Nitrogen-containing compounds, electronic components and electronic devices

Abstract

The present application relates to the technical field of organic materials, and provides a nitrogen-containing compound, an electronic component and an electronic device. The nitrogen-containing compound has a structure as shown in Chemical Formula I, wherein Ar1 and Ar2 are each independently selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, and L is selected from a single bond, a substituted or unsubstituted arylene group having 6 to 20 carbon atoms. The nitrogen-containing compound can improve the performance of electronic components. #imgabs0#

Description

Technical Field

[0001] The present application belongs to the technical field of organic materials, and in particular relates to a nitrogen-containing compound, an electronic component and an electronic device. Background Art

[0002] Organic light-emitting diode (OLED) is abbreviated as OLED. Its principle is that when an electric field is applied between the positive and negative electrodes, the holes on the anode side and the electrons on the cathode side will move to the light-emitting layer, where they will combine to form excitons. The excitons will release energy outward in an excited state, and the process of releasing energy from the excited state to the ground state will emit light outward. Since the American Kodak Company reported the electroluminescence of organic molecules in 1987 and the University of Cambridge in the UK reported the electroluminescence of polymers in 1990, countries around the world have carried out research and development. Organic electroluminescent materials have the advantages of simple structure, high yield, low cost, active luminescence, fast response speed, high resolution, etc., and have the properties of low driving voltage, all solid state, non-vacuum, anti-vibration, and low temperature resistance (-40℃). It is considered to be a new technology that is most likely to replace liquid crystal displays in the future, and has attracted great attention.

[0003] Currently, OLED display technology has been applied in smart phones, tablets and other fields, and has further expanded to large-size application fields such as televisions. However, compared with the actual product application requirements, the main problems of existing organic electroluminescent devices are lifespan and efficiency. With the large-area display, the driving voltage also increases, and the luminous efficiency and lifespan also need to be improved. Therefore, it is necessary to continue to develop new organic electroluminescent materials to further improve the performance of organic electroluminescent devices. In order to produce high-performance OLED light-emitting devices, various organic functional materials are required to have good optoelectronic properties. Summary of the invention

[0004] The purpose of the present application is to provide a nitrogen-containing compound and an electronic component and an electronic device containing the same. The nitrogen-containing compound is used in the electronic component to improve the performance of the electronic component.

[0005] According to the first aspect of the present application, a nitrogen-containing compound is provided, having a structure represented by chemical formula I:

[0006]

[0007] wherein Ar1 and Ar2 are the same or different and are independently selected from substituted or unsubstituted aryl groups having 6 to 30 carbon atoms and substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms; L is selected from a single bond and a substituted or unsubstituted arylene group having 6 to 20 carbon atoms;

[0008] 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 10 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, a trialkylsilyl group having 3 to 12 carbon atoms, an aryl group having 6 to 15 carbon atoms, and a heteroaryl group having 5 to 12 carbon atoms; optionally, any two adjacent substituents form a ring;

[0009] The substituents in L 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 haloalkyl group having 1 to 5 carbon atoms, a cycloalkyl group having 5 to 8 carbon atoms, a trialkylsilyl group having 3 to 7 carbon atoms, and a phenyl group.

[0010] According to a second aspect of the present application, an electronic component is provided, comprising an anode and a cathode disposed opposite to each other, and a functional layer disposed between the anode and the cathode; the functional layer comprises the above-mentioned nitrogen-containing compound.

[0011] According to a third aspect of the present application, an electronic device is provided, comprising the above-mentioned electronic component.

[0012] In the nitrogen-containing compound provided in the present application, the oxygen-containing heteroanthene spirobenzanthracene group is used as the parent core, and the 4th position of the oxygen heteroanthene part is combined with the triarylamine structure, which can promote the torsion of the entire molecular structure. On the one hand, it can fully utilize the hole transport characteristics of the triarylamine structure to improve the hole mobility, and on the other hand, it makes the entire molecular structure have a higher stability. For example, the application of nitrogen-containing compounds to organic electroluminescent devices can significantly improve the luminous efficiency and service life of the device.

[0013] Other features and advantages of the present application will be described in detail in the subsequent detailed description. BRIEF DESCRIPTION OF THE DRAWINGS

[0014] Figure 1 It is a schematic diagram of the structure of an organic electroluminescent device according to one embodiment of the present application.

[0015] Figure 2 It is a schematic structural diagram of a first electronic device according to an embodiment of the present application.

[0016] Figure 3 It is a schematic structural diagram of a photoelectric conversion device according to one embodiment of the present application.

[0017] Figure 4 It is a schematic structural diagram of a second electronic device according to an embodiment of the present application.

[0018] Description of Reference Numerals

[0019] 100, anode; 200, cathode; 300, functional layer; 310, hole injection layer; 320, hole transport layer; 321, first hole transport layer; 322, second hole transport layer; 330, organic light-emitting layer; 340, electron transport layer; 350, electron injection layer; 360, photoelectric conversion layer; 400, first electronic device; 500, second electronic device. DETAILED DESCRIPTION

[0020] Example embodiments will now be described more fully with reference to the accompanying drawings. However, example embodiments can be implemented in a variety of forms and should not be construed as limited to the examples set forth herein; rather, these embodiments are provided so that the present application will be more comprehensive and complete and the concepts of the example embodiments are fully conveyed to those skilled in the art. The described features, structures, or characteristics may be combined in any suitable manner in one or more embodiments. In the following description, many specific details are provided to provide a full understanding of the embodiments of the present application.

[0021] In this application, the descriptions "each... is independently selected from" and "... are independently selected from" and "... are independently selected from" are interchangeable and should be understood in a broad sense, which can mean that in different groups, the specific options expressed by the same symbols do not affect each other, or that in the same group, the specific options expressed by the same symbols do not affect each other. For example, Wherein, each q is independently selected from 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.

[0022] In the present application, the terms "optionally" and "optionally" mean that the event or environment described later may but need not occur, and the description includes occasions where the event or environment occurs or does not occur. For example, "optionally, any two adjacent substituents form a ring" means that the two substituents may form a ring but do not have to form a ring, including: the situation where the two adjacent substituents form a ring and the situation where the two adjacent substituents do not form a ring.

[0023] In the present application, the term "substituted or unsubstituted" means that the functional group described after the term may or may not have a substituent (hereinafter, for the convenience of description, the substituent is collectively referred to as R c For example, "substituted or unsubstituted aryl" refers to a substituted cThe above-mentioned substituents, namely R c , for example, it can be deuterium, a halogen group, a cyano group, a heteroaryl group, an aryl group, a deuterated aryl group, a trialkylsilyl group, an alkyl group, a halogenated alkyl group, a cycloalkyl group, etc. "Two adjacent substituents" include two substituents R connected to the same atom in the functional group. c , and the two adjacent atoms in the functional group each have a substituent R c When two substituents R are attached to the same atom c When the two substituents R c can exist independently or be connected to each other to form a ring with the atom, for example, to form a 5-13-membered saturated or unsaturated ring; when the two adjacent atoms have substituents R c When the two substituents R c It may exist independently or be fused to form a ring with the functional group to which it is connected.

[0024] 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 Ar is selected from a substituted aryl group having 12 carbon atoms, the total number of carbon atoms of the aryl group and the substituents thereon is 12.

[0025] 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. Among them, condensed ring aryl can include, for example, a bicyclic 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. It should be noted that biphenyl and terphenyl. Examples of aryl groups may include, but are not limited to, phenyl, naphthyl, fluorenyl, anthracenyl, phenanthrenyl, biphenyl, terphenyl, benzo[9,10]phenanthrenyl, pyrenyl, benzofluoranthenyl, Ji et al.

[0026] In the present application, the substituted aryl group may be one or more hydrogen atoms in the aryl group replaced by groups such as deuterium, halogen groups, cyano groups, aryl groups, heteroaryl groups, trialkylsilyl groups, alkyl groups, cycloalkyl groups, etc. Specific examples of heteroaryl substituted aryl groups include, but are not limited to, dibenzofuranyl substituted phenyl groups, dibenzothiophenyl substituted phenyl groups, pyridyl substituted phenyl groups, etc. It should be understood that the number of carbon atoms in the substituted aryl group refers to the total number of carbon atoms in the aryl group and the substituents on the aryl group, for example, a substituted aryl group with 18 carbon atoms refers to a total number of carbon atoms in the aryl group and the substituent groups of 18. In the present application, the fluorenyl group may be substituted, and two substituents may be combined with each other to form a spiro structure, and specific examples include, but are not limited to, the following structures:

[0027]

[0028] in, It can be understood that the two substituents in the fluorenyl group form a 13-membered unsaturated ring; It can be understood that the two substituents in the fluorenyl group form a 5-membered saturated ring.

[0029] In the present application, heteroaryl refers to a monovalent aromatic ring or a derivative thereof containing at least one heteroatom in the ring, and the heteroatom may be at least one 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 benzothiazolyl group, a phenothiazinyl group, a silafluorenyl group, a dibenzofuranyl group, and an N-phenylcarbazolyl group, an N-pyridylcarbazolyl group, an N-methylcarbazolyl group, and the like, without being limited thereto. Among them, thienyl, furanyl, phenanthroline, etc. are heteroaryl groups of single aromatic ring system type, N-phenylcarbazolyl, N-pyridyl are heteroaryl groups of polycyclic system type connected by carbon-carbon bond conjugation. In this application, the heteroaryl group involved refers to a divalent group formed by further losing one or more hydrogen atoms of the heteroaryl group.

[0030] In the present application, the substituted heteroaryl group may be a heteroaryl group in which one or more hydrogen atoms are substituted by groups such as deuterium, a halogen group, a cyano group, an aryl group, a heteroaryl group, a trialkylsilyl group, an alkyl group, a cycloalkyl group, etc. Specific examples of aryl-substituted heteroaryl groups include, but are not limited to, phenyl-substituted dibenzofuranyl, phenyl-substituted dibenzothienyl, phenyl-substituted pyridyl, 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.

[0031] In this application, an unpositioned connecting bond refers to a single bond extending from the ring system. It means that one end of the connecting bond can be connected to any position in the ring system that the bond passes through, and the other end is connected to the rest of the compound molecule.

[0032] For example, as shown in the following formula (f), the naphthyl group represented by formula (f) is connected to other positions of the molecule through two non-positional connecting bonds that penetrate the bicyclic ring, and its meaning includes any possible connection method shown in formulas (f-1) to (f-10).

[0033]

[0034] For another example, as shown in the following formula (X'), the phenanthryl group 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).

[0035]

[0036] In the present application, the alkyl group having 1 to 10 carbon atoms may include a linear alkyl group having 1 to 10 carbon atoms and a branched alkyl group having 3 to 10 carbon atoms, and the carbon atoms may be 1, 2, 3, 4, 5, 6, 7, 8, 9, 10. 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, cyclopentyl, n-hexyl, heptyl, n-octyl, 2-ethylhexyl, nonyl, decyl, 3,7-dimethyloctyl, and the like.

[0037] In the present application, the halogen group may include fluorine, iodine, bromine, chlorine, and the like.

[0038] In the present application, the carbon number of the aryl group as a substituent can be 6 to 15, and the specific carbon number is 6, 10, 12, 13, 14, etc. Specific examples of the aryl group as a substituent include, but are not limited to, phenyl, naphthyl, biphenyl, fluorenyl, phenanthrenyl, anthracenyl, etc.

[0039] In the present application, the carbon number of the heteroaryl group as a substituent can be 5 to 12, and specific examples of the carbon number are 5, 8, 9, 10, 12, etc. Specific examples of the heteroaryl group as a substituent include, but are not limited to, pyridyl, quinolyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, etc.

[0040] In the present application, the number of carbon atoms of the trialkylsilyl group as a substituent can be 3-12, 3-6, 3-7, etc., for example, 3, 6, 7, etc. Specific examples include but are not limited to trimethylsilyl, ethyldimethylsilyl, triethylsilyl, etc.

[0041] In the present application, the number of carbon atoms of the cycloalkyl group as a substituent may be 3 to 10, preferably 5 to 8, and specific examples include, but are not limited to, cyclopentyl, cyclohexyl, adamantyl, and the like.

[0042] In the present application, the halogenated alkyl group may be, for example, a trifluoromethyl group, and the deuterated alkyl group may be, for example, a trideuterated methyl group.

[0043] The present application provides a nitrogen-containing compound having a structure as shown in Chemical Formula I:

[0044]

[0045] wherein 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;

[0046] L is selected from a single bond, a substituted or unsubstituted arylene group having 6 to 20 carbon atoms;

[0047] 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 10 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, a trialkylsilyl group having 3 to 12 carbon atoms, an aryl group having 6 to 15 carbon atoms, and a heteroaryl group having 5 to 12 carbon atoms; optionally, any two adjacent substituents form a ring;

[0048] The substituents in L 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 haloalkyl group having 1 to 5 carbon atoms, a cycloalkyl group having 5 to 8 carbon atoms, a trialkylsilyl group having 3 to 7 carbon atoms, and a phenyl group.

[0049] Optionally, L is selected from a single bond, a substituted or unsubstituted arylene group having 6 to 15 carbon atoms. Specifically, L is selected from a single bond, or a substituted or unsubstituted arylene group having 6, 7, 8, 9, 10, 11, 12, 13, 14, 15 carbon atoms.

[0050] Optionally, L is selected from a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted biphenylene group.

[0051] Optionally, the substituents in L are each independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, trifluoromethyl, phenyl, cyclopentyl, cyclohexyl, trimethylsilyl.

[0052] Optionally, L is selected from a single bond, a phenylene group, a biphenylene group, and a naphthylene group.

[0053] According to a specific embodiment, L is selected from a single bond or the following groups:

[0054]

[0055] According to a preferred embodiment, the nitrogen-containing compound has a structure as represented by Chemical Formula 1-I:

[0056] In this case, the nitrogen-containing compound is applied to an organic electroluminescent device to further improve the service life of the device.

[0057] Optionally, Ar1 and Ar2 are each independently selected from a substituted or unsubstituted aryl group having 6 to 25 carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 20 carbon atoms. Specifically, Ar1 and Ar2 are each independently selected from a substituted or unsubstituted aryl group having 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25 carbon atoms; or a substituted or unsubstituted heteroaryl group having 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20 carbon atoms.

[0058] Optionally, Ar1 and Ar2 are each independently selected from: substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted pyridyl, substituted or unsubstituted quinolyl.

[0059] Optionally, the substituents in Ar1 and Ar2 are each independently selected from deuterium, fluorine, cyano, alkyl with 1 to 4 carbon atoms, phenyl, naphthyl, phenanthrenyl, biphenyl, trifluoromethyl, cycloalkyl with 5 to 8 carbon atoms, trialkylsilyl with 3 to 7 carbon atoms, dibenzofuranyl, dibenzothienyl, carbazolyl, pyridyl; optionally, any two adjacent substituents form a saturated or unsaturated ring with 5 to 13 members. Optionally, any two adjacent substituents form a saturated or unsaturated ring with 5 to 13 members.

[0060] In one embodiment, Ar1 and Ar2 are each independently selected from a substituted or unsubstituted group Z, and the unsubstituted group Z is selected from the group consisting of the following groups:

[0061]

[0062] The substituted group Z has one or two or more substituents, each of which is independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, n-propyl, tert-butyl, phenyl, naphthyl, phenanthrenyl, carbazolyl, trifluoromethyl, trimethylsilyl, cyclopentyl, cyclohexyl, and pyridyl. When the number of substituents is greater than 1, each substituent may be the same or different.

[0063] According to a specific embodiment, Ar1 and Ar2 are each independently selected from the following groups:

[0064]

[0065]

[0066] Optionally, the nitrogen-containing compound is selected from the group consisting of the following compounds:

[0067]

[0068]

[0069]

[0070]

[0071]

[0072]

[0073]

[0074] The present application does not particularly limit the synthesis method of the nitrogen-containing compounds provided. Those skilled in the art can determine a suitable synthesis method based on the nitrogen-containing compounds of the present application in combination with the preparation methods provided in the synthesis examples. In other words, the synthesis examples of the present invention provide exemplary preparation methods of nitrogen-containing compounds, and the raw materials used can be obtained commercially or by methods well known in the art. Those skilled in the art can obtain all nitrogen-containing compounds provided in the present application according to these exemplary preparation methods, and all specific preparation methods for preparing the nitrogen-containing compounds will not be described in detail here, and those skilled in the art should not be understood as limiting the present application.

[0075] The second aspect of the present application provides an electronic component, comprising an anode, a cathode, and a functional layer disposed between the anode and the cathode, wherein the functional layer may contain the nitrogen-containing compound described in the first aspect of the present application. The nitrogen-containing compound provided in the present application may be used to form at least one organic film layer in the functional layer to improve the life and other characteristics of the electronic component.

[0076] Optionally, the functional layer includes a hole transport layer, and the hole transport layer includes the nitrogen-containing compound provided in the present application. The hole transport layer can be composed of the nitrogen-containing compound provided in the present application, or can be composed of the nitrogen-containing compound provided in the present application and other materials. The hole transport layer can be a single layer or a multilayer structure with more than two layers.

[0077] Optionally, the electronic component is an organic electroluminescent device or a photoelectric conversion device, wherein the organic electroluminescent device can be a green light device, a red light device or a blue light device, preferably a green light device or a red light device.

[0078] According to a specific embodiment, the electronic component is an organic electroluminescent device. Figure 1 As shown, the organic electroluminescent device may include an anode 100, a hole transport layer 320, an organic light emitting layer 330 as an energy conversion layer, an electron transport layer 340 and a cathode 200 which are stacked in sequence.

[0079] 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 are not limited thereto. Preferably, a transparent electrode comprising indium tin oxide (indium tin oxide) (ITO) as an anode is included.

[0080] Optionally, the hole transport layer 320 includes a first hole transport layer 321 and a second hole transport layer 322 which are stacked, and the first hole transport layer 321 is closer to the surface of the anode than the second hole transport layer 322 .

[0081] Optionally, the first hole transport layer 321 may be one or more hole transport materials, and the hole transport layer material is selected from carbazole polymer compounds and carbazole-linked triarylamine compounds, which are not specifically limited in the present application. For example, the first hole transport layer 321 may be composed of NPB, or HT-1 (the structure is shown below).

[0082] Optionally, the second hole transport layer 322 comprises the nitrogen-containing compound provided in the present application. Preferably, the second hole transport layer 322 is composed of the nitrogen-containing compound provided in the present application.

[0083] In the present application, the organic light-emitting layer 330 may include a host material and a guest material. The holes injected into the organic light-emitting layer 330 and the electrons injected into the organic light-emitting layer 330 may be compounded in the organic light-emitting layer 330 to form excitons. The excitons transfer energy to the host material, and the host material transfers energy to the guest material, thereby enabling the guest material to emit light. Both the host material and the guest material may be selected with reference to the prior art, and the present application is not particularly limited thereto. The host material may be selected from metal chelate compounds, bisphenylethylene derivatives, aromatic amine derivatives, dibenzofuran derivatives, and the like, for example, the compound CBP. The guest material may be selected from compounds having condensed aromatic rings or derivatives thereof, compounds having heteroaromatic rings or derivatives thereof, aromatic amine derivatives, and the like. For example, the guest material of the organic light-emitting layer 330 is Ir(piq)2(acac).

[0084] In the present application, the electron transport layer 340 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 but not limited to benzimidazole derivatives, oxadiazole derivatives, quinoxaline derivatives or other electron transport materials. For example, the electron transport layer 340 may be composed of TPBi and LiQ.

[0085] 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 alloys thereof; or multilayer materials such as LiF / Al, Liq / Al, LiO2 / Al, LiF / Ca, LiF / Al and BaF2 / Ca. It is preferred to include a metal electrode containing magnesium and silver as the cathode.

[0086] Alternatively, if Figure 1 As shown, a hole injection layer 310 may be provided between the anode 100 and the first hole transport layer 321 to enhance the ability to inject holes into the first hole transport layer 321. 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 thereon. For example, the hole injection layer 310 may be composed of F4-TCNQ.

[0087] Alternatively, if Figure 1 As shown, 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 alkali metals and organic matter. For example, the electron injection layer 350 may be composed of LiQ.

[0088] According to another embodiment, the electronic component may be a photoelectric conversion device. Figure 3 As shown, the photoelectric conversion device may include an anode 100 and a cathode 200 disposed opposite to each other, and a functional layer 300 disposed between the anode 100 and the cathode 200; the functional layer 300 includes the nitrogen-containing compound provided in the present application.

[0089] Alternatively, if Figure 3 As shown, the functional layer 300 includes a hole transport layer 320 , and the hole transport layer 320 includes the nitrogen-containing compound of the present application.

[0090] According to a specific implementation mode, Figure 3 As shown, the photoelectric conversion device may include an anode 100, a hole transport layer 320, a photoelectric conversion layer 360, an electron transport layer 340 and a cathode 200 which are stacked in sequence.

[0091] Optionally, the photoelectric conversion device may be a solar cell, in particular, an organic thin film solar cell. For example, in one embodiment of the present application, the solar cell may include an anode, a hole transport layer, a photoelectric conversion layer, an electron transport layer and a cathode stacked in sequence, wherein the hole transport layer contains the nitrogen-containing compound of the present application.

[0092] A third aspect of the present application provides an electronic device, comprising the electronic component described in the second aspect of the present application.

[0093] According to one embodiment, Figure 2 As shown, the electronic device is a first electronic device 400, and the first electronic device 400 includes the above-mentioned organic electroluminescent device. The first 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.

[0094] According to another embodiment, Figure 4 As shown, the electronic device is a second electronic device 500, and the second electronic device 500 includes the above-mentioned photoelectric conversion device. The second electronic device 500 can be, for example, a solar power generation device, a light detector, a fingerprint recognition device, an optical module, a CCD camera or other types of electronic devices.

[0095] The compounds whose synthesis methods are not mentioned in this application are all raw materials obtained through commercial channels.

[0096] The present application will be described in detail below in conjunction with synthesis examples and 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.

[0097] 1. Synthesis of Intermediate IX

[0098] The synthesis method of intermediate IX is described below using the synthesis of intermediate I-1.

[0099]

[0100] Under nitrogen protection, raw materials sub a-1 (50.00 g, 190.0 mmol), sub b-1 (18.58 g, 199.5 mmol), sodium tert-butoxide (36.52 g, 380.0 mmol) and 400 mL of toluene were added in sequence to a reaction bottle equipped with a mechanical stirrer, a thermometer and a condenser. The mixture was heated to reflux and water was separated for 1 h. The temperature was lowered to 70-80 ° C, X-Phos (0.54 g, 1.14 mmol) and Pd2(dba)3 (0.52 g, 0.57 mmol) were added, and the temperature was continued to rise to reflux for 2 h. The reaction solution was cooled to room temperature, 400 mL of water was added, stirred, allowed to stand, and separated. The aqueous phase was extracted once with 200 mL of toluene, separated, the organic phases were combined, washed twice with 400 mL of water, separated, 30 g of anhydrous sodium sulfate was added to the organic phase for drying, filtered, the organic phase was passed through a silica gel chromatography column, and rinsed with 300 mL of toluene. The organic phase was concentrated (-0.08 to -0.09 MPa, 55-65°C). When 120 mL of organic phase remained, the concentration was stopped, the temperature was lowered to room temperature, and the temperature was kept for 2 h. A large amount of solid precipitated and filtered to obtain intermediate I-1 (44.47 g, yield 85%).

[0101] The intermediate IX listed in Table 1 was synthesized by referring to the method of intermediate I-1, except that raw material sub aX was used instead of raw material sub a-1, and raw material sub bX was used instead of sub b-1. The main raw materials used and the structures and yields of the corresponding synthesized intermediate IX are shown in Table 1.

[0102] Table 1

[0103]

[0104]

[0105]

[0106] 2. Synthesis of intermediate II-X

[0107] The synthesis method of intermediate II-X is illustrated below using the synthesis of intermediate II-1.

[0108]

[0109] (1) Under nitrogen protection, raw material subc-1 (50.00 g, 207.0 mmol), raw material sub d-1 (36.78 g, 217.35 mmol), sodium tert-butoxide (39.8 g, 414.0 mol) and 400 mL of toluene were added in sequence to a reaction flask equipped with a mechanical stirrer, a thermometer and a condenser. The mixture was heated to reflux and water was separated for 1 h. The temperature was lowered to 70-80°C, X-Phos (0.59 g, 1.24 mmol) and Pd2(dba)3 (0.57 g, 0.62 mmol) were added, and the temperature was continued to rise to reflux for 2 h. The reaction solution was cooled to room temperature, 400 mL of water was added, stirred, allowed to stand, and separated. The aqueous phase was extracted once with 200 mL of toluene, separated, the organic phases were combined, washed twice with 400 mL of water, separated, 30 g of anhydrous sodium sulfate was added to the organic phase for drying, filtered, the organic phase was passed through a silica gel chromatography column, and rinsed with 300 mL of toluene. The organic phase was concentrated (-0.08 to -0.09 MPa, 55-65°C) to leave 120 mL, the concentration was stopped, the temperature was lowered to room temperature, and the temperature was kept for 2 h. A large amount of solid precipitated and was filtered to obtain intermediate II-A-1 (57.36 g, yield 84%).

[0110]

[0111] (2) After replacing the three-necked reaction flask equipped with mechanical stirring, thermometer and constant pressure dropping funnel with nitrogen, the intermediate II-A-1 (57.36, 174.0 mmol), diboric acid pinacol ester (53.02 g, 208.8 mmol), potassium acetate (34.15 g, 348.0 mmol) and 1,4-dioxane (450 mL) were added in sequence, stirring was started and the temperature was raised to 45-50°C, X-Phos (1.66 g, 3.48 mmol) and PdCl2(dppf) (1.27 g, 1.74 mmol) were added, and the temperature was continued to rise to 90-95°C and reacted for 2 h. The reaction solution was cooled to room temperature, 400 mL of dichloromethane and 300 mL of water were added, stirred, allowed to stand, and separated. The aqueous phase was extracted once with 200 mL of dichloromethane, separated, the organic phases were combined, washed twice with 300 mL of water, separated, 20.00 g of anhydrous sodium sulfate was added to the organic phase for drying, filtered, the organic phase was passed through a silica gel chromatography column, and rinsed with 300 mL of dichloromethane. The organic phase was concentrated (-0.08 to -0.09 MPa, 40-50°C) until 120 mL of organic phase remained, the concentration was stopped, 240 mL of anhydrous ethanol was added, stirred at room temperature for 2 h, filtered, and the filter cake was rinsed with anhydrous ethanol to obtain intermediate II-1 (60.09 g, yield 82%).

[0112] The intermediate II-X listed in Table 2 was synthesized by referring to the method of intermediate II-1, except that the raw material sub cX was used instead of the raw material sub c-1, and the raw material sub dX (including part of intermediate IX) was used instead of sub d-1. The main raw materials used and the structures and yields of the corresponding synthesized intermediates II-X are shown in Table 2.

[0113] Table 2

[0114]

[0115]

[0116] 3. Synthesis of Intermediate A1

[0117]

[0118] (1) Under nitrogen protection, raw material sub e (32.18 g, 113.64 mmol) and 240 mL of dry tetrahydrofuran were added to a reaction flask equipped with a mechanical stirrer, a thermometer, and a condenser in sequence, and the temperature was lowered to -80°C. A n-hexane solution of n-butyl lithium (2 mol / L, 73.87 mL) was slowly added dropwise. After the addition was completed, the temperature was kept at -80°C for 1 h, and the raw material sub f (34.39g, 125.0mmol) in tetrahydrofuran (70mL) solution, keep warm for 1h and then naturally raise the temperature. After the reaction is complete, 120g of 20wt% dilute hydrochloric acid is added dropwise, 300mL of dichloromethane is added to the reaction solution, stirred, allowed to stand, separated, the aqueous phase is extracted once with 100mL of dichloromethane, the organic phases are combined, washed with water until neutral (about 300mL / 2 times of water), 20g of anhydrous sodium sulfate is added to the organic phase, stirred and dried, filtered, the organic phase is concentrated (-0.08 to -0.09MPa, 40-50℃) to 100mL, the concentration is stopped, 200mL of anhydrous ethanol is added and the temperature is lowered to 15-20℃, a large amount of solid is precipitated, filtered, and the filter cake is rinsed with ethanol to obtain intermediate III-1 (40.86g, yield 75%).

[0119]

[0120] (2) Under nitrogen protection, intermediate III-1 (40.86 g, 85.26 mmol), 400 mL of glacial acetic acid and 5.50 g of 36.5 wt% concentrated hydrochloric acid were added in sequence to a reaction bottle equipped with a mechanical stirrer, a thermometer and a condenser. The temperature was raised to reflux and the reaction was kept at this temperature for 10 h. The temperature was lowered to 25° C., 250 mL of toluene and 500 mL of water were added, the mixture was stirred, allowed to stand, and the liquid was separated. The aqueous phase was extracted with 150 mL of toluene. The organic phases were combined, washed with water until neutral, dried with 30 g of anhydrous sodium sulfate, filtered, and the filtrate was passed through a (80-120) mesh silica gel column. The column liquid was concentrated (55-65° C., -0.09 to -0.08 MPa) until 120 mL remained. The concentration was stopped, 200 mL of petroleum ether was added, solid precipitated, filtered, and the filter cake was rinsed with petroleum ether to obtain intermediate A1 (33.43 g, yield 85%).

[0121] 4. Synthesis example

[0122] Synthesis Example 1: Synthesis of Compound 17

[0123]

[0124] Under nitrogen protection, intermediate A1 (50.0 g, 108.37 mmol), intermediate I-3 (30.91 g, 119.21 mmol), sodium tert-butoxide (20.83 g, 216.74 mol) and 400 mL of toluene were added in sequence to a reaction bottle equipped with a mechanical stirrer, a thermometer and a condenser. The mixture was heated to reflux, and water was separated for 1 h. The temperature was lowered to 70-80 ° C, X-Phos (0.31 g, 0.65 mmol) and Pd2(dba)3 (0.31 g, 0.33 mmol) were added, and the temperature was continued to rise to reflux for 2 h. The reaction solution was cooled to room temperature, 400 mL of water was added, stirred, allowed to stand, and separated. The aqueous phase was extracted once with 200 mL of toluene, separated, the organic phases were combined, washed twice with 400 mL of water, separated, 30 g of anhydrous sodium sulfate was added to the organic phase for drying, filtered, the organic phase was passed through a silica gel chromatography column, and eluted with 300 mL of toluene. The organic phase was concentrated (-0.08 to -0.09 MPa, 55-65°C). When 120 mL of organic phase remained, the concentration was stopped, the temperature was lowered to room temperature, and the temperature was kept for 2 h. A large amount of solid was precipitated, filtered, and compound 17 (60.32 g, yield 87%) was obtained; mass spectrum m / z=640.2[M+H] + . NMR of compound 17: 1 HNMR(300MHz, CDCl3)(δppm):8.51-8.50(d,1H), 8.06-8.03(m,2H), 7.98-7.93(m ,3H), 7.76-7.73(m,2H), 7.42-7.28(m,7H), 7.23-7.08(m,8H), 7.05-6.88(m,6H).

[0125] Synthesis example 2-22

[0126] The compounds listed in Table 3 were synthesized by referring to the method of compound 17, except that intermediate IX was used to replace intermediate I-3. The main raw materials used, the corresponding synthesized compounds, yields and mass spectrometry characterization results are shown in Table 3.

[0127] Table 3

[0128]

[0129]

[0130]

[0131]

[0132] Synthesis Example 23: Synthesis of Compound 112

[0133]

[0134] Under nitrogen protection, intermediate A1 (50.0 g, 108.37 mmol), intermediate II-3 (54.8 g, 130.04 mmol), TBAB (3.5 g, 10.84 mmol), potassium carbonate (29.96 g, 216.74 mmol) and 300 mL of toluene, 150 mL of ethanol, and 150 mL of water were added to a reaction bottle equipped with a mechanical stirrer, a thermometer, and a condenser. Stirring was started, the temperature was raised to 45-50 ° C, and dichlorodi-tert-butyl-(4-dimethylaminophenyl)phosphine palladium (II) (Pd132, 0.04 g, 0.06 mmol) was added. ), continue to heat to reflux, keep warm for 2h until the reaction is complete, cool the reaction solution to room temperature, add 300mL of water, stir, stand, separate, extract the aqueous phase with 150mL of toluene once, separate, combine the organic phases, wash twice with 300mL of water, separate, add 20g of anhydrous sodium sulfate to the organic phase, dry, filter, pass the organic phase through a silica gel chromatography column, rinse with 300mL of toluene, concentrate the organic phase (-0.08 to -0.09MPa, 55-65°C) to 120mL, stop concentrating, cool to room temperature, keep warm for 2h, a large amount of solid precipitates, filter, and obtain compound 112 (54.93g, yield 75%). Mass spectrum m / z=676.3[M+H] + . NMR of compound 112: 1H NMR (300MHz, CDCl3) (δppm): 8.72-8.69(d,1H), 8.37-8.32(m,4H), 8.21-8.17(m,2H), 7.98-7.93(m, 3H), 7.72-7.68(m,2H), 7.46-7.53(m,5H), 7.38-7.29(m,8H), 7.13-7.02(m,6H), 6.96-6.93(m,2H).

[0135] Synthesis Examples 24 to 32

[0136] The compounds shown in Table 4 were synthesized by referring to the method of compound 112, except that intermediate II-X was used to replace intermediate II-3. The main raw materials used, the corresponding synthesized compounds, yields and mass spectrometry characterization results are shown in Table 4.

[0137] Table 4

[0138]

[0139]

[0140] Preparation and evaluation of organic electroluminescent devices

[0141] Example 1

[0142] The organic electroluminescent device is prepared by the following process: The ITO substrate was cut into a size of 40 mm (length) × 40 mm (width) × 0.7 mm (thickness), and a photolithography process was used to prepare it into an experimental substrate with cathode, anode and insulating layer patterns. The surface was treated with ultraviolet ozone and O2:N2 plasma to increase the work function of the anode, and the surface of the ITO substrate was cleaned with an organic solvent to remove impurities and oil stains on the surface of the ITO substrate.

[0143] F4-TCNQ was vacuum evaporated on the experimental substrate (anode) to form a layer with a thickness of A hole injection layer (HIL) of 100 mm thick was formed, and HT-1 was vacuum-evaporated on the hole injection layer (HIL) to form a layer with a thickness of 100 mm. The first hole transport layer (HTL1) is formed by a plurality of holes.

[0144] Compound 17 is evaporated on the first hole transport layer (HTL1) to form a layer with a thickness of A second hole transport layer (HTL2) is formed.

[0145] On the second hole transport layer, CBP was used as the main body and Ir(piq)2(acac) was doped at the same time according to the film thickness ratio of 100:3 to form a layer with a thickness of of an organic light-emitting layer (EML).

[0146] BimiBphen and LiQ were mixed in a weight ratio of 1:1 and evaporated on the organic light-emitting layer (EML) to form LiQ is evaporated on the electron transport layer to form a layer with a thickness of The electron injection layer (EIL) of

[0147] Magnesium (Mg) and silver (Ag) are mixed at a deposition rate of 1:9 and vacuum deposited on the electron injection layer to form a layer with a thickness of In addition, a layer with a thickness of A cover layer (CPL) is formed by coating CP-1, thereby completing the manufacture of the organic light-emitting device.

[0148] Example 2-Example 33

[0149] An organic electroluminescent device was prepared in the same manner as in Example 1, except that the compound shown in Table 5 was used instead of Compound 17 when forming the second hole transport layer.

[0150] Comparative Example 1-Comparative Example 4

[0151] An organic electroluminescent device was manufactured by the same method as in Example 1, except that compound A, compound B, compound C, and compound D were used instead of compound 17 respectively when forming the second hole transport layer.

[0152] The main materials for preparing organic electroluminescent devices and the structural formulas of compounds A to D are as follows:

[0153]

[0154] The organic electroluminescent devices prepared in the above examples and comparative examples were charged at 10 mA / mm 2 The IVL performance of the device was analyzed under the conditions of 15mA / mm 2 The T95 life of the device was analyzed under the conditions of , and the test results are shown in Table 5.

[0155] Table 5

[0156]

[0157] Combined with the results in Table 5, it can be seen that the organic electroluminescent devices prepared in Examples 1-33 using the compounds of the present application as the second hole transport layer material are compared with the devices prepared in Comparative Examples 1-4 using compounds A, B, C and D respectively. The organic electroluminescent devices prepared in Examples 1-33 have a current efficiency (Cd / A) of at least 7.8%, an external quantum efficiency of at least 11.5%, and a lifespan of at least 15.6% while ensuring a lower driving voltage.

[0158] Those skilled in the art will appreciate that the above-mentioned embodiments are specific examples for implementing the present invention, and in actual applications, various changes may be made thereto in form and detail without departing from the spirit and scope of the present invention.

Claims

1. A nitrogen-containing compound having a structure represented by chemical formula I: in, Ar1 and Ar2 are each independently selected from a substituted or unsubstituted group Z, and the unsubstituted group Z is selected from the group consisting of the following groups: The substituted group Z has one or two or more substituents, each of which is independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, n-propyl, tert-butyl, phenyl, naphthyl, phenanthrenyl, carbazolyl, trifluoromethyl, trimethylsilyl, and pyridyl; L is selected from a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, and a substituted or unsubstituted biphenylene group; The substituents in L are each independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, trifluoromethyl, phenyl, and trimethylsilyl.

2. The nitrogen-containing compound according to claim 1, wherein The structure of the nitrogen-containing compound is shown in Chemical Formula 1-I:

3. The nitrogen-containing compound according to claim 1, wherein Ar1 and Ar2 are each independently selected from the following groups:

4. The nitrogen-containing compound according to claim 1, wherein The nitrogen-containing compound is selected from the group consisting of the following compounds:

5. An electronic component, 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 4.

6. The electronic component according to claim 5, wherein The electronic element is an organic electroluminescent device or a photoelectric conversion device.

7. The electronic component according to claim 5 or 6, wherein: The functional layer includes a hole transport layer, and the hole transport layer contains the nitrogen-containing compound.

8. An electronic device, characterized in that: The electronic component comprises the electronic component according to any one of claims 5 to 7.

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