Nitrogen-containing compound, organic electroluminescent element, and electronic device

Abstract

The invention belongs to the technical field of organic electroluminescence, and relates to a nitrogen-containing compound, an organic electroluminescence device and an electronic device.The nitrogen-containing compound has a structure shown in the formula 1, and when the nitrogen-containing 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 a nitrogen-containing compound and an organic electroluminescent device and an electronic device comprising the nitrogen-containing 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 layers of 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 electron blocking 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 present application aims to provide a nitrogen-containing compound and an organic electroluminescent device and an electronic device comprising the nitrogen-containing compound, wherein the nitrogen-containing 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, a nitrogen-containing compound is provided, wherein the nitrogen-containing compound has a structure as shown in Formula 1:

[0006]

[0007] Wherein, D represents deuterium;

[0008] n, m and p are the same or different and are independently selected from 0, 1, 2, 3 or 4;

[0009] q is selected from 0, 1, 2, 3, 4, 5, 6 or 7;

[0010] L is selected from a single bond, phenylene or deuterium-substituted phenylene;

[0011] 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, and a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms;

[0012] 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;

[0013] The substituents in L1, L2, 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 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms, a heteroaryl group having 3 to 20 carbon atoms, a deuterated aryl group having 6 to 20 carbon atoms, and a halogenated aryl group having 6 to 20 carbon atoms.

[0014] According to a second aspect of the present application, an organic electroluminescent device is provided, comprising an anode and a cathode arranged opposite to each other, and a functional layer arranged between the anode and the cathode; the functional layer comprises the above-mentioned nitrogen-containing compound.

[0015] According to a third aspect of the present application, an electronic device is provided, comprising the organic electroluminescent device according to the second aspect.

[0016] The nitrogen-containing compound provided by the present application is composed of triazine, carbazole and triphenylsilyl, wherein the 4th position of carbazole is connected to the triphenylsilyl, and the 9th position is connected to the triazine. This specific connection mode can improve the steric hindrance of the compound structure and can improve the film-forming property of the material. When the nitrogen-containing compound of the present application is used as the main material of the organic light-emitting layer in the organic electroluminescent device, the carrier balance in the organic light-emitting layer can be improved, the carrier recombination area can be widened, the exciton generation and utilization efficiency can be improved, and the luminous efficiency and life of the device can be improved.

[0017] Other features and advantages of the present application will be described in detail in the subsequent specific implementation section. BRIEF DESCRIPTION OF THE DRAWINGS

[0018] 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.

[0019] Figure 1 It is a schematic structural diagram of an organic electroluminescent device of the present application.

[0020] Figure 2 It is a structural schematic diagram of an electronic device of the present application.

[0021] Reference numerals

[0022] 100, anode 200, cathode 300, functional layer 310, hole injection layer

[0023] 320, hole transport layer 330, electron blocking layer 340, organic light emitting layer 350, electron transport layer

[0024] 360. Electron injection layer 400. Electronic device DETAILED DESCRIPTION

[0025] In view of the above-mentioned problems existing in the prior art, the purpose of the present application is to provide a nitrogen-containing compound and an organic electroluminescent device and an electronic device comprising the nitrogen-containing compound, wherein the nitrogen-containing 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.

[0026] In a first aspect of the present application, a nitrogen-containing compound is provided, wherein the nitrogen-containing compound has a structure as shown in Formula 1:

[0027]

[0028] Wherein, D represents deuterium;

[0029] n, m and p are the same or different and are independently selected from 0, 1, 2, 3 or 4;

[0030] q is selected from 0, 1, 2, 3, 4, 5, 6 or 7;

[0031] L is selected from a single bond, phenylene or deuterium-substituted phenylene;

[0032] 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, and a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms;

[0033] 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;

[0034] The substituents in L1, L2, 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 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms, a heteroaryl group having 3 to 20 carbon atoms, a deuterated aryl group having 6 to 20 carbon atoms, and a halogenated aryl group having 6 to 20 carbon atoms.

[0035] 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.

[0036] 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 having a substituent Rc or an unsubstituted aryl. The above-mentioned substituent, i.e., Rc, can be, for example, deuterium, cyano, halogen group, alkyl, cycloalkyl, aryl, heteroaryl, deuterated aryl, halogenated aryl, etc. The number of substitutions can be 1 or more.

[0037] In the present application, "plurality" means more than 2, for example, 2, 3, 4, 5, 6, etc.

[0038] In the present application, the number of carbon atoms of a substituted or unsubstituted functional group refers to the total number of carbon atoms. For example, if L1 is a substituted arylene group having 12 carbon atoms, the total number of carbon atoms of the arylene group and the substituents thereon is 12.

[0039] 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 a carbon-carbon bond, a monocyclic aryl and a condensed ring aryl connected by a carbon-carbon bond, and two or more condensed ring aryl groups connected by a carbon-carbon bond. That is, unless otherwise indicated, two or more aromatic groups connected by a carbon-carbon bond can also be regarded as aryl of the present application. Among them, condensed ring aryl can, for example, include a dicyclic condensed aryl (e.g., naphthyl), a tricyclic condensed aryl (e.g., phenanthrenyl, fluorenyl, anthracenyl), etc. Aryl does not contain heteroatoms such as B, N, O, S, P, Se, and Si. Examples of aryl groups may include, but are not limited to, phenyl, naphthyl, fluorenyl, anthracenyl, phenanthrenyl, biphenyl, terphenyl, triphenylene, peryl, benzo[9,10]phenanthrenyl, pyrenyl, benzofluoranthenyl, In the present application, the arylene group refers to a divalent group formed by further losing a hydrogen atom from an aryl group.

[0040] In the present application, terphenyl includes

[0041] 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.

[0042] 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 20 carbon atoms, in other embodiments, the substituted or unsubstituted aryl group is a substituted or unsubstituted aryl group having 6 to 18 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.

[0043] In the present application, the aryl group as a substituent of L1, L2, Ar1 and Ar2 is exemplified but not limited to phenyl and the like.

[0044] 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 connected 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.

[0045] 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.

[0046] 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, cyano groups, 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.

[0047] 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.

[0048] In the present application, the halogen group may be, for example, fluorine, chlorine, bromine, or iodine.

[0049] In the present application, specific examples of the haloalkyl group include, but are not limited to, trifluoromethyl.

[0050] In the present application, specific examples of deuterated alkyl groups include, but are not limited to, trideuterated methyl groups.

[0051] In the present application, a deuterated aryl group refers to an aryl group containing at least one deuterium substituent. Specific examples of the deuterated aryl group include, but are not limited to, pentadeuterated phenyl and pentadeuterated biphenyl.

[0052] 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.

[0053] 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).

[0054]

[0055] 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).

[0056]

[0057] In some embodiments of the present application, the nitrogen-containing compound is selected from the structure shown in Formula A or Formula B:

[0058]

[0059] In formula A and formula B, D represents deuterium;

[0060] t, n, m and p are the same or different and are independently selected from 0, 1, 2, 3 or 4;

[0061] q is selected from 0, 1, 2, 3, 4, 5, 6 or 7;

[0062] 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, and a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms;

[0063] 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;

[0064] The substituents in L1, L2, 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 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms, a heteroaryl group having 3 to 20 carbon atoms, a deuterated aryl group having 6 to 20 carbon atoms, and a halogenated aryl group having 6 to 20 carbon atoms.

[0065] In some embodiments of the present application, L is selected from a single bond or the following groups:

[0066]

[0067] 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 12 carbon atoms, and a substituted or unsubstituted heteroarylene group having 12 to 18 carbon atoms.

[0068] 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.

[0069] 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, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenylene group, or a substituted or unsubstituted carbazolylene group.

[0070] 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.

[0071] In other 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:

[0072]

[0073] Specifically, L1 and L2 are the same or different and are independently selected from a single bond or the following groups:

[0074]

[0075] 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 20 carbon atoms, or a substituted or unsubstituted heteroaryl group having 12 to 20 carbon atoms.

[0076] 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.

[0077] 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 phenanthrenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl.

[0078] 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.

[0079] In some embodiments of the present application, Ar1 and Ar2 are the same or different and are independently selected from the group consisting of the following groups:

[0080]

[0081] Specifically, Ar1 and Ar2 are the same or different and are independently selected from the group consisting of the following groups:

[0082]

[0083]

[0084] In some embodiments of the present application, The same or different, are independently selected from the following groups:

[0085]

[0086] Specifically, The same or different, are independently selected from the following groups:

[0087]

[0088]

[0089] In some embodiments of the present application, in Formula 1 Selected from the group consisting of:

[0090]

[0091]

[0092] Specifically, in Equation 1 Selected from the group consisting of:

[0093]

[0094]

[0095]

[0096]

[0097] In some embodiments of the present application, n, m and p are the same and are selected from 0 or 4 at the same time.

[0098] In some embodiments of the present application, q is selected from 0 or 7.

[0099] In some embodiments of the present application, the nitrogen-containing compound is selected from the group consisting of the following compounds:

[0100]

[0101]

[0102]

[0103]

[0104]

[0105]

[0106]

[0107] In a second aspect, the present application provides an organic electroluminescent device, comprising an anode, a cathode, and a functional layer disposed between the anode and the cathode; wherein the functional layer comprises the nitrogen-containing compound described in the first aspect of the present application.

[0108] The nitrogen-containing compound provided in the present application can be used to form at least one organic film layer in the functional layer to improve the luminous efficiency and lifespan of the organic electroluminescent device.

[0109] Optionally, the functional layer includes an organic light-emitting layer, and the organic light-emitting layer includes the nitrogen-containing compound. The organic light-emitting layer can be composed of the organic compound provided in the present application, or can be composed of the nitrogen-containing compound provided in the present application and other materials.

[0110] Optionally, the functional layer further includes a hole transport layer, and the hole transport layer is located between the anode and the organic light-emitting layer.

[0111] According to a specific embodiment, the organic electroluminescent device is as follows Figure 1 As shown, the organic electroluminescent device may include an anode 100, a hole injection layer 310, a hole transport layer 320, an electron blocking layer 330, an organic light emitting layer 340, an electron transport layer 350, an electron injection layer 360 and a cathode 200 which are stacked in sequence.

[0112] Optionally, the anode 100 includes the following anode materials, which are preferably materials 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.

[0113] In the present application, the hole transport layer may include one or more hole transport materials, and the hole transport layer material may be selected from carbazole polymers, carbazole-linked triarylamine compounds or other types of compounds. In one embodiment of the present application, the hole transport layer 320 may be composed of HT-1.

[0114] Optionally, the electron blocking 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 electron blocking layer 330 is composed of HT-2.

[0115] Optionally, the electron blocking layer is also referred to as a hole buffer layer, a hole adjustment layer, a hole auxiliary layer, a luminescence adjustment layer, a luminescence auxiliary layer or a second hole transport layer.

[0116] 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 limitation on this. The material of the hole injection layer 310 may be selected from the following compounds or any combination thereof;

[0117]

[0118] In one embodiment of the present application, the hole injection layer 310 is composed of PD-1 and HT-1.

[0119] 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 the holes injected into the organic light-emitting layer 330 and the electrons injected into the organic light-emitting layer 340 may be recombined in the organic light-emitting layer 340 to form excitons, and the excitons transfer energy to the host material, and the host material transfers energy to the guest material, thereby enabling the guest material to emit light.

[0120] The host material of the organic light-emitting layer 340 may include metal chelate compounds, bisphenylethylene derivatives, aromatic amine derivatives, dibenzofuran derivatives or other types of materials. Optionally, the host material includes the nitrogen-containing compound of the present application.

[0121] The guest material of the organic light-emitting layer 340 can be a compound having a condensed aromatic ring or a derivative thereof, a compound having a heteroaromatic ring or a derivative thereof, an aromatic amine derivative or other materials, and the present application does not impose any special restrictions on this. The guest material is also called a doping material or a dopant. According to the type of luminescence, it can be divided into a fluorescent dopant and a phosphorescent dopant.

[0122] In the present application, the dopant used in the organic light-emitting layer in the organic electroluminescent device is a phosphorescent dopant.

[0123] In one embodiment of the present application, the organic electroluminescent device is a blue organic electroluminescent device. In a more specific embodiment, the host material of the organic light-emitting layer 340 includes the nitrogen-containing compound of the present application and the compound BH-P, and the guest material is BD-01.

[0124] The electron transport layer 350 may be a single-layer structure or a multi-layer structure, and may include one or more electron transport materials, which may be selected from but not limited to ET-1, LiQ, benzimidazole derivatives, oxadiazole derivatives, quinoxaline derivatives or other electron transport materials.

[0125] In one embodiment of the present application, the electron transport layer 350 may be composed of ET-1 and LiQ.

[0126] In the present application, cathode 200 may include a cathode material, which is a material with a small work function that facilitates electron injection into the functional layer. Specific examples of cathode materials include, but are not limited to, metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead or their alloys; or multilayer materials such as LiF / Al, Liq / Al, LiO2 / Al, LiF / Ca, LiF / Al and BaF2 / Ca. Optionally, a metal electrode containing magnesium and silver is included as the cathode.

[0127] Optionally, an electron injection layer 350 may be provided between the cathode 200 and the electron transport layer 340 to enhance the ability to inject electrons into the electron transport layer 340. The electron injection layer 350 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 one embodiment of the present application, the electron injection layer 350 may include ytterbium (Yb).

[0128] In a third aspect, the present application provides an electronic device, comprising the organic electroluminescent device described in the second aspect of the present application.

[0129] According to one embodiment, Figure 2 As shown, the provided electronic device is an electronic device 400, which includes the above-mentioned organic electroluminescent device. The electronic device 400 can be, for example, a display device, a lighting device, an optical communication device, or other types of electronic devices, such as but not limited to a computer screen, a mobile phone screen, a television, an electronic paper, an emergency lighting lamp, an optical module, etc.

[0130] The synthesis method of the organic compound of the present application is specifically described below in conjunction with synthesis examples, but the present disclosure is not limited thereby.

[0131] Synthesis Example

[0132] Those skilled in the art will recognize that the chemical reactions described herein can be used to appropriately prepare many of the organic compounds of the present invention, and that other methods for preparing the compounds of the present invention are considered to be within the scope of the present invention. For example, the synthesis of the compounds not exemplified herein can be successfully accomplished by those skilled in the art by modification methods, such as appropriate protection of interfering groups, by utilizing other known reagents in addition to those described herein, or by making some conventional modifications to the reaction conditions. The compounds of the synthetic methods not mentioned in the present invention are all raw materials obtained through commercial channels.

[0133] Synthesis of intermediate a:

[0134]

[0135] Under nitrogen protection, 2-(triphenylsilyl)phenylboronic acid (20.0 g; 52.6 mmol), 1-bromo-2-nitrobenzene (11.7 g; 57.8 mmol), tetrakistriphenylphosphine palladium (1.2 g; 1.1 mmol), potassium carbonate (14.5 g; 105.2 mmol), tetrabutylammonium bromide (3.4 g; 10.5 mmol), toluene (160 mL), ethanol (40 mL) and deionized water (40 mL) were added to a round-bottom flask, the temperature was raised to 75° C. to 80° C., and the reaction was stirred for 48 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 mixed solvent of dichloromethane / n-heptane to obtain a white solid intermediate a0 (14.0 g; yield: 58%);

[0136] The intermediate b1 (14.0 g; 30.6 mmol), triphenylphosphine (20.1 g; 76.5 mmol), and o-dichlorobenzene (150 mL) were added to a round-bottom flask protected by nitrogen, and the temperature was raised to 175°C to 180°C under stirring, and the reaction was carried out for 72 hours; the reaction solution was cooled to room temperature, deionized water was added, and the liquids were 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 mixed solvent of dichloromethane / n-heptane to obtain a white solid intermediate a (8.2 g; yield: 63%).

[0137] Synthesis of intermediate b1:

[0138]

[0139] Under nitrogen protection, 4-(triphenylsilyl)phenylboronic acid (10.0 g; 26.3 mmol), 4-bromocarbazole (6.8 g; 27.6 mmol), tetrakistriphenylphosphine palladium (0.6 g; 0.5 mmol), potassium carbonate (7.3 g; 52.6 mmol), tetrabutylammonium bromide (1.7 g; 5.3 mmol), toluene (80 mL), ethanol (20 mL) and deionized water (20 mL) were added to a round-bottom flask, the temperature was raised to 75°C to 80°C, and the reaction was stirred 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 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 mixed solvent of dichloromethane / n-heptane to obtain a white solid intermediate b1 (9.4 g; yield: 71%)

[0140] Referring to the synthesis method of intermediate b1, reactant A in Table 1 below is used to replace 4-(triphenylsilyl)phenylboronic acid, and reactant B is used to replace 4-bromocarbazole to synthesize the intermediate shown in Table 1 below:

[0141] Table 1

[0142]

[0143] Synthesis of compound A1:

[0144]

[0145] Under nitrogen protection, intermediate a (5.0 g; 11.7 mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine (4.7 g; 17.6 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 (0.3 g; 14.1 mmol) was added, and the mixture was stirred and reacted at -5°C to 0°C for 1 hour, and then the reaction solution was heated 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 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 toluene / n-heptane as an eluent, and then recrystallized and purified using a toluene / n-heptane mixed solvent to obtain white crystalline compound A1 (5.3 g; yield: 69%)

[0146] Referring to the synthesis method of compound A1, the intermediate a is replaced by reactant C, and 2-chloro-4,6-diphenyl-1,3,5-triazine is replaced by reactant D to synthesize the compounds shown in Table 2 below:

[0147] Table 2

[0148]

[0149]

[0150]

[0151]

[0152] The mass spectrometry data of some compounds are shown in Table 3 below.

[0153] Table 3

[0154]

[0155]

[0156] The NMR data of some compounds are shown in Table 4 below

[0157] Table 4

[0158]

[0159] Preparation of blue organic electroluminescent devices

[0160] Example 1: Preparation of blue organic electroluminescent device

[0161] The device was prepared by the following process

[0162] When the thickness of ITO / Ag / ITO is On the experimental substrate, ultraviolet, ozone and O2:N2 plasma are used for surface treatment 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.

[0163] Compounds HT-1 and PD-1 were co-evaporated on the experimental substrate at an evaporation rate ratio of 98%:2% to form a film with a thickness of The hole injection layer is then deposited with compound HT-1 to form a hole injection layer with a thickness of hole transport layer.

[0164] Compound HT-2 is evaporated on the hole transport layer to form a layer with a thickness of electron blocking layer.

[0165] On the electron blocking layer, compound BH-P, compound A1, and BD-01 were co-evaporated at an evaporation rate ratio of 50%:50%:10% to form a layer with a thickness of of an organic light-emitting layer.

[0166] On the organic light-emitting layer, compound ET-1 and LiQ were co-evaporated at an evaporation rate ratio of 50%:50% to form a layer with a thickness of electron transport layer.

[0167] Yb is evaporated on the electron transport layer to form a layer with a thickness of Then, magnesium (Mg) and silver (Ag) are co-evaporated at an evaporation rate ratio of 10%:90% on the electron injection layer to form a layer with a thickness of cathode.

[0168] Compound CP-1 is evaporated on the cathode to form a layer with a thickness of An organic covering layer is formed, thereby completing the preparation of a blue organic electroluminescent device.

[0169] Embodiment 2~embodiment 24:

[0170] An organic electroluminescent device was prepared by the same method as in Example 1, except that the compound A1 in Example 1 was replaced by the compound X in Table 6 when preparing the organic light-emitting layer.

[0171] Comparative Example 1 to Comparative Example 3:

[0172] An organic electroluminescent device was prepared in the same manner as in Example 1, except that Compound 1, Compound 2 and Compound 3 in Table 6 were used instead of Compound A1 in Example 1 when preparing the organic light-emitting layer.

[0173] Among them, when preparing the devices of the above embodiments and comparative examples, the structures of the compounds used are listed in the following Table 5:

[0174] Table 5

[0175]

[0176] The performance of the blue organic electroluminescent devices prepared in Examples 1 to 24 and Comparative Examples 1 to 3 was tested, specifically, the IVL and T90 device lifespans were tested under a brightness of 1000 nit. The test results are shown in Table 6 below:

[0177] Table 6

[0178]

[0179]

[0180] As can be seen from Table 6 above, when the compounds of the present application are used as the main material of the organic light-emitting layer of a blue organic electroluminescent device, the device performance can be greatly improved. Specifically, compared with the organic electroluminescent devices of Comparative Examples 1 to 3, the efficiency of the organic electroluminescent devices of Examples 1 to 24 is improved by at least 10.6%, and the lifespan T90 is improved by at least 13.0%.

[0181] Compared with Comparative Examples 1 to 3, the nitrogen-containing compound of the present application is connected to a triphenylsilyl group at the 4th position of carbazole, and such a connection can improve the steric hindrance of the compound, improve the film-forming property of the material, and make the material have higher efficiency and life. In particular, when the triphenylsilyl group and carbazole are not connected by a single bond, the device performance is better.

[0182] 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. Nitrogen compounds, It is characterized in that The compound has a structure as shown in Formula 1: Wherein, D represents deuterium; n, m and p are the same or different and are independently selected from 0, 1, 2, 3 or 4; q is selected from 0, 1, 2, 3, 4, 5, 6 or 7; L is selected from a single bond, phenylene or deuterium-substituted phenylene; 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, and a substituted or unsubstituted heteroarylene group having 3 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, 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 heteroaryl group having 3 to 20 carbon atoms, a deuterated aryl group having 6 to 20 carbon atoms, and a halogenated aryl group having 6 to 20 carbon atoms.

2. The nitrogen-containing compound according to claim 1, It is characterized in that L is selected from a single bond or the following group:

3. The nitrogen-containing 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, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothienyl group, and a substituted or unsubstituted carbazolyl group; Optionally, 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 nitrogen-containing 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 or the following groups: Optionally, L 1 and L 2 are the same or different, and are independently selected from a single bond or the following groups:

5. The nitrogen-containing 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 phenanthryl, substituted or unsubstituted terphenyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl; Optionally, 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 nitrogen-containing compound according to claim 1, It is characterized in that Ar 1 and Ar 2 The same or different, are independently selected from the following groups: Optionally, Ar 1 and Ar 2 The same or different, are independently selected from the following groups:

7. The nitrogen-containing compound according to claim 1, It is characterized in that The same or different, are independently selected from the following groups: Optionally, The same or different, are independently selected from the following groups:

8. The nitrogen-containing compound according to claim 1, It is characterized in that In formula 1 Selected from the group consisting of: Optionally, in Formula 1 Selected from the group consisting of:

9. The nitrogen-containing compound according to claim 1, It is characterized in that n, m and p are the same and are selected from 0 or 4 at the same time.

10. The nitrogen-containing compound according to claim 1, It is characterized in that q is selected from 0 or 7.

11. The nitrogen-containing compound according to claim 1, It is characterized in that The nitrogen-containing compound is selected from the group consisting of the following compounds:

12. 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 nitrogen-containing compound according to any one of claims 1 to 11; Optionally, the functional layer comprises an organic light-emitting layer, and the organic light-emitting layer comprises the nitrogen-containing compound according to any one of claims 1 to 11.

13. Electronic devices, It is characterized in that The organic electroluminescent device according to claim 12.

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