Organic compound, organic electroluminescent device and electronic device

Abstract

The present application relates to an organic compound, an organic electroluminescent device and an electronic device. The organic compound of the present application has a structure as shown in Formula 1, and the organic compound is applied to an organic electroluminescent device to significantly improve the performance of the device.

Description

Technical Field

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

[0002] With the development of electronic technology and the progress of materials science, the research scope of electronic components for electroluminescence or photoelectric conversion is becoming more and more extensive. Among them, organic electroluminescent devices, also known as organic light-emitting diodes, refer to the phenomenon that organic light-emitting materials emit light under the action of an electric field and are excited by current. Such electronic components usually include a cathode and an anode arranged relatively to each other, and a functional layer arranged between the cathode and the anode. The functional layer is composed of multiple organic or inorganic film layers, and generally includes an energy conversion layer, a hole transport layer located between the energy conversion layer and the anode, and an electron transport layer located between the energy conversion layer and the cathode. Taking an organic electroluminescent device as an example, it generally includes an anode, a hole transport layer, an electroluminescent layer as an energy conversion layer, an electron transport layer, and a cathode arranged 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 to the electroluminescent layer, and the holes on the anode side also move to the light-emitting layer. The electrons and holes combine in the electroluminescent layer to form excitons, and the excitons are in an excited state and release energy outward, thereby causing the electroluminescent layer to emit light outward.

[0003] Organic charge transport materials are organic semiconductor materials that can achieve directional, orderly and controllable migration of carriers under the action of an electric field when carriers (electrons or holes) are injected, thereby achieving charge transport. This type of material requires excellent electron-donating properties, low ionization potential, high hole mobility, good solubility and amorphous film-forming properties, strong fluorescence properties and photostability. At present, the performance of triarylamine materials in hole transport materials is relatively excellent and is one of the research hotspots. Although the prior art discloses materials that can be used to prepare hole transport in organic electroluminescent devices, the existing triarylamine hole transport layer materials perform poorly in terms of voltage, luminous efficiency, power and life in the device. Therefore, it is still necessary to continue to develop new materials to further improve the performance of electronic components. Summary of the invention

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

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

[0006]

[0007] Wherein, L1 and L2 are the same or different and are independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, and a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms;

[0008] Ar1 and Ar2 are the same or different and are independently selected from a substituted or unsubstituted aryl group having 6 to 40 carbon atoms, or a substituted or unsubstituted heteroaryl group having 3 to 40 carbon atoms;

[0009] L3 is selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms;

[0010] Ar3 is selected from substituted or unsubstituted aromatic groups having 6 to 30 carbon atoms;

[0011] The substituents in L1, L2, L3, Ar1, Ar2 and Ar3 are the same or different and are independently selected from deuterium, halogen groups, cyano groups, alkyl groups with 1 to 10 carbon atoms, cycloalkyl groups with 3 to 20 carbon atoms, heteroaryl groups with 12 to 20 carbon atoms, aryl groups with 6 to 20 carbon atoms, deuterated aryl groups with 6 to 20 carbon atoms, halogenated aryl groups with 6 to 20 carbon atoms, trialkylsilyl groups with 3 to 12 carbon atoms, triarylsilyl groups with 18 to 24 carbon atoms, halogenated alkyl groups with 1 to 10 carbon atoms, and deuterated alkyl groups with 1 to 10 carbon atoms;

[0012] Optionally, in Ar1 and Ar2, any two adjacent substituents form a ring.

[0013] 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 organic compound.

[0014] According to a third aspect of the present application, an electronic device is provided, comprising the electronic component described in the second aspect.

[0015] The present application provides a compound with phenanthrene-substituted aniline as the core structure. The ortho position (2 position) of the amine group is connected to a phenanthrene group, which is a large conjugated rigid planar group. Such a connection can make the compound molecule have good ortho-position spatial conjugation effect and photoelectric stability. Further, an aryl group is connected to the 5th position of the aniline, so that the compound maintains the molecular energy level characteristics while enhancing the spatial effect, so that the molecule has a stable amorphous state and enhanced film-forming properties. When the compound of the present application is used as a hole auxiliary layer material in an organic electroluminescent device, the device can have improved luminous efficiency and life performance while maintaining a low driving voltage.

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

[0017] The accompanying drawings are used to provide further understanding of the present application and constitute a part of the specification. Together with the following specific embodiments, they are used to explain the present application, but do not constitute a limitation to the present application.

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

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

[0020] Reference numerals

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

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

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

[0024] Exemplary embodiments will now be described more fully with reference to the accompanying drawings. However, exemplary embodiments can be implemented in a variety of forms and should not be construed as being 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 exemplary embodiments will be 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.

[0025] In a first aspect, the present application provides an organic compound having a structure as shown in Formula 1:

[0026]

[0027] Wherein, L1 and L2 are the same or different and are independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, and a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms;

[0028] Ar1 and Ar2 are the same or different and are independently selected from a substituted or unsubstituted aryl group having 6 to 40 carbon atoms, or a substituted or unsubstituted heteroaryl group having 3 to 40 carbon atoms;

[0029] L3 is selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms;

[0030] Ar3 is selected from substituted or unsubstituted aromatic groups having 6 to 30 carbon atoms;

[0031] The substituents in L1, L2, L3, Ar1, Ar2 and Ar3 are the same or different and are independently selected from deuterium, halogen groups, cyano groups, alkyl groups with 1 to 10 carbon atoms, cycloalkyl groups with 3 to 20 carbon atoms, heteroaryl groups with 12 to 20 carbon atoms, aryl groups with 6 to 20 carbon atoms, deuterated aryl groups with 6 to 20 carbon atoms, halogenated aryl groups with 6 to 20 carbon atoms, trialkylsilyl groups with 3 to 12 carbon atoms, triarylsilyl groups with 18 to 24 carbon atoms, halogenated alkyl groups with 1 to 10 carbon atoms, and deuterated alkyl groups with 1 to 10 carbon atoms;

[0032] Optionally, in Ar1 and Ar2, any two adjacent substituents form a ring.

[0033] In the present application, the terms "optionally" and "optionally" mean that the event or environment described subsequently may occur but need not occur, and the description includes occasions where the event or environment occurs or does not occur. For example, "optionally, 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.

[0034] In the present application, in the phrase "any two adjacent substituents form a ring", "any adjacent" may include two substituents on the same atom, or one substituent on each of two adjacent atoms; when two substituents are on the same atom, the two substituents may form a saturated or unsaturated ring with the atom to which they are connected; when two adjacent atoms each have one substituent, the two substituents may be fused into a ring. For example, when Ar1 has two or more substituents, when any adjacent substituents form a ring, a saturated or unsaturated cyclic group is formed, such as a benzene ring, a naphthalene ring, a phenanthrene ring, an anthracene ring, a fluorene ring, a cyclopentane, a cyclohexane, adamantane, and the like.

[0035] In the present application, the fluorenyl group may be substituted by 1 or 2 substituents, wherein, when the fluorenyl group is substituted, it may be: etc., but not limited thereto.

[0036] In this application, the descriptions "each... is independently" and "... are independently" and "... are independently selected from" 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.

[0037] 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, a halogen group, a cyano group, an alkyl group, a cycloalkyl group, an aryl group, a heteroaryl group, a deuterated aryl group, a halogenated aryl group, a trialkylsilyl group, a triarylsilyl group, a halogenated alkyl group, a deuterated alkyl group, 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 carbon-carbon bond conjugation, a monocyclic aryl and a condensed ring aryl connected by carbon-carbon bond conjugation, and two or more condensed ring aryl groups connected by carbon-carbon bond conjugation. That is, unless otherwise specified, two or more aromatic groups connected by carbon-carbon bond conjugation can also be regarded as aryl of the present application. Wherein, condensed ring aryl can, for example, include bicyclic condensed aryl (e.g., naphthyl), tricyclic condensed aryl (e.g., phenanthrenyl, fluorenyl, anthracenyl), etc. Aryl does not contain heteroatoms such as B, N, O, S, P, Se, and Si. Examples of aryl groups may include, but are not limited to, phenyl, naphthyl, fluorenyl, anthracenyl, phenanthrenyl, biphenyl, terphenyl, 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 substituted aryl group may be one or more hydrogen atoms in the aryl group replaced by groups such as deuterium atoms, halogen groups, cyano groups, aryl groups, heteroaryl groups, alkyl groups, cycloalkyl 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 means that the total number of carbon atoms in the aryl group and the substituents is 18.

[0042] In the present application, heteroaryl refers to a monovalent aromatic ring or a derivative thereof containing 1, 2, 3, 4, 5, 6 or 7 heteroatoms in the ring, and the heteroatoms 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, and N-phenylcarbazolyl and N-pyridylcarbazolyl 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 a hydrogen atom of the heteroaryl group.

[0043] 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, alkyl groups, cycloalkyl 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.

[0044] In the present application, the number of carbon atoms of the substituted or unsubstituted aryl group can be 6 to 25, for example, the number of carbon atoms can be 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, or 25.

[0045] In the present application, specific examples of aryl as a substituent include, but are not limited to, phenyl, biphenyl, naphthyl, fluorenyl, phenanthrenyl, anthracenyl, base.

[0046] In the present application, the number of carbon atoms of the substituted or unsubstituted heteroaryl group can be 12 to 20, for example, the number of carbon atoms can be 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, or 20.

[0047] In the present application, specific examples of the heteroaryl group as a substituent include, but are not limited to, carbazolyl, dibenzofuranyl, and dibenzothiophenyl.

[0048] In this application, the non-localized connecting bond refers to the 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.

[0049] 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 mode shown in formula (f-1) to formula (f-10).

[0050]

[0051] 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 formula (X'-1) to formula (X'-4).

[0052]

[0053] 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, 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, n-octyl, 2-ethylhexyl, nonyl, decyl, 3,7-dimethyloctyl, and the like.

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

[0055] 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 and cyclohexyl.

[0056] In the present application, specific examples of the deuterated aryl group include, but are not limited to, pentadeuterated phenyl group.

[0057] In some embodiments of the present application, the organic compound is selected from the compound represented by formula A, formula B or formula C:

[0058]

[0059] 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 15 carbon atoms, and a substituted or unsubstituted heteroarylene group having 12 to 20 carbon atoms.

[0060] 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, or a phenyl group.

[0061] 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 carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, and a substituted or unsubstituted dibenzothiophenylene group.

[0062] 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 or phenyl.

[0063] 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 group V, wherein the unsubstituted group V is selected from the group consisting of the following groups:

[0064]

[0065] The substituted group V has one or more substituents, and the substituents are independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl or phenyl. When the number of the substituents is greater than 1, the substituents are the same or different.

[0066] Optionally, L1 and L2 are the same or different and are independently selected from a single bond or the following groups:

[0067]

[0068] Specifically, L1 and L2 are the same or different and are independently selected from a single bond or the following groups:

[0069]

[0070] In some embodiments of the present application, Ar1 and Ar2 are the same or different and are independently selected from substituted or unsubstituted aryl groups having 6 to 25 carbon atoms and substituted or unsubstituted heteroaryl groups having 12 to 20 carbon atoms;

[0071] 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;

[0072] Optionally, in Ar1 and Ar2, any two adjacent substituents form a fluorene ring

[0073] In other embodiments of the present application, Ar1 and Ar2 are the same or different, and are independently selected from substituted or unsubstituted terphenyl, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted triphenylene, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted spirobifluorenyl;

[0074] 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.

[0075] In some embodiments of the present application, Ar1 and Ar2 are the same or different, and are independently selected from substituted or unsubstituted groups G, wherein the unsubstituted group G is selected from the group consisting of the following groups:

[0076]

[0077] The substituted group G has one or more substituents, and the substituents in the substituted group G are independently selected from the group consisting of deuterium, fluorine, cyano, phenyl, methyl, ethyl, n-propyl, isopropyl, tert-butyl, phenyl, and pentadeuterated phenyl, and when the number of substituents in the group G is greater than 1, the substituents are the same or different.

[0078] Optionally, Ar1 and Ar2 are the same or different and are independently selected from the following groups:

[0079]

[0080] Specifically, Ar1 and Ar2 are the same or different and are independently selected from the group consisting of the following groups:

[0081]

[0082] In some embodiments of the present application, are independently selected from the following groups:

[0083]

[0084] Specifically, are independently selected from the following groups:

[0085]

[0086]

[0087] In some embodiments of the present application, L3 is selected from a single bond, a substituted or unsubstituted phenylene group, and a substituted or unsubstituted naphthylene group.

[0088] Optionally, the substituents in L3 are the same or different, and are independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl or phenyl.

[0089] Specifically, L3 is selected from a single bond or the following group consisting of:

[0090]

[0091] In some embodiments of the present application, Ar3 is selected from substituted or unsubstituted aromatic groups having 6 to 15 carbon atoms.

[0092] Optionally, the substituents in Ar3 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.

[0093] In some embodiments of the present application, Ar3 is selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted phenanthrenyl.

[0094] Optionally, the substituents in Ar3 are the same or different, and are independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, phenyl or deuterated phenyl.

[0095] Optionally, Ar3 is selected from the group consisting of:

[0096]

[0097] Specifically, Ar3 is selected from the group consisting of:

[0098]

[0099] In some embodiments of the present application, Selected from the group consisting of:

[0100] Specifically, Selected from the group consisting of:

[0101]

[0102] In this application, in Formula 1 Selected from the group consisting of:

[0103]

[0104]

[0105] Specifically, Selected from the group consisting of:

[0106]

[0107]

[0108]

[0109]

[0110] Optionally, the organic compound is selected from the group consisting of the following compounds:

[0111]

[0112]

[0113]

[0114]

[0115]

[0116]

[0117]

[0118]

[0119]

[0120]

[0121] In a second aspect, the present application provides an organic electroluminescent device, comprising an anode and a cathode arranged opposite to each other, and a functional layer arranged between the anode and the cathode; the functional layer comprises the organic compound of the present application.

[0122] Optionally, the organic electroluminescent device is a red organic electroluminescent device.

[0123] In some embodiments of the present application, 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, a hole auxiliary layer 330, an organic light emitting layer 340, an electron transport layer 350 and a cathode 200 which are stacked in sequence.

[0124] In some specific embodiments of the present application, the organic electroluminescent device is a red organic electroluminescent device.

[0125] Optionally, the anode 100 includes the following anode material, which is optionally a material with a large work function that facilitates hole injection into the functional layer. Specific examples of anode materials include: metals such as nickel, platinum, vanadium, chromium, copper, zinc and gold or their alloys; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO) and indium zinc oxide (IZO); combined metals and oxides such as ZnO:Al or SnO2:Sb; or conductive polymers such as poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (PEDT), polypyrrole and polyaniline, but not limited thereto. Preferably, a transparent electrode including indium tin oxide (ITO) as an anode.

[0126] Optionally, the hole transport layer 320 includes one or more hole transport materials, and the hole transport material can be selected from carbazole polymers, carbazole-linked triarylamine compounds or other types of compounds. Those skilled in the art can refer to the prior art for selection, and this application does not make any special restrictions on this. In some embodiments of the present application, the hole transport layer 320 is HT-17.

[0127]

[0128] In one embodiment of the present application, the hole auxiliary layer 330 is an organic compound of the present application.

[0129] 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;

[0130]

[0131] In some embodiments of the present application, the hole injection layer 310 is composed of CuPC and HT-17.

[0132] Optionally, the organic light-emitting layer 340 may be composed of a single light-emitting layer material, or may include a main material and a doping material. Optionally, the organic light-emitting layer 340 is composed of a main material and a doping material, and holes injected into the organic light-emitting layer 340 and 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 main material, and the main material transfers energy to the doping material, thereby enabling the doping material to emit light.

[0133] The main material of the organic light-emitting layer 340 may be a metal chelate compound, a bisphenylethylene derivative, an aromatic amine derivative, a dibenzofuran derivative or other types of materials, and the present application does not impose any special limitation thereto.

[0134] In some embodiments of the present application, the main material of the organic light-emitting layer 340 is RH-01.

[0135] 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. Specific examples of red phosphorescent dopants for red organic electroluminescent devices include, but are not limited to,

[0136]

[0137] In a more specific embodiment, the host material of the organic light emitting layer 340 is RH-01, and the guest material is Ir(piq)2(acac).

[0138] The electron transport layer 350 may be a single-layer structure or a multi-layer structure, and may include one or more electron transport materials, which may be selected from but not limited to ET-01, LiQ, benzimidazole derivatives, oxadiazole derivatives, quinoxaline derivatives or other electron transport materials, and the present application does not make any special restrictions. The materials of the electron transport layer 350 include but are not limited to the following compounds:

[0139]

[0140] In some specific embodiments of the present application, the electron transport layer 350 is composed of ET-01 and LiQ.

[0141] 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.

[0142] In some embodiments of the present application, the electron injection layer 360 may include ytterbium (Yb).

[0143] A third aspect of the present application provides an electronic device, comprising the organic electroluminescent device described in the second aspect of the present application.

[0144] 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.

[0145] The synthesis method of the organic compound of the present application is specifically described below in conjunction with synthesis examples, but the present application is not limited thereto.

[0146] The compounds whose synthesis methods are not mentioned in this application are raw materials obtained from commercial channels.

[0147] Synthesis of intermediate a0:

[0148]

[0149] Under nitrogen protection, 4-bromo-2-chloroiodobenzene (8.0 g; 25.2 mmol), 9-phenanthrene boronic acid (5.6 g; 25.2 mmol), tetrakistriphenylphosphine palladium (0.6 g; 0.5 mmol), potassium carbonate (7.0 g; 50.4 mmol), tetrabutylammonium bromide (1.6 g; 5.0 mmol), toluene (60 mL), ethanol (15 mL) and deionized water (15 mL) were added to a round-bottom flask, the temperature was raised to 75° C.-80° C., and the reaction was stirred for 12 hours; the reaction solution was cooled to room temperature, deionized water was added, the liquid was separated, the organic phase was washed with water and then dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure; the obtained crude product was purified by silica gel column chromatography using a dichloromethane / n-heptane solvent system to obtain a white solid intermediate a0 (6.7 g; yield: 72%).

[0150] Referring to the synthesis method of intermediate a0, reactant A is used to replace 9-phenanthreneboric acid to synthesize the intermediates shown in Table 1 below:

[0151] Table 1

[0152]

[0153] Synthesis of intermediate a1:

[0154]

[0155] Under nitrogen protection, intermediate a0 (6.0 g; 16.3 mmol), phenylboronic acid (2.2 g; 18.0 mmol), tetrakistriphenylphosphine palladium (0.4 g; 0.3 mmol), potassium carbonate (4.5 g; 32.6 mmol), tetrabutylammonium bromide (1.1 g; 3.3 mmol), toluene (50 mL), ethanol (10 mL) and deionized water (10 mL) were added to a round-bottom flask, the temperature was raised to 75°C-80°C, and the reaction was stirred for 16 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 recrystallized and purified using a dichloromethane / n-heptane solvent system to obtain a white solid intermediate a1 (4.7 g; yield: 79%).

[0156] Referring to the synthesis method of intermediate a1, the intermediate a0 is replaced by reactant B, and phenylboronic acid is replaced by reactant C to synthesize the intermediates shown in Table 2 below:

[0157] Table 2

[0158]

[0159]

[0160]

[0161] Synthesis of compound A2:

[0162]

[0163] Under nitrogen protection, intermediate a1 (4.5 g; 12.3 mmol), N-phenyl-4-benzidine (3.0 g; 12.3 mmol), tri(dibenzylideneacetone)dipalladium (0.1 g; 0.1 mmol), 2-dicyclohexylphosphine-2',4',6'-triisopropylbiphenyl (0.1 g; 0.2 mmol), sodium tert-butoxide (1.8 g; 18.5 mmol) and toluene (40 mL) were added to a round-bottom flask, the temperature was raised to 100° C.-105° C., and the reaction was stirred for 24 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 crude product was purified by silica gel column chromatography using a dichloromethane / n-heptane solvent system, and then purified by recrystallization using a dichloromethane / n-heptane solvent system to obtain a white solid compound A2 (4.7 g; yield: 66%).

[0164] Referring to the synthesis method of compound A2, the intermediate a1 is replaced by reactant D, and N-phenyl-4-benzidine is replaced by reactant E to synthesize the compounds in Table 3 below:

[0165] Table 3

[0166]

[0167]

[0168]

[0169]

[0170]

[0171]

[0172] The mass spectrometry data of some compounds are shown in Table 4 below:

[0173] Table 4

[0174] Compound A2 <![CDATA[m / z=574.3(M+H) + ]]> Compound B38 <![CDATA[m / z=816.4(M+H) + ]]> Compound A14 <![CDATA[m / z=690.3(M+H) + ]]> Compound B49 <![CDATA[m / z=826.3(M+H) + ]]> Compound A26 <![CDATA[m / z=726.3(M+H) + ]]> Compound B59 <![CDATA[m / z=826.3(M+H) + ]]> Compound A36 <![CDATA[m / z=730.3(M+H) + ]]> Compound B68 <![CDATA[m / z=802.3(M+H) + ]]> Compound A43 <![CDATA[m / z=700.3(M+H) + ]]> Compound C5 <![CDATA[m / z=624.3(M+H) + ]]> Compound A51 <![CDATA[m / z=740.3(M+H) + ]]> Compound C12 <![CDATA[m / z=739.3(M+H) + ]]> Compound A63 <![CDATA[m / z=764.3(M+H) + ]]> Compound C23 <![CDATA[m / z=690.3(M+H) + ]]> Compound A72 <![CDATA[m / z=740.3(M+H) + ]]> Compound C34 <![CDATA[m / z=714.3(M+H) + ]]> Compound A83 <![CDATA[m / z=776.3(M+H) + ]]> Compound C40 <![CDATA[m / z=789.3(M+H) + ]]> Compound B3 <![CDATA[m / z=738.3(M+H) + ]]> Compound C51 <![CDATA[m / z=680.2(M+H) + ]]> Compound B12 <![CDATA[m / z=680.2(M+H) + ]]> Compound C65 <![CDATA[m / z=842.4(M+H) + ]]> Compound B28 <![CDATA[m / z=814.3(M+H) + ]]> Compound A16 <![CDATA[m / z=700.3(M+H) + ]]> Compound A21 <![CDATA[m / z=814.3(M+H) + ]]> Compound A67 <![CDATA[m / z=888.4(M+H) + ]]> Compound A90 <![CDATA[m / z=508.3(M+H) + ]]> Compound A91 <![CDATA[m / z=736.3(M+H) + ]]> Compound C54 <![CDATA[m / z=842.4(M+H) + ]]> Compound C67 <![CDATA[m / z=700.3(M+H) + ]]>

[0175] The NMR data of some compounds are shown in Table 5 below:

[0176] Table 5

[0177]

[0178] Preparation of organic electroluminescent devices

[0179] Example 1: Red organic electroluminescent device

[0180] The anode was prepared by the following process: ITO / Ag / ITO with a thickness of A glass substrate (manufactured by Corning) was cut into a size of 40 mm × 40 mm × 0.7 mm and prepared into an experimental substrate with cathode, anode and insulating layer patterns using a photolithography process. The surface was treated with ultraviolet ozone and O2:N2 plasma to increase the work function of the anode (experimental substrate) and remove scum.

[0181] On the experimental substrate (anode), CuPC:HT-17 was co-evaporated at a deposition rate ratio of 2%:98% to a thickness of A hole injection layer (HIL) is formed, and then a layer of HT-17 is used to form a hole transport layer (HTL).

[0182] Compound A2 is vacuum-deposited on the hole transport layer to form of the hole-assisting layer.

[0183] On the hole auxiliary layer, RH-01 and Ir(piq)2(acac) were co-evaporated at a film thickness ratio of 96%:4% to form of an organic light-emitting layer (R-EML).

[0184] Continue to co-evaporate ET-01 and LiQ in a ratio of 1:1 on the light-emitting layer to form The electron transport layer (ETL) is formed by evaporating Yb on the electron transport layer to form a layer with a thickness of Then, magnesium (Mg) and silver (Ag) were mixed at a deposition rate of 1:9 and vacuum-deposited on the electron injection layer to form a layer with a thickness of cathode.

[0185] Finally, HT-18 is evaporated on the cathode to form a thickness of An organic cover layer (CPL) is formed to complete the manufacture of the organic light-emitting device.

[0186] Example 2-30

[0187] An organic electroluminescent device was prepared in the same manner as in Example 1, except that the compound shown in the following Table 6 was used instead of Compound A2 when forming the hole assisting layer.

[0188] Comparative Examples 1-4

[0189] An organic electroluminescent device was prepared in the same manner as in Example 1, except that compound A, compound B and compound C shown in Table 6 were used instead of compound A2 when forming the hole auxiliary layer.

[0190] Among them, the other material structures used in the above embodiments and comparative examples are as follows

[0191]

[0192] The devices of Examples 1-30 and Comparative Examples 1-3 were heated at 10 mA / cm 2 IVL (current, voltage, brightness, etc.) was tested under current density conditions at 30 mA / cm 2 The T95 life was tested under current density, and the test results are shown in Table 6 below.

[0193] Table 6 Device performance test results

[0194]

[0195]

[0196] According to the results of Table 6 above, the performance of the organic electroluminescent devices of Examples 1-30 is improved compared to the organic electroluminescent devices of Comparative Examples 1 to 3. Specifically, the driving voltage of the organic electroluminescent devices of Examples 1 to 30 is close to that of the Comparative Examples, the current efficiency is increased by at least 12.1%, and the life is increased by at least 10.9%. Therefore, using the organic compound of the present application as a hole auxiliary layer of an organic electroluminescent device can significantly improve the device performance.

[0197] Compared with Comparative Examples 1-3, the embodiments of the present application have significantly lower driving voltage, as well as improved current efficiency and device life.

[0198] Compared with compound A, the compound of the present application has significantly improved luminous efficiency and lifetime characteristics while having similar driving voltages. The reason for this may be that compared with compound A, the aromatic substituent in the compound of the present application is located at the meta position of the amine group rather than the para position, thereby maintaining a deeper HOMO energy level and a high T1 energy level.

[0199] The life of the compound of the present application is significantly improved compared with compound B. The reason for this may be that the aryl substituent in the compound of the present application is located at the para position rather than the ortho position of the phenanthrenyl group on the phenyl group, so that the compound can better maintain a high overlap rate of intermolecular orbitals through the spatial conjugation effect.

[0200] Compared with compound C, the efficiency and life of the organic electroluminescent device of the compound of the present application are significantly improved. The reason may be that the compound of the present application is connected to an aryl group at the 5-position of the phenyl group of aniline, and such connection maintains a high coverage of the molecular HOMO orbital.

[0201] Those skilled in the art will readily appreciate other embodiments of the present application after considering the specification and practicing the invention disclosed herein. The present application is intended to cover any modification, use or adaptation of the present application, which follows the general principles of the present application and includes common knowledge or customary techniques in the art that are not disclosed in the present application. The specification and examples are intended to be exemplary only, and the true scope and spirit of the present application are indicated by the following claims.

Claims

1. An organic compound, characterized in that The organic compound is selected from the group consisting of the following compounds:

2. An organic electroluminescent device, characterized in that: The invention comprises an anode and a cathode arranged opposite to each other, and a functional layer arranged between the anode and the cathode; The functional layer comprises the organic compound according to claim 1 .

3. The organic electroluminescent device according to claim 2, characterized in that: The functional layer includes a hole assisting layer; and the hole assisting layer includes the organic compound.

4. The organic electroluminescent device according to claim 2, characterized in that: The organic electroluminescent device is a red organic electroluminescent device.

5. An electronic device, characterized in that An organic electroluminescent device comprising any one of claims 2 to 4.

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