Organic compounds, organic electroluminescent devices and electronic devices comprising the same

Abstract

The application relates to the technical field of organic electroluminescent materials, and provides an organic compound, an organic electroluminescent device and an electronic device. The organic compound has a structure as shown in formula I, and the performance of the device can be significantly improved.

Description

Technical Field

[0001] This application relates to the field of organic electroluminescent materials technology, and more specifically to an organic compound and organic electroluminescent devices and electronic devices comprising the same. Background Technology

[0002] With the rapid development of organic synthesis and materials science, organic light-emitting diode (OLED) display technology has already been applied in smartphones, tablets, and other fields, and will further expand to large-size applications such as televisions. The optoelectronic functional materials used in OLED devices can be classified into charge injection transport materials and light-emitting materials based on their applications. According to the function of each layer, charge injection transport materials can also be divided into electron injection transport materials, electron blocking materials, hole injection transport materials, and hole blocking materials. Therefore, the optoelectronic functional material films constituting OLED devices must include at least two layers. Industrially applied OLED device structures include various layers such as hole injection layers, hole transport layers, electron blocking layers, light-emitting layers, hole blocking layers, electron transport layers, and electron injection layers, exhibiting richness and diversity in material types and combinations. Furthermore, the optoelectronic functional materials used in different OLED device structures exhibit strong selectivity; the same material may perform completely differently in different structural devices.

[0003] Generally, in a host material / dopant system, the choice of host material is crucial because it significantly impacts the efficiency and lifetime of the light-emitting device. A high-performance host material should possess a suitable molecular weight, high glass transition temperature and thermal decomposition temperature, high electrochemical stability, and good interfacial contact with adjacent functional layer materials. For the light-emitting host material, good carrier transport capability and a suitable triplet energy level are required to ensure efficient energy transfer from the host material to the guest material during luminescence, thereby achieving high device efficiency.

[0004] The main problems with existing organic electroluminescent devices are lifespan and efficiency. As displays become larger, driving voltages also increase, and luminous efficiency and current efficiency need to be improved. Therefore, it is necessary to continue to develop new materials to further improve the performance of organic electroluminescent devices. Summary of the Invention

[0005] In view of the above-mentioned problems 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 use of the organic compound in the organic electroluminescent device can improve the performance of the device.

[0006] A first aspect of this application provides an organic compound having the structure shown in Formula 1:

[0007]

[0008] Where X and Y are selected from single bonds, O or S, and one of X and Y is selected from O or S, and the other is a single bond;

[0009] 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.

[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 L, L1, L2, Ar1, and Ar2 may be the same or different, and each is independently selected from deuterium, cyano, halogen groups, alkyl groups with 1 to 10 carbon atoms, haloalkyl groups with 1 to 10 carbon atoms, deuteralkyl groups with 1 to 10 carbon atoms, trialkylsilyl groups with 3 to 12 carbon atoms, aryl groups with 6 to 20 carbon atoms, or heteroaryl groups with 3 to 20 carbon atoms.

[0012] A second aspect of this application provides an organic electroluminescent device, including an anode and a cathode disposed opposite to each other, and a functional layer disposed between the anode and the cathode; the functional layer comprises the aforementioned organic compound.

[0013] A third aspect of this application provides an electronic device including the organic electroluminescent device described in the second aspect.

[0014] The compounds in this application are phenanthrene-based. Based on this, a phenanthrene-based electron-deficient heteroaryl group is formed by fused benzofuran or benzothiophene at positions 1 and 2, and a triazine-based electron-deficient heteroaryl group is attached at position 3, serving as an electron-transporting red light host material. First, the phenanthrene-based electron-deficient benzofuran or benzothiophene core at positions 1 and 2 possesses a suitable first excited triplet energy level, making it suitable as a fragment for the luminescent host material. Second, the large conjugated area of ​​the core, and the presence of lone pairs of electrons on the oxygen or sulfur atoms in the core, significantly enhance the carrier transport performance of the target compound. Third, the presence of lone pairs of electrons on the triazine-based electron-deficient heteroaryl group at position 3, along with its adjacent hydrogen and oxygen / sulfur atoms, results in greater molecular twist, endowing the compound with good film-forming properties. Therefore, when this compound is used as an electron-transporting host material in a hybrid red light host material, it can improve the 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. 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. Hole transport layer; 322. Electron blocking layer; 330. Organic light-emitting layer; 340. Electron transport layer;

[0021] 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] In a first aspect, this application provides a compound having the structure shown in Formula I:

[0024]

[0025] Where X and Y are selected from single bonds, O or S, and one of X and Y is selected from O or S, and the other is a single bond;

[0026] 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.

[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 L, L1, L2, 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, deuterated alkyl with 1 to 10 carbon atoms, trialkylsilyl with 3 to 12 carbon atoms, aryl with 6 to 20 carbon atoms, or heteroaryl with 3 to 20 carbon atoms.

[0029] In this application, X and Y are selected from single bonds, O, or S; and one of X and Y is selected from O or S, and the other is a single bond, that is, when X is O, Y is a single bond; when X is S, Y is a single bond; when Y is O, X is a single bond; when Y is S, X is a single bond.

[0030] 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.

[0031] 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, halogen groups, cyano, alkyl, cycloalkyl, aryl, heteroaryl, deuterated aryl, haloaryl, trialkylsilyl, haloalkyl, or deuterated alkyl, etc. The number of substituents Rc can be one or more. When two substituents Rc are attached to the same atom, these two substituents Rc can exist independently or be connected to each other to form a ring with the atom; when two adjacent substituents Rc exist on a functional group, the adjacent substituents Rc can exist independently or fuse with the functional group to which they are attached to form a ring.

[0032] In this application, "multiple" means two or more, such as two, three, four, five, six, etc.

[0033] The hydrogen atoms in the compound structure of this application include various isotopes of hydrogen, such as hydrogen (H), deuterium (D) or tritium (T).

[0034] In this application, the number of carbon atoms in substituted or unsubstituted functional groups refers to the total number of carbon atoms. For example, if L1 is a substituted arylene with 12 carbon atoms, then the total number of carbon atoms in the arylene and its substituents is 12.

[0035] In this application, aryl refers to any optional functional group or substituent derived from an aromatic carbon ring. An aryl group can be a monocyclic aryl (e.g., phenyl) or a polycyclic aryl; in other words, an aryl group can be a monocyclic aryl, a fused-ring aryl, two or more monocyclic aryl groups conjugated by carbon-carbon bonds, a monocyclic aryl and a fused-ring aryl group conjugated by carbon-carbon bonds, or two or more fused-ring aryl groups conjugated by carbon-carbon bonds. That is, unless otherwise stated, two or more aromatic groups conjugated by carbon-carbon bonds can also be considered as aryl groups 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 may 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.

[0036] In this application, the term arylene refers to a divalent group formed by the further loss of one or more hydrogen atoms from an aryl group.

[0037] In this application, the substituted aryl group can be one or more hydrogen atoms of the aryl group that are replaced by groups such as deuterium, halogen groups, cyano, aryl, heteroaryl, trialkylsilyl, alkyl, cycloalkyl, haloalkyl, deuteralkyl, haloaryl, deuteryl, etc. It should be understood that the number of carbon atoms in the substituted aryl group refers to the total number of carbon atoms of the aryl group and the substituents on the aryl group. For example, a substituted aryl group with 18 carbon atoms means that the total number of carbon atoms of the aryl group and the substituents is 18.

[0038] 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.

[0039] In this application, a heteroaryl group refers to a monovalent aromatic ring or its derivative containing 1, 2, 3, 4, 5, 6, or 7 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 connected by carbon-carbon bonds in a conjugated manner. Each 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. Among them, thienyl, furanyl, and phenanthroline are heteroaryl groups of the single aromatic ring type, while N-phenylcarbazolyl and N-pyridylcarbazolyl are heteroaryl groups of the polycyclic system type connected by carbon-carbon bonds.

[0040] In this application, the term "hybrid aryl" refers to a divalent group formed by the further loss of one or more hydrogen atoms from a heteroaryl group.

[0041] In this application, the substituted heteroaryl group can be one or more hydrogen atoms of the heteroaryl group that are substituted by groups such as deuterium, halogen groups, cyano, aryl, heteroaryl, trialkylsilyl, alkyl, haloalkyl, deuteryl, haloaryl, and deuteryl. Specific examples of aryl-substituted heteroaryl groups include, but are not limited to, phenyl-substituted dibenzofuranyl, phenyl-substituted dibenzothiophenyl, and phenyl-substituted pyridyl. It should be understood that the number of carbon atoms in the substituted heteroaryl group refers to the total number of carbon atoms of the heteroaryl group and the substituents on the heteroaryl group.

[0042] In this application, the number of carbon atoms in the aryl group used as a substituent can be 6 to 20, for example, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, or 20. Specific examples of aryl groups used as substituents include, but are not limited to, phenyl, biphenyl, naphthyl, and anthracene. base.

[0043] In this application, the number of carbon atoms in the heteroaryl group used as a substituent can be 3 to 20, for example, the number of carbon atoms can be 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, or 20. Specific examples of heteroaryl groups used as substituents include, but are not limited to, pyridinyl, pyrimidinyl, carbazolyl, dibenzofuranyl, dibenzothiophenyl, quinolinyl, quinazolinyl, quinoxalinyl, and isoquinolinyl.

[0044] In this application, the number of carbon atoms in an alkyl group having 1 to 10 carbon atoms 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.

[0045] In this application, the halogen group may be, for example, fluorine, chlorine, bromine, or iodine.

[0046] In this application, specific examples of alkyl halides include, but are not limited to, trifluoromethyl.

[0047] In this application, specific examples of deuterated alkyl groups include, but are not limited to, trideuterated methyl groups.

[0048] In this application, specific examples of trialkylsilyl groups include, but are not limited to, trimethylsilyl, ethyldimethylsilyl, triethylsilyl, etc.

[0049] In this application, the single bond extending from the loop system is not located as a connecting bond. This means that one end of the linking bond can connect to any position in the ring system that the bond passes through, and the other end connects to the rest of the compound molecule.

[0050] 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 linkages that span the bicyclic ring. This means that any possible connection mode is shown in equations (f-1) to (f-10).

[0051]

[0052] For example, as shown in the following formula (X'), the dibenzofuran group represented by formula (X') is connected to other positions of the molecule through a non-positional linker extending from the middle of one side of the benzene ring. This means that any possible connection mode shown in formulas (X'-1) to (X'-4) is included.

[0053]

[0054] In this application, a non-positional 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-positional linking bond, which means that it includes any possible connection mode shown in equations (Y-1) to (Y-7).

[0055]

[0056] In some embodiments of this application, formula I is selected from the structure shown in formula I-1, formula I-2, formula I-3 or formula I-4:

[0057]

[0058] In some embodiments of this application, L, L1, and L2 may be the same or different, and each is independently selected from single-bonded substituted or unsubstituted aryl groups with 6 to 18 carbon atoms, or substituted or unsubstituted heteroaryl groups with 5 to 18 carbon atoms. For example, L, L1, and L2 may be the same or different, and each is independently selected from single-bonded substituted or unsubstituted aryl groups with 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, or 18 carbon atoms, or substituted or unsubstituted heteroaryl groups with 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, or 18 carbon atoms.

[0059] Optionally, the substituents in L, L1 and L2 are each independently selected from deuterium, fluorine, cyano, alkyl with 1 to 5 carbon atoms, trialkylsilyl with 3 to 8 carbon atoms, haloalkyl with 1 to 5 carbon atoms, deuterylalkyl with 1 to 5 carbon atoms or phenyl.

[0060] In some embodiments of this application, L, L1, and L2 may be the same or different, and each is independently selected from single bonds, substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted biphenylene, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted dibenzofuranyl, and substituted or unsubstituted carbazolyl.

[0061] Optionally, the substituents in L, L1 and L2 may be the same or different, and each may be independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, trideuterated methyl, trimethylsilyl or phenyl.

[0062] In some embodiments of this application, L, L1, and L2 may be the same or different, and each is independently selected from single bonds or the following groups:

[0063]

[0064] In some embodiments of this application, L is selected from the group consisting of single bonds or the following groups:

[0065]

[0066] In some embodiments of this application, 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:

[0067]

[0068] In some embodiments of this application, Ar1 and Ar2 are each independently selected from substituted or unsubstituted aryl groups having 6 to 20 carbon atoms, and substituted or unsubstituted heteroaryl groups having 12 to 18 carbon atoms. For example, Ar1 and Ar2 are each independently selected from substituted or unsubstituted aryl groups having 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19 or 20 carbon atoms, and substituted or unsubstituted heteroaryl groups having 12, 13, 14, 15, 16, 17 or 18 carbon atoms.

[0069] Optionally, the substituents in Ar1 and Ar2 are each independently selected from deuterium, halogen groups, cyano groups, alkyl groups with 1 to 5 carbon atoms, haloalkyl groups with 1 to 5 carbon atoms, deuteralkyl groups with 1 to 5 carbon atoms, trialkylsilyl groups with 3 to 8 carbon atoms, aryl groups with 6 to 12 carbon atoms, or heteroaryl groups with 5 to 12 carbon atoms.

[0070] In some embodiments of this application, Ar1 and Ar2 are each independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted phenanthyl, substituted or unsubstituted triphenylene, substituted or unsubstituted fluorenyl, substituted or unsubstituted spirodifluorenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, and substituted or unsubstituted carbazoleyl.

[0071] Optionally, the substituents in Ar1 and Ar2 are each independently selected from deuterium, fluorine, cyano, trideuterated methyl, trimethylsilyl, trifluoromethyl, methyl, ethyl, isopropyl, tert-butyl, phenyl, or naphthyl.

[0072] In some embodiments of this application, Ar1 and Ar2 may be the same or different, and each is independently selected from the group consisting of:

[0073]

[0074] Alternatively, Ar1 and Ar2 may be the same or different, and each may be independently selected from the group consisting of:

[0075]

[0076]

[0077] In some embodiments of this application, Each is independently selected from the group consisting of the following groups:

[0078]

[0079] In some embodiments of this application, Each is independently selected from the group consisting of the following groups:

[0080]

[0081]

[0082] In some embodiments of this application, the organic compounds of formula I are selected from the group consisting of the following compounds:

[0083]

[0084]

[0085]

[0086]

[0087]

[0088]

[0089]

[0090]

[0091]

[0092]

[0093] In a second aspect, 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.

[0094] The compounds provided in this application can be used to form at least one organic film layer in a functional layer to improve the current efficiency and lifetime of organic electroluminescent devices.

[0095] 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.

[0096] 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 transport layer 321, an electron blocking layer 322, an organic light-emitting layer 330, an electron transport layer 340, and a cathode 200, which are stacked sequentially.

[0097] 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.

[0098] In this application, the hole transport layer may 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:

[0099]

[0100] Those skilled in the art may refer to existing technologies for selection, and this application does not impose any special limitations in this regard.

[0101] In one embodiment of this application, the hole transport layer 321 is HT-1.

[0102] In one embodiment of this application, the electron blocking layer 322 is HT-2.

[0103] 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;

[0104]

[0105] In one embodiment of this application, the hole injection layer 310 is composed of PD and HT-1.

[0106] In this application, the organic light-emitting layer 330 can be composed of a single light-emitting material, or it can include a host material and a guest material. Optionally, the organic light-emitting layer 330 is composed of a host material and a guest material. 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.

[0107] The main material of the organic light-emitting layer 330 can include metal chelate compounds, bis(styrene) derivatives, aromatic amine derivatives, dibenzofuran derivatives, or other types of materials.

[0108] In some embodiments of this application, the host material of the organic light-emitting layer 330 is the compound of this application and RH-P.

[0109] The guest material of the organic light-emitting layer 330 can be a compound with a condensed aryl ring or its derivative, a compound with a heteroaryl ring or its derivative, 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. Specific examples of phosphorescent dopant include, but are not limited to,

[0110]

[0111] In one embodiment of this application, the organic electroluminescent device is a red organic electroluminescent device.

[0112] Example of object material: RD

[0113] 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. The electron transport materials can be selected from, but are not limited to, BTB, LiQ, ET-1, benzimidazole derivatives, oxadiazole derivatives, quinoxaline derivatives, or other electron transport materials. This application does not impose any specific limitations on these materials. The materials of the electron transport layer 340 include, but are not limited to, the following compounds:

[0114]

[0115] In one embodiment of this application, the electron transport layer 340 may be composed of ET-1 and LiQ.

[0116] In this application, the cathode 200 may include 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.

[0117] 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 may include LiQ.

[0118] Thirdly, this application provides an electronic device including the organic electroluminescent device described in the second aspect of this application.

[0119] According to one implementation method, such as Figure 2 As shown, the provided electronic device is electronic device 400, which includes the aforementioned organic electroluminescent device. 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.

[0120] The following examples illustrate the synthesis method of the compounds in this application, but this disclosure is not limited thereto.

[0121] Synthesis Examples

[0122] 1. Synthesis of intermediate Sub-a1:

[0123]

[0124] Under a nitrogen atmosphere, 3-bromo-1-chlorodibenzo[B,D]furan (19.70 g, 70 mmol) and dry tetrahydrofuran (200 mL) were added to a 500 mL three-necked flask. The system was cooled to -78 °C, and a solution of n-butyllithium (2.0 M n-hexane solution, 38.5 mL, 77 mmol) was added dropwise. After the addition was complete, the mixture was kept at -78 °C and stirred for 1 h. While maintaining the temperature at -78 °C, trimethyl borate (10.91 g, 105 mL) was added dropwise. After the addition of mol, the mixture was kept at -78℃ for 1 h, and then allowed to naturally warm to room temperature. Dilute hydrochloric acid (2M, 58mL) was added dropwise to the reaction solution and stirred for 30 min. The mixture was extracted with dichloromethane (100mL × 3 times), the organic phases were combined and dried over anhydrous magnesium sulfate, filtered, and the solvent was removed by vacuum distillation to obtain the crude product. The crude product was slurried with n-heptane and filtered to obtain the intermediate Sub-a1 (11.56g, yield 67%) as a white solid.

[0125] Intermediates Sub-a2 to Sub-a4, listed in Table 1, were synthesized using the same method as intermediate Sub-a1, except that reactant A was used instead of 3-bromo-1-chlorodibenzo[B,D]furan. The main starting materials used, the intermediates synthesized, and their yields are shown in Table 1.

[0126] Table 1

[0127]

[0128] 2. Synthesis of intermediate Sub-b1:

[0129]

[0130] Under a nitrogen atmosphere, o-bromobenzaldehyde (9.25 g, 50 mmol), intermediate Sub-a1 (13.55 g, 55 mmol), tetrakis(triphenylphosphine)palladium (0.58 g, 0.5 mmol), anhydrous sodium carbonate (10.60 g, 100 mmol), toluene (140 mL), anhydrous ethanol (35 mL), and deionized water (35 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 and dried over anhydrous magnesium sulfate. After filtration, 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 intermediate Sub-b1 (11.20 g, 73% yield) as a white solid.

[0131] Intermediates Sub-b2 to Sub-b4, listed in Table 2, were synthesized using the same method as intermediate Sub-b1, except that reactant B was used instead of intermediate Sub-a1. The main raw materials used, the intermediates synthesized, and their yields are shown in Table 2.

[0132] Table 2

[0133]

[0134] 3. Synthesis of intermediate Sub-c1:

[0135]

[0136] Under a nitrogen atmosphere, (methoxymethyl)triphenylphosphonium chloride (51.25 g, 149.5 mmol) and anhydrous tetrahydrofuran (200 mL) were added to a 1000 mL three-necked flask. The system was cooled to -15 °C and maintained for 30 min. Then, Sub-b1 (39.90 g, 130 mmol) was weighed and dissolved in anhydrous tetrahydrofuran (200 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, extracted with dichloromethane (200 mL × 3 times), the organic phases were combined and 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 the intermediate Sub-c1 (29.60 g, yield 68%) as a red solid.

[0137] Intermediates Sub-c2 to Sub-c4 listed in Table 3 were synthesized using the same method as intermediate Sub-c1, except that reactant C was used instead of intermediate Sub-b1. The main raw materials used, the intermediates synthesized, and their yields are shown in Table 3.

[0138] Table 3

[0139]

[0140] 4. Synthesis of intermediate Sub-d1:

[0141]

[0142] Under a nitrogen atmosphere, Sub-c1 (39.84 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 and dried over anhydrous magnesium sulfate. After filtration, 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 Sub-d1 (17.29 g, yield 48%) as a white solid.

[0143] Intermediates Sub-d2 to Sub-d4, listed in Table 4, were synthesized using the same method as intermediate Sub-d1, except that reactant D was used instead of intermediate Sub-c1. The main raw materials used, the intermediates synthesized, and their yields are shown in Table 4.

[0144] Table 4

[0145]

[0146] 5. Synthesis of intermediate Sub-e1:

[0147]

[0148] Under a nitrogen atmosphere, Sub-d1 (15.14 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 the mixture was 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, the intermediate Sub-e1 (13.21 g, yield 67%) was obtained as a white solid.

[0149] Intermediates Sub-e2 to Sub-e4, listed in Table 5, were synthesized using the same method as intermediate Sub-e1, except that reactant E was used instead of intermediate Sub-d1. The main starting materials used, the intermediates synthesized, and their yields are shown in Table 5.

[0150] Table 5

[0151]

[0152] 6. Synthesis of intermediate Sub-f1:

[0153]

[0154] Under a nitrogen atmosphere, 2-chloro-4-(1-naphthyl)-6-phenyl-1,3,5-triazine (15.94 g, 50 mmol), 3-chlorophenylboronic acid (8.60 g, 55 mmol), tetra(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 and dried over anhydrous magnesium sulfate. After filtration, 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 (15.36 g, 78% yield).

[0155] Intermediates Sub-f2 to Sub-f10 listed in Table 6 were synthesized using the same method as intermediate Sub-f1, except that reactant F was used instead of 2-chloro-4-(1-naphthyl)-6-phenyl-1,3,5-triazine, and reactant G was used instead of 3-chlorophenylboronic acid. The main raw materials used, the intermediates synthesized, and their yields are shown in Table 6.

[0156] Table 6

[0157]

[0158]

[0159] Synthesis Example 1: Synthesis of Compound 3:

[0160]

[0161] Under a nitrogen atmosphere, Sub-e1 (10.35 g, 26.25 mmol), 2-chloro-4-(2-naphthyl)-6-phenyl-1,3,5-triazine (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 and dried over anhydrous magnesium sulfate. After filtration, 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 compound 3 (9.20 g, yield 67%) as a yellow-green solid, mass spectrometry (m / z) = 550.19 [M+H]. + .

[0162] The compounds listed in Table 7 were synthesized using the same method as compound 3, except that reactant H was used instead of Sub-e1 and reactant J was used instead of 2-chloro-4-(2-naphthyl)-6-phenyl-1,3,5-triazine. The main starting materials used, the synthesized compounds, their mass spectra and yields are shown in Table 7.

[0163] Table 7

[0164]

[0165]

[0166]

[0167]

[0168]

[0169]

[0170]

[0171]

[0172]

[0173]

[0174]

[0175] NMR data for some compounds:

[0176] Compound 9 NMR: 1 H-NMR(400MHz,Methylene-Chloride-D2)δppm 9.41(s,1H),8.85(d,2H),8.79(d,1H),8.62(d,1H),8.35(d,1H),8.26(d,1H),8.17-8.09(m,2H),7.93(d,1H),7.75-7.45(m,13H).

[0177] NMR of compound 177: 1 H-NMR(400MHz,Methylene-Chloride-D2)δppm 9.54(s,1H),8.82(d,2H),8.71(d,1H),8.60(d,1H),8.33-8.24(m,3H),8.01-7.85(m,5H),7.80-7.69(m,3H),7.68-7.31(m,11H).

[0178] Fabrication and Evaluation Examples of Organic Electroluminescent Devices

[0179] Example 1: Fabrication of a red organic electroluminescent device

[0180] Anodizing pretreatment is performed through the following process: The thickness is sequentially... The ITO / Ag / ITO substrate was cut into dimensions of 40mm (length) × 40mm (width) × 0.7mm (thickness), and a photolithography process was used to prepare it into an experimental substrate with an anode and an insulating layer pattern. The surface was treated with ultraviolet ozone and O2:N2 plasma to increase the work function of the substrate anode.

[0181] On the experimental substrate (anode), PD:HT-1 was co-deposited at a deposition rate of 2%:98% to form a thickness of [missing information]. Hole injection layer.

[0182] Compound HT-1 was vacuum-deposited onto the hole injection layer to form a thickness of [thickness value missing]. The hole transport layer.

[0183] Compound HT-2 was vacuum-deposited onto the hole transport layer to form a thickness of [thickness value missing]. The electron blocking layer.

[0184] On the electron blocking layer, compounds 3∶RH-P∶RD were co-deposited in a ratio of 49%∶49%∶2% to form a thickness of The organic light-emitting layer.

[0185] On the organic light-emitting layer, compounds ET-1 and LiQ were co-deposited at a 1:1 evaporation rate ratio to form a layer with a thickness of [missing information]. The electron transport layer is formed by depositing Yb on it to create a thickness of [missing information]. An electron-injected layer was formed, and then magnesium (Mg) and silver (Ag) were deposited on the electron-injected layer at a evaporation rate of 1:9 to form a layer with a thickness of [missing information]. The cathode.

[0186] Finally, compound CP-1 is deposited on the cathode to form a thickness of [thickness value missing]. An organic coating layer is applied to complete the fabrication of a red organic electroluminescent device.

[0187] Examples 2-75

[0188] The organic electroluminescent device was prepared using the same method as in Example 1, except that the compound in Table 8 was used instead of compound 3 in Example 1 when forming the organic light-emitting layer.

[0189] Comparative Examples 1-3

[0190] Except that, when forming the organic light-emitting layer, compounds A, B, and C were used instead of compound 3 in Example 1, the organic electroluminescent device was prepared using the same method as in Example 1.

[0191] The main material structures used in the above embodiments and comparative examples are shown below:

[0192]

[0193]

[0194] The performance of the red organic electroluminescent devices prepared in Examples 1-75 and Comparative Examples 1-3 was tested, specifically at 10 mA / cm². 2 The IVL performance of the device was tested under the following conditions: T 95 Device lifetime is 20 mA / cm 2 The test was conducted under the specified conditions, and the test results are shown in Table 8.

[0195] Table 8

[0196]

[0197]

[0198] As can be seen from Table 8 above, when the compound of the present invention is used as the main material of a red organic electroluminescent device, the current efficiency is increased by at least 10.2% and the lifetime is increased by at least 12.3% compared with Comparative Examples 1 to 3.

[0199] Other embodiments of this application will readily occur to those skilled in the art upon consideration of the specification and practice of the invention disclosed herein. This application is intended to cover any variations, uses, or adaptations of this application that follow the general principles of this application and include common knowledge or customary techniques in the art not disclosed herein.

Claims

1. Organic compound, characterized in that, having a structure represented by Formula 1: wherein X and Y are selected from a single bond, O, or S, and one of X and Y is selected from O or S, and the other is a single bond; L, L1, and L2 are the same or different, and each is independently selected from a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted biphenylene group; the substituents in L, L1, and L2 are the same and selected from deuterium; Ar1and Ar2are each 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 phenanthryl group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, or a substituted or unsubstituted carbazolyl group; the substituents in Ar1and Ar2are each independently selected from deuterium, fluorine, cyano, or a phenyl group.

2. The organic compound according to claim 1, wherein Formula I is selected from the group consisting of Formula I-1, Formula I-2, Formula I-3, or Formula I-4:

3. The organic compound according to claim 1, wherein L, L1, and L2 are the same or different, and each is independently selected from a single bond or the following groups:

4. The organic compound according to claim 1, wherein Ar1and Ar2are the same or different, and each is independently selected from the group consisting of:

5. The organic compound according to claim 1, wherein the same or different and each independently selected from the group consisting of:

6. The organic compound according to claim 1, wherein the compound is selected from the following structures:

7. 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 6; the functional layer comprises an organic light-emitting layer, and the organic light-emitting layer comprises the organic compound; the organic electroluminescent device is a red organic electroluminescent device.

8. An electronic device, characterized by an organic electroluminescent device comprising the organic electroluminescent device according to claim 7.

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