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 same. Background Art

[0002] With the development of electronic technology and the progress of materials science, the research scope of electro-luminescent or optoelectronic conversion electronic components has become increasingly extensive. Among them, an organic electroluminescent device, also known as an organic light-emitting diode, refers to the phenomenon that an organic light-emitting material is excited by an electric current under the action of an electric field to emit light. Such electronic components generally include a cathode and an anode disposed opposite to each other, and a functional layer disposed 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 which are sequentially stacked. When a voltage is applied between the two electrodes, an electric field is generated between the two electrodes. Under the action of the electric field, electrons on the cathode side move towards the electroluminescent layer, and holes on the anode side also move towards the light-emitting layer. The electrons and holes combine in the electroluminescent layer to form excitons. The excitons are in an excited state and release energy outward, thereby causing the electroluminescent layer to emit light externally.

[0003] Organic charge transport materials are a class of organic semiconductor materials that can achieve the directional and orderly controllable migration of carriers (electrons or holes) under the action of an electric field when carriers are injected. Such materials require excellent electron-donating properties, low ionization potential, high hole mobility, good solubility and amorphous film-forming properties, strong fluorescence performance and light stability. At present, among hole transport materials, triarylamine materials have relatively excellent performance and are one of the research hotspots. Although the prior art discloses materials for preparing hole transport in organic electroluminescent devices, the existing triarylamine hole transport materials perform poorly in terms of voltage, luminous efficiency, power and lifespan 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 purpose of this application is to provide an organic compound, an organic electroluminescent device and an electronic device comprising the organic compound. 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, improving the efficiency and lifespan of the device.

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

[0006]

[0007] Wherein, X is O or S;

[0008] L1 and L2 are the same or different, and are each independently selected from a single bond, a substituted or unsubstituted arylene having 6 to 30 carbon atoms, and a substituted or unsubstituted heteroarylene having 3 to 30 carbon atoms;

[0009] Ar1 and Ar2 are the same or different, and are each independently selected from a substituted or unsubstituted aryl having 6 to 40 carbon atoms, and a substituted or unsubstituted heteroaryl having 3 to 40 carbon atoms;

[0010] L3 is selected from a single bond, a substituted or unsubstituted arylene having 6 to 30 carbon atoms;

[0011] Ar3 is selected from a substituted or unsubstituted aryl having 6 to 30 carbon atoms;

[0012] The substituents in L3 and Ar3 are the same or different, and are each independently selected from deuterium, a halogen group, a cyano group, an alkyl having 1 to 10 carbon atoms, a cycloalkyl having 3 to 20 carbon atoms, an aryl having 6 to 20 carbon atoms, and a deuterated aryl having 6 to 20 carbon atoms;

[0013] The substituents in L1, L2, Ar1 and Ar2 are the same or different, and are each independently selected from deuterium, a halogen group, a cyano group, an alkyl having 1 to 10 carbon atoms, a cycloalkyl having 3 to 20 carbon atoms, a heteroaryl having 12 to 20 carbon atoms, an aryl having 6 to 20 carbon atoms, a deuterated aryl having 6 to 20 carbon atoms, a halogenated aryl having 6 to 20 carbon atoms, a trialkylsilyl having 3 to 12 carbon atoms, a triarylsilyl having 18 to 24 carbon atoms, a halogenated alkyl having 1 to 10 carbon atoms, and a deuterated alkyl having 1 to 10 carbon atoms;

[0014] Optionally, in Ar1 and Ar2, any two adjacent substituents form a ring.

[0015] According to the 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-mentioned organic compound.

[0016] According to the third aspect of the present application, there is provided an electronic device, including the electronic component described in the second aspect.

[0017] The present application provides a compound with a 2,5-disubstituted aniline as the core structure. At the ortho-position (2-position) of the amino group, dibenzofuran / dibenzothiophene is connected, and this dibenzofuran / dibenzothiophene is specifically connected to aniline through the 2-position or 3-position. This connection method makes this part an electron-rich rigid planar group, so that the molecule can have good ortho-space conjugation effect and optoelectronic stability. Further, an aryl group is connected to the 5-position of aniline, so that while maintaining the molecular energy level characteristics of the compound, the space effect is enhanced, and the molecule has a stable amorphous state and enhanced film-forming characteristics. 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 lifetime performance while maintaining a low driving voltage.

[0018] Other features and advantages of the present application will be described in detail in the following specific implementation section. BRIEF DESCRIPTION OF THE DRAWINGS

[0019] 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.

[0020] Figure 1 It is a schematic structural diagram of an organic electroluminescent device of the present application.

[0021] Figure 2 It is a schematic structural diagram of an electronic device of the present application.

[0022] REFERENCE NUMERALS

[0023] 100, Anode; 200, Cathode; 300, Functional layer; 310, Hole injection layer

[0024] 320, Hole transport layer; 330, Hole auxiliary layer; 340, Organic light-emitting layer; 350, Electron transport layer

[0025] 360, Electron injection layer; 400, Electronic device DETAILED DESCRIPTION OF THE EMBODIMENTS

[0026] Now, exemplary embodiments will be described more fully with reference to the accompanying 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 described features, structures, or characteristics can be combined in any suitable manner in one or more embodiments. In the following description, numerous specific details are provided to give a full understanding of the embodiments of the present application.

[0027] In a first aspect, the present application provides an organic compound having a structure as shown in Formula 1:

[0028]

[0029] Wherein, X is O or S;

[0030] L1 and L2 are the same or different, and are each 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;

[0031] Ar1 and Ar2 are the same or different, and are each independently selected from a substituted or unsubstituted aryl group having 6 to 40 carbon atoms, and a substituted or unsubstituted heteroaryl group having 3 to 40 carbon atoms;

[0032] L3 is selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms;

[0033] Ar3 is selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms;

[0034] The substituents in L3 and Ar3 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 cycloalkyl group having 3 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms, and a deuterated aryl group having 6 to 20 carbon atoms;

[0035] The substituents in L1, L2, Ar1 and Ar2 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 cycloalkyl group having 3 to 20 carbon atoms, a heteroaryl group having 12 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms, a deuterated aryl group having 6 to 20 carbon atoms, a halogenated aryl group having 6 to 20 carbon atoms, a trialkylsilyl group having 3 to 12 carbon atoms, a triarylsilyl group having 18 to 24 carbon atoms, a halogenated alkyl group having 1 to 10 carbon atoms, and a deuterated alkyl group having 1 to 10 carbon atoms;

[0036] Optionally, in Ar1 and Ar2, any two adjacent substituents form a ring. [[ID=?]]

[0037] In the present application, in Formula 1, the group The connection site is as shown in Formula shown, can only be connected to at the 2-position or 3-position, and there are no substituents at other positions; that is can only be

[0038]

[0039] It should be noted that there seems to be an unclear tag "? " in the original text at line 28 which is retained as is in the translation. If this is an error in the original, it may need to be corrected for a more accurate translation.In the present application, the terms "optionally" and "optionally" mean that the subsequent described event or circumstance may occur but does not have to occur, and this description includes the cases where the thing or circumstance occurs or does not occur. For example, "Optionally, any two adjacent substituents form a ring;" means that these two substituents may form a ring but do not have to form a ring, including: the scenario where two adjacent substituents form a ring and the scenario where two adjacent substituents do not form a ring.

[0040] In the present application, in "any two adjacent substituents form a ring", "any adjacent" may include having two substituents on the same atom, and may also include having one substituent on each of two adjacent atoms; wherein, when there are two substituents on the same atom, the two substituents may form a saturated or unsaturated ring with the atom to which they are commonly attached; when there is one substituent on each of two adjacent atoms, these two substituents may be fused into a ring. For example, when Ar1 has 2 or more substituents and any two adjacent substituents form a ring, a saturated or unsaturated cyclic group is formed, such as: benzene ring, naphthalene ring, phenanthrene ring, anthracene ring, fluorene ring, cyclopentane, cyclohexane, adamantane, etc.

[0041] In the present application, the fluorenyl group may be substituted by 1 or 2 substituents, and in the case where the fluorenyl group is substituted as described above, it may be: etc., but is not limited thereto.

[0042] In the present application, the description methods "each... independently is", "each... separately independently is" and "each... independently selects from" can be interchanged and should be understood in a broad sense. It can either mean that among different groups, the specific options expressed between the same symbols do not affect each other, or it can mean that within the same group, the specific options expressed between the same symbols do not affect each other. For example, " wherein each q independently is 0, 1, 2 or 3, and each R" independently selects from hydrogen, deuterium, fluorine, chlorine", its meaning is: Formula Q-1 means that there are q substituents R" on the benzene ring, each R" can be the same or different, and the options of each R" do not affect each other; Formula Q-2 means that 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, each R" can be the same or different, and the options of each R" do not affect each other.

[0043] 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. Among them, the above-mentioned substituent, that is, 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 haloalkyl group, a deuterated alkyl group, etc.

[0044] In the present application, the number of carbon atoms of a substituted or unsubstituted functional group refers to all the carbon atoms. For example, if L1 is a substituted arylene having 12 carbon atoms, then the total number of carbon atoms of the arylene and the substituents thereon is 12.

[0045] In the present application, an aryl group refers to an optionally functionalized or substituted group derived from an aromatic carbocyclic ring. An aryl group can be a monocyclic aryl group (such as a phenyl group) or a polycyclic aryl group. In other words, an aryl group can be a monocyclic aryl group, a fused polycyclic aryl group, two or more monocyclic aryl groups conjugated through a carbon-carbon bond, a monocyclic aryl group and a fused polycyclic aryl group conjugated through a carbon-carbon bond, or two or more fused polycyclic aryl groups conjugated through a carbon-carbon bond. That is, unless otherwise specified, two or more aromatic groups conjugated through a carbon-carbon bond can also be regarded as the aryl groups in the present application. Among them, the fused polycyclic aryl group can include, for example, a bicyclic fused aryl group (such as a naphthyl group), a tricyclic fused aryl group (such as a phenanthryl group, a fluorenyl group, an anthryl group), 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, a phenyl group, a naphthyl group, a fluorenyl group, an anthryl group, a phenanthryl group, a biphenyl group, a terphenyl group, a benzo[9,10]phenanthryl group, a pyrenyl group, a benzo[a]pyrenyl group, a spirobifluorenyl group, etc. In the present application, the arylene group involved refers to a divalent group formed by further removing one hydrogen atom from the aryl group.

[0046] In the present application, the terphenyl group includes

[0047] In the present application, a substituted aryl group can be one or more hydrogen atoms in the aryl group being replaced by groups such as a deuterium atom, a halogen group, a cyano group, an aryl group, a heteroaryl group, an alkyl group, a cycloalkyl group, 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 means that the total number of carbon atoms of the aryl group and the substituents is 18.

[0048] In the present application, a heteroaryl is 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, benzothiophenyl, dibenzothiophenyl, thienothiophenyl, benzofuryl, phenanthrolinyl, isoxazolyl, thiadiazolyl, benzothiazolyl, phenothiazinyl, silafluorene, dibenzofuryl, and N-phenylcarbazolyl, N-pyridylcarbazolyl, N-methylcarbazolyl, etc., without being 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.

[0049] In the present application, the substituted heteroaryl can be one or more than two hydrogen atoms in the heteroaryl being substituted 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.

[0050] In the present application, the number of carbon atoms of the substituted or unsubstituted aryl group can be 6-25. 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, 25.

[0051] 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.

[0052] In the present application, the number of carbon atoms of the substituted or unsubstituted heteroaryl can be 12-20. For example, the number of carbon atoms can be 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20.

[0053] In the present application, specific examples of the heteroaryl as a substituent include, but are not limited to, carbazolyl, dibenzofuranyl, and dibenzothiophenyl.

[0054] 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.

[0055] 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).

[0056]

[0057] 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 side benzene ring, and the meaning it represents includes any possible linking manner shown in formulas (X'-1) - (X'-4).

[0058]

[0059] 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.

[0060] In the present application, the halogen group can be, for example, fluorine, chlorine, bromine, or iodine.

[0061] 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 and cyclohexyl.

[0062] In the present application, specific examples of the deuterated aryl include, but are not limited to, pentadeuterated phenyl.

[0063] In some embodiments of the present application, the organic compound is selected from the compounds represented by formula 1-1 or formula 1-2:

[0064] [[ID=3***]]

[0065] In some specific embodiments of the present application, the organic compound is selected from the compounds represented by Formula A, Formula B, Formula C or Formula D:

[0066]

[0067] In some embodiments of the present application, L1 and L2 are the same or different, and are each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 15 carbon atoms, or a substituted or unsubstituted heteroarylene group having 12 to 20 carbon atoms.

[0068] Optionally, the substituents in L1 and L2 are the same or different, and are each independently selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 5 carbon atoms, or a phenyl group.

[0069] In some other embodiments of the present application, L1 and L2 are the same or different, and are each 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, or a substituted or unsubstituted dibenzothiophenyl group.

[0070] Optionally, the substituents in L1 and L2 are the same or different, and are each independently selected from deuterium, fluorine, a cyano group, a methyl group, an ethyl group, a n-propyl group, an isopropyl group, a tert-butyl group, or a phenyl group.

[0071] In some embodiments of the present application, L1 and L2 are the same or different, and are each 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:

[0072]

[0073] The substituted group V has one or more than two substituents, and the substituents are independently selected from deuterium, fluorine, a cyano group, a methyl group, an ethyl group, an isopropyl group, a tert-butyl group, or a phenyl group, and when the number of substituents is greater than 1, the substituents are the same or different.

[0074] Optionally, L1 and L2 are the same or different, and are each independently selected from a single bond or the group consisting of the following groups:

[0075]

[0076] Specifically, L1 and L2 are the same or different, and are each independently selected from a single bond or the group consisting of the following groups:

[0077]

[0078] In some embodiments of the present application, Ar1 and Ar2 are the same or different, and are each 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;

[0079] Optionally, the substituents in Ar1 and Ar2 are the same or different, and are each independently selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 5 carbon atoms, a phenyl group, or a pentadeuterophenyl group;

[0080] Optionally, in Ar1 and Ar2, any two adjacent substituents form a fluorene ring

[0081] In some other embodiments of the present application, Ar1 and Ar2 are the same or different, and are each independently selected from substituted or unsubstituted terphenyl, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted fluorene, substituted or unsubstituted triphenylene, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted spirobifluorene;

[0082] Optionally, the substituents in Ar1 and Ar2 are the same or different, and are each independently selected from deuterium, fluorine, a cyano group, a methyl group, an ethyl group, a n-propyl group, an isopropyl group, a tert-butyl group, a phenyl group, or a pentadeuterophenyl group.

[0083] In some embodiments of the present application, Ar1 and Ar2 are the same or different, and are each independently selected from substituted or unsubstituted group G, wherein the unsubstituted group G is selected from the group consisting of the following groups:

[0084]

[0085] The substituted group G has one or more than two substituents, and the substituents in the substituted group G are each independently selected from the group consisting of deuterium, fluorine, a cyano group, a phenyl group, a methyl group, an ethyl group, a n-propyl group, an isopropyl group, a tert-butyl group, a phenyl group, a pentadeuterophenyl group, and when the number of substituents of group G is greater than 1, the substituents are the same or different.

[0086] Optionally, Ar1 and Ar2 are the same or different, and are each independently selected from the group consisting of the following groups:

[0087]

[0088] Specifically, Ar1 and Ar2 are the same or different, and are each independently selected from the group consisting of the following groups:

[0089]

[0090] In some embodiments of the present application, Each independently selected from the group consisting of the following groups:

[0091]

[0092]

[0093] Specifically, Each independently selected from the group consisting of the following groups:

[0094]

[0095] In some embodiments of the present application, L3 is selected from a single bond, a substituted or unsubstituted phenylene group, or a substituted or unsubstituted naphthylene group.

[0096] Optionally, the substituents in the L3 are the same or different and are each independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl or phenyl.

[0097] Specifically, L3 is selected from a single bond or the group consisting of the following groups:

[0098]

[0099] In some embodiments of the present application, Ar3 is a substituted or unsubstituted aryl group having 6 to 15 carbon atoms.

[0100] Optionally, the substituents in the Ar3 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.

[0101] In some other embodiments of the present application, Ar3 is selected from a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted biphenyl group, or a substituted or unsubstituted phenanthryl group.

[0102] Optionally, the substituents in the Ar3 are the same or different and are each independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, phenyl or pentadeuterophenyl.

[0103] Optionally, Ar3 is selected from the group consisting of the following groups:

[0104]

[0105] Specifically, Ar3 is selected from the group consisting of the following groups:

[0106]

[0107] In some embodiments of the present application, Selected from the group consisting of the following groups:

[0108]

[0109] Specifically, Selected from the group consisting of:

[0110]

[0111]

[0112] In this application, in Formula 1 Selected from the group consisting of:

[0113]

[0114]

[0115] Specifically, Selected from the group consisting of:

[0116]

[0117]

[0118]

[0119] Optionally, the organic compound is selected from the group consisting of:

[0120]

[0121]

[0122]

[0123]

[0124]

[0125]

[0126]

[0127]

[0128]

[0129]

[0130]

[0131] In a second aspect, 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.

[0132] Optionally, the organic electroluminescent device is a red organic electroluminescent device.

[0133] In some embodiments of the present application, the electronic component is an organic electroluminescent device. As Figure 1 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 that are sequentially stacked.

[0137]

[0138] In an embodiment of the present application, the hole auxiliary layer 330 is the organic compound of the present application.

[0139]

[0134] In some specific embodiments of the present application, the organic electroluminescent device is a red organic electroluminescent device.

[0135] Optionally, the anode 100 includes the following anode materials, which are optionally materials with a large work function (work function) that contribute to 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); combinations of metals and oxides such as ZnO∶Al or SnO2∶Sb; or conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylenedioxy)thiophene] (PEDT), polypyrrole, and polyaniline, but not limited thereto. Preferably, indium tin oxide (ITO) is included as the transparent electrode of the anode.

[0136] Optionally, the hole transport layer 320 includes one or more hole transport materials, and the hole transport materials 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 the present application does not make special limitations thereto. In some embodiments of the present application, the hole transport layer 320 is HT-18. Optionally, a hole injection layer 310 may also 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 selected from benzidine derivatives, starburst arylamine compounds, phthalocyanine derivatives or other materials, and this application does not make special restrictions on this. The material of the hole injection layer 310 may, for example, be selected from the following compounds or any combination thereof;

[0140]

[0141]

[0142] In some embodiments of this application, the hole injection layer 310 is composed of CuPC and HT-18.

[0143] Optionally, the organic light-emitting layer 340 may be composed of a single light-emitting layer material, or may include a host material and a dopant material. Optionally, the organic light-emitting layer 340 is composed of a host material and a dopant material. The holes injected into the organic light-emitting layer 340 and the electrons injected into the organic light-emitting layer 340 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 dopant material, thereby enabling the dopant material to emit light.

[0144] The host material of the organic light-emitting layer 340 may be a metal chelate compound, a bisstyryl derivative, an aromatic amine derivative, a dibenzofuran derivative or other types of materials, and this application does not make special restrictions on this.

[0145] In some embodiments of this application, the host material of the organic light-emitting layer 340 is RH-01.

[0146] The guest material of the organic light-emitting layer 340 may 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 this application does not make special restrictions on this. The guest material is also called a dopant material or a dopant. Specific examples of the red phosphorescent dopant for a red organic light-emitting device include, but are not limited to,

[0147]

[0148] In a more specific embodiment, the host material of the organic light-emitting layer 340 is RH-01 and the guest material is RD.

[0149] 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, but not limited to, ET-01, LiQ, benzimidazole derivatives, oxadiazole derivatives, quinoxaline derivatives, or other electron transport materials, and no special limitation is made in this application. The materials of the electron transport layer 350 include, but are not limited to, the following compounds:

[0150]

[0151] In some specific embodiments of this application, the electron transport layer 350 is composed of ET-01 and LiQ.

[0152] In this application, the cathode 200 can include a cathode material, which is a material with a small work function that helps electron injection into the functional layer. Specific examples of the cathode material 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 multi-layer 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.

[0153] In some embodiments of this application, the electron injection layer 360 can include ytterbium (Yb).

[0154] The third aspect of this application provides an electronic device, including the organic electroluminescent device described in the second aspect of this application.

[0155] According to one embodiment, as Figure 2 shown, the provided electronic device is the 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. For example, it can include, but is not limited to, a computer screen, a mobile phone screen, a television, an electronic paper, an emergency lighting lamp, an optical module, etc.

[0156] The following specifically illustrates the synthesis method of the organic compounds of this application in combination with synthesis examples, but this application is not limited thereby.

[0157] Compounds for which the synthesis method is not mentioned in this application are all raw material products obtained through commercial channels.

[0158] Synthesis of intermediate a0:

[0159]

[0160] Under nitrogen protection, 4-bromo-2-chloroiodobenzene (7.5 g; 23.6 mmol), dibenzofuran-3-boronic acid (5.0 g; 23.6 mmol), tetrakis(triphenylphosphine)palladium(0) (0.5 g; 0.5 mmol), potassium carbonate (6.5 g; 47.3 mmol), tetrabutylammonium bromide (1.5 g; 4.7 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 mixture was stirred and reacted for 16 hours. The reaction solution was cooled to room temperature, deionized water was added, and liquid separation was carried out. The organic phase was washed with water and then dried with anhydrous magnesium sulfate. 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 white solid intermediate a1 (6.4 g; yield: 76%). Referring to the synthesis method of intermediate a0, reactant A was used to replace dibenzofuran-3-boronic acid to synthesize the intermediates shown in Table 1 below:

[0161] Table 1

[0162]

[0163]

[0164] Synthesis of intermediate a1:

[0165]

[0166] Under nitrogen protection, intermediate a0 (6.2 g; 17.3 mmol), phenylboronic acid (2.2 g; 18.2 mmol), tetrakis(triphenylphosphine)palladium(0) (0.4 g; 0.3 mmol), potassium carbonate (4.8 g; 34.7 mmol), tetrabutylammonium bromide (1.1 g; 3.5 mmol), toluene (50 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 mixture was stirred and reacted for 16 hours. The reaction solution was cooled to room temperature, deionized water was added, and liquid separation was carried out. The organic phase was washed with water and then dried with anhydrous magnesium sulfate. The solvent was removed under reduced pressure. The obtained crude product was purified by recrystallization using a dichloromethane / n-heptane solvent system to obtain white solid intermediate a1 (4.9 g; yield: 80%)

[0167] Referring to the synthesis method of intermediate a1, reactant B was used to replace intermediate a0 and reactant C was used to replace phenylboronic acid to synthesize the intermediates shown in Table 2 below:

[0168] Table 2

[0169]

[0170]

[0171]

[0172]

[0173] Synthesis of Compound A2:

[0174]

[0175] Under nitrogen protection, intermediate a1 (4.0 g; 11.3 mmol), N-phenyl-4-benzidine (2.8 g; 11.5 mmol), tris(dibenzylideneacetone)dipalladium(0) (0.1 g; 0.1 mmol), 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl (0.1 g; 0.2 mmol), sodium tert-butoxide (1.6 g; 16.9 mmol) and toluene (40 mL) were added to a round-bottom flask. The temperature was raised to 100 °C - 105 °C and the mixture was stirred for 12 hours. The reaction solution was cooled to room temperature, deionized water was added, and the layers were separated. The organic layer was washed with water and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure. The resulting crude product was purified by silica gel column chromatography using a dichloromethane / n-heptane solvent system and then recrystallized using a toluene / n-heptane solvent system to obtain white solid Compound A2 (4.6 g; yield: 72%).

[0176] Referring to the synthesis method of Compound A2, reactant D was used to replace intermediate a1 and reactant E was used to replace N-phenyl-4-benzidine to synthesize the compounds shown in Table 3 below:

[0177] Table 3

[0178]

[0179]

[0180]

[0181]

[0182]

[0183] Mass spectrometry data of some compounds are shown in Table 4 below

[0184] Table 4

[0185]

[0186]

[0187] Nuclear magnetic resonance data of some compounds are shown in Table 5 below

[0188] Table 5

[0189]

[0190] Preparation of Organic Electroluminescent Device

[0191] Example 1: Red Organic Electroluminescent Device

[0192] The anode was prepared through the following process: A glass substrate (manufactured by Corning) with a thickness of ITO / Ag / ITO was cut into a size of 40 mm × 40 mm × 0.7 mm. Using a photolithography process, it was fabricated into an experimental substrate with patterns of cathode, anode, and insulating layer. Surface treatment was carried out using ultraviolet ozone and O2:N2 plasma to increase the work function of the anode (experimental substrate) and remove scum. On the experimental substrate (anode), F4-TCNQ:HT-18 was co-evaporated at a rate ratio of 2%:98% to form a hole injection layer (HIL) with a thickness of

[0193] Then, HT-18 was evaporated on the hole injection layer to form a hole transport layer (HTL) with a thickness of

[0194] Compound A2 was vacuum-evaporated on the hole transport layer to form a hole auxiliary layer with a thickness of

[0195] On the hole auxiliary layer, RH-01 and RD were co-evaporated at a film thickness ratio of 96%:4% to form an organic light-emitting layer (R-EML) with a thickness of

[0196] Continuing on the light-emitting layer, ET-01 and LiQ were co-evaporated at a ratio of 1:1 to form an electron transport layer (ETL) with a thickness of Yb 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 mixed at an evaporation rate ratio of 1:9 and vacuum-evaporated on the electron injection layer to form a cathode with a thickness of

[0197] Finally, HT-19 was evaporated on the cathode to form an organic cover layer (CPL) with a thickness of Thereby completing the manufacture of the organic light-emitting device.

[0198] Examples 2 - 28

[0199] An organic electroluminescent device was fabricated using the same method as in Example 1, except that when forming the hole auxiliary layer, the compounds shown in Table 6 below were used to replace Compound A2.

[0200] Comparative Examples 1 - 4

[0201] An organic electroluminescent device was prepared by the same method as in Example 1, except that Compound A, Compound B, Compound C and Compound D shown in Table 6 were used instead of Compound A2 when forming the hole-assisting layer.

[0202] Among them, the other material structures used in the above embodiments and comparative examples are as follows

[0203]

[0204] The devices of Examples 1-28 and Comparative Examples 1-4 were tested at 10 mA / cm 2 IVL (current, voltage, efficiency, etc.) was tested under current density conditions. 2 The T95 life was tested under the current density, and the test results are shown in Table 6 below.

[0205] Table 6 Device performance test results

[0206]

[0207]

[0208] The results in Table 6 above show that the performance of the organic electroluminescent devices of Examples 1 to 28 is improved compared to the organic electroluminescent devices of Comparative Examples 1 to 4. Specifically, the driving voltage of the organic electroluminescent devices of Examples 1 to 28 is close to that of the comparative examples, the current efficiency is improved by at least 11.4%, and the life is improved by at least 15.2%. Therefore, using the organic compound of the present application as a hole-assisting layer of an organic electroluminescent device has the advantage of improving efficiency and efficiency while maintaining a low operating voltage.

[0209] Compared with Comparative Examples 1-3, the embodiment of the present application has a significantly lower driving voltage, as well as improved current efficiency and device life.

[0210] Compared with compound A, the current efficiency and life of the compound of the present application are significantly improved. The reason for this may be that in the compound of the present application, the dibenzofuran / dibenzothiophene group is connected to the benzene ring of aniline through a specific position. This specific connection method maintains a high coverage of the molecular HOMO orbital, giving the compound molecule a moderate degree of twist, thereby enhancing the spatial aromatic conjugation effect and the hole mobility of the compound.

[0211] Compared with compound B, the current efficiency and life of the compound of the present application are significantly improved. The reason for this may be that the compound of the present application is connected to a smaller aromatic group at the 5-position of the phenyl group of aniline, maintaining a higher coverage of the molecular HOMO orbital.

[0212] Compared with compound C, the aryl substituent in the compound of the present application is connected to the para position rather than the ortho position of the dibenzofuran / dibenzothiophene group in aniline, which enables the dibenzofuran / dibenzothiophene group to better maintain a high coincidence rate of intermolecular orbitals through space conjugation effect.

[0213] In the embodiment of the present application, compared with Comparative Example 4, while the driving voltage is close, the luminous efficiency and lifetime characteristics are significantly improved. The reason may be that compared with compound D, the aryl substituent in the compound of the present application is connected to the 5th position of aniline, thus maintaining a relatively deep HOMO energy level and a high T1 energy level.

[0214] Those skilled in the art will readily conceive of other embodiments of the present application after considering the specification and practicing the invention disclosed herein. The present application aims to cover any variations, uses or adaptations of the present application, which follow the general principles of the present application and include the common knowledge or conventional technical means in the technical field not disclosed in the present application. The specification and examples are only regarded as exemplary, and the true scope and spirit of the present application are pointed out by the following claims.

[0215] It should be understood that the present application is not limited to the exact structures already described 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 compound, characterized in that The organic compound has a structure as shown in Formula 1: Wherein, X is O or S; 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, or a substituted or unsubstituted biphenylene group; 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; 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 carbazolyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted spirobifluorenyl; 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; L3 is selected from a single bond, a substituted or unsubstituted phenylene group; 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; Ar3 is selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted phenanthrenyl; 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 pentadeuterated phenyl; And the organic compound is not the following compound:

2. The organic compound according to claim 1, characterized in that are independently selected from the group consisting of:

3. The organic compound according to claim 1, characterized in that Selected from the group consisting of:

4. The organic compound according to claim 1, characterized in that In formula 1 Selected from the group consisting of:

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

6. 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 any one of claims 1 to 5.

7. The organic electroluminescent device according to claim 6, characterized in that: The functional layer includes a hole assisting layer; and the hole assisting layer includes the organic compound.

8. The organic electroluminescent device according to claim 6, characterized in that: The organic electroluminescent device is a red organic electroluminescent device.

9. An electronic device, characterized in that The organic electroluminescent device comprises the organic electroluminescent device according to any one of claims 6 to 8.

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