Organic Compound, Organic Electroluminescent Device, and Electronic Device

Abstract

This application relates to an organic compound, an organic electroluminescent device, and an electronic device. The organic compound of this application has a structure shown in Formula 1. When this organic compound is applied to an organic electroluminescent device, the performance of the device can be significantly improved.

Description

Technical Field

[0001] This application belongs to the technical field of organic materials, and particularly relates to an organic compound, an organic electroluminescent device and an electronic device comprising the organic compound. Background Art

[0002] As a new generation of display technology, organic electroluminescent materials (OLEDs) have the advantages of being ultra-thin, self-luminous, wide viewing angle, fast response, high luminous efficiency, good temperature adaptability, simple production process, low driving voltage, low energy consumption, etc., and have been widely used in industries such as flat panel displays, flexible displays, solid state lighting, and vehicle displays.

[0003] Currently, for green organic electroluminescent devices, phosphorescent organic electroluminescent devices are the main development direction and are mainly used in display devices such as mobile phones and vehicles. However, regarding green organic electroluminescent devices, there are still problems such as reduced luminous efficiency and shortened lifespan, which lead to a decline in device performance. Therefore, phosphorescent host materials must solve these efficiency or lifespan problems, and new materials with high efficiency, long lifespan, and suitable for mass production for organic light emitting devices need to be continuously developed.

[0004] It should be noted that the information disclosed in the above background art section is only used to enhance the understanding of the background of this application, and therefore may include information that does not constitute the prior art known to those of ordinary skill in the art. Summary of the Invention

[0005] In view of the above problems existing in the prior art, the purpose of this application is to provide an organic compound, an organic electroluminescent device and an electronic device comprising the organic compound, and 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, enhancing the device efficiency and lifespan.

[0006] According to the first aspect of this application, there is provided an organic compound having a structure shown in Formula 1:

[0007]

[0008] Wherein, * represents a connection site;

[0009] X is selected from C(R 3 R 4 ), O or S;

[0010] A is a substituted or unsubstituted aryl group having 6 - 12 carbon atoms;

[0011] L 1 is selected from a single bond, a substituted or unsubstituted arylene group having 6 - 30 carbon atoms, and a substituted or unsubstituted heteroarylene group having 3 - 30 carbon atoms;

[0012] Ar 1 is selected from substituted or unsubstituted aryl having 6 to 30 carbon atoms and substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms;

[0013] Each R 1 and R 2 are the same or different and are each independently selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 10 carbon atoms, a deuterated alkyl group having 1 to 10 carbon atoms, a halogenated alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms, a deuterated aryl group having 6 to 20 carbon atoms, and a heteroaryl group having 3 to 20 carbon atoms;

[0014] n 1 is the number of R 1 and is selected from 0, 1, 2, 3, 4, 5, 6, or 7. When n 1 is greater than 1, any two R 1 are the same or different;

[0015] n 2 is the number of R 2 and is selected from 0, 1, 2, 3, 4, 5, 6, or 7. When n 2 is greater than 1, any two R 2 are the same or different;

[0016] R 3 and R 4 are each independently selected from hydrogen, deuterium, an alkyl group having 1 to 10 carbon atoms, or a deuterated alkyl group having 1 to 10 carbon atoms;

[0017] The substituents in the substitution of A are the same or different and are each independently selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 4 carbon atoms, a deuterated alkyl group having 1 to 4 carbon atoms, a halogenated alkyl group having 1 to 4 carbon atoms, or a phenyl group;

[0018] The L 1 and Ar 1 have substituents that are the same or different and are each independently selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 10 carbon atoms, a deuterated alkyl group having 1 to 10 carbon atoms, a halogenated alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms, a heteroaryl group having 3 to 20 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, a deuterated aryl group having 6 to 20 carbon atoms, a halogenated aryl group having 6 to 20 carbon atoms, and a triarylsilyl group having 18 to 24 carbon atoms.

[0019] According to a second aspect of the present application, there is provided an organic electroluminescent device including an anode and a cathode disposed opposite to each other, and a functional layer disposed between the anode and the cathode; the functional layer contains the above-described organic compound.

[0020] According to a third aspect of the present application, there is provided an electronic device including the organic electroluminescent device described in the second aspect.

[0021] The present application provides an organic compound having a molecular structure formed by combining 3,3'-bicarbazole with a dibenzo five-membered ring group having aryl substituents at specific positions. Such compounds have enhanced hole mobility and energy transfer efficiency and are suitable for use as hole-type host materials in organic electroluminescent devices; by substituting aryl groups at specific positions, the steric hindrance effect of the molecule is enhanced, the film-forming property of the material is improved, and the device efficiency and lifespan are further enhanced.

[0022] Other features and advantages of the present application will be described in detail in the following specific implementation section. Description of the Drawings

[0023] The drawings are used to provide a further understanding of the present application and constitute a part of the specification. Together with the following specific implementation, they are used to explain the present application, but do not constitute a limitation to the present application.

[0024] Figure 1 It is a schematic structural diagram of an organic electroluminescent device of the present application.

[0025] Figure 2 It is a schematic structural diagram of an electronic device of the present application.

[0026] Reference Signs

[0027] 100, Anode; 200, Cathode; 300, Functional Layer; 310, Hole Injection Layer

[0028] 320, Hole Transport Layer; 330, Hole Auxiliary Layer; 340, Organic Light-Emitting Layer; 350, Electron Transport Layer

[0029] 360, Electron Injection Layer; 400, Electronic Device Specific Embodiments

[0030] Exemplary embodiments will now be described more fully with reference to the drawings. However, the exemplary embodiments can be implemented in various forms and should not be construed as limited to the examples set forth herein; rather, these embodiments are provided so that this application will be more complete and comprehensive, and will fully convey the concept of the exemplary embodiments to those skilled in the art. The features, structures, or characteristics described can be combined in any suitable manner in one or more embodiments. In the following description, numerous specific details are provided to give a thorough understanding of the embodiments of the present application.

[0031] According to the first aspect of the present application, the present application provides an organic compound having a structure shown in Formula 1:

[0032]

[0033] Wherein, * represents a connecting site;

[0034] That is, * represents the connecting site in Formula 1 and ;

[0035] X is selected from C(R 3 R 4 ), O or S;

[0036] A is a substituted or unsubstituted aryl group having 6 to 12 carbon atoms;

[0037] L 1 is 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;

[0038] Ar 1 is selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms and a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms;

[0039] Each R 1 and R 2 are the same or different and are each independently selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 10 carbon atoms, a deuterated alkyl group having 1 to 10 carbon atoms, a halogenated alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms, a deuterated aryl group having 6 to 20 carbon atoms, and a heteroaryl group having 3 to 20 carbon atoms;

[0040] n 1 is the number of R 1 and is selected from 0, 1, 2, 3, 4, 5, 6 or 7. When n 1 is greater than 1, any two R 1 are the same or different;

[0041] n 2 is the number of R 2 and is selected from 0, 1, 2, 3, 4, 5, 6 or 7. When n 2 is greater than 1, any two R 2 are the same or different;

[0042] R 3 and R 4 are each independently selected from hydrogen, deuterium, an alkyl group having 1 to 10 carbon atoms or a deuterated alkyl group having 1 to 10 carbon atoms;

[0043] The substituents in the substitution of A are the same or different and are each independently selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 4 carbon atoms, a deuterated alkyl group having 1 to 4 carbon atoms, a haloalkyl group having 1 to 4 carbon atoms, or a phenyl group;

[0044] The substituents in L 1 and Ar 1 are the same or different and are each independently selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 10 carbon atoms, a deuterated alkyl group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms, a heteroaryl group having 3 to 20 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, a deuterated aryl group having 6 to 20 carbon atoms, a haloaryl group having 6 to 20 carbon atoms, or a triarylsilyl group having 18 to 24 carbon atoms.

[0045] In the present application, the fluorenyl group may be substituted by one or two substituents. In the case where the fluorenyl group is substituted, it may be: etc., but is not limited thereto.

[0046] In the present application, the description methods "each... is independently", "each... is separately independently", and "each... is independently selected from" can be interchanged and should be understood in a broad sense. It may mean that among different groups, the specific options expressed between the same symbols do not affect each other, or it may also mean that within the same group, the specific options expressed between the same symbols do not affect each other. For example, " wherein each q is independently 0, 1, 2, or 3, and each R" is independently selected from hydrogen, deuterium, fluorine, or chlorine", which means that in formula Q-1, 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; in formula Q-2, each benzene ring of the biphenyl has q substituents R", the number q of the 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.

[0047] In the present application, a term such as "substituted or unsubstituted" means that the functional group described after this term may or may not have a substituent (hereinafter, for the sake of convenience of description, the substituent is collectively referred to as Rc). For example, "substituted or unsubstituted aryl" means an aryl having a substituent Rc or an unsubstituted aryl. The above-mentioned substituent, i.e., Rc, may be, for example, deuterium, a halogen group, a cyano group, an alkyl group, a deuterated alkyl group, a haloalkyl group, an aryl group, a heteroaryl group, a cycloalkyl group, a deuterated aryl group, a haloaryl group, a triarylsilyl group, etc.

[0048] In the present application, the number of carbon atoms of a substituted or unsubstituted functional group refers to the total number of all carbon atoms. For example, if L 1is a substituted arylene having 12 carbon atoms, and all carbon atoms of the arylene and its substituents are 12.

[0049] In the present application, an aryl group refers to an optionally functionalized group or substituent derived from an aromatic carbocyclic ring. The aryl group can be a monocyclic aryl group (e.g., phenyl) or a polycyclic aryl group. In other words, the aryl group can be a monocyclic aryl group, a fused-ring aryl group, two or more monocyclic aryl groups conjugated through carbon-carbon bonds, a monocyclic aryl group and a fused-ring aryl group conjugated through carbon-carbon bonds, or two or more fused-ring aryl groups conjugated through carbon-carbon bonds. That is, unless otherwise specified, two or more aromatic groups conjugated through carbon-carbon bonds can also be regarded as the aryl group in the present application. Among them, the fused-ring aryl group can include, for example, bicyclic fused aryl groups (e.g., naphthyl), tricyclic fused aryl groups (e.g., phenanthryl, fluorenyl, anthryl), etc. The aryl group does not contain heteroatoms such as B, N, O, S, P, Se, and Si. Examples of the aryl group can include, but are not limited to, phenyl, naphthyl, fluorenyl, anthryl, phenanthryl, biphenyl, terphenyl, benzo[9,10]phenanthryl, pyrenyl, benzo[a]pyrenyl, group, spirobifluorenyl, etc. In the present application, the arylene involved refers to a divalent group formed by further removing one hydrogen atom from the aryl group.

[0050] In the present application, terphenyl includes

[0051] In the present application, the substituted aryl group can 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 of the substituted aryl group refers to the total number of carbon atoms of the aryl group and the substituents on the aryl group. For example, a substituted aryl group having 18 carbon atoms refers to the total number of carbon atoms of the aryl group and the substituents being 18.

[0052] In the present application, a heteroaryl refers to a monovalent aromatic ring or its derivative containing 1, 2, 3, 4, 5, 6 or 7 heteroatoms in the ring, and the heteroatoms can be at least one of B, O, N, P, Si, Se and S. The heteroaryl can be a monocyclic heteroaryl or a polycyclic heteroaryl. In other words, the heteroaryl can be a single aromatic ring system or a plurality of aromatic ring systems conjugated through carbon-carbon bonds, and any aromatic ring system is an aromatic monocyclic ring or an aromatic fused ring. Exemplarily, the heteroaryl can include thiophenyl, furyl, pyrrolyl, imidazolyl, thiazolyl, oxazolyl, oxadiazolyl, triazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, acridinyl, pyridazinyl, pyrazinyl, quinolinyl, quinazolinyl, quinoxalinyl, phenoxazinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, isoquinolinyl, indolyl, carbazolyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothienyl, dibenzothienyl, thienothienyl, benzofuryl, phenanthrolinyl, isoxazolyl, thiadiazolyl, benzothiazolyl, phenothiazinyl, silafluorene, dibenzofuryl, and N-phenylcarbazolyl, N-pyridylcarbazolyl, N-methylcarbazolyl, etc., but not limited thereto. Among them, thiophenyl, furyl, phenanthrolinyl, etc. are heteroaryls of the single aromatic ring system type, and N-phenylcarbazolyl, N-pyridylcarbazolyl are heteroaryls of the polycyclic system type conjugated through carbon-carbon bonds. In the present application, the sub-heteroaryl involved refers to a divalent group formed by further removing one hydrogen atom from the heteroaryl.

[0053] In the present application, the substituted heteroaryl can be one or more than two hydrogen atoms in the heteroaryl 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 of the substituted heteroaryl refers to the total number of carbon atoms of the heteroaryl and the substituents on the heteroaryl.

[0054] In the present application, the number of carbon atoms of the substituted or unsubstituted aryl group can be 6-30. 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, 25, 26, 27, 28, 29, 30.

[0055] In the present application, specific examples of the aryl group as a substituent include, but are not limited to, phenyl, biphenyl, naphthyl, fluorenyl, phenanthryl, anthryl, yl.

[0056] In the present application, the number of carbon atoms of the substituted or unsubstituted heteroaryl group can be 3-30. For example, the number of carbon atoms can be 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30.

[0057] In the present application, specific examples of the heteroaryl as a substituent include, but are not limited to, carbazolyl, dibenzofuranyl, dibenzothiophenyl, quinolinyl, quinazolinyl, quinoxalinyl, isoquinolinyl, N-phenylcarbazolyl.

[0058] In the present application, the non-positioning linking bond refers to a single bond extending from the ring system. It indicates that one end of the linking bond can be connected to any position in the ring system penetrated by the bond, and the other end is connected to the rest of the compound molecule.

[0059] 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-positioning linking bonds penetrating the bicyclic ring, and the meaning it represents includes any possible linking manner shown in formulas (f-1) - (f-10).

[0060]

[0061] For another example, as shown in the following formula (X'), the dibenzofuranyl group represented by formula (X') is connected to other positions of the molecule through a non-positioning linking bond extending from the middle of one benzene ring on one side, and the meaning it represents includes any possible linking manner shown in formulas (X'-1) - (X'-4).

[0062]

[0063] 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 can be, for example, 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, n-hexyl, n-octyl, 2-ethylhexyl, nonyl, decyl, 3,7-dimethyloctyl, etc.

[0064] In the present application, the halogen group can be, for example, fluorine, chlorine, bromine, iodine.

[0065] In the present application, the number of carbon atoms of the cycloalkyl group having 3 to 10 carbon atoms can be, for example, 3, 4, 5, 6, 7, 8, 10. Specific examples of the cycloalkyl group include, but are not limited to, cyclopentyl, cyclohexyl.

[0066] In the present application, specific examples of the triarylsilyl group having 18 to 24 carbon atoms include, but are not limited to, triphenylsilyl, etc.

[0067] In the present application, specific examples of the deuterated alkyl group having 1 to 10 carbon atoms include, but are not limited to, trideuteriomethyl.

[0068] In the present application, specific examples of deuterated aryl groups having 6 to 20 carbon atoms include, but are not limited to, monodeuterated phenyl, dideuterated phenyl, trideuterated phenyl, tetradeuterated phenyl, and pentadeuterated phenyl.

[0069] In the present application, specific examples of halogenated aryl groups having 6 to 20 carbon atoms include, but are not limited to, monofluorophenyl, difluorophenyl, trifluorophenyl, tetrafluorophenyl, and pentafluorophenyl.

[0070] In some embodiments of the present application, the organic compound is selected from the compounds represented by Formula 1-1, Formula 1-2, Formula 1-3, Formula 1-4, Formula 1-5, and Formula 1-6:

[0071]

[0072]

[0073] In some embodiments of the present application, A is selected from substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, and substituted or unsubstituted naphthyl.

[0074] Optionally, the substituents in A are the same or different and are independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, or phenyl.

[0075] In some other embodiments of the present application, A is selected from

[0076] In some preferred embodiments of the present application, X is selected from O or S, and A is

[0077] In some embodiments of the present application, the L 1 is selected from a single bond, a substituted or unsubstituted arylene group having 6 to 12 carbon atoms, and a substituted or unsubstituted heteroarylene group having 12 to 20 carbon atoms.

[0078] Optionally, the substituents in L 1 are the same or different and are independently selected from deuterium, a halogen group, cyano, an alkyl group having 1 to 5 carbon atoms, phenyl, or pentadeuterated phenyl.

[0079] In some other embodiments of the present application, the L 1 is selected from a single bond, substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted biphenylene, substituted or unsubstituted carbazolylene, substituted or unsubstituted dibenzofuranylene, and substituted or unsubstituted dibenzothiophenylene.

[0080] Optionally, the L 1The substituents therein are the same or different and are each independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, phenyl or pentadeuterophenyl.

[0081] In some embodiments of the present application, the L 1 is selected from a single bond, a substituted or unsubstituted group Q, wherein the unsubstituted group Q is selected from the group consisting of the following groups:

[0082]

[0083] The substituted group Q has one or more than two substituents, and the substituents are independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, phenyl or pentadeuterophenyl, and when the number of substituents of the group Q is greater than 1, the substituents are the same or different.

[0084] Optionally, the L 1 is selected from a single bond or the group consisting of the following groups:

[0085]

[0086] In some embodiments of the present application, the Ar 1 is selected from a substituted or unsubstituted aryl group having 6 to 25 carbon atoms, a substituted or unsubstituted heteroaryl group having 12 to 20 carbon atoms.

[0087] Optionally, the substituents in the Ar 1 are the same or different and are each independently selected from deuterium, a halogen group, cyano, an alkyl group having 1 to 5 carbon atoms, phenyl or pentadeuterophenyl.

[0088] Optionally, the Ar 1 is selected from a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, a substituted or unsubstituted heteroaryl group having 12 to 18 carbon atoms.

[0089] In some other embodiments of the present application, the Ar 1 is selected from a substituted or unsubstituted phenyl, a substituted or unsubstituted biphenyl, a substituted or unsubstituted naphthyl, a substituted or unsubstituted fluorene, a substituted or unsubstituted terphenyl, a substituted or unsubstituted dibenzofuran, a substituted or unsubstituted dibenzothiophene, a substituted or unsubstituted carbazole.

[0090] Optionally, the substituents in the Ar 1 are the same or different and are each independently selected from deuterium, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, phenyl or pentadeuterophenyl.

[0091] In some embodiments of the present application, the Ar 1Selected from substituted or unsubstituted group W, wherein the unsubstituted group W is selected from the group consisting of the following groups:

[0092]

[0093] The substituted group W has one or more than two substituents, and the substituents in the substituted group W are independently selected from the group consisting of deuterium, fluorine, cyano, phenyl, methyl, ethyl, n-propyl, isopropyl, tert-butyl, phenyl or pentadeuterophenyl, and when the number of substituents on group W is greater than 1, the substituents are the same or different.

[0094] Optionally, said Ar 1 is selected from the group consisting of the following groups:

[0095]

[0096] Specifically, Ar 1 and Ar 2 are the same or different and are independently selected from the group consisting of the following groups:

[0097]

[0098]

[0099] In some embodiments of the present application, is selected from substituted or unsubstituted group V, wherein the unsubstituted group V is selected from the group consisting of the following groups:

[0100]

[0101] The substituted group V has one or more than two substituents, and the substituents in the substituted group V are independently selected from the group consisting of deuterium, fluorine, cyano, phenyl, methyl, ethyl, n-propyl, isopropyl, tert-butyl, phenyl or pentadeuterophenyl, and when the number of substituents on group V is greater than 1, the substituents are the same or different.

[0102] Optionally, is selected from the group consisting of the following groups:

[0103]

[0104] In some embodiments of the present application, each R 1 and R 2 are the same or different and are independently selected from deuterium, halogen group, cyano, alkyl with 1-5 carbon atoms, aryl with 6-12 carbon atoms, deuterated aryl with 6-12 carbon atoms.

[0105] Optionally, each R 1 and R2 Same or different, and each independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, phenyl, naphthyl, biphenyl or pentadeuterophenyl.

[0106] Further optionally, each R 1 and R 2 Same or different, and each independently selected from deuterium, phenyl or pentadeuterophenyl.

[0107] In some other embodiments of the present application, each R 1 and R 2 Same or different, and each independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl or the group consisting of the following groups:

[0108]

[0109] In some other embodiments of the present application, R 3 and R 4 Same or different, and each independently selected from hydrogen, deuterium or methyl.

[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]

[0122]

[0123]

[0124]

[0125]

[0126] According to a second aspect of the present application, the present application provides an organic electroluminescent device, including an anode and a cathode disposed opposite to each other, and a functional layer disposed between the anode and the cathode; the functional layer contains the organic compound of the present application.

[0127] Optionally, the functional layer contains an organic light-emitting layer.

[0128] Further optionally, the organic light-emitting layer contains the organic compound of the present application.

[0129] In some embodiments of the present application, the organic electroluminescent device is a phosphorescent device.

[0130] In some specific embodiments of the present application, the organic electroluminescent device is a green organic electroluminescent device.

[0131] In some embodiments of the present application, the organic electroluminescent device sequentially includes an anode (ITO substrate), a hole transport layer, a hole auxiliary layer, an organic light-emitting layer, an electron transport layer, an electron injection layer, a cathode (Mg-Ag mixture), and an organic cover layer.

[0132] In a specific embodiment of the present application, as Figure 1 shown, the organic electroluminescent device of the present application includes an anode 100, a cathode 200 disposed opposite to the anode 100, and at least one organic layer 300 disposed between the anode layer and the cathode layer. The organic layer 300 includes a hole injection layer 310, a hole transport layer 320, a hole auxiliary layer 330, an organic light-emitting layer 340, an electron transport layer 350, and an electron injection layer 360 that are sequentially stacked.

[0133] Optionally, the anode 100 includes the following anode materials, which are preferably materials with a large work function (work function) that contribute to hole injection into the organic layer. Specific examples of the anode materials include: metals such as nickel, platinum, vanadium, chromium, copper, zinc, and gold, or their alloys; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); combinations of metals and oxides such as ZnO:Al or SnO 2 :Sb; or conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylenedioxy)thiophene] (PEDT), polypyrrole, and polyaniline, but not limited thereto. In a specific embodiment of the present application, the anode selects an ITO substrate.

[0134] Optionally, the hole transport layer 320 may include one or more hole transport materials, which may be selected from carbazole polymers, carbazole-linked triarylamine compounds, or other types of compounds, and the present application does not make special limitations thereto. For example, in some embodiments of the present application, the hole transport layer 320 is composed of HT-4.

[0135]

[0136]

[0137] Optionally, the hole auxiliary layer 330 may include one or more hole transport materials, which may be selected from carbazole polymers, carbazole-linked triarylamine compounds, or other types of compounds, and the present application does not make special limitations thereto. For example, in some embodiments of the present application, the hole auxiliary layer 330 is composed of HT-20.

[0138] Optionally, a hole injection layer 310 may be further disposed between the anode 100 and the hole transport layer 320 to enhance the ability to inject holes into the first hole transport layer 320. The hole injection layer 310 may be selected from benzidine derivatives, starburst arylamine compounds, phthalocyanine derivatives, or other materials, and the present application does not make special limitations thereto. The material of the hole injection layer 310 may be selected from the following compounds or any combination thereof, for example;

[0139]

[0140]

[0141] In one embodiment of the present application, the hole injection layer 310 is composed of HAT-CN.

[0142] Optionally, the organic light-emitting layer 340 may be composed of a single light-emitting material or may include a host material and a guest material. Optionally, the organic light-emitting layer 340 is composed of a host material and a guest material. The holes injected into the organic light-emitting layer 340 and the electrons injected into the organic light-emitting layer 330 may recombine in the organic light-emitting layer 340 to form excitons. The excitons transfer energy to the host material, and the host material transfers energy to the guest material, thereby enabling the guest material to emit light.

[0143] The host material of the organic light-emitting layer 340 may be a hybrid host material, wherein the hybrid host material includes a hole-type host material and an electron-type host material. The electron-type host material may be a triazine material, a quinoline material, etc., and the present application does not make special limitations thereto. For example, specific examples of the electron-type host material include, but are not limited to,

[0144]

[0145] In a specific embodiment of the present application, the electron-type host material of the organic light-emitting layer is

[0146] In a specific embodiment of the present application, the hole-type host material of the organic light-emitting layer is the organic compound of the present application.

[0147] The guest material of the organic light-emitting layer 340 can be a compound or its derivative having a condensed aryl ring, a compound or its derivative having a heteroaryl ring, an aromatic amine derivative, or other materials, and the present application does not make special restrictions thereon. The guest material is also called a doping material or a dopant. It can be classified into a fluorescent dopant and a phosphorescent dopant according to the light-emitting type. For example, specific examples of the green phosphorescent dopant include, but are not limited to,

[0148]

[0149] In an embodiment of the present application, the organic electroluminescent device is a green organic electroluminescent device, the host material of the organic electroluminescent layer 340 is the organic compound of the present application and H52, and the guest material is Ir(ppy) 2 acac.

[0150] The electron transport layer 350 can be a single-layer structure or a multi-layer structure, and it can include one or more electron transport materials. The electron transport materials can be selected from benzimidazole derivatives, oxadiazole derivatives, quinoxaline derivatives, or other electron transport materials, and the present application does not make special limitations thereon. For example, in some embodiments of the present application, the electron transport layer 350 can be composed of ET-01 and LiQ. The materials of the electron transport layer 350 include, but are not limited to, the following compounds:

[0151]

[0152] In an embodiment of the present application, the electron transport layer 350 can be composed of ET-01 (the structure is shown below) and LiQ.

[0153] Optionally, the cathode 200 includes the following cathode materials, which are materials with a small work function that help electron injection into the organic layer. Specific examples of the cathode materials include: metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or their alloys; or multi-layer materials such as LiF / Al, Liq / Al, LiO 2 / Al, LiF / Ca, LiF / Al, and BaF 2 / Ca, but not limited thereto. Preferably, a metal electrode including silver and magnesium is used as the cathode.

[0154] Optionally, an electron injection layer 360 may also be provided between the cathode 200 and the electron transport layer 350 to enhance the ability to inject electrons into the electron transport layer 350. The electron injection layer 360 may include inorganic materials such as alkali metal sulfides and alkali metal halides, or may include complexes of alkali metals and organic substances. In some embodiments of the present application, the electron injection layer 360 may include LiQ.

[0155] The present application also provides an electronic device, which includes the organic electroluminescent device described in the present application.

[0156] For example, as Figure 2 shown, the electronic device provided by the present application is a first electronic device 400, and the first electronic device 400 includes any one of the organic electroluminescent devices described in the above organic electroluminescent device embodiments. The electronic device may be a display device, a lighting device, an optical communication device or other types of electronic devices, and may include, for example, but not limited to, a computer screen, a mobile phone screen, a television, an electronic paper, an emergency lighting lamp, an optical module, etc. Since the first electronic device 400 has the above organic electroluminescent device, it has the same beneficial effects, which will not be elaborated herein again.

[0157] The present application will be described in detail below with reference to embodiments. However, the following description is for explaining the present application and does not limit the scope of the present application in any way.

[0158] Synthesis of Intermediate sub A-1

[0159]

[0160] 1-Bromo-7-chlorodibenzofuran (50.0 g, 177.6 mmol), deuterated phenylboronic acid (22.5 g, 177.6 mmol), tetrakis(triphenylphosphine)palladium (2.0 g, 1.7 mmol), potassium carbonate (49.1 g, 355.2 mmol), tetrabutylammonium bromide (0.5 g, 1.7 mmol) were added to a three-necked flask, and toluene (400 mL), ethanol (100 mL) and deionized water (100 mL) were added to the three-necked flask. Under nitrogen protection, the temperature was raised to 76 °C, and the mixture was heated under reflux and stirred for 18 h. After cooling to room temperature, stirring was stopped, the reaction solution was washed with water, and the organic phase was separated, dried with anhydrous magnesium sulfate, and the solvent was removed under reduced pressure to obtain a crude product; the crude product was purified by silica gel column chromatography using dichloromethane / n-heptane as the mobile phase to obtain a white product sub A-1 (31.2 g, 62%).

[0161] Referring to the synthesis method of sub A-1, reactant A in Table 1 below was substituted for 1-bromo-7-chlorodibenzofuran, and reactant B was substituted for deuterated phenylboronic acid to synthesize the intermediate compound sub A-X shown in Table 1 below:

[0162] Table 1

[0163]

[0164]

[0165] Synthesis of Intermediate sub B-2

[0166]

[0167] 9-(p-Tolyl)-9H-carbazole-3-boronic acid (31.2 g, 103.6 mmol), 3-bromocarbazole (25.0 g, 105.5 mmol), tetrakis(triphenylphosphine)palladium(0) (1.1 g, 1.0 mmol), potassium carbonate (28.0 g, 203.1 mmol), tetrabutylammonium bromide (0.3 g, 1.0 mmol) were added into a three-necked flask. Toluene (200 mL), ethanol (100 mL) and deionized water (50 mL) were added into the three-necked flask. Under nitrogen protection, the temperature was raised to 76 °C, and the mixture was heated under reflux with stirring for 18 h. After cooling to room temperature, stirring was stopped. The reaction mixture was washed with water and the organic phase was separated, dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure to obtain a crude product. The crude product was purified by silica gel column chromatography using dichloromethane / n-heptane as the mobile phase to obtain a white product sub B-2 (27.4 g, 64%).

[0168] Referring to the synthesis method of sub B-2, using reactant C in Table 2 below to replace 9-(p-tolyl)-9H-carbazole-3-boronic acid, the intermediate sub B-X shown in Table 2 below was synthesized:

[0169] Table 2

[0170]

[0171]

[0172]

[0173] Synthesis of Compound A1

[0174]

[0175] Sub A-1 (7.1 g, 24.9 mmol), sub B-1 (10.0 g, 24.4 mmol), tris(dibenzylideneacetone)dipalladium(0) (0.20 g, 0.21 mmol), 2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl (0.20 g, 0.4 mmol) and sodium tert-butoxide (3.5 g, 36.7 mmol) were added to xylene (150 mL). The mixture was heated to 140 °C under nitrogen protection and stirred for 4 h. Then it was cooled to room temperature. The reaction mixture was washed with water, dried over magnesium sulfate, filtered, and the solvent was removed under reduced pressure. The crude product was recrystallized and purified using a dichloromethane / n-heptane system to obtain compound A1 (11.5 g, yield 72%). Mass spectrum: m / z = 656.27 [M+H] + 。Referring to the synthesis method of compound A1, the reactant D in Table 3 below was used to replace sub A-1, and the reactant E was used to replace sub B-1 to synthesize the compounds shown in Table 3 below:

[0176] Table 3

[0177]

[0178]

[0179]

[0180]

[0181]

[0182] Synthesis of intermediate sub 1-I-B 1

[0183]

[0184] o-Chloronitrobenzene (50.0 g, 317.3 mmol), deuterated phenylboronic acid (40.2 g, 317.3 mmol), tetrakis(triphenylphosphine)palladium(0) (3.6 g, 3.1 mmol), potassium carbonate (87.7 g, 634.7 mmol), tetrabutylammonium bromide (1.0 g, 3.1 mmol) were added to a three-necked flask. Toluene (400 mL), ethanol (200 mL) and deionized water (100 mL) were added to the three-necked flask. The temperature was raised to 76 °C under nitrogen protection, and the mixture was heated under reflux and stirred for 18 h. It was cooled to room temperature, the stirring was stopped, the reaction mixture was washed with water, the organic phase was separated, dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure to obtain the crude product. The crude product was purified by silica gel column chromatography using dichloromethane / n-heptane as the mobile phase to obtain intermediate sub1-I-B1 (42.7 g, 66%).

[0185] Synthesis of intermediate sub 1-II-B1

[0186]

[0187] The intermediate sub 1-I-B1 (40.0 g, 195.8 mmol), triphenylphosphine (102.7 g, 391.6 mmol), and o-dichlorobenzene (400 mL) were added to a three-necked flask. Under nitrogen protection, the temperature was raised to 150 °C, and the mixture was heated under reflux with stirring for 18 h. After cooling to room temperature, stirring was stopped. The reaction solution was washed with water, and the organic phase was separated, dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure to obtain a crude product. The crude product was purified by silica gel column chromatography using dichloromethane / n-heptane as the mobile phase to obtain the intermediate sub 1-II-B1 (19.1 g, 57%).

[0188] Synthesis of intermediate sub 1-III-B1

[0189]

[0190] Sub 1-I-B1 (19.0 g, 110.9 mmol), iodobenzene (22.6 g, 110.9 mmol), CuI (4.2 g, 22.1 mmol), K 2 CO 3 (33.7 g, 244.1 mmol), and 18-crown-6 (7.9 g, 44.3 mmol) were added to a three-necked flask, and dry DMF (200 mL) solvent was added. Under nitrogen protection, the temperature was raised to 150 °C, and the temperature was maintained with stirring for 17 hours. After cooling to room temperature, stirring was stopped. The reaction solution was washed with water, and the organic phase was separated, dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure to obtain a crude product. The crude product was purified by silica gel column chromatography using dichloromethane / n-heptane as the mobile phase to obtain the intermediate sub 1-III-B1 (21.4 g, 78%).

[0191] Synthesis of intermediate sub 1-IV-B1

[0192]

[0193] The intermediate sub 1-III-B1 (20.0 g, 80.8 mmol) and dichloromethane (200 mL) were added to a three-necked flask. Under nitrogen protection, N-bromosuccinimide (NBS) (12.9 g, 72.7 mmol) was added. The reaction was stirred overnight. The reaction solution was washed with water, and the organic phase was separated, dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure to obtain a crude product. The crude product was purified by silica gel column chromatography using dichloromethane / n-heptane as the mobile phase to obtain the intermediate sub 1-IV-B1 (14.7 g, 56%).

[0194] Synthesis of intermediate sub B-12

[0195]

[0196] Add sub 1-IV-B 1 (14.0 g, 43.0 mmol), 9H-carbazol-3-ylboronic acid (9.2 g, 43.9 mmol), tetrakis(triphenylphosphine)palladium (0.5 g, 0.4 mmol), potassium carbonate (11.8 g, 86.0 mmol), and tetrabutylammonium bromide (0.1 g, 0.4 mmol) into a three-necked flask. Then add toluene (112 mL), ethanol (28 mL), and deionized water (28 mL) into the three-necked flask. Under nitrogen protection, heat the mixture to 76 °C and stir under reflux for 18 h. Cool to room temperature, stop stirring, wash the reaction solution with water, separate the organic phase, dry it with anhydrous magnesium sulfate, and remove the solvent under reduced pressure to obtain the crude product. Use dichloromethane / n-heptane as the mobile phase to purify the crude product by silica gel column chromatography to obtain intermediate sub B-12 (12.2 g, 69%).

[0197] Synthesis of Compound A104

[0198]

[0199] Add sub B-12 (12.0 g, 29.1 mmol), sub A-1 (8.6 g, 30.6 mmol), tris(dibenzylideneacetone)dipalladium (0.2 g, 0.2 mmol), 2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl (0.2 g, 0.5 mmol), and sodium tert-butoxide (5.6 g, 58.3 mmol) into xylene (120 mL). Under nitrogen protection, heat the mixture to 140 °C and stir for 4 h. Then cool to room temperature, wash the reaction solution with water, add magnesium sulfate for drying, filter, and remove the solvent from the filtrate under reduced pressure. Use dichloromethane / n-heptane system to recrystallize and purify the crude product to obtain Compound A104 (12.2 g, yield 64%). Mass spectrum: m / z = 659.29 [M+H] +

[0200] Mass spectrum data of some compounds are shown in Table 4 below:

[0201] Table 4

[0202] Compound A1 <![CDATA[m / z = 656.27 [M+H] + > Compound A51 <![CDATA[m / z = 746.28 [M+H] + > Compound A4 <![CDATA[m / z = 732.31 [M+H] + > Compound A52 <![CDATA[m / z = 762.26 [M+H] + > Compound A5 <![CDATA[m / z = 732.30 [M+H] + > Compound A63 <![CDATA[m / z = 674.27 [M+H] + > Compound A6 <![CDATA[m / z = 732.30 [M+H] + > Compound A68 <![CDATA[m / z = 651.24 [M+H] + > Compound A3 <![CDATA[m / z = 706.29 [M+H] + > Compound A71 <![CDATA[m / z = 727.27 [M+H] + > Compound A8 <![CDATA[m / z = 746.29 [M+H] + > Compound A30 <![CDATA[m / z = 727.27 [M+H] + > Compound A42 <![CDATA[m / z = 656.27 [M+H] + > Compound A104 <![CDATA[m / z = 659.30 [M+H] + > Compound A45 <![CDATA[m / z = 732.31 [M+H] + > Compound B1 <![CDATA[m / z = 672.25 [M+H] + <!-- 41 -->]]> Compound A46 <![CDATA[m / z = 732.30 [M+H] + > Compound B4 <![CDATA[m / z = 672.24 [M+H] + > Compound A49 <![CDATA[m / z = 746.29 [M+H] + > Compound C1 <![CDATA[m / z = 682.33 [M+H] + > Compound A62 <![CDATA[m / z = 670.29 [M+H] + > Compound A116 <![CDATA[m / z = 732.31 [M+H] + > Compound A48 <![CDATA[m / z = 746.28 [M+H] + > Compound A117 <![CDATA[m / z = 732.34 [M+H] + > Compound A111 <![CDATA[m / z = 821.33 [M+H] + > Compound A88 <![CDATA[m / z = 815.38 [M+H] + > Compound A64 <![CDATA[m / z = 712.34 [M+H] + >

[0203] 1H NMR data of some compounds are shown in Table 5 below:

[0204] Table 5

[0205]

[0206] Preparation and Evaluation of Organic Electroluminescent Devices

[0207] Example 1: Preparation of Green Organic Electroluminescent Device

[0208] The anode was prepared through the following process: The ITO substrate (manufactured by Corning) with a thickness of was cut into a size of 40 mm × 40 mm × 0.7 mm, and through a photolithography process, it was prepared into an experimental substrate with patterns of cathode, anode, and insulating layer. The surface was treated with ultraviolet ozone and O 2 :N 2 plasma to increase the work function of the anode (experimental substrate) and remove scum.

[0209] HAT-CN was vacuum-evaporated on the experimental substrate (anode) to form a hole injection layer (HIL) with a thickness of , and HT-4 was evaporated on the hole injection layer to form a hole transport layer with a thickness of .

[0210] HT-20 was vacuum-evaporated on the hole transport layer to form a hole auxiliary layer with a thickness of .

[0211] On the hole auxiliary layer, the compounds A1﹕H52﹕Ir(ppy) 2 (acac) were co-evaporated at a film thickness ratio of 50%﹕40%﹕10% to form an organic light-emitting layer (EML) with a thickness of .

[0212] ET-01 and LiQ were mixed at a weight ratio of 1:1 and evaporated to form an electron transport layer (ETL) with a thickness of . LiQ was evaporated on the electron transport layer to form an electron injection layer (EIL) with a thickness of . Then, magnesium (Mg) and silver (Ag) were vacuum-evaporated on the electron injection layer at an evaporation rate ratio of 1﹕9 to form a cathode with a thickness of .

[0213] In addition, HT-3 with a thickness of was evaporated on the above-mentioned cathode to form an organic capping layer (CPL), thus completing the manufacture of the organic light-emitting device.

[0214] Examples 2 - 27

[0215] Refer to the method of Example 1 to fabricate the organic electroluminescent device, with the difference that when forming the organic light-emitting layer, the compounds shown in Table 6 below were used to replace compound A1.

[0216] Comparative Examples 1 - 4

[0217] An organic electroluminescent device was fabricated by referring to the method of Example 1, except that when forming the organic light-emitting layer, Compound I, Compound II, Compound III, and Compound IV were used to replace Compound A1.

[0218] The materials and structures used in the above examples and comparative examples are as follows:

[0219]

[0220]

[0221] For the organic electroluminescent device prepared as above, the performance of the device was analyzed under the condition of 15 mA / cm 2 The results are shown in Table 6 below:

[0222] Table 6

[0223]

[0224]

[0225] Referring to Table 6 above, it can be seen that for Examples 1-27 in which the compounds of the present application are used as the hole-type host material in the green light-emitting layer mixed host material, compared with Comparative Examples 1-4, the device voltage, current efficiency, and lifetime have been significantly improved. Specifically, the current efficiency has increased by at least 13.63%, and the lifetime T95 (h) has increased by at least 16.6%. In particular, when the dibenzo five-membered ring is dibenzofuran / dibenzothiophene and the aryl group is pentadeuterophenyl, the device performance is better.

[0226] Compared with Comparative Examples 1 and 2, the compounds of the examples of the present application have an increase in current efficiency of at least 42.8% and an increase in lifetime T95 (h) of at least 34.1%. The reason may be that in the compounds of the comparative examples, the aryl group (pentadeuterophenyl) and the carbazolyl group are connected to the same benzene ring in the dibenzofuranyl group. Such a connection weakens the steric hindrance effect of the compound molecule, reduces the film-forming property of the material, and thus reduces the current efficiency and lifetime of the device.

[0227] Compared with Comparative Examples 3 and 4, the compounds of the examples of the present application have an increase in current efficiency of at least 13.63% and an increase in lifetime T95 (h) of at least 16.6%. The reason may be that the aryl group in the organic compounds of the present application is connected to a specific position in the dibenzo five-membered ring and combined with 3,3-bicarbazole, making the compound have enhanced hole mobility and energy transfer efficiency, and being suitable for use as a hole-type host material in organic electroluminescent devices; and by substituting the aryl group at a specific position, the steric hindrance effect of the molecule is enhanced, the film-forming property of the material is improved, and the device efficiency and lifetime are further enhanced.

[0228] It should be understood that the present application is not limited to the exact structures described above and shown in the drawings, and various modifications and changes can be made without departing from its scope. The scope of the present application is only limited by the appended claims.

Claims

1. An organic electroluminescent device, characterized in that, it includes an anode and a cathode which are oppositely arranged, and a functional layer disposed between the anode and the cathode; the functional layer contains an organic light-emitting layer; the organic electroluminescent device is a green organic electroluminescent device; The organic light-emitting layer contains the organic compound shown in Formula 1 as shown; The organic light-emitting layer shown also includes wherein, * represents a connection site; X is selected from O or S; A is L 1 selected from a single bond, a substituted or unsubstituted phenylene group; L 1 The substituents in it are the same or different and are each independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, phenyl or pentadeuterophenyl; Ar 1 selected from substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted terphenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted carbazolyl; Ar 1 The substituents in 1 are the same or different and are each independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, phenyl or pentadeuterophenyl; Each R 1 and R 2 are the same or different and are each independently selected from deuterium, phenyl or pentadeuterophenyl; n 1 is R 1 the number of, selected from 0, 1, 2, 3, 4, 5, 6 or 7, when n 1 is greater than 1, any two Rs 1 are the same or different; n 2 is the number of R 2 , and is selected from 0, 1, 2, 3, 4, 5, 6 or 7. When n 2 is greater than 1, any two R 2 are the same or different.

2. The organic electroluminescent device according to claim 1, characterized in that, the organic compound shown in Formula 1 is selected from the compounds shown in Formula 1-1, Formula 1-2, Formula 1-3, and Formula 1-4:

3. The organic electroluminescent device according to claim 1, characterized in that, In Formula 1 selected from substituted or unsubstituted group V, wherein the unsubstituted group V is selected from the group consisting of the following groups: the substituted group V has one or more than two substituents, and the substituents in the substituted group V are independently selected from the group consisting of deuterium, fluorine, cyano group, phenyl group, methyl group, ethyl group, n-propyl group, isopropyl group, tert-butyl group or pentadeuterophenyl group, and when the number of substituents on the group V is greater than 1, the substituents are the same or different.

4. The organic electroluminescent device according to claim 1, characterized in that, In Formula 1 selected from the group consisting of the following groups:

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

6. An electronic device, characterized in that, it includes the organic electroluminescent device according to any one of claims 1-5.

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