Organic compound, organic electroluminescent device, and electronic apparatus
By using organic compounds with a phenanthrene-naphthofuran core structure as electron transport-type light-emitting host materials, the problems of high driving voltage, low luminous efficiency, and short lifetime in organic electroluminescent devices have been solved, thereby improving device performance.
Patent Information
- Application Number
- PCT/CN2025/089894
- Authority / Receiving Office
- WO · WO
- Patent Type
- Applications
- Current Assignee / Owner
- Priority Date
- 2024-06-04
- Filing Date
- 2025-04-18
- Publication Date
- 2025-12-11
AI Technical Summary
Existing organic electroluminescent devices suffer from problems such as high driving voltage, low luminous efficiency, and short lifespan, which limit their application areas.
An organic compound containing a phenanthrene-naphthofuran core structure is provided, which is linked to a triazine electron-deficient heteroaryl group at a specific position, and serves as an electron transport-type luminescent host material to improve carrier balance in the luminescent layer and enhance exciton generation and utilization efficiency.
It improves the luminous efficiency and lifetime of organic electroluminescent devices, enhances carrier mobility and carrier recombination region, and broadens the carrier generation region.
Smart Images

Figure CN2025089894_11122025_PF_FP_ABST
Abstract
Description
Organic compound, organic electroluminescent device, and electronic device
[0001] Cross-reference to related applications
[0002] This application claims priority to Chinese Patent Application No. CN202410718503.6, filed on June 4, 2024, the contents of which are incorporated herein in their entirety. TECHNICAL FIELD
[0003] The present application relates to the technical field of organic electroluminescent materials, in particular to an organic compound, an organic electroluminescent device and an electronic device thereof. BACKGROUND
[0004] In recent years, organic electroluminescent devices (OLEDs) have become a very popular emerging flat-panel display product at home and abroad, because OLED displays have the characteristics of self-emission, wide viewing angle, short response time, high efficiency, wide color gamut, etc.
[0005] An organic electroluminescent device (OLED) generally includes an anode, a cathode, and an organic layer formed between the two electrodes. The organic layer can include a hole injection layer, a hole transport layer, a hole auxiliary layer, an electron blocking layer, a light-emitting layer (containing a host and a dopant material), a hole blocking layer, an electron transport layer, an electron injection layer, etc. If a voltage is applied to the organic electroluminescent device, holes and electrons are injected into the light-emitting layer from the anode and the cathode, respectively. Then in the light-emitting layer, the injected holes and electrons recombine to form excitons. The excitons in the excited state release energy outward, and then the light-emitting layer emits light outward.
[0006] At present, there are still problems of poor performance in the use of organic electroluminescent devices, such as excessively high driving voltage, excessively low luminous efficiency, or short service life, etc. These all affect the use field of organic electroluminescent devices, therefore, it is still necessary to further study this field to improve the performance of organic electroluminescent devices. SUMMARY
[0007] In view of the above problems existing in the prior art, the purpose of the present application is to provide an organic compound, an organic electroluminescent device and an electronic device comprising the same, which is used in an organic electroluminescent device and can improve the performance of the device.
[0008] According to a first aspect of the present application, an organic compound is provided, having a structure as shown in formula II:
[0009] wherein D represents deuterium, and n represents 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, or 13;
[0010] L, L1and L2are identical or different, and each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms;
[0011] the substituents in L, L1and L2are identical or different, and each independently selected from deuterium, a cyano group, a halogen group, an alkyl group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, a deuterated alkyl group having 1 to 10 carbon atoms, a trialkylsilyl group having 3 to 12 carbon atoms, an aryl group having 6 to 20 carbon atoms, a deuterated aryl group having 6 to 20 carbon atoms, a heteroaryl group having 3 to 20 carbon atoms, or a cycloalkyl group having 5 to 10 carbon atoms;
[0012] Ar1and Ar2are identical or different, and each independently selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms;
[0013] the substituents in Ar1and Ar2are identical or different, and each independently selected from hydrogen, deuterium, a cyano group, a halogen group, an alkyl group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, a deuterated alkyl group having 1 to 10 carbon atoms, a trialkylsilyl group having 3 to 12 carbon atoms, an aryl group having 6 to 20 carbon atoms, a deuterated aryl group having 6 to 20 carbon atoms, a heteroaryl group having 3 to 20 carbon atoms, or a cycloalkyl group having 5 to 10 carbon atoms; optionally, any two adjacent substituents form a saturated or unsaturated 5- to 13-membered ring.
[0014] According to a second aspect of the present application, there is provided an organic electroluminescence device comprising an anode and a cathode disposed opposite to each other, and a functional layer disposed between the anode and the cathode; the functional layer comprising the organic compound described above.
[0015] In some embodiments, the organic electroluminescence device is selected from a red organic electroluminescence device.
[0016] According to a third aspect of the present application, there is provided an electronic device comprising the organic electroluminescence device of the second aspect.
[0017] The compound of the present application contains a phenanthronaphthofuran parent nucleus structure in the structure of the compound, and the parent nucleus is connected with an electron-deficient heteroaromatic group of triazine at a specific position, as an electron transport type light-emitting host material. On the one hand, the parent nucleus of phenanthronaphthofuran has a large conjugated area, which helps to enhance the intermolecular stacking of the target compound and improve the carrier of the compound; on the other hand, the oxygen atom in the furan ring has two pairs of lone pair electrons, which can also enhance the interaction between the molecules of the compound to a certain extent, further improving the carrier mobility of the compound. When the compound of the present application is used as an electron transport type material in a mixed host material, the carrier balance in the light-emitting layer can be improved, the carrier recombination area can be widened, the efficiency of exciton generation and utilization can be improved, and the luminous efficiency and service life of the device can be improved. BRIEF DESCRIPTION OF DRAWINGS
[0018] The accompanying drawings are included to provide a further understanding of the present application, and constitute a part of the specification, and are used together with the following detailed description to explain the present application, but do not constitute a limitation on the present application.
[0019] FIG. 1 is a schematic structural diagram of an organic electroluminescent device according to an embodiment of the present application.
[0020] FIG. 2 is a schematic structural diagram of an electronic device according to an embodiment of the present application.
[0021] Reference signs 100, anode 200, cathode 300, functional layer 310, hole injection layer 321, first hole transport layer 322, light-emitting adjustment layer 320, hole transport layer 330, organic light-emitting layer 340, electron transport layer 350, electron injection layer 400, electronic device DETAILED DESCRIPTION
[0022] Exemplary embodiments will now be described more fully with reference to the accompanying drawings. However, 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 the present application will be more thorough and complete, and will fully convey the concept of exemplary embodiments to those skilled in the art. The described features, structures, or characteristics can be combined in one or more embodiments in any suitable manner. In the following description, numerous specific details are provided to give a sufficient understanding of the embodiments of the present application.
[0023] According to a first aspect of the present application, an organic compound is provided, having a structure as shown in formula II:
[0024] wherein D represents deuterium, and n represents 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12 or 13.
[0025] L, L1and L2are the same or different, and each is independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms;
[0026] The substituents in L, L1and L2are the same or different, and each is independently selected from deuterium, a cyano group, a halogen group, an alkyl group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, a deuterated alkyl group having 1 to 10 carbon atoms, a trialkylsilyl group having 3 to 12 carbon atoms, an aryl group having 6 to 20 carbon atoms, a deuterated aryl group having 6 to 20 carbon atoms, a heteroaryl group having 3 to 20 carbon atoms, or a cycloalkyl group having 5 to 10 carbon atoms;
[0027] Ar1and Ar2are the same or different, and each is independently selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms;
[0028] The substituents in Ar1and Ar2are the same or different, and each is independently selected from hydrogen, deuterium, a cyano group, a halogen group, an alkyl group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, a deuterated alkyl group having 1 to 10 carbon atoms, a trialkylsilyl group having 3 to 12 carbon atoms, an aryl group having 6 to 20 carbon atoms, a deuterated aryl group having 6 to 20 carbon atoms, a heteroaryl group having 3 to 20 carbon atoms, or a cycloalkyl group having 5 to 10 carbon atoms; optionally, any two adjacent substituents form a saturated or unsaturated 5- to 13-membered ring.
[0029] In some embodiments, the organic compound of the present application has a structure as shown in Formula I:
[0030] wherein L, L1, L 2、 Ar1and Ar2have the same meaning in Formula II.
[0031] In the present application, the saturated or unsaturated 5- to 13-membered ring refers to a carbocyclic ring or a heterocyclic ring containing 5 to 13 ring atoms; for example, but not limited to, cyclopentane, cyclohexane, benzene ring, fluorene ring, pyran ring, tetrahydropyran ring, piperidine ring, tetrahydropiperidine ring, etc.
[0032] In the present application, the term "optionally" or "optionally" means that the event or environment described later can occur or can not occur. For example, "optionally, any two adjacent substituents form a saturated or unsaturated 3-15 membered ring" includes a case where any two adjacent substituents form a ring, and a case where any two adjacent substituents each independently exist without forming a ring. "Any two adjacent" can include a case where two substituents are on the same atom, and a case where one substituent is on each of two adjacent atoms. In the case where two substituents are on the same atom, the two substituents can form a saturated or unsaturated spiro ring with the atom to which they are commonly connected. In the case where one substituent is on each of two adjacent atoms, the two substituents can be fused into a ring.
[0033] In the present application, the description "each of... is independently" used interchangeably with "each of... is independently" and "each of... is independently" should be broadly interpreted. It can mean that the specific options expressed by the same symbols in different groups do not affect each other, or it can mean that the specific options expressed by the same symbols in the same group 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, chlorine, means that formula Q-1 represents a benzene ring having q substituents R", each of which can be the same or different, and the options for each R" do not affect each other; formula Q-2 represents a biphenyl in which each benzene ring has q substituents R", 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 for each R" do not affect each other.
[0034] In the present application, the term "substituted or unsubstituted" means that the functional group described after the term can or can not have a substituent (hereinafter, the substituent will be collectively referred to as Rc for convenience of description). For example, "substituted or unsubstituted aryl" means aryl having a substituent Rc or aryl without a substituent. The substituent Rc described above, for example, can be deuterium, a cyano group, a halogen group, an alkyl group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, a deuterated alkyl group having 1 to 10 carbon atoms, a trialkylsilyl group having 3 to 12 carbon atoms, an aryl group having 6 to 20 carbon atoms, a deuterated aryl group having 6 to 20 carbon atoms, a heteroaryl group having 3 to 20 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, or the like. The number of substitutions can be one or more.
[0035] In the present application, "a plurality of" means 2 or more, for example, 2, 3, 4, 5, 6, and the like.
[0036] In the present application, the number of carbon atoms of a substituted or unsubstituted functional group refers to the total number of carbon atoms.
[0037] The hydrogen atoms in the structure of the compounds of the present application include various isotopes of hydrogen element, such as hydrogen (H), deuterium (D) or tritium (T).
[0038] "D" in the structural formula of the compounds of the present application represents deuterium.
[0039] In the present application, aryl refers to an optional functional group or substituent derived from an aromatic carbocyclic ring. The aryl group can be a monocyclic aryl group (e.g., phenyl) or a polycyclic aryl group, in other words, the aryl group can be a monocyclic aryl group, a fused ring aryl group, two or more monocyclic aryl groups linked by carbon-carbon bonds, a monocyclic aryl group and a fused ring aryl group linked by carbon-carbon bonds, two or more fused ring aryl groups linked by carbon-carbon bonds. That is, unless otherwise specified, two or more aromatic groups linked by carbon-carbon bonds can also be regarded as aryl groups in the present application. Among them, the fused ring aryl group may, for example, include a bicyclic fused aryl group (e.g., naphthyl), a tricyclic fused aryl group (e.g., phenanthryl, fluorenyl, anthryl), etc. The aryl group does not contain heteroatoms such as B, N, O, S, P, Se and Si. Examples of aryl groups include, but are not limited to, phenyl, naphthyl, fluorenyl, spirobifluorenyl anthryl, phenanthryl, biphenyl, terphenyl, triphenylenyl pyrenyl, benzophenanthryl, chrysenyl, fluorenyl, spirobifluorenyl, etc.
[0040] In the present application, aryl refers to an optional functional group or substituent derived from an aromatic carbocyclic ring. The aryl group can be a monocyclic aryl group (e.g., phenyl) or a polycyclic aryl group, in other words, the aryl group can be a monocyclic aryl group, a fused ring aryl group, two or more monocyclic aryl groups linked by carbon-carbon bonds, a monocyclic aryl group and a fused ring aryl group linked by carbon-carbon bonds, two or more fused ring aryl groups linked by carbon-carbon bonds. That is, unless otherwise specified, two or more aromatic groups linked by carbon-carbon bonds can also be regarded as aryl groups in the present application. Among them, the fused ring aryl group may, for example, include a bicyclic fused aryl group (e.g., naphthyl), a tricyclic fused aryl group (e.g., phenanthryl, fluorenyl, anthryl), etc. The aryl group does not contain heteroatoms such as B, N, O, S, P, Se and Si. Examples of aryl groups include, but are not limited to, phenyl, naphthyl, fluorenyl, spirobifluorenyl
[0041] In the present application, terphenyl includes
[0042] In the present application, the number of carbon atoms in the substituted or unsubstituted aryl (arylene) group can be 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29 or 30. In some embodiments, the substituted or unsubstituted aryl group is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, in other embodiments, the substituted or unsubstituted aryl group is a substituted or unsubstituted aryl group having 6 to 25 carbon atoms, in other embodiments, the substituted or unsubstituted aryl group is a substituted or unsubstituted aryl group having 6 to 18 carbon atoms, in other embodiments, the substituted or unsubstituted aryl group is a substituted or unsubstituted aryl group having 6 to 15 carbon atoms.
[0043] In the present application, the fluorenyl group can be substituted by one or more substituents, and in the case where the above-mentioned fluorenyl group is substituted, the substituted fluorenyl group can be: etc., but is not limited thereto.
[0044] In the present application, as the substituent of aryl group, for example, but not limited to, phenyl, naphthyl, phenanthryl, biphenyl, fluorenyl, dimethylfluorenyl and the like.
[0045] In the present application, heteroaryl group refers to a monovalent aromatic ring or its derivative containing 1, 2, 3, 4, 5 or 6 heteroatoms in the ring, and the heteroatom can be one or more of B, O, N, P, Si, Se and S. The heteroaryl group can be a monocyclic heteroaryl group or a polycyclic heteroaryl group, in other words, the heteroaryl group can be a single aromatic ring system or a plurality of aromatic ring systems connected by carbon-carbon bonds, and any of the aromatic ring systems is an aromatic monocyclic ring or an aromatic fused ring. For example, the heteroaryl group can include thienyl, furanyl, pyrrolyl, imidazolyl, thiazolyl, oxazolyl, oxadiazolyl, triazolyl, pyridyl, bipyridyl, pyrimidyl, triazinyl, acridinyl, pyridazinyl, pyrazinyl, quinolyl, quinazolinyl, quinoxalinyl, phenoxazinyl, phthalazinyl, pyridopyrimidyl, pyridopyrazinyl, pyrazinopyrazinyl, isoquinolyl, indolyl, carbazolyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothiophenyl, dibenzothiophenyl, thienothiophenyl, benzofuranyl, phenanthrolinyl, isoxazolyl, thiadiazolyl, phenothiazinyl, silafluorenyl, dibenzofuranyl, and N-phenylcarbazolyl, N-pyridylcarbazolyl, N-methylcarbazolyl, and the like, but not limited thereto.
[0046] In the present application, the sub-heteroaryl group refers to a divalent or multivalent group formed by further losing one or more hydrogen atoms from the heteroaryl group.
[0047] In the present application, the number of carbon atoms of the substituted or unsubstituted heteroaryl (sub-heteroaryl) group 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. In some embodiments, the substituted or unsubstituted heteroaryl group is a substituted or unsubstituted heteroaryl group having a total of 3 to 30 carbon atoms, in other embodiments, the substituted or unsubstituted heteroaryl group is a substituted or unsubstituted heteroaryl group having a total of 12 to 18 carbon atoms, and in other embodiments, the substituted or unsubstituted heteroaryl group is a substituted or unsubstituted heteroaryl group having a total of 5 to 12 carbon atoms.
[0048] In the present application, as the substituent of heteroaryl group, for example, but not limited to, pyridyl, carbazolyl, dibenzothiophenyl, dibenzofuranyl, benzoxazolyl, benzothiazolyl, benzimidazolyl.
[0049] In the present application, the substituted heteroaryl group can be a heteroaryl group in which one or more hydrogen atoms is replaced with a group such as a deuterium atom, a halogen group, a cyano group, an aryl group, a heteroaryl group, a trialkylsilyl group, an alkyl group, a cycloalkyl group, a halogenated alkyl group, and the like.
[0050] In the present application, the alkyl group having 1 to 10 carbon atoms can include a linear alkyl group having 1 to 10 carbon atoms and a branched 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, or 10. Specific examples of the alkyl group include, but are not limited to, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, t-butyl, n-pentyl, isopentyl, neopentyl, n-hexyl, and the like.
[0051] In the present application, the deuterated aryl group having 6 to 20 carbon atoms has, for example, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, or 20 carbon atoms. Specific examples of the deuterated aryl group include, but are not limited to, penta-deuteriophenyl, tri-deuteriophenyl.
[0052] In the present application, the halogen group can be, for example, fluorine, chlorine, bromine, or iodine.
[0053] In the present application, specific examples of the trialkylsilyl group include, but are not limited to, trimethylsilyl, triethylsilyl, and the like.
[0054] In the present application, specific examples of the haloalkyl group include, but are not limited to, trifluoromethyl.
[0055] In the present application, the cycloalkyl group having 3 to 10 carbon atoms has, for example, 3, 4, 5, 6, 7, 8, or 10 carbon atoms. Specific examples of the cycloalkyl group include, but are not limited to, cyclopentyl, cyclohexyl, adamantyl.
[0056] In the present application, the deuterated alkyl group having 1 to 10 carbon atoms has, for example, 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10 carbon atoms. Specific examples of the deuterated alkyl group include, but are not limited to, tri-deuteromethyl.
[0057] In the present application, the haloalkyl group having 1 to 10 carbon atoms has, for example, 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10 carbon atoms. Specific examples of the haloalkyl group include, but are not limited to, trifluoromethyl.
[0058] In the present application, a ring system formed by n atoms is an n-membered ring. For example, a phenyl group is a 6-membered ring. A 5- to 13-membered ring refers to a cyclic group having 5 to 13 ring atoms. Examples of the 5- to 13-membered ring include a cyclopentane ring (5-membered ring), a cyclohexane ring (6-membered ring), a benzene ring (6-membered ring), a fluorene ring (13-membered ring), and the like.
[0059] In the present application, refers to a chemical bond to which other groups are connected.
[0060] In the present application, the indefinite position connection bond refers to a single bond extending from a ring system which indicates that one end of the bond can be attached to any position in the ring system through which the bond runs, and the other end is attached to the remainder of the compound molecule. For example, as shown in the following formula (f), the naphthyl group represented by formula (f) is attached to the remainder of the molecule through two indefinite bonds that run through the bicyclic ring system, and the meaning represented thereby includes any of the possible attachment modes shown in formulae (f-1) to (f-10):
[0061] For another example, as shown in the following formula (X'), the dibenzofuranyl group represented by formula (X') is attached to the remainder of the molecule through one indefinite bond that runs from the middle of one of the phenyl rings, and the meaning represented thereby includes any of the possible attachment modes shown in formulae (X'-1) to (X'-4):
[0062] An indefinite substituent in the present application refers to a substituent that is attached through a single bond that runs from the center of a ring system, and indicates that the substituent can be attached 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 attached to the quinoline ring through one indefinite bond, and the meaning represented thereby includes any of the possible attachment modes shown in formulae (Y-1) to (Y-7):
[0063] In some embodiments, the organic compound of the present application is selected from the group consisting of the following formula (I-1), formula (I-2), or formula (I-3):
[0064] In some embodiments, L, L1, and L2 are the same or different, and each is independently selected from the group consisting of a single bond, a substituted or unsubstituted arylene group having 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 carbon atoms, and a substituted or unsubstituted heteroarylene group having 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 carbon atoms.
[0065] In some embodiments, L, L1, and L2 are the same or different, and each is independently selected from the group consisting of a single bond, a substituted or unsubstituted arylene group having 6 to 18 carbon atoms, and a substituted or unsubstituted heteroarylene group having 5 to 18 carbon atoms.
[0066] In some embodiments, the substituents in L, L1and L2are the same or different, and each is independently selected from deuterium, fluorine, cyano, alkyl of 1 to 4 carbon atoms, haloalkyl of 1 to 4 carbon atoms, deuterated alkyl of 1 to 4 carbon atoms, trialkylsilyl of 3 to 7 carbon atoms, aryl of 6 to 12 carbon atoms, or deuterated aryl of 6 to 12 carbon atoms.
[0067] In some embodiments, L, L1and L2are the same or different, and each is independently a single bond, substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted biphenylene, substituted or unsubstituted phenanthrylene, substituted or unsubstituted fluorenylene, substituted or unsubstituted pyridylene, substituted or unsubstituted dibenzofuranylene, substituted or unsubstituted dibenzothiophenylene, substituted or unsubstituted carbazolylene.
[0068] In some embodiments, the substituents in L, L1and L2are the same or different, and each is independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trimethylsilyl, trideuteromethyl, pentadeuterophenyl, phenyl, or naphthyl.
[0069] In some embodiments, L1and L2are the same or different, and each is independently selected from a group consisting of a single bond or:
[0070] In some embodiments, L is selected from a group consisting of a single bond or:
[0071] In some embodiments, L1and L2are the same or different, and each is independently selected from a group consisting of a single bond or:
[0072] In some embodiments, L is selected from a group consisting of a single bond or:
[0073] In some embodiments, Ar1and Ar2are the same or different, and each is independently selected from substituted or unsubstituted aryl of 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 carbon atoms, or substituted or unsubstituted heteroaryl of 3, 4, 5, 6, 7, 8, 9, 10, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, or 30 carbon atoms.
[0074] In some embodiments, Ar1and Ar2are the same or different, and each is independently selected from a substituted or unsubstituted aryl group having a carbon number of 6 to 25 or a substituted or unsubstituted heteroaryl group having a carbon number of 12 to 18.
[0075] In some embodiments, the substituents in Ar1and Ar2are the same or different, and each is independently selected from deuterium, a halogen group, a cyano group, a haloalkyl group having a carbon number of 1 to 4, a deuterated alkyl group having a carbon number of 1 to 4, an alkyl group having a carbon number of 1 to 4, a cycloalkyl group having a carbon number of 5 to 10, an aryl group having a carbon number of 6 to 15, a heteroaryl group having a carbon number of 5 to 12, a trialkylsilyl group having a carbon number of 3 to 7, or a deuterated aryl group having a carbon number of 6 to 15, and optionally, any two adjacent substituents form a benzene ring or a fluorene ring.
[0076] In some embodiments, Ar1and Ar2are the same or different, and each is independently selected from a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted anthryl group, a substituted or unsubstituted pyrenyl group, a substituted or unsubstituted triphenylenyl group, a substituted or unsubstituted spirobifluorenyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted carbazolyl group.
[0077] In some embodiments, the substituents in Ar1and Ar2are the same or different, and each is independently selected from deuterium, fluorine, a cyano group, a methyl group, an ethyl group, an isopropyl group, a tert-butyl group, a trifluoromethyl group, a trideuteromethyl group, a trimethylsilyl group, a pentadeuteriophenyl group, a phenyl group, or a naphthyl group.
[0078] In some embodiments, Ar1and Ar2are the same or different, and each is independently selected from the following groups:
[0079] In some embodiments, Ar1and Ar2are the same or different, and each is independently selected from the following groups:
[0080] In some embodiments, are the same or different, and each is independently selected from the following groups:
[0081] In some more specific embodiments, are selected from the following groups:
[0082] are selected from the following groups:
[0083] In some embodiments, is selected from the group consisting of:
[0084] In some embodiments, the organic compound of the present application is selected from the group consisting of:
[0085] In a second aspect, the present application provides an organic electroluminescent device, comprising an anode, a cathode, and a functional layer disposed between the anode and the cathode; wherein the functional layer comprises the organic compound according to the first aspect of the present application.
[0086] The organic compound provided by the present application can be used to form at least one organic film layer in the functional layer to improve the luminous efficiency and lifetime of the organic electroluminescent device.
[0087] Optionally, the functional layer comprises an organic light-emitting layer, and the organic light-emitting layer comprises the organic compound. The organic light-emitting layer can be composed of the organic compound provided by the present application, or can be composed of the organic compound provided by the present application and other materials.
[0088] According to a specific embodiment, the organic electroluminescent device is shown in FIG. 1. The organic electroluminescent device can comprise, in sequence, an anode 100, a hole injection layer 310, a first hole transport layer 321, a light-emitting adjustment layer (also referred to as a hole auxiliary layer or a second hole transport layer) 322, an organic light-emitting layer 330, an electron transport layer 340, an electron injection layer 350, and a cathode 200.
[0089] In the present application, the anode 100 comprises an anode material, which is preferably a material with a large work function that facilitates hole injection into the functional layer. Specific examples of the anode material include: metals such as nickel, platinum, vanadium, chromium, copper, zinc and gold or alloys thereof; 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-(ethylene-1,2-dioxy)thiophene] (PEDT), polypyrrole and polyaniline, but are not limited thereto. A transparent electrode comprising indium tin oxide (ITO) is preferably used as the anode.
[0090] In the present application, the first hole transport layer or the light-emitting adjustment layer can each comprise one or more hole transport materials, which can be selected from carbazole polymers, carbazole-linked triarylamine compounds or other types of compounds, and can be selected from the following compounds or any combination thereof:
[0091] In one embodiment, the first hole transport layer 321 is composed of HT-1.
[0092] In one embodiment, the light-emitting adjustment layer 322 is composed of HT-2.
[0093] Optionally, a hole injection layer 310 is further provided between the anode 100 and the first hole transport layer 321 to enhance the ability of injecting holes into the first hole transport layer 321. The hole injection layer 310 can be selected from benzidine derivatives, starburst arylamine compounds, phthalocyanine derivatives or other materials, which are not particularly limited in the present application. The material of the hole injection layer 310 can be selected from the following compounds or any combination thereof, for example:
[0094] In one embodiment of the present application, the hole injection layer 310 is composed of PD and HT-1.
[0095] Optionally, the organic light-emitting layer 330 can comprise the host material and the guest material. Optionally, the organic light-emitting layer 330 is composed of the host material and the guest material, and the holes injected into the organic light-emitting layer 330 and the electrons injected into the organic light-emitting layer 330 can recombine in the organic light-emitting layer 330 to form excitons, which transfer energy to the host material, the host material transfers energy to the guest material, and the guest material can emit light.
[0096] The host material of the organic light-emitting layer 330 can include a metal chelate compound, a bisstyryl derivative, an aromatic amine derivative, a dibenzofuran derivative, or other types of materials. Optionally, the host material includes the organic compound of the present application.
[0097] The guest material of the organic light-emitting layer 330 can be a compound having condensed aryl rings or derivatives thereof, a compound having heteroaryl rings or derivatives thereof, an aromatic amine derivative, or other materials, which are not particularly limited in the present application. The guest material is also referred to as a dopant or a dopant material. It can be classified into a fluorescent dopant and a phosphorescent dopant according to the type of light emission. For example, specific examples of the phosphorescent dopant include, but are not limited to,
[0098] In one embodiment of the present application, the organic electroluminescent device is a red organic electroluminescent device. In a more specific embodiment, the host material of the organic light-emitting layer 330 consists of the organic compound. The guest material can be, for example, RD.
[0099] In another embodiment, the host material of the organic light-emitting layer 330 includes the organic compound of the present application and RH-P The guest material can be, for example, RD.
[0100] In one embodiment of the present application, the organic electroluminescent device is a green organic electroluminescent device. In a more specific embodiment, the host material of the organic light-emitting layer 330 includes the organic compound of the present application. The guest material can be, for example, fac-Ir(ppy)3.
[0101] The electron transport layer 340 can be a single layer structure or a multi-layer structure, and can include one or more electron transport materials selected from, but not limited to, BmPyPhB, LiQ, a benzimidazole derivative, an oxadiazole derivative, a quinoxaline derivative, a triazine derivative, and other electron transport materials, which are not particularly limited in the present application. The material of the electron transport layer 340 includes LiQ and other electron transport materials, which can be selected from, but are not limited to, the following compounds:
[0102] In one embodiment of the present application, the electron transport layer 340 consists of ET-1 and LiQ.
[0103] In the present application, the cathode 200 includes a cathode material, which is a material having a small work function that facilitates electron injection into the functional layer. Specific examples of the cathode material include, but are not limited to, a metal such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or an alloy thereof; or a multi-layered material such as LiF / Al, Liq / Al, LiO2 / Al, LiF / Ca, LiF / Al, and BaF2 / Ca. Alternatively, a metal electrode including magnesium and silver is included as the cathode.
[0104] Alternatively, 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 can include an inorganic material such as an alkali metal sulfide, an alkali metal halide, or the like, or can include a complex of an alkali metal and an organic material. In one embodiment of the present application, the electron injection layer 350 includes ytterbium (Yb).
[0105] The present application not only provides the organic electroluminescent device including the compound represented by Formula 1 for the organic light-emitting layer. The present application also provides an electronic device including the organic electroluminescent device of the present application.
[0106] According to one embodiment, as shown in FIG. 2, an electronic device provided is electronic device 400. 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, can include but are not limited to computer screens, mobile phone screens, televisions, electronic paper, emergency lighting, optical modules, etc.
[0107] The synthesis method of the organic compound of the present application will be specifically described below in connection with the synthesis examples, but the present disclosure is not limited in any way by this.
[0108] Synthesis Examples
[0109] Those skilled in the art will recognize that the chemical reactions described in the present application can be used to practice the application in a variety of synthetic routes and that the application is not limited to the reaction conditions presented in the synthetic schemes. It will be further understood by those skilled in the art that the synthesis of the compounds of the present application can be accomplished by the use of other known reagents and techniques in place of those described in the present application, or by making routine modifications to the reaction conditions described in the present application. The compounds of the present application for which no synthetic methods are described in the present application are commercially available starting materials.
[0110] Synthesis of Sub-a1:
[0111] Into a 500 mL three-necked flask, Sub-a1 (18.93 g, 55 mmol), RM-2 (10.97 g, 50 mmol), tetrakis(triphenylphosphine)palladium (0.58 g, 0.5 mmol), tetrabutylammonium bromide (TBAB, 1.61 g, 5 mmol), anhydrous sodium carbonate (10.60 g, 100 mmol), toluene (180 mL), anhydrous ethanol (45 mL) and deionized water (45 mL) were added successively under nitrogen atmosphere. The stirring and heating were started and the reaction was allowed to warm to reflux for 8 h. After the system was cooled to room temperature, the reaction mixture was extracted with dichloromethane (100 mL x 3 times). The combined organic phase was dried over anhydrous magnesium sulfate, filtered and the solvent was removed by distillation under reduced pressure to give the crude product. The crude product was purified by silica gel column chromatography using dichloromethane / n-heptane as the mobile phase to give Sub-b1 (11.42 g, 64% yield) as a white solid.
[0112] Synthesis of Sub-b1:
[0113] Into a 500 mL three-necked flask, Sub-a1 (18.93 g, 55 mmol), RM-2 (10.97 g, 50 mmol), tetrakis(triphenylphosphine)palladium (0.58 g, 0.5 mmol), tetrabutylammonium bromide (TBAB, 1.61 g, 5 mmol), anhydrous sodium carbonate (10.60 g, 100 mmol), toluene (180 mL), anhydrous ethanol (45 mL) and deionized water (45 mL) were added successively under nitrogen atmosphere. The stirring and heating were started and the reaction was allowed to warm to reflux for 8 h. After the system was cooled to room temperature, the reaction mixture was extracted with dichloromethane (100 mL x 3 times). The combined organic phase was dried over anhydrous magnesium sulfate, filtered and the solvent was removed by distillation under reduced pressure to give the crude product. The crude product was purified by silica gel column chromatography using dichloromethane / n-heptane as the mobile phase to give Sub-b1 (11.42 g, 64% yield) as a white solid.
[0114] Referring to the synthesis of Sub-b1, Sub-b2 to Sub-b3 were synthesized by using the reactants A and B shown in Table 1 to replace Sub-a1 and RM-2, respectively.
[0115] Table 1: Synthesis of Sub-b2 to Sub-b3
[0116] Synthesis of Sub-c1:
[0117] Into a 1000 mL three-necked flask, (methoxymethyl)triphenylphosphonium chloride (51.25 g, 149.5 mmol), potassium tert-butoxide (18.10 g, 161 mmol) and anhydrous tetrahydrofuran (230 mL) were added under nitrogen atmosphere, the system was cooled to -15 °C and kept for 30 min; then Sub-a1 (46.38 g, 130 mmol) was weighed and dissolved in anhydrous tetrahydrofuran (230 mL), the solution was slowly added to the reaction system by constant pressure dropping funnel, the temperature was kept at -15 °C during the dropping process, and after the dropping was completed, the reaction was continued to be stirred at -15 °C for 1 h. Then the reaction system was naturally warmed to room temperature, extracted with dichloromethane (200 mL x 3 times), the organic phases were combined and dried with anhydrous magnesium sulfate, filtered and the solvent was removed by reduced pressure distillation to obtain a crude product. The crude product was purified by silica gel column chromatography using n-heptane / dichloromethane as the mobile phase to obtain a gray-white solid Sub-c1 (39.52 g, yield 79%).
[0118] Referring to Sub-c1, Sub-c2 to Sub-c3 were synthesized by using the reactants C shown in Table 2 to replace Sub-b1.
[0119] Table 2: Synthesis of Sub-c2 to Sub-c3
[0120] Synthesis of Sub-d1:
[0121] Into a 1000 mL three-necked flask, Sub-c1 (45.80 g, 119 mmol), Eaton’s reagent (4.5 mL) and chlorobenzene (500 mL) were sequentially added under nitrogen atmosphere, the system was warmed to reflux and the reaction was continued to be stirred for 4 h. After the reaction system was cooled to room temperature, the reaction solution was poured into 1000 mL deionized water, neutralized with saturated sodium hydroxide solution, then extracted with dichloromethane (250 mL x 3 times), the organic phases were combined and dried with anhydrous magnesium sulfate, filtered and the solvent was removed 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 a white solid Sub-d1 (26.87 g, yield 64%).
[0122] Referring to the synthesis of Sub-d1, Sub-d2 to Sub-d3 were synthesized by using the reactants D shown in Table 3 to replace Sub-c1.
[0123] Table 3: Synthesis of Sub-d2 to Sub-d3
[0124] Synthesis of Sub-e1:
[0125] Into a 500 mL three-necked flask, Sub-dl (17.64 g, 50 mmol), bis(pinacolato)diboron (14.0 g, 55 mmol), potassium acetate (10.8 g, 110 mmol), and 1,4-dioxane (180 mL) were sequentially added under nitrogen atmosphere. The stirring and heating were started, and the system was warmed to 40 °C. Then tris(dibenzylideneacetone)dipalladium (Pd2(dba)3, 0.46 g, 0.50 mmol) and 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl (XPhos, 0.48 g, 1.0 mmol) were rapidly added. The system was warmed to reflux, and the reaction was stirred overnight. After the system was cooled to room temperature, 200 mL of water was added, and the mixture was stirred thoroughly for 30 min. The mixture was filtered under reduced pressure. The filter cake was washed with deionized water until neutral, and then washed with 100 mL of anhydrous ethanol. Sub-e1 (16.66 g, 75% yield) was obtained as a white solid. The crude product was slurried with n-heptane once and then dissolved in 200 mL of toluene. The catalyst was removed by passing the solution through a silica gel column. Sub-e1 was obtained as a white solid after concentration.
[0126] Referring to the synthesis of Sub-e1, Sub-e2 to Sub-e3 were synthesized using the reactants E shown in Table 4 instead of Sub-dl.
[0127] Table 4: Synthesis of Sub-e2 to Sub-e3
[0128] Synthesis of Sub-f1:
[0129] Into a 500 mL three-necked flask, RM-3 (13.89 g, 50 mmol), 4-chlorobenzeneboronic acid (8.60 g, 55 mmol), tetrakis(triphenylphosphine)palladium (0.58 g, 0.5 mmol), anhydrous sodium carbonate (10.60 g, 100 mmol), toluene (180 mL), anhydrous ethanol (45 mL), and deionized water (45 mL) were sequentially added under nitrogen atmosphere. The stirring and heating were started, and the system was warmed to reflux for 8 h. After the system was cooled to room temperature, the mixture was extracted with dichloromethane (100 mL x 3 times). The organic phases were combined and dried with anhydrous magnesium sulfate. The mixture was filtered, and the solvent was removed by distillation under reduced pressure. The crude product was purified by silica gel column chromatography using dichloromethane / n-heptane as the mobile phase. Sub-f1 (14.50 g, 82% yield) was obtained as a white solid.
[0130] Referring to the synthesis of Sub-f1, Sub-f2 to Sub-f10 were synthesized using the reactants F shown in Table 5 instead of RM-3, and the reactant G instead of 4-chlorobenzeneboronic acid.
[0131] Table 5: Synthesis of Sub-f2 to Sub-f10
[0132] Synthesis of compound 3
[0133] Into a 250 mL three-necked flask, Sub-e1 (11.66 g, 26.25 mmol), RM-4 (7.94 g, 25 mmol), palladium acetate (42 mg, 0.25 mmol), 2-dicyclohexylphosphino-2',4',6' triisopropyl biphenyl (XPhos, 0.24 g, 0.5 mmol), anhydrous potassium carbonate (6.9 g, 50 mmol), tetrabutylammonium bromide (0.8 g, 2.5 mmol), toluene (100 mL), tetrahydrofuran (25 mL) and deionized water (25 mL) were added successively under nitrogen atmosphere. Stirring and heating were started and the temperature was raised to reflux for 16 h. After the system was cooled to room temperature, dichloromethane (100 mL x 3 times) was used to extract the product. The organic phase was combined and dried over anhydrous magnesium sulfate. After filtration, the solvent was removed by distillation under reduced pressure to obtain the crude product. Silica gel column chromatography was performed on the crude product using dichloromethane / n-heptane as the mobile phase to obtain compound 3 (10.80 g, yield 72%, m / z = 600.20 [M+H] + ).
[0134] Referring to the synthesis of compound 3, the reactants H shown in Table 6 were used to replace Sub-e1, and the reactants J were used to replace RM-4, to synthesize the compounds of the application in Table 6.
[0135] Table 6: Synthesis of compounds of the application
[0136] NMR data of some compounds:
[0137] NMR data of compound 9: 1 H-NMR (400 MHz, CD2Cl2) δ ppm: 9.51 (s, 1H), 8.82 (d, 2H), 8.69-8.58 (m, 2H), 8.35 (d, 1H), 8.26 (d, 1H), 8.21-8.09 (m, 4H), 8.01 (d, 1H), 7.90 (d, 1H), 7.86 (d, 1H), 7.76-7.47 (m, 10H), 7.41 (t, 1H).
[0138] Organic electroluminescent device preparation and evaluation:
[0139] Example 1: Fabrication of a red organic electroluminescent device
[0140] First, anodizing pretreatment is performed through the following process: [The process is repeated in the original text, so the translation is incomplete.] On the ITO / Ag / ITO substrate, surface treatment is performed using ultraviolet ozone and O2:N2 plasma to increase the work function of the anode. Organic solvents are used to clean the surface of the ITO substrate to remove impurities and oil stains.
[0141] PD:HT-1 was co-deposited on the experimental substrate (anode) at a deposition rate ratio of 2%:98%, forming a layer with a thickness of [missing information]. A hole injection layer (HIL) is formed, and then HT-1 is vacuum-deposited on the hole injection layer to form a thickness of [missing information]. The first hole transport layer.
[0142] Compound HT-2 was vacuum-deposited onto the first hole transport layer to form a thickness of [missing information]. The light-emitting adjustment layer.
[0143] Next, compound 3:RH-P:RD was co-deposited on the light-emitting adjustment layer in a ratio of 49%:49%:2% to form a layer with a thickness of [missing information]. The red light emitting layer (EML).
[0144] On the light-emitting layer, compound ET-1 and LiQ are co-deposited at a 1:1 evaporation rate ratio to form... A thick electron transport layer (ETL) is formed by depositing Yb onto the electron transport layer to create a layer with a thickness of [thickness value missing]. An electron-injected layer (EIL) is formed, and then magnesium (Mg) and silver (Ag) are co-deposited onto the electron-injected layer at a 1:9 evaporation rate, forming a layer with a thickness of [missing information]. The cathode.
[0145] Furthermore, the vacuum evaporation thickness on the aforementioned cathode is [missing information]. The CP forms a capping layer, thereby completing the fabrication of the red organic electroluminescent device.
[0146] Examples 2-70
[0147] Except that, when fabricating the light-emitting layer, compound X in Table 7 is used instead of compound 3 in Example 1, the organic electroluminescent device is prepared using the same method as in Example 1.
[0148] Comparative Examples 1-4
[0149] An organic electroluminescent device was produced in the same manner as in Example 1, except that Compound A, Compound B, Compound C and Compound D in Table 7 below were used instead of Compound 3 in Example 1 when producing the light-emitting layer.
[0150] In the production of each of the examples and comparative examples, the compounds used had the following structures:
[0151] The red organic electroluminescent devices produced in Examples 1 to 70 and Comparative Examples 1 to 4 were tested for performance, specifically for IVL performance under the condition of 10 mA / cm 2 95 Device lifetime was tested under the condition of 20 mA / cm 2 The test results are shown in Table 7.
[0152] Table 7
[0153] As can be seen from Table 7 above, when the compounds of the present application are used as host materials for red organic electroluminescent devices, the luminous efficiency (Cd / A) of the device examples 1 to 70 is at least 12.9% higher, and the T 95 lifetime is at least 18.7% higher, compared to Comparative Examples 1 to 4.
[0154] The preferred embodiments of the present application have been described in detail above with reference to the accompanying drawings, but the present application is not limited to the specific details of the above-described embodiments, and various simple modifications can be made to the technical solutions of the present application within the technical concept of the present application, and these simple modifications all belong to the protection scope of the present application.
Claims
1. An organic compound having the structure of Formula II: ###00001### Formula II wherein D represents deuterium, n represents 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, or 13; L, L1, and L2 are the same or different, and each is independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms; the substituents in L, L1, and L2 are the same or different, and each is independently selected from deuterium, a cyano group, a halogen group, an alkyl group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, a deuterated alkyl group having 1 to 10 carbon atoms, a trialkylsilyl group having 3 to 12 carbon atoms, an aryl group having 6 to 20 carbon atoms, a deuterated aryl group having 6 to 20 carbon atoms, a heteroaryl group having 3 to 20 carbon atoms, or a cycloalkyl group having 5 to 10 carbon atoms; Ar1and Ar2are the same or different, and each is independently selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms; the substituents in Ar1and Ar2are the same or different, and each is independently selected from hydrogen, deuterium, a cyano group, a halogen group, an alkyl group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, a deuterated alkyl group having 1 to 10 carbon atoms, a trialkylsilyl group having 3 to 12 carbon atoms, an aryl group having 6 to 20 carbon atoms, a deuterated aryl group having 6 to 20 carbon atoms, a heteroaryl group having 3 to 20 carbon atoms, or a cycloalkyl group having 5 to 10 carbon atoms; optionally, any two adjacent substituents form a saturated or unsaturated 5- to 13-membered ring.
2. The organic compound of claim 1, having the structure of Formula I: ###0001### wherein L, L1, and L2 are the same or different, and each is independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms; the substituents in L, L1, and L2 are the same or different, and each is independently selected from deuterium, a cyano group, a halogen group, an alkyl group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, a deuterated alkyl group having 1 to 10 carbon atoms, a trialkylsilyl group having 3 to 12 carbon atoms, an aryl group having 6 to 20 carbon atoms, a deuterated aryl group having 6 to 20 carbon atoms, a heteroaryl group having 3 to 20 carbon atoms, or a cycloalkyl group having 5 to 10 carbon atoms; Ar1and Ar2are the same or different, and each is independently selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms; the substituents in Ar1and Ar2are the same or different, and each is independently selected from hydrogen, deuterium, a cyano group, a halogen group, an alkyl group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, a deuterated alkyl group having 1 to 10 carbon atoms, a trialkylsilyl group having 3 to 12 carbon atoms, an aryl group having 6 to 20 carbon atoms, a deuterated aryl group having 6 to 20 carbon atoms, a heteroaryl group having 3 to 20 carbon atoms, or a cycloalkyl group having 5 to 10 carbon atoms; optionally, any two adjacent substituents form a saturated or unsaturated 5- to 13-membered ring.
3. The organic compound according to claim 1 or 2, wherein L, L1and L2are the same or different, and each independently a single bond, substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted biphenylene, substituted or unsubstituted phenanthrylene, substituted or unsubstituted fluorenylene, substituted or unsubstituted pyridylene, substituted or unsubstituted dibenzofuranylene, substituted or unsubstituted dibenzothiophenylene, substituted or unsubstituted carbazolylene; Optionally, the substituents in L, L1and L2are each independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trimethylsilyl, trideuteromethyl, pentadeuterophenyl, phenyl or naphthyl.
4. The organic compound according to any one of claims 1 to 3, wherein, L1and L2are the same or different and each independently selected from the group consisting of a single bond or: Optionally, L is selected from the group consisting of a single bond or the following groups:
5. The organic compound according to any one of claims 1 to 4, wherein, Ar1and Ar2are the same or different, and each independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted anthryl, substituted or unsubstituted pyrenyl, substituted or unsubstituted triphenylylene, substituted or unsubstituted spirobifluorenyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted carbazolyl; Optionally, the substituents in Ar1and Ar2are the same or different, and each independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, trideuteromethyl, trimethylsilyl, pentadeuterophenyl, phenyl or naphthyl.
6. The organic compound according to any one of claims 1 to 5, wherein Ar1and Ar2are the same or different and each independently selected from the following groups:
7. The organic compound according to any one of claims 1 to 6, wherein the same or different, and each independently selected from the group consisting of:
8. The organic compound according to any one of claims 1 to 7, wherein selected from the group consisting of:
9. The organic electroluminescent device according to any one of claims 1 to 8, wherein selected from the group consisting of: selected from the group consisting of:
10. An organic electroluminescent device according to any one of claims 1 to 9, wherein The organic compound is selected from the group consisting of:
11. An organic electroluminescent device comprising an anode and a cathode disposed opposite each other, and a functional layer disposed between the anode and the cathode; characterized in that, The functional layer comprises the organic compound according to any one of claims 1 to 10; Optionally, the functional layer comprises an organic light-emitting layer, and the organic light-emitting layer comprises the organic compound.
12. An electronic device, characterized by The organic electroluminescent device according to claim 11. The organic electroluminescent device according to claim 11.
Citation Information
Patent Citations
Condensed-cyclic compound, method for preparing the condensed-cyclic compound and organic light-emitting device including the condensed-cyclic compound
CN103058987A
Organic electroluminescence material and device
CN111454235A
Novel compound and organic light emitting device including same
CN115210228A
Phenanthrene derivative, organic electron transport material and organic electroluminescent device
CN115232075A
Compound for organic optoelectronic device, composition for organic optoelectronic device, organic optoelectronic device, and display device
CN115872980A