Organic compounds, electronic components and electronic devices

By using an organic compound containing the parent nucleus structure of phenanthropocene/thiazole in an organic electroluminescent device, the compound has solved the organic electroluminescence in the prior art by connecting arylamine compounds to enhance the intermolecular force by enhancing the intermolecular force. The problem of insufficient device life and efficiency achieves higher luminous efficiency and life.

CN117430568BActive Publication Date: 2025-02-14SHAANXI LIGHTE OPTOELECTRONICS MATERIAL CO LTD
View PDF 2 Cites 0 Cited by

Patent Information

Application Number
CN202310975792.3
Authority / Receiving Office
CN · China
Patent Type
Patents(China)
Current Assignee / Owner
Filing Date
2023-08-03
Publication Date
2025-02-14
Estimated Expiration
2043-08-03

AI Technical Summary

Technical Problem

The existing organic electroluminescent devices have shortcomings in terms of life and efficiency, especially when the driving voltage is increased, the luminous efficiency and current efficiency need to be further improved.

Method used

Provided is an organic compound containing a parent nucleus structure of phenanthobenzoxazole/thiazole. The compound enhances intermolecular force by connecting arylamine compounds, improves carrier mobility, and is used in the air of organic electroluminescent devices. Hole-transport material.

Benefits of technology

The carrier balance in the luminescent layer is improved, the carrier recombination region is widened, the exciton generation and utilization efficiency is improved, and the device's luminescent efficiency and lifetime are improved.

✦ Generated by Eureka AI based on patent content.

Smart Images

  • Figure CN117430568B_ABST
    Figure CN117430568B_ABST
Patent Text Reader

Abstract

The present application relates to the technical field of organic electroluminescent materials, and provides an organic compound, an organic electroluminescent device and an electronic device. The organic compound of the present application has a structure as shown in Formula 1, which can significantly improve the performance of the device.
Need to check novelty before this filing date? Find Prior Art

Description

Technical Field

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

[0002] Organic electroluminescent devices, such as organic light-emitting diodes (OLEDs), generally include a cathode and an anode disposed opposite to each other, and a functional layer disposed between the cathode and the anode. The functional layer is composed of multiple organic or inorganic film layers, and generally includes an organic light-emitting layer, a hole transport layer, an electron transport layer, etc. When a voltage is applied to the positive and negative electrodes, the two electrodes generate an electric field. Under the action of the electric field, the electrons on the cathode side move toward the electroluminescent layer, and the holes on the anode side also move toward the light-emitting layer. The electrons and holes combine in the electroluminescent layer to form excitons, and the excitons are in an excited state and release energy outward, thereby causing the electroluminescent layer to emit light outward.

[0003] The main problems of existing organic electroluminescent devices are lifespan and efficiency. As the display area becomes larger, the driving voltage also increases, and the luminous efficiency and current efficiency also need to be improved. Therefore, it is necessary to continue to develop new materials to further improve the performance of organic electroluminescent devices. Summary of the invention

[0004] In view of the above problems existing in the prior art, the purpose of the present application is to provide an organic compound and an organic electroluminescent device and an electronic device containing the same. The organic compound is used in an organic electroluminescent device to improve the performance of the device.

[0005] The first aspect of the present application provides an organic compound having a structure shown in Formula 1:

[0006]

[0007] Wherein, one of X and Y is -O- or -S-, and the other is -N=;

[0008] Each R 1 , R 2 , R 3 and R 4 are the same or different and are independently selected from hydrogen, deuterium, cyano, halogen, alkyl having 1 to 10 carbon atoms, halogenated alkyl having 1 to 10 carbon atoms, deuterated alkyl having 1 to 10 carbon atoms, aryl having 6 to 20 carbon atoms, deuterated aryl having 6 to 20 carbon atoms, heteroaryl having 3 to 20 carbon atoms, cycloalkyl having 3 to 10 carbon atoms or a group represented by Formula 2, and each R 1 , R 2 , R 3 and R 4There is only one group represented by Formula 2;

[0009]

[0010] n1 is R 1 The number of R is selected from 0, 1 or 2; when n1 is greater than 1, any two R 1 Same or different;

[0011] n2 is R 2 The number of R is selected from 0, 1 or 2; when n2 is greater than 1, any two R 2 Same or different;

[0012] n3 is R 3 The number of R is selected from 0, 1, 2, 3 or 4; when n3 is greater than 1, any two R 3 Same or different;

[0013] n4 is R 4 The number of R is selected from 0, 1 or 2; when n4 is greater than 1, any two R 4 Same or different;

[0014] L, L 1 and L 2 are the same or different and are each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, and a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms;

[0015] Ar 1 ,Ar 2 and Ar 3 are the same or different and are each independently selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms and a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms;

[0016] L, L 1 , L 2 ,Ar 1 ,Ar 2 and Ar 3 The substituents in are the same or different and are independently selected from deuterium, cyano, halogen groups, alkyl groups having 1 to 10 carbon atoms, haloalkyl groups having 1 to 10 carbon atoms, deuterated alkyl groups having 1 to 10 carbon atoms, aryl groups having 6 to 20 carbon atoms, deuterated aryl groups having 6 to 20 carbon atoms, heteroaryl groups having 3 to 20 carbon atoms, cycloalkyl groups having 3 to 10 carbon atoms, and trialkylsilyl groups having 3 to 12 carbon atoms;

[0017] Optionally, Ar 1 ,Ar 2 and Ar 3Any two adjacent substituents form a saturated or unsaturated 5-15 membered ring.

[0018] The second aspect of the present application provides an organic electroluminescent device, comprising an anode and a cathode arranged opposite to each other, and a functional layer arranged between the anode and the cathode; the functional layer comprises the above-mentioned organic compound.

[0019] The third aspect of the present application provides an electronic device, comprising the organic electroluminescent device described in the second aspect.

[0020] The compound structure of the present application contains a parent core structure of phenanthrobenzoxazole / thiazole, and the parent core is connected to an aromatic amine compound, which is used as an electron-transmitting red light host material. Among them, phenanthrobenzoxazole / thiazole has a large conjugated system, and after connecting it with an aromatic amine, it can enhance the intermolecular force and improve the compound carrier mobility. When the compound of the present application is used as a hole-transporting material in a hybrid host material, the carrier balance in the light-emitting layer can be improved, the carrier recombination area can be widened, the exciton generation and utilization efficiency can be improved, and the device luminous efficiency and life can be improved. BRIEF DESCRIPTION OF THE DRAWINGS

[0021] The accompanying drawings are used to provide further understanding of the present application and constitute a part of the specification. Together with the following specific embodiments, they are used to explain the present application, but do not constitute a limitation to the present application.

[0022] Figure 1 It is a schematic diagram of the structure of an organic electroluminescent device according to one embodiment of the present application.

[0023] Figure 2 It is a schematic diagram of the structure of an electronic device according to an embodiment of the present application.

[0024] Reference numerals

[0025] 100, anode; 200, cathode; 300, functional layer; 310, hole injection layer;

[0026] 320, hole transport layer; 330, hole adjustment layer; 340, organic light emitting layer; 350, electron transport layer;

[0027] 360, electron injection layer; 400, electronic device DETAILED DESCRIPTION

[0028] Exemplary embodiments will now be described more fully with reference to the accompanying drawings. However, exemplary embodiments can be implemented in a variety of forms and should not be construed as being limited to the examples set forth herein; rather, these embodiments are provided so that the present application will be more comprehensive and complete and the concepts of the exemplary embodiments will be fully conveyed 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, many specific details are provided to provide a full understanding of the embodiments of the present application.

[0029] In a first aspect, the present application provides an organic compound having a structure shown in the following formula 1:

[0030]

[0031] Wherein, one of X and Y is -O- or -S-, and the other is -N=;

[0032] Each R 1 , R 2 , R 3 and R 4 are the same or different and are independently selected from hydrogen, deuterium, cyano, halogen, alkyl having 1 to 10 carbon atoms, halogenated alkyl having 1 to 10 carbon atoms, deuterated alkyl having 1 to 10 carbon atoms, aryl having 6 to 20 carbon atoms, deuterated aryl having 6 to 20 carbon atoms, heteroaryl having 3 to 20 carbon atoms, cycloalkyl having 3 to 10 carbon atoms or a group represented by Formula 2, and each R 1 , R 2 , R 3 and R 4 There is only one group represented by Formula 2;

[0033] n1 is R 1 The number of R is selected from 0, 1 or 2; when n1 is greater than 1, any two R 1 Same or different;

[0034] n2 is R 2 The number of R is selected from 0, 1 or 2; when n2 is greater than 1, any two R 2 Same or different;

[0035] n3 is R 3 The number of R is selected from 0, 1, 2, 3 or 4; when n3 is greater than 1, any two R 3 Same or different;

[0036] n4 is R 4 The number of R is selected from 0, 1 or 2; when n4 is greater than 1, any two R 4 Same or different;

[0037] Z 1 , Z 2 and Z 3 are each independently selected from C(H) or N, and Z 1 , Z 2 and Z 3 At least two of them are N;

[0038] L, L 1 and L 2 are the same or different and are each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, and a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms;

[0039] Ar 1 ,Ar 2 and Ar 3 are the same or different and are each independently selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms and a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms;

[0040] L, L 1 , L 2 ,Ar 1 ,Ar 2 and Ar 3 The substituents in are the same or different and are independently selected from deuterium, cyano, halogen groups, alkyl groups having 1 to 10 carbon atoms, haloalkyl groups having 1 to 10 carbon atoms, deuterated alkyl groups having 1 to 10 carbon atoms, aryl groups having 6 to 20 carbon atoms, deuterated aryl groups having 6 to 20 carbon atoms, heteroaryl groups having 3 to 20 carbon atoms, cycloalkyl groups having 3 to 10 carbon atoms, and trialkylsilyl groups having 3 to 12 carbon atoms;

[0041] Optionally, Ar 1 ,Ar 2 and Ar 3 Any two adjacent substituents form a saturated or unsaturated 5-15 membered ring.

[0042] In Formula I Part is a heteroaryl group, for example, when X is O or S, Y is -N=, and the structure is represented by Or, when Y is O or S, X is -N=, the structures are respectively represented as

[0043] In the present application, the terms "optionally" and "optionally" mean that the event or environment described subsequently may or may not occur. For example, "optionally, any two adjacent substituents form a ring" means that the two substituents may or may not form a ring, that is, including: the scenario where two adjacent substituents form a ring and the scenario where two adjacent substituents do not form a ring. For another example, "optionally, any two adjacent substituents form a ring" means that any two adjacent substituents are connected to each other to form a ring, or any two adjacent substituents may also exist independently. "Any two adjacent" may include two substituents on the same atom, and may also include two adjacent atoms each having a substituent; wherein, when there are two substituents on the same atom, the two substituents may form a saturated or unsaturated spiro ring with the atom to which they are commonly connected; when there is a substituent on each of two adjacent atoms, the two substituents may be fused into a ring.

[0044] In the present application, a saturated or unsaturated 5-13 membered ring refers to a carbon ring or heterocyclic ring containing 5-13 ring atoms; for example, but not limited to, cyclopentane, cyclohexane, benzene ring, fluorene ring, pyran ring, tetrahydropyran ring, piperidine ring, tetrahydropiperidine ring, etc.

[0045] In the present application, the cycloalkyl group having 5 to 10 carbon atoms refers to a cycloalkyl group formed by 5 to 10 carbon atoms, such as but not limited to cyclopentyl, cyclohexyl, adamantyl and the like.

[0046] In the present application, a 6- to 15-membered unsaturated ring refers to an unsaturated ring formed by 6 to 15 ring atoms, such as but not limited to a benzene ring, a fluorene ring, a furan ring, a pyran ring, and the like.

[0047] In this application, the descriptions "each ... independently is" and "each ... independently is" and "... independently is" are interchangeable and should be understood in a broad sense, which can mean that in different groups, the specific options expressed by the same symbols do not affect each other, or in the same group, the specific options expressed by the same symbols do not affect each other. For example, Wherein, each q is independently 0, 1, 2 or 3, and each R" is independently selected from hydrogen, deuterium, fluorine, and chlorine, which means: Formula Q-1 indicates that there are q substituents R" on the benzene ring, and 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, and the number q of R" substituents on the two benzene rings can be the same or different, and each R" can be the same or different, and the options of each R" do not affect each other.

[0048] In the present application, the term "substituted or unsubstituted" means that the functional group recorded after the term may or may not have a substituent (hereinafter, for the convenience of description, the 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 above-mentioned substituent, i.e., Rc, can be, for example, deuterium, a halogen group, a cyano group, a heteroaryl group, an aryl group, an alkyl group, a haloalkyl group, a deuterated alkyl group, a deuterated aryl group, a haloaryl group, a cycloalkyl group, etc. The number of substitutions can be 1 or more.

[0049] In the present application, "plurality" means more than 2, for example, 2, 3, 4, 5, 6, etc.

[0050] The hydrogen atoms in the structures of the compounds of the present application include various isotope atoms of the hydrogen element, such as hydrogen (H), deuterium (D) or tritium (T).

[0051] In the present application, the number of carbon atoms of a substituted or unsubstituted functional group refers to the total number of carbon atoms. For example, if L is a substituted arylene group having 12 carbon atoms, the total number of carbon atoms of the arylene group and the substituents thereon is 12.

[0052] In the present application, aryl refers to an optional functional group or substituent derived from an aromatic carbocyclic ring. Aryl can be a monocyclic aryl (e.g., phenyl) or a polycyclic aryl. In other words, aryl can be a monocyclic aryl, a condensed ring aryl, two or more monocyclic aryl connected by carbon-carbon single bond conjugation, a monocyclic aryl and a condensed ring aryl connected by carbon-carbon single bond conjugation, two or more condensed ring aryl connected by carbon-carbon single bond conjugation. That is, unless otherwise specified, two or more aromatic groups connected by carbon-carbon single bond conjugation can also be regarded as aryl of the present application. Wherein, condensed ring aryl can, for example, include bicyclic condensed aryl (e.g., naphthyl), tricyclic condensed aryl (e.g., phenanthrenyl, fluorenyl, anthracenyl), etc. Aryl does not contain heteroatoms such as B, N, O, S, P, Se, and Si. Examples of aryl groups may include, but are not limited to, phenyl, naphthyl, fluorenyl, phenyl-naphthyl, spirobifluorenyl, anthracenyl, phenanthrenyl, biphenyl, terphenyl, triphenylene, peryl, benzo[9,10]phenanthrenyl, pyrenyl, benzofluoranthenyl, Ji et al.

[0053] In the present application, the arylene group refers to a divalent or multivalent group formed by further losing one or more hydrogen atoms from an aryl group.

[0054] In the present application, terphenyl includes

[0055] In the present application, the number of carbon atoms of a 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 refers to the total number of carbon atoms of the aryl group and the substituents is 18.

[0056] In the present application, the carbon number of the substituted or unsubstituted aryl (arylene) can be 6, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29 or 30, etc. In some embodiments, the substituted or unsubstituted aryl is a substituted or unsubstituted aryl having 6 to 30 carbon atoms, in other embodiments, the substituted or unsubstituted aryl is a substituted or unsubstituted aryl having 6 to 20 carbon atoms, in other embodiments, the substituted or unsubstituted aryl is a substituted or unsubstituted aryl having 6 to 25 carbon atoms, in other embodiments, the substituted or unsubstituted aryl is a substituted or unsubstituted aryl having 6 to 18 carbon atoms, and in other embodiments, the substituted or unsubstituted aryl is a substituted or unsubstituted aryl having 6 to 15 carbon atoms.

[0057] In the present application, the fluorenyl group may be substituted by one or more substituents. In the case where the above fluorenyl group is substituted, the substituted fluorenyl group may be: Etc., etc., but not limited to these.

[0058] In this application, L, L 1 , L 2 ,Ar 1 ,Ar 2 and Ar 3 The aryl substituents in the group include, but are not limited to, phenyl, naphthyl, phenanthrenyl, biphenyl, fluorenyl, and the like.

[0059] In the present application, heteroaryl refers to a monovalent aromatic ring or a derivative thereof containing 1, 2, 3, 4, 5 or 6 heteroatoms in the ring, and the heteroatoms may be one or more of B, O, N, P, Si, Se and S. The heteroaryl may be a monocyclic heteroaryl or a polycyclic heteroaryl, in other words, the heteroaryl may be a single aromatic ring system or a plurality of aromatic ring systems conjugated by carbon-carbon single bonds, and any aromatic ring system may be an aromatic monocyclic ring or an aromatic condensed ring. By way of example, the heteroaryl group may include a thienyl group, a furyl group, a pyrrolyl group, an imidazolyl group, a thiazolyl group, an oxazolyl group, an oxadiazolyl group, a triazolyl group, a pyridyl group, a bipyridyl group, a pyrimidyl group, a triazine group, an acridinyl group, a pyridazinyl group, a pyrazinyl group, a quinolyl group, a quinazolinyl group, a quinoxalinyl group, a phenoxazinyl group, a phthalazinyl group, a pyridopyrimidinyl group, a pyridopyrazinyl group, a pyrazinopyrazinyl group, an isoquinolyl group, an indolyl group, a carbazolyl group, a benzoxazolyl group, a benzimidazolyl group, a benzothiazolyl group, a benzocarbazolyl group, a benzothienyl group, a dibenzothienyl group, a thienothiphenyl group, a benzofuranyl group, a phenanthrolinyl group, an isoxazolyl group, a thiadiazolyl group, a phenothiazinyl group, a silyfluorenyl group, a dibenzofuranyl group, and an N-phenylcarbazolyl group, an N-pyridylcarbazolyl group, an N-methylcarbazolyl group, and the like, without being limited thereto.

[0060] In the present application, the heteroarylene group refers to a divalent or multivalent group formed by further losing one or more hydrogen atoms from a heteroaryl group.

[0061] In the present application, the number of carbon atoms of the substituted or unsubstituted heteroaryl (heteroarylene) can be selected from 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29 or 30, etc. In some embodiments, the substituted or unsubstituted heteroaryl is a substituted or unsubstituted heteroaryl with a total carbon number of 3 to 18, in other embodiments, the substituted or unsubstituted heteroaryl is a substituted or unsubstituted heteroaryl with a total carbon number of 3 to 12, and in other embodiments, the substituted or unsubstituted heteroaryl is a substituted or unsubstituted heteroaryl with a total carbon number of 5 to 12. In the present application, the heteroaryl group as a substituent in L, L1, L2, Ar1, Ar2 and Ar3 is exemplified but not limited to pyridyl, carbazolyl, quinolyl, isoquinolyl, phenanthroline, benzoxazolyl, benzothiazolyl, benzimidazolyl, dibenzothiophenyl and dibenzofuranyl.

[0062] In the present application, the substituted heteroaryl group may be a heteroaryl group in which one or more hydrogen atoms are replaced by groups such as deuterium atoms, halogen groups, -CN, aryl groups, heteroaryl groups, alkyl groups, cycloalkyl groups, haloalkyl groups, etc. It should be understood that the number of carbon atoms in the substituted heteroaryl group refers to the total number of carbon atoms in the heteroaryl group and the substituents on the heteroaryl group.

[0063] In the present application, the alkyl group having 1 to 10 carbon atoms may include a straight-chain alkyl group having 1 to 10 carbon atoms and a branched-chain alkyl group having 3 to 10 carbon atoms. The number of carbon atoms of the alkyl group is, for example, 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10, and specific examples of the alkyl group include, but are not limited to, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl, neopentyl, n-hexyl, and the like.

[0064] In the present application, the halogen group is, for example, fluorine, chlorine, bromine, or iodine.

[0065] In the present application, specific examples of the haloalkyl group include, but are not limited to, trifluoromethyl.

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

[0067] In the present application, a deuterated aryl group refers to an aryl group containing deuterium, such as but not limited to pentadeuterated phenyl, heptadeuterated naphthyl, deuterated biphenyl and the like.

[0068] In the present application, the halogenated aryl group refers to an aryl group with a halogen substituent, such as but not limited to fluorophenyl, fluoronaphthyl, fluorobiphenyl and the like.

[0069] In the present application, the carbon number of the cycloalkyl group having 3 to 10 carbon atoms is, for example, 3, 4, 5, 6, 7, 8 or 10. Specific examples of the cycloalkyl group include, but are not limited to, cyclopentyl, cyclohexyl, and adamantyl.

[0070] In this application, an unpositioned connecting bond refers to a single bond extending from the ring system. It means that one end of the connecting bond can be connected to any position in the ring system that the bond passes through, and the other end is connected to the rest of the compound molecule. For example, as shown in the following formula (f), the naphthyl represented by formula (f) is connected to other positions of the molecule through two non-positional connecting bonds that pass through the bicyclic ring. The meaning represented by it includes any possible connection mode shown in formula (f-1) to formula (f-10):

[0071]

[0072] For another example, as shown in the following formula (X'), the dibenzofuranyl represented by formula (X') is connected to other positions of the molecule through a non-positional connecting bond extending from the middle of one side of the benzene ring, and the meaning represented by it includes any possible connection mode shown in formula (X'-1) to formula (X'-4):

[0073]

[0074] The non-positioning substituent in the present application refers to a substituent connected by a single bond extending from the center of the ring system, which means that the substituent can be connected to any possible position in the ring system. For example, as shown in the following formula (Y), the substituent R' represented by formula (Y) is connected to the quinoline ring through a non-positioning connection bond, and the meaning represented includes any possible connection mode shown in formula (Y-1) to formula (Y-7):

[0075]

[0076] In some embodiments, Formula 1 is selected from the structures shown in the following formulas (1-1) to (1-2):

[0077]

[0078] In some embodiments, R 1 One of them has the structure shown in Formula 2, when n1 is greater than 1, the other R 1 With each R 2 , R 3 and R 4Each is independently selected from hydrogen, deuterium, cyano, a halogen group, an alkyl group having 1 to 4 carbon atoms, a deuterated alkyl group having 1 to 4 carbon atoms, a halogenated alkyl group having 1 to 4 carbon atoms, an aryl group having 6 to 12 carbon atoms, a deuterated aryl group having 6 to 12 carbon atoms or a heteroaryl group having 5 to 12 carbon atoms.

[0079] In some embodiments, R 2 One of them has the structure shown in Formula 2, when n2 is greater than 1, the other R 2 With each R 1 , R 3 and R 4 Each is independently selected from hydrogen, deuterium, cyano, a halogen group, an alkyl group having 1 to 4 carbon atoms, a deuterated alkyl group having 1 to 4 carbon atoms, a halogenated alkyl group having 1 to 4 carbon atoms, an aryl group having 6 to 12 carbon atoms, a deuterated aryl group having 6 to 12 carbon atoms or a heteroaryl group having 5 to 12 carbon atoms.

[0080] In some embodiments, R 3 One of them has the structure shown in Formula 2, when n3 is greater than 1, the other R 3 With each R 1 , R 2 and R 4 Each is independently selected from hydrogen, deuterium, cyano, a halogen group, an alkyl group having 1 to 4 carbon atoms, a deuterated alkyl group having 1 to 4 carbon atoms, a halogenated alkyl group having 1 to 4 carbon atoms, an aryl group having 6 to 12 carbon atoms, a deuterated aryl group having 6 to 12 carbon atoms or a heteroaryl group having 5 to 12 carbon atoms.

[0081] In some embodiments, R 4 One of them has the structure shown in Formula 2, when n4 is greater than 1, the other R 4 With each R 1 , R 2 and R 3 Each is independently selected from hydrogen, deuterium, cyano, a halogen group, an alkyl group having 1 to 4 carbon atoms, a deuterated alkyl group having 1 to 4 carbon atoms, a halogenated alkyl group having 1 to 4 carbon atoms, an aryl group having 6 to 12 carbon atoms, a deuterated aryl group having 6 to 12 carbon atoms or a heteroaryl group having 5 to 12 carbon atoms.

[0082] In some embodiments, each R 1 , R 2 , R 3 and R 4 The same or different, and each R 1 , R 2 , R 3 and R 4There is only one group represented by Formula 2, and the others are independently selected from hydrogen, deuterium, cyano, fluorine, methyl, ethyl, isopropyl, tert-butyl or phenyl.

[0083] In some embodiments, Ar 1 ,Ar 2 and Ar 3 the same or different and each independently selected from a substituted or unsubstituted aryl group having 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24 or 25 carbon atoms and a substituted or unsubstituted heteroaryl group having 5, 6, 7, 8, 9, 10, 12, 13, 14, 15, 16, 17 or 18 carbon atoms.

[0084] In some embodiments, Ar 1 ,Ar 2 and Ar 3 are the same or different and are each independently selected from a substituted or unsubstituted aryl group having 6 to 25 carbon atoms and a substituted or unsubstituted heteroaryl group having 12 to 18 carbon atoms.

[0085] Optionally, Ar 1 ,Ar 2 and Ar 3 The substituents in are the same or different and are independently selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 4 carbon atoms, a deuterated alkyl group having 1 to 4 carbon atoms, a trialkylsilyl group having 3 to 7 carbon atoms, a naphthyl group, a cycloalkyl group having 5 to 10 carbon atoms, a cyclohexyl group, a phenyl group or a pentadeuterated phenyl group;

[0086] Optionally, Ar 1 ,Ar 2 and Ar 3 Any two adjacent substituents form a fluorene ring.

[0087] Further optionally, Ar 3 It is selected from a substituted or unsubstituted aryl group having 6 to 15 carbon atoms and a substituted or unsubstituted heteroaryl group having 12 to 18 carbon atoms.

[0088] In some embodiments, Ar 1 ,Ar 2 and Ar 3 the same or different, and each independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted fluorenyl, substituted or unsubstituted spirobifluorenyl, substituted or unsubstituted triphenylene, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted carbazolyl.

[0089] In some embodiments, Ar 1 ,Ar 2 and Ar 3 The substituents in are the same or different and are independently selected from deuterium, fluorine, cyano, cyclohexyl, methyl, ethyl, isopropyl, tert-butyl, trimethylsilyl, phenyl, naphthyl or pentadeuterated phenyl.

[0090] Further optionally, Ar 3 is selected from substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted fluorenyl, substituted or unsubstituted dibenzothienyl, and substituted or unsubstituted dibenzofuranyl.

[0091] In some embodiments, Ar 1 and Ar 2 The same or different, each independently selected from a substituted or unsubstituted group W; wherein the unsubstituted group W is selected from the group consisting of the following groups:

[0092]

[0093] The substituted group W has one or more substituents, and the substituents on the substituted group W are each independently selected from deuterium, fluorine, cyano, cyclohexyl, methyl, ethyl, isopropyl, tert-butyl, phenyl or pentadeuterated phenyl, and when the number of substituents on the group W is greater than 1, each substituent is the same or different.

[0094] In some embodiments, Ar 1 and Ar 2 The same or different, and each independently selected from the group consisting of the following groups:

[0095]

[0096] In some embodiments, Ar 1 and Ar 2 The same or different, and each independently selected from the group consisting of the following groups:

[0097]

[0098]

[0099] In some embodiments, Ar 3 is selected from a substituted or unsubstituted group Q; wherein the unsubstituted group Q is selected from the group consisting of the following groups:

[0100]

[0101] The substituted group Q has one or more substituents, and the substituents on the substituted group Q are each independently selected from deuterium, fluorine, cyano, cyclohexyl, methyl, ethyl, isopropyl, tert-butyl, phenyl or pentadeuterated phenyl, and when the number of substituents on the group Q is greater than 1, the substituents are the same or different.

[0102] In some embodiments, Ar 3 Selected from the group consisting of:

[0103]

[0104] In some embodiments, Ar 3 Selected from the group consisting of:

[0105]

[0106] In some embodiments, L 1 , L 2 and L are the same as or different from each other and are each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 15 carbon atoms, and a substituted or unsubstituted heteroarylene group having 12 to 18 carbon atoms.

[0107] In some embodiments, L 1 , L 2 and L are the same as or different from each other and are each independently selected from a single bond, a substituted or unsubstituted arylene group having 6, 7, 8, 9, 10, 11, 12, 13, 14 or 15 carbon atoms, and a substituted or unsubstituted heteroarylene group having 12, 13, 14, 15, 16, 17 or 18 carbon atoms.

[0108] Optionally, L 1 , L 2 The substituents in L are the same as or different from each other and are independently selected from deuterium, fluorine, cyano, an alkyl group having 1 to 5 carbon atoms or a phenyl group.

[0109] Further optionally, L is selected from a single bond, a substituted or unsubstituted aryl group having 6 to 12 carbon atoms.

[0110] In some embodiments, L 1 , L 2 and L are the same as or different from each other, and are each independently selected from a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted fluorenylene group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted dibenzothienyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted carbazolyl group.

[0111] Optionally, L 1 , L 2The substituents in L are the same as or different from each other and are each independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl or phenyl.

[0112] In some embodiments, L is selected from the group consisting of a single bond or the following groups:

[0113]

[0114] In some embodiments, L 1 and L 2 Each is independently selected from the group consisting of a single bond or the following groups:

[0115]

[0116] In some embodiments, L 1 and L 2 Each is independently selected from the group consisting of a single bond or the following groups:

[0117]

[0118]

[0119] In some embodiments, The same or different, and each independently selected from the group consisting of the following groups:

[0120]

[0121] Specifically, The same or different, and each independently selected from the group consisting of the following groups:

[0122]

[0123]

[0124] In some embodiments, the structure shown in Formula 2 Selected from the group consisting of:

[0125]

[0126]

[0127]

[0128] Specifically, the structure shown in Formula 2 Selected from the group consisting of:

[0129]

[0130]

[0131]

[0132]

[0133]

[0134]

[0135]

[0136]

[0137] In some embodiments, the compound has a structure shown in Formula II-1 to II-16:

[0138]

[0139]

[0140] In some embodiments, the compound is selected from the group consisting of:

[0141]

[0142]

[0143]

[0144]

[0145]

[0146]

[0147]

[0148]

[0149]

[0150] In a second aspect of the present application, the present application provides an organic electroluminescent device, comprising an anode and a cathode arranged opposite to each other, and a functional layer arranged between the anode and the cathode; the functional layer comprises the organic compound of the present application.

[0151] In some embodiments of the present application, the organic electroluminescent device is a red organic electroluminescent device. Figure 1As shown, the electroluminescent device may include an anode 100, a hole transport layer 320, a hole adjustment layer 330 (also called a hole auxiliary layer, a second hole transport layer or an electron blocking layer), an organic light emitting layer 340, an electron transport layer 350, an electron injection layer 360 and a cathode 200 which are stacked in sequence.

[0152] Optionally, the anode 100 includes the following anode material, which is optionally a material with a large 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 their alloys; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO) and indium zinc oxide (IZO); combined 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 not limited thereto. Preferably, a transparent electrode including indium tin oxide (ITO) as an anode.

[0153] Optionally, the hole transport layer 320 and the hole adjustment layer 330 include one or more hole transport materials, and 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 refer to the prior art for selection, and this application does not make any special restrictions on this. In some embodiments of the present application, the hole transport layer 320 is HT-5 and the hole adjustment layer 330 is HT-23.

[0154]

[0155]

[0156] Optionally, a hole injection layer 310 may be provided between the anode 100 and the hole transport layer 320 to enhance the ability to inject holes into the hole transport layer 320. The hole injection layer 310 may be made of benzidine derivatives, starburst arylamine compounds, phthalocyanine derivatives or other materials, and the present application does not impose any particular restrictions on this. The material of the hole injection layer 310 may be selected from the following compounds or any combination thereof:

[0157]

[0158] In some embodiments of the present application, the hole injection layer 310 is composed of PD and HT-5.

[0159] Optionally, the organic light-emitting layer 340 may be composed of a single light-emitting layer material, or may include a main material and a doping material. Optionally, the organic light-emitting layer 340 is composed of a main material and a doping material, and holes injected into the organic light-emitting layer 340 and electrons injected into the organic light-emitting layer 340 may be recombined in the organic light-emitting layer 340 to form excitons, and the excitons transfer energy to the main material, and the main material transfers energy to the doping material, thereby enabling the doping material to emit light.

[0160] The main material of the organic light-emitting layer 340 may be a metal chelate compound, a bisphenylethylene derivative, an aromatic amine derivative, a dibenzofuran derivative or other types of materials, and the present application does not impose any special limitation thereto.

[0161] In one embodiment of the present application, the organic light-emitting layer 340 includes the organic compound of the present application.

[0162] Optionally, the organic compound of the present application is used as a host material (hole transport host material) of the organic light emitting layer 340 .

[0163] In some embodiments of the present application, the electronic host material of the organic light-emitting layer 340 is

[0164] The guest material of the organic light-emitting layer 340 can be a compound having a condensed aromatic ring or a derivative thereof, a compound having a heteroaromatic ring or a derivative thereof, an aromatic amine derivative or other materials, and the present application does not impose any special restrictions on this. The guest material is also called a doping material or a dopant. Specific examples of red phosphorescent dopants for red organic electroluminescent devices include, but are not limited to,

[0165]

[0166] In a more specific embodiment, the host material of the organic light emitting layer 340 is the organic compound of the present application and RH—N, and the guest material is RD.

[0167] The electron transport layer 350 may be a single-layer structure or a multi-layer structure, and may include one or more electron transport materials, which may be selected from but not limited to ET-1, LiQ, benzimidazole derivatives, oxadiazole derivatives, quinoxaline derivatives or other electron transport materials, and the present application does not make any special restrictions. The materials of the electron transport layer 350 include but are not limited to the following compounds:

[0168]

[0169]

[0170] In some specific embodiments of the present application, the electron transport layer 350 is composed of ET-1 and LiQ.

[0171] In the present application, cathode 200 may include a cathode material, which is a material with a small work function that 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 their alloys; or multilayer materials such as LiF / Al, Liq / Al, LiO2 / Al, LiF / Ca, LiF / Al and BaF2 / Ca. Optionally, a metal electrode containing magnesium and silver is included as the cathode.

[0172] In some embodiments of the present application, the electron injection layer 360 may include ytterbium (Yb).

[0173] A third aspect of the present application provides an electronic device, comprising the organic electroluminescent device described in the second aspect of the present application.

[0174] According to one embodiment, Figure 2 As shown, the electronic device provided is an electronic device 400, which includes the above-mentioned organic electroluminescent device. The electronic device 400 can be, for example, a display device, a lighting device, an optical communication device, or other types of electronic devices, for example, it can include but is not limited to a computer screen, a mobile phone screen, a television, an electronic paper, an emergency lighting lamp, an optical module, etc. The synthesis method of the organic compound of the present application is specifically described below in conjunction with the synthesis example, but the present disclosure is not limited thereto.

[0175] Synthesis Example

[0176] Those skilled in the art will recognize that the chemical reactions described herein can be used to appropriately prepare many of the organic compounds of the present invention, and that other methods for preparing the compounds of the present invention are considered to be within the scope of the present invention. For example, the synthesis of the compounds not exemplified herein can be successfully accomplished by those skilled in the art by modification methods, such as appropriate protection of interfering groups, by utilizing other known reagents in addition to those described herein, or by making some conventional modifications to the reaction conditions. The compounds of the synthetic methods not mentioned in the present invention are all raw materials obtained through commercial channels.

[0177] Synthesis of intermediates:

[0178] Synthesis of intermediate Sub-a1:

[0179]

[0180] Under nitrogen protection, 1-bromo-3-hydroxynaphthalene (CAS: 116632-05-4, 11.15 g, 50 mmol), benzylamine (CAS: 100-46-9, 10.71 g, 100 mmol), ammonium persulfate ((NH4)2S2O8, 22.82 g, 100 mmol), 2,2,6,6-tetramethylpiperidinoxide (TEMPO, 15.63 g, 100 mmol) and acetonitrile (CH3CN, 150 mL) were added to a 250 mL three-necked flask in sequence, stirring and heating were started, and the reaction system was heated to 50 ° C and stirred for 24 h. After the system was cooled to room temperature, it was extracted with dichloromethane (100 mL × 3 times), the organic phases were combined and dried with anhydrous magnesium sulfate, filtered and the solvent was removed by reduced pressure distillation to obtain a crude product. The crude product was purified by silica gel column chromatography using ethyl acetate / n-heptane as the mobile phase to obtain Sub-a1 as an off-white solid (9.4 g, yield: 58%).

[0181] Referring to the synthesis of intermediate Sub-a1, reactant A shown in Table 1 was used instead of benzylamine to synthesize intermediates Sub-a2 to Sub-a6.

[0182] Table 1: Synthesis of Intermediate Sub-a2 and Intermediate Sub-a6

[0183]

[0184]

[0185] Synthesis of intermediate Sub-b1:

[0186]

[0187] Under nitrogen protection, add Sub-a1 (16.20 g, 50 mmol), 5-chloro-2-formylphenylboronic acid (CAS: 870238-36-1, 10.14 g, 55 mmol), tetrakis(triphenylphosphine)palladium (Pd(PPh3)4, 0.58 g, 0.5 mmol), anhydrous sodium carbonate (Na2CO3, 10.60 g, 100 mmol), toluene (PhMe, 160 mL), anhydrous ethanol (EtOH, 40 mL) and deionized water (40 mL) to a 500 mL three-necked flask in sequence, start stirring and heating, and heat to reflux for 8 h. After the system is cooled to room temperature, extract with dichloromethane (100 mL × 3 times), combine the organic phases and dry with anhydrous magnesium sulfate, filter and remove the solvent by reduced pressure distillation to obtain a crude product. The crude product was purified by silica gel column chromatography using dichloromethane / n-heptane as the mobile phase to obtain Sub-b1 as a white solid (10.94 g, yield: 57%).

[0188] Referring to the synthesis of intermediate Sub-b1, reactant B shown in Table 2 was used instead of Sub-a1, and reactant C was used instead of 5-chloro-2-formylphenylboronic acid to synthesize intermediates Sub-b2 to Sub-b8.

[0189] Table 2: Synthesis of Intermediate Sub-b2 to Intermediate Sub-b8

[0190]

[0191] Synthesis of intermediate Sub-c1:

[0192]

[0193] Under nitrogen protection, add Sub-b1 (49.90g, 130mmol), (methoxymethyl) triphenylphosphonium chloride (74.38g, 217mmol) and anhydrous tetrahydrofuran (500mL) to a 1000mL three-necked flask in sequence, cool the system to 0℃ with an ice-water bath; then slowly drop potassium tert-butoxide in anhydrous tetrahydrofuran solution (1M, 220mL) into the system; after the addition is complete, let the system slowly warm up to room temperature and continue to stir and react for 6h. Pour the reaction solution into 1000ml deionized water, extract with ethyl acetate (250mL×3 times), combine the organic phases and dry with anhydrous magnesium sulfate, filter and remove the solvent by vacuum distillation to obtain a crude product. Purify the crude product by silica gel column chromatography using n-heptane as the mobile phase to obtain Sub-c1 as a white solid (39.1g, yield 73%).

[0194] Referring to the intermediate Sub-c1, the reactant D shown in Table 3 was used instead of Sub-b1 to synthesize the intermediates Sub-c2 to Sub-c8.

[0195] Table 3: Synthesis of Intermediate Sub-c2 to Intermediate Sub-c8

[0196]

[0197] Synthesis of intermediate Sub-d1:

[0198]

[0199] Under nitrogen protection, add Sub-c1 (49.00 g, 119 mmol), Eaton's reagent (4.5 mL) and chlorobenzene (500 mL) to a 1000 mL three-necked flask in sequence, raise the temperature to reflux and continue stirring the reaction for 4 hours. When the reaction system reaches room temperature, pour the reaction solution into 1000 ml of deionized water, neutralize with saturated sodium hydroxide solution, and then extract with dichloromethane (250 mL × 3 times), combine the organic phases and dry with anhydrous magnesium sulfate, filter and remove the solvent by vacuum distillation to obtain a crude product. Use dichloromethane / n-heptane as the mobile phase to purify the crude product by silica gel column chromatography to obtain Sub-d1 solid (21.70 g, yield: 48%).

[0200] Referring to the synthesis of intermediate Sub-d1, reactant E shown in Table 4 was used instead of Sub-c1 to synthesize intermediates Sub-d2 to Sub-d8.

[0201] Table 4: Synthesis of Intermediate Sub-d2 to Intermediate Sub-d8

[0202]

[0203] Synthesis of intermediate Sub-e1:

[0204]

[0205] Under nitrogen protection, Sub-d1 (9.49 g, 25 mmol), 4-chlorophenylboronic acid (4.30 g, 27.5 mmol), palladium acetate (0.083 g, 0.5 mmol), 2-dicyclohexylphosphino-2',4',6'triisopropylbiphenyl (0.48 g, 1 mmol), tetrabutylammonium bromide (0.81 g, 2.5 mmol), potassium carbonate (6.91 g, 50 mmol) and toluene (100 mL), tetrahydrofuran (25 mL) and deionized water (25 mL) were added into a 250 mL three-necked flask in sequence, the temperature was raised to reflux, and the reaction was stirred overnight; after the system was cooled to room temperature, it was extracted with dichloromethane (100 mL×3 times), the organic phases were combined and dried over anhydrous magnesium sulfate, filtered and the solvent was distilled off under reduced pressure to obtain a crude product. The crude product was purified by silica gel column chromatography using dichloromethane / n-heptane as the mobile phase to obtain Sub-e1 as a white solid (7.18 g, yield: 63%).

[0206] Referring to the synthesis of intermediate Sub-e1, reactant F shown in Table 5 was used instead of 4-chlorophenylboronic acid to synthesize intermediates Sub-e2 to Sub-e5.

[0207] Table 5: Synthesis of Intermediate Sub-e2 to Intermediate Sub-e5

[0208]

[0209] Synthesis of compounds

[0210] Synthesis of compound 6:

[0211]

[0212] Under nitrogen protection, Sub-d1 (9.49 g, 25 mmol), RM-1 (9.22 g, 27.5 mmol), tris(dibenzylideneacetone)dipalladium (Pd2(dba)3, 0.916 g, 0.5 mmol), (2-dicyclohexylphosphine-2',4',6'triisopropylbiphenyl) (X-Phos, 0.95 g, 1 mmol), sodium tert-butoxide (t-BuONa, 9.61 g, 50 mmol) and xylene (xylene, 250 mL) were added to a 500 mL three-necked flask in sequence, the temperature was raised to reflux, and the reaction was stirred overnight; after the system was cooled to room temperature, it was extracted with dichloromethane (100 mL×3 times), the organic phases were combined and dried over anhydrous sodium sulfate, filtered and the solvent was removed by distillation under reduced pressure to obtain a crude product. The crude product was purified by silica gel column chromatography using n-heptane / dichloromethane as the mobile phase to obtain an off-white solid (13.91 g; yield: 82%, m / z = 679.23 [M+H] + ).

[0213] Referring to the synthesis of compound 6, reactant G shown in Table 6 was used to replace Sub-d1, and reactant H was used to replace RM-1 to synthesize the compounds of the present application in Table 6.

[0214] Table 6 Synthesis of compounds of the present application

[0215]

[0216]

[0217]

[0218]

[0219]

[0220]

[0221] The NMR data of some compounds are shown in Table 7 below

[0222] Table 7

[0223]

[0224] The embodiment of the present application also provides an organic electroluminescent device, including an anode, a cathode, and an organic layer between the anode and the cathode, wherein the organic layer includes the above-mentioned organic compound of the present application. The organic electroluminescent device of the present application is described in detail below through examples. However, the following examples are only examples of the present application, and do not limit the present application.

[0225] Example 1: Red organic electroluminescent device

[0226] First, the anode pretreatment is carried out through the following process: the thickness is On the ITO / Ag / ITO substrate, the surface is treated with UV ozone and O2:N2 plasma to increase the work function of the anode. The surface of the ITO substrate can also be cleaned with an organic solvent to remove impurities and oil stains on the surface of the ITO substrate.

[0227] On the experimental substrate (anode), PD:HT-5 was co-evaporated at an evaporation rate ratio of 2%:98% to form a film with a thickness of Then, HT-5 was vacuum-deposited on the hole injection layer to form a hole injection layer with a thickness of hole transport layer.

[0228] Compound HT-23 was vacuum-deposited on the hole transport layer to form a layer with a thickness of Holes adjustment layer.

[0229] On the hole adjustment layer, compound 6:RH-N:RD was co-evaporated at a ratio of 49%:49%:2% to form a layer with a thickness of Organic light-emitting layer (EML)

[0230] On the light-emitting layer, compound ET-1 and LiQ were co-evaporated at an evaporation rate ratio of 1:1 to form a layer with a thickness of Yb is evaporated on the electron transport layer to form an electron transport layer with a thickness of Then, magnesium (Mg) and silver (Ag) were mixed at a evaporation rate of 1:9 and vacuum evaporated on the electron injection layer to form a layer with a thickness of cathode.

[0231] In addition, compound CP-1 is vacuum-evaporated on the cathode to form a layer with a thickness of An organic cover layer (CPL) is formed to complete the manufacture of a red organic electroluminescent device.

[0232] Embodiments 2 to 44

[0233] An organic electroluminescent device was prepared by the same method as in Example 1, except that the compound shown in Table 8 below was used instead of Compound 6 in Example 1 when preparing the light-emitting layer.

[0234] Comparative Examples 1 to 3

[0235] An organic electroluminescent device was prepared by the same method as in Example 1, except that compound A, compound B and compound C were used to replace compound 6 in Example 1 when preparing the light-emitting layer.

[0236] Among them, when preparing each embodiment and comparative example, the compound structure used is as follows:

[0237]

[0238] The performance of the red organic electroluminescent devices prepared in Examples 1-44 and Comparative Examples 1-3 was tested. Specifically, at 10 mA / cm 2 The IVL performance of the device was tested under the conditions of T95 device life at 20mA / cm 2 The test was carried out under the conditions of , and the test results are shown in Table 8.

[0239] Table 8

[0240]

[0241]

[0242] Referring to Table 8 above, it can be seen that compared with Comparative Examples 1 to 3, when the compounds of the present application are used as the main material of the red organic electroluminescent device, the efficiency is at least increased by 11.4%, and the life span is at least increased by 12.9%. The reason is that the structure of the compounds of the present application contains the parent core structure of phenanthrobenzoxazole / thiazole, and the parent core is connected to aromatic amine compounds, which are respectively used as hole-transporting red light main materials. Among them, phenanthrobenzoxazole / thiazole has a large conjugated system, and after connecting its aromatic amine, it can enhance the intermolecular force and improve the carrier mobility of the compound. When the compounds of the present application are used as hole-transporting materials in hybrid main materials, the carrier balance in the light-emitting layer can be improved, the carrier recombination area can be widened, the exciton generation and utilization efficiency can be improved, and the luminous efficiency and life of the device can be improved.

Claims

1. An organic compound, characterized in that The organic compound has a structure shown in Formula 1: Wherein, one of X and Y is -O- or -S-, and the other is -N=; n1 is R 1 The number of R is selected from 0, 1 or 2; when n1 is greater than 1, any two R 1 Same or different; n2 is R 2 The number of R is selected from 0, 1 or 2; when n2 is greater than 1, any two R 2 Same or different; n3 is R 3 The number of is selected from 1, 2, 3 or 4; When n3 is 1, R 3 Having the structure shown in Formula 2, each R 1 , R 2 and R 4 Each is independently selected from deuterium, cyano, halogen, alkyl having 1 to 4 carbon atoms, deuterated alkyl having 1 to 4 carbon atoms, haloalkyl having 1 to 4 carbon atoms, aryl having 6 to 12 carbon atoms, deuterated aryl having 6 to 12 carbon atoms or heteroaryl having 5 to 12 carbon atoms; When n3 is greater than 1, R 3 One of them has the structure shown in Formula 2, and the other R 3 With each R 1 , R 2 and R 4 Each is independently selected from deuterium, cyano, halogen, alkyl having 1 to 4 carbon atoms, deuterated alkyl having 1 to 4 carbon atoms, haloalkyl having 1 to 4 carbon atoms, aryl having 6 to 12 carbon atoms, deuterated aryl having 6 to 12 carbon atoms or heteroaryl having 5 to 12 carbon atoms; n4 is R 4 The number of R is selected from 0, 1 or 2; when n4 is greater than 1, any two R 4 Same or different; L is selected from a single bond, a substituted or unsubstituted phenylene group, and a substituted or unsubstituted naphthylene group; L 1 , L 2 are the same or different and are each independently selected from a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, and a substituted or unsubstituted biphenylene group; L 1 , L 2 and the substituents in L are the same or different and are each independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl or phenyl; Ar 1 ,Ar 2 are the same or different and are each independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted dibenzothienyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted carbazolyl; Ar 3 is selected from substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted dibenzothienyl, substituted or unsubstituted dibenzofuranyl; Ar 1 ,Ar 2 and Ar 3 The substituents in are the same or different and are independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, cyclohexyl, phenyl, naphthyl or pentadeuterated phenyl.

2. The organic compound according to claim 1, characterized in that When n3 is greater than 1, the remaining R 3 With each R 1 , R 2 and R 4 Each is independently selected from deuterium, cyano, fluorine, methyl, ethyl, isopropyl, tert-butyl or phenyl.

3. The organic compound according to claim 1, characterized in that n3 is 1.

4. The organic compound according to claim 1, characterized in that Ar 1 and Ar 2 The same or different, and each independently selected from the group consisting of the following groups: Ar 3 Selected from the group consisting of:

5. The organic compound according to claim 1, characterized in that L is selected from a single bond or the following groups: L 1 and L 2 are the same or different, each independently selected from the group consisting of a single bond or the following groups:

6. The organic compound according to claim 1, characterized in that and The same or different, and each independently selected from the group consisting of the following groups:

7. The organic compound according to claim 1, characterized in that The structure shown in formula 2 Selected from the group consisting of:

8. The organic compound according to claim 1, wherein The compound is selected from the following structures:

9. An organic electroluminescent device, comprising an anode and a cathode disposed opposite to each other, and a functional layer disposed between the anode and the cathode; characterized in that: The functional layer contains the organic compound according to any one of claims 1 to 8.

10. The organic electroluminescent device according to claim 9, characterized in that: The functional layer includes an organic light-emitting layer, and the organic light-emitting layer includes the organic compound.

11. An electronic device, characterized in that The organic electroluminescent device comprises the organic electroluminescent device according to claim 9 or 10.

Citation Information

Patent Citations

  • Monoamine organic compound and organic electroluminescent device containing same

    CN115677686A

  • Novel compound for coating layer and organic light-emitting element comprising same

    CN115991668A