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, a composition containing the organic compound, an organic electroluminescent device, and an electronic device. Background Art

[0002] With the development of electronic technology and the progress of material science, the application scope of electronic components for realizing electroluminescence has become increasingly wide. Such electronic components generally include a cathode and an anode disposed opposite to each other, and a functional layer disposed between the cathode and the anode. The functional layer is composed of multiple organic or inorganic film layers, and generally includes an organic light-emitting layer, a hole transport layer 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, a light-emitting adjustment layer, an organic light-emitting layer, an electron transport layer, and a cathode stacked in sequence. When a voltage is applied between the two electrodes, an electric field is generated between the two electrodes. Under the action of the electric field, electrons on the cathode side move towards the organic light-emitting layer, and holes on the anode side also move towards the organic light-emitting layer. The electrons and holes combine in the organic light-emitting layer to form excitons. The excitons are in an excited state and release energy outward, thereby causing the organic light-emitting layer to emit light externally.

[0003] The prior art has disclosed host materials for preparing organic light-emitting layers in organic electroluminescent devices. However, it is still necessary to continue to research and develop new materials to further improve the performance of organic electroluminescent devices. Summary of the Invention

[0004] To solve the above problems, the purpose of the present application is to provide an organic compound, a composition containing the organic compound, an organic electroluminescent device, and an electronic device. 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 lifespan of the device.

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

[0006]

[0007] One of A and B is hydrogen, and the other is selected from the group shown in Formula 1-1;

[0008] Ring C is selected from a naphthalene ring or a phenanthrene ring;

[0009] D represents deuterium;

[0010] n is the number of Ds, and is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, or 12;

[0011] Each R1 and each R2 are the same or different and are each independently selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms, a deuterated aryl group having 6 to 20 carbon atoms, or a halogenated aryl group having 6 to 20 carbon atoms;

[0012] n1 is the number of R1s and is selected from 0, 1, 2, 3, or 4. When n1 is greater than 1, any two R1s are the same or different;

[0013] n2 is the number of R2s and is selected from 0, 1, 2, 3, or 4. When n2 is greater than 1, any two R2s are the same or different;

[0014] L1 and L2 are the same or different and are each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms;

[0015] Ar1 and Ar2 are the same or different and are each 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;

[0016] The substituents in L1, L2, Ar1, and Ar2 are the same or different and are each independently selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, a heteroaryl group having 3 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms, a deuterated aryl group having 6 to 20 carbon atoms, or a halogenated aryl group having 6 to 20 carbon atoms.

[0017] In a second aspect of the present application, there is provided a composition comprising a first compound disclosed in the first aspect of the present application and a second compound having a structure represented by Formula 2 or Formula 3.

[0018] In a third aspect of the present application, there is provided an organic electroluminescent device including an anode and a cathode disposed opposite to each other, and a functional layer disposed between the anode and the cathode; the functional layer contains the organic compound disclosed in the first aspect of the present application or the composition disclosed in the second aspect of the present application.

[0019] In a fourth aspect of the present application, there is provided an electronic device including the organic electroluminescent device disclosed in the third aspect of the present application.

[0020] The core structure of the organic compound of the present application is composed of a triazine, a carbazole, a phenylene group, and a polycyclic group containing a phenanthrene group. Among them, the triazine and the carbazole are ortho-linked to the phenylene group, and the polycyclic group containing a phenanthrene group is linked to the para-position of the triazine or the carbazole. This specific connection method enables the compound to have a good spatial D-A conjugation effect and effectively reduces the ΔE of the material ST(The energy level difference between the first excited singlet state and the first excited triplet state), which improves the energy transfer efficiency of the compound. At the same time, the compound of the present application has a high T1 energy level and directionality, which is helpful for carrier and energy transfer. When the nitrogen-containing compound of the present application is used as the host material of the organic light-emitting layer in an organic electroluminescent device, the light-emitting efficiency and lifespan of the device can be improved.

[0021] Other features and advantages of the present application will be described in detail in the following detailed description section. BRIEF DESCRIPTION OF THE DRAWINGS

[0022] The drawings are used to provide a further understanding of the present application and constitute a part of the specification. Together with the following detailed description, they are used to explain the present application, but do not constitute a limitation to the present application.

[0023] Figure 1 It is a schematic structural diagram of an organic electroluminescent device of the present application.

[0024] Figure 2 It is a schematic structural diagram of an electronic device of the present application.

[0025] REFERENCE NUMERALS

[0026] 100, Anode; 200, Cathode; 300, Functional layer; 310, Hole injection layer

[0027] 320, Hole transport layer; 330, Luminescence adjustment layer; 340, Organic light-emitting layer; 350, Electron transport layer

[0028] 360, Electron injection layer; 400, Electronic device DETAILED DESCRIPTION

[0029] Aiming at the above problems existing in the prior art, the purpose of the present application is to provide an organic compound, an organic electroluminescent device and an electronic device including the organic compound. 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 lifespan of the device.

[0030] In the first aspect of the present application, an organic compound is provided, and the organic compound has a structure shown in Formula 1:

[0031]

[0032] One of A and B is hydrogen, and the other is selected from the group shown in Formula 1-1;

[0033] Ring C is selected from a naphthalene ring or a phenanthrene ring; [[ID=T46]]

[0034] D represents deuterium;

[0035] n is the number of Ds, selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11 or 12;

[0036] Each R1 and each R2 are the same or different, and are each independently selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms, a deuterated aryl group having 6 to 20 carbon atoms, or a halogenated aryl group having 6 to 20 carbon atoms;

[0037] n1 is the number of R1s, selected from 0, 1, 2, 3 or 4. When n1 is greater than 1, any two R1s are the same or different;

[0038] n2 is the number of R2s, selected from 0, 1, 2, 3 or 4. When n2 is greater than 1, any two R2s are the same or different;

[0039] L1 and L2 are the same or different, and are each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms;

[0040] Ar1 and Ar2 are the same or different, and are each 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;

[0041] The substituents in L1, L2, Ar1 and Ar2 are the same or different, and are each independently selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, a heteroaryl group having 3 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms, a deuterated aryl group having 6 to 20 carbon atoms, or a halogenated aryl group having 6 to 20 carbon atoms.

[0042] In the present application, the description modes "each... is independently", "... are each independently", and "... are each independently" can be interchanged, and should all be understood in a broad sense. It can either mean that among different groups, the specific options expressed between the same symbols do not affect each other, or it can also mean that within the same group, the specific options expressed between 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. Its meaning is: Formula Q-1 means that there are q substituents R" on the benzene ring, and each R" can be the same or different, and the options of each R" do not affect each other; Formula Q-2 means that there are q substituents R" on each benzene ring of the biphenyl, the number q of the 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.

[0043] In the present application, a term such as "substituted or unsubstituted" means that the functional group described after this term may or may not have a substituent (hereinafter, for the sake of convenience of description, the substituent is collectively referred to as Rc). For example, "substituted or unsubstituted aryl" means an aryl having a substituent Rc or an unsubstituted aryl. Among them, the above-mentioned substituent, namely Rc, can be, for example, deuterium, cyano group, halogen group, alkyl group, aryl group, heteroaryl group, deuterated aryl group, halogenated aryl group, cycloalkyl group, etc. The number of substitutions can be one or more.

[0044] In the present application, "a plurality of" means more than two, such as two, three, four, five, six, etc.

[0045] In the present application, the number of carbon atoms of a substituted or unsubstituted functional group refers to all the carbon atoms. For example, if L1 is a substituted arylene group with 12 carbon atoms, then the total number of carbon atoms of the arylene group and the substituents thereon is 12.

[0046] In the present application, an aryl group refers to an optional functional group or substituent derived from an aromatic carbocyclic ring. An aryl group can be a monocyclic aryl group (such as phenyl) or a polycyclic aryl group. In other words, an aryl group can be a monocyclic aryl group, a fused-ring aryl group, two or more monocyclic aryl groups connected by a carbon-carbon bond, a monocyclic aryl group and a fused-ring aryl group connected by a carbon-carbon bond, two or more fused-ring aryl groups connected by a carbon-carbon bond. That is, unless otherwise specified, two or more aromatic groups connected by a carbon-carbon bond can also be regarded as the aryl group of the present application. Among them, the fused-ring aryl group can include, for example, bicyclic fused aryl groups (such as naphthyl), tricyclic fused aryl groups (such as phenanthryl, fluorenyl, anthryl), etc. The aryl group does not contain heteroatoms such as B, N, O, S, P, Se and Si. Examples of aryl groups can include, but are not limited to, phenyl, naphthyl, fluorenyl, anthryl, phenanthryl, biphenyl, terphenyl, triphenylene, perylene, benzo[9,10]phenanthryl, pyrenyl, benzo[a]pyrenyl, and so on. In the present application, the arylene group involved refers to a divalent group formed by an aryl group further losing one hydrogen atom.

[0047] 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 being 18.

[0048] In the present application, the number of carbon atoms of the substituted or unsubstituted aryl group can 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 some other embodiments, the substituted or unsubstituted aryl group is a substituted or unsubstituted aryl group having 6 to 25 carbon atoms. In some other embodiments, the substituted or unsubstituted aryl group is a substituted or unsubstituted aryl group having 6 to 20 carbon atoms. In some other embodiments, the substituted or unsubstituted aryl group is a substituted or unsubstituted aryl group having 6 to 12 carbon atoms.

[0049] In the present application, examples of the aryl group as the substituent of Ar1, Ar2, Ar3, Ar4, Ar5, Ar6, L1, L2, L3, L4, L5, L6 include, but are not limited to, phenyl, naphthyl and the like.

[0050] In the present application, a 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 heteroatoms 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 bonds, and any aromatic ring system is an aromatic monocyclic ring or an aromatic fused ring. Exemplarily, the heteroaryl group can include, but is not limited to, thienyl, furyl, pyrrolyl, imidazolyl, thiazolyl, oxazolyl, oxadiazolyl, triazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, acridinyl, pyridazinyl, pyrazinyl, quinolinyl, quinazolinyl, quinoxalinyl, phenoxazinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, isoquinolinyl, indolyl, carbazolyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothienyl, dibenzothienyl, thienothienyl, benzofuryl, phenanthrolinyl, isoxazolyl, thiadiazolyl, phenothiazinyl, silafluorene, dibenzofuryl, and N-phenylcarbazolyl, N-pyridylcarbazolyl, N-methylcarbazolyl, etc.

[0051] 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. In some other embodiments, the substituted or unsubstituted heteroaryl group is a substituted or unsubstituted heteroaryl group having 12 to 18 carbon atoms.

[0052] In the present application, the substituted heteroaryl may be one or more hydrogen atoms in the heteroaryl being substituted by groups such as deuterium atoms, halogen groups, -CN, aryl, heteroaryl, alkyl, cycloalkyl, deuterated aryl, halogenated aryl, etc. It should be understood that the number of carbon atoms in the substituted heteroaryl refers to the total number of carbon atoms of the heteroaryl and the substituents on the heteroaryl.

[0053] In the present application, the alkyl having 1 to 10 carbon atoms may include a straight-chain alkyl having 1 to 10 carbon atoms and a branched-chain alkyl having 3 to 10 carbon atoms. The number of carbon atoms of the alkyl may be, for example, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10. Specific examples of the alkyl include, but are not limited to, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl, neopentyl, n-hexyl, etc.

[0054] In the present application, the halogen group may be, for example, fluorine, chlorine, bromine, iodine.

[0055] In the present application, the deuterated aryl refers to an aryl containing at least one deuterium substituent. Specific examples of the deuterated aryl include, but are not limited to, pentadeuterophenyl, pentadeuterobiphenyl.

[0056] In the present application, the number of carbon atoms of the cycloalkyl having 3 to 10 carbon atoms may be, for example, 3, 4, 5, 6, 7, 8 or 10. Specific examples of the cycloalkyl include, but are not limited to, cyclopentyl, cyclohexyl, adamantyl.

[0057] In the present application, the non-positioned connecting bond refers to a single bond extending from the ring system It means that one end of the connecting bond can be connected to any position in the ring system penetrated by the bond, and the other end is connected to the rest of the compound molecule. For example, as shown in the following formula (f), the naphthyl group represented by formula (f) is connected to other positions of the molecule through two non-positioned connecting bonds penetrating the bicyclic ring, and the meaning it represents includes any possible connection mode shown in formulas (f-1) to (f-10).

[0058]

[0059]

[0060] For another example, as shown in the following formula (X'), the dibenzofuranyl group represented by formula (X') is connected to other positions of the molecule through a non-positioned connecting bond extending from the middle of one side benzene ring, and the meaning it represents includes any possible connection mode shown in formulas (X'-1) to (X'-4).

[0061]

[0062] In some embodiments of the present application, the organic compound represented by Formula 1 is selected from the structures represented by Formula 1-1-1 or Formula 1-1-2:

[0063]

[0064] In Formula 1-1-1 and Formula 1-1-2, ring C is selected from a naphthalene ring or a phenanthrene ring;

[0065] D represents deuterium;

[0066] n is the number of Ds and is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, or 12;

[0067] Each R1 and each R2 are the same or different and are each independently selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms, a deuterated aryl group having 6 to 20 carbon atoms, or a halogenated aryl group having 6 to 20 carbon atoms;

[0068] n1 is the number of R1s and is selected from 0, 1, 2, 3, or 4. When n1 is greater than 1, any two R1s are the same or different;

[0069] n2 is the number of R2s and is selected from 0, 1, 2, 3, or 4. When n2 is greater than 1, any two R2s are the same or different;

[0070] L1 and L2 are the same or different and are each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms;

[0071] Ar1 and Ar2 are the same or different and are each 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;

[0072] The substituents in L1, L2, Ar1, and Ar2 are the same or different and are each independently selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, a heteroaryl group having 3 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms, a deuterated aryl group having 6 to 20 carbon atoms, or a halogenated aryl group having 6 to 20 carbon atoms.

[0073] In some embodiments of the present application, the organic compound represented by Formula 1 is selected from the structures represented by Formula 1-A, Formula 1-B, Formula 1-C, Formula 1-D, Formula 1-E, Formula 1-F, Formula 1-G, Formula 1-H, Formula 1-I, or Formula 1-L:

[0074]

[0075] In some embodiments of the present application, in the organic compound represented by Formula 1, one of A and B is hydrogen, and the other is selected from the group consisting of the following groups:

[0076]

[0077] Specifically, in the organic compound represented by Formula 1, one of A and B is hydrogen, and the other is selected from the group consisting of the following groups:

[0078]

[0079] In some embodiments of the present application, in the organic compound represented by Formula 1, each R1 and each R2 are the same or different and are independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, phenyl, or pentadeuterophenyl.

[0080] In some embodiments of the present application, in the organic compound represented by Formula 1, 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, and a substituted or unsubstituted heteroarylene group having 12 to 18 carbon atoms.

[0081] Optionally, the substituents in L1 and L2 are the same or different and are independently selected from deuterium, fluorine, cyano, an alkyl group having 1 to 5 carbon atoms, phenyl, or pentadeuterophenyl.

[0082] In some other embodiments of the present application, in the organic compound represented by Formula 1, 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, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted carbazolylene group, a substituted or unsubstituted dibenzofuranylene group, and a substituted or unsubstituted dibenzothiophenylene group.

[0083] Optionally, the substituents in L1 and L2 are the same or different and are independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, phenyl, or pentadeuterophenyl.

[0084] In some embodiments of the present application, in the organic compound represented by Formula 1, L1 and L2 are the same or different and are independently selected from a single bond or the group consisting of the following groups:

[0085]

[0086] Optionally, in the organic compound represented by Formula 1, L1 and L2 are the same or different and are independently selected from a single bond or the group consisting of the following groups:

[0087]

[0088] In some embodiments of the present application, in the organic compound represented by Formula 1, Ar1 and Ar2 are the same or different, and are each independently selected from substituted or unsubstituted aryl groups having 6 to 18 carbon atoms and substituted or unsubstituted heteroaryl groups having 12 to 18 carbon atoms.

[0089] Optionally, the substituents in Ar1 and Ar2 are the same or different, and are each independently selected from deuterium, fluorine, cyano, alkyl groups having 1 to 5 carbon atoms, phenyl groups or pentadeuterophenyl groups.

[0090] In some embodiments of the present application, in the organic compound represented by Formula 1, Ar1 and Ar2 are the same or different, and are each independently selected from substituted or unsubstituted phenyl groups, substituted or unsubstituted naphthyl groups, substituted or unsubstituted biphenyl groups, substituted or unsubstituted terphenyl groups, substituted or unsubstituted fluorenyl groups, substituted or unsubstituted phenanthryl groups, substituted or unsubstituted carbazolyl groups, substituted or unsubstituted dibenzofuranyl groups, and substituted or unsubstituted dibenzothiophenyl groups.

[0091] Optionally, the substituents in Ar1 and Ar2 are the same or different, and are each independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, phenyl groups or pentadeuterophenyl groups.

[0092] In some embodiments of the present application, in the organic compound represented by Formula 1, Ar1 and Ar2 are the same or different, and are each independently selected from the group consisting of the following groups:

[0093]

[0094] Specifically, in the organic compound represented by Formula 1, Ar1 and Ar2 are the same or different, and are each independently selected from the group consisting of the following groups:

[0095]

[0096] In some embodiments of the present application, in the organic compound represented by Formula 1, being the same or different, are each independently selected from the group consisting of the following groups:

[0097]

[0098] Specifically, in the organic compound represented by Formula 1, being the same or different, are each independently selected from the group consisting of the following groups:

[0099]

[0100] In some embodiments of the present application, in the organic compound represented by Formula 1, selected from the group consisting of the following groups:

[0101]

[0102]

[0103] In some embodiments of the present application, for the organic compound shown in Formula 1, each R1 and each R2 are the same or different and are independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, phenyl or pentadeuterophenyl.

[0104] In some embodiments of the present application, the organic compound shown in Formula 1 is selected from the compounds shown in Claim 7.

[0105] The second aspect of the present application further provides a composition, which comprises a first compound and a second compound;

[0106] The first compound has the structure shown in Formula 1, and the second compound is selected from the structures shown in Formula 2 or Formula 3:

[0107]

[0108] 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, cyano, 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;

[0109] n3 is the number of R3 and is selected from 0, 1, 2, 3 or 4. When n3 is greater than 1, any two R3 are the same or different;

[0110] n4 is the number of R4 and is selected from 0, 1, 2 or 3. When n4 is greater than 1, any two R4 are the same or different;

[0111] n5 is the number of R5 and is selected from 0, 1, 2 or 3. When n5 is greater than 1, any two R5 are the same or different;

[0112] n6 is the number of R6 and is selected from 0, 1, 2, 3 or 4. When n6 is greater than 1, any two R6 are the same or different;

[0113] n7 is the number of R7 and is selected from 0, 1, 2, 3 or 4. When n7 is greater than 1, any two R7 are the same or different;

[0114] n8 is the number of R8 and is selected from 0, 1 or 2. When n8 is greater than 1, any two R8 are the same or different;

[0115] n9 is the number of R9 and is selected from 0, 1, 2, 3 or 4. When n9 is greater than 1, any two R9 are the same or different;

[0116] L3, L4, L5, and L6 are the same or different and are each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms;

[0117] Ar3, Ar4, Ar5, and Ar6 are the same or different and are each 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;

[0118] The substituents in L3, L4, L5, L6, Ar3, Ar4, Ar5, and Ar6 are the same or different and are each 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, an aryl group having 6 to 20 carbon atoms, a deuterated aryl group having 6 to 20 carbon atoms, a haloaryl group having 6 to 20 carbon atoms, or a cycloalkyl group having 3 to 10 carbon atoms.

[0119] In some embodiments of the present application, the second compound is selected from the structures shown in Formula 2-1 or Formula 3-1:

[0120]

[0121] In some embodiments of the present application, in the second compound, L3, L4, L5, and L6 are the same or different and are each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 18 carbon atoms, or a substituted or unsubstituted heteroarylene group having 12 to 18 carbon atoms.

[0122] Optionally, in the second compound, the substituents in L3, L4, L5, and L6 are the same or different and are each independently selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 5 carbon atoms, or a phenyl group.

[0123] Further optionally, in the second compound shown in Formula 2, L3 and L4 are the same or different and are each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 12 carbon atoms, or a substituted or unsubstituted heteroarylene group having 12 to 18 carbon atoms.

[0124] Further optionally, in the second compound shown in Formula 3, L5 and L6 are the same or different and are each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 18 carbon atoms, or a substituted or unsubstituted heteroarylene group having 12 to 18 carbon atoms.

[0125] 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 each independently selected from a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted carbazolylene group, a substituted or unsubstituted dibenzofuranylene group, a substituted or unsubstituted dibenzothiophenylene group.

[0126] Optionally, in the second compound represented by Formula 2, the substituents in L3 and L4 are the same or different and are each independently selected from deuterium, fluorine, a cyano group, a methyl group, an ethyl group, a n-propyl group, an isopropyl group, a tert-butyl group or a phenyl group.

[0127] In some other embodiments of the present application, in the second compound represented by Formula 3, L5 and L6 are the same or different and are each independently selected from a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted carbazolylene group, a substituted or unsubstituted dibenzofuranylene group, a substituted or unsubstituted dibenzothiophenylene group.

[0128] Optionally, in the second compound represented by Formula 3, the substituents in L5 and L6 are the same or different and are each independently selected from deuterium, fluorine, a cyano group, a methyl group, an ethyl group, a n-propyl group, an isopropyl group, a tert-butyl group or a phenyl group.

[0129] 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 each independently selected from a single bond or the group consisting of the following groups:

[0130]

[0131] Specifically, in the second compound represented by Formula 2, L3 and L4 are the same or different and are each independently selected from a single bond or the group consisting of the following groups:

[0132]

[0133]

[0134] 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 each independently selected from a single bond or the group consisting of the following groups:

[0135]

[0136] Specifically, in the second compound represented by Formula 3, L5 and L6 are the same or different and are each independently selected from a single bond or the group consisting of the following groups:

[0137]

[0138] In some embodiments of the present application, in the second compound, Ar3, Ar4, Ar5 and Ar6 are the same or different and are each 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.

[0139] Optionally, the substituents in Ar3, Ar4, Ar5 and Ar6 are the same or different and are each 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.

[0140] In some other embodiments of the present application, in the second compound, Ar3, Ar4, Ar5 and Ar6 are the same or different and are each independently selected from substituted or unsubstituted phenyl groups, substituted or unsubstituted naphthyl groups, substituted or unsubstituted phenanthryl groups, substituted or unsubstituted fluorenyl groups, substituted or unsubstituted terphenyl groups, substituted or unsubstituted quaterphenyl groups, substituted or unsubstituted carbazolyl groups, substituted or unsubstituted dibenzofuranyl groups, substituted or unsubstituted dibenzothiophenyl groups.

[0141] Optionally, in the second compound, the substituents in Ar3, Ar4, Ar5 and Ar6 are the same or different and are each independently selected from deuterium, fluorine, a cyano group, a methyl group, an ethyl group, a n-propyl group, an isopropyl group, a tert-butyl group, a phenyl group, a monodeuterated phenyl group or a pentadeuterated phenyl group.

[0142] Further optionally, in the second compound represented by Formula 2, Ar3 and Ar4 are the same or different and are each independently selected from substituted or unsubstituted phenyl groups, substituted or unsubstituted naphthyl groups, substituted or unsubstituted fluorenyl groups, substituted or unsubstituted terphenyl groups, substituted or unsubstituted carbazolyl groups, substituted or unsubstituted dibenzofuranyl groups, substituted or unsubstituted dibenzothiophenyl groups.

[0143] Further optionally, in the second compound represented by Formula 3, Ar5 and Ar6 are the same or different and are each independently selected from substituted or unsubstituted phenyl groups, substituted or unsubstituted naphthyl groups, substituted or unsubstituted fluorenyl groups, substituted or unsubstituted terphenyl groups, substituted or unsubstituted quaterphenyl groups, substituted or unsubstituted carbazolyl groups, substituted or unsubstituted dibenzofuranyl groups, substituted or unsubstituted dibenzothiophenyl groups.

[0144] 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 each independently selected from the group consisting of the following groups:

[0145]

[0146] Specifically, in the second compound represented by Formula 2, Ar3 and Ar4 are the same or different and are each independently selected from a single bond or the group consisting of the following groups:

[0147]

[0148]

[0149] 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 each independently selected from the group consisting of the following groups:

[0150]

[0151] Specifically, in the second compound represented by Formula 3, Ar5 and Ar6 are the same or different and are each independently selected from a single bond or the group consisting of the following groups:

[0152]

[0153]

[0154] In some embodiments of the present application, in the second compound represented by Formula 2, are the same or different and are each independently selected from the group consisting of the following groups:

[0155]

[0156]

[0157] Specifically, in the second compound represented by Formula 2, are the same or different and are each independently selected from the group consisting of the following groups:

[0158]

[0159] In some embodiments of the present application, in the second compound represented by Formula 3, are the same or different and are each independently selected from the group consisting of the following groups:

[0160]

[0161] Specifically, in the second compound represented by Formula 3, are the same or different and are each independently selected from the group consisting of the following groups:

[0162]

[0163]

[0164]

[0165] In some embodiments of the present application, in the second compound represented by Formula 2, each R3, each R4, each R5, and each R6 are the same or different, and are independently selected from deuterium, phenyl, or pentadeuterophenyl.

[0166] In some embodiments of the present application, in the second compound represented by Formula 3, each R7, each R8, and each R9 are the same or different, and are independently selected from deuterium, phenyl, or pentadeuterophenyl.

[0167] In some embodiments of the present application, the second compound represented by Formula 2 is selected from the compounds shown as A1 to B108 in Claim 14.

[0168] In some embodiments of the present application, the second compound represented by Formula 3 is selected from the compounds shown as a1 to aa206 in Claim 14.

[0169] The present application does not particularly limit the relative contents of the two types of compounds in the provided composition, and can be selected according to the specific application of the organic electroluminescent device.

[0170] In some embodiments of the present application, the evaporation rate ratio (%) of the first compound (compound of Formula 1) and the second compound (compound of Formula 2 or Formula 3) in the composition can be 1:99, 20:80, 30:70, 40:60, 45:55, 50:50, 55:45, 60:40, 70:30, 80:20, 99:1, etc.

[0171] In some preferred embodiments of the present application, the evaporation rate ratio (%) of the composition (compound of Formula 1) and the second compound (compound of Formula 2 or Formula 3) is 30:70, 40:60, 45:55, 50:50, 55:45, 60:40, 70:30.

[0172] In some other embodiments of the present application, the mass ratio of the first compound (compound of Formula 1) to the second compound (compound of Formula 2 or Formula 3) in the composition is from 1:99 to 99:1, preferably from 10:90 to 90:10, more preferably from 30:70 to 70:30, and still more preferably from 40:60 to 60:40.

[0173] In some preferred embodiments of the present application, the mass ratio of the first compound (compound of Formula 1) and the second compound (compound of Formula 2 or Formula 3) in the composition is 30:70 to 70:30.

[0174] In one embodiment of the present application, the organic electroluminescent device is a phosphorescent device.

[0175] In a specific embodiment of the present application, the organic electroluminescent device is a green phosphorescent organic electroluminescent device.

[0176] In some embodiments of the present application, the organic electroluminescent device sequentially includes an anode (ITO substrate), a hole transport layer, a light emission adjustment layer, an organic light emitting layer, an electron transport layer, an electron injection layer, a cathode (Mg-Ag mixture), and an organic cover layer.

[0177] In a specific embodiment of the present application, as Figure 1 shown, the organic electroluminescent device of the present application includes an anode 100, a cathode 200, and at least one functional layer 300 interposed between the anode layer and the cathode layer. The functional layer 300 includes a hole injection layer 310, a hole transport layer 320, a light emission adjustment layer 330, an organic light emitting layer 340, an electron transport layer 350, and an electron injection layer 360.

[0178] Optionally, the anode 100 includes the following anode materials, which are preferably materials with a large work function (work function) that contribute to 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); combinations of metals and oxides such as ZnO:Al or SnO2:Sb; or conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylenedioxy)thiophene] (PEDT), polypyrrole, and polyaniline, but are not limited thereto. Preferably, a transparent electrode including indium tin oxide (ITO) as the anode is included.

[0179] Optionally, the hole transport layer 320 may include one or more hole transport materials, and the hole transport materials may be selected from carbazole polymers, carbazole-linked triarylamine compounds, or other types of compounds. The present application does not make special limitations on this. For example, in some embodiments of the present application, the hole transport layer 320 is composed of HT-1.

[0180] Optionally, the light emission adjustment layer 330 (the light emission adjustment layer is also referred to as a hole adjustment layer, an electron blocking layer, a hole assisting layer, a hole buffer layer, a light emission assisting layer, or a second hole transport layer) may include one or more hole transport materials, and the hole transport materials may be selected from carbazole polymers, carbazole-linked triarylamine compounds, or other types of compounds. The present application does not make special limitations on this. For example, in some embodiments of the present application, the light emission adjustment layer 330 is composed of HT-2 or HT-3.

[0181] 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. The holes and electrons injected into the organic light-emitting layer 330 can recombine in the organic light-emitting layer 340 to form excitons. 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.

[0182] The guest material of the organic light-emitting layer 340 may be a compound or its derivative having a condensed aryl ring, a compound or its derivative having a heteroaryl ring, an aromatic amine derivative, or other materials, and the present application does not make special restrictions thereon.

[0183] In some embodiments of the present application, the organic electroluminescent device is a green organic electroluminescent device. The organic electroluminescent device includes an organic light-emitting layer, and the organic light-emitting layer includes the organic compound of the present application, the second compound represented by Formula 2 or Formula 3, and the guest material GD-01.

[0184] 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. The electron transport materials may be selected from benzimidazole derivatives, oxadiazole derivatives, quinoxaline derivatives, or other electron transport materials, and the present application does not make special limitations thereon. For example, in some embodiments of the present application, the electron transport layer 350 may be composed of ET-1 and LiQ.

[0185] Optionally, the cathode 200 includes the following cathode materials, which are materials with a small work function that contribute to electron injection into the functional layer. Specific examples of the cathode materials include: metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or their alloys; or multi-layer 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 containing silver and magnesium is included as the cathode.

[0186] Optionally, a hole injection layer 310 may further 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 selected from benzidine derivatives, starburst arylamine compounds, phthalocyanine derivatives, or other materials, and the present application does not make special restrictions thereon. In some embodiments of the present application, the hole injection layer 310 may be composed of PD-1 and HT-1.

[0187] Optionally, an electron injection layer 360 may also 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 complexes of alkali metals and organic compounds. In some embodiments of the present application, the electron injection layer 360 may include ytterbium (Yb).

[0188] A fourth aspect of the present application further provides an electronic device, which includes the organic electroluminescent device described in the present application.

[0189] For example, as Figure 2 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 may be a display device, a lighting device, an optical communication device or other types of electronic devices, and may include, for example, but 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, which will not be elaborated herein.

[0190] The present application will be described in detail below in conjunction with embodiments. However, the following description is for explaining the present application and does not limit the scope of the present application in any way.

[0191] Synthesis of intermediate A-1:

[0192]

[0193] Under nitrogen protection, SMA-1 (20.00 g, 65.10 mmol), SMB-1 (11.35 g, 65.10 mmol), tetrakis(triphenylphosphine)palladium (3.76 g, 3.25 mmol), anhydrous potassium carbonate (17.99 g, 130.17 mmol), tetrabutylammonium bromide (2.09 g, 6.51 mmol), toluene (160 mL), absolute ethanol (80 mL) and deionized water (40 mL) were successively added to a three-necked flask. Stirring and heating were started, and the temperature was raised to reflux for 16 h. After the system was cooled to room temperature, it was extracted with dichloromethane (100 mL × 3 times). The organic phases were combined, dried over anhydrous sodium sulfate, filtered, and the solvent was removed by distillation under reduced pressure to obtain a crude product. The crude product was purified by silica gel column chromatography using a mixed solution of n-heptane / dichloromethane as the mobile phase to obtain intermediate A-1 (16.5 g, yield: 71%).

[0194] Referring to the same method as intermediate A-1, reactant A in Table 1 below was used to replace intermediate SMA-1, and reactant B was used to replace intermediate SMB-1 to synthesize the intermediates shown in Table 1 below:

[0195] Table 1

[0196]

[0197]

[0198] Synthesis of Intermediate B-1:

[0199]

[0200] Dissolve A-1 (16.50 g, 46.24 mmol) in 1,4-dioxane (200 mL), then add tris(dibenzylideneacetone)dipalladium(0) (2.12 g, 2.31 mmol), potassium acetate (9.07 g, 2.31 mmol), bis(pinacolato)diboron (11.74 g, 46.24 mmol), and x-phos (1.89 g, 4.62 mmol). Start stirring and heating, and raise the temperature to reflux for 16 h. After the system cools to room temperature, extract with dichloromethane (100 mL × 3 times), combine the organic phases, dry over anhydrous sodium sulfate, filter, and then remove the solvent by distillation under reduced pressure to obtain the crude product. Purify the crude product by silica gel column chromatography using a n-heptane / dichloromethane mixed solution as the mobile phase to obtain Intermediate B-1 (12.43 g, yield: 60%).

[0201] Referring to the synthesis method of Intermediate B-1, replace A-1 with Reactant C in Table 2 below to synthesize the intermediate shown in Table 2 below:

[0202] Table 2

[0203]

[0204]

[0205] Synthesis of Intermediate C-1:

[0206]

[0207] Under nitrogen protection, B-1 (12.43 g, 27.72 mmol), SMC-1 (7.42 g, 27.72 mmol), tetrakis(triphenylphosphine)palladium (1.60 g, 1.39 mmol), anhydrous potassium carbonate (7.66 g, 55.45 mmol), tetrabutylammonium bromide (0.89 g, 2.77 mmol), toluene (80 mL), anhydrous ethanol (40 mL) and deionized water (20 mL) were successively added to a three-necked flask. Stirring and heating were started, and the temperature was raised to reflux for 16 h. After the system was cooled to room temperature, it was extracted with dichloromethane (100 mL × 3 times). The organic phases were combined, dried over anhydrous sodium sulfate, filtered, and the solvent was removed by distillation under reduced pressure to obtain a crude product. The crude product was purified by silica gel column chromatography using a n-heptane / dichloromethane mixed solution as the mobile phase to obtain intermediate C-1 (10.44 g, yield: 68%).

[0208] Referring to the synthesis method of intermediate C-1, reactant D in Table 3 below was used to replace B-1, and reactant E was used to replace SMC-1 to synthesize the intermediates shown in Table 3 below:

[0209] Table 3

[0210]

[0211]

[0212]

[0213]

[0214] Synthesis of Compound 89:

[0215]

[0216] C-1 (10.00 g, 18.06 mmol) and SMD-1 (5.69 g, 32.51 mmol) were dissolved in N-methylpyrrolidone (100 mL), then potassium phosphate tribasic (11.50 g, 54.18 mmol) was added. Stirring and heating were started, and the temperature was raised to reflux for 16 h. After the system was cooled to room temperature, it was extracted with dichloromethane (100 mL × 3 times). The organic phases were combined, dried over anhydrous sodium sulfate, filtered, and the solvent was removed by distillation under reduced pressure to obtain a crude product. The crude product was purified by silica gel column chromatography using a n-heptane / dichloromethane mixed solution as the mobile phase to obtain Compound 89 (8.31 g, yield: 65%).

[0217] Referring to the synthesis method of Compound 89, reactant F in Table 4 below was used to replace C-1, and reactant G was used to replace SMD-1 to synthesize the compounds shown in Table 4 below:

[0218] Table 4

[0219]

[0220]

[0221]

[0222]

[0223]

[0224]

[0225] The synthesis process of intermediate IM-a-nh in Table 4 is as follows:

[0226] Synthesis of intermediate IM-a-no:

[0227]

[0228] Under nitrogen protection, 2,3-dichloronitrobenzene (20.0 g; 104.2 mmol), d5-phenylboronic acid pinacol ester (47.9 g; 229.2 mmol), tetrakis(triphenylphosphine)palladium (4.8 g; 4.2 mmol), potassium carbonate (57.6 g; 416.7 mmol), tetrabutylammonium bromide (13.4 g; 41.2 mmol), toluene (320 mL), ethanol (80 mL) and deionized water (80 mL) were added to a round-bottom flask, and the temperature was raised to 75 °C - 80 °C, and the mixture was stirred and reacted for 72 hours. The reaction solution was cooled to room temperature, deionized water was added, and liquid separation was carried out. The organic phase was washed with water and then dried with 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 mixed solution to obtain a colorless oily substance intermediate IM-a-no (17.7 g; yield: 60%).

[0229] Synthesis of intermediate IM-a-nh:

[0230]

[0231] Under nitrogen protection, intermediate IM-a-no (16.0 g; 56.1 mmol), triphenylphosphine (36.8 g; 140.2 mmol), and o-dichlorobenzene (150 mL) were added to a round-bottom flask, and the temperature was raised to 175 °C - 180 °C under stirring conditions and reacted for 36 hours. The reaction solution was cooled to room temperature, deionized water was added, and liquid separation was carried out. The organic phase was washed with water and then dried with anhydrous magnesium sulfate, and the solvent was removed under high-temperature reduced pressure conditions. The obtained crude product was purified by silica gel column chromatography using a dichloromethane / n-heptane mixed solution to obtain a white solid intermediate IM-a-nh (9.2 g; yield: 65%).

[0232] The mass spectrometry data of some compounds are shown in Table 5 below

[0233] Table 5

[0234]

[0235]

[0236] The NMR data of some compounds are shown in Table 6 below

[0237] Table 6

[0238]

[0239] Synthesis of some second compounds

[0240] Synthesis of compound aa3:

[0241]

[0242] Under nitrogen protection, raw material a-1 (20.0 g; 48.9 mmol), raw material b-1 (15.1 g; 48.9 mmol), tris(dibenzylideneacetone)dipalladium(0) (0.4 g; 0.5 mmol), 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (0.4 g; 1.0 mmol), sodium tert-butoxide (7.0 g; 73.4 mmol) and xylene (200 mL) were added to a round-bottom flask, and the mixture was stirred at 140 °C for 6 hours. After cooling to room temperature, the reaction solution was washed with water and separated by liquid separation. The organic phase was 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 a dichloromethane / n-heptane mixed solution as the eluent, and then the product was recrystallized and purified using a toluene / n-heptane mixed solution to obtain white solid compound aa3 (23.1 g; yield: 74%).

[0243] Referring to the synthesis method of compound aa3, the compounds shown in Table 7 below were synthesized using reactant a in the following table to replace compound b-1:

[0244] Table 7

[0245]

[0246] Synthesis of compound a3

[0247]

[0248] Under nitrogen protection, raw material a-1 (20.0 g; 48.9 mmol), raw material b-1 (15.1 g; 48.9 mmol), tris(dibenzylideneacetone)dipalladium(0) (0.4 g; 0.5 mmol), 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (0.4 g; 1.0 mmol), sodium tert-butoxide (7.0 g; 73.4 mmol) and xylene (200 mL) were added to a round-bottom flask, and the mixture was stirred at 140 °C for 6 hours. After cooling to room temperature, the reaction solution was washed with water and separated by liquid separation. The organic phase was dried over 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 a dichloromethane / n-heptane mixed solution as an eluent, and then the product was recrystallized and purified using a toluene / n-heptane mixed solution to obtain a white solid compound aa3 (23.1 g; yield: 74%).

[0249]

[0250] Trifluoromethanesulfonic anhydride (86.8 g, 307.8 mmol) and heavy water (30.8 g, 1538.9 mmol) were added at 0 °C, and the mixture was stirred for 5 hours to prepare a solution. aa3 (20 g, 31.4 mmol) was added to 120 mL of 1,2,4-trichlorobenzene, and the mixture was stirred. Then, the prepared mixed solution of trifluoromethanesulfonic anhydride and heavy water was slowly added dropwise to the mixed solution of aa3 and 1,2,4-trichlorobenzene, and the mixture was stirred while heating to 140 °C, and then maintained at this temperature. After reacting for 14 hours, the reaction mixture was cooled to room temperature, and the organic layer and the aqueous layer were separated. Then, the organic layer was neutralized with an aqueous potassium carbonate solution. After washing twice with water, the organic layer was separated, anhydrous magnesium sulfate was added thereto, stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain compound a3 (10.97 g; yield: 54%).

[0251] Referring to the synthesis method of compound a3, the compounds shown in Table 8 below were synthesized using reactant b in the following table to replace compound a-1 and reactant c to replace compound b-1:

[0252] Table 8

[0253]

[0254]

[0255] The mass spectrometry data of some second compounds are shown in Table 9 below

[0256] Table 9

[0257] Compound Mass spectrometry data Compound Mass spectrometry data Compound aa3 <![CDATA[m / z = 637.3 [M+H] + > Compound aa1 <![CDATA[m / z = 561.2 [M+H] + > Compound a3 <![CDATA[m / z = 647.3 [M+H] + > Compound a42 <![CDATA[m / z = 647.3 [M+H] + > Compound a1 <![CDATA[m / z = 571.3 [M+H] + > Compound a65 <![CDATA[m / z = 660.3 [M+H] + >

[0258] Preparation of Organic Electroluminescent Devices

[0259] Example 1: Preparation of Green Organic Electroluminescent Devices

[0260] The device was prepared through the following process

[0261] On an experimental substrate with a thickness of ITO / Ag / ITO Surface treatment was carried out using ultraviolet, ozone, and O2:N2 plasma to increase the work function of the anode, and the surface of the experimental substrate could be cleaned with an organic solvent to remove impurities and oil stains on the surface of the experimental substrate.

[0262] On the experimental substrate, compound HT-1 and PD-1 were co-evaporated at an evaporation rate ratio of 97%:3% to form a hole injection layer with a thickness of Then, compound HT-1 was evaporated on the hole injection layer to form a hole transport layer with a thickness of

[0263] Compound HT-2 was evaporated on the hole transport layer to form a light emission adjustment layer with a thickness of

[0264] On the light emission adjustment layer, compound aa3 (the second compound), compound 89 (the first compound), and GD-01 (the guest material) were co-evaporated at an evaporation rate ratio of 60%:40%:10% to form an organic light-emitting layer with a thickness of

[0265] On the organic light-emitting layer, compound ET-1 and LiQ were co-evaporated at an evaporation rate ratio of 50%:50% to form an electron transport layer with a thickness of

[0266] Yb was evaporated on the electron transport layer to form an electron injection layer with a thickness of Then, on the electron injection layer, magnesium (Mg) and silver (Ag) were co-evaporated at an evaporation rate ratio of 10%:90% to form a cathode with a thickness of

[0267] Finally, compound CP-1 was evaporated on the cathode to form an organic covering layer with a thickness of Thereby completing the preparation of the green organic electroluminescent device.

[0268] Examples 2 to 16

[0269] ​​​​​An organic electroluminescent device was prepared using the same method as in Example 1, except that when preparing the organic light-emitting layer, the second and first compound combinations and evaporation rate ratios in Table 10 were used to replace the second and first compound combinations and evaporation rate ratios in Example 1.

[0270] Comparative Examples 1-2

[0271] An organic electroluminescent device was prepared using the same method as in Example 1, except that when preparing the organic light-emitting layer, the second and first compound combinations and evaporation rate ratios in Table 10 were used to replace the second and first compound combinations and evaporation rate ratios in Example 1.

[0272] Among them, when preparing the devices of the above examples and comparative examples, the compound structures used are as follows:

[0273]

[0274] The green organic electroluminescent devices prepared in Examples 1-16 and Comparative Examples 1-2 were subjected to performance tests. Specifically, the IVL performance of the devices was tested under the condition of 15 mA / cm 2 , and the device life of T95 was tested under the condition of 20 mA / cm 2 . The test results are shown in Table 10 below

[0275] Table 10

[0276]

[0277] Referring to Table 10 above, it can be seen that when the compounds of the present application are used in the light-emitting layer of green organic electroluminescent devices, the device performance can be greatly improved. Specifically, compared with Comparative Examples 1 and 2, the current efficiency of the organic electroluminescent devices in Examples 1-16 was increased by at least 11.5%, and the life was increased by at least 14.1%.

[0278] Compared with Comparative Examples 1 and 2, when the compounds of the present application are used as the host material of green organic electroluminescent devices, the life and current efficiency of the devices have been significantly improved. Compared with Compound I and Compound II, the nitrogen-containing compound triphenylene / phenanthrene group of the present application is located at the para position of carbazole / triazine. This connection method enables the compound to have a good spatial D-A conjugation effect, effectively reducing the ΔE ST (energy level difference between the first excited singlet state and the first excited triplet state) of the material and improving the energy transfer efficiency of the compound. However, the connection method of Compound I results in too large steric hindrance of the compound, which slows down the carrier transport and thus reduces the efficiency.

[0279] Example 17: Preparation of Green Organic Electroluminescent Device

[0280] The device is prepared through the following process

[0281] On an experimental substrate with a thickness of ITO / Ag / ITO The surface is treated with ultraviolet, ozone, and O2:N2 plasma to increase the work function of the anode, and the surface of the experimental substrate can be cleaned with an organic solvent to remove impurities and oil stains on the surface of the experimental substrate.

[0282] On the experimental substrate, the compounds HT-1 and PD-1 are co-evaporated at an evaporation rate ratio of 97%:3% to form a hole injection layer with a thickness of Then, the compound HT-1 is evaporated on the hole injection layer to form a hole transport layer with a thickness of The compound HT-3 is evaporated on the hole transport layer to form a light emission adjustment layer with a thickness of

[0283] On the light emission adjustment layer, the compound A8 (the second compound), the compound 170 (the first compound), and GD-01 (the guest material) are co-evaporated at an evaporation rate ratio of 60%:40%:10% to form an organic light-emitting layer with a thickness of

[0284] On the organic light-emitting layer, the compounds ET-1 and LiQ are co-evaporated at an evaporation rate ratio of 50%:50% to form an electron transport layer with a thickness of

[0285] Yb is evaporated on the electron transport layer to form an electron injection layer with a thickness of Then, on the electron injection layer, magnesium (Mg) and silver (Ag) are co-evaporated at an evaporation rate ratio of 10%:90% to form a cathode with a thickness of

[0286] Finally, the compound CP-1 is evaporated on the cathode to form an organic covering layer with a thickness of Thereby completing the preparation of the green organic light-emitting device.

[0287] Examples 18 to 32

[0288] Except that when preparing the organic light-emitting layer, the combination of the second compound and the first compound and the evaporation rate ratio in Table 11 are used to replace the combination of the second and first compounds and the evaporation rate ratio in Example 17, an organic light-emitting device is prepared by the same method as in Example 17.

[0289] Comparative Examples 3 to 5

[0290] ​​​​An organic electroluminescent device was prepared using the same method as in Example 17, except that in the preparation of the organic light-emitting layer, the second and first compound combinations and evaporation rate ratios in Table 11 were used instead of those in Example 17.

[0291] Some of the second compounds used are shown below. According to the description in Patent Document CN103518271A, Compound A8 was obtained; according to the description in Patent Document KR1020170024418A, Compound A69 was obtained; according to the description in Patent Document CN115894462A, Compound B23 was obtained; according to the description in Patent Document CN115368293A, Compound B101 was obtained.

[0292]

[0293] Among them, when preparing the devices of the above examples and comparative examples, the compound structures used are as follows:

[0294]

[0295] Compound Ⅴ

[0296] The performance of the green organic electroluminescent devices prepared in Examples 17 to 32 and Comparative Examples 3 to 5 was tested. Specifically, the IVL performance of the devices was tested under the condition of 15 mA / cm 2 and the device lifetime of T95 was tested under the condition of 20 mA / cm 2 . The test results are shown in Table 11 below.

[0297] Table 11

[0298]

[0299] Referring to Table 11 above, it can be seen that when the compounds of the present application are used in the light-emitting layer of green organic electroluminescent devices, the device performance can be greatly improved. Specifically, compared with Comparative Examples 3 to 5, the current efficiency of the organic electroluminescent devices in Examples 17 to 32 was increased by at least 14.7%, and the lifetime was increased by at least 22.3%.

[0300] Compared with Comparative Examples 3 to 5, when the compounds of the present application are used as the host material of green organic electroluminescent devices, the lifetime and current efficiency of the devices have been significantly improved. Specifically, compared with Compound Ⅲ, the compounds of the present application are located at the connection of carbazole / triazine with triphenylene / phenanthryl instead of naphthyl. Compared with naphthyl, phenanthryl / triphenylene has a higher T1 energy level and aromaticity, which is helpful for carrier and energy transfer.

[0301] Compared with Compound V, in the compounds of the present application, the carbazolyl group and the triazinyl group are located at the ortho positions of the phenylene group, and the phenanthryl group / triphenylene is located at the para position of the carbazolyl group / triazinyl group. This connection mode endows the compounds with a good spatial D-A conjugation effect, effectively reducing the ΔE ST (energy level difference between the first excited singlet state and the first excited triplet state) of the material and improving the energy transfer efficiency of the compounds. Moreover, the compounds of the present application have a relatively high T1 energy level and aromaticity, which contribute to the carrier and energy transfer. Therefore, the compounds of the present application have a relatively high current efficiency and service life.

[0302] The above has described in detail some embodiments of the present application in conjunction with the accompanying drawings. However, the present application is not limited to the specific details in the above embodiments. Within the scope of the technical concept of the present application, various simple modifications can be made to the technical solutions 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 compound has the structure shown in Formula 1: One of A and B is hydrogen, and the other is selected from the groups shown in Formula 1-1; Ring C is selected from a naphthalene ring or a phenanthrene ring; D represents deuterium; n is the number of Ds, selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11 or 12; Each R1 and each R2 are the same or different and are each independently selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms, a deuterated aryl group having 6 to 20 carbon atoms or a halogenated aryl group having 6 to 20 carbon atoms; n1 is the number of R1s, selected from 0, 1, 2, 3 or 4. When n1 is greater than 1, any two R1s are the same or different; n2 is the number of R2s, selected from 0, 1, 2, 3 or 4. When n2 is greater than 1, any two R2s are the same or different; L1 and L2 are the same or different and are each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms; Ar1 and Ar2 are the same or different and are each 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 L1, L2, Ar1 and Ar2 are the same or different and are each independently selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, a heteroaryl group having 3 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms, a deuterated aryl group having 6 to 20 carbon atoms or a halogenated aryl group having 6 to 20 carbon atoms.

2. The organic compound according to claim 1, characterized in that, One of A and B is hydrogen, and the other is selected from the group consisting of the following groups: Optionally, one of A and B is hydrogen, and the other is selected from the group consisting of the following groups:

3. The organic compound according to claim 1, wherein Each R1 and each R2 are the same or different and are each independently selected from deuterium, fluorine, a cyano group, methyl, ethyl, n-propyl, isopropyl, tert-butyl, phenyl or pentadeuterophenyl.

4. The organic compound according to claim 1, characterized in that, L1 and L2 are the same or different and are each independently selected from a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted carbazolylene group, a substituted or unsubstituted dibenzofuranylene group, a substituted or unsubstituted dibenzothiophenylene group; Optionally, the substituents in L1 and L2 are the same or different and are each independently selected from deuterium, fluorine, a cyano group, methyl, ethyl, n-propyl, isopropyl, tert-butyl, phenyl or pentadeuterophenyl.

5. The organic compound according to claim 1, wherein Ar1 and Ar2 are the same or different and are each independently selected from a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group; Optionally, the substituents in Ar1 and Ar2 are the same or different and are each independently selected from deuterium, fluorine, a cyano group, methyl, ethyl, n-propyl, isopropyl, tert-butyl, phenyl or pentadeuterophenyl.

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

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

8. A composition, characterized in that, The composition comprises a first compound and a second compound; The first compound is selected from the organic compounds described in any one of claims 1 to 7, and the second compound is selected from the structures shown in Formula 2 or Formula 3: 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; n3 is the number of R3, and is selected from 0, 1, 2, 3 or 4. When n3 is greater than 1, any two R3 are the same or different; n4 is the number of R4, and is selected from 0, 1, 2 or 3. When n4 is greater than 1, any two R4 are the same or different; n5 is the number of R5, and is selected from 0, 1, 2 or 3. When n5 is greater than 1, any two R5 are the same or different; n6 is the number of R6, and is selected from 0, 1, 2, 3 or 4. When n6 is greater than 1, any two R6 are the same or different; n7 is the number of R7, and is selected from 0, 1, 2, 3 or 4. When n7 is greater than 1, any two R7 are the same or different; n8 is the number of R8, and is selected from 0, 1 or 2. When n8 is greater than 1, any two R8 are the same or different; n9 is the number of R9, and is selected from 0, 1, 2, 3 or 4. When n9 is greater than 1, any two R9 are the same or different; 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 3* carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 3* carbon atoms; Ar3, Ar4, Ar5 and Ar6 are the same or different, and are independently selected from a substituted or unsubstituted aryl group having 6 to 3* carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 3* carbon atoms; The substituents in L3, L4, L5, L6, Ar3, Ar4, Ar5 and Ar6 are the same or different, and are independently selected from deuterium, a cyano group, a halogen group, an alkyl group having 1 to 10 carbon atoms, a halogenated alkyl group having 1 to 10 carbon atoms, a deuterated alkyl group having 1 to 10 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 cycloalkyl group having 3 to 10 carbon atoms.

9. The composition according to claim 8, wherein 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 carbazolylene group, a substituted or unsubstituted dibenzofuranylene group, a substituted or unsubstituted dibenzothiophenylene group, The substituents in L3 and L4 are the same or different, and are independently selected from deuterium, fluorine, a cyano group, methyl, ethyl, n-propyl, isopropyl, tert-butyl or phenyl; Optionally, Ar3 and Ar4 are the same or different and are each independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted fluorenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted quaterphenyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, The substituents in Ar3 and Ar4 are the same or different and are each 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, characterized in that, In the second compound represented by Formula 3, L5 and L6 are the same or different and are each independently selected from a single bond, substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted biphenylene, substituted or unsubstituted terphenylene, substituted or unsubstituted carbazolylene, substituted or unsubstituted dibenzofuranylene, substituted or unsubstituted dibenzothiophenylene, The substituents in L5 and L6 are the same or different and are each independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl or phenyl; Optionally, Ar5 and Ar6 are the same or different and are each independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted fluorenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted quaterphenyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, The substituents in Ar5 and Ar6 are the same or different and are each 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, characterized in that, in the second compound shown in Formula 2 identical or different, and each independently selected from the group consisting of the following groups:

12. The composition according to claim 8, characterized in that, in the second compound shown in Formula 3 are the same or different and are each independently selected from the group consisting of the following groups:

13. The composition according to claim 8, wherein In the second compound represented by Formula 2, each R3, each R4, each R5 and each R6 are the same or different and are each independently selected from deuterium, phenyl or pentadeuterated phenyl; Optionally, in the second compound represented by Formula 3, each R7, each R8 and each R9 are the same or different and are each independently selected from deuterium, phenyl or pentadeuterated phenyl.

14. The composition according to claim 8, 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. An organic electroluminescent device, characterized in that, Comprising an anode and a cathode which are oppositely arranged, and a functional layer disposed between the anode and the cathode; The functional layer contains 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 contains an organic light-emitting layer, and the organic light-emitting layer contains 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 further includes a hole injection layer, a hole transport layer, a light emission adjustment layer, an electron transport layer and an electron injection layer.

16. An electronic device, characterized in that, Comprising the organic electroluminescent device according to claim 15.

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