Organic compounds, organic electroluminescent devices, and electronic devices

Abstract

This application relates to the field of organic electroluminescent materials technology, providing a compound and an organic electroluminescent device and electronic apparatus containing the same. The compound structure of this application contains a phenanthrene-naphthofuran core structure, with the core linked to a substituted triazine group at a specific position, serving as an electron transport host material. Using this compound as the host material for the luminescent layer can improve carrier balance in the luminescent layer, broaden the carrier recombination region, improve exciton generation and utilization efficiency, and enhance the device's luminous efficiency and lifetime.

Description

Technical Field

[0001] This application relates to the field of organic electroluminescent materials technology, and more particularly to an organic compound and its organic electroluminescent device and electronic device. Background Technology

[0002] In recent years, organic light-emitting devices (OLEDs) have become a very popular emerging flat panel display product both domestically and internationally. This is because OLED displays have characteristics such as self-illumination, wide viewing angle, short response time, high efficiency, and wide color gamut.

[0003] Organic light-emitting diodes (OLEDs) typically include an anode, a cathode, and an organic layer formed between these two electrodes. This organic layer may include a hole injection layer, a hole transport layer, a hole auxiliary layer, an electron blocking layer, a light-emitting layer (containing host and dopant materials), a hole blocking layer, an electron transport layer, and an electron injection layer. When a voltage is applied to the OLED, holes and electrons are injected into the light-emitting layer from the anode and cathode, respectively. Then, in the light-emitting layer, the injected holes and electrons recombine to form excitons. These excitons, in an excited state, release energy, causing the light-emitting layer to emit light.

[0004] Currently, organic electroluminescent devices still suffer from poor performance issues during use, such as excessively high driving voltage, low luminous efficiency, or short lifespan. These problems limit their application areas, so further research is necessary to improve their performance. Summary of the Invention

[0005] In view of the above-mentioned problems existing in the prior art, the purpose of this application is to provide an organic compound and an organic electroluminescent device and electronic device containing the same, wherein the organic compound used in the organic electroluminescent device can improve the performance of the device.

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

[0007]

[0008] Among them, L, L1 and L2 may be the same or different, and each is independently selected from single bonds, substituted or unsubstituted aryl groups with 6 to 30 carbon atoms, and substituted or unsubstituted heteroaryl groups with 3 to 30 carbon atoms.

[0009] The substituents in L, L1, and L2 may be the same or different, and each is independently selected from deuterium, cyano, halogen group, alkyl with 1 to 10 carbon atoms, haloalkyl with 1 to 10 carbon atoms, deuterated alkyl with 1 to 10 carbon atoms, trialkylsilyl with 3 to 12 carbon atoms, aryl with 6 to 20 carbon atoms, deuterated aryl with 6 to 20 carbon atoms, heteroaryl with 3 to 20 carbon atoms, or cycloalkyl with 5 to 10 carbon atoms;

[0010] Ar1 and Ar2 may be the same or different, and each is independently selected from substituted or unsubstituted aryl groups with 6 to 30 carbon atoms, or substituted or unsubstituted heteroaryl groups with 3 to 30 carbon atoms.

[0011] The substituents in Ar1 and Ar2 may be the same or different, and each is independently selected from hydrogen, deuterium, cyano, halogen group, alkyl with 1 to 10 carbon atoms, haloalkyl with 1 to 10 carbon atoms, deuteralkyl with 1 to 10 carbon atoms, trialkylsilyl with 3 to 12 carbon atoms, aryl with 6 to 20 carbon atoms, deuterylaryl with 6 to 20 carbon atoms, heteroaryl with 3 to 20 carbon atoms, or cycloalkyl with 5 to 10 carbon atoms; optionally, any two adjacent substituents form a saturated or unsaturated 5 to 13-membered ring.

[0012] According to a second aspect of this application, an organic electroluminescent device is provided, 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 aforementioned organic compound.

[0013] According to a third aspect of this application, an electronic device is provided, including the organic electroluminescent device described in the second aspect.

[0014] The compound structure of this application contains a phenanthrene-naphthofuran core structure, which is linked to an electron-deficient heteroaryl group of triazine at a specific position, serving as an electron transport-type luminescent host material. On the one hand, the phenanthrene-naphthofuran core has a large conjugated area, which helps to enhance the intermolecular packing of the target compound and increase the charge carriers of the compound; on the other hand, the oxygen atom in the furan ring has two lone pairs of electrons, which can also enhance the interaction between compound molecules to a certain extent, further improving the charge carrier mobility of the compound. When the compound of this application is used as an electron transport material in a hybrid host material, it can improve the charge carrier balance in the luminescent layer, broaden the charge carrier recombination region, improve exciton generation and utilization efficiency, and improve the luminescent efficiency and lifetime of the device. Attached Figure Description

[0015] The accompanying drawings are provided to further understand this application and form part of the specification. They are used together with the following detailed description to explain this application, but do not constitute a limitation thereof.

[0016] Figure 1 This is a schematic diagram of the structure of an organic electroluminescent device according to one embodiment of this application.

[0017] Figure 2 This is a schematic diagram of the structure of an electronic device according to one embodiment of this application.

[0018] Figure Labels

[0019] 100, Anode 200, Cathode 300, Functional Layer 310, Hole Injection Layer

[0020] 321. First hole transport layer; 322. Light emission adjustment layer; 320. Hole transport layer; 330. Organic light emission layer.

[0021] 340, Electron transport layer; 350, Electron injection layer; 400, Electronic device Detailed Implementation

[0022] Exemplary embodiments will now be described more fully with reference to the accompanying drawings. However, exemplary embodiments can be implemented in many forms and should not be construed as limited to the examples set forth herein; rather, these embodiments are provided to make this application more comprehensive and complete, and to fully convey the concept of exemplary embodiments 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, numerous specific details are provided to give a full understanding of embodiments of this application.

[0023] According to a first aspect of this application, an organic compound is provided having a structure as shown in Formula 1:

[0024]

[0025] Among them, L, L1 and L2 may be the same or different, and each is independently selected from single bonds, substituted or unsubstituted aryl groups with 6 to 30 carbon atoms, and substituted or unsubstituted heteroaryl groups with 3 to 30 carbon atoms.

[0026] The substituents in L, L1, and L2 may be the same or different, and each is independently selected from deuterium, cyano, halogen group, alkyl with 1 to 10 carbon atoms, haloalkyl with 1 to 10 carbon atoms, deuterated alkyl with 1 to 10 carbon atoms, trialkylsilyl with 3 to 12 carbon atoms, aryl with 6 to 20 carbon atoms, deuterated aryl with 6 to 20 carbon atoms, heteroaryl with 3 to 20 carbon atoms, or cycloalkyl with 5 to 10 carbon atoms;

[0027] Ar1 and Ar2 may be the same or different, and each is independently selected from substituted or unsubstituted aryl groups with 6 to 30 carbon atoms, or substituted or unsubstituted heteroaryl groups with 3 to 30 carbon atoms.

[0028] The substituents in Ar1 and Ar2 may be the same or different, and each is independently selected from hydrogen, deuterium, cyano, halogen group, alkyl with 1 to 10 carbon atoms, haloalkyl with 1 to 10 carbon atoms, deuteralkyl with 1 to 10 carbon atoms, trialkylsilyl with 3 to 12 carbon atoms, aryl with 6 to 20 carbon atoms, deuterylaryl with 6 to 20 carbon atoms, heteroaryl with 3 to 20 carbon atoms, or cycloalkyl with 5 to 10 carbon atoms; optionally, any two adjacent substituents form a saturated or unsaturated 5 to 13-membered ring.

[0029] In this application, saturated or unsaturated 5- to 13-membered rings refer to carbon rings or heterocycles 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.

[0030] In this application, the terms "optional" and "optionally" mean that the events or circumstances described below may or may not occur. For example, "optionally, any two adjacent substituents form a saturated or unsaturated 3- to 15-membered ring" includes: the scenario where any two adjacent substituents form a ring, and the scenario where any two adjacent substituents exist independently without forming a ring. "Any two adjacent" can include having two substituents on the same atom, and can also include having one substituent on each of two adjacent atoms; wherein, when there are two substituents on the same atom, the two substituents can form a saturated or unsaturated spirocyclic ring with the atom they are connected to; when there is one substituent on each of two adjacent atoms, the two substituents can fuse into a ring.

[0031] In this application, the descriptive phrases "each...independently is," "...each independently is," and "...each independently is" are interchangeable and should be interpreted broadly. They can mean either that the specific options expressed by the same symbol in different groups do not affect each other, or that the specific options expressed by the same symbol in the same group do not affect each other. For example, In this formula, each q is independently 0, 1, 2 or 3, and each R is independently selected from hydrogen, deuterium, fluorine or chlorine. The meaning is as follows: Formula Q-1 indicates that there are q substituents R on the benzene ring. Each R can be the same or different, and the options of each R do not affect each other. Formula Q-2 indicates that there are q substituents R on each benzene ring of biphenyl. The number q of substituents R on the two benzene rings can be the same or different, and each R can be the same or different. The options of each R do not affect each other.

[0032] In this application, the term "substituted or unsubstituted" means that the functional group described after the term may or may not have substituents (hereinafter, for ease of description, 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 aforementioned substituents, i.e., Rc, can be, for example, deuterium, cyano, halogen groups, alkyl groups with 1 to 10 carbon atoms, haloalkyl groups with 1 to 10 carbon atoms, deuteryl groups with 1 to 10 carbon atoms, trialkylsilyl groups with 3 to 12 carbon atoms, aryl groups with 6 to 20 carbon atoms, deuteryl groups with 6 to 20 carbon atoms, heteroaryl groups with 3 to 20 carbon atoms, cycloalkyl groups with 3 to 10 carbon atoms, etc. The number of substituents can be one or more.

[0033] In this application, "multiple" means two or more, such as two, three, four, five, six, etc.

[0034] In this application, the number of carbon atoms in substituted or unsubstituted functional groups refers to the total number of carbon atoms.

[0035] The hydrogen atoms in the compound structure of this application include various isotopes of hydrogen, such as hydrogen (H), deuterium (D), or tritium (T).

[0036] In the structural formula of the compound in this application, "D" indicates deuteration.

[0037] In this application, aryl refers to any optional functional group or substituent derived from an aromatic carbon ring. The aryl group can be a monocyclic aryl (e.g., phenyl) or a polycyclic aryl; in other words, the aryl group can be a monocyclic aryl, a fused-ring aryl, two or more monocyclic aryl groups linked by carbon-carbon bonds, a monocyclic aryl and a fused-ring aryl linked by carbon-carbon bonds, or two or more fused-ring aryl groups linked by carbon-carbon bonds. That is, unless otherwise stated, two or more aromatic groups linked by carbon-carbon bonds can also be considered as the aryl group in this application. Fused-ring aryl groups may include, for example, bicyclic fused aryl (e.g., naphthyl), tricyclic fused aryl (e.g., phenanthrene, fluorene, anthracene), 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, spirodifluorenyl, anthracene, phenanthryl, biphenyl, terphenyl, triphenylene, perylene, benzo[9,10]phenanthryl, pyrene, benzofluoranthryl, etc. Base, etc.

[0038] In this application, the term "arylene" refers to a divalent or polyvalent group formed by the further loss of one or more hydrogen atoms from an aryl group.

[0039] In this application, terphenyl includes

[0040] In this application, the substituted or unsubstituted aryl (arylene) group can have 6, 10, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39, or 40 carbon atoms. In some embodiments, the substituted or unsubstituted aryl group is a substituted or unsubstituted aryl group with 6 to 30 carbon atoms; in other embodiments, it is a substituted or unsubstituted aryl group with 6 to 25 carbon atoms; in still other embodiments, it is a substituted or unsubstituted aryl group with 6 to 18 carbon atoms; and in yet another embodiment, it is a substituted or unsubstituted aryl group with 6 to 15 carbon atoms.

[0041] In this application, the fluorene group can be substituted by one or more substituents. When the fluorene group is substituted, the substituted fluorene group can be: etc., but not limited to this.

[0042] In this application, aryl groups used as substituents include, but are not limited to, phenyl, naphthyl, phenanthryl, biphenyl, fluorenyl, dimethylfluorenyl, etc.

[0043] In this application, a heteroaryl group refers to a monovalent aromatic ring or its derivative containing 1, 2, 3, 4, 5, or 6 heteroatoms. The heteroatoms can be one or more of B, O, N, P, Si, Se, and S. A heteroaryl group can be a monocyclic heteroaryl group or a polycyclic heteroaryl group. In other words, a heteroaryl group can be a single aromatic ring system or a system of multiple aromatic rings linked by carbon-carbon bonds, and any aromatic ring system can be an aromatic monocyclic ring or an aromatic fused ring. For example, heteroaryl groups may include, but are not limited to, thiopheneyl, furanyl, pyrrolyl, imidazolyl, thiazolyl, oxazolyl, oxadiazolyl, triazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, acridineyl, pyridazinyl, quinolinyl, quinazolinyl, quinoxazinyl, phenoxazinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, isoquinolinyl, indolyl, carbazoleyl, benzoxazolyl, benzoimidazolyl, benzothiazolyl, benzocarbazoleyl, benzothiaphenyl, dibenzothiaphenyl, thiaphenothiaphenyl, benzofuranyl, phenanthrololinyl, isoxazolyl, thiadiazolyl, phenthiaazinyl, silfluorenyl, dibenzofuranyl, and N-phenylcarbazoleyl, N-pyridylcarbazoleyl, N-methylcarbazoleyl, etc.

[0044] In this application, the term "hybrid aryl" refers to a divalent or polyvalent group formed by the further loss of one or more hydrogen atoms from a heteroaryl group.

[0045] In this application, the number of carbon atoms in the substituted or unsubstituted heteroaryl (hybrid aryl) can be selected from 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39, or 40. In some embodiments, the substituted or unsubstituted heteroaryl is a substituted or unsubstituted heteroaryl with a total carbon number of 3 to 30; in other embodiments, the substituted or unsubstituted heteroaryl is a substituted or unsubstituted heteroaryl with a total carbon number of 12 to 18; and in still other embodiments, the substituted or unsubstituted heteroaryl is a substituted or unsubstituted heteroaryl with a total carbon number of 5 to 12.

[0046] In this application, the heteroaryl groups used as substituents include, but are not limited to, pyridyl, carbazolyl, dibenzothiophene, dibenzofuranyl, benzoxazolyl, benzothiazolyl, and benzimidazolyl.

[0047] In this application, the substituted heteroaryl group may be one or more hydrogen atoms of the heteroaryl group that are replaced by groups such as deuterium, halogen group, cyano, aryl, heteroaryl, trialkylsilyl, alkyl, cycloalkyl, haloalkyl, etc.

[0048] In this application, alkyl groups having 1 to 10 carbon atoms can include straight-chain alkyl groups having 1 to 10 carbon atoms and branched alkyl groups having 3 to 10 carbon atoms. The number of carbon atoms in an alkyl group can be, for example, 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10. Specific examples of alkyl groups include, but are not limited to, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl, neopentyl, and n-hexyl.

[0049] In this application, the halogen group may be, for example, fluorine, chlorine, bromine, or iodine.

[0050] In this application, specific examples of trialkylsilyl groups include, but are not limited to, trimethylsilyl, triethylsilyl, etc.

[0051] In this application, specific examples of alkyl halogens include, but are not limited to, trifluoromethyl.

[0052] In this application, the number of carbon atoms in cycloalkyl groups with 3 to 10 carbon atoms can be, for example, 3, 4, 5, 6, 7, 8, or 10. Specific examples of cycloalkyl groups include, but are not limited to, cyclopentyl, cyclohexyl, and adamantyl.

[0053] In this application, the number of carbon atoms in the deuterated alkyl group is, for example, 1, 2, 3, 4, 5, 6, 7, 8, or 10. Specific examples of deuterated alkyl groups include, but are not limited to, trideuterated methyl.

[0054] In this application, the number of carbon atoms in the alkyl halogroup is, for example, 1, 2, 3, 4, 5, 6, 7, 8, or 10. Specific examples of alkyl halogroups include, but are not limited to, trifluoromethyl.

[0055] In this application, a ring system formed by n atoms is called an n-membered ring. For example, phenyl is a 6-membered ring. 5- to 13-membered rings refer to cyclic groups having 5 to 13 ring atoms. Examples of 5- to 13-membered rings include cyclopentane, cyclohexane, benzene rings, and fluorene rings.

[0056] In this application, It refers to the chemical bond that connects with other groups.

[0057] In this application, the non-positioned connecting key refers to the single bond extending from the loop system. This indicates that one end of the linker can connect to any position in the ring system it traverses, and the other end connects to the rest of the compound molecule. For example, as shown in equation (f) below, the naphthyl group represented by equation (f) is connected to other positions in the molecule through two non-positional linkers that traverse the bicyclic ring. This means that any possible connection mode shown in equations (f-1) to (f-10) is included.

[0058]

[0059] For another example, as shown in equation (X'), the dibenzofuran group represented by equation (X') is connected to other positions in the molecule via a non-positional linker extending from the middle of one side of the benzene ring. This means that any possible connection mode shown in equations (X'-1) to (X'-4) is included.

[0060]

[0061] In this application, a non-orienting substituent refers to a substituent connected by a single bond extending from the center of the ring system, indicating that the substituent can be attached to any possible position in the ring system. For example, as shown in equation (Y) below, the substituent R' represented by equation (Y) is connected to the quinoline ring by a non-orienting linking bond, which means that it includes any possible connection mode shown in equations (Y-1) to (Y-7):

[0062]

[0063] In some embodiments, the organic compounds of this application are selected from the structures shown in formula (I-1), formula (I-2), or formula (I-3):

[0064]

[0065] In this application, L, L1, and L2 may be the same or different, and each is independently selected from: single bonds, substituted or unsubstituted aryl groups 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 substituted or unsubstituted heteroaryl groups 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.

[0066] In some embodiments, L, L1, and L2 may be the same or different, and each is independently selected from single bonds, substituted or unsubstituted aryl groups with 6 to 18 carbon atoms, and substituted or unsubstituted heteroaryl groups with 5 to 18 carbon atoms.

[0067] Optionally, the substituents in L, L1 and L2 are each independently selected from deuterium, fluorine, cyano, alkyl with 1 to 4 carbon atoms, haloalkyl with 1 to 4 carbon atoms, deuterated alkyl with 1 to 4 carbon atoms, trialkylsilyl with 3 to 7 carbon atoms, aryl with 6 to 12 carbon atoms or deuterated aryl with 6 to 12 carbon atoms.

[0068] In some embodiments, L, L1, and L2 may be the same or different, and each independently represents a single bond, a substituted or unsubstituted phenylene, a substituted or unsubstituted naphthylene, a substituted or unsubstituted biphenylene, a substituted or unsubstituted phenanthylene, a substituted or unsubstituted fluorene, a substituted or unsubstituted pyridylene, a substituted or unsubstituted dibenzofuranylene, a substituted or unsubstituted dibenzothiopheneylene, or a substituted or unsubstituted carbazolylene.

[0069] Optionally, the substituents in L, L1 and L2 are each independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trimethylsilyl, trideuterated methyl, pentadeuterated phenyl, phenyl or naphthyl.

[0070] In some embodiments, L1 and L2 are each independently selected from the group consisting of single bonds or the following groups:

[0071]

[0072] In some embodiments, L is selected from the group consisting of single bonds or the following groups:

[0073]

[0074] In some embodiments, L1 and L2 may be the same or different, and each is independently selected from the group consisting of single bonds or the following groups:

[0075]

[0076] In some embodiments, L is selected from the group consisting of single bonds or the following groups:

[0077]

[0078] In some embodiments, Ar1 and Ar2 may be the same or different, and each is independently selected from substituted or unsubstituted aryl groups 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 substituted or unsubstituted heteroaryl groups having 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.

[0079] In some embodiments, Ar1 and Ar2 may be the same or different, and each is independently selected from substituted or unsubstituted aryl groups having 6 to 25 carbon atoms or substituted or unsubstituted heteroaryl groups having 12 to 18 carbon atoms.

[0080] Optionally, the substituents in Ar1 and Ar2 are each independently selected from deuterium, halogen groups, cyano, haloalkyl with 1 to 4 carbon atoms, deuteralkyl with 1 to 4 carbon atoms, alkyl with 1 to 4 carbon atoms, cycloalkyl with 5 to 10 carbon atoms, aryl with 6 to 15 carbon atoms, heteroaryl with 5 to 12 carbon atoms, trialkylsilyl with 3 to 7 carbon atoms, or deuteralkylaryl with 6 to 15 carbon atoms. Optionally, any two adjacent substituents form a benzene ring or a fluorene ring.

[0081] In some embodiments, Ar1 and Ar2 may be the same or different, and each is 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 phenanthyl, substituted or unsubstituted anthraquinyl, substituted or unsubstituted pyrene, substituted or unsubstituted triphenylene, substituted or unsubstituted spirodifluorenyl, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted dibenzofuranyl, and substituted or unsubstituted carbazole.

[0082] In some embodiments, the substituents in Ar1 and Ar2 may be the same or different, and each is independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, trideuterated methyl, trimethylsilyl, pentadeuterated phenyl, phenyl or naphthyl.

[0083] In some embodiments, Ar1 and Ar2 may be the same or different, and each is independently selected from the following groups:

[0084]

[0085] In some embodiments, Ar1 and Ar2 may be the same or different, and each is independently selected from the following groups:

[0086]

[0087]

[0088] In some implementations... They may be the same or different, and each is independently selected from the following groups:

[0089]

[0090] In some more specific implementations Selected from the following groups:

[0091]

[0092] Selected from the following groups:

[0093]

[0094]

[0095] In some implementations, in Formula 1 Selected from the following groups:

[0096]

[0097]

[0098] In some embodiments, the organic compounds of this application are selected from the group consisting of:

[0099]

[0100]

[0101]

[0102]

[0103]

[0104]

[0105]

[0106]

[0107]

[0108]

[0109] A second aspect of this application provides an organic electroluminescent device, including an anode, a cathode, and a functional layer disposed between the anode and the cathode; wherein the functional layer comprises the organic compound described in the first aspect of this application.

[0110] The organic compounds provided in this application can be used to form at least one organic film layer in the functional layer to improve the luminous efficiency and lifetime of organic electroluminescent devices.

[0111] Optionally, the functional layer includes an organic light-emitting layer, which comprises the organic compound. The organic light-emitting layer may be composed of the organic compound provided in this application, or it may be composed of the organic compound provided in this application and other materials.

[0112] According to one specific embodiment, the organic electroluminescent device, such as Figure 1 As shown, an organic electroluminescent device may include an anode 100, a hole injection layer 310, a first hole transport layer 321, a light-emitting adjustment layer (also called 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, which are stacked sequentially.

[0113] In this 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 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. Preferably, a transparent electrode comprising indium tin oxide (ITO) as the anode is included.

[0114] In this application, the first hole transport layer or the luminescence adjustment layer may each include one or more hole transport materials. The hole transport layer material may be selected from carbazole polymers, carbazole-linked triarylamine compounds, or other types of compounds, specifically from the compounds listed below or any combination thereof:

[0115]

[0116] In one embodiment, the first hole transport layer 321 is composed of HT-1.

[0117] In one embodiment, the light-emitting adjustment layer 322 is composed of HT-2.

[0118] Optionally, a hole injection layer 310 is further provided between the anode 100 and the first hole transport layer 321 to enhance the ability to inject holes into the first hole transport layer 321. The hole injection layer 310 can be selected from benzidine derivatives, starburst-like aryl amine compounds, phthalocyanine derivatives, or other materials; this application does not impose any special limitations on this. The material of the hole injection layer 310 can, for example, be selected from the following compounds or any combination thereof;

[0119]

[0120] In one embodiment of this application, the hole injection layer 310 is composed of PD and HT-1.

[0121] Optionally, the organic light-emitting layer 330 may include the host material and the guest material. Optionally, the organic light-emitting layer 330 is composed of a host material and a guest material. Holes and electrons injected into the organic light-emitting layer 330 can recombine in the organic light-emitting layer 330 to form excitons. The excitons transfer energy to the host material, and the host material transfers energy to the guest material, thereby enabling the guest material to emit light.

[0122] The host material of the organic light-emitting layer 330 may include metal chelating compounds, bis(styrene) derivatives, aromatic amine derivatives, dibenzofuran derivatives, or other types of materials. Optionally, the host material may include the organic compounds of this application.

[0123] The guest material of the organic light-emitting layer 330 can be a compound or its derivative having a condensed aryl ring, a compound or its derivative having a heteroaryl ring, an aromatic amine derivative, or other materials; this application does not impose any special limitations on this. The guest material is also called a dopant or dopant. According to the type of light emission, it can be divided into fluorescent dopant and phosphorescent dopant. For example, specific examples of phosphorescent dopant include, but are not limited to,

[0124] [Ir(flq)2(acac)]

[0125] (Ir(Mphq)3), (RD).

[0126] In one embodiment of this 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 is composed of the organic compound. The guest material may be, for example, RD.

[0127] In another embodiment, the host material of the organic light-emitting layer 330 comprises the organic compound of this application and RH-P. The object material is, for example, RD.

[0128] In one embodiment of this 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 comprises the organic compound of this application. The guest material is, for example, fac-Ir(ppy)3.

[0129] 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. These electron transport materials can be selected from, but are not limited to, BmPyPhB, LiQ, benzimidazole derivatives, oxadiazole derivatives, quinoxaline derivatives, triazine derivatives, etc., and this application does not impose any specific limitations on them. 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:

[0130]

[0131] (BmPyPhB) (ET-1).

[0132] In one embodiment of this application, the electron transport layer 340 is composed of ET-1 and LiQ.

[0133] In this application, the cathode 200 includes a cathode material that has a small work function and facilitates electron injection into the functional layers. 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 alloys thereof; or multilayer materials such as LiF / Al, Liq / Al, LiO2 / Al, LiF / Ca, LiF / Al, and BaF2 / Ca. Optionally, a metal electrode comprising magnesium and silver may be included as the cathode.

[0134] Optionally, an electron injection layer 350 is further disposed 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 complexes of alkali metals and organic materials. In one embodiment of this application, the electron injection layer 350 includes ytterbium (Yb).

[0135] This application not only provides the organic electroluminescent device comprising a compound represented by Formula 1 for an organic light-emitting layer, but also provides an electronic device comprising the organic electroluminescent device of this application.

[0136] According to one implementation method, such as Figure 2 As shown, the provided electronic device is electronic device 400. 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 including but not limited to computer screens, mobile phone screens, televisions, electronic paper, emergency lighting, optical modules, etc.

[0137] The following examples illustrate the synthesis method of the organic compounds of this application, but this disclosure is not limited thereto.

[0138] Synthesis Examples

[0139] Those skilled in the art will recognize that the chemical reactions described herein can be suitably used to prepare many of the heterocyclic compounds of this application, and other methods for preparing the compounds of this application are considered to be within the scope of this application. For example, the synthesis of those non-illustrative compounds according to this application can be successfully accomplished by those skilled in the art through modification methods, such as appropriately protecting interfering groups, utilizing other known reagents besides those described herein, or making some conventional modifications to the reaction conditions. Compounds for which synthetic methods are not mentioned in this application are commercially available starting materials.

[0140] Synthesis of Sub-a1:

[0141]

[0142] Under a nitrogen atmosphere, RM-1 (12.63 g, 50 mmol), pinacol diborate (14.0 g, 55 mmol), potassium acetate (10.8 g, 110 mmol), and 1,4-dioxane (160 mL) were added sequentially to a 500 mL three-necked flask. The mixture was stirred and heated until it reached 40 °C. Then, tris(dibenzylacetone)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. The mixture was then heated to reflux and stirred overnight. After the system cooled to room temperature, 200 mL of water was added to the system and stirred thoroughly for 30 min. The mixture was then 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, then dissolved in 200 mL of toluene and passed through a silica gel column to remove the catalyst. After concentration, a white solid Sub-a1 (12.56 g, yield 73%) was obtained.

[0143] Synthesis of Sub-b1:

[0144]

[0145] Under a nitrogen atmosphere, Sub-a1 (18.93 g, 55 mmol), RM-2 (10.97 g, 50 mmol), tetra(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 sequentially to a 500 mL three-necked flask. Stirring and heating were initiated, and the mixture was refluxed for 8 h. After cooling to room temperature, the mixture was extracted with dichloromethane (100 mL × 3 times). The organic phases were combined, dried over anhydrous magnesium sulfate, filtered, and the solvent was removed by vacuum distillation to obtain the crude product. The crude product was purified by silica gel column chromatography using dichloromethane / n-heptane as the mobile phase to obtain a white solid, Sub-b1 (11.42 g, yield 64%).

[0146] Referring to the synthesis of Sub-b1, Sub-b2 to Sub-b3 were synthesized by replacing Sub-a1 with reactant A as shown in Table 1 and replacing RM-2 with reactant B.

[0147] Table 1: Synthesis of Sub-b2 to Sub-b3

[0148]

[0149]

[0150] Synthesis of Sub-c1:

[0151]

[0152] Under a nitrogen atmosphere, (methoxymethyl)triphenylphosphonium chloride (51.25 g, 149.5 mmol) and anhydrous tetrahydrofuran (230 mL) were added to a 1000 mL three-necked flask. The system was cooled to -15 °C and maintained for 30 min. Then, Sub-a1 (46.38 g, 130 mmol) was weighed and dissolved in anhydrous tetrahydrofuran (230 mL). This solution was slowly added dropwise to the reaction system using a constant pressure dropping funnel, maintaining the temperature at -15 °C during the addition. After the addition was completed, the reaction was stirred at -15 °C for 1 h. The reaction system was then allowed to warm naturally to room temperature and extracted with dichloromethane (200 mL × 3 times). The organic phases were combined, dried over anhydrous magnesium sulfate, filtered, and the solvent was removed by vacuum distillation to obtain the crude product. The crude product was purified by silica gel column chromatography using n-heptane / dichloromethane as the mobile phase to obtain a grayish-white solid Sub-c1 (39.52 g, yield 79%).

[0153] Sub-c2 to Sub-c3 were synthesized by replacing Sub-b1 with reactant C as shown in Table 2, referring to Sub-c1.

[0154] Table 2: Synthesis of Sub-c2 to Sub-c3

[0155]

[0156] Synthesis of Sub-d1:

[0157]

[0158] Under a nitrogen atmosphere, Sub-c1 (45.80 g, 119 mmol), Eaton reagent (4.5 mL), and chlorobenzene (500 mL) were added sequentially to a 1000 mL three-necked flask. The mixture was heated to reflux and stirred for 4 h. After the reaction system cooled to room temperature, the reaction solution was poured into 1000 mL of deionized water, neutralized with saturated sodium hydroxide solution, and then extracted with dichloromethane (250 mL × 3 times). The organic phases were combined, dried over anhydrous magnesium sulfate, filtered, and the solvent was removed by vacuum distillation to obtain the crude product. The crude product was purified by silica gel column chromatography using dichloromethane / n-heptane as the mobile phase to obtain a white solid Sub-d1 (26.87 g, yield 64%).

[0159] Referring to the synthesis of Sub-d1, Sub-d2 to Sub-d3 were synthesized by replacing Sub-c1 with reactant D shown in Table 3.

[0160] Table 3: Synthesis from Sub-d2 to Sub-d3

[0161]

[0162] Synthesis of Sub-e1:

[0163]

[0164] Under a nitrogen atmosphere, Sub-d1 (17.64 g, 50 mmol), pinacol diborate (14.0 g, 55 mmol), potassium acetate (10.8 g, 110 mmol), and 1,4-dioxane (180 mL) were added sequentially to a 500 mL three-necked flask. The mixture was stirred and heated until it reached 40 °C. Then, 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. The mixture was then heated to reflux and stirred overnight. After the system cooled to room temperature, 200 mL of water was added to the system and stirred thoroughly for 30 min. The mixture was then 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, then dissolved in 200 mL of toluene and passed through a silica gel column to remove the catalyst. After concentration, a white solid Sub-e1 (16.66 g, yield 75%) was obtained.

[0165] Referring to the synthesis of Sub-e1, Sub-e2 to Sub-e3 were synthesized by replacing Sub-d1 with reactant E shown in Table 4.

[0166] Table 4: Synthesis of Sub-e2 to Sub-e3

[0167]

[0168] Synthesis of Sub-f1:

[0169]

[0170] Under a nitrogen atmosphere, RM-3 (13.89 g, 50 mmol), 4-chlorophenylboronic 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 added sequentially to a 500 mL three-necked flask. Stirring and heating were initiated, and the mixture was refluxed for 8 h. After cooling to room temperature, the mixture was extracted with dichloromethane (100 mL × 3 times). The organic phases were combined, dried over anhydrous magnesium sulfate, filtered, and the solvent was removed by vacuum distillation to obtain the crude product. The crude product was purified by silica gel column chromatography using dichloromethane / n-heptane as the mobile phase to obtain a white solid, Sub-f1 (14.50 g, yield 82%).

[0171] Referring to the synthesis of Sub-f1, reactant F shown in Table 5 was used to replace RM-3, and reactant G was used to replace 4-chlorophenylboronic acid to synthesize Sub-f2 to Sub-f10.

[0172] Table 5: Synthesis of Sub-f2 to Sub-f10

[0173]

[0174]

[0175] Synthesis Example 1: Synthesis of Compound 3

[0176]

[0177] Under a nitrogen atmosphere, Sub-e1 (11.66 g, 26.25 mmol), RM-4 (7.94 g, 25 mmol), palladium acetate (42 mg, 0.25 mmol), 2-dicyclohexylphosphine-2',4',6'-triisopropylbiphenyl (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 sequentially to a 250 mL three-necked flask. Stirring and heating were started, and the mixture was refluxed for 16 h. After the system cooled to room temperature, it was extracted with dichloromethane (100 mL × 3 times). The organic phases were combined, dried over anhydrous magnesium sulfate, filtered, and the solvent was removed by vacuum distillation to obtain the crude product. The crude product was purified by silica gel column chromatography using dichloromethane / n-heptane as the mobile phase to obtain a yellow-green solid compound 3 (10.80 g, yield 72%, m / z = 600.20 [M+H]). + ).

[0178] Referring to the synthesis of compound 3, reactant H was used instead of Sub-e1 and reactant J was used instead of RM-4 as shown in Table 6 to synthesize the compounds of this application in Table 6.

[0179] Table 6: Synthesis of the compounds in this application

[0180]

[0181]

[0182]

[0183]

[0184]

[0185]

[0186]

[0187]

[0188]

[0189]

[0190]

[0191] NMR data for some compounds:

[0192] Compound 9 NMR: 1 ¹H-NMR (400MHz, CD₂Cl₂) δppm: 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). Fabrication and evaluation of organic electroluminescent devices:

[0193] Example 1: Fabrication of a red organic electroluminescent device

[0194] 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.

[0195] 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. The first hole transport layer.

[0196] Compound HT-2 was vacuum-deposited onto the first hole transport layer to form a thickness of [missing information]. The light-emitting adjustment layer.

[0197] Next, on the second hole transport layer, compound 3:RH-P:RD was co-deposited in a ratio of 49%:49%:2% to form a layer with a thickness of [missing information]. The red light emitting layer (EML).

[0198] 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.

[0199] Furthermore, the vacuum evaporation thickness on the aforementioned cathode is [missing information]. The CP is used to complete the fabrication of a red organic electroluminescent device.

[0200] Examples 2-70

[0201] Except that, when fabricating the light-emitting layer, compound X in Table 7 is used instead of compound 1 in Example 1, the organic electroluminescent device is prepared using the same method as in Example 1.

[0202] Comparative Examples 1-4

[0203] Except that, when fabricating the light-emitting layer, compounds A, B, C, and D from Table 7 were used to replace compound 3 in Example 1, the organic electroluminescent device was prepared using the same method as in Example 1.

[0204] The compounds used in the preparation of the various examples and comparative examples have the following structures:

[0205]

[0206] The performance of the red organic electroluminescent devices prepared in Examples 1-70 and Comparative Examples 1-4 was tested, specifically at 10 mA / cm². 2 The IVL performance of the device was tested under the specified conditions. The lifetime of the T95 device was 20 mA / cm. 2 The test was conducted under the specified conditions, and the test results are shown in Table 7.

[0207] Table 7

[0208]

[0209]

[0210]

[0211]

[0212] Referring to Table 7 above, compared to Comparative Examples 1-4, when the compounds of the present invention are used as the host material for red organic electroluminescent devices, the luminous efficiency (Cd / A) of devices 1-70 is increased by at least 12.9%. 95 Life expectancy increased by at least 18.7%.

[0213] The preferred embodiments of the present invention have been described in detail above with reference to the accompanying drawings. However, the present invention is not limited to the specific details of the above embodiments. Within the scope of the technical concept of the present invention, various simple modifications can be made to the technical solution of the present invention, and these simple modifications all fall within the protection scope of the present invention.

Claims

1. Organic compound, characterized in that, The organic compound has the structure shown in Formula 1: Formula 1 Among them, L, L1 and L2 may be the same or different, and each is independently selected from single bonds, substituted or unsubstituted aryl groups with 6 to 18 carbon atoms, or substituted or unsubstituted heteroaryl groups with 5 to 18 carbon atoms. The substituents in L, L1 and L2 may be the same or different, and each is independently selected from deuterium, cyano, halogen group, alkyl with 1 to 10 carbon atoms, haloalkyl with 1 to 10 carbon atoms, deuteralkyl with 1 to 10 carbon atoms or trialkylsilyl with 3 to 12 carbon atoms. Ar1 and Ar2 may be the same or different, and each is independently selected from substituted or unsubstituted aryl groups with 6 to 30 carbon atoms, or substituted or unsubstituted heteroaryl groups with 3 to 30 carbon atoms; The substituents in Ar1 and Ar2 may be the same or different, and each is independently selected from deuterium, cyano, halogen group, alkyl with 1 to 10 carbon atoms, haloalkyl with 1 to 10 carbon atoms, deuteralkyl with 1 to 10 carbon atoms, or trialkylsilyl with 3 to 12 carbon atoms.

2. The organic compound according to claim 1, wherein L, L1, and L2 may be the same or different, and each is independently selected from a single bond, substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted biphenylene, substituted or unsubstituted phenanthylene, substituted or unsubstituted fluorene, substituted or unsubstituted pyridylene, substituted or unsubstituted dibenzofuranylene, substituted or unsubstituted dibenzothiopheneylene, or substituted or unsubstituted carbazolylene; The substituents in L, L1, and L2 are each independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trimethylsilyl, or trideuterated methyl.

3. The organic compound according to claim 1, wherein L1 and L2 are each independently selected from the group consisting of single bonds or the following groups: 。 4. The organic compound according to claim 3, wherein L is selected from the group consisting of single bonds or the following groups: 。 5. The organic compound according to claim 1, wherein Ar1 and Ar2 may be the same or different, and each is 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 phenanthyl, substituted or unsubstituted anthraquinyl, substituted or unsubstituted pyrene, substituted or unsubstituted triphenylene, substituted or unsubstituted spirodifluorenyl, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted dibenzofuranyl, or substituted or unsubstituted carbazolyl; The substituents in Ar1 and Ar2 may be the same or different, and each is independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, trideuterated methyl or trimethylsilyl.

6. The organic compound according to claim 1, wherein Ar1 and Ar2 may be the same or different, and each is independently selected from the following groups: 。 7. The organic compound according to claim 1, wherein and They may be the same or different, and each is independently selected from the following groups: 。 8. The organic compound according to claim 1, wherein in formula 1 is selected from the group consisting of 。 9. The organic compound according to claim 1, wherein selected from the group consisting of: ； Selected from the following groups: 。 10. Organic compound characterized in that, The organic compounds are selected from the group consisting of the following compounds: 。 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; The functional layer includes an organic light-emitting layer, which contains the organic compound.

12. An electronic device, characterized by Including the organic electroluminescent device as described in claim 11.

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