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

Abstract

The application belongs to the technical field of organic electroluminescence, and provides an organic compound, an organic electroluminescent device containing the same and an electronic device. The organic compound has a structure shown in formula I. The organic electroluminescent device prepared by using the compound as an organic light-emitting layer has good photoelectric performance.

Description

TECHNICAL FIELD

[0001] The present application relates to the field of organic electroluminescence, in particular to an organic compound, an organic electroluminescence device comprising the same and an electronic device. BACKGROUND

[0002] With the development of electronic technology and the progress of material science, the application range of electronic components for realizing electroluminescence or photoelectric conversion is more and more extensive. An organic electroluminescence device, such as an organic light-emitting diode (OLED), generally comprises a cathode and an anode arranged oppositely, and a functional layer arranged between the cathode and the anode. The functional layer is composed of multiple organic or inorganic film layers, and generally comprises an organic light-emitting layer, a hole transport layer, an electron transport layer, etc. When a voltage is applied to the cathode and the anode, an electric field is generated between the two electrodes, under the action of the electric field, the electrons on the cathode side move to the electroluminescence layer, and the holes on the anode side also move to the electroluminescence layer, the electrons and the holes combine to form excitons in the electroluminescence layer, the excitons in the excited state release energy to the outside, and then the electroluminescence layer emits light.

[0003] At present, the material of the light-emitting layer is repeatedly charged and discharged in the use process, the material is easy to crystallize, the uniformity of the thin film is destroyed, and thus the service life of the material is affected. Therefore, it is necessary to develop stable and efficient organic materials, so as to reduce the driving voltage, improve the light-emitting efficiency of the device, and prolong the service life of the device, so as to further improve the performance of the organic electroluminescence device. SUMMARY

[0004] The purpose of the present application is to provide an organic compound, an organic electroluminescence device comprising the same and an electronic device, which is used in an organic electroluminescence device, and can improve the performance of the device.

[0005] According to a first aspect of the present application, an organic compound is provided, which has a structure shown in formula I:

[0006]

[0007] wherein X is N(R3), O or S, and R3 is selected from a substituted or unsubstituted phenyl group, a substituted or unsubstituted phenylene group;

[0008] each substituent on R3 is independently selected from deuterium, a cyano group, a halogen group, an alkyl group with 1-5 carbon atoms, a deuterated alkyl group with 1-5 carbon atoms, a deuterated aryl group with 6-12 carbon atoms, or an aryl group with 6-12 carbon atoms;

[0009] ring A is selected from an aromatic ring with 6-14 carbon atoms;

[0010] L1, L2, and L3 may be the same or different, and each is independently selected from single bonds, substituted or unsubstituted aryl groups with 6-30 carbon atoms, and substituted or unsubstituted heteroaryl groups with 3-30 carbon atoms.

[0011] Ar is selected from substituted or unsubstituted aryl groups with 6-30 carbon atoms and substituted or unsubstituted heteroaryl groups with 3-30 carbon atoms;

[0012] R1 and R2 may be the same or different, and each is independently selected from deuterium, halogen group, cyano, alkyl with 1-10 carbon atoms, cycloalkyl with 3-10 carbon atoms, haloalkyl with 1-10 carbon atoms, aryl with 6-20 carbon atoms, or heteroaryl with 3-20 carbon atoms.

[0013] n1 is the number of R1s, and n1 is selected from 0, 1, 2, 3 or 4; when n1 is greater than 1, any two R1s are the same or different.

[0014] n2 is the number of R2, and n2 is selected from 0, 1, 2, 3 or 4; when n2 is greater than 1, any two R2 are the same or different;

[0015] The substituents in L1, L2, L3, and Ar may be the same or different, and each is independently selected from deuterium, cyano, halogen group, alkyl with 1-10 carbon atoms, haloalkyl with 1-10 carbon atoms, deuterated alkyl with 1-10 carbon atoms, trialkylsilyl with 3-12 carbon atoms, deuterated aryl with 6-12 carbon atoms, aryl with 6-20 carbon atoms, or heteroaryl with 3-20 carbon atoms; optionally, any two adjacent substituents in Ar can form a saturated or unsaturated 3-15 membered ring.

[0016] 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.

[0017] According to a third aspect of this application, an electronic device is provided, including the organic electroluminescent device described in the second aspect.

[0018] In the molecular structure of the organic compound of this application, the heteroaromatic ring formed by the benzo[7]-membered heterocycle possesses large planar conjugation properties, which not only increases the glass transition temperature of the material but also enhances intermolecular conjugation, forming a deep HOMO and a high LUMO. Simultaneously, the N-bonding of the heteroaromatic ring with the indolecarbazole further increases molecular conjugation, effectively improving efficiency and thus enabling high-efficiency devices. Even at relatively low molecular weights, the organic compound of this application exhibits a high Tg, thus preventing recrystallization during actuation and demonstrating high stability. Therefore, depositing the compound of this application as an organic light-emitting layer material into an organic electroluminescent device can not only improve the device's luminous efficiency but also, to some extent, improve the operating voltage.

[0019] Other features and advantages of this application will be described in detail in the following detailed description section. Attached Figure Description

[0020] 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.

[0021] Figure 1 This is a schematic diagram of the structure of an organic electroluminescent device according to one embodiment of this application.

[0022] Figure 2 This is a schematic diagram of the structure of an electronic device according to one embodiment of this application.

[0023] Figure Labels

[0024] 100, Anode 200, Cathode 300, Functional Layer 310, Hole Injection Layer

[0025] 321. First hole transport layer; 322. Second hole transport layer; 330. Organic light-emitting layer; 340. Electron transport layer

[0026] 350, Electron injection layer; 400, Electronic device Detailed Implementation

[0027] 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.

[0028] In a first aspect, this application provides an organic compound having the structure shown in Formula I:

[0029]

[0030] Wherein, X is N(R3), O or S, and R3 is selected from substituted or unsubstituted phenyl, substituted or unsubstituted phenylene;

[0031] The substituents on R3 are each independently selected from deuterium, cyano, halogen groups, alkyl groups with 1-5 carbon atoms, deuterated alkyl groups with 1-5 carbon atoms, deuterated aryl groups with 6-12 carbon atoms, or aryl groups with 6-12 carbon atoms.

[0032] Ring A is selected from aromatic rings with 6-14 carbon atoms;

[0033] L1, L2, and L3 may be the same or different, and each is independently selected from single bonds, substituted or unsubstituted aryl groups with 6-30 carbon atoms, and substituted or unsubstituted heteroaryl groups with 3-30 carbon atoms.

[0034] Ar is selected from substituted or unsubstituted aryl groups with 6-30 carbon atoms and substituted or unsubstituted heteroaryl groups with 3-30 carbon atoms;

[0035] R1 and R2 may be the same or different, and each is independently selected from deuterium, halogen group, cyano, alkyl with 1-10 carbon atoms, cycloalkyl with 3-10 carbon atoms, haloalkyl with 1-10 carbon atoms, aryl with 6-20 carbon atoms, or heteroaryl with 3-20 carbon atoms.

[0036] n1 is the number of R1s, and n1 is selected from 0, 1, 2, 3 or 4; when n1 is greater than 1, any two R1s are the same or different.

[0037] n2 is the number of R2, and n2 is selected from 0, 1, 2, 3 or 4; when n2 is greater than 1, any two R2 are the same or different;

[0038] The substituents in L1, L2, L3, and Ar may be the same or different, and each is independently selected from deuterium, cyano, halogen group, alkyl with 1-10 carbon atoms, haloalkyl with 1-10 carbon atoms, deuterated alkyl with 1-10 carbon atoms, trialkylsilyl with 3-12 carbon atoms, deuterated aryl with 6-12 carbon atoms, aryl with 6-20 carbon atoms, or heteroaryl with 3-20 carbon atoms; optionally, any two adjacent substituents in Ar can form a saturated or unsaturated 3-15 membered ring.

[0039] In this application, the terms "optionally" or "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 3-15 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.

[0040] 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.

[0041] 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 aryl group without a substituent. The aforementioned substituent, i.e., Rc, can be, for example, deuterium, a halogen group, a cyano group, a heteroaryl group, an aryl group, a trialkylsilyl group, an alkyl group, a haloalkyl group, a cycloalkyl group, etc. The number of substituents can be one or more.

[0042] In this application, "multiple" means two or more, such as two, three, four, five, six, etc.

[0043] In this application, the number of carbon atoms in substituted or unsubstituted functional groups refers to the total number of carbon atoms.

[0044] The hydrogen atoms in the compound structure of this application include various isotopes of hydrogen, such as hydrogen (H), deuterium (D), or tritium (T).

[0045] In the structural formula of the compound in this application, "D" indicates deuteration.

[0046] 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 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.

[0047] In this application, "aryl" refers to a divalent group formed by the further loss of one or more hydrogen atoms from an aryl group.

[0048] In this application, terphenyl includes

[0049] In this application, the substituted or unsubstituted aryl (arylene) group can have 6, 8, 10, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, or 30 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, the substituted or unsubstituted aryl group is a substituted or unsubstituted aryl group with 6 to 20 carbon atoms.

[0050] 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.

[0051] In this application, aryl groups used as substituents for R3, L1, L2, L3 and Ar include, but are not limited to, phenyl, naphthyl, phenanthryl, biphenyl pentadeuterated phenyl, etc.

[0052] 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 connected by carbon-carbon bonds in a conjugated manner, 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.

[0053] 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.

[0054] In this application, the number of carbon atoms in the substituted or unsubstituted heteroaryl (hybrid aryl) can be selected from 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, and 30.

[0055] In some embodiments, the substituted or unsubstituted heteroaryl group is a substituted or unsubstituted heteroaryl group with a total carbon number of 5-25.

[0056] In this application, the heteroaryl groups that serve as substituents for R3, L1, L2, L3, and Ar are, for example, but not limited to, pyridyl, carbazolyl, dibenzothiophene, dibenzofuranyl, benzoxazolyl, benzothiazolyl, and benzimidazolyl.

[0057] 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 atom, halogen group, -CN, aryl, heteroaryl, trialkylsilyl, alkyl, cycloalkyl, haloalkyl, etc.

[0058] In this application, alkyl groups having 1-10 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.

[0059] In this application, the halogen group may be, for example, fluorine, chlorine, bromine, or iodine.

[0060] In this application, specific examples of trialkylsilyl groups include, but are not limited to, trimethylsilyl, triethylsilyl, etc.

[0061] In this application, specific examples of alkyl halogens include, but are not limited to, trifluoromethyl.

[0062] In this application, the number of carbon atoms in a deuterated alkyl group that has 1 to 10 carbon atoms 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.

[0063] 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.

[0064] In this application, a ring system formed by n atoms is called an n-membered ring. For example, phenyl is a 6-membered ring. A 3-15 membered ring refers to a cyclic group having 3-15 ring atoms. Examples of 3-15 membered rings include cyclopentane, cyclohexane, fluorene rings, and benzene rings.

[0065] In this application, It refers to the chemical bond that connects with other groups.

[0066] 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 be connected to any position in the ring system that the linker penetrates, and the other end is connected 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 penetrate the bicyclic ring. This means that any possible connection mode shown in equations (f-1) to (f-10) is included.

[0067]

[0068] 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.

[0069]

[0070] Specifically, in Form I of this application L1 With the groups inside square brackets The connection methods include any possible connection methods shown in equations (Z-1) to (Z-7).

[0071]

[0072] In formula (Z-7), X is N(R3), and R3 is a substituted or unsubstituted phenylene.

[0073] 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).

[0074]

[0075] In some embodiments of this application, ring A is selected from benzene ring or naphthalene ring.

[0076] In some embodiments of this application, the organic compound is selected from the structures shown in formulas I-1 to I-16:

[0077]

[0078]

[0079] The definitions of X, L1, L2, L3, Ar, R1, R2, n1, and n2 are the same as in Equation I.

[0080] In some embodiments, R1 and R2 may be the same or different, and each is independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl or tert-butyl.

[0081] In some implementations, both n1 and n2 are 0.

[0082] In some embodiments, the substituent in R3 is selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, phenyl, pentadeuterated phenyl, or naphthyl.

[0083] In some embodiments, L1, L2, and L3 may be the same or different, and each is independently selected from single bonds, substituted or unsubstituted aryl groups with 6-18 carbon atoms, and substituted or unsubstituted heteroaryl groups with 5-15 carbon atoms. For example, L1, L2, and L3 are each independently selected from single bonds, substituted or unsubstituted aryl groups with 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, or 18 carbon atoms, and substituted or unsubstituted heteroaryl groups with 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, or 15 carbon atoms. The substituents in L1, L2, and L3 are each independently selected from deuterium, fluorine, cyano, alkyl with 1 to 5 carbon atoms, fluoroalkyl with 1 to 4 carbon atoms, deuterated alkyl with 1 to 4 carbon atoms, trialkylsilyl with 3 to 8 carbon atoms, phenyl, pentadeuterated phenyl, naphthyl, biphenyl, or pyridyl.

[0084] In some embodiments, L1, L2, and L3 may be the same or different, and each is independently selected from single-bonded, substituted, or unsubstituted groups Q, wherein the unsubstituted group Q is selected from the group consisting of:

[0085]

[0086]

[0087] The substituted group Q has one or more substituents, each substituent being independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, trideuterated methyl, trimethylsilyl, phenyl, pentadeuterated phenyl, naphthyl, biphenyl or pyridyl.

[0088] In some embodiments, L1 is selected from the group consisting of single bonds or the following groups:

[0089]

[0090] In some embodiments, L2 is selected from the group consisting of single bonds or the following groups:

[0091]

[0092] In some embodiments, L1 and L2 are each independently selected from the group consisting of single bonds or the group consisting of:

[0093]

[0094] In some embodiments, L3 is selected from the group consisting of single bonds or the following groups:

[0095]

[0096]

[0097] — # indicates the key connected to L2, This indicates a key connected to Ar.

[0098] In some embodiments, L3 is selected from the group consisting of single bonds or the following groups:

[0099]

[0100] — # indicates the key connected to L2, This indicates a key connected to Ar.

[0101] In some embodiments, Ar is selected from substituted or unsubstituted aryl groups having 6-20 carbon atoms and substituted or unsubstituted heteroaryl groups having 4-18 carbon atoms. For example, Ar is 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 4, 5, 6, 7, 8, 9, 10, 12, 13, 14, 15, 16, 17 or 18 carbon atoms.

[0102] Optionally, the substituents in Ar are selected from deuterium, cyano, fluorine, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, trideuterated methyl, trimethylsilyl, pentadeuterated phenyl, aryl with 6-12 carbon atoms, or heteroaryl with 5-12 carbon atoms.

[0103] In some embodiments, Ar is selected from substituted or unsubstituted groups W, wherein the unsubstituted group W is selected from the group consisting of:

[0104]

[0105] The substituted group W has one or more substituents, each substituent independently selected from deuterium, cyano, fluorine, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, trideuterated methyl, trimethylsilyl, pentadeuterated phenyl, phenyl, biphenyl, naphthyl, pyridyl, dibenzofuranyl, dibenzothiopheneyl, or carbazoleyl, and when the number of substituents in group W is greater than 1, the substituents may be the same or different. In some embodiments, Ar is selected from the group consisting of:

[0106]

[0107] In some embodiments, Ar is selected from the group consisting of:

[0108]

[0109] In some implementations... Selected from the group consisting of single bonds or the following groups:

[0110] In some implementations... Selected from the group consisting of the following groups:

[0111]

[0112]

[0113] Specifically, the organic compound may be selected from the group consisting of the following compounds:

[0114]

[0115]

[0116]

[0117]

[0118]

[0119]

[0120]

[0121]

[0122] 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.

[0123] According to one embodiment, the structure of the organic electroluminescent device is as follows: Figure 1 As shown, it includes an anode 100 and a cathode 200 disposed opposite to each other, and a functional layer 300 disposed between the anode 100 and the cathode 200; the functional layer 300 contains the organic compound provided in this application.

[0124] Optionally, the functional layer 300 includes an organic light-emitting layer 330, wherein the organic light-emitting layer 330 contains the organic compound provided in this application.

[0125] The light-emitting layer can be composed of the organic compounds provided in this application, or it can be composed of the organic compounds provided in this application and other materials. The light-emitting layer can be one or more layers.

[0126] In one specific embodiment of this application, an organic electroluminescent device may include an anode 100, a first hole transport layer 321, a second hole transport layer 322, an organic light-emitting layer 330 as an energy conversion layer, an electron transport layer 350, and a cathode 200, which are sequentially stacked. The organic compounds provided in this application can be applied to the organic light-emitting layer 330 of the organic electroluminescent device, effectively improving the luminous efficiency of the organic electroluminescent device and reducing the driving voltage of the organic electroluminescent device.

[0127] In this application, anode 100 includes an anode material, optionally 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. Optionally, a transparent electrode comprising indium tin oxide (ITO) as the anode is included.

[0128] Optionally, the first hole transport layer 321 and the second hole transport layer 322 each comprise one or more hole transport materials. The hole transport materials can be selected from carbazole polymers, carbazole-linked triarylamine compounds, or other types of compounds; this application does not impose any special limitations on this. The first hole transport layer 321 can be composed of compound HT-1. The second hole transport layer 322 can be composed of compound HT-2.

[0129] Optionally, a hole injection layer 310 is further disposed between the anode 100 and the hole transport layer 321 to enhance the ability to inject holes into the hole transport layer 321. The hole injection layer 310 may be selected from benzidine derivatives, starburst-like arylamine compounds, phthalocyanine derivatives, or other materials; this application does not impose any special limitations on this. The material of the hole injection layer 310 may be selected from, for example, the following compounds or any combination thereof;

[0130]

[0131] In one embodiment of this application, the hole injection layer 310 is composed of NDP-9 and HT-1.

[0132] Optionally, the organic light-emitting layer 330 may be composed of a single light-emitting material, or it may include a host material and a guest material. Optionally, the organic light-emitting layer 330 is composed of a host material and a guest material. 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.

[0133] Optionally, the host material of the organic light-emitting layer 330 includes the organic compounds provided in this application. The host material of the organic light-emitting layer 330 can be one compound, or a combination of two or more compounds.

[0134] 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 restrictions on this. The guest material is also called a dopant or dopant.

[0135] In some specific embodiments of this application, the guest material of the organic light-emitting layer 330 is GHP1 or GHN1.

[0136] The electron transport layer 340 can be a single-layer structure or a multi-layer structure, and may include one or more electron transport materials. The electron transport materials may be selected from, but are not limited to, LiQ, benzimidazole derivatives, oxadiazole derivatives, quinoxaline derivatives, or other electron transport materials; this application does not impose any special limitations on this. The material of the electron transport layer 340 includes, but is not limited to, the following compounds:

[0137]

[0138] In one embodiment of this application, the electron transport layer 340 is composed of ET-01 and LiQ.

[0139] In this application, 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 is included as the cathode.

[0140] 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 lanthanides, 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 metallic Yb.

[0141] A third aspect of this application provides an electronic device including the organic electroluminescent device described in the second aspect of this application.

[0142] 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.

[0143] The following examples illustrate the synthesis method of the organic compounds of this application, but this application is not limited thereto.

[0144] Synthesis Examples

[0145] Those skilled in the art will recognize that the chemical reactions described herein can be suitably used to prepare many of the organic 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.

[0146] 1. Synthesis of intermediates

[0147] (1) Synthesis of intermediates Sub-a-1 to Sub-g-1:

[0148]

[0149] Reactants A (80.0 g, 220.7 mmol), reactant B (80.48 g, 485.6 mmol), tetraphenylphosphine palladium (2.55 g, 2.2 mmol), potassium carbonate (91.52 g, 662.2 mmol), and tetrabutylammonium bromide (7.2 g, 22.1 mmol) were added to a flask, along with a mixed solvent of toluene (640 mL), ethanol (160 mL), and water (160 mL). Under nitrogen protection, the mixture was heated to 80 °C and stirred for 18 hours. After cooling to room temperature, stirring was stopped, and the reaction mixture was washed with water to separate the organic phase. The organic phase was dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure 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 intermediate a-1 (40.0 g, yield 65%). Mass spectrometry: m / z = 279.0 (M+H). + .

[0150] Using reactant 1 in Table 1 to replace reactant A, and reactant 2 to replace reactant B, synthesize the following intermediates using a similar method:

[0151] Table 1

[0152]

[0153] (2) Synthesis of intermediates Sub-A to Sub-Z:

[0154]

[0155] Indodo[2,3-A]carbazole (50.0 g, 195.1 mmol), sodium hydroxide (5.62 g, 234.1 mmol), and N,N-dimethylformamide (400 mL) were added to a flask and stirred until dissolved under nitrogen protection at 20 °C. Then, a solution of intermediate Sub-c-1 (54.37 g, 195.1 mmol) in N,N-dimethylformamide (100 mL) was added dropwise. After the addition was complete, the solution became clear. After 0.5 h, the solution turned yellow and a large amount of white solid was produced. After 2.5 h, a sample was taken and the conversion rate was 83.3%, indicating that the starting material had reacted completely. 500 mL of water was added to the reaction solution for washing, and the solid was filtered out. The solid was washed with 200 mL of ethanol and dried to obtain the crude product. The crude product was purified by silica gel column chromatography using a dichloromethane / n-heptane system to obtain a white solid intermediate Sub-A (60.30 g, yield 62.0%).

[0156] Using reactant 3 from Table 2 to replace indolo[2,3-A]carbazole and reactant 4 to replace intermediate Sub-c-1, the intermediates shown in Table 2 were synthesized using the method for synthesizing intermediate Sub-A:

[0157] Table 2

[0158]

[0159]

[0160]

[0161] 2. Synthesis of compounds: Taking compound 1 as an example

[0162]

[0163] Intermediate Sub-A (7.0 g, 14.0 mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine (3.76 g, 14.0 mmol), 4-dimethylaminopyridine (0.86 g, 7.0 mmol), cesium carbonate (11.4 g, 35.0 mmol), and dimethyl sulfoxide (70 mL) were added to a round-bottom flask. Under nitrogen protection, the mixture was stirred and heated to 100 °C, and reacted for 10 hours. After the reaction was completed, the mixture was cooled to room temperature, filtered, and the filter cake was washed with water and ethanol and dried to obtain the crude product. The crude product was purified by recrystallization from toluene to give a yellow solid compound 1 (5.43 g, yield 53%), mass spectrometry: m / z = 730.2 (M+H). + .

[0164] Using reactant 5 from Table 3 to replace intermediate Sub-A, and reactant 6 to replace 2-chloro-4,6-diphenyl-1,3,5-triazine, the compounds shown in the table below were synthesized using a similar method:

[0165] Table 3

[0166]

[0167]

[0168]

[0169]

[0170]

[0171]

[0172] The NMR data of some compounds are shown in Table 4:

[0173] Table 4

[0174]

[0175] Example 1

[0176] The anode is prepared through the following process: ITO / Ag / ITO with a thickness of [missing information] is [missing information]. The ITO substrate is cut into dimensions of 40mm (length) × 40mm (width) × 0.7mm (thickness). It is then prepared into an experimental substrate with cathode, anode and insulating layer patterns using a photolithography process. The surface can be treated with ultraviolet ozone and O2:N2 plasma to increase the work function of the anode. The surface of the ITO substrate can be cleaned with organic solvents to remove impurities and oil stains.

[0177] Compounds HT-1 and NDP-9 were co-deposited on the experimental substrate (anode) at a thickness ratio of 97%:3% to form a layer with a thickness of [missing information]. A hole injection layer (HIL) is formed, and then HT-1 is vacuum-deposited on the hole injection layer to form a thickness of [thickness missing]. The first hole transport layer.

[0178] HT-2 was vacuum-deposited onto the first hole transport layer to form a layer with a thickness of [missing information]. The second hole transport layer.

[0179] On the second hole transport layer, compounds GH-P1 and 1:Ir(ppy)3 were co-deposited in a thickness ratio of 47%:47%:6% to form a layer with a thickness of [missing information]. The green light-emitting layer (EML).

[0180] ET-1 and LiQ were co-deposited at a thickness ratio of 1:1 to form Thick electron transport layer (ETL).

[0181] On the electron transport layer, metallic Yb is vacuum-deposited to form 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 on the electron-injected layer at a thickness ratio of 1:9 to form a layer with a thickness of [missing information]. The cathode.

[0182] Furthermore, the thickness of the evaporation deposit on the aforementioned cathode is... The CP-1 is used to form an organic capping layer (CPL), thereby completing the fabrication of the organic light-emitting device, with a structure as follows: Figure 1 As shown.

[0183] Examples 2-40

[0184] Except that the light-emitting layer material shown in Table 6 below is used instead of the light-emitting layer in Example 1 when forming the light-emitting layer, the organic electroluminescent device is fabricated using the same method as in Example 1.

[0185] Comparative Examples 1-4

[0186] Except that the light-emitting layer material shown in the table below is used instead of the light-emitting layer material in Example 1 when forming the light-emitting layer, the organic electroluminescent device is fabricated using the same method as in Example 1.

[0187] The structures of the materials used in the comparative and example studies for fabricating organic electroluminescent devices are shown in Table 5 below:

[0188] Table 5

[0189]

[0190]

[0191] The performance of the green organic electroluminescent devices prepared in Examples 1-26 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. 95 Device lifetime is 30 mA / cm 2 The test was conducted under the specified conditions, and the test results are shown in Table 6 below:

[0192] Table 6

[0193]

[0194]

[0195] Referring to the table above, in Examples 1-40, the compound of this application was used as the host material for the green light-emitting layer. Compared with Comparative Examples 1-4, in device T... 95 With similar lifespans, both operating voltage and luminous efficiency were improved. Specifically, compared to the devices in Comparative Examples 1-2, the devices in Examples 1-32 had an operating voltage at least 0.24V lower, while the luminous efficiency was significantly improved by at least 16.8%. Meanwhile, compared to the devices in Comparative Examples 3-4, the devices in Examples 33-40 had an operating voltage at least 0.18V lower, while the luminous efficiency was significantly improved by at least 14.4%.

[0196] Therefore, when the organic compounds of this application are used to prepare green organic electroluminescent devices, they can effectively improve the luminous efficiency of the devices and improve the operating voltage to a certain extent.

[0197] The preferred embodiments of the present invention have been described in detail above. 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. An organic compound having the structure shown in Formula I: in, X is N(R3), O or S, where R3 is selected from substituted or unsubstituted phenyl groups or substituted or unsubstituted phenylene groups. The substituent in R3 is selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, phenyl, pentadeuterated phenyl, or naphthyl; ring A is selected from an aromatic ring with 6-14 carbon atoms; L1 is selected from the group consisting of single bonds or the following groups: Selected from the group consisting of the following groups: R1 and R2 may be the same or different, and each is independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl or tert-butyl; n1 is the number of R1s, which can be selected from 0, 1, 2, 3 or 4; when n1 is greater than 1, any two R1s are the same or different; n2 is the number of R2s, which can be selected from 0, 1, 2, 3 or 4; when n2 is greater than 1, any two R2s are the same or different.

2. The organic compound according to claim 1, wherein, Ring A is selected from benzene ring or naphthalene ring.

3. The organic compound according to claim 1, wherein, The compound is selected from the group consisting of the following compounds:

4. An organic electroluminescent device, comprising an anode and a cathode disposed opposite to each other, and a functional layer disposed between the anode and the cathode; the functional layer comprising an organic compound as described in any one of claims 1-3.

5. The organic electroluminescent device according to claim 4, wherein, The functional layer includes an organic light-emitting layer, which contains an organic compound as described in any one of claims 1-3.

6. An electronic device comprising the organic electroluminescent device of claim 4 or 5.

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