 is the number of R4s, and n2 is selected from 1, 2, 3 or 4. When n4 is greater than 1, any two R4s are the same or different.

[0048] n5 is the number of R5s, which can be selected from 1, 2, 3 or 4. When n5 is greater than 1, any two R5s can be the same or different.

[0049] n6 is the number of R6s, and n2 is selected from 1, 2, 3 or 4. When n6 is greater than 1, any two R6s are the same or different.

[0050] In this application, the descriptive phrases "each independently selected from" and "separately independently selected from" are interchangeable and should be interpreted broadly. They can mean either that the specific options expressed by the same symbol in different groups do not affect each other, or that the specific options expressed by the same symbol in the same group do not affect each other. For example, " In this formula, each q is independently 0, 1, 2 or 3, and each R is independently selected from hydrogen, deuterium, fluorine or chlorine. The meaning is as follows: Formula Q-1 indicates that there are q substituents R on the benzene ring. Each R can be the same or different, and the options of each R do not affect each other. Formula Q-2 indicates that there are q substituents R on each benzene ring of biphenyl. The number q of substituents R on the two benzene rings can be the same or different, and each R can be the same or different. The options of each R do not affect each other.

[0051] In this application, the term "substituted or unsubstituted" means that the functional group described after the term may or may not have substituents (hereinafter, for ease of description, substituents are collectively referred to as Rc). For example, "substituted or unsubstituted aryl" refers to an aryl group having a substituent Rc or an unsubstituted aryl group. The aforementioned substituent, i.e., Rc, can be, for example, deuterium, halogen group, cyano, alkyl, trialkylsilyl, haloalkyl, deuteralkyl, aryl, deuterated aryl, heteroaryl, etc.

[0052] In this application, the number of carbon atoms in substituted or unsubstituted functional groups refers to the total number of carbon atoms. For example, if L1 is a substituted arylene with 12 carbon atoms, then the total number of carbon atoms in the arylene and its substituents is 12.

[0053] In this application, aryl refers to any optional functional group or substituent derived from an aromatic carbon ring. An aryl group can be a monocyclic aryl (e.g., phenyl) or a polycyclic aryl; in other words, an aryl group can be a monocyclic aryl, a fused-ring aryl, two or more monocyclic aryl groups linked by carbon-carbon bonds, a monocyclic aryl and a fused-ring aryl linked by carbon-carbon bonds, or two or more fused-ring aryl groups linked by carbon-carbon bonds. That is, unless otherwise stated, two or more aromatic groups linked by carbon-carbon bonds can also be considered aryl groups in this application. Fused-ring aryl groups may include, for example, bicyclic fused aryl (e.g., naphthyl), tricyclic fused aryl (e.g., phenanthrene, fluorenyl, anthracene), etc. The aryl group does not contain heteroatoms such as B, N, O, S, P, Se, and Si. For example, in this application, biphenyl, terphenyl, etc., are aryl groups. Examples of aryl groups may include, but are not limited to, phenyl, naphthyl, fluorenyl, anthraceneyl, phenanthryl, biphenyl, terphenyl, benzo[9,10]phenanthryl, pyrene, benzofluoranthraceneyl, etc. In this application, the term "arylene" refers to a divalent group formed by the further loss of a hydrogen atom from an aryl group.

[0054] In this application, the substituted aryl group can be one or more hydrogen atoms of the aryl group that are substituted by groups such as deuterium, halogen groups, cyano, aryl, deuterated aryl, heteroaryl, trialkylsilyl, alkyl, haloalkyl, deuterated alkyl, etc. Specific examples of heteroaryl-substituted aryl groups include, but are not limited to, dibenzofuranyl-substituted phenyl, dibenzothiophene-substituted phenyl, pyridine-substituted phenyl, etc. It should be understood that the number of carbon atoms in the substituted aryl group refers to the total number of carbon atoms of the aryl group and the substituents on the aryl group. For example, a substituted aryl group with 18 carbon atoms means that the total number of carbon atoms of the aryl group and the substituents is 18.

[0055] In this application, a heteroaryl group refers to a monovalent aromatic ring or its derivative containing at least one heteroatom. The heteroatom can be one or more of B, O, N, P, Si, Se, and S. A heteroaryl group can be a monocyclic heteroaryl group or a polycyclic heteroaryl group. In other words, a heteroaryl group can be a single aromatic ring system or a system of multiple aromatic rings connected by carbon-carbon bonds in a conjugated manner. Any aromatic ring system can be a single aromatic monocyclic ring or a fused aromatic ring. For example, heteroaryl groups may include, but are not limited to, thiopheneyl, furanyl, pyrrolyl, imidazolyl, thiazolyl, oxazolyl, oxadiazolyl, triazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, acridineyl, pyridazinyl, quinolinyl, quinazolinyl, quinoxazinyl, phenoxazinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, isoquinolinyl, indolyl, carbazoleyl, benzoxazolyl, benzoimidazolyl, benzothiazolyl, benzocarbazoleyl, benzothiaphenyl, dibenzothiaphenyl, thiaphenothiaphenyl, benzofuranyl, phenanthrololinyl, isoxazolyl, thiadiazolyl, phenthiaazinyl, silfluorenyl, dibenzofuranyl, and N-phenylcarbazoleyl, N-pyridylcarbazoleyl, N-methylcarbazoleyl, etc. In this application, the term "hybrid aryl" refers to a divalent group formed by the further loss of a hydrogen atom by a heteroaryl group.

[0056] In this application, the substituted heteroaryl group can be one or more hydrogen atoms of the heteroaryl group that are replaced by groups such as deuterium, halogen groups, cyano, aryl, heteroaryl, trialkylsilyl, alkyl, haloalkyl, deuteryl, triphenylsilyl, etc. Specific examples of aryl-substituted heteroaryl groups include, but are not limited to, phenyl-substituted dibenzofuranyl, phenyl-substituted dibenzothiophenyl, phenyl-substituted pyridyl, etc. It should be understood that the number of carbon atoms in the substituted heteroaryl group refers to the total number of carbon atoms of the heteroaryl group and the substituents on the heteroaryl group.

[0057] In this application, terphenyl includes

[0058] In this application, the aryl group used as a substituent can have 6 to 20 carbon atoms, for example, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, or 20 carbon atoms. Specific examples of aryl groups used as substituents include, but are not limited to, phenyl, biphenyl, naphthyl, and anthraceneyl groups. base.

[0059] In this application, the number of carbon atoms in the heteroaryl group used as a substituent can be 3 to 20, for example, the number of carbon atoms can be 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, or 20. Specific examples of heteroaryl groups used as substituents include, but are not limited to, pyridinyl, pyrimidinyl, carbazolyl, dibenzofuranyl, dibenzothiophenyl, quinolinyl, quinazolinyl, quinoxalinyl, and isoquinolinyl.

[0060] In this application, the number of carbon atoms in alkyl groups having 1 to 10 carbon atoms can be, for example, 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10. Specific examples of alkyl groups include, but are not limited to, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl, neopentyl, n-hexyl, n-heptyl, n-octyl, 2-ethylhexyl, nonyl, decyl, 3,7-dimethyloctyl, etc.

[0061] In this application, deuterated aryl refers to an aryl group containing at least one deuterated substituent. Specific embodiments of deuterated aryl include, but are not limited to, pentadeuterated phenyl, pentadeuterated biphenyl, and nonadeuterated biphenyl.

[0062] The “hydrogen” mentioned in this invention includes its isotopes, such as protium (P), deuterium (D), and tritium (T).

[0063] In this application, the halogen group may be, for example, fluorine, chlorine, bromine, or iodine.

[0064] In this application, specific examples of trialkylsilyl groups include, but are not limited to, trimethylsilyl, triethylsilyl, etc.

[0065] In this application, specific examples of alkyl halogens include, but are not limited to, trifluoromethyl.

[0066] In this application, specific examples of deuterated alkyl groups include, but are not limited to, trideuterated methyl groups.

[0067] In this application, specific examples of cycloalkyl groups include, but are not limited to, cyclopropane, cyclopentane, cyclohexane, or adamantane.

[0068] In this application, a non-positioned linker bond refers to a single bond extending from the ring system. This indicates that one end of the linker can connect to any position in the ring system it traverses, and the other end connects to the rest of the compound molecule. For example, as shown in equation (f) below, the naphthyl group represented by equation (f) is connected to other positions in the molecule through two non-positional linkers that traverse the bicyclic ring. This means that any possible connection mode shown in equations (f-1) to (f-10) is included.

[0069]

[0070] For another example, as shown in equation (X'), the dibenzofuran group represented by equation (X') is connected to other positions in the molecule via a non-positional linker extending from the middle of one side of the benzene ring. This means that any possible connection mode shown in equations (X'-1) to (X'-4) is included.

[0071]

[0072] In some embodiments of this application, the organic compound has the structure shown in Formula 1-1, Formula 1-2, Formula 1-3, Formula 1-4, Formula 1-5, Formula 1-6, Formula 1-7, Formula 1-8 or Formula 1-9:

[0073]

[0074]

[0075] In Equations 1-1 to 1-9, the definitions of Z1, Z2, Z3, Z4, Ar1, Ar2, Ar3, Ar4, R1, R2, R3, R4, R5, R6, n1, n2, n3, n4, n5, or n6 are the same as in Equation 1.

[0076] In some embodiments of this application, R a R b and R c They may be the same or different, and each independently selected from alkyl groups having 1 to 5 carbon atoms, deuterated alkyl groups having 1 to 5 carbon atoms, haloalkyl groups having 1 to 5 carbon atoms, substituted or unsubstituted aryl groups having 6 to 20 carbon atoms, and substituted or unsubstituted heteroaryl groups having 12 to 20 carbon atoms. Optionally, R a R b and R c The same or different, and each independently selected from alkyl groups having 1, 2, 3, 4 or 5 carbon atoms, deuterated alkyl groups having 1, 2, 3, 4 or 5 carbon atoms, haloalkyl groups having 1, 2, 3, 4 or 5 carbon atoms, substituted or unsubstituted aryl groups having 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19 or 20 carbon atoms, and substituted or unsubstituted heteroaryl groups having 12, 13, 14, 15, 16, 17, 18, 19 or 20 carbon atoms.

[0077] In some embodiments of this application, R a R b and R cThe substituents in the group may be the same or different, and each is independently selected from deuterium, fluorine, cyano, alkyl with 1 to 5 carbon atoms, deuterated alkyl with 1 to 5 carbon atoms, haloalkyl with 1 to 5 carbon atoms, trialkylsilyl with 3 to 6 carbon atoms, cycloalkyl with 3 to 10 carbon atoms, aryl with 6 to 12 carbon atoms, deuterated aryl with 6 to 12 carbon atoms, or heteroaryl with 3 to 12 carbon atoms.

[0078] In some embodiments of this application, R a R b and R c They may be the same or different, and each is independently selected from methyl, ethyl, isopropyl, tert-butyl, trideuterated methyl, trifluoromethyl, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted phenanthrene, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted carbazolyl.

[0079] In some embodiments of this application, R a R b and R c The substituents in the group may be the same or different, and each is independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trideuterated methyl, trifluoromethyl, trimethylsilyl, phenyl, naphthyl, pentadeuterated phenyl, dibenzofuranyl, dibenzothiopheneyl or carbazoyl.

[0080] In some embodiments of this application, R a R b and R c They may be the same or different, and each is independently selected from methyl, ethyl, isopropyl, tert-butyl, trideuterated methyl, trifluoromethyl, phenyl, pentadeuterated phenyl, naphthyl, biphenyl, terphenyl, phenanthryl, dibenzofuranyl, dibenzothiophene, or carbazolyl.

[0081] In some embodiments of this application, Ar1, Ar2, Ar3, and Ar4 may be the same or different, and each is independently selected from substituted or unsubstituted aryl groups having 6 to 20 carbon atoms, or substituted or unsubstituted heteroaryl groups having 12 to 24 carbon atoms. Optionally, Ar1, Ar2, Ar3, and Ar4 may be the same or different, and each is independently selected from substituted or unsubstituted aryl groups having 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, or 20 carbon atoms, or substituted or unsubstituted heteroaryl groups having 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, or 24 carbon atoms.

[0082] In some embodiments of this application, the substituents in Ar1, Ar2, Ar3, and Ar4 may be the same or different, and each is independently selected from deuterium, fluorine, cyano, alkyl with 1 to 5 carbon atoms, deuterated alkyl with 1 to 5 carbon atoms, haloalkyl with 1 to 5 carbon atoms, trialkylsilyl with 3 to 6 carbon atoms, cycloalkyl with 3 to 10 carbon atoms, aryl with 6 to 12 carbon atoms, deuterated aryl with 6 to 12 carbon atoms, or heteroaryl with 3 to 12 carbon atoms.

[0083] In some embodiments of this application, Ar1, Ar2, Ar3, and Ar4 may be the same or different, and each is independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted phenanthyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted 9,10-dihydro-acridyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, and substituted or unsubstituted carbazoleyl.

[0084] In some embodiments of this application, the substituents in Ar1, Ar2, Ar3 and Ar4 may be the same or different, and each is independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trideuterated methyl, trifluoromethyl, trimethylsilyl, cyclopropane, cyclopentane, cyclohexane, adamantane, phenyl, pentadeuterated phenyl, dibenzofuranyl, dibenzothiopheneyl or carbazoleyl.

[0085] In some embodiments of this application, Ar1, Ar2, Ar3, and Ar4 may be the same or different, and each is independently selected from the group consisting of:

[0086]

[0087] In some embodiments of this application, Ar1, Ar2, Ar3, and Ar4 may be the same or different, and each is independently selected from the group consisting of:

[0088]

[0089]

[0090] In some embodiments of this application, R1, R2, R3, R4, R5, and R6 may be the same or different, and each is independently selected from hydrogen, deuterium, fluorine, cyano, alkyl with 1 to 5 carbon atoms, deuterated alkyl with 1 to 5 carbon atoms, haloalkyl with 1 to 5 carbon atoms, trialkylsilyl with 3 to 6 carbon atoms, triphenylsilyl, cycloalkyl with 3 to 10 carbon atoms, substituted or unsubstituted aryl with 6 to 20 carbon atoms, substituted or unsubstituted heteroaryl with 12 to 24 carbon atoms, or... The structure shown. Optionally, R1, R2, R3, R4, R5, and R6 may be the same or different, and each independently selected from hydrogen, deuterium, fluorine, cyano, alkyl with 1, 2, 3, 4, or 5 carbon atoms, deuterated alkyl with 1, 2, 3, 4, or 5 carbon atoms, haloalkyl with 1, 2, 3, 4, or 5 carbon atoms, trialkylsilyl with 3, 5, or 6 carbon atoms, triphenylsilyl, cycloalkyl with 3, 4, 5, 6, 7, 8, 9, or 10 carbon atoms, substituted or unsubstituted aryl with 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, or 20 carbon atoms, substituted or unsubstituted heteroaryl with 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, or 24 carbon atoms, or... The structure shown;

[0091] Ar a and Ar b They may be the same or different, and each is independently selected from substituted or unsubstituted aryl groups with 6 to 20 carbon atoms, or substituted or unsubstituted heteroaryl groups with 12 to 20 carbon atoms.

[0092] In some embodiments of this application, Ar a Ar b The substituents in R1, R2, R3, R4, R5, and R6 may be the same or different, and each is independently selected from deuterium, fluorine, cyano, alkyl with 1 to 5 carbon atoms, deuterated alkyl with 1 to 5 carbon atoms, haloalkyl with 1 to 5 carbon atoms, trialkylsilyl with 3 to 6 carbon atoms, cycloalkyl with 3 to 10 carbon atoms, aryl with 6 to 12 carbon atoms, deuterated aryl with 6 to 12 carbon atoms, or heteroaryl with 3 to 12 carbon atoms.

[0093] In some embodiments of this application, R1, R2, R3, R4, R5, and R6 may be the same or different, and each is independently selected from hydrogen, deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trideuterated methyl, trifluoromethyl, trimethylsilyl, triphenylsilyl, cyclopropane, cyclopentane, cyclohexane, adamantane, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted phenanthyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted 9,10-dihydro-acridyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiopheneyl, substituted or unsubstituted carbazoleyl, or the following groups:

[0094]

[0095] In some embodiments of this application, the substituents in R1, R2, R3, R4, R5, and R6 may be the same or different, and each is independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trideuterated methyl, trifluoromethyl, trimethylsilyl, cyclopropane, cyclopentane, cyclohexane, adamantane, phenyl, pentadeuterated phenyl, dibenzofuranyl, dibenzothiopheneyl, or carbazoyl.

[0096] In some embodiments of this application, R1, R2, R3, R4, R5, and R6 may be the same or different, and each is independently selected from the group consisting of hydrogen, deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trideuterated methyl, trifluoromethyl, trimethylsilyl, triphenylsilyl, cyclopropane, cyclopentane, cyclohexane, adamantane, or the following groups:

[0097]

[0098] In some embodiments of this application, R1, R2, R3, R4, R5, and R6 may be the same or different, and each is independently selected from the group consisting of hydrogen, deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trideuterated methyl, trifluoromethyl, trimethylsilyl, triphenylsilyl, cyclopropane, cyclopentane, cyclohexane, adamantane, or the following groups:

[0099]

[0100]

[0101] Specifically, the organic compound is selected from the group consisting of:

[0102]

[0103]

[0104]

[0105]

[0106] Secondly, this application provides an electronic component, including an anode and a cathode disposed opposite to each other, and a functional layer disposed between the anode and the cathode; the functional layer contains the organic compound of this application.

[0107] Optionally, the functional layer includes an organic light-emitting layer containing the organic compound described in this application.

[0108] Optionally, the organic light-emitting layer comprises a dopant material containing the organic compound described in this application.

[0109] Optionally, the electronic component is an organic electroluminescent device.

[0110] In one specific embodiment, the organic electroluminescent device is a red organic electroluminescent device.

[0111] In one embodiment, the electronic component is an organic electroluminescent device. For example... Figure 1 As shown, the organic electroluminescent device may include an anode 100, a hole transport layer 320, a first hole transport layer 321, a second hole transport layer 322, an organic light-emitting layer 330, an electron transport layer 340, and a cathode 200, which are stacked sequentially. The first hole transport layer 321 and the second hole transport layer 322 constitute the hole transport layer 320.

[0112] Optionally, the anode 100 comprises an anode material, preferably one with a high work function that facilitates hole injection into the functional layer. Specific examples of anode materials include: metals such as nickel, platinum, vanadium, chromium, copper, zinc, and gold, or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); combinations of metals and oxides such as ZnO:Al or SnO2:Sb; or conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDT), polypyrrole, and polyaniline, but are not limited thereto. A transparent electrode comprising indium tin oxide (ITO) is preferred as the anode.

[0113] Optionally, the hole transport layer 321 includes one or more hole transport materials. The hole transport material can be selected from carbazole polymers, carbazole-linked triarylamine compounds, or other types of compounds. Those skilled in the art can select these materials by referring to existing technologies. For example, the material of the hole transport layer is selected from the group consisting of the following compounds:

[0114]

[0115]

[0116] In one specific implementation, the first hole transport layer 321 is HT-28; the second hole transport layer 322 is HT-29.

[0117] Optionally, the organic light-emitting layer 330 may be composed of a single light-emitting layer material, or it may include a host material and a dopant material. Optionally, the organic light-emitting layer 330 is composed of a host material and a dopant material. Holes and electrons injected into the organic light-emitting layer 330 can recombine in the organic light-emitting layer 330 to form excitons. The excitons transfer energy to the host material, and the host material transfers energy to the dopant material, thereby enabling the dopant material to emit light.

[0118] The host material of the organic light-emitting layer 330 can be a metal chelate compound, a bis(styrene) derivative, an aromatic amine derivative, a dibenzofuran derivative, or other types of materials; this application does not impose any special restrictions on this. The host material can be a single host material or a mixture of host materials.

[0119] In one embodiment of this application, the host material of the organic light-emitting layer 330 is compound 4P-NPB. and PO-T2T

[0120] The doping material of the organic light-emitting layer 330 can be selected with reference to existing technologies, such as heterocyclic compounds, iridium(III) organometallic complexes, platinum(II) organometallic complexes, ruthenium(II) complexes, etc. In one embodiment of this application, the doping material of the organic light-emitting layer 330 is an organic compound of this application.

[0121] In one embodiment of this application, the organic light-emitting layer may further include a sensitizer. The sensitizer may include at least one organometallic compound, a heterocyclic compound, or any combination thereof. The organometallic compound may include ruthenium (Ru), palladium (Pd), rhenium (Re), osmium (Os), platinum (Pt), or any combination thereof. When the organic light-emitting layer includes a sensitizer and a dopant, high exciton energies can be transferred to the sensitizer and then to the dopant. Therefore, the deterioration of the dopant is suppressed, and thus lifetime characteristics are improved, and spectral overlap between the sensitizer and the dopant is increased, resulting in efficient (effective) energy transfer. Therefore, the radiative decay rate increases and non-radiative transitions decrease, thereby improving the luminous efficiency of the organic light-emitting device. Specific examples of the sensitizer include, but are not limited to,

[0122]

[0123]

[0124] In one embodiment of this application, the sensitizer of the organic light-emitting layer 330 is Ir(tptpy)2(acac).

[0125] Optionally, the electron transport layer 340 can be a single-layer structure or a multi-layer structure, and may include one or more electron transport materials. The electron transport materials typically include metal complexes and / or nitrogen-containing heterocyclic derivatives. The metal complexes may be selected from, for example, LiQ, Alq3, Bepq2, etc. The nitrogen-containing heterocyclic derivatives may be aromatic rings with a nitrogen-containing six- or five-membered ring skeleton, fused aromatic ring compounds with a nitrogen-containing six- or five-membered ring skeleton, etc. Specific examples include, but are not limited to, 1,10-phenanthroline compounds such as ET-15, Bphen, NBphen, DBimiBphen, and BimiBphen, or anthracene compounds, triazine compounds, or pyrimidine compounds containing heteronitrogenous aryl groups as shown below. In one embodiment of this application, the electron transport layer 340 is composed of ET-15 and LiQ.

[0126]

[0127] In this application, the cathode 200 may include a cathode material that has a small work function and facilitates electron injection into the functional layer. Specific examples of cathode materials include, but are not limited to, metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead or alloys thereof; or multilayer materials such as LiF / Al, Liq / Al, LiO2 / Al, LiF / Ca, LiF / Al, and BaF2 / Ca. Preferably, a metal electrode comprising magnesium and silver is included as the cathode.

[0128] Optionally, such as Figure 1 As shown, a hole injection layer 310 may also be disposed between the anode 100 and the hole transport layer 321 to enhance the ability to inject holes into the hole transport layer 321. The hole injection layer 310 may be selected from benzidine derivatives, starburst-like aryl amine compounds, phthalocyanine derivatives, or other materials; this application does not impose any special limitations on this. For example, the compounds contained in the hole injection layer 310 may be selected from the group consisting of the following compounds:

[0129]

[0130] In one specific embodiment of this application, the hole injection layer 310 is HT-28 and NDP-9.

[0131] Optionally, such as Figure 1 As shown, an electron injection layer 350 is further disposed between the cathode 200 and the electron transport layer 340 to enhance the ability to inject electrons into the electron transport layer 340. The electron injection layer 350 may include inorganic materials such as alkali metal sulfides and alkali metal halides, or may include complexes of alkali metals and organic materials. In one specific embodiment of this application, the electron injection layer 350 is LiQ.

[0132] A third aspect of this application provides an electronic device that includes the electronic components provided in the second aspect of this application.

[0133] According to one implementation method, such as Figure 2 As shown, the electronic device is a first electronic device 400, which includes the aforementioned organic electroluminescent device. The first electronic device 400 can be, for example, a display device, a lighting device, an optical communication device, or other types of electronic devices, such as, but not limited to, computer screens, mobile phone screens, televisions, electronic paper, emergency lighting, optical modules, etc. The synthesis method of the organic compounds in this application will be specifically described below with reference to synthesis examples, but this application is not limited thereto.

[0134] Compounds synthesized using methods not mentioned in this application are all raw material products obtained through commercial means.

[0135] 1. Synthesis of Sub-a1:

[0136]

[0137] Under a nitrogen atmosphere, RM-1 (50.0 g, 450.0 mmol), RM-2 (172.3 g, 900.0 mmol), sodium tert-butoxide (129.7 g, 1.35 mol), and 500 mL of toluene were added sequentially to a 1 L three-necked flask. The mixture was stirred and heated to 100 °C. Tris(dibenzylacetone)dipalladium (4.1 g, 4.5 mmol) and 4,5-bis(diphenylphosphine-9,9-dimethyloxanthracene) (5.2 g, 9.0 mmol) were then added, and the mixture was heated to reflux for 4 h. After the system cooled to room temperature, 300 mL of deionized water was added and the mixture was stirred for 5 minutes. The organic phase was then separated and the aqueous phase was extracted with toluene (200 mL × 3). The organic phases were combined and dried over anhydrous sodium sulfate. The solvent was removed by vacuum distillation after filtration. The crude product was purified by silica gel column chromatography using toluene / n-heptane as the mobile phase. The final product was a white solid, Sub-a1 (124.6 g, yield 83%).

[0138] The intermediates Sub-a2 and Sub-a3 shown in Table 1 were synthesized using the same method as Sub-a1. The difference was that reactant A was used instead of RM-1 and reactant B was used instead of RM-2. The main raw materials used, the intermediates synthesized, and their yields are shown in Table 1.

[0139] Table 1

[0140]

[0141] 2. Synthesis of Sub-b1:

[0142]

[0143] Under a nitrogen atmosphere, Sub-a1 (30.0 g, 90.3 mmol) was dissolved in 300 mL of tert-butylbenzene, then cooled to -40 °C, and tert-butyllithium (292.0 mL, 379.3 mmol, 1.3 M pentane solution) was added. The mixture was reacted at this temperature for 30 minutes, then heated to room temperature and reacted for another hour. After the starting material was completely consumed, BBr3 (47.5 g, 189.7 mmol) was added to the system and the mixture was reacted at room temperature for 1 hour. Then, pentamethylpiperidine (PMP, 27.9 g, 180.6 mmol) was added and the mixture was refluxed for 18 hours. Finally, RM-3 (135.5 mL, 270.9 mmol, 2 M tetrahydrofuran solution) was added to the system and the reaction was continued for 2 hours. After the system cooled to room temperature, 300 mL of deionized water was added and the mixture was stirred for 5 minutes. The organic phase was then separated and the aqueous phase was extracted with toluene (100 mL × 3). The combined organic phases were dried over anhydrous sodium sulfate, filtered, and the solvent was removed by vacuum distillation. The crude product was purified by silica gel column chromatography using toluene / n-heptane as the mobile phase, and finally, the compound Sub-b1 (11.8 g, yield 38%) was obtained as a yellow solid.

[0144] Intermediates Sub-b2 to Sub-b4, as shown in Table 2, were synthesized using the same method as Sub-b1. The difference was that reactant C was used instead of Sub-a1, and reactant D was used instead of RM-3. The main raw materials used, the intermediates synthesized, and their yields are shown in Table 2.

[0145] Table 2

[0146]

[0147]

[0148] 3. Synthesis of Sub-c1:

[0149]

[0150] Sub-b1 (11.5 g, 26.4 mmol), RM-4 (5.4 g, 26.4 mmol), and cesium carbonate (25.8 g, 79.3 mmol) were added to 100 mL of DMSO. The system was kept dry and heated to reflux for 16 hours. After the starting materials were completely consumed, the system was cooled to room temperature, 100 mL of deionized water was added, and stirring was continued for 5 minutes. The organic phase was then separated, and the aqueous phase was extracted with toluene (100 mL × 3). The combined organic phases were washed with deionized water (300 mL × 2), dried over anhydrous sodium sulfate, filtered, and the solvent was removed by vacuum distillation. The crude product was purified by silica gel column chromatography using toluene / n-heptane as the mobile phase, finally yielding compound Sub-c1 (13.6 g, yield 83%) as a yellow solid.

[0151] Intermediates Sub-c2 to Sub-c6, as shown in Table 3, were synthesized using the same method as Sub-c1, except that reactant E was used instead of Sub-b1 and reactant F was used instead of RM-4. The main raw materials used, the intermediates synthesized, and their yields are shown in Table 3.

[0152] Table 3

[0153]

[0154]

[0155] 4. Synthesis of Sub-d1:

[0156]

[0157] Under a nitrogen atmosphere, RM-5 (20.0 g, 48.9 mmol), RM-6 (16.6 g, 97.9 mmol), sodium tert-butoxide (14.1 g, 146.8 mmol), and 200 mL of toluene were added sequentially to a 500 mL three-necked flask. The mixture was heated to approximately 100 °C, and Pd2(dba)3 (0.4 g, 0.5 mmol) and Xantphos (0.6 g, 1.0 mmol) were added. The mixture was then heated to reflux and stirred until RM-6 was completely consumed. After the system temperature cooled to room temperature, 200 mL of deionized water was added and stirred for 5 minutes. The organic phase was separated, and the aqueous phase was extracted with toluene (100 mL × 3). The resulting organic phases were combined and dried over anhydrous sodium sulfate. After filtration, the solvent was removed by vacuum distillation. The crude product was purified by silica gel column chromatography using toluene / dichloromethane as the eluent, finally yielding Sub-d1 (20.4 g, yield 85%) as a white solid.

[0158] The intermediates Sub-d2 to Sub-d13 listed in Table 4 were synthesized using the same method as Sub-d1, except that reactant G was used instead of RM-5 and reactant H was used instead of RM-6. The main raw materials used, the intermediates synthesized, and their yields are shown in Table 4.

[0159] Table 4

[0160]

[0161]

[0162]

[0163] 5. Synthesis of Sub-e1:

[0164]

[0165] Under a nitrogen atmosphere, Sub-d1 (100.0 g, 203.5 mmol), boron tribromide (509.8 g, 2.0 mol), and 1 L of o-dichlorobenzene were added sequentially to a 2 L three-necked flask. The mixture was heated to reflux and stirred until Sub-d1 was completely consumed. After the system temperature cooled to room temperature, the solution was poured into a beaker containing a large amount of ice water and stirred for 5 minutes. The organic phase was separated, and the aqueous phase was extracted with toluene (500 mL × 3). The combined organic phases were washed with a large amount of deionized water until neutral and dried over anhydrous sodium sulfate. The solvent was removed by filtration and vacuum distillation. The crude product was purified by silica gel column chromatography using toluene / dichloromethane as the eluent, finally yielding Sub-e1 (25.8 g, yield 25%) as a yellow solid.

[0166] Intermediates Sub-e2 to Sub-e13, as shown in Table 5, were synthesized using the same method as Sub-e1, except that reactant I replaced Sub-d1. The main raw materials used, the intermediates synthesized, and their yields are shown in Table 5.

[0167] Table 5

[0168]

[0169]

[0170] 6. Synthesis of Sub-f1:

[0171]

[0172] Sub-c2 (23.0 g, 37.2 mmol), RM-7 (15.9 g, 37.1 mmol), cesium carbonate (30.3 g, 92.9 mmol), 2,2,6,6-tetramethyl-3,5-heptadecyl dione (5.5 g, 29.7 mmol), and N,N-dimethylformamide (250 mL) were added sequentially to a 500 mL three-necked flask. The mixture was heated to approximately 100 °C under an argon atmosphere, followed by the addition of cuprous bromide (0.5 g, 3.7 mmol). The mixture was then heated to reflux, and the reaction was stirred until Sub-c2 was completely consumed. After the system cooled to room temperature, the reaction mixture was poured into 300 mL of deionized water. The aqueous phase was then extracted with toluene (150 mL × 3). The organic phases were combined and dried over anhydrous sodium sulfate. The solvent was removed by filtration and vacuum distillation. The crude product was purified by silica gel column chromatography using petroleum ether / toluene as eluent, and the final product was Sub-f1 (32.70 g, yield 87%) as a yellow solid.

[0173] Intermediates Sub-f2 to Sub-f3, as shown in Table 6, were synthesized using the same method as Sub-f1, except that reactant I was used instead of RM-7. The intermediates used and their yields are shown in Table 6.

[0174] Table 6

[0175]

[0176] Synthesis Example 1: Synthesis of Compound 1

[0177]

[0178] Under a nitrogen atmosphere, Sub-Cl (13.5 g, 21.8 mmol) was dissolved in 150 mL of tert-butylbenzene. The mixture was then cooled to -30 °C and tert-butyllithium (37.0 mL, 48.0 mmol, 1.3 M pentane solution) was added. The mixture was reacted at this temperature for 30 minutes, then heated to room temperature and reacted for another hour. After the starting material was completely consumed, BBr3 (6.0 g, 24.0 mmol) was added and the mixture was reacted at room temperature for 1 hour. Then, pentamethylpiperidine (10.2 g, 65.5 mmol) was added and the mixture was refluxed for 18 hours.

[0179] In addition, Sub-e1 (22.9 g, 45.8 mmol) was dissolved in 200 mL of tert-butylbenzene under a nitrogen atmosphere, and then the mixture was cooled to -30 °C and butyllithium (23.0 mL, 45.8 mmol, 2.0 M hexane solution) was added. The reaction was carried out at this temperature for 1 hour. After the starting material was completely consumed, the resulting solution was added dropwise to a pre-prepared boron bromide intermediate at 0 °C, and the mixture was stirred at room temperature for 2 hours. Then, 300 mL of deionized water was added and the mixture was stirred for another 5 minutes. The organic phase was separated and the aqueous phase was extracted with toluene (100 mL × 3). The combined organic phases were dried over anhydrous sodium sulfate, filtered, and the solvent was removed by vacuum distillation. The crude product was purified by silica gel column chromatography using toluene / n-heptane as the mobile phase, finally yielding compound 1 (3.1 g, yield 14%) as a yellow solid. Mass spectrometry (m / z) = 1013.43 [M + H] + .

[0180] The compounds listed in Table 7 were synthesized using the same method as compound 1, except that reactant K was used instead of Sub-c1 and reactant L was used instead of Sub-e1. The main raw materials used, the synthesized compounds, their mass spectra, and yields are shown in Table 7.

[0181] Table 7

[0182]

[0183]

[0184]

[0185] Synthesis Example 19: Synthesis of Compound 3:

[0186]

[0187] Under a nitrogen atmosphere, Sub-f1 (32.0 g, 31.7 mmol), boron tribromide (79.3 g, 316.6 mmol), and 500 mL of o-dichlorobenzene were added sequentially to a 1 L three-necked flask. The mixture was heated to reflux and stirred until Sub-f1 was completely consumed. After the system temperature cooled to room temperature, the solution was poured into a beaker containing a large amount of ice water and stirred for 5 minutes. The organic phase was separated, and the aqueous phase was extracted with toluene (250 mL × 3). The combined organic phases were washed with a large amount of deionized water until neutral and dried over anhydrous sodium sulfate. The solvent was removed by vacuum distillation after filtration. The crude product was purified by silica gel column chromatography using toluene / heptane as the eluent, finally yielding a yellow solid compound 3 (3.3 g, yield 10%). Mass spectrometry (m / z) = 1027.41 [M+H] + .

[0188] The compounds listed in Table 8 were synthesized using the same method as compound 3, except that reactant M was used instead of Sub-f1. The main raw materials used, the intermediates synthesized, their mass spectra, and the yields are shown in Table 8.

[0189] Table 8

[0190]

[0191] NMR data for some compounds are shown in Table 5 below.

[0192] Table 5

[0193]

[0194] Example 1: Red Organic Electroluminescent Device

[0195] First, anodizing pretreatment is performed through the following process: [The process is repeated in the original text, so the translation is incomplete.] On the ITO / Ag / ITO substrate, surface treatment is performed using ultraviolet ozone and O2:N2 plasma to increase the work function of the anode. Organic solvents are also used to clean the surface of the ITO substrate to remove impurities and oil stains.

[0196] On the experimental substrate (anode), compounds HT-28 and NDP-9 were co-deposited at a deposition rate of 98%:2% to form a layer with a thickness of [missing information]. Hole injection layer.

[0197] On the hole injection layer, compound HT-28 is vacuum-deposited to form a layer with a thickness of [missing information]. The first hole transport layer.

[0198] On the first hole transport layer, compound HT-29 is vacuum-deposited to form a layer with a thickness of [missing information]. The second hole transport layer.

[0199] On the second hole transport layer, 4P-NPB∶PO-T2T∶Ir(tptpy)2(acac)∶Compound 1 were co-deposited at a deposition rate of 55%∶37%∶7.5%∶0.5% to form a layer with a thickness of [missing information]. The organic light-emitting layer.

[0200] On the organic light-emitting layer, compound ET-15 and LiQ were co-deposited at a 1:1 evaporation rate to form... A thick electron transport layer is formed by depositing Yb on the electron transport layer to create a thickness of [thickness value missing]. An electron-injected layer was formed, and then magnesium (Mg) and silver (Ag) were co-deposited onto the electron-injected layer at a evaporation rate ratio of 1:9, forming a layer with a thickness of [missing information]. The cathode.

[0201] Finally, compound CP-1 is deposited on the cathode to form a thickness of [thickness value missing]. The cathode capping layer is used to complete the fabrication of the organic electroluminescent device.

[0202] Example 2-Example 21

[0203] Organic electroluminescent devices were prepared using the same method as in Example 1, except that compound 1 was replaced with the compounds in Table 9 below when forming the light-emitting layer.

[0204] Comparative Example 1 - Comparative Example 2

[0205] Organic electroluminescent devices were prepared using the same method as in Example 1, except that compound 1 was replaced with compounds A and B when forming the light-emitting layer.

[0206] The main material structures used in the above embodiments and comparative examples are shown in the table below.

[0207]

[0208] The performance of the red organic electroluminescent devices prepared in Examples 1-21 and Comparative Examples 1-2 was tested, specifically at 10 mA / cm². 2 The IVL performance of the device was tested under the specified conditions. The lifetime of the T95 device was 20 mA / cm. 2 The test was conducted under the specified conditions, and the results are shown in Table 9 below:

[0209] Table 9

[0210]

[0211]

[0212] Referring to Table 9 above, in Examples 1-21, the compounds of the present invention were used as doping materials for the light-emitting layer. Compared with Comparative Examples 1-2, the luminous efficiency was improved by at least 10.84%, and the device lifetime was improved by at least 11.47%. It is evident that using the organic compounds of this application in the light-emitting layer of organic electroluminescent devices can improve the luminous efficiency and T95 lifetime of organic electroluminescent devices.

[0213] The preferred embodiments of this application have been described in detail above with reference to the accompanying drawings. However, this application is not limited to the specific details of the above embodiments. Within the scope of the technical concept of this application, various simple modifications can be made to the technical solution of this application, and these simple modifications all fall within the protection scope of this application.

[0214] It should also be noted that the various specific technical features described in the above embodiments can be combined in any suitable manner without contradiction. In order to avoid unnecessary repetition, this application will not describe the various possible combinations separately.

Claims

1. An organic compound, characterized in that, The organic compound has the structure shown in Formula 1: Among them, Z1, Z2, Z3, and Z4 may be the same or different, and each is independently selected from C(R). a R b ), N(R c ), O or S; p1 is the number of Z1s. p1 is 0 or 1. When p1 is 0, it means that Z1 does not exist. p2 is the number of Z2s. p2 is 0 or 1. When p2 is 0, it means that Z2 does not exist. p3 is the number of Z3s. p3 is 0 or 1. When p3 is 0, it means that Z3 does not exist. p4 is the number of Z4s. p4 is 0 or 1. When p4 is 0, it means that Z4 does not exist. R a R b and R c They may be the same or different, and each is independently selected from alkyl groups having 1 to 10 carbon atoms, deuterated alkyl groups having 1 to 10 carbon atoms, haloalkyl groups having 1 to 10 carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, and substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms. R1, R2, R3, R4, R5, and R6 may be the same or different, and each is independently selected from hydrogen, deuterium, halogen groups, cyano, alkyl groups with 1 to 10 carbon atoms, deuterated alkyl groups with 1 to 10 carbon atoms, haloalkyl groups with 1 to 10 carbon atoms, trialkylsilyl groups with 3 to 12 carbon atoms, triphenylsilyl groups, cycloalkyl groups with 3 to 10 carbon atoms, substituted or unsubstituted aryl groups with 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups with 3 to 30 carbon atoms, or... The structure shown; Ar a Ar b Ar1, Ar2, Ar3 and Ar4 may be the same or different, and each is independently selected from substituted or unsubstituted aryl groups with 6 to 30 carbon atoms, or substituted or unsubstituted heteroaryl groups with 3 to 30 carbon atoms; R a R b R c Ar a Ar b The substituents in Ar1, Ar2, Ar3, Ar4, R1, R2, R3, R4, R5, and R6 may be the same or different, and each is independently selected from deuterium, halogen groups, cyano, alkyl with 1 to 10 carbon atoms, deuterated alkyl with 1 to 10 carbon atoms, haloalkyl with 1 to 10 carbon atoms, trialkylsilyl with 3 to 12 carbon atoms, triphenylsilyl, cycloalkyl with 3 to 10 carbon atoms, aryl with 6 to 20 carbon atoms, deuterated aryl with 6 to 20 carbon atoms, or heteroaryl with 3 to 20 carbon atoms; n1 is the number of R1s, and n1 is selected from 1, 2, 3 or 4. When n1 is greater than 1, any two R1s are the same or different. n2 is the number of R2, which can be selected from 1, 2, 3 or 4. When n2 is greater than 1, any two R2 are the same or different. n3 is the number of R3s, and n1 is selected from 1, 2, 3 or 4. When n3 is greater than 1, any two R3s are the same or different. n4 is the number of R4s, and n2 is selected from 1, 2, 3 or 4. When n4 is greater than 1, any two R4s are the same or different. n5 is the number of R5s, which can be selected from 1, 2, 3 or 4. When n5 is greater than 1, any two R5s can be the same or different. n6 is the number of R6s, and n2 is selected from 1, 2, 3 or 4. When n6 is greater than 1, any two R6s are the same or different.

2. The organic compound according to claim 1, wherein, The organic compound has the structure shown in Formula 1-1, Formula 1-2, Formula 1-3, Formula 1-4, Formula 1-5, Formula 1-6, Formula 1-7, Formula 1-8 or Formula 1-9: In Equations 1-1 to 1-9, the definitions of Z1, Z2, Z3, Z4, Ar1, Ar2, Ar3, Ar4, R1, R2, R3, R4, R5, R6, n1, n2, n3, n4, n5, or n6 are the same as in Equation 1.

3. The organic compound according to claim 1, wherein, R a R b and R c They may be the same or different, and each is independently selected from alkyl groups having 1 to 5 carbon atoms, deuterated alkyl groups having 1 to 5 carbon atoms, haloalkyl groups having 1 to 5 carbon atoms, substituted or unsubstituted aryl groups having 6 to 20 carbon atoms, and substituted or unsubstituted heteroaryl groups having 12 to 20 carbon atoms. Optionally, R a R b and R c The substituents in the group may be the same or different, and each is independently selected from deuterium, fluorine, cyano, alkyl with 1 to 5 carbon atoms, deuterated alkyl with 1 to 5 carbon atoms, haloalkyl with 1 to 5 carbon atoms, trialkylsilyl with 3 to 6 carbon atoms, cycloalkyl with 3 to 10 carbon atoms, aryl with 6 to 12 carbon atoms, deuterated aryl with 6 to 12 carbon atoms, or heteroaryl with 3 to 12 carbon atoms.

4. The organic compound according to claim 1, wherein, R a R b and R c They may be the same or different, and each is independently selected from methyl, ethyl, isopropyl, tert-butyl, trideuterated methyl, trifluoromethyl, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted phenanthrene, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted carbazolyl; Optionally, R a R b and R c The substituents in the group may be the same or different, and each is independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trideuterated methyl, trifluoromethyl, trimethylsilyl, phenyl, naphthyl, pentadeuterated phenyl, dibenzofuranyl, dibenzothiopheneyl or carbazoyl.

5. The organic compound according to claim 1, wherein, R a R b and R c They may be the same or different, and each is independently selected from methyl, ethyl, isopropyl, tert-butyl, trideuterated methyl, trifluoromethyl, phenyl, pentadeuterated phenyl, naphthyl, biphenyl, terphenyl, phenanthryl, dibenzofuranyl, dibenzothiophene, or carbazolyl.

6. The organic compound according to claim 1, wherein, Ar1, Ar2, Ar3 and Ar4 may be the same or different, and each is independently selected from substituted or unsubstituted aryl groups with 6 to 20 carbon atoms, or substituted or unsubstituted heteroaryl groups with 12 to 24 carbon atoms. Optionally, the substituents in Ar1, Ar2, Ar3 and Ar4 may be the same or different, and each may be independently selected from deuterium, fluorine, cyano, alkyl with 1 to 5 carbon atoms, deuterated alkyl with 1 to 5 carbon atoms, haloalkyl with 1 to 5 carbon atoms, trialkylsilyl with 3 to 6 carbon atoms, cycloalkyl with 3 to 10 carbon atoms, aryl with 6 to 12 carbon atoms, deuterated aryl with 6 to 12 carbon atoms, or heteroaryl with 3 to 12 carbon atoms.

7. The organic compound according to claim 1, wherein, Ar1, Ar2, Ar3, and Ar4 may be the same or different, and each is independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted phenanthyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted 9,10-dihydro-acridyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted carbazoyl; Optionally, the substituents in Ar1, Ar2, Ar3 and Ar4 may be the same or different, and each may be independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trideuterated methyl, trifluoromethyl, trimethylsilyl, cyclopropane, cyclopentane, cyclohexane, adamantane, phenyl, pentadeuterated phenyl, dibenzofuranyl, dibenzothiopheneyl or carbazoyl.

8. The organic compound according to claim 1, wherein, Ar1, Ar2, Ar3, and Ar4 may be the same or different, and each is independently selected from the group consisting of the following groups:

9. The organic compound according to claim 1, wherein, R1, R2, R3, R4, R5, and R6 may be the same or different, and each is independently selected from hydrogen, deuterium, fluorine, cyano, alkyl with 1 to 5 carbon atoms, deuterated alkyl with 1 to 5 carbon atoms, haloalkyl with 1 to 5 carbon atoms, trialkylsilyl with 3 to 6 carbon atoms, triphenylsilyl, cycloalkyl with 3 to 10 carbon atoms, substituted or unsubstituted aryl with 6 to 20 carbon atoms, substituted or unsubstituted heteroaryl with 12 to 24 carbon atoms, or... The structure shown; Ar a and Ar b They may be the same or different, and each is independently selected from substituted or unsubstituted aryl groups with 6 to 20 carbon atoms, or substituted or unsubstituted heteroaryl groups with 12 to 20 carbon atoms; Optionally, Ar a Ar b The substituents in R1, R2, R3, R4, R5, and R6 may be the same or different, and each is independently selected from deuterium, fluorine, cyano, alkyl with 1 to 5 carbon atoms, deuterated alkyl with 1 to 5 carbon atoms, haloalkyl with 1 to 5 carbon atoms, trialkylsilyl with 3 to 6 carbon atoms, cycloalkyl with 3 to 10 carbon atoms, aryl with 6 to 12 carbon atoms, deuterated aryl with 6 to 12 carbon atoms, or heteroaryl with 3 to 12 carbon atoms.

10. The organic compound according to claim 1, wherein, R1, R2, R3, R4, R5, and R6 may be the same or different, and each is independently selected from hydrogen, deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trideuterated methyl, trifluoromethyl, trimethylsilyl, triphenylsilyl, cyclopropane, cyclopentane, cyclohexane, adamantane, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted phenanthyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted 9,10-dihydro-acridyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiopheneyl, substituted or unsubstituted carbazoleyl, or the following groups: Optionally, the substituents in R1, R2, R3, R4, R5 and R6 may be the same or different, and each may be independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trideuterated methyl, trifluoromethyl, trimethylsilyl, cyclopropane, cyclopentane, cyclohexane, adamantane, phenyl, pentadeuterated phenyl, dibenzofuranyl, dibenzothiopheneyl or carbazoyl.

11. The organic compound according to claim 1, wherein, R1, R2, R3, R4, R5, and R6 may be the same or different, and each is independently selected from the group consisting of hydrogen, deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trideuterated methyl, trifluoromethyl, trimethylsilyl, triphenylsilyl, cyclopropane, cyclopentane, cyclohexane, adamantane, or the following groups:

12. The organic compound according to claim 1, wherein, The organic compound is selected from the group consisting of the following compounds:

13. An electronic component, characterized in that, The electronic component includes an anode and a cathode disposed opposite to each other, and a functional layer disposed between the anode and the cathode; wherein the functional layer comprises an organic compound as described in any one of claims 1 to 12.

14. The electronic component according to claim 13, wherein, The functional layer includes an organic light-emitting layer, and the organic light-emitting layer contains the organic compound; Optionally, the electronic component is an organic electroluminescent device.

15. An electronic device, characterized in that, The electronic device includes the electronic components as described in claim 13 or 14.

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