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, 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 30 carbon atoms;

[0008] Ar1 and Ar2 are the same or different and are 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;

[0009] The substituents in 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, halogenated aryl group having 6 to 20 carbon atoms or cycloalkyl group having 3 to 10 carbon atoms.

[0010] 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 with a structure as shown in Formula 2.

[0011] 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.

[0012] 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.

[0013] The core structure of the organic compound of the present application is indole [2,3-C] carbazole, and the single-side benzene ring on the indole [2,3-C] carbazole is fully deuterated. The special asymmetric deuteration of the indole carbazole group in a specific condensation mode can not only effectively improve the stability of the molecular structure, but also 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 (especially a hole-type main material). 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.

[0014] Other features and advantages of the present application will be described in detail in the subsequent detailed description. BRIEF DESCRIPTION OF THE DRAWINGS

[0015] 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.

[0016] Figure 1 It is a schematic structural diagram of an organic electroluminescent device of the present application.

[0017] Figure 2 It is a structural schematic diagram of an electronic device of the present application.

[0018] Reference numerals

[0019] 100, anode 200, cathode 300, functional layer 310, hole injection layer

[0020] 320, hole transport layer 330, hole adjustment layer 340, organic light emitting layer 350, electron transport layer

[0021] 360. Electron injection layer 400. Electronic device DETAILED DESCRIPTION

[0022] 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.

[0023] 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:

[0024]

[0025] Wherein, 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 30 carbon atoms;

[0026] Ar1 and Ar2 are the same or different and are 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;

[0027] The substituents in 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, halogenated aryl group having 6 to 20 carbon atoms or cycloalkyl group having 3 to 10 carbon atoms.

[0028] In this application, the descriptions "each... independently is" and "... are independently" and "... are independently" are interchangeable and should be understood in a broad sense. They can mean that in different groups, the specific options expressed by the same symbols do not affect each other, or in the same group, the specific options expressed by the same symbols do not affect each other. For example, Wherein, each q is independently 0, 1, 2 or 3, and each R" is independently selected from hydrogen, deuterium, fluorine, and chlorine, which means: Formula Q-1 indicates that there are q substituents R" on the benzene ring, and each R" can be the same or different, and the options of each R" do not affect each other; Formula Q-2 indicates that there are q substituents R" on each benzene ring of biphenyl, and the number q of R" substituents on the two benzene rings can be the same or different, and each R" can be the same or different, and the options of each R" do not affect each other.

[0029] 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, etc. The number of substitutions can be 1 or more.

[0030] In the present application, "plurality" means more than 2, for example, 2, 3, 4, 5, 6, etc.

[0031] 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.

[0032] 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, quaterphenyl, 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.

[0033] 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.

[0034] 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 24 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.

[0035] In the present application, the aryl group as a substituent of Ar1, Ar2, L1, and L2 is, for example but not limited to, phenyl.

[0036] 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.

[0037] 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.

[0038] 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.

[0039] 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.

[0040] In the present application, the halogen group may be, for example, fluorine, chlorine, bromine, or iodine.

[0041] In the present application, specific examples of the haloalkyl group include, but are not limited to, trifluoromethyl.

[0042] In the present application, specific examples of deuterated alkyl groups include, but are not limited to, trideuterated methyl groups.

[0043] In the present application, specific examples of the deuterated aryl group include, but are not limited to, pentadeuterated phenyl, heptadeuterated naphthyl, and nonadeuterated biphenyl.

[0044] 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.

[0045] 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).

[0046]

[0047] 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).

[0048]

[0049] In some embodiments of the present application, 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.

[0050] Optionally, the substituents in 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, a phenyl group or a pentadeuterated phenyl group.

[0051] Further optionally, L1 and L2 are the same or different, and are independently selected from a single bond, and a substituted or unsubstituted arylene group having 6 to 12 carbon atoms.

[0052] In other embodiments of the present application, 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 or a substituted or unsubstituted terphenyl group.

[0053] 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 pentadeuterated phenyl.

[0054] In some embodiments of the present application, L1 and L2 are the same or different, and are independently selected from a single bond or the following groups:

[0055]

[0056] Specifically, L1 and L2 are the same or different and are independently selected from a single bond or the following groups:

[0057]

[0058] In some embodiments of the present application, Ar1 and Ar2 are the same or different, and are independently selected from a substituted or unsubstituted aryl group having 6 to 24 carbon atoms, or a substituted or unsubstituted heteroaryl group having 12 to 24 carbon atoms.

[0059] Optionally, the substituents in Ar1 and Ar2 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 or a pentadeuterated phenyl group.

[0060] In some other embodiments of the present application, Ar1 and Ar2 are the same or different, and are independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted quadriphenyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophene.

[0061] 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.

[0062] In some embodiments of the present application, Ar1 and Ar2 are the same or different, and are independently selected from substituted or unsubstituted groups G, wherein the unsubstituted group G is selected from the group consisting of the following groups:

[0063]

[0064]

[0065] in, represents a chemical bond; the substituted group G has one or more substituents, each of which is independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, phenyl or pentadeuterated phenyl, and when the number of substituents on the group W is greater than 1, each substituent is the same or different.

[0066] Optionally, Ar1 and Ar2 are the same or different and are independently selected from the following groups:

[0067]

[0068] Specifically, Ar1 and Ar2 are the same or different and are independently selected from the group consisting of the following groups:

[0069]

[0070]

[0071] In some embodiments of the present application, and The same or different, are independently selected from the following groups:

[0072]

[0073]

[0074] Specifically, and The same or different, are independently selected from the following groups:

[0075]

[0076]

[0077] In some embodiments of the present application, the organic compound is selected from the compound as shown in claim 7.

[0078] The second aspect of the present application also provides a composition comprising a first compound and a second compound;

[0079] The first compound has a structure shown in Formula 1, and the second compound has a structure shown in Formula 2:

[0080]

[0081] wherein L3, L4 and L5 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;

[0082] Ar4 and Ar5 are the same or different and are independently selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group;

[0083] D is deuterium;

[0084] n is the number of D, selected from 0, 1, 2, 3 or 4;

[0085] Ar6 is selected from

[0086] The substituents in L3, L4, L5, Ar4 and Ar5 are the same or different and are each 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.

[0087] In some embodiments of the present application, the second compound has a structure shown in Formula 2-1 or Formula 2-2:

[0088]

[0089] In formula 2-2, Ar4 contains at least one deuterium substituent.

[0090] In a preferred embodiment of the present application, the second compound has a structure shown in Formula 2-1.

[0091] In some specific embodiments of the present application, the second compound has a structure shown in Formula A, Formula B, Formula C, Formula D, Formula E, Formula F, Formula G or Formula H:

[0092]

[0093]

[0094] Among them, in Formula E, Formula F, Formula G and Formula H, Ar4 contains at least one deuterium substituent.

[0095] In a preferred embodiment of the present application, the second compound has a structure shown by Formula A, Formula B, Formula C or Formula D.

[0096] In some embodiments of the present application, in the second compound, L3, L4 and L5 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.

[0097] Optionally, the substituents in L3, L4 and L5 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.

[0098] In other embodiments of the present application, in the second compound, L3, L4 and L5 are the same or different, and are independently selected from a single bond, a substituted or unsubstituted phenylene, a substituted or unsubstituted naphthylene, and an unsubstituted biphenylene.

[0099] Optionally, the substituents in L3, L4 and L5 are the same or different, and are independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl or phenyl.

[0100] Optionally, L3, L4 and L5 are the same or different and are independently selected from a single bond or the following groups:

[0101]

[0102] Specifically, L3, L4 and L5 are the same or different and are independently selected from a single bond or the following groups:

[0103]

[0104] In some embodiments of the present application, Ar4 and Ar5 are the same or different, and are independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl.

[0105] Optionally, the substituents in Ar4 and Ar5 are the same or different, and are independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, phenyl or pentadeuterated phenyl.

[0106] In other embodiments of the present application, Ar4 and Ar5 are the same or different, and are independently selected from substituted or unsubstituted groups W, wherein the unsubstituted group W is selected from the group consisting of the following groups:

[0107]

[0108] in, represents a chemical bond; the substituted group W has one or more substituents, each of which is independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, phenyl or pentadeuterated phenyl, and when the number of substituents on the group W is greater than 1, each substituent is the same or different.

[0109] Optionally, Ar4 and Ar5 are the same or different and are independently selected from the group consisting of the following groups:

[0110]

[0111] Specifically, Ar4 and Ar5 are the same or different and are independently selected from the group consisting of the following groups:

[0112]

[0113] In some embodiments of the present application, and The same or different, are independently selected from the following groups:

[0114]

[0115]

[0116] Specifically, and The same or different, are independently selected from the following groups:

[0117]

[0118] In some embodiments of the present application, the second compound is selected from the compound as shown in claim 13.

[0119] Optionally, the composition is a mixture of the first compound and the second compound. For example, the first compound and the second compound can be uniformly mixed by mechanical stirring to form the mixture.

[0120] The present application does not specifically limit the relative contents of the two types of compounds in the composition, and can be selected according to the specific application of the organic electroluminescent device. Generally, based on the total weight of the composition, the mass percentage of the first compound can be 1% to 99%, and the mass percentage of the second compound can be 1% to 99%. For example, in the composition, the mass ratio of the first compound to the second compound 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.

[0121] In some embodiments of the present application, the composition consists of a first compound and a second compound, wherein the mass percentage of the first compound is 20% to 80%, and the mass percentage of the second compound is 20% to 80%, based on the total weight of the composition.

[0122] In some preferred embodiments, in the composition, based on the total weight of the composition, the mass percentage of the first compound is 40% to 70%, and the mass percentage of the second compound is 30% to 60%. In this case, the composition is applied to an organic electroluminescent device, which can make the device have both high luminous efficiency and long service life. Preferably, based on the total weight of the composition, the mass percentage of the first compound is 40% to 60%, and the mass percentage of the second compound is 40% to 60%. More preferably, the mass percentage of the first compound is 50% to 60%, and the mass percentage of the second compound is 40% to 50%.

[0123] The present application also provides the use of the composition as a main material of a light-emitting layer of an organic electroluminescent device.

[0124] 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.

[0125] 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.

[0126] In one embodiment of the present application, the functional layer includes an organic light-emitting layer, and the organic light-emitting layer includes the organic compound represented by Formula 1 of the present application or a composition including the first compound and the second compound.

[0127] In one embodiment of the present application, the organic electroluminescent device is a phosphorescent device.

[0128] In a specific embodiment of the present application, the organic electroluminescent device is a green organic electroluminescent device.

[0129] In some embodiments of the present application, the organic electroluminescent device includes an anode (ITO substrate), a hole transport layer, a hole adjustment 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.

[0130] 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 adjustment layer 330, an organic light-emitting layer 340, an electron transport layer 350 and an electron injection layer 360.

[0131] 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.

[0132] 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.

[0133] Optionally, the hole adjustment 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 adjustment layer 330 is composed of HT-2.

[0134] 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.

[0135] 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.

[0136] In some embodiments of the present application, the compound represented by Formula 1 of the present application is used as a hole-type host material of an organic light-emitting layer.

[0137] 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 Formula 1 of the present application, the second compound and the guest material GD-1.

[0138] 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.

[0139] 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.

[0140] 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.

[0141] 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).

[0142] A fourth aspect of the present application also provides an electronic device, which includes the organic electroluminescent device described in the present application.

[0143] For example, Figure 2 As shown, the electronic device provided in the present application is an electronic device 400, and the 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 electronic device 400 has the above organic electroluminescent device, it has the same beneficial effects, and the present application will not repeat them here.

[0144] 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.

[0145] Synthesis of intermediate a1-b1:

[0146]

[0147] 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, 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%).

[0148]

[0149] 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, heated to 180°C under 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; 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%).

[0150] Synthesis of intermediate a1-d1:

[0151]

[0152] 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 temperature was raised to 150°C and stirred for 18 hours. The reaction solution was cooled to room temperature and stirring was stopped. The reaction solution was washed with water and the organic phase was separated. The reaction solution 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 dichloromethane / n-heptane as the mobile phase to obtain a white solid intermediate a1-c1 (26.3 g; yield: 76%).

[0153]

[0154] 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%).

[0155] Referring to the synthesis method of intermediates a1-d1, reactant a in Table 1 below is used to replace 4-bromobiphenyl to obtain the intermediate shown in Structure 1, and the intermediate shown in Structure 1 is reacted with diboric acid pinacol ester to obtain the intermediate shown in Structure 2 in Table 1 below.

[0156] Table 1

[0157]

[0158]

[0159]

[0160]

[0161]

[0162]

[0163] The synthesis method of the reactant e7-d1-1 used to prepare the intermediate e7-d1 in Table 1 above is as follows:

[0164]

[0165] 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, heated to 76°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 the intermediate e7-d1-1 (20.2 g; yield: 68%).

[0166] Referring to the synthesis method of intermediate e7-d1-1, the reactant b in Table 2 below is substituted for dibenzo[b,d]thiophene-1-ylboronic acid, and the reactant c is substituted for p-bromoiodobenzene to synthesize the intermediate shown in Table 2 below:

[0167] Table 2

[0168]

[0169] Synthesis of intermediate a1-f1:

[0170]

[0171] 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, 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%).

[0172]

[0173] 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, heated to 180°C under 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; the obtained 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%).

[0174] Referring to the synthesis method of intermediate a1-f1, the intermediate a1-e1 is replaced by reactant d in Table 3 below to synthesize the intermediate shown in the fourth column of Table 2 below:

[0175] Table 3

[0176]

[0177]

[0178]

[0179]

[0180]

[0181]

[0182] Synthesis of compound a1

[0183]

[0184] 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%).

[0185] Referring to the synthesis method of compound a1, the reactant e in Table 4 below replaces the intermediate a1-b, and the reactant f replaces 4-bromobiphenyl to synthesize the compounds shown in Table 4 below:

[0186] Table 4

[0187]

[0188]

[0189]

[0190]

[0191]

[0192]

[0193]

[0194]

[0195]

[0196]

[0197]

[0198]

[0199]

[0200] The mass spectrometry data of some compounds are shown in Table 5 below

[0201] Table 5

[0202] Compound Mass spectrometry data Compound Mass spectrometry data Compound a1 <![CDATA[m / z=565.25(M+H) + ]]> Compound c1 <![CDATA[m / z=654.28(M+H) + ]]> Compound a3 <![CDATA[m / z=641.29(M+H) + ]]> Compound c2 <![CDATA[m / z=654.28(M+H) + ]]> Compound a6 <![CDATA[m / z=641.29(M+H) + ]]> Compound C33 <![CDATA[m / z=654.28(M+H) + ]]> Compound a7 <![CDATA[m / z=641.29(M+H) + ]]> Compound C34 <![CDATA[m / z=654.28(M+H) + ]]> Compound a8 <![CDATA[m / z=641.29(M+H) + ]]> Compound d1 <![CDATA[m / z=579.23(M+H) + ]]> Compound a9 <![CDATA[m / z=579.23(M+H) + ]]> Compound d2 <![CDATA[m / z=655.26(M+H) + ]]> Compound a10 <![CDATA[m / z=579.23(M+H) + ]]> Compound d3 <![CDATA[m / z=655.26(M+H) + ]]> Compound a13 <![CDATA[m / z=655.26(M+H) + ]]> Compound d5 <![CDATA[m / z=655.26(M+H) + ]]> Compound a14 <![CDATA[m / z=655.26(M+H) + ]]> Compound d6 <![CDATA[m / z=655.26(M+H) + ]]> Compound a15 <![CDATA[m / z=655.26(M+H) + ]]> Compound d7 <![CDATA[m / z=655.26(M+H) + ]]> Compound a16 <![CDATA[m / z=655.26(M+H) + ]]> Compound d26 <![CDATA[m / z=579.23(M+H) + ]]> Compound a21 <![CDATA[m / z=655.26(M+H) + ]]> Compound d27 <![CDATA[m / z=655.26(M+H) + ]]> Compound a22 <![CDATA[m / z=655.26(M+H) + ]]> Compound d28 <![CDATA[m / z=655.26(M+H) + ]]> Compound a23 <![CDATA[m / z=655.26(M+H) + ]]> Compound d30 <![CDATA[m / z=655.26(M+H) + ]]> Compound a24 <![CDATA[m / z=655.26(M+H) + ]]> Compound d31 <![CDATA[m / z=655.26(M+H) + ]]> Compound a33 <![CDATA[m / z=565.25(M+H) + ]]> Compound d32 <![CDATA[m / z=655.26(M+H) + ]]> Compound a35 <![CDATA[m / z=641.29(M+H) + ]]> Compound d51 <![CDATA[m / z=595.21(M+H) + ]]> Compound a38 <![CDATA[m / z=641.29(M+H) + ]]> Compound d53 <![CDATA[m / z=671.24(M+H) + ]]> Compound a45 <![CDATA[m / z=655.26(M+H) + ]]> Compound d77 <![CDATA[m / z=595.21(M+H) + ]]> Compound a46 <![CDATA[m / z=655.26(M+H) + ]]> Compound d78 <![CDATA[m / z=671.24(M+H) + ]]> Compound a47 <![CDATA[m / z=655.26(M+H) + ]]> Compound e1 <![CDATA[m / z=655.26(M+H) + ]]> Compound a48 <![CDATA[m / z=655.26(M+H) + ]]> Compound e2 <![CDATA[m / z=655.26(M+H) + ]]> Compound a53 <![CDATA[m / z=655.26(M+H) + ]]> Compound e15 <![CDATA[m / z=655.26(M+H) + ]]> Compound a54 <![CDATA[m / z=655.26(M+H) + ]]> Compound e16 <![CDATA[m / z=655.26(M+H) + ]]> Compound a55 <![CDATA[m / z=655.26(M+H) + ]]> Compound e27 <![CDATA[m / z=655.26(M+H) + ]]> Compound a56 <![CDATA[m / z=655.26(M+H) + ]]> Compound e28 <![CDATA[m / z=655.26(M+H) + ]]> Compound b1 <![CDATA[m / z=641.29(M+H) + ]]> Compound e40 <![CDATA[m / z=655.26(M+H) + ]]> Compound b2 <![CDATA[m / z=641.29(M+H) + ]]> Compound e41 <![CDATA[m / z=655.26(M+H) + ]]> Compound b9 <![CDATA[m / z=655.26(M+H) + ]]> Compound e52 <![CDATA[m / z=671.24(M+H) + ]]> Compound b10 <![CDATA[m / z=655.26(M+H) + ]]> Compound e64 <![CDATA[m / z=671.24(M+H) + ]]> Compound b35 <![CDATA[m / z=641.29(M+H) + ]]> Compound e77 <![CDATA[m / z=671.24(M+H) + ]]> Compound b36 <![CDATA[m / z=641.29(M+H) + ]]> Compound e90 <![CDATA[m / z=671.24(M+H) + ]]> Compound b43 <![CDATA[m / z=655.26(M+H) + ]]> Compound f1 <![CDATA[m / z=655.26(M+H) + ]]> Compound b44 <![CDATA[m / z=655.26(M+H) + ]]> Compound f2 <![CDATA[m / z=655.26(M+H) + ]]> Compound b69 <![CDATA[m / z=641.29(M+H) + ]]> Compound f15 <![CDATA[m / z=655.26(M+H) + ]]> Compound b70 <![CDATA[m / z=641.29(M+H) + ]]> Compound f16 <![CDATA[m / z=655.26(M+H) + ]]> Compound b77 <![CDATA[m / z=655.26(M+H) + ]]> Compound f28 <![CDATA[m / z=655.26(M+H) + <!-- 42 -->]]> Compound b78 <![CDATA[m / z=655.26(M+H) + ]]> Compound f29 <![CDATA[m / z=655.26(M+H) + ]]> Compound b101 <![CDATA[m / z=641.29(M+H) + ]]> Compound f41 <![CDATA[m / z=655.26(M+H) + ]]> Compound b102 <![CDATA[m / z=641.29(M+H) + ]]> Compound f42 <![CDATA[m / z=655.26(M+H) + ]]> Compound b109 <![CDATA[m / z=655.26(M+H) + ]]> Compound f55 <![CDATA[m / z=671.24(M+H) + ]]> Compound b110 <![CDATA[m / z=655.26(M+H) + ]]> Compound f67 <![CDATA[m / z=671.24(M+H) + ]]> Compound b133 <![CDATA[m / z=641.29(M+H) + ]]> Compound f78 <![CDATA[m / z=671.24(M+H) + ]]> Compound b134 <![CDATA[m / z=641.29(M+H) + ]]> Compound f93 <![CDATA[m / z=671.24(M+H) + ]]> Compound b141 <![CDATA[m / z=655.26(M+H) + ]]> Compound b142 <![CDATA[m / z=655.26(M+H) + ]]> Compound a66 <![CDATA[m / z=671.25(M+H) + ]]> Compound a65 <![CDATA[m / z=655.26(M+H) + ]]> Compound a68 <![CDATA[m / z=646.32(M+H) + ]]> Compound a67 <![CDATA[m / z=641.29(M+H) + ]]> Compound b166 <![CDATA[m / z=654.28(M+H) + ]]>

[0203] The NMR data of some compounds are shown in Table 6 below

[0204] Table 6

[0205]

[0206] Synthesis of the second compound

[0207] Synthesis of intermediate IM-a-no:

[0208]

[0209] Under nitrogen protection, 2,3-dichloronitrobenzene (20.0 g; 104.2 mmol), d5-phenylboronic acid pinacol ester (47.9 g; 229.2 mmol), tetrakistriphenylphosphine 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, the temperature was raised to 75°C-80°C, and the reaction was stirred for 72 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 then 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 IM-a-no (17.7 g; yield: 60%)

[0210] Referring to the synthesis method of intermediate IM-a-no, reactant A is used to replace 2,3-dichloronitrobenzene to synthesize the intermediates shown in Table 7 below:

[0211] Table 7

[0212]

[0213] Synthesis of intermediate IM-a-nh:

[0214]

[0215] Under nitrogen protection, the 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, heated to 175° C. to 180° C. under stirring, and reacted for 36 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 high temperature and reduced pressure; the obtained crude product was purified by silica gel column chromatography using a dichloromethane / n-heptane system to obtain a white solid intermediate IM-a-nh (9.2 g; yield: 65%).

[0216] The same method as intermediate IM-a-nh was used to synthesize the intermediates shown in Table 8 below by replacing intermediate IM-a-no with reactant B:

[0217] Table 8

[0218]

[0219] Synthesis of compound A5:

[0220]

[0221] Under nitrogen protection, the intermediate IM-a-nh (5.0 g; 19.8 mmol), 2-chloro-4-(dibenzofuran-3-yl)-6-phenyl-1,3,5-triazine (10.6 g; 29.7 mmol) and N,N-dimethylformamide (50 mL) were added to a round-bottom flask, stirred and cooled to -5°C to 0°C, sodium hydride (0.6 g; 23.4 mmol) was added, and after stirring and reacting at -5°C to 0°C for 1 hour, the temperature was raised to 20°C to 25°C and reacted for 24 hours; the reaction was stopped, the reaction solution was washed with water and then separated, 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 dichloromethane / n-heptane as an eluent, and then recrystallized and purified using a toluene / n-heptane solvent system to obtain a white solid compound A5 (8.0 g; yield: 70%)

[0222] Referring to the synthesis method of compound A5, the intermediate IM-a-nh 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 9 below:

[0223] Table 9

[0224]

[0225]

[0226] Synthesis of compound A45:

[0227]

[0228] Under nitrogen protection, intermediate IM-a-nh (5.0 g; 19.8 mmol), 2-(biphenyl-4-yl)-4-(4-chlorophenyl)-6-phenyl-1,3,5-triazine (8.7 g; 20.8 mmol), tris(dibenzylideneacetone)dipalladium (0.2 g; 0.2 mmol), 2-dicyclohexylphosphine-2',4',6'-triisopropylbiphenyl (0.4 g; 0.2 mmol), sodium tert-butoxide (2.9 g; 29. 7mmol) and xylene (50mL) were added into a round-bottom flask, and the mixture was stirred at 135°C to 140°C for 16 hours; the mixture was cooled to room temperature, the reaction solution was washed with water and then separated, 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 dichloromethane / n-heptane as an eluent, and the product was recrystallized and purified using a toluene / n-heptane solvent system to obtain a white solid compound A45 (9.4g; yield: 75%)

[0229] Referring to the synthesis method of compound A45, reactant E in Table 10 below was used to replace intermediate IM-a-nh, and reactant F was used to replace 2-(biphenyl-4-yl)-4-(4-chlorophenyl)-6-phenyl-1,3,5-triazine to synthesize the compounds shown in Table 10 below:

[0230] Table 10

[0231]

[0232]

[0233]

[0234]

[0235]

[0236]

[0237] Synthesis of intermediate T1:

[0238]

[0239] Under nitrogen protection, pentadeuterated bromobenzene (4.6 g; 28.4 mmol) and anhydrous tetrahydrofuran (60 mL) were added to a round-bottom flask. The temperature was lowered to -80°C to -75°C with stirring, and a solution of n-butyl lithium in n-hexane (14.2 mL, 28.4 mmol, 2M) was slowly added dropwise. The mixture was stirred at -80°C to -75°C for 30 minutes, and a solution of 2,4-dichloro-6-phenyl-1,3,5-triazine (8.0 g, 35.6 mmol) in tetrahydrofuran (60 mL) was slowly added dropwise at this temperature. The mixture was stirred at -80°C to -75°C for 1 hour, and then the temperature was slowly raised to 20°C to 25°C, and the mixture was stirred for 4 hours to stop the reaction. Deionized water (150 mL) and dichloromethane (200 mL) were added to the reaction solution, and the liquids were 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 system to obtain a white solid intermediate T1 (5.0 g; yield: 65%).

[0240] Referring to the synthesis method of intermediate T1, the reactant G in Table 11 below replaces the intermediate 2,4-dichloro-6-phenyl-1,3,5-triazine, and the reactant H replaces pentadeuterated bromobenzene to synthesize the intermediate shown in Table 11:

[0241] Table 11

[0242]

[0243] Synthesis of intermediate TL1:

[0244]

[0245] Under nitrogen protection, intermediate T1 (4.8 g; 17.6 mmol), 4-chlorophenylboronic acid (2.9 g; 18.5 mmol), tetrakistriphenylphosphine palladium (0.4 g; 0.4 mmol), potassium carbonate (4.9 g; 35.3 mmol), tetrabutylammonium chloride (1.1 g; 3.5 mmol), toluene (40 mL), ethanol (10 mL) and deionized water (10 mL) were added to a round-bottom flask and stirred at 75°C to 80°C for 8 hours. Cool to room temperature, add deionized water (100 ml) to the reaction solution, separate the liquids; wash the organic phase with water and dry it with anhydrous magnesium sulfate, remove the solvent under reduced pressure to obtain a crude product; purify the crude product by silica gel column chromatography with dichloromethane / n-heptane as eluent to obtain a white solid intermediate TL1 (4.7 g; yield: 77%)

[0246] Referring to the synthesis method of intermediate TL1, reactant L in Table 12 below is used to replace intermediate T1, and reactant M is used to replace 4-chlorophenylboronic acid to synthesize the intermediate shown in Table 12 below:

[0247] Table 12

[0248]

[0249]

[0250]

[0251] Synthesis of compound E1:

[0252]

[0253] The intermediate TL1 (4.5 g; 12.9 mmol), 4-phenylcarbazole (3.1 g; 12.9 mmol), tris(dibenzylideneacetone)dipalladium (0.1 g; 0.1 mmol), 2-dicyclohexylphosphine-2',4',6'-triisopropylbiphenyl (0.1 g; 0.3 mmol), sodium tert-butoxide (1.9 g; 19.4 mmol) and xylene (50 mL) were added to a round-bottom flask, and stirred at 135°C to 140°C for 12 hours under nitrogen protection; cooled to room temperature, the reaction solution was washed with water and then separated, 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 dichloromethane / n-heptane as the eluent, and then the product was recrystallized and purified using a toluene / n-heptane solvent system to obtain a white solid compound E1 (5.4 g; yield: 75%)

[0254] Referring to the synthesis method of compound E1, reactant O in Table 13 below was used to replace intermediate TL1, and reactant P was used to replace 4-phenylcarbazole to synthesize the compounds shown in Table 13 below:

[0255] Table 13

[0256]

[0257]

[0258]

[0259]

[0260]

[0261]

[0262] The mass spectrometry data of some compounds in the second compound are shown in Table 14 below

[0263] Table 14

[0264]

[0265]

[0266] The NMR data of some compounds in the second compound are shown in Table 15 below

[0267] Table 15

[0268]

[0269] Preparation of organic electroluminescent devices

[0270] Example 1: Preparation of green organic electroluminescent device

[0271] The device was prepared by the following process

[0272] 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 is prepared into an experimental substrate with a cathode overlapping area, an anode and an insulating layer pattern using a photolithography process. The surface can be treated with ultraviolet ozone and O2:N2 plasma to increase the work function of the anode, and 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.

[0273] Compound HT-1 and NDP-9 were co-deposited on the experimental substrate at a deposition ratio of 98%:2% 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.

[0274] On the hole transport layer, compound HT-2 was vacuum-deposited to form a layer with a thickness of Holes adjustment layer.

[0275] On the hole adjustment layer, the host material composition GH-1-1 and the compound GD-1 (guest material) were co-deposited at a deposition rate ratio of 100:10 to form a layer with a thickness of The main material composition GH-1-1 is prepared by mixing compound a1 and compound A45 in a mass ratio of 60:40.

[0276] On the light-emitting layer, compound ET-1 and LiQ were co-deposited at a thickness ratio of 1:1 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 evaporation rate of 1:9 and vacuum evaporated on the electron injection layer to form a layer with a thickness of cathode.

[0277] In addition, compound CP-1 is vacuum-evaporated on the cathode to form a layer with a thickness of A cover layer (CPL) is formed on the organic electroluminescent device to complete the manufacturing process.

[0278] Example 2 to Example 104

[0279] An organic electroluminescent device was prepared by the same method as in Example 1, except that the host material composition in Table 16 was used to replace the host material composition in Example 1 when preparing the light-emitting layer.

[0280] Comparative Examples 1 to 6:

[0281] An organic electroluminescent device was prepared by the same method as in Example 1, except that the host material composition in Table 16 was used to replace the host material composition in Example 1 when preparing the light-emitting layer.

[0282] Comparative Example 7

[0283] An organic electroluminescent device was prepared by the same method as in Example 1, except that Compound V was used to replace the host material composition in Example 1 when preparing the light-emitting layer.

[0284] In the above embodiments and comparative examples, the main material composition GH-XY used is obtained by mixing two compounds, and the specific composition is shown in Table 16, wherein the mass ratio refers to the mass ratio of the compound shown in the first column to the compound shown in the second column in the table. In conjunction with Table 16, it can be seen that taking the main material composition GH-1-1 as an example, GH-1-1 is a mixture of compound a1 and compound A45 at a mass ratio of 60:40; taking the main material GH-D-1 as an example, GH-D-1 is a mixture of compound I and compound III at a mass ratio of 60:40.

[0285] The compounds used to prepare the devices of each embodiment and comparative example are as follows:

[0286]

[0287] The green organic electroluminescent devices prepared in Examples 1-104 and Comparative Examples 1-7 were tested for performance. Specifically, at 10 mA / cm 2 The IVL performance of the device was tested under the conditions of T95 device life at 20mA / cm 2 The test was carried out under the conditions of

[0288] Table 16

[0289]

[0290]

[0291]

[0292]

[0293]

[0294]

[0295] As can be seen from the table 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 1-6, the current efficiency of the device of Example 1-104 is improved by at least 11%, and the life span is improved by at least 12.6%.

[0296] Compared with Comparative Example 7, the current, efficiency and life of the device in Examples 1-104 are significantly improved, and the voltage is also significantly reduced. The device current efficiency is improved by at least 62.7%, and the life is improved by at least 67.5%.

[0297] 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: Among them, 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 30 carbon atoms; Ar 1 and Ar 2 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 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, 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 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; Optionally, the 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, a phenyl group or a pentadeuterated phenyl group.

3. The organic compound according to claim 1, It is characterized in that 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, a substituted or unsubstituted biphenylene group or a substituted or unsubstituted terphenyl group; Optionally, the 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, phenyl or pentadeuterated 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 a substituted or unsubstituted aryl group having 6 to 24 carbon atoms and a substituted or unsubstituted heteroaryl group having 12 to 24 carbon atoms; Optionally, the Ar 1 and Ar 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, a phenyl group or a pentadeuterated phenyl group.

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 biphenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted quaterphenyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl; 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: Among them, L 3 , L 4 and L 5 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; Ar 4 and Ar 5 are the same or different and are independently selected from substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted dibenzofuranyl groups, and substituted or unsubstituted dibenzothiophenyl groups; D is deuterium; n is the number of D, selected from 0, 1, 2, 3 or 4; Ar 6 Selected from L 3 , L 4 , L 5 ,Ar 4 and Ar 5 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, L 3 , L 4 and L 5 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 3 , L 4 and L 5 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.

10. The composition according to claim 8, It is characterized in that In the second compound, L 3 , L 4 and L 5 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 an unsubstituted biphenylene group; Optionally, the L 3 , L 4 and L 5 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.

11. The composition according to claim 8, It is characterized in that In the second compound, Ar 4 and Ar 5 are the same or different and are independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothienyl; Optionally, the Ar 4 and Ar 5 The substituents in the group are the same or different and are independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, phenyl or pentadeuterated phenyl.

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

13. The composition according to claim 8, It is characterized in that The second compound is selected from the group consisting of the following compounds:

14. 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 13; 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 13.

15. Electronic devices, It is characterized in that The organic electroluminescent device according to claim 14 is included.

Images