Organic compounds, electronic components and electronic devices
By using organic compounds containing phenylenzozolazol/thiazole parent core structures connected to triazine compounds as electron-transporting red light host materials, the shortcomings in life and efficiency of existing organic electroluminescent devices are solved, and the Higher luminous efficiency and longer lifespan.
Patent Information
- Application Number
- CN202310973289.4
- Authority / Receiving Office
- CN · China
- Patent Type
- Patents(China)
- Current Assignee / Owner
- Filing Date
- 2023-08-03
- Publication Date
- 2025-02-11
- Estimated Expiration
- 2043-08-03
AI Technical Summary
The existing organic electroluminescent devices have shortcomings in terms of life and efficiency, especially when the driving voltage is increased, the luminous efficiency and current efficiency need to be further improved.
It provides an organic compound containing a phenanthobenzoxazole/thiazole parent core structure connected to a triazine compound, which is used as an electron-transporting red light host material, improves carrier equilibrium in the luminescent layer, and broadens the carrier composite region. , improve exciton generation and utilization efficiency.
By using this organic compound, the luminescence efficiency and lifetime of the organic electroluminescent device can be improved, and the luminescence efficiency of at least 10.0% and the T95 lifetime of 12.1% can be improved.
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Figure CN117430594B_ABST
Abstract
Description
Technical Field
[0001] The present application relates to the technical field of organic electroluminescent materials, and in particular to an organic compound, an electronic component and an electronic device. Background Art
[0002] Organic electroluminescent devices, such as organic light-emitting diodes (OLEDs), 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 organic light-emitting layer, a hole transport layer, an electron transport layer, etc. When a voltage is applied to the positive and negative electrodes, the two electrodes generate an electric field. Under the action of the electric field, the electrons on the cathode side move toward the electroluminescent layer, and the holes on the anode side also move toward the light-emitting layer. The electrons and holes combine in the electroluminescent layer to form excitons, and the excitons are in an excited state and release energy outward, thereby causing the electroluminescent layer to emit light outward.
[0003] The main problems of existing organic electroluminescent devices are lifespan and efficiency. As the display area becomes larger, the driving voltage also increases, and the luminous efficiency and current efficiency also need to be improved. Therefore, it is necessary to continue to develop new materials to further improve the performance of organic electroluminescent devices. Summary of the invention
[0004] In view of the above problems existing in the prior art, the purpose of the present application is to provide an organic compound and an organic electroluminescent device and an electronic device containing the same. The organic compound is used in an organic electroluminescent device to improve the performance of the device.
[0005] The first aspect of the present application provides an organic compound having a structure shown in Formula 1:
[0006]
[0007] Wherein, one of X and Y is -O- or -S-, and the other is -N=;
[0008] Each R 1 , R 2 , R 3 and R 4 are the same or different and are independently selected from hydrogen, deuterium, cyano, halogen, alkyl having 1 to 10 carbon atoms, halogenated alkyl having 1 to 10 carbon atoms, deuterated alkyl having 1 to 10 carbon atoms, aryl having 6 to 20 carbon atoms, deuterated aryl having 6 to 20 carbon atoms, heteroaryl having 3 to 20 carbon atoms, cycloalkyl having 3 to 10 carbon atoms or a group represented by Formula 2, and each R 1 , R 2 , R 3 and R 4There is only one group represented by Formula 2;
[0009]
[0010] n1 is R 1 The number of R is selected from 0, 1 or 2; when n1 is greater than 1, any two R 1 Same or different;
[0011] n2 is R 2 The number of R is selected from 0, 1 or 2; when n2 is greater than 1, any two R 2 Same or different;
[0012] n3 is R 3 The number of R is selected from 0, 1, 2, 3 or 4; when n3 is greater than 1, any two R 3 Same or different;
[0013] n4 is R 4 The number of R is selected from 0, 1 or 2; when n4 is greater than 1, any two R 4 Same or different;
[0014] L, L 1 and L 2 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;
[0015] Ar 1 ,Ar 2 and Ar 3 are the same or different and are each independently selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms and a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms;
[0016] L, L 1 , L 2 ,Ar 1 ,Ar 2 and Ar 3 The substituents in are the same or different and are independently selected from deuterium, cyano, halogen groups, alkyl groups having 1 to 10 carbon atoms, haloalkyl groups having 1 to 10 carbon atoms, deuterated alkyl groups having 1 to 10 carbon atoms, aryl groups having 6 to 20 carbon atoms, deuterated aryl groups having 6 to 20 carbon atoms, heteroaryl groups having 3 to 20 carbon atoms, cycloalkyl groups having 3 to 10 carbon atoms, and trialkylsilyl groups having 3 to 12 carbon atoms;
[0017] Optionally, Ar 1 ,Ar 2 and Ar 3Any two adjacent substituents form a saturated or unsaturated 5-15 membered ring.
[0018] The second aspect of the present application provides an organic electroluminescent device, comprising an anode and a cathode arranged opposite to each other, and a functional layer arranged between the anode and the cathode; the functional layer comprises the above-mentioned organic compound.
[0019] The third aspect of the present application provides an electronic device, comprising the organic electroluminescent device described in the second aspect.
[0020] The compound structure of the present application contains a parent core structure of phenanthrobenzoxazole / thiazole, and the parent core is connected to a triazine compound, which is used as an electron-transmitting red light host material. Among them, phenanthrobenzoxazole / thiazole has a large conjugated system, and after connecting it with triazine, it can enhance the intermolecular force and improve the compound carrier mobility. When the compound of the present application is used as an electron-transmitting material in a hybrid host material, the carrier balance in the light-emitting layer can be improved, the carrier recombination area can be widened, the exciton generation and utilization efficiency can be improved, and the device luminous efficiency and life can be improved. BRIEF DESCRIPTION OF THE DRAWINGS
[0021] The accompanying drawings are used to provide further understanding of the present application and constitute a part of the specification. Together with the following specific embodiments, they are used to explain the present application, but do not constitute a limitation to the present application.
[0022] Figure 1 It is a schematic diagram of the structure of an organic electroluminescent device according to one embodiment of the present application.
[0023] Figure 2 It is a schematic diagram of the structure of an electronic device according to an embodiment of the present application.
[0024] Reference numerals
[0025] 100, anode; 200, cathode; 300, functional layer; 310, hole injection layer;
[0026] 321, hole transport layer; 322, hole adjustment layer; 330, organic light emitting layer; 340, electron transport layer;
[0027] 350. Electron injection layer; 400. Electronic device DETAILED DESCRIPTION
[0028] Exemplary embodiments will now be described more fully with reference to the accompanying drawings. However, exemplary embodiments can be implemented in a variety of forms and should not be construed as being limited to the examples set forth herein; rather, these embodiments are provided so that the present application will be more comprehensive and complete and the concepts of the exemplary embodiments will be fully conveyed to those skilled in the art. The described features, structures, or characteristics may be combined in any suitable manner in one or more embodiments. In the following description, many specific details are provided to provide a full understanding of the embodiments of the present application.
[0029] In a first aspect, the present application provides an organic compound having a structure shown in the following formula 1:
[0030]
[0031] Wherein, one of X and Y is -O- or -S-, and the other is -N=;
[0032] Each R 1 , R 2 , R 3 and R 4 are the same or different and are independently selected from hydrogen, deuterium, cyano, halogen, alkyl having 1 to 10 carbon atoms, halogenated alkyl having 1 to 10 carbon atoms, deuterated alkyl having 1 to 10 carbon atoms, aryl having 6 to 20 carbon atoms, deuterated aryl having 6 to 20 carbon atoms, heteroaryl having 3 to 20 carbon atoms, cycloalkyl having 3 to 10 carbon atoms or a group represented by Formula 2, and each R 1 , R 2 , R 3 and R 4 There is only one group represented by Formula 2;
[0033]
[0034] n1 is R 1 The number of R is selected from 0, 1 or 2; when n1 is greater than 1, any two R 1 Same or different;
[0035] n2 is R 2 The number of R is selected from 0, 1 or 2; when n2 is greater than 1, any two R 2 Same or different;
[0036] n3 is R 3 The number of R is selected from 0, 1, 2, 3 or 4; when n3 is greater than 1, any two R 3 Same or different;
[0037] n4 is R 4The number of R is selected from 0, 1 or 2; when n4 is greater than 1, any two R 4 Same or different;
[0038] L, L 1 and L 2 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;
[0039] Ar 1 ,Ar 2 and Ar 3 are the same or different and are each independently selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms and a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms;
[0040] L, L 1 , L 2 ,Ar 1 ,Ar 2 and Ar 3 The substituents in are the same or different and are independently selected from deuterium, cyano, halogen groups, alkyl groups having 1 to 10 carbon atoms, haloalkyl groups having 1 to 10 carbon atoms, deuterated alkyl groups having 1 to 10 carbon atoms, aryl groups having 6 to 20 carbon atoms, deuterated aryl groups having 6 to 20 carbon atoms, heteroaryl groups having 3 to 20 carbon atoms, cycloalkyl groups having 3 to 10 carbon atoms, and trialkylsilyl groups having 3 to 12 carbon atoms;
[0041] Optionally, Ar 1 ,Ar 2 and Ar 3 Any two adjacent substituents form a saturated or unsaturated 5-15 membered ring.
[0042] In Formula I Part is a heteroaryl group, for example, when X is O or S, Y is -N=, the structure represents Or, when Y is O or S, X is -N=, the structures are respectively represented as
[0043] In the present application, the terms "optionally" and "optionally" mean that the event or environment described subsequently may or may not occur. For example, "optionally, any two adjacent substituents form a ring" means that the two substituents may or may not form a ring, that is, including: the scenario where two adjacent substituents form a ring and the scenario where two adjacent substituents do not form a ring. For another example, "optionally, any two adjacent substituents form a ring" means that any two adjacent substituents are connected to each other to form a ring, or any two adjacent substituents may also exist independently. "Any two adjacent" may include two substituents on the same atom, and may also include two adjacent atoms each having a substituent; wherein, when there are two substituents on the same atom, the two substituents may form a saturated or unsaturated spiro ring with the atom to which they are commonly connected; when there is a substituent on each of two adjacent atoms, the two substituents may be fused into a ring.
[0044] In the present application, a saturated or unsaturated 5-15 membered ring refers to a carbon ring or heterocyclic ring containing 5-15 ring atoms; for example, but not limited to, cyclopentane, cyclohexane, benzene ring, fluorene ring, pyran ring, tetrahydropyran ring, piperidine ring, tetrahydropiperidine ring, etc.
[0045] In the present application, the cycloalkyl group having 5 to 10 carbon atoms refers to a cycloalkyl group formed by 5 to 10 carbon atoms, such as but not limited to cyclopentyl, cyclohexyl, adamantyl and the like.
[0046] In the present application, a 6- to 15-membered unsaturated ring refers to an unsaturated ring formed by 6 to 15 ring atoms, such as but not limited to a benzene ring, a fluorene ring, a furan ring, a pyran ring, and the like.
[0047] In this application, the descriptions "each ... independently is" and "each ... independently is" and "... independently is" are interchangeable and should be understood in a broad sense, which can mean that in different groups, the specific options expressed by the same symbols do not affect each other, or in the same group, the specific options expressed by the same symbols do not affect each other. For example, Wherein, each q is independently 0, 1, 2 or 3, and each R" is independently selected from hydrogen, deuterium, fluorine, and chlorine, which means: Formula Q-1 indicates that there are q substituents R" on the benzene ring, and each R" can be the same or different, and the options of each R" do not affect each other; Formula Q-2 indicates that there are q substituents R" on each benzene ring of biphenyl, and the number q of R" substituents on the two benzene rings can be the same or different, and each R" can be the same or different, and the options of each R" do not affect each other.
[0048] In the present application, the term "substituted or unsubstituted" means that the functional group recorded after the term may or may not have a substituent (hereinafter, for the convenience of description, the substituents are collectively referred to as Rc). For example, "substituted or unsubstituted aryl" refers to an aryl group having a substituent Rc or an unsubstituted aryl group. The above-mentioned substituent, i.e., Rc, can be, for example, deuterium, a halogen group, a cyano group, a heteroaryl group, an aryl group, an alkyl group, a haloalkyl group, a deuterated alkyl group, a deuterated aryl group, a haloaryl group, a cycloalkyl group, etc. The number of substitutions can be 1 or more.
[0049] In the present application, "plurality" means more than 2, for example, 2, 3, 4, 5, 6, etc.
[0050] The hydrogen atoms in the structures of the compounds of the present application include various isotope atoms of the hydrogen element, such as hydrogen (H), deuterium (D) or tritium (T).
[0051] In the present application, the number of carbon atoms of a substituted or unsubstituted functional group refers to the total number of carbon atoms. For example, if L is a substituted arylene group having 12 carbon atoms, the total number of carbon atoms of the arylene group and the substituents thereon is 12.
[0052] In the present application, aryl refers to an optional functional group or substituent derived from an aromatic carbocyclic ring. Aryl can be a monocyclic aryl (e.g., phenyl) or a polycyclic aryl. In other words, aryl can be a monocyclic aryl, a condensed ring aryl, two or more monocyclic aryl connected by carbon-carbon single bond conjugation, a monocyclic aryl and a condensed ring aryl connected by carbon-carbon single bond conjugation, two or more condensed ring aryl connected by carbon-carbon single bond conjugation. That is, unless otherwise specified, two or more aromatic groups connected by carbon-carbon single bond conjugation can also be regarded as aryl of the present application. Wherein, condensed ring aryl can, for example, include bicyclic condensed aryl (e.g., naphthyl), tricyclic condensed aryl (e.g., phenanthrenyl, fluorenyl, anthracenyl), etc. Aryl does not contain heteroatoms such as B, N, O, S, P, Se, and Si. Examples of aryl groups may include, but are not limited to, phenyl, naphthyl, fluorenyl, phenyl-naphthyl, spirobifluorenyl, anthracenyl, phenanthrenyl, biphenyl, terphenyl, triphenylene, peryl, benzo[9,10]phenanthrenyl, pyrenyl, benzofluoranthenyl, Ji et al.
[0053] In the present application, the arylene group refers to a divalent or multivalent group formed by further losing one or more hydrogen atoms from an aryl group.
[0054] In the present application, terphenyl includes
[0055] In the present application, the number of carbon atoms of a substituted aryl group refers to the total number of carbon atoms of the aryl group and the substituents on the aryl group. For example, a substituted aryl group with 18 carbon atoms refers to the total number of carbon atoms of the aryl group and the substituents is 18.
[0056] In the present application, the carbon number of the substituted or unsubstituted aryl (arylene) can be 6, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29 or 30, etc. In some embodiments, the substituted or unsubstituted aryl is a substituted or unsubstituted aryl having 6 to 30 carbon atoms, in other embodiments, the substituted or unsubstituted aryl is a substituted or unsubstituted aryl having 6 to 20 carbon atoms, in other embodiments, the substituted or unsubstituted aryl is a substituted or unsubstituted aryl having 6 to 25 carbon atoms, in other embodiments, the substituted or unsubstituted aryl is a substituted or unsubstituted aryl having 6 to 18 carbon atoms, and in other embodiments, the substituted or unsubstituted aryl is a substituted or unsubstituted aryl having 6 to 15 carbon atoms.
[0057] In the present application, the fluorenyl group may be substituted by one or more substituents. In the case where the above fluorenyl group is substituted, the substituted fluorenyl group may be: Etc., etc., but not limited to these.
[0058] In this application, L, L 1 , L 2 ,Ar 1 ,Ar 2 and Ar 3 The aryl substituents in the group include, but are not limited to, phenyl, naphthyl, phenanthrenyl, biphenyl, fluorenyl, and the like.
[0059] In the present application, heteroaryl refers to a monovalent aromatic ring or a derivative thereof containing 1, 2, 3, 4, 5 or 6 heteroatoms in the ring, and the heteroatoms may be one or more of B, O, N, P, Si, Se and S. The heteroaryl may be a monocyclic heteroaryl or a polycyclic heteroaryl, in other words, the heteroaryl may be a single aromatic ring system or a plurality of aromatic ring systems conjugated by carbon-carbon single bonds, and any aromatic ring system may be an aromatic monocyclic ring or an aromatic condensed ring. By way of example, the heteroaryl group may include a thienyl group, a furyl group, a pyrrolyl group, an imidazolyl group, a thiazolyl group, an oxazolyl group, an oxadiazolyl group, a triazolyl group, a pyridyl group, a bipyridyl group, a pyrimidyl group, a triazine group, an acridinyl group, a pyridazinyl group, a pyrazinyl group, a quinolyl group, a quinazolinyl group, a quinoxalinyl group, a phenoxazinyl group, a phthalazinyl group, a pyridopyrimidinyl group, a pyridopyrazinyl group, a pyrazinopyrazinyl group, an isoquinolyl group, an indolyl group, a carbazolyl group, a benzoxazolyl group, a benzimidazolyl group, a benzothiazolyl group, a benzocarbazolyl group, a benzothienyl group, a dibenzothienyl group, a thienothiphenyl group, a benzofuranyl group, a phenanthrolinyl group, an isoxazolyl group, a thiadiazolyl group, a phenothiazinyl group, a silyfluorenyl group, a dibenzofuranyl group, and an N-phenylcarbazolyl group, an N-pyridylcarbazolyl group, an N-methylcarbazolyl group, and the like, without being limited thereto.
[0060] In the present application, the heteroarylene group refers to a divalent or multivalent group formed by further losing one or more hydrogen atoms from a heteroaryl group.
[0061] In the present application, the number of carbon atoms of the substituted or unsubstituted heteroaryl (heteroarylene) can be selected from 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 or 30, etc. In some embodiments, the substituted or unsubstituted heteroaryl is a substituted or unsubstituted heteroaryl with a total carbon number of 3 to 18, in other embodiments, the substituted or unsubstituted heteroaryl is a substituted or unsubstituted heteroaryl with a total carbon number of 3 to 12, and in other embodiments, the substituted or unsubstituted heteroaryl is a substituted or unsubstituted heteroaryl with a total carbon number of 5 to 12. In the present application, the heteroaryl group as a substituent in L, L1, L2, Ar1, Ar2 and Ar3 is exemplified but not limited to pyridyl, carbazolyl, quinolyl, isoquinolyl, phenanthroline, benzoxazolyl, benzothiazolyl, benzimidazolyl, dibenzothiophenyl and dibenzofuranyl.
[0062] In the present application, the substituted heteroaryl group may be a heteroaryl group in which one or more hydrogen atoms are replaced by groups such as deuterium atoms, halogen groups, -CN, aryl groups, heteroaryl groups, trialkylsilyl groups, alkyl groups, cycloalkyl groups, haloalkyl groups, etc. It should be understood that the number of carbon atoms in the substituted heteroaryl group refers to the total number of carbon atoms in the heteroaryl group and the substituents on the heteroaryl group.
[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 is, for example, 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10, and specific examples of the alkyl group include, but are not limited to, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl, neopentyl, n-hexyl, and the like.
[0064] In the present application, the halogen group is, for example, fluorine, chlorine, bromine, or iodine.
[0065] In the present application, specific examples of trialkylsilyl include, but are not limited to, trimethylsilyl, triethylsilyl, and the like.
[0066] In the present application, specific examples of the haloalkyl group include, but are not limited to, trifluoromethyl.
[0067] In the present application, specific examples of deuterated alkyl groups include, but are not limited to, trideuterated methyl groups.
[0068] In the present application, a deuterated aryl group refers to an aryl group containing deuterium, such as but not limited to pentadeuterated phenyl, heptadeuterated naphthyl, deuterated biphenyl and the like.
[0069] In the present application, the halogenated aryl group refers to an aryl group with a halogen substituent, such as but not limited to fluorophenyl, fluoronaphthyl, fluorobiphenyl and the like.
[0070] In the present application, the carbon number of the cycloalkyl group having 3 to 10 carbon atoms is, for example, 3, 4, 5, 6, 7, 8 or 10. Specific examples of the cycloalkyl group include, but are not limited to, cyclopentyl, cyclohexyl, and adamantyl.
[0071] In this application, an unpositioned connecting bond refers to a single bond extending from the ring system. It means that one end of the connecting bond can be connected to any position in the ring system that the bond passes through, and the other end is connected to the rest of the compound molecule. For example, as shown in the following formula (f), the naphthyl represented by formula (f) is connected to other positions of the molecule through two non-positional connecting bonds that pass through the bicyclic ring. The meaning represented by it includes any possible connection mode shown in formula (f-1) to formula (f-10):
[0072]
[0073] For another example, as shown in the following formula (X'), the dibenzofuranyl represented by formula (X') is connected to other positions of the molecule through a non-positional connecting bond extending from the middle of one side of the benzene ring, and the meaning represented by it includes any possible connection mode shown in formula (X'-1) to formula (X'-4):
[0074]
[0075] The non-positioning substituent in the present application refers to a substituent connected by a single bond extending from the center of the ring system, which means that the substituent can be connected to any possible position in the ring system. For example, as shown in the following formula (Y), the substituent R' represented by formula (Y) is connected to the quinoline ring through a non-positioning connecting bond, and the meaning represented by it includes any possible connection mode shown in formula (Y-1) to formula (Y-7):
[0076]
[0077] In some embodiments, Formula 1 is selected from the following structures shown in Formula 1-1 or Formula 1-2:
[0078]
[0079] In some embodiments, R 1 One of them has the structure shown in Formula 2, when n1 is greater than 1, the other R 1 With each R 2 , R 3 and R4 Each is independently selected from hydrogen, deuterium, cyano, a halogen 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, an aryl group having 6 to 12 carbon atoms, a deuterated aryl group having 6 to 12 carbon atoms or a heteroaryl group having 5 to 12 carbon atoms.
[0080] In some embodiments, R 2 One of them has the structure shown in Formula 2, when n2 is greater than 1, the other R 2 With each R 1 , R 3 and R 4 Each is independently selected from hydrogen, deuterium, cyano, a halogen 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, an aryl group having 6 to 12 carbon atoms, a deuterated aryl group having 6 to 12 carbon atoms or a heteroaryl group having 5 to 12 carbon atoms.
[0081] In some embodiments, R 3 One of them has the structure shown in Formula 2, when n3 is greater than 1, the other R 3 With each R 1 , R 2 and R 4 Each is independently selected from hydrogen, deuterium, cyano, a halogen 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, an aryl group having 6 to 12 carbon atoms, a deuterated aryl group having 6 to 12 carbon atoms or a heteroaryl group having 5 to 12 carbon atoms.
[0082] In some embodiments, R 4 One of them has the structure shown in Formula 2, when n4 is greater than 1, the other R 4 With each R 1 , R 2 and R 3 Each is independently selected from hydrogen, deuterium, cyano, a halogen 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, an aryl group having 6 to 12 carbon atoms, a deuterated aryl group having 6 to 12 carbon atoms or a heteroaryl group having 5 to 12 carbon atoms.
[0083] In some embodiments, each R 1 , R 2 , R 3 and R 4 The same or different, and each R 1 , R 2 , R 3 and R 4There is only one group represented by Formula 2, and the others are independently selected from hydrogen, deuterium, cyano, fluorine, methyl, ethyl, isopropyl, tert-butyl or phenyl.
[0084] In some embodiments, Ar 1 ,Ar 2 and Ar 3 the same or different and each independently selected from a substituted or unsubstituted aryl group having 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24 or 25 carbon atoms and a substituted or unsubstituted heteroaryl group having 5, 6, 7, 8, 9, 10, 12, 13, 14, 15, 16, 17 or 18 carbon atoms.
[0085] In some embodiments, Ar 1 ,Ar 2 and Ar 3 are the same or different and are each independently selected from a substituted or unsubstituted aryl group having 6 to 25 carbon atoms and a substituted or unsubstituted heteroaryl group having 5 to 18 carbon atoms.
[0086] Optionally, Ar 1 ,Ar 2 and Ar 3 The substituents in are the same or different and are independently selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 4 carbon atoms, a deuterated alkyl group having 1 to 4 carbon atoms, a trialkylsilyl group having 3 to 7 carbon atoms, a naphthyl group, a phenyl group or a pentadeuterated phenyl group;
[0087] Optionally, Ar 1 ,Ar 2 and Ar 3 Any two adjacent substituents form a fluorene ring.
[0088] Further optionally, Ar 3 It is selected from a substituted or unsubstituted aryl group having 6 to 15 carbon atoms and a substituted or unsubstituted heteroaryl group having 12 to 18 carbon atoms.
[0089] In some embodiments, Ar 1 ,Ar 2 and Ar 3 the same or different, and each independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted fluorenyl, substituted or unsubstituted spirobifluorenyl, substituted or unsubstituted triphenylene, substituted or unsubstituted pyridyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted carbazolyl.
[0090] Optionally, Ar 1 ,Ar 2 and Ar 3 The substituents in are the same or different and are independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trimethylsilyl, phenyl, naphthyl or pentadeuterated phenyl.
[0091] Further optionally, Ar 3 is selected from substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted dibenzofuranyl, and substituted or unsubstituted dibenzothienyl.
[0092] In some embodiments, Ar 1 and Ar 2 Each is independently selected from a substituted or unsubstituted group W; wherein the unsubstituted group W is selected from the group consisting of the following groups:
[0093]
[0094] The substituted group W has one or more substituents, and the substituents on the substituted group W are each independently selected from deuterium, fluorine, cyanomethyl, ethyl, isopropyl, tert-butyl or phenyl, and when the number of substituents on the group W is greater than 1, each substituent is the same or different.
[0095] In some embodiments, Ar 1 and Ar 2 The same or different, and each independently selected from the group consisting of the following groups:
[0096]
[0097]
[0098] In some embodiments, Ar 1 and Ar 2 The same or different, and each independently selected from the group consisting of the following groups:
[0099]
[0100] In some embodiments, Ar 3 is selected from a substituted or unsubstituted group Q; wherein the unsubstituted group Q is selected from the group consisting of the following groups:
[0101]
[0102] The substituted group Q has one or more substituents, and the substituents on the substituted group Q are each independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl or phenyl, and when the number of substituents on the group Q is greater than 1, the substituents are the same or different.
[0103] In some embodiments, Ar 3 Selected from the group consisting of:
[0104]
[0105] In some embodiments, Ar 3 Selected from the group consisting of:
[0106]
[0107] In some embodiments, L 1 , L 2 and L are the same as or different from each other and are each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 15 carbon atoms, and a substituted or unsubstituted heteroarylene group having 12 to 18 carbon atoms.
[0108] Optionally, L 1 , L 2 and L are the same as or different from each other and are each independently selected from a single bond and a substituted or unsubstituted arylene group having 6 to 12 carbon atoms.
[0109] In some embodiments, L 1 , L 2 and L are the same as or different from each other and are each independently selected from a single bond, a substituted or unsubstituted arylene group having 6, 7, 8, 9, 10, 11, 12, 13, 14 or 15 carbon atoms, and a substituted or unsubstituted heteroarylene group having 12, 13, 14, 15, 16, 17 or 18 carbon atoms.
[0110] In some embodiments, L 1 , L 2 The substituents in and L are each independently selected from deuterium, fluorine, cyano, an alkyl group having 1 to 5 carbon atoms, a trialkylsilyl group having 3 to 7 carbon atoms, or a phenyl group.
[0111] In some embodiments, L 1 , L 2 and L are the same as or different from each other, 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 fluorenylene group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted dibenzothienyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted carbazolyl group.
[0112] In some embodiments, L 1 , L 2 The substituents in L are the same as or different from each other and are each independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trimethylsilyl or phenyl.
[0113] Optionally, L is selected from a single bond, a substituted or unsubstituted phenylene group, and a substituted or unsubstituted naphthylene group.
[0114] In some embodiments, L is selected from the group consisting of a single bond or the following groups:
[0115]
[0116] In some embodiments, L 1 and L 2 Each is independently selected from the group consisting of a single bond or the following groups:
[0117]
[0118] In some specific embodiments, L 1 and L 2 Each is independently selected from the group consisting of a single bond or the following groups:
[0119]
[0120] In some specific embodiments, L is selected from a single bond or the group consisting of:
[0121]
[0122] In some embodiments, The same or different, and each independently selected from the group consisting of the following groups:
[0123]
[0124]
[0125] Specifically, The same or different, and each independently selected from the group consisting of the following groups:
[0126]
[0127]
[0128] In some embodiments, the group shown in Formula 2 Selected from the group consisting of:
[0129]
[0130]
[0131]
[0132] Specifically, the structure shown in Formula 2 Selected from the group consisting of:
[0133]
[0134]
[0135]
[0136]
[0137]
[0138] In some embodiments, the compound has a structure shown in Formula II-1 to II-16:
[0139]
[0140]
[0141] In some embodiments, the compound is selected from the group consisting of:
[0142]
[0143]
[0144]
[0145]
[0146]
[0147]
[0148]
[0149]
[0150] The second aspect of the present application provides an organic electroluminescent device, comprising an anode, a cathode, and a functional layer arranged between the anode and the cathode; wherein the functional layer comprises the organic compound described in the first aspect of the present application.
[0151] The compound provided in the present application can be used to form at least one organic film layer in the functional layer to improve the current efficiency, life span and other characteristics of the organic electroluminescent device.
[0152] Optionally, the functional layer includes an organic light-emitting layer, and the organic light-emitting layer includes the organic compound. The organic light-emitting layer can be composed of the organic compound provided in the present application, or can be composed of the organic compound provided in the present application and other materials.
[0153] According to a specific embodiment, the organic electroluminescent device is as follows Figure 1 As shown, the organic electroluminescent device may include an anode 100, a hole injection layer 310, a hole transport layer 321, a hole adjustment layer (also called a hole auxiliary layer, a second hole transport layer or an electron blocking layer) 322, an organic light-emitting layer 330, an electron transport layer 340, an electron injection layer 350 and a cathode 200 which are stacked in sequence.
[0154] In the present application, the anode 100 includes an anode material, which is preferably a material with a large work function that facilitates hole injection into the functional layer. Specific examples of anode materials include: metals such as nickel, platinum, vanadium, chromium, copper, zinc and gold or their alloys; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO) and indium zinc oxide (IZO); combined metals and oxides such as ZnO:Al or SnO2:Sb; or conductive polymers such as poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (PEDT), polypyrrole and polyaniline, but are not limited thereto. Preferably, a transparent electrode including indium tin oxide (ITO) as an anode is included.
[0155] In the present application, the hole transport layer may include one or more hole transport materials, and the hole transport layer material may be selected from carbazole polymers, carbazole-linked triarylamine compounds or other types of compounds, and may be specifically selected from the following compounds or any combination thereof:
[0156]
[0157]
[0158] In one embodiment, the hole transport layer 321 is composed of HT-5.
[0159] Optionally, the hole adjustment layer 322 may include one or more hole transport materials, and the hole transport material may be selected from carbazole polymers, carbazole-linked triarylamine compounds or other types of compounds, which are not specifically limited in the present application. For example, in some embodiments of the present application, the hole adjustment layer 330 is composed of HT-2.
[0160] In one embodiment, the hole-regulating layer 322 is composed of HT-2.
[0161] Optionally, a hole injection layer 310 is further provided between the anode 100 and the hole transport layer 321 to enhance the ability to inject holes into the hole transport layer 321. The hole injection layer 310 may be made of benzidine derivatives, starburst arylamine compounds, phthalocyanine derivatives or other materials, and the present application does not impose any particular limitation thereto. The material of the hole injection layer 310 is, for example, selected from the following compounds or any combination thereof;
[0162]
[0163] In one embodiment, the hole injection layer 310 is composed of PD and HT-5.
[0164] In the present application, the organic light-emitting layer 330 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 330 is composed of a host material and a guest material, and holes injected into the organic light-emitting layer 330 and electrons injected into the organic light-emitting layer 330 may be recombined in the organic light-emitting layer 330 to form excitons, and the excitons transfer energy to the host material, and the host material transfers energy to the guest material, thereby enabling the guest material to emit light.
[0165] The host material of the organic light-emitting layer 330 may include metal chelate compounds, bisphenylethylene derivatives, aromatic amine derivatives, dibenzofuran derivatives or other types of materials. Optionally, the host material includes the organic compound of the present application.
[0166] The guest material of the organic light-emitting layer 330 can be a compound having a condensed aromatic ring or a derivative thereof, a compound having a heteroaromatic ring or a derivative thereof, an aromatic amine derivative or other materials, and the present application does not impose any special restrictions on this. The guest material is also called a doping material or a dopant. According to the type of luminescence, it can be divided into a fluorescent dopant and a phosphorescent dopant. Specific examples of the phosphorescent dopant include, but are not limited to,
[0167]
[0168] In one embodiment of the present application, the organic electroluminescent device is a red organic electroluminescent device. In one embodiment, the host material of the organic light-emitting layer 330 comprises the organic compound of the present application. The guest material is, for example, RD. In another embodiment, the host material of the organic light-emitting layer 330 comprises the organic compound of the present application and The guest material is, for example, RD.
[0169] The electron transport layer 340 may be a single-layer structure or a multi-layer structure, and may include one or more electron transport materials, which may be selected from but not limited to BTB, LiQ, benzimidazole derivatives, oxadiazole derivatives, quinoxaline derivatives or other electron transport materials, and the present application does not make any special restrictions. The materials of the electron transport layer 340 include but are not limited to the following compounds:
[0170]
[0171]
[0172] In one embodiment of the present application, the electron transport layer 340 may be composed of ET-1 and LiQ.
[0173] In the present application, cathode 200 may include a cathode material, which is a material with a small work function that facilitates electron injection into the functional layer. Specific examples of cathode materials include, but are not limited to, metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead or their alloys; or multilayer materials such as LiF / Al, Liq / Al, LiO2 / Al, LiF / Ca, LiF / Al and BaF2 / Ca. Optionally, a metal electrode containing magnesium and silver is included as the cathode.
[0174] Optionally, an electron injection layer 350 is further provided between the cathode 200 and the electron transport layer 340 to enhance the ability to inject electrons into the electron transport layer 340. The electron injection layer 350 may include inorganic materials such as alkali metal sulfides and alkali metal halides, or may include a complex of an alkali metal and an organic substance. In one embodiment of the present application, the electron injection layer 350 may include ytterbium (Yb).
[0175] A third aspect of the present application provides an electronic device, comprising the organic electroluminescent device described in the second aspect of the present application.
[0176] According to one embodiment, Figure 2As shown, the provided electronic device is an electronic device 400, which includes the above-mentioned organic electroluminescent device. The electronic device 400 can be, for example, a display device, a lighting device, an optical communication device, or other types of electronic devices, such as but not limited to a computer screen, a mobile phone screen, a television, an electronic paper, an emergency lighting lamp, an optical module, etc.
[0177] The synthesis method of the organic compound of the present application is specifically described below in conjunction with synthesis examples, but the present disclosure is not limited thereby.
[0178] Synthesis Example
[0179] Those skilled in the art will recognize that the chemical reactions described herein can be used to appropriately prepare many of the organic compounds of the present invention, and that other methods for preparing the compounds of the present invention are considered to be within the scope of the present invention. For example, the synthesis of the compounds not exemplified herein can be successfully accomplished by those skilled in the art by modification methods, such as appropriate protection of interfering groups, by utilizing other known reagents in addition to those described herein, or by making some conventional modifications to the reaction conditions. The compounds of the synthetic methods not mentioned in the present invention are all raw materials obtained through commercial channels.
[0180] Synthesis of intermediates:
[0181] Synthesis of intermediate Sub-b1:
[0182]
[0183] Under nitrogen protection, add Sub-a1 (16.20 g, 50 mmol), 5-chloro-2-formylphenylboronic acid (CAS: 870238-36-1, 10.14 g, 55 mmol), tetrakis(triphenylphosphine)palladium (Pd(PPh3)4, 0.58 g, 0.5 mmol), anhydrous sodium carbonate (Na2CO3, 10.60 g, 100 mmol), toluene (PhMe, 160 mL), anhydrous ethanol (EtOH, 40 mL) and deionized water (40 mL) to a 500 mL three-necked flask in sequence, start stirring and heating, and heat to reflux for 8 h. After the system is cooled to room temperature, extract with dichloromethane (100 mL × 3 times), combine the organic phases and dry with anhydrous magnesium sulfate, filter and remove the solvent by reduced pressure distillation 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 Sub-b1 as a white solid (10.94 g, yield: 57%).
[0184] Referring to the synthesis of intermediate Sub-a1, reactant B shown in Table 1 was used instead of Sub-a1, and reactant C was used instead of 5-chloro-2-formylphenylboronic acid to synthesize intermediates Sub-b2 to Sub-b8.
[0185] Table 1: Synthesis of Intermediate Sub-b2 to Intermediate Sub-b8
[0186]
[0187] Synthesis of intermediate Sub-c1:
[0188]
[0189] Under nitrogen protection, add Sub-b1 (49.90g, 130mmol), (methoxymethyl) triphenylphosphonium chloride (74.38g, 217mmol) and anhydrous tetrahydrofuran (THF, 500mL) to a 1000mL three-necked flask in sequence, cool the system to 0℃ with an ice-water bath; then slowly drop a solution of potassium tert-butoxide (t-BuOK) in anhydrous tetrahydrofuran (1M, 220mL) to the system; after the addition is complete, let the system slowly warm up to room temperature and continue to stir and react for 6h. Pour the reaction solution into 1000mL deionized water, extract with ethyl acetate (250mL×3 times), combine the organic phases and dry with anhydrous magnesium sulfate, filter and remove the solvent by vacuum distillation to obtain a crude product. Purify the crude product by silica gel column chromatography using n-heptane as the mobile phase to obtain Sub-c1 as a white solid (39.10g, yield: 73%).
[0190] Referring to the intermediate Sub-c1, the reactant D shown in Table 2 was used instead of Sub-b1 to synthesize the intermediates Sub-c2 to Sub-c8.
[0191] Table 2: Synthesis of Intermediate Sub-c2 to Intermediate Sub-c8
[0192]
[0193]
[0194] Synthesis of intermediate Sub-d1:
[0195]
[0196] Under nitrogen protection, add Sub-c1 (49.00 g, 119 mmol), Eaton's reagent (4.5 mL) and chlorobenzene (500 mL) to a 1000 mL three-necked flask in sequence, raise the temperature to reflux and continue stirring the reaction for 4 hours. When the reaction system reaches room temperature, pour the reaction solution into 1000 ml of deionized water, neutralize with saturated sodium hydroxide solution, and then extract with dichloromethane (250 mL × 3 times), combine the organic phases and dry with anhydrous magnesium sulfate, filter and remove the solvent by vacuum distillation to obtain a crude product. Use dichloromethane / n-heptane as the mobile phase to purify the crude product by silica gel column chromatography to obtain Sub-d1 solid (21.70 g, yield: 48%).
[0197] Referring to the synthesis of intermediate Sub-d1, reactant E shown in Table 3 was used instead of Sub-c1 to synthesize intermediates Sub-d2 to Sub-d8.
[0198] Table 3: Synthesis of Intermediate Sub-d2 to Intermediate Sub-d8
[0199]
[0200]
[0201] Synthesis of intermediate Sub-e1:
[0202]
[0203] Under nitrogen protection, Sub-d1 (19.00 g, 50 mmol), diboric acid pinacol ester (CAS: 73183-34-3, 14.00 g, 55 mmol), potassium acetate (KOAc, 10.80 g, 110 mmol) and 1,4-dioxane (160 mL) were added to a 500 mL three-necked flask in sequence, stirring and heating were started, and when the system was heated to 40 ° C, tris(dibenzylideneacetone)dipalladium (Pd2(dba)3, 0.46 g, 0.50 mmol) and 2-dicyclohexylphosphine-2',4',6'triisopropylbiphenyl (XPhos, 0.48 g, 1.0 mmol) were quickly added, and the temperature was continued to rise to reflux, and the reaction was stirred overnight. After the system was cooled to room temperature, 200 mL of water was added to the system, and the mixture was stirred for 30 min. The mixture was filtered under reduced pressure. The filter cake was washed with deionized water until neutral, and then rinsed with 100 mL of anhydrous ethanol to obtain a gray solid. The crude product was slurried once with n-heptane, dissolved with 200 mL of toluene, and then passed through a silica gel column to remove the catalyst. After concentration, Sub-e1 was obtained as a white solid (15.79 g, yield: 67%).
[0204] Referring to the synthesis of intermediate Sub-e1, reactant F shown in Table 4 was used instead of Sub-d1 to synthesize intermediates Sub-e2 to Sub-e7.
[0205] Table 4: Synthesis of Intermediate Sub-e2 to Intermediate Sub-e7
[0206]
[0207]
[0208] Synthesis of compounds
[0209] Synthesis of compound 4:
[0210]
[0211] Under nitrogen protection, add Sub-e1 (11.78g, 25mmol), RM-1 (8.95g, 25mmol), tetrakis(triphenylphosphine)palladium (Pd(PP3)4, 0.29g, 0.25mmol), anhydrous potassium carbonate (K2CO3, .9g, 50mmol), tetrabutylammonium bromide (0.8g, 2.5mmol), toluene (120mL), tetrahydrofuran (30mL) and deionized water (30mL) to a 250mL three-necked flask in sequence, start stirring and heating, and heat to reflux for 16h. After the system is cooled to room temperature, extract with dichloromethane (100mL×3 times), combine the organic phases and dry with anhydrous magnesium sulfate, filter and remove the solvent by reduced pressure distillation 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 compound 4 as a white solid (10.50 g, yield: 63%, m / z = 667.32 [M+H] + ).
[0212] Referring to the synthesis of compound 4, reactant G shown in Table 5 was used to replace Sub-e1, and reactant H was used to replace RM-1 to synthesize the compounds of the present application in Table 6.
[0213] Table 5: Synthesis of compounds of the present application
[0214]
[0215]
[0216]
[0217]
[0218]
[0219] Characterization of compounds
[0220] The NMR data of some compounds are as follows:
[0221] Compound 69: 1 H-NMR(400MHz,Methylene-Chloride-D2)δppm 9.51(s,1H),9.21(d,1H),8.83(s,1H),8.81(s,1H),8.69(d,1H),8.61( d,1H),8.53(d,1H),8.34-8.30(m,3H),8.25(d,1H),8.18(d,1H),8.13( d,1H),8.08(d,1H),8.05-7.98(m,3H),7.93(d,1H),7.81(d,1H),7.76( d,1H),7.64(t,1H),7.57(t,2H),7.52-7.47(m,2H),7.40-7.32(m,3H).
[0222] Preparation and evaluation of organic electroluminescent devices:
[0223] The organic electroluminescent device of the present application is described in detail below through examples. However, the following examples are only examples of the present application, and do not limit the present application:
[0224] Example 1: Red organic electroluminescent device
[0225] First, the anode pretreatment is carried out through the following process: the thickness is On the ITO / Ag / ITO substrate, the surface is treated with UV ozone and O2:N2 plasma to increase the work function of the anode. The surface of the ITO substrate can also be cleaned with an organic solvent to remove impurities and oil stains on the surface of the ITO substrate.
[0226] On the experimental substrate (anode), PD:HT-5 was co-evaporated at an evaporation rate ratio of 2%:98% to form a film with a thickness of Then, HT-5 was vacuum-deposited on the hole injection layer to form a hole injection layer with a thickness of hole transport layer.
[0227] Compound HT-2 is vacuum-deposited on the hole transport layer to form a layer with a thickness of Holes adjustment layer.
[0228] On the hole adjustment layer, compound 4:RH-P:RD was co-deposited at a specific deposition rate ratio of 49%:49%:2% to form a layer with a thickness of of an organic light-emitting layer (EML).
[0229] On the organic light-emitting layer, compound ET-1 and LiQ are co-evaporated at an evaporation rate ratio of 1:1 to form a layer with a thickness of The electron transport layer (ETL) is formed by evaporating Yb on the electron transport layer to form a layer with a thickness of Then, magnesium (Mg) and silver (Ag) were mixed at a evaporation rate of 1:9 and vacuum evaporated on the electron injection layer to form a layer with a thickness of cathode.
[0230] In addition, compound CP-1 is vacuum-evaporated on the cathode to form a layer with a thickness of The cover layer (CPL) is formed on the substrate, thereby completing the manufacture of the red organic electroluminescent device.
[0231] Embodiments 2 to 33
[0232] An organic electroluminescent device was prepared by the same method as in Example 1, except that the compound shown in Table 6 below was used instead of Compound 4 in Example 1 when preparing the light-emitting layer.
[0233] Comparative Examples 1 to 3
[0234] An organic electroluminescent device was prepared by the same method as in Example 1, except that compound A, compound B and compound C were used to replace compound 4 in Example 1 when preparing the light-emitting layer.
[0235] Among them, when preparing each embodiment and comparative example, the compound structure used is as follows:
[0236]
[0237] The performance of the red organic electroluminescent devices prepared in Examples 1-33 and Comparative Examples 1-3 was tested. Specifically, at 10 mA / cm 2 The IVL performance of the device was tested under the conditions of T95 device life at 20mA / cm 2 The test was carried out under the conditions of , and the test results are shown in Table 6.
[0238] Table 6
[0239]
[0240]
[0241] Referring to Table 6 above, it can be seen that, compared with Comparative Examples 1 to 3, when the compound of the present application is used as the host material of the red organic electroluminescent device, the luminous efficiency of the device is increased by at least 10.0%, and the T95 life is increased by at least 12.1%.
[0242] The present application has found that the structure of the compound of the present application contains a parent core structure of phenanthrobenzoxazole / thiazole, and the parent core is connected to a triazine compound, which is used as an electron-transmitting red light host material. Among them, phenanthrobenzoxazole / thiazole has a large conjugated system, and after connecting it with triazine, it can enhance the intermolecular force and improve the compound carrier mobility. When the compound of the present application is used as an electron-transmitting material in a hybrid host material, the carrier balance in the light-emitting layer can be improved, the carrier recombination area can be widened, the exciton generation and utilization efficiency can be improved, and the device luminous efficiency and life can be improved.
[0243] Those skilled in the art will readily appreciate other embodiments of the present application after considering the specification and practicing the invention disclosed herein. The present application is intended to cover any modification, use or adaptation of the present application, which follows the general principles of the present application and includes common knowledge or customary technical means in the art that are not disclosed in the present application.
Claims
1. An organic compound, characterized in that The organic compound has a structure shown in Formula 1: Wherein, one of X and Y is -O- or -S-, and the other is -N=; n1 is R 1 The number of R is selected from 0, 1 or 2; when n1 is greater than 1, any two R 1 Same or different; n2 is R 2 The number of R is selected from 0, 1 or 2; when n2 is greater than 1, any two R 2 Same or different; n3 is R 3 The number of is selected from 1, 2, 3 or 4; When n3 is 1, R 3 Having the structure shown in Formula 2, each R 1 , R 2 and R 4 Each is independently selected from deuterium, cyano, halogen, alkyl having 1 to 4 carbon atoms, deuterated alkyl having 1 to 4 carbon atoms, haloalkyl having 1 to 4 carbon atoms, aryl having 6 to 12 carbon atoms, deuterated aryl having 6 to 12 carbon atoms or heteroaryl having 5 to 12 carbon atoms; When n3 is greater than 1, R 3 One of them has the structure shown in Formula 2, and the other R 3 With each R 1 , R 2 and R 4 Each is independently selected from deuterium, cyano, halogen, alkyl having 1 to 4 carbon atoms, deuterated alkyl having 1 to 4 carbon atoms, haloalkyl having 1 to 4 carbon atoms, aryl having 6 to 12 carbon atoms, deuterated aryl having 6 to 12 carbon atoms or heteroaryl having 5 to 12 carbon atoms; n4 is R 4 The number of R is selected from 0, 1 or 2; when n4 is greater than 1, any two R 4 Same or different; Ar 1 ,Ar 2 are the same or different, and are each independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted fluorenyl, substituted or unsubstituted spirobifluorenyl, substituted or unsubstituted triphenylene, substituted or unsubstituted dibenzothienyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted carbazolyl; Ar 3 is selected from substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted dibenzothienyl, substituted or unsubstituted dibenzofuranyl; Ar 1 ,Ar 2 and Ar 3 The substituents in are the same or different and are independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, phenyl, naphthyl or pentadeuterated phenyl; L is selected from a single bond, a substituted or unsubstituted phenylene group, and a substituted or unsubstituted naphthylene group; L 1 , L 2 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, and a substituted or unsubstituted biphenylene group; L 1 , L 2 The substituents in L are the same as or different from each other and are each independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl or phenyl.
2. The organic compound according to claim 1, characterized in that When n3 is greater than 1, the remaining R 3 With each R 1 , R 2 and R 4 Each is independently selected from deuterium, cyano, fluorine, methyl, ethyl, isopropyl, tert-butyl or phenyl.
3. The organic compound according to claim 1, characterized in that n3 is 1.
4. The organic compound according to claim 1, characterized in that Ar 1 and Ar 2 The same or different, and each independently selected from the group consisting of the following groups: Ar 3 Selected from the group consisting of:
5. The organic compound according to claim 1, characterized in that L is selected from a single bond or the following groups: L 1 and L 2 are the same or different, each independently selected from the group consisting of a single bond or the following groups:
6. The organic compound according to claim 1, characterized in that The same or different, and each independently selected from the group consisting of the following groups:
7. The organic compound according to claim 1, characterized in that The structure shown in formula 2 Selected from the group consisting of:
8. The organic compound according to claim 1, characterized in that The compound is selected from the following structures:
9. An organic electroluminescent device, comprising an anode and a cathode disposed opposite to each other, and a functional layer disposed between the anode and the cathode; characterized in that: The functional layer includes an organic light-emitting layer, and the organic light-emitting layer includes the organic compound according to any one of claims 1 to 8.
10. An electronic device, characterized in that The organic electroluminescent device according to claim 9 is included.
Citation Information
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