Organic compound, organic electroluminescent device, and electronic apparatus

Abstract

The present application relates to the technical field of organic electroluminescent materials, and provides an organic compound, an organic electroluminescent device comprising same, and an electronic apparatus. The organic compound has a structure as shown in formula 1 below. An arylamine compound of the present application comprises a phenanthrodibenzofuran parent nucleus structure. When the compound of the present application is used as a host material of a light-emitting layer, the carrier balance in the light-emitting layer can be improved, a carrier recombination region can be widened, exciton generation and utilization efficiency can be improved, the light-emitting efficiency of the device can be improved, and the service life of the device can be prolonged.

Description

Organic compounds, organic electroluminescent devices and electronic devices

[0001] Cross-reference to related applications

[0002] This application claims priority to Chinese Patent Application No. CN202410877681.3, filed on July 2, 2024, and Chinese Patent Application No. CN202411097269.6, filed on August 12, 2024, the contents of which are incorporated herein in their entirety. TECHNICAL FIELD

[0003] The present application relates to the technical field of organic electroluminescent materials, in particular to an organic compound, an organic electroluminescent device comprising the same and an electronic device. BACKGROUND

[0004] With the development of electronic technology and the progress of material science, the application range of electronic components and devices for realizing electroluminescence or photoelectric conversion is more and more extensive. An organic electroluminescent device (OLED) generally comprises a cathode and an anode arranged oppositely, and a functional layer arranged between the cathode and the anode. The functional layer is composed of multiple organic or inorganic film layers, and generally comprises an organic light-emitting layer, a hole transport layer, an electron transport layer, etc. When a voltage is applied to the cathode and the anode, an electric field is generated between the two electrodes. Under the action of the electric field, electrons on the cathode side move to the electroluminescent layer, and holes on the anode side also move to the electroluminescent layer. The electrons and holes combine in the electroluminescent layer to form excitons. The excitons in the excited state release energy to the outside, and then the electroluminescent layer emits light.

[0005] The most important problems in the existing organic electroluminescent devices are the service life and the efficiency. With the large-area display, the driving voltage is also increased, and the luminous efficiency and the current efficiency also need to be improved. Therefore, it is necessary to continue to develop new materials to further improve the performance of the organic electroluminescent device. SUMMARY

[0006] In view of the above problems existing in the prior art, the purpose of the present application is to provide an organic compound, an electronic element and an electronic device comprising the same, which is used in an organic electroluminescent device and can improve the performance of the device.

[0007] According to a first aspect of the present application, an organic compound is provided, which has a structure as shown in the following formula 1:

[0008] In formula 1, group A is selected from the following formula (A-1) or (A-2):

[0009] one of X and Y is O, and the other is a single bond;

[0010] R1, R2, and R3 are the same or different, and each is independently selected from deuterium, a cyano group, a halogen group, an alkyl group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, a deuterated alkyl group having 1 to 10 carbon atoms, a trialkylsilyl group having 3 to 12 carbon atoms, an aryl group having 6 to 20 carbon atoms, a deuterated aryl group having 6 to 20 carbon atoms, a heteroaryl group having 3 to 20 carbon atoms;

[0011] n1, n2, and n3 represent the number of substituents R1, R2, and R3, respectively, n1 is selected from 0, 1, 2, 3, 4, or 5; n2 is selected from 0, 1, 2, 3, or 4; and n3 is selected from 0, 1, 2, 3, or 4;

[0012] L, L1, L2, L3, and L4 are the same or different, and each is independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms;

[0013] Ar1, Ar2, Ar3, and Ar4 are the same or different, and each is independently selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms;

[0014] the substituents in L, L1, L2, L3, L4, Ar1, Ar2, Ar3, and Ar4 are the same or different, and each is independently selected from deuterium, a cyano group, a halogen group, an alkyl group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, a deuterated alkyl group having 1 to 10 carbon atoms, a trialkylsilyl group having 3 to 12 carbon atoms, an aryl group having 6 to 18 carbon atoms, a deuterated aryl group having 6 to 18 carbon atoms, a heteroaryl group having 3 to 12 carbon atoms, or a cycloalkyl group having 5 to 10 carbon atoms; optionally, any two adjacent substituents in Ar1, Ar2, Ar3, and Ar4 form a saturated or unsaturated 5- to 13-membered ring.

[0015] According to a second aspect of the present application, there is provided an organic electroluminescence device, comprising an anode and a cathode arranged oppositely, and a functional layer arranged between the anode and the cathode; the functional layer comprises the organic compound described above.

[0016] In some embodiments, the organic electroluminescence device comprises a red organic electroluminescence device.

[0017] According to a third aspect of the present application, there is provided an electronic device comprising the organic electroluminescence device of the second aspect.

[0018] The compound of the present application contains a mother nucleus structure of phenanthro dibenzofuran in the structure of the compound, and the mother nucleus structure is connected with a triazine group or an arylamine group to form an electron transport type light-emitting host material or a hole transport type light-emitting host material. On the one hand, the mother nucleus of phenanthro dibenzofuran has a special fusion mode, which ensures that the mother nucleus fragment has a suitable first excited triplet state energy level, which is suitable as a light-emitting host material fragment; on the other hand, the mother nucleus of phenanthro dibenzofuran has a large conjugated area, which helps to enhance the intermolecular interaction and improve the carrier mobility of the compound. The connection of the triazine or arylamine group with the mother nucleus helps to delocalize the electron cloud of the mother nucleus to the triazine group and the arylamine group, thereby improving the structural stability of the compound. When the compound of the present application is used as an electron transport type host material and a hole transport type host 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 efficiency of exciton generation and utilization can be improved, and the luminous efficiency and service life of the device can be improved. BRIEF DESCRIPTION OF DRAWINGS

[0019] The accompanying drawings are included to provide a further understanding of the present application, and constitute a part of the specification, and are used to explain the present application together with the specific embodiments described below, but do not constitute a limitation on the present application.

[0020] FIG. 1 is a schematic structural diagram of an organic electroluminescent device according to an embodiment of the present application.

[0021] FIG. 2 is a schematic structural diagram of an electronic device according to an embodiment of the present application.

[0022] Reference signs 100, anode 200, cathode 300, functional layer 310, hole injection layer 321, hole transport layer 322, light-emitting auxiliary layer 330, organic light-emitting layer 340, electron transport layer 350, electron injection layer 400, electronic device DETAILED DESCRIPTION

[0023] Exemplary embodiments will now be described more fully with reference to the accompanying drawings. However, exemplary embodiments can be implemented in various forms and should not be construed as limited to the examples set forth herein; rather, these examples are provided so that the present application will be more thorough and complete, and will fully convey the concept of exemplary embodiments to those skilled in the art. The described features, structures, or characteristics can be combined in one or more embodiments in any suitable manner. In the following description, numerous specific details are provided to give a sufficient understanding of embodiments of the present application.

[0024] In a first aspect, the present application provides an organic compound having a structure as shown in formula 1 below:

[0025] In formula 1, group A is selected from the following formula (A-1) or formula (A-2):

[0026] One of X and Y is O, and the other is a single bond;

[0027] R1, R2, and R3 are the same or different, and each is independently selected from deuterium, a cyano group, a halogen group, an alkyl group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, a deuterated alkyl group having 1 to 10 carbon atoms, a trialkylsilyl group having 3 to 12 carbon atoms, an aryl group having 6 to 20 carbon atoms, a deuterated aryl group having 6 to 20 carbon atoms, a heteroaryl group having 3 to 20 carbon atoms;

[0028] n1, n2, and n3 each represent the number of substituents R1, R2, and R3, respectively, n1 is selected from 0, 1, 2, 3, 4, or 5; n2 is selected from 0, 1, 2, 3, or 4; and n3 is selected from 0, 1, 2, 3, or 4;

[0029] L, L1, L2, L3, and L4 are the same or different, and each is independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms;

[0030] Ar1, Ar2, Ar3, and Ar4 are the same or different, and each is independently selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms;

[0031] The substituents in L, L1, L2, L3, L4, Ar1, Ar2, Ar3, and Ar4 are the same or different, and each is independently selected from deuterium, a cyano group, a halogen group, an alkyl group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, a deuterated alkyl group having 1 to 10 carbon atoms, a trialkylsilyl group having 3 to 12 carbon atoms, an aryl group having 6 to 18 carbon atoms, a deuterated aryl group having 6 to 18 carbon atoms, a heteroaryl group having 3 to 12 carbon atoms, or a cycloalkyl group having 5 to 10 carbon atoms; optionally, any two adjacent substituents in Ar1, Ar2, Ar3, and Ar4 form a saturated or unsaturated 5- to 13-membered ring.

[0032] In the present application, the term "optionally" or "optional" means that the event or circumstance described subsequently can or can not occur. For example, "optionally, any two adjacent substituents form a ring" means that the two substituents can form a ring or can not form a ring, i.e. including the scenario in which the two adjacent substituents form a ring and the scenario in which the 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 can exist independently. "Any two adjacent" can include two substituents on the same atom, or two substituents on two adjacent atoms; wherein when the two substituents are on the same atom, the two substituents and the atom to which they are commonly connected can form a saturated or unsaturated spiro ring; when the two substituents are on two adjacent atoms, the two substituents can be fused into a ring.

[0033] In the present application, the description "each of... is independently" and "each of... is independently" and "each of... is independently" can be interchangeable, and should be interpreted broadly, 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, chlorine, which means that formula Q-1 represents a benzene ring with q substituents R", each R" can be the same or different, and the options for each R" do not affect each other; formula Q-2 represents a biphenyl, each benzene ring has q substituents R", 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 for each R" do not affect each other.

[0034] In the present application, the term "substituted or unsubstituted" means that the functional groups described after the term can or can not have substituents (hereinafter, for the sake of description, the substituents are collectively referred to as Rc). For example, "substituted or unsubstituted aryl" means aryl with substituents Rc or aryl without substituents. The above-mentioned substituents, i.e. Rc, for example, can be deuterium, a halogen group, a cyano group, a heteroaryl group, an aryl group, a trialkylsilyl group, an alkyl group, a haloalkyl group, a cycloalkyl group, etc. The number of substitutions can be one or more.

[0035] In the present application, "a plurality of" means 2 or more, for example, 2, 3, 4, 5, 6, etc.

[0036] In the present application, saturated or unsaturated 5-13 membered ring refers to a ring containing 5-13 ring atoms; for example, but not limited to, cyclopentane, cyclohexane, benzene ring, fluorene ring, etc.

[0037] The hydrogen atoms in the structure of the compounds of the present application include various isotopes of the hydrogen element, such as hydrogen (H), deuterium (D), or tritium (T).

[0038] 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 L1 is a substituted arylene group having a carbon atom number of 12, the total number of carbon atoms of the arylene group and the substituents thereon is 12.

[0039] In the present application, an aryl group refers to an optional functional group or substituent derived from an aromatic carbocyclic ring. The aryl group can be a monocyclic aryl group (e.g., phenyl) or a polycyclic aryl group, in other words, the aryl group can be a monocyclic aryl group, a fused ring aryl group, two or more monocyclic aryl groups linked by carbon-carbon bonds, a monocyclic aryl group and a fused ring aryl group linked by carbon-carbon bonds, or two or more fused ring aryl groups linked by carbon-carbon bonds. That is, unless otherwise specified, two or more aromatic groups linked by carbon-carbon bonds can also be regarded as an aryl group of the present application. Among them, the fused ring aryl group can include, for example, a bicyclic fused aryl group (e.g., naphthyl), a tricyclic fused aryl group (e.g., phenanthryl, fluorenyl, anthryl), and the like. The aryl group does not contain heteroatoms such as B, N, O, S, P, Se, and Si. Examples of the aryl group can include, but are not limited to, phenyl, naphthyl, fluorenyl, spirobifluorenyl anthryl, phenanthryl, biphenyl, terphenyl, triphenylenyl pyrenyl, benzophenanthryl, chrysenyl, fluorenyl, spirobifluorenyl, etc.

[0040] In the present application, the arylene group refers to a divalent or multivalent group formed by further losing one or more hydrogen atoms from the aryl group.

[0041] In the present application, the terphenyl group includes

[0042] 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 thereon, for example, a substituted aryl group having a carbon atom number of 18 refers to the total number of carbon atoms of the aryl group and the substituents thereon being 18.

[0043] In the present application, the number of carbon atoms of a substituted or unsubstituted aryl (arylene) group can be 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 aryl group is a substituted or unsubstituted aryl group having a carbon atom number of 6 to 30; in other embodiments, the substituted or unsubstituted aryl group is a substituted or unsubstituted aryl group having a carbon atom number of 6 to 25; in other embodiments, the substituted or unsubstituted aryl group is a substituted or unsubstituted aryl group having a carbon atom number of 6 to 15.

[0044] In the present application, fluorenyl group can be substituted by one or more substituents. In the case where the above-mentioned fluorenyl group is substituted, the substituted fluorenyl group can be: etc., but is not limited thereto.

[0045] In the present application, as the substituent of L, L1, L2, L3, L4, Ar1, Ar2, Ar3and Ar4, aryl group, for example, but not limited to, phenyl, naphthyl, phenanthryl, biphenyl, fluorenyl, dimethylfluorenyl, etc.

[0046] In the present application, heteroaryl group refers to a monovalent aromatic ring or its derivative containing 1, 2, 3, 4, 5 or 6 heteroatoms in the ring, and the heteroatom can be one or more of B, O, N, P, Si, Se and S. The heteroaryl group can be a monocyclic heteroaryl group or a polycyclic heteroaryl group, in other words, the heteroaryl group can be a single aromatic ring system or a plurality of aromatic ring systems connected by carbon-carbon bond, and any of the aromatic ring systems is an aromatic monocyclic ring or an aromatic fused ring. For example, the heteroaryl group can include thienyl, furanyl, pyrrolyl, imidazolyl, thiazolyl, oxazolyl, oxadiazolyl, triazolyl, pyridyl, bipyridyl, pyrimidyl, triazinyl, acridinyl, pyridazinyl, pyrazinyl, quinolyl, quinazolinyl, quinoxalinyl, phenoxazinyl, phthalazinyl, pyridopyrimidyl, pyridopyrazinyl, pyrazinopyrazinyl, isoquinolyl, indolyl, carbazolyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothiophenyl, dibenzothiophenyl, thienothiophenyl, benzofuranyl, phenanthrolinyl, isoxazolyl, thiadiazolyl, phenothiazinyl, silylfluorenyl, dibenzofuranyl, and N-phenylcarbazolyl, N-pyridylcarbazolyl, N-methylcarbazolyl, etc., but is not limited thereto.

[0047] In the present application, the heteroaryl group referred to herein refers to a divalent or multivalent group formed by further losing one or more hydrogen atoms from the heteroaryl group.

[0048] In the present application, the number of carbon atoms of the substituted or unsubstituted heteroaryl (heteroarylene) group 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 group is a substituted or unsubstituted heteroaryl group having a total number of carbon atoms of 3 to 30; in other embodiments, the substituted or unsubstituted heteroaryl group is a substituted or unsubstituted heteroaryl group having a total number of carbon atoms of 3 to 18; in other embodiments, the substituted or unsubstituted heteroaryl group is a substituted or unsubstituted heteroaryl group having a total number of carbon atoms of 5 to 12.

[0049] In the present application, the heteroaryl group as a substituent of L, L1, L2, L3, L4, Ar1, Ar2, Ar3, and Ar4, for example, but not limited to, pyridyl group, carbazolyl group, quinolyl group, isoquinolyl group, phenanthrolinyl group, benzoxazolyl group, benzothiazolyl group, benzimidazolyl group, dibenzothiophenyl group, dibenzofuranyl group.

[0050] In the present application, the substituted heteroaryl group can be a heteroaryl group in which one or more hydrogen atoms is replaced with a group such as deuterium atom, halogen group, cyano group, aryl group, heteroaryl group, trialkylsilyl group, alkyl group, cycloalkyl group, haloalkyl group, and the like. It should be understood that the number of carbon atoms of the substituted heteroaryl group refers to the total number of carbon atoms of the heteroaryl group and the substituents on the heteroaryl group.

[0051] In the present application, the alkyl group having 1 to 10 carbon atoms can include straight chain alkyl group having 1 to 10 carbon atoms and branched chain alkyl group having 3 to 10 carbon atoms. The number of carbon atoms of the alkyl group, for example, can be 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, and specific examples of the alkyl group include, but are not limited to, methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, t-butyl group, n-pentyl group, isopentyl group, neopentyl group, n-hexyl group, and the like.

[0052] In the present application, the halogen group, for example, can be fluorine, chlorine, bromine, iodine.

[0053] In the present application, the number of carbon atoms of the deuterated alkyl group having 1 to 10 carbon atoms can be 1, 2, 3, 4, 5, 6, 7, 8, or 10. Specific examples of the deuterated alkyl group include, but are not limited to, trideuteromethyl group.

[0054] In the present application, the number of carbon atoms of the deuterated aryl group having 6 to 20 carbon atoms can be 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, or 20. Specific examples of the deuterated aryl group include, but are not limited to, penta-deuterophenyl group, tri-deuterophenyl group.

[0055] In the present application, specific examples of the trialkylsilyl group include, but are not limited to, trimethylsilyl group, triethylsilyl group, and the like.

[0056] In the present application, specific examples of the haloalkyl group include, but are not limited to, trifluoromethyl group.

[0057] In the present application, the number of carbon atoms of the cycloalkyl group having 3 to 10 carbon atoms, for example, can be 3, 4, 5, 6, 7, 8, 9, or 10. Specific examples of the cycloalkyl group include, but are not limited to, cyclopentyl group, cyclohexyl group, adamantyl group.

[0058] In the present application, the unpositioned bond refers to a single bond extending from the ring system which indicates that one end of the bond can be attached to any position in the ring system through which the bond extends, and the other end is attached to the remainder of the compound molecule. For example, as shown in the following formula (f), the naphthyl group represented by formula (f) is attached to the remainder of the molecule through two indefinite bonds that extend through the bicyclic ring system, and the meaning represented thereby includes any of the possible attachment modes shown in formulae (f-1) to (f-10):

[0059] For example, as shown in the following formula (X'), the dibenzofuranyl group represented by formula (X') is attached to the remainder of the molecule through one indefinite bond that extends from the middle of one of the phenyl rings, and the meaning represented thereby includes any of the possible attachment modes shown in formulae (X'-1) to (X'-4):

[0060] An indefinite substituent in the present application refers to a substituent that is attached through a single bond that extends from the center of a ring system, and indicates that the substituent can be attached 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 attached to the quinoline ring through one indefinite bond, and the meaning represented thereby includes any of the possible attachment modes shown in formulae (Y-1) to (Y-7):

[0061] In some embodiments, the compound of Formula 1 is selected from the structures represented by the following formulae (II-1) and (II-2):

[0062] In some embodiments, the compound of Formula 1 is selected from the structures represented by the following formulae (1-1) to (1-8):

[0063] In some embodiments, Ar1, Ar2, Ar3, and Ar4 are the same or different, and each is independently selected from substituted or unsubstituted aryl 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 substituted or unsubstituted heteroaryl having 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, or 24 carbon atoms.

[0064] In some embodiments, Ar1, Ar2, Ar3, and Ar4 are the same or different, and each is independently selected from substituted or unsubstituted aryl having 6 to 25 carbon atoms, and substituted or unsubstituted heteroaryl having 5 to 24 carbon atoms.

[0065] In some embodiments, the substituents in Ar1, Ar2, Ar3, and Ar4are the same or different, and each is independently selected from deuterium, a halogen group, a cyano group, a haloalkyl group having 1 to 4 carbon atoms, a deuterated alkyl group having 1 to 4 carbon atoms, an alkyl group having 1 to 4 carbon atoms, a cycloalkyl group having 5 to 10 carbon atoms, an aryl group having 6 to 15 carbon atoms, a heteroaryl group having 5 to 12 carbon atoms, a trialkylsilyl group having 3 to 8 carbon atoms, or a deuterated aryl group having 6 to 15 carbon atoms; optionally, any two adjacent substituents form a benzene ring or a fluorene ring.

[0066] In some embodiments, Ar1, Ar2, Ar3, and Ar4are the same or different, and each is independently selected from a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted spirobifluorenyl group, a substituted or unsubstituted triphenylenyl group, a substituted or unsubstituted pyrenyl group, a substituted or unsubstituted perylenyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted carbazolyl group.

[0067] In some embodiments, the substituents in Ar1, Ar2, Ar3, and Ar4are the same or different, and each is independently selected from deuterium, a halogen group, a cyano group, a haloalkyl group having 1 to 4 carbon atoms, a deuterated alkyl group having 1 to 4 carbon atoms, an alkyl group having 1 to 4 carbon atoms, a cycloalkyl group having 5 to 10 carbon atoms, an aryl group having 6 to 15 carbon atoms, a heteroaryl group having 5 to 12 carbon atoms, a trialkylsilyl group having 3 to 8 carbon atoms, or a deuterated aryl group having 6 to 15 carbon atoms; optionally, any two adjacent substituents form a benzene ring or a fluorene ring.

[0068] In some embodiments, Ar1, Ar2, Ar3, and Ar4are the same or different, and each is independently selected from the group consisting of:

[0069] In some embodiments, Ar1, Ar2, Ar3, and Ar4are the same or different, and each is independently selected from the group consisting of:

[0070] In some embodiments, L, L1, L2, L3, and L4are the same or different, and each is independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 15 carbon atoms, or a substituted or unsubstituted heteroarylene group having 12 to 18 carbon atoms.

[0071] In some embodiments, L, L1, L2, L3, and L4are the same or different, and each is 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, a substituted or unsubstituted heteroarylene group having 12, 13, 14, 15, 16, 17, or 18 carbon atoms.

[0072] In some embodiments, the substituents in L, L1, L2, L3, and L4are the same or different, and each is independently selected from deuterium, fluorine, cyano, an alkyl group having 1 to 5 carbon atoms, a trialkylsilyl group having 3 to 8 carbon atoms, a fluoroalkyl group having 1 to 4 carbon atoms, a deuterium alkyl group having 1 to 4 carbon atoms, a phenyl group, or a naphthyl group.

[0073] In some embodiments, L, L1, L2, L3, and L4are the same or different, and each is 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 dithiophenylene group, a substituted or unsubstituted difuranylene group, a substituted or unsubstituted fluorenylene group, a substituted or unsubstituted phenanthrylene group, a substituted or unsubstituted carbazolylene group.

[0074] In some embodiments, the substituents in L, L1, L2, L3, and L4are the same or different, and each is independently selected from deuterium, fluorine, cyano, a methyl group, an ethyl group, an isopropyl group, a tert-butyl group, a trifluoromethyl group, a trideuteromethyl group, a trimethylsilyl group, or a phenyl group.

[0075] In some embodiments, L is selected from the group consisting of a single bond or the following groups:

[0076] In some specific embodiments, L is selected from the group consisting of a single bond or the following groups:

[0077] In some embodiments, L1, L2, L3, and L4are the same or different, and each is independently selected from a single bond or the following groups:

[0078] In some specific embodiments, L1, L2, L3, and L4are the same or different, and each is independently selected from a single bond or the following groups:

[0079] In some embodiments, are the same or different, and each is independently selected from the group consisting of:

[0080] In some embodiments, group A is selected from the group consisting of:

[0081] In some embodiments, each R1, R2and R3is the same or different, and each is independently selected from hydrogen, deuterium, cyano, fluorine, trideuteromethyl, trimethylsilyl, trifluoromethyl, methyl, ethyl, isopropyl, tert-butyl, or phenyl.

[0082] In some embodiments, the organic compound is selected from the group consisting of the following compounds:

[0083] In a second aspect of the present application, an organic electroluminescent device is provided, comprising an anode, a cathode, and a functional layer disposed between the anode and the cathode; wherein the functional layer comprises the organic compound according to the first aspect of the present application.

[0084] The organic compound provided by the present application can be used to form at least one organic film layer in the functional layer, so as to improve the luminous efficiency and lifetime of the organic electroluminescent device.

[0085] In some embodiments, the functional layer comprises an organic light-emitting layer, and the organic light-emitting layer comprises the organic compound. The organic light-emitting layer can be composed of the organic compound provided by the present application, or can be composed of the organic compound provided by the present application and other materials.

[0086] According to a specific embodiment, the organic electroluminescent device is shown in FIG. 1. The organic electroluminescent device can comprise an anode 100, a hole injection layer 310, a hole transport layer 321, a light-emitting auxiliary layer (hole auxiliary layer) 322, an organic light-emitting layer 330, an electron transport layer 340, an electron injection layer 350, and a cathode 200, which are sequentially stacked.

[0087] In the present application, the anode 100 comprises an anode material, which is preferably a material with a large work function that facilitates hole injection into the functional layer. Specific examples of the anode material 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. In some embodiments, the organic electroluminescent device uses a transparent electrode comprising indium tin oxide (ITO) as the anode.

[0088] In the present application, the hole transport layer can comprise one or more hole transport materials, which can be selected from carbazole polymers, carbazole-linked triarylamine compounds, or other types of compounds, and can be selected from the following compounds or any combination thereof:

[0089] In one embodiment, the hole transport layer 321 can be composed of HT-1.

[0090] In one embodiment, the light-emitting auxiliary layer 322 is composed of HT-2.

[0091] In one embodiment, a hole injection layer 310 is further provided between the anode 100 and the hole transport layer 321 to enhance the ability of injecting holes into the hole transport layer 321. The hole injection layer 310 can be selected from benzidine derivatives, starburst arylamine compounds, phthalocyanine derivatives, or other materials, which are not specifically limited in the present application. The material of the hole injection layer 310 is, for example, selected from the following compounds or any combination thereof:

[0092] In one embodiment, the hole injection layer 310 is composed of PD and HT-1.

[0093] In the present application, the organic light-emitting layer 330 can be composed of a single light-emitting material, or can comprise a host material and a guest material (i.e., a dopant material). In one embodiment, the organic light-emitting layer 330 is composed of a host material and a guest material, and holes injected into the organic light-emitting layer 330 and electrons injected into the organic light-emitting layer 330 can recombine to form excitons in the organic light-emitting layer 330, the excitons transfer energy to the host material, the host material transfers energy to the guest material, and the guest material emits light.

[0094] In an embodiment, the host material of the organic light-emitting layer 330 can comprise a metal chelate compound, a bisstyryl derivative, an aromatic amine derivative, a dibenzofuran derivative, or other types of materials. Optionally, the host material comprises an organic compound of the present application.

[0095] In an embodiment, the guest material of the organic light-emitting layer 330 can be a compound having condensed aryl rings or derivatives thereof, a compound having heteroaryl rings or derivatives thereof, an aromatic amine derivative, or other materials, which are not particularly limited in the present application. The guest material is also referred to as a dopant or a dopant material. According to the type of light emission, it can be classified into a fluorescent dopant and a phosphorescent dopant. Specific examples of the phosphorescent dopant include, but are not limited to,

[0096] In an embodiment of the present application, the organic electroluminescent device is a red organic electroluminescent device. In an embodiment, the host material of the organic light-emitting layer 330 comprises an organic compound of the present application. The guest material is, for example, RD-1.

[0097] In an embodiment, the host material of the organic light-emitting layer 330 comprises an organic compound of the present application and (RH-P). In another embodiment, the host material of the organic light-emitting layer 330 comprises an organic compound of the present application and

[0098] In an embodiment of the present application, the organic electroluminescent device is a green organic electroluminescent device. In a more specific embodiment, the host material of the organic light-emitting layer 330 comprises an organic compound of the present application.

[0099] In an embodiment, the electron transport layer 340 can be a single layer structure or a multi-layer structure, which can comprise one or more electron transport materials selected from, but not limited to, BTB, LiQ, a benzimidazole derivative, an oxadiazole derivative, a quinoxaline derivative, or other electron transport materials, which are not particularly limited in the present application. The material of the electron transport layer 340 comprises, but is not limited to, the following compounds:

[0100] In an embodiment of the present application, the electron transport layer 340 can be composed of ET-1 and LiQ.

[0101] In the present application, the cathode 200 can include a cathode material, which is a material with a small work function that facilitates electron injection into the functional layer. Specific examples of the cathode material include, but are not limited to, a metal such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or an alloy thereof; or a multi-layered material such as LiF / Al, Liq / Al, LiO2 / Al, LiF / Ca, LiF / Al, and BaF2 / Ca. Alternatively, a metal electrode including magnesium and silver can be included as the cathode.

[0102] In one embodiment, an electron injection layer 350 is further provided 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 can include an inorganic material such as an alkali metal sulfide, an alkali metal halide, or the like, or can include a complex of an alkali metal and an organic material. In one embodiment of the present application, the electron injection layer 350 can include ytterbium (Yb).

[0103] The third aspect of the present application provides an electronic device including the organic electroluminescent device according to the second aspect of the present application.

[0104] In one embodiment, as shown in FIG. 2, the electronic device provided is an electronic device 400 including the organic electroluminescent device described above. The 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, a computer screen, a cell phone screen, a television, electronic paper, an emergency lighting lamp, an optical module, and the like.

[0105] The synthesis method of the organic compound of the present application will be specifically described below in connection with the synthesis examples, but the present disclosure is not limited in any way by this.

[0106] Synthesis Examples

[0107] Those skilled in the art will recognize that the chemical reactions described in the present application can be used to practice the present application with a wide variety of organic compounds and that other methods for preparing compounds of the present application are also considered within the scope of the present application. For example, the synthesis of those non-exemplified compounds according to the present application can be successfully performed by a skilled person by employing the methods described in the present application, by using other known reagents instead of those that are described in the present application, or by making routine modifications to reaction conditions. The compounds of the present application that are not mentioned in the present application are prepared from commercially available starting materials by using the synthetic methods described in the present application.

[0108] Synthesis of Sub-a1:

[0109] Into a 250 mL three-necked flask, 3-bromo-1-benzofuran (9.85 g, 50 mmol), bis(pinacolato)diboron (14.0 g, 55 mmol), potassium acetate (10.8 g, 110 mmol) and 1,4-dioxane (100 mL) were sequentially added under nitrogen atmosphere. The stirring was started and the system was heated until it reached 40 °C. Then, tris(dibenzylideneacetone)dipalladium (Pd2(dba)3, 0.46 g, 0.50 mmol) and 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl (XPhos, 0.48 g, 1.0 mmol) were rapidly added and the system was heated until it reached reflux. The reaction was stirred overnight. After the system was cooled to room temperature, 100 mL of water was added and the system was stirred for 30 min. The system was filtered under reduced pressure and the filter cake was washed with deionized water until it was neutral. Then, the filter cake was washed with 50 mL of absolute ethanol to obtain a gray solid. The crude product was washed with n-heptane once and then dissolved in 100 mL of toluene. The catalyst was removed by passing the solution through a silica gel column. The solvent was removed by concentration to obtain Sub-a1 as a white solid (8.18 g, 67% yield).

[0110] Following the procedure described for the synthesis of Sub-a1, the intermediates Sub-a2 were synthesized using the reactants A shown in Table 1 instead of 3-bromo-1-benzofuran.

[0111] Table 1: Synthesis of Sub-a2

[0112] Synthesis of Sub-b1:

[0113] Into a 500 mL three-necked flask, Sub-a1 (13.42 g, 55 mmol), 2-bromo-5- chlorobenzaldehyde (10.97 g, 50 mmol), tetrakis(triphenylphosphine)palladium (0.58 g, 0.5 mmol), tetrabutylammonium bromide (TBAB, 1.61 g, 5 mmol), anhydrous sodium carbonate (10.60 g, 100 mmol), toluene (140 mL), absolute ethanol (35 mL) and deionized water (35 mL) were sequentially added under nitrogen atmosphere. The stirring was started and the system was heated until it reached reflux. The reaction was stirred for 8 h. After the system was cooled to room temperature, the system was extracted with dichloromethane (100 mL x 3 times). The organic phases were combined and dried over anhydrous magnesium sulfate. The solvent was removed by filtration under reduced pressure to obtain the 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 (8.21 g, 64% yield).

[0114] Following the procedure described for the synthesis of Sub-b1, the intermediates Sub-b2 were synthesized using the reactants B shown in Table 2 instead of Sub-a1.

[0115] Table 2: Synthesis of Sub-b2

[0116] Synthesis of Sub-c1:

[0117] Into a 500 mL three-necked flask, Sub-b1 (33.37 g, 130 mmol), potassium tert-butoxide (18.10 g, 161 mmol) and anhydrous tetrahydrofuran (170 mL) were sequentially added under nitrogen atmosphere. The system was cooled to -15 °C and kept for 30 min. Then Sub-c1 (33.88 g, 119 mmol), Eaton’s reagent (4.5 mL) and chlorobenzene (330 mL) were sequentially added under nitrogen atmosphere. The system was heated to reflux and kept for 4 h. After the reaction system was cooled to room temperature, the reaction solution was poured into 500 mL deionized water and neutralized with saturated sodium hydroxide solution. Then the solution was extracted with dichloromethane (250 mL x 3 times). The combined organic phase was dried with anhydrous magnesium 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 dichloromethane / n-heptane as the mobile phase to obtain white solid Sub-d1 (19.24 g, yield 64%).

[0118] Referring to the synthesis method of Sub-c1, intermediate Sub-c2 was synthesized by using reactant C shown in Table 3 to replace Sub-b1.

[0119] Table 3: Synthesis of Sub-c2

[0120] Synthesis of Sub-d1:

[0121] Into a 500 mL three-necked flask, Sub-b1 (33.37 g, 130 mmol), potassium tert-butoxide (18.10 g, 161 mmol) and anhydrous tetrahydrofuran (170 mL) were sequentially added under nitrogen atmosphere. The system was cooled to -15 °C and kept for 30 min. Then Sub-c1 (33.88 g, 119 mmol), Eaton’s reagent (4.5 mL) and chlorobenzene (330 mL) were sequentially added under nitrogen atmosphere. The system was heated to reflux and kept for 4 h. After the reaction system was cooled to room temperature, the reaction solution was poured into 500 mL deionized water and neutralized with saturated sodium hydroxide solution. Then the solution was extracted with dichloromethane (250 mL x 3 times). The combined organic phase was dried with anhydrous magnesium 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 dichloromethane / n-heptane as the mobile phase to obtain white solid Sub-d1 (19.24 g, yield 64%).

[0122] Referring to the synthesis method of Sub-d1, intermediate Sub-d2 was synthesized by using reactant D shown in Table 4 to replace Sub-c1.

[0123] Table 4: Synthesis of Sub-d2

[0124] Synthesis of Sub-e1:

[0125] Into a 250 mL three-necked flask, Sub-dl (12.63 g, 50 mmol), bis(pinacolato)diboron (14.0 g, 55 mmol), potassium acetate (10.8 g, 110 mmol) and 1,4-dioxane (120 mL) were sequentially added under nitrogen atmosphere. The stirring and heating were started, and the system was warmed to 40 °C. Then tris(dibenzylideneacetone)dipalladium (Pd2(dba)3, 0.46 g, 0.50 mmol) and 2-dicyclohexylphosphino-2',4',6' triisopropyl biphenyl (XPhos, 0.48 g, 1.0 mmol) were quickly added. The system was warmed to reflux, and the reaction was stirred overnight. After the system was cooled to room temperature, 200 mL of water was added, and the system was stirred thoroughly for 30 min. The system was filtered under reduced pressure, and the filter cake was washed with deionized water until neutral, and then washed with 50 mL of anhydrous ethanol. A gray solid was obtained. The crude product was washed with n-heptane once, and then dissolved in 200 mL of toluene. The catalyst was removed by silica gel column, and the solvent was removed by concentration. A white solid, Sub-el (12.40 g, 72% yield), was obtained.

[0126] Referring to the synthesis of Sub-el, the reactant E shown in Table 5 was used to replace Sub-dl to synthesize intermediate Sub-e2.

[0127] Table 5: Synthesis of Sub-e2

[0128] Synthesis of Sub-fl:

[0129] Into a 500 mL three-necked flask, Sub-el (18.93 g, 55 mmol), 2-bromo-4-chlorobenzaldehyde (10.97 g, 50 mmol), tetrakis(triphenylphosphine)palladium (0.58 g, 0.5 mmol), tetrabutylammonium bromide (TBAB, 1.61 g, 5 mmol), anhydrous sodium carbonate (10.60 g, 100 mmol), toluene (180 mL), anhydrous ethanol (45 mL) and deionized water (45 mL) were sequentially added under nitrogen atmosphere. The stirring and heating were started, and the system was warmed to reflux for 8 h. After the system was cooled to room temperature, the system was extracted with dichloromethane (100 mL x 3 times), and the organic phases were combined and dried with anhydrous magnesium sulfate. The system was filtered, and the solvent was removed by distillation under reduced pressure. The crude product was purified by silica gel column chromatography using dichloromethane / n-heptane as the mobile phase. A white solid, Sub-fl (12.84 g, 72% yield), was obtained.

[0130] Referring to the synthesis of Sub-fl, the reactant F shown in Table 6 was used to replace Sub-el, and the reactant G was used to replace 2-bromo-4-chlorobenzaldehyde to synthesize intermediates Sub-f2 to Sub-f8.

[0131] Table 6: Synthesis of Sub-f2 to Sub-f8

[0132] Synthesis of Sub-g1 :

[0133] Into a 500 mL three-necked flask, (methoxymethyl)triphenylphosphonium chloride (51.25 g, 149.5 mmol), potassium tert-butoxide (18.10 g, 161 mmol) and anhydrous tetrahydrofuran (230 mL) were added successively under nitrogen atmosphere. The system was cooled to -15 °C and kept for 30 min. Then Sub-f1 (46.38 g, 130 mmol) was weighed and dissolved in anhydrous tetrahydrofuran (230 mL). The solution was added slowly into the reaction system by constant pressure dropping funnel, keeping the temperature at -15 °C during the dropping process. After the dropping process, the reaction was kept stirring at -15 °C for 1 h. Then the reaction system was allowed to warm up to room temperature. The reaction was extracted with dichloromethane (150 mL x 3 times). The organic phases were combined and dried over anhydrous magnesium sulfate. After filtration, the solvent was removed by distillation under reduced pressure to give a crude product. The crude product was purified by silica gel column chromatography using n-heptane / dichloromethane as the mobile phase to give Sub-g1 (31.0 g, yield 62%) as a gray-white solid.

[0134] Referring to the synthesis method of Sub-g1, intermediates Sub-g2 to Sub-g8 were synthesized by using reactant H shown in Table 7 to replace Sub-f1.

[0135] Table 7: Synthesis of Sub-g2 to Sub-g8

[0136] Synthesis of Sub-h1 :

[0137] Into a 1000 mL three-necked flask, Sub-g1 (45.80 g, 119 mmol), Eaton’s reagent (4.5 mL) and chlorobenzene (450 mL) were added successively under nitrogen atmosphere. The reaction was kept stirring at reflux for 4 h. After the reaction system was cooled to room temperature, the reaction solution was poured into 500 mL deionized water. The solution was neutralized with saturated sodium hydroxide solution. Then the solution was extracted with dichloromethane (250 mL x 3 times). The organic phases were combined and dried over anhydrous magnesium sulfate. After filtration, the solvent was removed by distillation under reduced pressure to give a crude product. The crude product was purified by silica gel column chromatography using dichloromethane / n-heptane as the mobile phase to give Sub-h1 (22.67 g, yield 54%) as a white solid.

[0138] Referring to the synthesis method of Sub-h1, intermediates Sub-h2 to Sub-h8 were synthesized by using reactant J shown in Table 8 to replace Sub-g1.

[0139] Table 8: Synthesis of Sub-h2 to Sub-h8

[0140] Synthesis of Sub-h9:

[0141] Into a 100 mL three-necked flask was added Sub-hl (8.82 g, 25 mmol) and 200 mL benzene-D6 under nitrogen atmosphere, and the mixture was warmed to 60 °C. Then triflic acid (22.51 g, 150 mmol) was added, and the mixture was warmed to boiling and stirred for 24 h. After the reaction mixture was cooled to room temperature, 50 mL of heavy water was added, and the mixture was stirred for 10 min. Then the reaction mixture was neutralized with saturated aqueous K3PO4solution. The organic layer was extracted with dichloromethane (50 mL x 3), and the combined organic phase was dried over anhydrous sodium sulfate. After filtration, the solvent was removed by distillation under reduced pressure to give a crude product. The crude product was purified by silica gel column chromatography using n-heptane / dichloromethane as the mobile phase to give Sub-h9 (7.13 g, 78% yield) as a white solid.

[0142] Synthesis of Sub-jl:

[0143] Into a 500 mL three-necked flask was added Sub-hl (17.64 g, 50 mmol), bis(pinacolato)diboron (14.0 g, 55 mmol), potassium acetate (10.8 g, 110 mmol), and 1,4-dioxane (180 mL) under nitrogen atmosphere. After stirring and heating, the mixture was warmed to 40 °C, and then tris(dibenzylideneacetone)dipalladium (Pd2(dba)3, 0.46 g, 0.50 mmol) and 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl (XPhos, 0.48 g, 1.0 mmol) were rapidly added. The mixture was warmed to reflux and stirred overnight. After the mixture was cooled to room temperature, 200 mL of water was added, and the mixture was stirred for 30 min. The mixture was filtered under reduced pressure, and the filter cake was washed with deionized water until neutral, and then washed with 50 mL of anhydrous ethanol. The crude product was washed with n-heptane once, and then dissolved in 200 mL of toluene. The catalyst was removed by passing the solution through a silica gel column. After concentration, Sub-jl (14.88 g, 67% yield) was obtained as a white solid.

[0144] Referring to the synthesis method of Sub-jl, intermediates Sub-j2 to Sub-j9 were synthesized by using the reactants K shown in Table 9 instead of Sub-hl.

[0145] Table 9: Synthesis of Sub-j2 to Sub-j9

[0146] Synthesis of Sub-kl:

[0147] Into a 500 mL three-necked flask, Sub-jl (22.21 g, 50 mmol), 4-bromo chlorobenzene (9.57 g, 50 mmol), tetrakis(triphenylphosphine)palladium (0.58 g, 0.5 mmol), anhydrous sodium carbonate (10.60 g, 100 mmol), toluene (220 mL), anhydrous ethanol (55 mL) and deionized water (55 mL) were added successively under nitrogen atmosphere. Stirring and heating were started and the temperature was raised to reflux for 8 h. After the system was cooled to room temperature, dichloromethane (100 mL x 3 times) was used to extract the product. The organic phase was combined and dried over anhydrous magnesium sulfate. After filtration, the solvent was removed by distillation under reduced pressure to obtain a crude product. Silica gel column chromatography was performed on the crude product using dichloromethane / n-heptane as the mobile phase to obtain white solid Sub-kl (16.72 g, yield 78%).

[0148] Referring to the synthesis of Sub-kl, Sub-jl was replaced by reactant L and reactant M was replaced by 4-bromo chlorobenzene in Table 10 to synthesize Sub-k2 to Sub-k9.

[0149] Table 10: Synthesis of Sub-k2 to Sub-k9

[0150] Synthesis Example 1: Synthesis of Compound A-4

[0151] Into a 250 mL three-necked flask, Sub-jl (11.66 g, 26.25 mmol), RM-1 (8.95 g, 25 mmol), palladium acetate (42 mg, 0.25 mmol), 2-dicyclohexylphosphino-2',4',6' triisopropyl biphenyl (XPhos, 0.24 g, 0.5 mmol), anhydrous potassium carbonate (6.9 g, 50 mmol), tetrabutylammonium bromide (0.8 g, 2.5 mmol), toluene (100 mL), tetrahydrofuran (25 mL) and deionized water (25 mL) were added successively under nitrogen atmosphere. Stirring and heating were started and the temperature was raised to reflux for 16 h. After the system was cooled to room temperature, dichloromethane (100 mL x 3 times) was used to extract the product. The organic phase was combined and dried over anhydrous magnesium sulfate. After filtration, the solvent was removed by distillation under reduced pressure to obtain a crude product. Silica gel column chromatography was performed on the crude product using dichloromethane / n-heptane as the mobile phase to obtain white solid A-4 (12.95 g, yield 81%, m / z = 640.31 [M+H]). +

[0152] Referring to the synthesis of compound A-4, Sub-jl was replaced by reactant N and reactant O was replaced by RM-1 in Table 11 to synthesize the compounds of the present application in Table 11. ​

[0153] Table 11: Synthesis of compounds of the application

[0154] Synthesis example 53: Synthesis of compound B-1:

[0155] Into a 250 mL three-necked flask, RM-2 (8.04 g, 25 mmol), Sub-h1 (9.70 g, 27.5 mmol), tris(dibenzylideneacetone)dipalladium (0.916 g, 0.5 mmol), 2-dicyclohexylphosphino-2',4',6' triisopropyl biphenyl (XPhos, 0.95 g, 1 mmol), sodium tert-butoxide (9.61 g, 50 mmol) and xylene (120 mL) were sequentially added under nitrogen atmosphere, the reaction was heated to reflux and stirred overnight. After the system was cooled to room temperature, dichloromethane (100 mL x 3) was used to extract, the organic phases were combined and dried over anhydrous sodium sulfate, the solvent was removed by distillation under reduced pressure after filtration, the crude product was obtained. Silica gel column chromatography was performed on the crude product using n-heptane / dichloromethane as the mobile phase, white solid B-1 (13.23 g; yield 83%, m / z = 638.24 [M+H] + ) was obtained.

[0156] Referring to the synthesis of compound B-1, reactant P shown in Table 12 was used instead of Sub-h1, and reactant Q was used instead of RM-2, to synthesize the compounds of the application in Table 12.

[0157] Table 12: Synthesis of compounds of the application

[0158] NMR of compound A-20: 1H-NMR (400MHz, CD2Cl2) δppm: 9.46 (s, 1H), 9.04 (d, 1H), 8.79 (d, 2H), 8.75 (d, 1H), 8.62 (d, 1H), 8.51(d,1H),8.31(d,1H),8.24-8.07(m,5H),7.92-7.81(m,6H),7.77(d,1H),7.71-7.40(m,9H);

[0159] NMR of compound B-161: 1 H-NMR (400MHz, CD2Cl2) δppm: 8.78(d,1H),8.60(d,1H),8.42(d,1H),8.34(d,1H),8.18(d,1H),8.01(d,1H),7 .96(d,1H),7.91-7.80(m,3H),7.58-7.25(m,14H),7.12(d,1H),6.94(s,1H),6.87-6.79(m,2H),6.44(d,1H).

[0160] Fabrication and evaluation of organic electroluminescent devices:

[0161] Example 1: Fabrication of a red organic electroluminescent device

[0162] 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. Alternatively, organic solvents can be used to clean the surface of the ITO substrate to remove impurities and oil stains.

[0163] On the experimental substrate (anode), PD:HT-1 was co-deposited at a deposition rate of 2%:98% to form a thickness of [missing information]. A hole injection layer (HIL) is formed. Then, HT-1 is vacuum-deposited on the hole injection layer to form a thickness of [missing information]. A hole transport layer. Compound HT-2 is vacuum-deposited onto the hole transport layer to form a layer with a thickness of [missing information]. The light-emitting auxiliary layer.

[0164] Next, on the light-emitting auxiliary layer, compounds A-4:RH-P:RD-1 were co-deposited in a ratio of 49%:49%:2% to form a layer with a thickness of [missing information]. The red light emitting layer (EML).

[0165] On the light-emitting layer, compound ET-1 and LiQ are co-deposited at a 1:1 evaporation rate ratio to form... A thick electron transport layer (ETL) is formed on the electron transport layer, Yb is evaporated to form an electron injection layer (EIL) with a thickness of Then, magnesium (Mg) and silver (Ag) are mixed at a ratio of 1:9 and evaporated on the electron injection layer to form a cathode with a thickness of .

[0166] In addition, a CP with a thickness of is evaporated on the cathode to form a cover layer, thereby completing the manufacture of the red organic electroluminescent device.

[0167] Examples 2-52

[0168] An organic electroluminescent device is prepared by the same method as in Example 1, except that the compound in Table 13 below is used instead of Compound A-4 in the preparation of the light-emitting layer.

[0169] Comparative Examples 1-4

[0170] An organic electroluminescent device is prepared by the same method as in Example 1, except that Compound A, Compound B, Compound C, and Compound D are used instead of Compound A-4 in the preparation of the light-emitting layer, respectively.

[0171] In each of the examples and comparative examples, the structures of the main materials used are as follows.

[0172] The red organic electroluminescent devices prepared in Examples 1-52 and Comparative Examples 1-4 are tested for performance, and the IVL performance of the devices is tested at 10 mA / cm 2 , the T95 device lifetime is tested at 20 mA / cm 2 , and the test results are shown in Table 13.

[0173] Table 13

[0174] As can be seen from Table 13 above, compared with Comparative Examples 1-4 using Compound A-Compound D, the luminous efficiency of the devices of Examples 1-52 using the compound of the present application as the electron transport type host material in the light-emitting layer host material of the red organic electroluminescent device is at least 13.2% higher, and the T 95 95 device lifetime is at least 12.8% higher.

[0175] Example 53: Red Organic Electroluminescent Device

[0176] The anode is first pretreated by the following process: a layer of LiF with a thickness of The ITO / Ag / ITO substrate is surface treated by UV ozone and O2:N2 plasma to increase the work function of the anode, or the ITO substrate surface is cleaned by organic solvent to remove impurities and oil on the ITO substrate surface.

[0177] The PD:HT-1 is co-evaporated on the experimental substrate (anode) at a ratio of 2%:98% to form a hole injection layer (HIL) with a thickness of 100 A. The HT-1 is vacuum evaporated on the hole injection layer to form a hole transport layer (HTL) with a thickness of 200 A. The compound HT-2 is vacuum evaporated on the hole transport layer to form a light-emitting auxiliary layer (LA) with a thickness of 100 A.

[0178] Next, the compound B-1:RH-N:RD-1 is co-evaporated on the light-emitting auxiliary layer at a ratio of 49%:49%:2% to form a red light-emitting layer (EML) with a thickness of 200 A.

[0179] The compound ET-1 and LiQ are co-evaporated on the light-emitting layer at a ratio of 1:1 to form an electron transport layer (ETL) with a thickness of 200 A. Yb is evaporated on the electron transport layer to form an electron injection layer (EIL) with a thickness of 100 A. Mg and Ag are mixed at a ratio of 1:9 and vacuum evaporated on the electron injection layer to form a cathode with a thickness of 200 A.

[0180] In addition, a CP with a thickness of 200 A is vacuum evaporated on the cathode to form a cover layer, thereby completing the manufacture of the red organic electroluminescent device. Examples 54-127

[0181] The organic electroluminescent device is prepared by the same method as in Example 53, except that the compound Y in Table 14 below is used instead of the compound B-1 in Example 53 when the light-emitting layer is prepared.

[0182] Comparative Examples 5-8

[0183] The organic electroluminescent device is prepared by the same method as in Example 53, except that the compound F, the compound G, the compound H, and the compound I are used instead of the compound B-1 in Example 53 when the light-emitting layer is prepared, respectively.

[0184] In the preparation of each of the examples and comparative examples, the compounds used have the following structures.

[0185] ​​​​

[0186] The red organic electroluminescent devices prepared in Examples 53-127 and Comparative Examples 5-8 were tested for performance, specifically for IVL performance at 10 mA / cm 2 T95 device lifetime at 20 mA / cm 2 was tested, and the results are shown in Table 14.

[0187] Table 14

[0188] As can be seen from Table 14, compared to Comparative Examples 5-8 using compounds F-I, the luminescent efficiency of the devices of Examples 53-127 using the compounds of the present application as hole transport type host material in the light-emitting layer host material of the red organic electroluminescent device was increased by at least 10.4%, and the T 95 lifetime was increased by at least 12.9%.

[0189] The preferred embodiments of the present application are described in detail above with reference to the accompanying drawings, but the present application is not limited to the specific details of the above-described embodiments, and various simple modifications can be made to the technical solutions of the present application within the scope of the technical concept of the present application, and these simple modifications all belong to the protection scope of the present application.

Claims

1. An organic compound characterized in that, The organic compound has a structure represented by the following Formula 1. In formula 1, the group A is selected from the following formula (A-1) or (A-2): one of X and Y is O, and the other is a single bond; R1, R2, and R3are the same or different, and each is independently selected from deuterium, a cyano group, a halogen group, an alkyl group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, a deuterated alkyl group having 1 to 10 carbon atoms, a trialkylsilyl group having 3 to 12 carbon atoms, an aryl group having 6 to 20 carbon atoms, a deuterated aryl group having 6 to 20 carbon atoms, a heteroaryl group having 3 to 20 carbon atoms; n1, n2, and n3 represent the number of substituents R1, R2, and R3, respectively, n1 is selected from 0, 1, 2, 3, 4, or 5; n2 is selected from 0, 1, 2, 3, or 4; n3 is selected from 0, 1, 2, 3, or 4; L, L1, L2, L3, and L4are the same or different, and each is independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms; Ar1, Ar2, Ar3, and Ar4are the same or different, and each is independently selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms; the substituents in L, L1, L2, L3, L4, Ar1, Ar2, Ar3, and Ar4are the same or different, and each is independently selected from deuterium, a cyano group, a halogen group, an alkyl group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, a deuterated alkyl group having 1 to 10 carbon atoms, a trialkylsilyl group having 3 to 12 carbon atoms, an aryl group having 6 to 18 carbon atoms, a deuterated aryl group having 6 to 18 carbon atoms, a heteroaryl group having 3 to 12 carbon atoms, or a cycloalkyl group having 5 to 10 carbon atoms; optionally, any two adjacent substituents in Ar1, Ar2, Ar3, and Ar4form a saturated or unsaturated 5- to 13-membered ring.

2. The organic compound according to claim 1, wherein Ar1, Ar2, Ar3, and Ar4are the same or different, and each is independently selected from a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthryl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted spirobifluorenyl group, a substituted or unsubstituted triphenylenyl group, a substituted or unsubstituted pyrenyl group, a substituted or unsubstituted perylenyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted carbazolyl group; optionally, the substituents in Ar1, Ar2, Ar3, and Ar4are the same or different, and each is independently selected from deuterium, fluorine, a cyano group, a trideuteromethyl group, a trimethylsilyl group, a trifluoromethyl group, a cyclopentyl group, a cyclohexyl group, an adamantyl group, a methyl group, an ethyl group, an isopropyl group, a tert-butyl group, a phenyl group, a naphthyl group, a pyridyl group, a dibenzofuranyl group, a dibenzothiophenyl group, or a carbazolyl group; optionally, any two adjacent substituents in Ar1, Ar2, Ar3, and Ar4form a benzene ring or a fluorene ring.

3. The organic compound according to claim 1 or 2, wherein L, L1, L2, L3, and L4 are the same or different, and each is 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 dithiophenylene group, a substituted or unsubstituted difuranylene group, a substituted or unsubstituted fluorenylene group, a substituted or unsubstituted phenanthrylene group, a substituted or unsubstituted carbazolylene group; Optionally, the substituents in L, L1, L2, L3, and L4 are the same or different, and each is independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, trideuteromethyl, trimethylsilyl, or phenyl.

4. The organic compound according to any one of claims 1 to 3, wherein Ar1, Ar2, Ar3, and Ar4are the same or different and each independently selected from the group consisting of:

5. The organic compound according to any one of claims 1 to 4, wherein L is selected from the group consisting of a single bond or the following groups: Optionally, L1, L2, L3and L4are the same or different and each is independently selected from the group consisting of a single bond or:

6. The organic compound according to any one of claims 1 to 5, wherein identical or different and each independently selected from the group consisting of:

7. The organic compound according to any one of claims 1 to 6, wherein The group A in formula 1 is selected from the group consisting of:

8. The organic compound according to any one of claims 1 to 7, wherein The compound of formula 1 is selected from the group consisting of the following structures of formulae (1-1) to (1-8):

9. The organic compound according to any one of claims 1 to 8, wherein Each of R1, R2, and R3 is the same or different, and each is independently selected from hydrogen, deuterium, cyano, fluorine, trideuteromethyl, trimethylsilyl, trifluoromethyl, methyl, ethyl, isopropyl, tert-butyl, or phenyl.

10. The organic compound according to any one of claims 1 to 9, wherein The organic compound is selected from the group consisting of:

11. An organic electroluminescence device comprising an anode and a cathode disposed opposite to each other, and a functional layer provided between the anode and the cathode; characterized in that, The functional layer comprises the organic compound according to any one of claims 1 to 10. Optionally, the functional layer comprises a light-emitting layer, and the light-emitting layer comprises the organic compound.

12. An electronic device, comprising: The organic electroluminescent device according to claim 11. The organic electroluminescent device according to claim 11.

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