Organic compound, composition, organic electroluminescent device and electronic device

Abstract

The invention belongs to the technical field of organic electroluminescence, and relates to an organic compound, a composition using the organic compound, an organic electroluminescence device and an electronic device, the organic compound has a structure as shown in a formula 1, and when the organic compound is used in the organic electroluminescence device, the performance of the organic electroluminescence device can be remarkably improved. # imgabs0 #

Description

Technical Field

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

[0002] With the development of electronic technology and the progress of materials science, the application scope of electronic components for realizing electroluminescence is becoming more and more extensive. Such electronic components generally include a cathode and an anode arranged relatively to each other, 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 includes an organic light-emitting layer, a hole transport layer located between the organic light-emitting layer and the anode, and an electron transport layer located between the organic light-emitting layer and the cathode. Taking an organic electroluminescent device as an example, it generally includes an anode, a hole transport layer, an organic light-emitting layer, an electron transport layer and a cathode stacked in sequence. 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 organic light-emitting layer, and the holes on the anode side also move toward the organic light-emitting layer. The electrons and holes combine in the organic light-emitting layer to form excitons, and the excitons are in an excited state and release energy outward, thereby causing the organic light-emitting layer to emit light outward.

[0003] The prior art discloses a host material that can be used to prepare an organic light-emitting layer in an organic electroluminescent device. However, it is still necessary to continue to develop new materials to further improve the performance of the organic electroluminescent device. Summary of the invention

[0004] To solve the above problems, the purpose of the present application is to provide an organic compound and a composition comprising the organic compound, an organic electroluminescent device and an electronic device, wherein the organic compound can improve the performance of the organic electroluminescent device and the electronic device, such as reducing the driving voltage of the device and improving the efficiency and life of the device.

[0005] In a first aspect of the present application, an organic compound is provided, wherein the organic compound has a structure as shown in Formula 1:

[0006]

[0007] Wherein, X is selected from C(R1R2), O or S;

[0008] R1 and R2 are the same or different and are independently selected from an alkyl group having 1 to 5 carbon atoms and a deuterated alkyl group having 1 to 5 carbon atoms;

[0009] L, L1 and L2 are the same or different and are independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 20 carbon atoms;

[0010] Ar1 and Ar2 are the same or different and are independently selected from substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, and substituted or unsubstituted carbazolyl groups;

[0011] The substituents in L, L1, L2, Ar1 and Ar2 are the same or different and are independently selected from deuterium, cyano, halogen group, alkyl group having 1 to 10 carbon atoms, halogenated alkyl group having 1 to 10 carbon atoms, deuterated alkyl group having 1 to 10 carbon atoms, aryl group having 6 to 20 carbon atoms, deuterated aryl group having 6 to 20 carbon atoms, trialkylsilyl group having 3 to 12 carbon atoms, halogenated aryl group having 6 to 20 carbon atoms or cycloalkyl group having 3 to 10 carbon atoms.

[0012] In a second aspect of the present application, a composition is provided, which comprises the first compound disclosed in the first aspect of the present application and a second compound having a structure shown in Formula 2 or Formula 3.

[0013] The third 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 organic compound disclosed in the first aspect of the present application or the composition disclosed in the second aspect of the present application.

[0014] In a fourth aspect of the present application, an electronic device is provided, comprising the organic electroluminescent device disclosed in the third aspect of the present application.

[0015] The core structure of the organic compound of the present application is a dibenzofuran / dibenzothiophene / fluorenyl group connected to a triazine group, and in the dibenzofuran / dibenzothiophene / fluorenyl group, the benzene ring not connected to the triazine group is fully deuterated, and the other benzene ring is unsubstituted. This regioselective substitution method makes the dibenzofuran / dibenzothiophene / fluorenyl group asymmetric deuterated, which can effectively improve the stability of the molecular structure, and can further reduce the molecular symmetry, thereby significantly improving the photoelectric stability and film-forming properties of the material. The organic compound of the present application has good carrier transport characteristics, energy transfer characteristics and photoelectric stability, and is suitable for use as a main material of the light-emitting layer in an organic electroluminescent device. The organic electroluminescent device using it as the main material has significantly improved life characteristics while maintaining a low driving voltage and high luminous efficiency.

[0016] Other features and advantages of the present application will be described in detail in the subsequent detailed description. BRIEF DESCRIPTION OF THE DRAWINGS

[0017] 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.

[0018] Figure 1It is a schematic structural diagram of an organic electroluminescent device of the present application.

[0019] Figure 2 It is a structural schematic diagram of an electronic device of the present application.

[0020] Reference numerals

[0021] 100, anode 200, cathode 300, functional layer 310, hole injection layer

[0022] 320, hole transport layer 330, hole auxiliary layer 340, organic light emitting layer 350, electron transport layer

[0023] 360. Electron injection layer 400. Electronic device DETAILED DESCRIPTION

[0024] In view of the above-mentioned 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 comprising the organic compound, wherein the organic compound can improve the performance of the organic electroluminescent device and the electronic device, such as reducing the driving voltage of the device and improving the efficiency and life of the device.

[0025] In a first aspect of the present application, an organic compound is provided, wherein the organic compound has a structure as shown in Formula 1:

[0026]

[0027] Wherein, X is selected from C(R1R2), O or S;

[0028] R1 and R2 are the same or different and are independently selected from an alkyl group having 1 to 5 carbon atoms and a deuterated alkyl group having 1 to 5 carbon atoms;

[0029] L, L1 and L2 are the same or different and are independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 20 carbon atoms;

[0030] Ar1 and Ar2 are the same or different and are independently selected from substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, and substituted or unsubstituted carbazolyl groups;

[0031] The substituents in L, L1, L2, Ar1 and Ar2 are the same or different and are independently selected from deuterium, cyano, halogen group, alkyl group having 1 to 10 carbon atoms, halogenated alkyl group having 1 to 10 carbon atoms, deuterated alkyl group having 1 to 10 carbon atoms, aryl group having 6 to 20 carbon atoms, deuterated aryl group having 6 to 20 carbon atoms, trialkylsilyl group having 3 to 12 carbon atoms, halogenated aryl group having 6 to 20 carbon atoms or cycloalkyl group having 3 to 10 carbon atoms.

[0032] In the present application, the description methods used "each...independently is" and "...respectively independently is" and "...each independently is" can be interchanged and should be understood in a broad sense. It can mean that in different groups, the specific options expressed by the same symbols do not affect each other, or it can mean that in the same group, the specific options expressed by the same symbols do not affect each other.

[0033] For example, Wherein, each q is independently 0, 1, 2 or 3, and each R" is independently selected

[0034] From hydrogen, deuterium, fluorine, chlorine", its meaning is: formula Q-1 means that there are q substituents R" on the benzene ring, each R" can be the same or different, and the options of each R" do not affect each other; formula Q-2 means that there are q substituents R" on each benzene ring of biphenyl, the number q of R" substituents on the two benzene rings can be the same or different, each R" can be the same or different, and the options of each R" do not affect each other.

[0035] 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, cyano, halogen group, alkyl, haloalkyl, deuterated alkyl, aryl, deuterated aryl, haloaryl, cycloalkyl, trialkylsilyl, etc. The number of substitutions can be 1 or more.

[0036] In the present application, "plurality" means more than 2, for example, 2, 3, 4, 5, 6, etc.

[0037] 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 12 carbon atoms, the total number of carbon atoms of the arylene group and the substituents thereon is 12.

[0038] 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 groups connected by carbon-carbon bond conjugation, a monocyclic aryl and a condensed ring aryl connected by carbon-carbon bond conjugation, and two or more condensed ring aryl groups connected by carbon-carbon bond conjugation. That is, unless otherwise specified, two or more aromatic groups connected by carbon-carbon 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, anthracenyl, phenanthrenyl, biphenyl, terphenyl, triphenylene, peryl, benzo[9,10]phenanthrenyl, pyrenyl, benzofluoranthenyl, In the present application, the arylene group refers to a divalent group formed by further losing a hydrogen atom from an aryl group.

[0039] 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.

[0040] In the present application, the carbon number of the substituted or unsubstituted aryl group may be 6, 10, 12, 13, 14, 15, 16, 17, 18, 20, 24, 25 or 30. In some embodiments, the substituted or unsubstituted aryl group is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, in other embodiments, the substituted or unsubstituted aryl group is a substituted or unsubstituted aryl group having 6 to 25 carbon atoms, in other embodiments, the substituted or unsubstituted aryl group is a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, and in other embodiments, the substituted or unsubstituted aryl group is a substituted or unsubstituted aryl group having 6 to 12 carbon atoms.

[0041] In the present application, examples of aryl groups as substituents for Ar1, Ar2, L1, and L2 include, but are not limited to, phenyl, naphthyl, and biphenyl.

[0042] 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 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.

[0043] In the present application, the number of carbon atoms of the substituted or unsubstituted heteroaryl group can be selected from 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29 or 30. In some embodiments, the substituted or unsubstituted heteroaryl group is a substituted or unsubstituted heteroaryl group having 5 to 20 carbon atoms, and in other embodiments, the substituted or unsubstituted heteroaryl group is a substituted or unsubstituted heteroaryl group having 12 to 18 carbon atoms.

[0044] 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, trialkylsilyl 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.

[0045] 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 may be, 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.

[0046] In the present application, the halogen group may be, for example, fluorine, chlorine, bromine, or iodine.

[0047] In the present application, specific examples of the haloalkyl group include, but are not limited to, trifluoromethyl.

[0048] In the present application, specific examples of deuterated alkyl groups include, but are not limited to, trideuterated methyl groups.

[0049] In the present application, a deuterated aryl group refers to an aryl group containing at least one deuterium substituent. Specific examples of the deuterated aryl group include, but are not limited to, pentadeuterated phenyl and pentadeuterated biphenyl.

[0050] In the present application, the carbon number of the cycloalkyl group having 3 to 10 carbon atoms may be, 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.

[0051] In this application, no single bond extending from the ring system is involved in the positioning of the connecting bond. 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, and the meaning represented by it includes any possible connection mode shown in formula (f-1) to formula (f-10).

[0052]

[0053] 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 its meaning includes any possible connection method shown in formulas (X'-1) to (X'-4).

[0054]

[0055] In some embodiments of the present application, in Formula 1, R1 and R2 are both methyl groups.

[0056] In some embodiments of the present application, the organic compound represented by Formula 1 is selected from the structures represented by Formula 1-1, Formula 1-2 or Formula 1-3:

[0057]

[0058] In some specific embodiments of the present application, the organic compound represented by Formula 1 is selected from the structure represented by Formula A, Formula B, Formula C, Formula D, Formula E, Formula F, Formula G or Formula H:

[0059]

[0060] In some embodiments of the present application, the organic compound represented by Formula 1 is selected from the structure represented by Formula A, Formula B, Formula C or Formula D.

[0061] In some embodiments of the present application, in Formula 1, L, L1 and L2 are the same or different, and are independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 12 carbon atoms.

[0062] Optionally, in Formula 1, the substituents in L, L1 and L2 are the same or different and are independently selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 5 carbon atoms or a phenyl group.

[0063] In other embodiments of the present application, in Formula 1, L, L1 and L2 are the same or different, and are 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.

[0064] Optionally, in Formula 1, the substituents in L, L1 and L2 are the same or different, and are independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl or phenyl.

[0065] Optionally, in Formula 1, L1 and L2 are the same or different and are independently selected from a single bond or the following groups:

[0066]

[0067] Specifically, in Formula 1, L1 and L2 are the same or different and are independently selected from a single bond or the following groups:

[0068]

[0069]

[0070] In some embodiments of the present application, in Formula 1, Ar1 and Ar2 are the same or different and are independently selected from a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, or a substituted or unsubstituted carbazole group.

[0071] Optionally, the substituents in Ar1 and Ar2 are the same or different and are independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, phenyl or pentadeuterated phenyl.

[0072] In other embodiments of the present application, in Formula 1, Ar1 and Ar2 are the same or different, and are independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted terphenyl, and substituted or unsubstituted carbazolyl.

[0073] Optionally, the substituents in Ar1 and Ar2 are the same or different and are independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, phenyl or pentadeuterated phenyl.

[0074] Optionally, in Formula 1, Ar1 and Ar2 are the same or different and are independently selected from the following groups:

[0075]

[0076] In some more specific embodiments, in Formula 1, Ar1 and Ar2 are the same or different and are independently selected from the group consisting of the following groups:

[0077]

[0078]

[0079] In some embodiments of the present application, in Formula 1, and The same or different, are independently selected from the following groups:

[0080]

[0081] In some more specific embodiments, in Formula 1, and The same or different, are independently selected from the following groups:

[0082]

[0083]

[0084] In some embodiments of the present application, in Formula 1 Selected from the group consisting of:

[0085]

[0086]

[0087] In some embodiments of the present application, the organic compound is selected from the compound as shown in claim 7.

[0088] The second aspect of the present application also provides a composition comprising a first compound and a second compound;

[0089] The first compound has a structure shown in Formula 1, and the second compound is selected from a structure shown in Formula 2 or Formula 3:

[0090]

[0091] wherein each R3, each R4, each R5, each R6, each R7, each R8 and each R9 are the same or different and are independently selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 5 carbon atoms, an aryl group having 6 to 20 carbon atoms, a deuterated aryl group having 6 to 20 carbon atoms, a halogenated aryl group having 6 to 20 carbon atoms or a heteroaryl group having 3 to 20 carbon atoms;

[0092] n3 is the number of R3, selected from 0, 1, 2, 3 or 4. When n3 is greater than 2, any two R3 are the same or different;

[0093] n4 is the number of R4, selected from 0, 1, 2 or 3. When n4 is greater than 2, any two R4 are the same or different;

[0094] n5 is the number of R5, selected from 0, 1, 2 or 3. When n5 is greater than 2, any two R5 are the same or different;

[0095] n6 is the number of R6, selected from 0, 1, 2, 3 or 4. When n6 is greater than 2, any two R6 are the same or different;

[0096] n7 is the number of R7, selected from 0, 1, 2, 3 or 4. When n7 is greater than 2, any two R7 are the same or different;

[0097] n8 is the number of R8, selected from 0, 1 or 2. When n8 is greater than 2, any two R8 are the same or different;

[0098] n9 is the number of R9, selected from 0, 1, 2, 3 or 4. When n9 is greater than 2, any two R9 are the same or different;

[0099] L3, L4, L5 and L6 are the same or different and are 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;

[0100] Ar3, Ar4, Ar5 and Ar6 are the same or different and are independently selected from substituted or unsubstituted aryl groups having 6 to 30 carbon atoms and substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms;

[0101] The substituents in L3, L4, L5, L6, Ar3, Ar4, Ar5 and Ar6 are the same or different and are independently selected from deuterium, cyano, halogen group, alkyl group having 1 to 10 carbon atoms, halogenated alkyl group having 1 to 10 carbon atoms, deuterated alkyl group having 1 to 10 carbon atoms, aryl group having 6 to 20 carbon atoms, deuterated aryl group having 6 to 20 carbon atoms, halogenated aryl group having 6 to 20 carbon atoms or cycloalkyl group having 3 to 10 carbon atoms.

[0102] In some embodiments of the present application, the second compound is selected from the structure shown in Formula 2-1 or Formula 3-1:

[0103]

[0104] In some embodiments of the present application, in the second compound, L3, L4, L5 and L6 are the same or different, and are independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 18 carbon atoms, and a substituted or unsubstituted heteroarylene group having 12 to 18 carbon atoms.

[0105] Optionally, in the second compound, the substituents in L3, L4, L5 and L6 are the same or different, and are independently selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 5 carbon atoms, or a phenyl group.

[0106] Further optionally, in the second compound represented by Formula 2, L3 and L4 are the same or different and are independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 12 carbon atoms, and a substituted or unsubstituted heteroarylene group having 12 to 18 carbon atoms.

[0107] Further optionally, in the second compound represented by Formula 3, L5 and L6 are the same or different, and are independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 18 carbon atoms.

[0108] In some embodiments of the present application, in the second compound shown in Formula 2, L3 and L4 are the same or different, and are 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 carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, and a substituted or unsubstituted dibenzothiophenyl group.

[0109] Optionally, in the second compound shown in Formula 2, the substituents in L3 and L4 are the same or different, and are independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl or phenyl.

[0110] In some other embodiments of the present application, in the second compound shown in Formula 3, L5 and L6 are the same or different, and are independently selected from a single bond, a substituted or unsubstituted phenylene, a substituted or unsubstituted naphthylene, a substituted or unsubstituted biphenylene, and a substituted or unsubstituted terphenylene.

[0111] Optionally, in the second compound shown in Formula 3, the substituents in L5 and L6 are the same or different, and are independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl or phenyl.

[0112] In some embodiments of the present application, in the second compound represented by Formula 2, L3 and L4 are the same or different, and are independently selected from a single bond or the following groups:

[0113]

[0114] Specifically, in the second compound represented by Formula 2, L3 and L4 are the same or different and are independently selected from a single bond or the following groups:

[0115]

[0116] In some embodiments of the present application, in the second compound represented by Formula 3, L5 and L6 are the same or different, and are independently selected from a single bond or the following groups:

[0117]

[0118] Specifically, in the second compound represented by Formula 3, L5 and L6 are the same or different and are independently selected from a single bond or the following groups:

[0119]

[0120] In some embodiments of the present application, in the second compound, Ar3, Ar4, Ar5 and Ar6 are the same or different, and are independently selected from substituted or unsubstituted aryl groups having 6 to 24 carbon atoms and substituted or unsubstituted heteroaryl groups having 12 to 24 carbon atoms.

[0121] Optionally, in the second compound, the substituents in Ar3, Ar4, Ar5 and Ar6 are the same or different, and are independently selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 5 carbon atoms, a phenyl group, a monodeuterated phenyl group or a pentadeuterated phenyl group.

[0122] In some other embodiments of the present application, in the second compound, Ar3, Ar4, Ar5 and Ar6 are the same or different, and are independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted quaterphenyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl.

[0123] Optionally, in the second compound, the substituents in Ar3, Ar4, Ar5 and Ar6 are the same or different and are independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, phenyl, monodeuterated phenyl or pentadeuterated phenyl.

[0124] Further optionally, in the second compound shown in Formula 2, Ar3 and Ar4 are the same or different, and are independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl.

[0125] Further optionally, in the second compound shown in Formula 3, Ar5 and Ar6 are the same or different, and are independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted quadriphenyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophene.

[0126] In some embodiments of the present application, in the second compound represented by Formula 2, Ar3 and Ar4 are the same or different and are independently selected from the group consisting of the following groups:

[0127]

[0128]

[0129] Specifically, in the second compound shown in Formula 2, Ar3 and Ar4 are the same or different and are independently selected from a single bond or the following groups:

[0130]

[0131] In some embodiments of the present application, in the second compound represented by Formula 3, Ar5 and Ar6 are the same or different and are independently selected from the group consisting of the following groups:

[0132]

[0133]

[0134] Specifically, in the second compound shown in Formula 3, Ar5 and Ar6 are the same or different and are independently selected from a single bond or the following groups:

[0135]

[0136]

[0137] In some embodiments of the present application, the second compound shown in Formula 2 and The same or different, are independently selected from the following groups:

[0138]

[0139] Specifically, in the second compound shown in Formula 2 and The same or different, are independently selected from the following groups:

[0140]

[0141]

[0142] In some embodiments of the present application, the second compound shown in Formula 3 and The same or different, are independently selected from the following groups:

[0143]

[0144] Specifically, in the second compound shown in Formula 3 and The same or different, are independently selected from the following groups:

[0145]

[0146]

[0147] In some embodiments of the present application, the second compound represented by Formula 2 is selected from the compounds represented by A1 to B108 in claim 14.

[0148] In some embodiments of the present application, the second compound represented by Formula 3 is selected from the compounds represented by a1 to h78 in claim 14.

[0149] The present application does not particularly limit the relative contents of the two types of compounds in the composition provided in the second aspect, and can be selected according to the specific application of the organic electroluminescent device. Generally, the evaporation rate ratio (%) of the composition can be 1:99, 20:80, 30:70, 40:60, 45:65, 50:50, 55:45, 60:40, 70:30, 80:20, 99:1, etc.

[0150] In some preferred embodiments of the present application, the composition consists of a first compound and a second compound, and a evaporation rate ratio (%) of the composition is 40:60, 45:65, 50:50, 55:45, 60:40.

[0151] The present application also provides the use of the composition as a main material of a light-emitting layer of an organic electroluminescent device.

[0152] The third aspect of the present application also provides an organic electroluminescent device, which includes an anode and a cathode arranged opposite to each other, and at least one functional layer between the anode and the cathode, and the functional layer contains the organic compound represented by Formula 1 of the present application or a composition containing a first compound and a second compound.

[0153] In one embodiment of the present application, the functional layer comprises an organic light-emitting layer, and the organic light-emitting layer comprises an organic compound represented by Formula 1 of the present application.

[0154] In one embodiment of the present application, the functional layer comprises an organic light-emitting layer, and the organic light-emitting layer comprises a composition comprising a first compound and a second compound provided in the present application.

[0155] In one embodiment of the present application, the organic electroluminescent device is a phosphorescent device.

[0156] In a specific embodiment of the present application, the organic electroluminescent device is a green organic electroluminescent device.

[0157] In some embodiments of the present application, the organic electroluminescent device includes an anode (ITO substrate), a hole transport layer, a hole auxiliary layer, an organic light-emitting layer, an electron transport layer, an electron injection layer, a cathode (Mg-Ag mixture) and an organic covering layer in sequence.

[0158] In a specific embodiment of the present application, Figure 1 As shown, the organic electroluminescent device of the present application includes an anode 100, a cathode 200, and at least one functional layer 300 between the anode layer and the cathode layer, and the functional layer 300 includes a hole injection layer 310, a hole transport layer 320, a hole auxiliary layer 330, an organic light-emitting layer 340, an electron transport layer 350 and an electron injection layer 360.

[0159] Optionally, the anode 100 includes the following anode material, which is preferably 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 comprising indium tin oxide (indium tin oxide) (ITO) as an anode is included.

[0160] Optionally, the hole transport layer 320 may include one or more hole transport materials, and the hole transport material may be selected from carbazole polymers, carbazole-linked triarylamine compounds or other types of compounds, which are not specifically limited in the present application. For example, in some embodiments of the present application, the hole transport layer 320 is composed of HT-1.

[0161] Optionally, the hole auxiliary layer 330 may include one or more hole transport materials, and the hole transport material may be selected from carbazole polymers, carbazole-linked triarylamine compounds or other types of compounds, which are not specifically limited in the present application. For example, in some embodiments of the present application, the hole auxiliary layer 330 is composed of HT-2 or HT-3.

[0162] Optionally, the organic light-emitting layer 340 may be composed of a single light-emitting material, or may include a host material and a guest material. Optionally, the organic light-emitting layer 340 is composed of a host material and a guest material, and holes and electrons injected into the organic light-emitting layer 330 may be recombined in the organic light-emitting layer 340 to form excitons, and the excitons transfer energy to the host material, and the host material transfers energy to the guest material, thereby enabling the guest material to emit light.

[0163] The guest material of the organic light-emitting layer 340 may 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 particular limitation thereto.

[0164] In some embodiments of the present application, in a green organic electroluminescent device, the organic light-emitting layer 340 comprises the organic compound described in the present application, the second compound and the guest material GD-1.

[0165] 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, and the electron transport material may be selected from benzimidazole derivatives, oxadiazole derivatives, quinoxaline derivatives or other electron transport materials, and the present application does not make any special restrictions on this. For example, in some embodiments of the present application, the electron transport layer 350 may be composed of ET-1 and LiQ.

[0166] Optionally, cathode 200 includes a cathode material that is a material with a small work function that facilitates electron injection into the functional layer. Specific examples of cathode materials include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead or alloys thereof; or multilayer materials such as LiF / Al, Liq / Al, LiO2 / Al, LiF / Ca, LiF / Al and BaF2 / Ca, but are not limited thereto. Preferably, a metal electrode comprising silver and magnesium is included as the cathode.

[0167] 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. In some embodiments of the present application, the hole injection layer 310 may be composed of NDP-9 and HT-1.

[0168] Optionally, an electron injection layer 360 may be provided between the cathode 200 and the electron transport layer 350 to enhance the ability to inject electrons into the electron transport layer 350. The electron injection layer 360 may include inorganic materials such as alkali metal sulfides and alkali metal halides, or may include a complex of an alkali metal and an organic substance. In some embodiments of the present application, the electron injection layer 360 may include ytterbium (Yb).

[0169] A fourth aspect of the present application also provides an electronic device, which includes the organic electroluminescent device described in the present application.

[0170] For example, Figure 2 As shown, the electronic device provided in the present application is a first electronic device 400, and the first electronic device 400 includes any one of the organic electroluminescent devices described in the above organic electroluminescent device embodiments. The electronic device can be 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. Since the first electronic device 400 has the above organic electroluminescent device, it has the same beneficial effects, and the present application will not repeat them here.

[0171] The present application will be described in detail below in conjunction with embodiments; however, the following description is intended to explain the present application rather than to limit the scope of the present application in any way.

[0172] Synthesis of intermediate a-II-1:

[0173]

[0174] Under nitrogen protection, 1-bromo-2-methoxybenzene-3,4,5,6-d4 (60.0 g; 314.0 mmol) and THF (600 mL) were added to a round-bottom flask, and the mixture was cooled to -80 to -90 °C and n-butyl lithium (22.1 g; 345.4 mmol) was added dropwise. After the addition was completed, the mixture was kept warm for 1 hour. Trimethyl borate (39.1 g; 376.8 mmol) was added dropwise to the reaction solution. After the addition was completed, the mixture was kept warm for 1 hour and then naturally warmed to room temperature and stirred overnight. Hydrochloric acid (2 mol / L) was added to the reaction solution to adjust the pH to neutral, deionized water was added, the solution was separated, the organic phase was washed with water and dried with anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The obtained crude product was slurried with n-heptane to obtain a white solid product aI-1 (31.8 g; yield: 65%).

[0175]

[0176] The intermediate aI-1 (30.0 g; 192.3 mmol), 1-bromo-3-chloro-2-fluorobenzene (40.3 g; 192.3 mmol), tetrakis(triphenylphosphine)palladium (11.1 g; 9.6 mmol), potassium carbonate (53.2 g; 384.6 mmol), tetrabutylammonium bromide (0.6 g; 1.9 mmol), toluene (240 mL), ethanol (120 mL) and deionized water (60 mL) were added to a round-bottom flask. Under nitrogen protection, the mixed solution was heated to 78°C and stirred for 10 hours; the reaction solution was cooled to room temperature, toluene was added for extraction, the organic phases were combined, dried with anhydrous magnesium sulfate, filtered, and the solvent was removed under reduced pressure; the crude product was purified by silica gel column chromatography using a dichloromethane / n-heptane system to obtain a white solid intermediate a-II-1 (32.4 g; yield: 70%).

[0177] Synthesis of intermediate a-IV-1:

[0178]

[0179] Under nitrogen protection, the intermediate a-II-1 (30.0g; 124.6mmol) and dichloromethane (300ml) were added to a round-bottom flask, cooled to 0°C under stirring, and 1.0M boron tribromide solution (49.0; 186.9mmol) was added dropwise, and the system temperature was kept at 0°C. After the dropwise addition, the temperature was kept at 0°C for half an hour, and the reaction was completed after the temperature was naturally raised to room temperature and stirred for 5 hours. The reaction was completed. When the reaction was completed, the reaction solution was cooled to 0°C, and 0.8L of saturated sodium thiosulfate aqueous solution was slowly added dropwise over 30 minutes. Water was then added thereto, and extracted with dichloromethane, the separated organic phase was washed with water and then dried with anhydrous magnesium sulfate, and the solvent was removed under high temperature and reduced pressure conditions; the obtained crude product was purified by silica gel column chromatography using a dichloromethane / n-heptane system to obtain a solid intermediate a-III-1 (24.0g; yield: 85%).

[0180]

[0181] The intermediate a-III-1 (24.0 g; 105.9 mmol) was dissolved in 120 ml of N-methyl-2-pyrrolidone (NMP) under nitrogen atmosphere, and potassium carbonate (29.3; 211.8 mmol) was added thereto. Under nitrogen protection, the mixture was heated to 110°C and stirred for 10 hours. The reaction solution was cooled to room temperature, toluene was added for extraction, the organic phases were combined, dried with anhydrous magnesium sulfate, filtered, and the solvent was removed under reduced pressure; the crude product was purified by silica gel column chromatography using a dichloromethane / n-heptane system to obtain a white solid intermediate a-IV-1 (16.2 g; yield: 74%).

[0182] Referring to the synthesis method of intermediate a-IV-1, reactant A is used to replace 1-bromo-3-chloro-2-fluorobenzene to synthesize the intermediate shown in structure 2 in Table 1 below:

[0183] Table 1

[0184]

[0185] Synthesis of intermediate a-1:

[0186]

[0187] The intermediate a-IV-1 (15.0 g; 72.6 mmol), biboric acid pinacol ester (27.6 g; 108.9 mmol), tris [dibenzylideneacetone] dipalladium (0.6 g; 0.7 mmol), 2-dicyclohexylphosphine-2', 4', 6'-triisopropylbiphenyl (0.7 g; 1.4 mmol), KOAc (14.2 g; 145.2 mmol), 1,4-dioxane (150 mL) were added, and the mixture was refluxed at 100 ° C for 12 hours. When the reaction was completed, dichloromethane and water were used for extraction. MgSO4 was used to dry and concentrate the organic layer, and the crude product was purified by silica gel column chromatography using dichloromethane and n-heptane as eluents to obtain a white solid compound. It was further purified by recrystallization with dichloromethane and n-heptane to obtain the intermediate a-1 (13.8 g; yield: 64%).

[0188] Referring to the synthesis method of intermediate a-1, reactant B is used to replace intermediate a-IV-1 to synthesize the intermediates shown in Table 2 below:

[0189] Table 2

[0190]

[0191]

[0192] Synthesis of compound AA1:

[0193]

[0194] The intermediate a-1 (9.1 g; 30.5 mmol), 2-(4-biphenyl)-4-chloro-6-phenyl-1,3,5-triazine (10.0 g; 29.1 mmol), tetrakis(triphenylphosphine)palladium (0.7 g; 0.6 mmol), potassium carbonate (6.0 g; 43.6 mmol), tetrabutylammonium bromide (0.09 g; 0.3 mmol), toluene (80 mL), ethanol (40 mL) and deionized water (20 mL) were added to a round-bottom flask, and the mixture was heated to 76°C under nitrogen protection and stirred for 5 hours; the reaction solution was cooled to room temperature, toluene was added for extraction, the organic phases were combined, dried with anhydrous magnesium sulfate, filtered, and the solvent was removed under reduced pressure; the crude product was purified by silica gel column chromatography using a dichloromethane / n-heptane system to obtain a white solid product AA1 (8.8 g; yield: 63%).

[0195] Referring to the synthesis method of compound AA1, the intermediate a-1 was replaced by reactant C, and 2-chloro-4-(dibenzofuran-3-yl)-6-phenyl-1,3,5-triazine was replaced by reactant D to synthesize the compounds shown in Table 3 below:

[0196] Table 3

[0197]

[0198]

[0199]

[0200] Synthesis of compound AA73:

[0201]

[0202] Intermediate a-1 (7.8 g; 26.2 mmol), 2-(1,1'-biphenyl-4-yl)-4-(4-chlorophenyl)-6-phenyl-1,3,5-triazine (10.0 g; 23.8 mmol), palladium acetate (0.05 g; 0.2 mmol), 2-dicyclohexylphosphine-2',4',6'-triisopropylbiphenyl (0.2 g; 0.5 mmol), potassium carbonate (6.6 g; 47.6 mmol), tetrabutylammonium bromide (0.07 g; 0.2mmol), toluene (80mL), ethanol (40mL) and deionized water (20mL) were added into a round-bottom flask, and the mixture was heated to 76°C under nitrogen protection and stirred for 5 hours; the reaction solution was cooled to room temperature, toluene was added for extraction, the organic phases were combined, dried over anhydrous magnesium sulfate, filtered, and the solvent was removed under reduced pressure; the crude product was purified by silica gel column chromatography using a dichloromethane / n-heptane system to obtain a white solid product AA73 (8.2g; yield: 62%).

[0203] Referring to the synthesis method of compound AA73, reactant CC in Table 4 below was used to replace intermediate a-1, and reactant E was used to replace 2-(1,1'-biphenyl-4-yl)-4-(4-chlorophenyl)-6-phenyl-1,3,5-triazine to synthesize the compounds shown in Table 4 below:

[0204] Table 4

[0205]

[0206]

[0207]

[0208]

[0209]

[0210] Synthesis of compound EE30

[0211]

[0212] 1-Bromo-2-iodobenzene-3,4,5,6-d4 (50.0 g; 174.3 mmol), thiophenol (28.8 g; 261.4 mmol), CuBr (1.2 g; 8.7 mmol), potassium carbonate (48.2 g; 348.5 mmol), ligand 1,2,3,4-tetrahydro-8-quinoline (0.5 g; 3.5 mmol) and dimethyl sulfoxide (500 mL) were added to a round-bottom flask, and the mixture was heated to 80°C under nitrogen protection and stirred for 24 hours. The reaction solution was cooled to room temperature, toluene was added for extraction, the organic phases were combined, dried with anhydrous magnesium sulfate, filtered, and the solvent was removed under reduced pressure; the crude product was purified by silica gel column chromatography using a dichloromethane / n-heptane system to obtain a solid intermediate bI-1 (38.9 g; yield: 83%).

[0213]

[0214] The intermediate bI-1 (35.0 g; 130.0 mmol), p-chlorophenylboronic acid (21.3 g; 136.5 mmol), tetrakis(triphenylphosphine)palladium (3.0 g; 2.6 mmol), potassium carbonate (35.9 g; 260.0 mmol), tetrabutylammonium bromide (0.4 g; 1.3 mmol), toluene (280 mL), ethanol (140 mL) and deionized water (70 mL) were added to a round-bottom flask, and the mixture was heated to 78°C under nitrogen protection and stirred for 10 hours. The reaction solution was cooled to room temperature, toluene was added for extraction, the organic phases were combined, dried with anhydrous magnesium sulfate, filtered, and the solvent was removed under reduced pressure; the crude product was purified by silica gel column chromatography using a dichloromethane / n-heptane system to obtain the intermediate b-II-1 (30.9 g; yield: 79%).

[0215]

[0216] The intermediate b-II-1 (30.0 g; 99.7 mmol), palladium acetate (1.0 g; 4.5 mmol), 2,6-dimethylbenzoic acid (2.0 g; 13.5 mmol), and toluene (300 mL) were added to a round-bottom flask. Under nitrogen protection, the mixed solution was heated to 110°C and stirred for 18 hours; the reaction solution was cooled to room temperature, toluene was added for extraction, the organic phases were combined, dried with anhydrous magnesium sulfate, filtered, and the solvent was removed under reduced pressure; the crude product was purified by silica gel column chromatography using a dichloromethane / n-heptane system to obtain a solid intermediate b-III-1 (19.7 g; yield: 89%).

[0217]

[0218] b-III-1 (18.0 g; 80.8 mmol), biboric acid pinacol ester (30.8 g; 121.2 mmol), tris[dibenzylideneacetone]dipalladium (0.7 g; 0.8 mmol), 2-dicyclohexylphosphine-2',4',6'-triisopropylbiphenyl (0.8 g; 1.6 mmol), KOAc (15.9 g; 161.6 mmol), 1,4-dioxane (180 mL) were added and refluxed at 100°C for 12 h. When the reaction was completed, dichloromethane and water were used for extraction. The organic layer was dried and concentrated using MgSO4, and the crude product was purified by silica gel column chromatography using dichloromethane and n-heptane as eluents to obtain a white solid compound, which was further purified by recrystallization with dichloromethane and n-heptane to obtain intermediate b-1 (17.3 g; yield: 68%).

[0219]

[0220] Intermediate b-1 (11.8 g; 37.5 mmol), 2-(1,1'biphenyl-4-yl)-4-(4-chlorophenyl)-6-phenyl-1,3,5-triazine (15.0 g; 35.7 mmol), palladium acetate (0.08 g; 0.4 mmol), 2-dicyclohexylphosphine-2',4',6'-triisopropylbiphenyl (0.3 g; 0.7 mmol), potassium carbonate (9.9 g; 71.4 mmol), tetrabutylammonium bromide (0.1 g; 0.4 mmol), toluene (120 mL), ethanol (60 mL) and deionized water (30 mL) were added to a round-bottom flask. Under nitrogen protection, the mixture was heated to 76°C and stirred for 6 hours. The reaction solution was cooled to room temperature, toluene was added for extraction, the organic phases were combined, dried over anhydrous magnesium sulfate, filtered, and the solvent was removed under reduced pressure; the crude product was purified by silica gel column chromatography using a dichloromethane / n-heptane system to obtain a white solid product EE30 (13.5 g; yield: 66%).

[0221] The mass spectrometry data of some compounds are shown in Table 5 below:

[0222] Table 5

[0223] Compound Mass spectrometry data Compound Mass spectrometry data Compound AA1 <![CDATA[m / z=480.19(M+H) + ]]> Compound AA127 <![CDATA[m / z=556.22(M+H) + ]]> Compound AA3 <![CDATA[m / z=556.22(M+H) + ]]> Compound AA150 <![CDATA[m / z=556.22(M+H) + ]]> Compound AA4 <![CDATA[m / z=556.22(M+H) + ]]> Compound AA168 <![CDATA[m / z=556.22(M+H) + ]]> Compound AA7 <![CDATA[m / z=530.21(M+H) + ]]> Compound AA179 <![CDATA[m / z=556.22(M+H) + ]]> Compound AA39 <![CDATA[m / z=569.22(M+H) + ]]> Compound AA186 <![CDATA[m / z=556.22(M+H) + ]]> Compound BB1 <![CDATA[m / z=480.19(M+H) + ]]> Compound BB76 <![CDATA[m / z=480.19(M+H) + ]]> Compound BB3 <![CDATA[m / z=556.22(M+H) + ]]> Compound BB69 <![CDATA[m / z=556.22(M+H) + ]]> Compound BB4 <![CDATA[m / z=556.22(M+H) + ]]> Compound BB126 <![CDATA[m / z=556.22(M+H) + ]]> Compound BB44 <![CDATA[m / z=556.22(M+H) + ]]> Compound BB149 <![CDATA[m / z=556.22(M+H) + ]]> Compound CC1 <![CDATA[m / z=480.19(M+H) + ]]> Compound BB168 <![CDATA[m / z=556.22(M+H) + ]]> Compound CC4 <![CDATA[m / z=556.22(M+H) + ]]> Compound BB179 <![CDATA[m / z=556.22(M+H) + ]]> Compound CC5 <![CDATA[m / z=556.22(M+H) + ]]> Compound BB186 <![CDATA[m / z=556.22(M+H) + ]]> Compound DD3 <![CDATA[m / z=556.22(M+H) + ]]> Compound CC79 <![CDATA[m / z=556.22(M+H) + ]]> Compound DD4 <![CDATA[m / z=556.22(M+H) + ]]> Compound CC80 <![CDATA[m / z=556.22(M+H) + ]]> Compound DD22 <![CDATA[m / z=556.22(M+H) + ]]> Compound CC81 <![CDATA[m / z=632.26(M+H) + ]]> Compound DD119 <![CDATA[m / z=556.23(M+H) + ]]> Compound CC84 <![CDATA[m / z=480.19(M+H) + ]]> Compound DD120 <![CDATA[m / z=516.29(M+H) + ]]> Compound CC128 <![CDATA[m / z=556.22(M+H) + ]]> Compound CC152 <![CDATA[m / z=556.22(M+H) + ]]> Compound DD41 <![CDATA[m / z=556.22(M+H) + ]]> Compound CC153 <![CDATA[m / z=632.26(M+H) + ]]> Compound DD42 <![CDATA[m / z=556.22(M+H) + ]]> Compound CC156 <![CDATA[m / z=566.29(M+H) + ]]> Compound DD44 <![CDATA[m / z=636.26(M+H) + ]]> Compound CC160 <![CDATA[m / z=632.26(M+H) + ]]> Compound DD73 <![CDATA[m / z=556.22(M+H) + ]]> Compound CC175 <![CDATA[m / z=556.22(M+H) + ]]> Compound DD86 <![CDATA[m / z=556.22(M+H) + <!-- 35 -->]]> Compound CC176 <![CDATA[m / z=632.26(M+H) + ]]> Compound DD101 <![CDATA[m / z=556.22(M+H) + ]]> Compound CC182 <![CDATA[m / z=556.22(M+H) + ]]> Compound DD102 <![CDATA[m / z=632.26(M+H) + ]]> Compound DD112 <![CDATA[m / z=556.22(M+H) + ]]> Compound DD118 <![CDATA[m / z=606.24(M+H) + ]]> Compound DD117 <![CDATA[m / z=636.26(M+H) + ]]> Compound EE30 <![CDATA[m / z=572.20(M+H) + ]]> Compound AA73 <![CDATA[m / z=556.22(M+H) + ]]> Compound CC168 <![CDATA[m / z=556.22(M+H) + ]]>

[0224] The NMR data of some compounds are shown in Table 6 below

[0225] Table 6

[0226]

[0227] Synthesis of the second compound

[0228] Synthesis of intermediate a1-b1:

[0229]

[0230] Under nitrogen protection, 2,3-dichloronitrobenzene (50.0 g; 260.4 mmol), d5-phenylboronic acid pinacol ester (54.4 g; 260.4 mmol), tetrakistriphenylphosphine palladium (3.0 g; 2.6 mmol), potassium carbonate (71.9 g; 520.8 mmol), tetrabutylammonium bromide (0.8 g; 2.6 mmol), toluene (400 mL), tetrahydrofuran (200 mL) and deionized water (50 mL) were added to a round-bottom flask, and the mixture was heated to 82°C and stirred for 8 hours. The reaction solution was cooled to room temperature, deionized water was added, and the liquid was separated. The organic phase was washed with water and dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure; the obtained crude product was purified by silica gel column chromatography using a dichloromethane / n-heptane solvent system to obtain a colorless oil intermediate a1-a1 (37.9 g; yield: 61%).

[0231]

[0232] Under nitrogen protection, intermediate a1-a1 (37.0 g; 155.0 mmol), triphenylphosphine (81.3 g; 310.0 mmol), and o-dichlorobenzene (400 mL) were added to a round-bottom flask, and the mixture was heated to 180°C while stirring, and reacted for 24 hours. The reaction solution was cooled to room temperature, deionized water was added, and the liquid was separated. The organic phase was washed with water and dried over anhydrous magnesium sulfate, and the solvent was removed under high temperature and reduced pressure conditions; the obtained crude product was purified by silica gel column chromatography using a dichloromethane / n-heptane system to obtain a white solid intermediate a1-b1 (20.7 g; yield: 65%).

[0233] Synthesis of intermediate a1-d1:

[0234]

[0235] a1-b1 (20.0 g, 97.2 mmol), 4-bromobiphenyl (23.1 g, 99.1 mmol), cuprous iodide (3.7, 19.4 mmol), potassium carbonate (29.3 g, 213.9 mmol), 1,10-phenanthroline (7.0 g, 38.8 mmol), 18-crown ether-6 (2.5 g, 9.7 mmol) were added to a three-necked flask, and dried DMF (200 mL) solvent was added. Under nitrogen protection, the mixed solution was heated to 150°C and stirred for 18 hours. The reaction solution was cooled to room temperature, stirring was stopped, the reaction solution was washed with water, the organic phase was separated, dried with anhydrous magnesium sulfate, and the solvent was removed 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 a white solid product intermediate a1-c1 (26.3 g; yield: 76%).

[0236]

[0237] a1-c1 (26.0 g, 72.6 mmol), biboric acid pinacol ester (22.1 g, 87.1 mmol), tris [dibenzylideneacetone] dipalladium (0.6 g, 0.7 mmol), 2-dicyclohexylphosphine-2', 4', 6'-triisopropylbiphenyl (0.7 g, 1.4 mmol), KOAc (10.5 g, 108.9 mmol), 1,4-dioxane (260 mL) were added and refluxed at 100 ° C for 12 h. When the reaction was completed, dichloromethane and water were used for extraction. The organic layer was dried and concentrated using MgSO4, and the crude product was purified by silica gel column chromatography using dichloromethane and n-heptane as eluents to obtain a white solid compound. It was further purified by recrystallization with dichloromethane and n-heptane to obtain the intermediate a1-d1 (20.2 g; yield: 62%).

[0238] Referring to the synthesis method of intermediates a1-d1, reactant a in Table 7 below is used to replace 4-bromobiphenyl to obtain the intermediate shown in Structure 3, and the intermediate shown in Structure 4 is reacted with diboric acid pinacol ester to obtain the intermediate shown in Structure 4 in Table 7 below.

[0239] Table 7

[0240]

[0241]

[0242] Synthesis of intermediate a1-f1:

[0243]

[0244] Under nitrogen protection, intermediate a1-d1 (20.0 g; 44.5 mmol), o-bromonitrobenzene (8.9 g; 44.5 mmol), tetrakistriphenylphosphine palladium (0.5 g; 0.4 mmol), potassium carbonate (12.3 g; 89.0 mmol), tetrabutylammonium bromide (0.1 g; 0.4 mmol), toluene (160 mL), tetrahydrofuran (40 mL) and deionized water (20 mL) were added to a round-bottom flask, the mixed solution was heated to 82°C, and stirred for 8 hours. The reaction solution was cooled to room temperature, deionized water was added, the liquid was separated, the organic phase was washed with water and dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure; the crude product was purified by silica gel column chromatography using a dichloromethane / n-heptane solvent system to obtain intermediate a1-e1 (14.4 g; yield: 73%).

[0245]

[0246] Under nitrogen protection, intermediate a1-e1 (14.0 g; 31.4 mmol), triphenylphosphine (20.6 g; 78.7 mmol), and o-dichlorobenzene (140 mL) were added to a round-bottom flask, and the mixture was stirred and heated to 180°C for 24 hours. The reaction solution was cooled to room temperature, deionized water was added, and the liquid was separated. The organic phase was washed with water and dried over anhydrous magnesium sulfate, and the solvent was removed under high temperature and reduced pressure; the crude product was purified by silica gel column chromatography using a dichloromethane / n-heptane system to obtain a white solid intermediate a1-f1 (8.3 g; yield: 64%).

[0247] Referring to the synthesis method of intermediate a1-f1, the intermediate a1-e1 is replaced by reactant d in Table 8 below to synthesize the intermediate shown in Structure 6 of Table 6 below:

[0248] Table 8

[0249]

[0250]

[0251] Synthesis of compound a1

[0252]

[0253] Add xylene (80 mL) to a1-f1 (8.0 g, 19.4 mmol), 4-bromobiphenyl (4.7 g, 20.3 mmol), tris[dibenzylideneacetone]dipalladium (0.2 g, 0.2 mmol), 2-dicyclohexylphosphine-2',4',6'-triisopropylbiphenyl (0.2 g, 0.4 mmol), sodium tert-butoxide (2.8 g, 29.0 mmol), and reflux for 6 h at 140°C. When the reaction is finished, dichloromethane and water are used for extraction. The organic phase is dried with MgSO4, filtered, and the organic layer is concentrated under reduced pressure to obtain a crude product, which is purified by silica gel column chromatography using dichloromethane and n-heptane as eluents to obtain a white solid compound, which is further purified by recrystallization with dichloromethane and n-heptane to obtain compound a1 (7.3 g; yield: 67%).

[0254] Referring to the synthesis method of compound a1, the reactant e in Table 9 below replaces the intermediate a1-b, and the reactant f replaces 4-bromobiphenyl to synthesize the compounds shown in Table 9 below:

[0255] Table 9

[0256]

[0257]

[0258]

[0259]

[0260]

[0261]

[0262]

[0263] The synthesis process of the reactant a19-1 used in the above table is as follows:

[0264]

[0265] Under nitrogen protection, dibenzo[b,d]thiophene-1-ylboronic acid (20.0 g; 87.6 mmol), p-bromoiodobenzene (24.8 g; 87.6 mmol), tetrakistriphenylphosphine palladium (1.0 g; 0.8 mmol), potassium carbonate (24.2 g; 175.3 mmol), tetrabutylammonium bromide (0.3 g; 0.8 mmol), toluene (160 mL), ethanol (80 mL) and deionized water (40 mL) were added to a round-bottom flask, and the mixture was heated to 76°C and stirred for 8 hours. The reaction solution was cooled to room temperature, deionized water was added, and the liquid was separated. The organic phase was washed with water and dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure; the crude product was purified by silica gel column chromatography using a dichloromethane / n-heptane solvent system to obtain intermediate a19-1 (20.2 g; yield: 68%).

[0266] Referring to the synthesis method of intermediate a19-1, the reactant b in Table 10 below replaces dibenzo[b,d]thiophene-1-ylboronic acid, and the reactant c replaces p-bromoiodobenzene to synthesize the intermediate shown in Table 10 below:

[0267] Table 10

[0268]

[0269] Among the second compounds, the mass spectrometry data of some compounds are shown in Table 11 below

[0270] Table 11

[0271]

[0272]

[0273] In the second compound, the NMR data of some compounds are shown in Table 12 below

[0274] Table 12

[0275]

[0276] Preparation of organic electroluminescent devices

[0277] Example 1: Preparation of green organic electroluminescent device

[0278] The device was prepared by the following process

[0279] The thickness of ITO / Ag / ITO is The ITO substrate is cut into a size of 40 mm (length) × 40 mm (width) × 0.7 mm (thickness), and surface treatment is performed using ultraviolet ozone and O2:N2 plasma to increase the work function of the anode. The surface of the ITO substrate can be cleaned with an organic solvent to remove impurities and oil stains on the surface of the ITO substrate.

[0280] HT-1 and NDP-9 were co-evaporated on the experimental substrate at an evaporation rate ratio of 97%:3% to form a film with a thickness of Then, HT-1 was vacuum-deposited on the hole injection layer to form a hole injection layer with a thickness of hole transport layer.

[0281] On the hole transport layer, compound HT-2 was vacuum-deposited to form a layer with a thickness of of the hole-assisting layer.

[0282] On the hole auxiliary layer, compound a1 (second compound), compound AA1 (first compound) and compound GD-1 (guest material) were co-evaporated at an evaporation rate ratio of 60%:40%:10% to form a layer with a thickness of of an organic light-emitting layer (EML).

[0283] On the organic light-emitting layer, compound ET-1 and LiQ were co-deposited at a deposition rate ratio of 50%:50% to form A thick electron transport layer (ETL) is formed, and Yb is evaporated on the electron transport layer to form a layer with a thickness of Then, magnesium (Mg) and silver (Ag) were mixed at a 10%:90% evaporation rate and vacuum-deposited on the electron injection layer to form a 10% thick electron injection layer (EIL). cathode.

[0284] 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 the organic electroluminescent device.

[0285] Embodiment 2~embodiment 36:

[0286] An organic electroluminescent device was prepared by the same method as in Example 1, except that the light-emitting layer host material in Table 13 was used instead of the compound a1 (second compound) and the compound AA1 (first compound) in Example 1 at a deposition rate ratio of 60%:40%.

[0287] Comparative Example 1-Comparative Example 2:

[0288] An organic electroluminescent device was prepared by the same method as in Example 1, except that the light-emitting layer main material in Table 13 was used instead of compound a1 (second compound) and compound AA1 (first compound) in Example 1 in a combination with a evaporation rate ratio of 60%:40%.

[0289] Part of the second compound used is shown below. According to the record of patent document US20170025618A1, compound g3 is obtained; according to the record of patent document US20160293853A1, compound g8 is obtained.

[0290]

[0291] The compounds used to prepare the devices of each embodiment and comparative example are as follows:

[0292]

[0293] The green organic electroluminescent devices prepared in Examples 1-36 and Comparative Examples 1-2 were tested for performance. Specifically, at 15 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

[0294] Table 13

[0295]

[0296]

[0297]

[0298] As shown in Table 13 above, when the compounds of the present application are used in the light-emitting layer of an organic electroluminescent device, the device performance can be greatly improved. Specifically, compared with the devices of Comparative Examples 1 and 2, the current efficiency of the devices of Examples 1-36 is improved by at least 13.6%, and the life span is improved by at least 20.1%.

[0299] Example 37: Preparation of green organic electroluminescent device

[0300] The device was prepared by the following process

[0301] The thickness of ITO / Ag / ITO is The ITO substrate is cut into a size of 40 mm (length) × 40 mm (width) × 0.7 mm (thickness), and surface treatment is performed using ultraviolet ozone and O2:N2 plasma to increase the work function of the anode. The surface of the ITO substrate can be cleaned with an organic solvent to remove impurities and oil stains on the surface of the ITO substrate.

[0302] HT-1 and NDP-9 were co-evaporated on the experimental substrate at an evaporation rate ratio of 97%:3% to form a film with a thickness of A hole injection layer (HIL) is formed by vacuum evaporating compound HT-1 on the hole injection layer to form a layer with a thickness of hole transport layer.

[0303] On the hole transport layer, compound HT-3 was vacuum evaporated to form a layer with a thickness of of the hole-assisting layer.

[0304] On the hole auxiliary layer, compound A2 (second compound), compound AA39 (first compound) and compound GD-1 (guest material) were co-evaporated at an evaporation rate ratio of 60%:40%:10% to form a layer with a thickness of of an organic light-emitting layer (EML).

[0305] On the organic light-emitting layer, compound ET-1 and LiQ were co-evaporated at a thickness ratio of 50:50% to form A thick electron transport layer (ETL) is formed, and Yb is evaporated on the electron transport layer to form a layer with a thickness of Then, magnesium (Mg) and silver (Ag) were mixed at a 10%:90% evaporation rate and vacuum-deposited on the electron injection layer to form a 10% thick electron injection layer (EIL). cathode.

[0306] 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 the organic electroluminescent device.

[0307] Embodiment 38~embodiment 57:

[0308] An organic electroluminescent device was prepared by the same method as in Example 37, except that the light-emitting layer main material in Table 14 was used instead of the compound A2 (second compound) and compound AA39 (first compound) in Example 37 in a combination with a deposition rate ratio of 60%:40% (60:40).

[0309] Comparative Examples 3 to 6:

[0310] An organic electroluminescent device was prepared by the same method as in Example 37, except that the light-emitting layer main material in Table 14 was used instead of compound A5 (second compound) and compound AA39 (first compound) in Example 37 in a combination with a evaporation rate ratio of 60%:40%.

[0311] Some of the second compounds used are shown below. According to the records of patent document CN115403569A, compound A2 is obtained; according to the records of patent document CN104488105B, compound A5 is obtained; according to the records of patent document JP3139321B2, compound A26 is obtained; according to the records of patent document KR1020170024418A, compound A56 is obtained; according to patent document KR2016027940A, compound A29 is obtained; according to the records of patent document WO2022211594A1, compound B46 is obtained; according to the records of patent document CN115368293A, compounds B104 and B105 are obtained.

[0312]

[0313] The compounds used to prepare the devices of each embodiment and comparative example are as follows:

[0314]

[0315]

[0316] The green organic electroluminescent devices prepared in Examples 37 to 57 and Comparative Examples 3 to 6 were tested for their performance. Specifically, at 15 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

[0317] Table 14

[0318]

[0319]

[0320] As shown in Table 14, when the compounds of the present application are used in the light-emitting layer of an organic electroluminescent device, the device performance can be greatly improved. Specifically, compared with the devices of Comparative Examples 3-6, the current efficiency of the devices of Examples 37-57 is improved by at least 17.7%, and the lifespan is improved by at least 12.8%.

[0321] Compared with Comparative Examples 3 and 4, the device performance is significantly improved when the organic compound used in the present application is used as the electronic host material of the green light-emitting layer. The reason for this may be that compared with compounds III and IV, the specific sites of dibenzofuran in the compounds of the present application are partially deuterated, which improves its photoelectric stability.

[0322] Compared with Comparative Example 5, when the organic compound used in the present application is used as the electronic host material of the green light-emitting layer, the life and efficiency of the device are significantly improved. The reason may be that dibenzothiophene is used as the connecting group of triazine and dibenzofuran in Compound V, and the compound of the present application uses a single bond or arylene group to connect the triazine group, so that the molecule has better electron injection and transport properties, and the injection and recombination efficiency of carriers are improved.

[0323] Compared with Comparative Example 6, when the organic compound used in the present application is used as the electronic main material of the green light-emitting layer, the life and efficiency of the device are significantly improved. The reason may be that two dibenzofuran groups are connected to the triazine in compound VI, which reduces the energy level of compound T1, thereby reducing the luminous efficiency when the compound is used as the main material of the organic electroluminescent layer.

[0324] Part of the embodiments of the present application are described in detail above in conjunction with the accompanying drawings; however, the present application is not limited to the specific details in the above embodiments. Within the technical concept of the present application, a variety of simple modifications can be made to the technical solution of the present application, and these simple modifications all fall within the protection scope of the present application.

Claims

1. Organic compounds, It is characterized in that The organic compound has a structure as shown in Formula 1: Wherein X is selected from C(R 1 R 2 ), O or S; R 1 and R 2 are the same or different and are independently selected from an alkyl group having 1 to 5 carbon atoms and a deuterated alkyl group having 1 to 5 carbon atoms; L, L 1 and L 2 are the same or different and are independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 20 carbon atoms; Ar 1 and Ar 2 are the same or different and are independently selected from substituted or unsubstituted aryl groups and substituted or unsubstituted carbazolyl groups having 6 to 30 carbon atoms; L, L 1 , L 2 ,Ar 1 and Ar 2 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, halogenated alkyl 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, trialkylsilyl groups having 3 to 12 carbon atoms, halogenated aryl groups having 6 to 20 carbon atoms or cycloalkyl groups having 3 to 10 carbon atoms.

2. The organic compound according to claim 1, It is characterized in that L, L 1 and L 2 are the same or different and are independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 12 carbon atoms; Optionally, the L, L 1 and L 2 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 5 carbon atoms or a phenyl group.

3. The organic compound according to claim 1, It is characterized in that L, L 1 and L 2 are the same or different and are 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; Optionally, the L, L 1 and L 2 The substituents in are the same or different and are independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl or phenyl.

4. The organic compound according to claim 1, It is characterized in that Ar 1 and Ar 2 are the same or different and are independently selected from substituted or unsubstituted aryl groups having 6 to 20 carbon atoms, and substituted or unsubstituted carbazolyl groups; Optionally, the Ar 1 and Ar 2 The substituents in are the same or different and are independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, phenyl or pentadeuterated phenyl.

5. The organic compound according to claim 1, It is characterized in that Ar 1 and Ar 2 are the same or different and are independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted carbazolyl; Optionally, the Ar 1 and Ar 2 The substituents in are the same or different and are independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, phenyl or pentadeuterated phenyl.

6. The organic compound according to claim 1, It is characterized in that The same or different, are independently selected from the following groups:

7. The organic compound according to claim 1, It is characterized in that The organic compound is selected from the group consisting of the following compounds:

8. Composition, It is characterized in that The composition comprises a first compound and a second compound; The first compound is selected from the organic compound according to any one of claims 1 to 7, and the second compound has a structure shown in Formula 2 or Formula 3: Among them, each R 3 , each R 4 , each R 5 , each R 6 , each R 7 , each R 8 and each R 9 are the same or different and are independently selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 5 carbon atoms, an aryl group having 6 to 20 carbon atoms, a deuterated aryl group having 6 to 20 carbon atoms, a halogenated aryl group having 6 to 20 carbon atoms or a heteroaryl group having 3 to 20 carbon atoms; n 3 For R 3 The number of is selected from 0, 1, 2, 3 or 4. 3 When it is greater than 2, any two R 3 Same or different; n 4 For R 4 The number of is selected from 0, 1, 2 or 3. 4 When it is greater than 2, any two R 4 Same or different; n 5 For R 5 The number of is selected from 0, 1, 2 or 3. 5 When it is greater than 2, any two R 5 Same or different; n 6 For R 6 The number of is selected from 0, 1, 2, 3 or 4. 6 When it is greater than 2, any two R 6 Same or different; n 7 For R 7 The number of is selected from 0, 1, 2, 3 or 4. 7 When it is greater than 2, any two R 7 Same or different; n 8 For R 8 The number of is selected from 0, 1 or 2, when n 8 When it is greater than 2, any two R 8 Same or different; n 9 For R 9 The number of is selected from 0, 1, 2, 3 or 4. 9 When it is greater than 2, any two R 9 Same or different; L 3 , L 4 , L 5 and L 6 are the same or different and are 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; Ar 3 ,Ar 4 ,Ar 5 and Ar 6 are the same or different and are 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; L 3 , L 4 , L 5 , L 6 ,Ar 3 ,Ar 4 ,Ar 5 and Ar 6 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, halogenated alkyl 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, halogenated aryl groups having 6 to 20 carbon atoms or cycloalkyl groups having 3 to 10 carbon atoms.

9. The composition according to claim 8, It is characterized in that In the second compound represented by Formula 2, L 3 and L 4 are the same or different and are independently selected from a single bond, a substituted or unsubstituted phenylene, a substituted or unsubstituted naphthylene, a substituted or unsubstituted biphenylene, a substituted or unsubstituted terphenylene, a substituted or unsubstituted carbazolylene, a substituted or unsubstituted dibenzofuranylene, a substituted or unsubstituted dibenzothiophenylene, Optionally, the L 3 and L 4 The substituents in are the same or different and are independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl or phenyl; Preferably, Ar 3 and Ar 4 are the same or different and are independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted quaterphenyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, Further preferably, the Ar 3 and Ar 4 The substituents in are the same or different and are independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, phenyl, monodeuterated phenyl or pentadeuterated phenyl.

10. The composition according to claim 8, It is characterized in that In the second compound represented by Formula 3, L 5 and L 6 are the same or different and are 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 terphenylene group, Optionally, the L 5 and L 6 The substituents in are the same or different and are independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl or phenyl; Preferably, Ar 5 and Ar 6 are the same or different and are independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted quaterphenyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, Further preferably, the Ar 5 and Ar 6 The substituents in are the same or different and are independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, phenyl, monodeuterated phenyl or pentadeuterated phenyl.

11. The composition according to claim 8, It is characterized in that In the second compound represented by Formula 2 The same or different, are independently selected from the following groups:

12. The composition according to claim 8, It is characterized in that In the second compound shown in Formula 3 The same or different, are independently selected from the following groups:

13. The composition according to claim 8, It is characterized in that In the second compound represented by Formula 2, each R 3 , each R 4 , each R 5 , each R 6 are the same or different, and are independently selected from deuterium, phenyl or pentadeuterated phenyl; In the second compound represented by Formula 3, each R 7 , each R 8 and each R 9 are the same or different, and are independently selected from deuterium, phenyl or pentadeuterated phenyl.

14. The composition according to claim 8, It is characterized in that The second compound represented by Formula 2 is selected from the group consisting of the following compounds: The second compound represented by Formula 3 is selected from the group consisting of the following compounds:

15. Organic electroluminescent devices, It is characterized in that The invention comprises 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 according to any one of claims 1 to 7 or the composition according to any one of claims 8 to 14; Optionally, the functional layer comprises an organic light-emitting layer, and the organic light-emitting layer comprises the organic compound according to any one of claims 1 to 7 or the composition according to any one of claims 8 to 14.

16. Electronic devices, It is characterized in that The organic electroluminescent device according to claim 15 is included.

Images