Organic compounds, organic electroluminescent devices, and electronic devices

Abstract

The present application relates to an organic compound, an organic electroluminescence device, and an electronic device. The organic compound of the present application has a structure as shown in formula 1, and the application of the organic compound to an organic electroluminescence device can significantly improve the performance of the device.

Description

Technical Field

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

[0002] With the development of electronic technology and the advancement of materials science, the application range of electronic components used to achieve electroluminescence or photoelectric conversion is becoming increasingly wide. Organic light-emitting diodes (OLEDs) typically include a cathode and an anode positioned opposite each other, and a functional layer disposed between the cathode and anode. This functional layer consists of multiple organic or inorganic film layers and generally includes an organic light-emitting layer, a hole transport layer, and an electron transport layer. When a voltage is applied to the cathode and anode, an electric field is generated between the two electrodes. Under the influence of the electric field, electrons on the cathode side move towards the electroluminescent layer, and holes on the anode side also move towards the light-emitting layer. Electrons and holes combine in the electroluminescent layer to form excitons. The excitons are in an excited state and release energy outward, thereby causing the electroluminescent layer to emit light. According to the statistical theorem of electron spin, singlet and triplet excitons are generated in a ratio of 1:3. The limit of the internal quantum efficiency of fluorescent organic light-emitting diodes utilizing singlet excitons is 25%. On the other hand, it is known that phosphorescent organic light-emitting devices that utilize the emission of triplet excitons can achieve an internal quantum efficiency of up to 100% when intersystem crossing is efficiently performed from singlet excitons.

[0003] Nevertheless, many problems still exist in the field of organic electroluminescent materials, particularly phosphorescent materials. For example, they suffer from short lifespan and low efficiency. Therefore, it is necessary to develop new materials to improve the performance of electronic components.

[0004] The information disclosed in the background section is only for enhancing the understanding of the background of this application, and therefore may include information that does not constitute prior art known to those skilled in the art. Summary of the Invention

[0005] To address the aforementioned problems, this application aims to provide an organic compound and an organic electroluminescent device and electronic device comprising the organic compound, wherein the organic compound can improve the performance of the organic electroluminescent device and electronic device, such as reducing the driving voltage of the device and improving the device efficiency and lifespan.

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

[0007]

[0008] Where X is selected from C(R4R5), O, S or N(Ar);

[0009] R1 is selected from substituted or unsubstituted aryl groups or groups represented by Formula 2 with 6 to 30 carbon atoms;

[0010] Ar is an aryl group consisting of 6 to 30 carbon atoms substituted by 1, 2, 3, 4 or 5 R6 atoms;

[0011] Each R6 may be the same or different, and is independently selected from hydrogen, deuterium, cyano, halogen group, alkyl with 1 to 10 carbon atoms, aryl with 6 to 30 carbon atoms, or the group shown in Formula 2;

[0012] R2 and R3 may be the same or different, and are independently selected from hydrogen, deuterium, cyano, halogen group, substituted or unsubstituted aryl group with 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl group with 3 to 30 carbon atoms, or the group shown in Formula 2.

[0013] Furthermore, one or two of R1, R6, R2, and R3 are selected from the groups shown in Formula 2;

[0014] R4 and R5 may be the same or different, and are independently selected from alkyl groups having 1 to 10 carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, and substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms.

[0015] L, L1, and L2 may be the same or different, and are 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.

[0016] Ar1 and Ar2 may be the same or different, and are independently selected from substituted or unsubstituted aryl groups with 6 to 30 carbon atoms, and substituted or unsubstituted heteroaryl groups with 3 to 30 carbon atoms, respectively.

[0017] The substituents in R1, R2, R3, R4, R5, L, L1, L2, Ar1, and Ar2 may be the same or different, and are independently selected from deuterium, halogen groups, cyano groups, alkyl groups with 1 to 10 carbon atoms, cycloalkyl groups with 3 to 20 carbon atoms, heteroaryl groups with 3 to 20 carbon atoms, deuterated aryl groups with 6 to 20 carbon atoms, haloaryl groups with 6 to 20 carbon atoms, trialkylsilyl groups with 3 to 12 carbon atoms, triarylsilyl groups with 18 to 24 carbon atoms, haloalkyl groups with 1 to 10 carbon atoms, and deuterated alkyl groups with 1 to 10 carbon atoms.

[0018] Optionally, any two adjacent substituents in Ar1 and Ar2 can form a ring.

[0019] 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.

[0020] According to a third aspect of this application, an electronic device is provided, including the organic electroluminescent device described in the second aspect.

[0021] The core group of the organic compound in this application is formed by the fusion of a dibenzo-5-membered ring and benzoxazole in a specific manner. This core group has a planar, ring-like structure, which can maintain a high first triplet energy level while possessing strong carrier transport capability and high energy transfer capability; at the same time, this group has good electron dispersion capability. Combining this core group with a triarylamine, the resulting compound can effectively improve the electron tolerance of the molecule when used as a hole transport material. When the organic compound of this application is used as the host material of the light-emitting layer in a red organic electroluminescent device, it can significantly improve the device performance.

[0022] Other features and advantages of this application will be described in detail in the following detailed description section. Attached Figure Description

[0023] 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.

[0024] Figure 1 This is a schematic diagram of the structure of an organic electroluminescent device according to this application.

[0025] Figure 2 This is a schematic diagram of the structure of an electronic device according to this application.

[0026] Figure Labels

[0027] 100, Anode 200, Cathode 300, Functional Layer 310, Hole Injection Layer

[0028] 320, Hole transport layer 320, First hole transport layer 330, Second hole transport layer 340, Organic light-emitting layer

[0029] 350, Electron transport layer; 360, Electron injection layer; 400, Electronic device. Detailed Implementation

[0030] In view of the above-mentioned problems existing in the prior art, the purpose of this application is to provide an organic compound and an organic electroluminescent device and electronic device containing the organic compound. The organic compound can improve the performance of the organic electroluminescent device and electronic device, such as reducing the driving voltage of the device and improving the device efficiency and lifespan.

[0031] According to a first aspect of this application, an organic compound is provided having a structure as shown in Formula 1:

[0032]

[0033] Where X is selected from C(R4R5), O, S or N(Ar);

[0034] R1 is selected from substituted or unsubstituted aryl groups or groups represented by Formula 2 with 6 to 30 carbon atoms;

[0035] Ar is an aryl group consisting of 6 to 30 carbon atoms substituted by 1, 2, 3, 4 or 5 R6 atoms;

[0036] Each R6 may be the same or different, and is independently selected from hydrogen, deuterium, cyano, halogen group, alkyl with 1 to 10 carbon atoms, aryl with 6 to 30 carbon atoms, or the group shown in Formula 2;

[0037] R2 and R3 may be the same or different, and are independently selected from hydrogen, deuterium, cyano, halogen group, substituted or unsubstituted aryl group with 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl group with 3 to 30 carbon atoms, or the group shown in Formula 2.

[0038] Furthermore, one or two of R1, R6, R2, and R3 are selected from the groups shown in Formula 2;

[0039] R4 and R5 may be the same or different, and are independently selected from alkyl groups having 1 to 10 carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, and substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms.

[0040] L, L1, and L2 may be the same or different, and are 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.

[0041] Ar1 and Ar2 may be the same or different, and are independently selected from substituted or unsubstituted aryl groups with 6 to 30 carbon atoms, and substituted or unsubstituted heteroaryl groups with 3 to 30 carbon atoms, respectively.

[0042] The substituents in R1, R2, R3, R4, R5, L, L1, L2, Ar1, and Ar2 may be the same or different, and are independently selected from deuterium, halogen groups, cyano groups, alkyl groups with 1 to 10 carbon atoms, cycloalkyl groups with 3 to 20 carbon atoms, heteroaryl groups with 3 to 20 carbon atoms, deuterated aryl groups with 6 to 20 carbon atoms, haloaryl groups with 6 to 20 carbon atoms, trialkylsilyl groups with 3 to 12 carbon atoms, triarylsilyl groups with 18 to 24 carbon atoms, haloalkyl groups with 1 to 10 carbon atoms, and deuterated alkyl groups with 1 to 10 carbon atoms.

[0043] Optionally, any two adjacent substituents in Ar1 and Ar2 can form a ring.

[0044] In this application, the terms "optional" or "optionally" mean that the event or situation described below may occur but does not have to occur, and the description includes the possibility that the event or situation may or may not occur. For example, "optionally, any two adjacent substituents form a ring" means that the two substituents may form a ring but are not required to form a ring, including both scenarios where the two adjacent substituents form a ring and scenarios where the two adjacent substituents do not form a ring.

[0045] In this application, the phrase "any two adjacent substituents forming a ring" can include two substituents on the same atom, or one substituent on each of two adjacent atoms. When two substituents are on the same atom, the two substituents can form a saturated or unsaturated ring with the atom they are connected to. When one substituent is on each of two adjacent atoms, the two substituents can fuse into a ring. For example, when Ar1 contains two or more substituents, the formation of a ring by any two adjacent substituents results in a saturated or unsaturated cyclic group, such as benzene rings, naphthalene rings, phenanthrene rings, anthracene rings, fluorene rings, cyclopentane, cyclohexane, adamantane, etc.

[0046] In this application, the fluorene group can be replaced by one or two substituents. Specifically, when the fluorene group is replaced, the following substitutions can be made: etc., but not limited to this.

[0047] In this application, the descriptive phrases "each...independently is," "...each independently is," and "...each independently selected from" 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.

[0048] 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, heteroaryl, deuterated aryl, haloaryl, trialkylsilyl, triarylsilyl, haloalkyl, deuterated alkyl, etc.

[0049] 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.

[0050] 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, anthraceneyl, phenanthryl, biphenyl, terphenyl, benzo[9,10]phenanthryl, pyrene, benzofluoranthraceneyl, etc. Aryl, spirodifluorenyl, etc. In this application, the aryl group refers to a divalent or polyvalent group formed by the further loss of one or more hydrogen atoms from an aryl group.

[0051] In this application, terphenyl includes

[0052] 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 atoms, halogen groups, cyano groups, aryl groups, heteroaryl groups, alkyl groups, cycloalkyl groups, 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.

[0053] 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 at least one 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-phenylcarbazoyl and N-pyridylcarbazoyl are heteroaryl groups of the polycyclic system type connected by carbon-carbon bonds. In this application, the hypoaryl group refers to the divalent group formed by the further loss of a hydrogen atom from a heteroaryl group.

[0054] 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 atoms, halogen groups, cyano groups, aryl groups, heteroaryl groups, alkyl groups, cycloalkyl groups, etc. It should be understood that the number of carbon atoms in the substituted heteroaryl group refers to the total number of carbon atoms of the heteroaryl group and the substituents on the heteroaryl group.

[0055] In this application, the number of carbon atoms in the substituted or unsubstituted aryl group can be 6 to 25, for example, the number of carbon atoms can be 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, or 25.

[0056] In this application, specific examples of aryl groups as substituents include, but are not limited to, phenyl, biphenyl, naphthyl, fluorenyl, phenanthryl, anthracene, etc. base.

[0057] In this application, the number of carbon atoms in the substituted or unsubstituted heteroaryl group can be 12 to 20, for example, the number of carbon atoms can be 12, 13, 14, 15, 16, 17, 18, 19, or 20.

[0058] In this application, specific examples of heteroaryl groups as substituents include, but are not limited to, triazinyl, pyridinyl, pyrimidinyl, carbazolyl, dibenzofuranyl, dibenzothiopheneyl, quinolinyl, quinazolinyl, quinoxalinyl, isoquinolinyl, carbazolyl, and N-phenylcarbazolyl.

[0059] In this application, the non-positioned linker refers to a single bond extending from the ring system. 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.

[0060] 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).

[0061]

[0062] For another 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.

[0063]

[0064] In this application, alkyl groups having 1 to 10 carbon atoms can include straight-chain alkyl groups having 1 to 10 carbon atoms and branched alkyl groups having 3 to 10 carbon atoms. The number of carbon atoms in an alkyl group can be, for example, 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10. Specific examples of alkyl groups include, but are not limited to, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl, neopentyl, n-hexyl, n-octyl, 2-ethylhexyl, nonyl, decyl, and 3,7-dimethyloctyl.

[0065] In this application, the halogen group may be, for example, fluorine, chlorine, bromine, or iodine.

[0066] In this application, specific examples of triarylsilyl groups include, but are not limited to, triphenylsilyl groups.

[0067] In this application, the number of carbon atoms in cycloalkyl groups with 3 to 20 carbon atoms can be, for example, 3, 4, 5, 6, 7, 8, or 10. Specific examples of cycloalkyl groups include, but are not limited to, cyclopentyl, cyclohexyl, and adamantyl.

[0068] In this application, there is one and only one of R1, R6, R2 and R3 that is a group represented by Formula 2.

[0069] In this application, the organic compound is selected from compounds represented by formula 1-1, formula 1-2, formula 1-3, formula 1-4, formula 1-5, formula 1-6, formula 1-7, formula 1-8, formula 1-9, formula 1-10, formula 1-11, formula 1-12 or formula 1-13:

[0070]

[0071] In some embodiments of this application, L is selected from substituted or unsubstituted aryl groups with a single bond and 6 to 12 carbon atoms;

[0072] Optionally, the substituents in L may be the same or different, and are independently selected from deuterium, halogen groups, cyano groups, alkyl groups or phenyl groups having 1 to 5 carbon atoms.

[0073] In other embodiments of this application, L is selected from single bonds, phenylene, naphthylene, or biphenylene.

[0074] In some embodiments of this application, L is selected from the group consisting of single bonds or groups consisting of:

[0075]

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

[0077]

[0078] In some embodiments of this application, L is selected from the group consisting of single bonds or groups consisting of:

[0079]

[0080] Optionally, L is selected from the group consisting of single bonds or groups consisting of:

[0081]

[0082] In some embodiments of this application, L1 and L2 may be the same or different, and are independently selected from single bonds, substituted or unsubstituted aryl groups with 6 to 12 carbon atoms, and substituted or unsubstituted heteroaryl groups with 12 to 18 carbon atoms.

[0083] Optionally, the substituents in L1 and L2 may be the same or different, and are independently selected from deuterium, halogen groups, cyano groups, alkyl groups or phenyl groups having 1 to 5 carbon atoms.

[0084] In other embodiments of this application, L1 and L2 may be the same or different, and are independently selected from single bonds, substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted biphenylene, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl, and substituted or unsubstituted dibenzothiophene.

[0085] Optionally, the substituents in L1 and L2 may be the same or different, and are independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl or phenyl.

[0086] In some embodiments of this application, L1 and L2 may be the same or different, and are independently selected from single-bonded, substituted or unsubstituted groups V, wherein the unsubstituted group V is selected from the group consisting of:

[0087]

[0088] in, The substituted group V represents a chemical bond; the substituted group V contains one or more substituents selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, or phenyl; and when the substituted group V contains multiple substituents, the substituents may be the same or different.

[0089] Specifically, L1 and L2 may be the same or different, and are independently selected from the group consisting of single bonds or groups of the following:

[0090]

[0091] In some embodiments of this application, Ar1 and Ar2 may be the same or different, and are independently selected from substituted or unsubstituted aryl groups with 6 to 25 carbon atoms and substituted or unsubstituted heteroaryl groups with 12 to 20 carbon atoms.

[0092] Optionally, the substituents in Ar1 and Ar2 may be the same or different, and are independently selected from deuterium, halogen groups, cyano groups, alkyl groups with 1 to 5 carbon atoms, cycloalkyl groups with 1 to 10 carbon atoms, triphenylsilyl groups, or phenyl groups.

[0093] Optionally, in Ar1 and Ar2, any two adjacent substituents form a fluorene ring.

[0094] In other embodiments of this application, Ar1 and Ar2 may be the same or different, and are independently selected from substituted or unsubstituted terphenyl, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted phenanthyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted triphenylene, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophene, and substituted or unsubstituted spirodifluorenyl.

[0095] Optionally, the substituents in Ar1 and Ar2 may be the same or different, and are independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, cyclohexyl, adamantyl, phenyl, naphthyl or triphenylsilyl.

[0096] In some embodiments of this application, Ar1 and Ar2 may be the same or different, and are independently selected from substituted or unsubstituted groups V, wherein the unsubstituted group W is selected from the group consisting of:

[0097]

[0098] The substituted group W has one or more substituents, which are independently selected from the group consisting of deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, cyclohexyl, adamantyl, phenyl, naphthyl or triphenylsilyl, and when the number of substituents on group W is greater than 1, the substituents may be the same or different.

[0099] Alternatively, Ar1 and Ar2 may be the same or different, and each may be independently selected from the group consisting of:

[0100]

[0101]

[0102] Specifically, Ar1 and Ar2 may be the same or different, and are each independently selected from the group consisting of the following groups:

[0103]

[0104] In some embodiments of this application, Each is independently selected from the group consisting of the following groups:

[0105]

[0106] In some embodiments of this application, Selected from the group consisting of the following groups:

[0107]

[0108]

[0109]

[0110]

[0111]

[0112]

[0113] In some embodiments of this application, both R4 and R5 are methyl groups.

[0114] In some embodiments of this application, R1 is selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, or a group represented by Formula 2.

[0115] Optionally, the substituents in R1 may be the same or different, and may be independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl or phenyl.

[0116] In some embodiments of this application, Ar is a phenylene or naphthylene substituted with one, two, three, four, or five R6 groups;

[0117] Each R6 may be the same or different, and is independently selected from hydrogen, deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, phenyl, naphthyl, biphenyl or the group shown in Formula 2;

[0118] In some embodiments of this application, R2 and R3 may be the same or different, and are each independently selected from hydrogen or the group represented by Formula 2.

[0119] In some embodiments of this application, R1 is selected from the group shown in Formula 2 or the group consisting of:

[0120]

[0121] In some embodiments of this application, Ar is selected from the group consisting of:

[0122]

[0123] In some specific embodiments of this application, R1 is selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl or the group shown in Formula 2;

[0124] Ar is a phenylene or naphthylene group substituted with 1, 2, 3, 4 or 5 R6 groups;

[0125] Each R6 may be the same or different, and is independently selected from hydrogen, deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, phenyl, naphthyl, biphenyl or the group shown in Formula 2;

[0126] R2 and R3 may be the same or different, and are independently selected from hydrogen or the group shown in Formula 2;

[0127] Furthermore, there is one and only one of R1, R6, R2 and R3 that is a group represented by Formula 2.

[0128] Optionally, the substituents in R1 may be the same or different, and are independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl or phenyl.

[0129] In some embodiments of this application, R1 is selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl or the group represented by Formula 2;

[0130] The substituents in R1 may be the same or different, and are independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, or phenyl.

[0131] Ar is a phenylene or naphthylene group substituted with 1, 2, 3, 4 or 5 R6 groups.

[0132] Each R6 may be the same or different, and is independently selected from hydrogen, deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, phenyl, naphthyl, biphenyl or the group shown in Formula 2.

[0133] R2 is selected from hydrogen or the group shown in Formula 2.

[0134] R3 is selected from hydrogen or the group shown in Formula 2.

[0135] In some preferred embodiments of this application, X is O or S;

[0136] R1 is selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl or the group shown in Formula 2;

[0137] R2 and R3 may be the same or different, and are independently selected from hydrogen or the group shown in Formula 2;

[0138] The substituents in R1 may be the same or different, and are independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, or phenyl.

[0139] There is exactly one group among R1, R2 and R3 that is the group shown in Formula 2.

[0140] In some embodiments of this application, the organic material is selected from the group consisting of the following compounds:

[0141]

[0142]

[0143]

[0144]

[0145]

[0146]

[0147]

[0148]

[0149]

[0150] According to a second aspect of this application, 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 contains the organic compound of this application.

[0151] In some embodiments of this application, the organic electroluminescent device is a red organic electroluminescent device. For example... Figure 1 As shown, an organic electroluminescent device may include an anode 100, a first hole transport layer 320, a second hole transport layer 330, an organic light-emitting layer 340, an electron transport layer 350, an electron injection layer 360, and a cathode 200, which are stacked sequentially.

[0152] Optionally, the anode 100 includes an anode material that 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, indium tin oxide (ITO) is included as the transparent electrode for the anode.

[0153] Optionally, the first hole transport layer 320 and the second hole transport layer 330 include one or more hole transport materials, which may be selected from carbazole polymers, carbazole-linked triarylamine compounds, or other types of compounds. Those skilled in the art can refer to existing technologies for selection, and this application does not impose any special limitations in this regard. In some embodiments of this application, the first hole transport layer 320 is HT-20, and the second hole transport layer 330 is HT-21.

[0154]

[0155] Optionally, a hole injection layer 310 may be provided between the anode 100 and the hole transport layer 320 to enhance the ability to inject holes into the hole transport layer 320. The hole injection layer 310 may 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 may, for example, be selected from the following compounds or any combination thereof;

[0156]

[0157] In some embodiments of this application, the hole injection layer 310 is composed of F4-TCNQ and HT-20.

[0158] Optionally, the organic light-emitting layer 340 may be composed of a single light-emitting layer material, or it may include a host material and a dopant material. Optionally, the organic light-emitting layer 340 is composed of a host material and a dopant material. Holes and electrons injected into the organic light-emitting layer 340 can recombine in the organic light-emitting layer 340 to form excitons. The excitons transfer energy to the host material, and the host material transfers energy to the dopant material, thereby enabling the dopant material to emit light.

[0159] The main material of the organic light-emitting layer 340 can be a metal chelate compound, a bis(styrene) derivative, an aromatic amine derivative, a dibenzofuran derivative, or other types of materials. This application does not impose any special restrictions on this.

[0160] In one embodiment of this application, the organic light-emitting layer 340 comprises the organic material of this application.

[0161] Optionally, the organic material of this application is used as the host material (hole-type host material) of the organic light-emitting layer 340.

[0162] In some embodiments of this application, the electronic host material of the organic light-emitting layer 340 is...

[0163] The guest material of the organic light-emitting layer 340 can be a compound with a condensed aryl ring or its derivatives, a compound with a heteroaryl ring or its derivatives, an aromatic amine derivative, or other materials; this application does not impose any special limitations on this. The guest material is also referred to as a dopant or dopant. Specific examples of red phosphorescent dopants used in red organic electroluminescent devices include, but are not limited to, […].

[0164]

[0165] In a more specific embodiment, the host material of the organic light-emitting layer 340 is the organic compound of this application and RH-01, and the guest material is RD-01.

[0166] The electron transport layer 350 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, ET-01, LiQ, 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 350 include, but are not limited to, the following compounds:

[0167]

[0168] In some specific embodiments of this application, the electron transport layer 350 is composed of ET-01 and LiQ.

[0169] 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.

[0170] In some embodiments of this application, the electron injection layer 360 may include ytterbium (Yb).

[0171] A third aspect of this application provides an electronic device including the electronic components described in the second aspect of this application.

[0172] 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.

[0173] The following examples illustrate the synthesis method of the organic compounds of this application, but this application is not limited thereto.

[0174] Compounds synthesized using methods not mentioned in this application are all raw material products obtained through commercial means.

[0175] This application does not specifically limit the synthesis method of the provided organic materials. Those skilled in the art can determine a suitable synthesis method based on the organic materials and the preparation methods provided in the preparation examples section of this application. Those skilled in the art can obtain all the organic materials provided in this application based on these exemplary preparation methods. All specific preparation methods for these organic materials will not be detailed here, and should not be construed as limitations on this application.

[0176] Preparation of compounds

[0177] Synthesis of intermediate b1:

[0178]

[0179] Intermediate a1 (16.1 g; 63.4 mmol), 1,8-dibromonaphthalene (18.1 g; 63.4 mmol), tetratetraphenylphosphine palladium (1.5 g; 1.3 mmol), potassium carbonate (17.5 g; 126.7 mmol), tetrabutylammonium bromide (4.1 g; 12.7 mmol), toluene (120 mL), ethanol (30 mL), and deionized water (30 mL) were added to a round-bottom flask under nitrogen protection. The mixture was heated to 75-80 °C and stirred for 24 hours. The reaction mixture was cooled to room temperature, and deionized water (200 mL) was added. The mixture was separated, and the organic phase was washed with water and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure. The crude product was purified by silica gel column chromatography using a dichloromethane / n-heptane solvent system to obtain a pale yellow oily intermediate b1 (15.5 g; yield 73%).

[0180] Following the synthetic method for intermediate b1, reactant A was used to replace intermediate a1, and reactant B was used to replace 1,8-dibromonaphthalene to synthesize the intermediates shown in Table 1 below:

[0181] Table 1

[0182]

[0183]

[0184]

[0185] Synthesis of intermediate c1:

[0186]

[0187] Intermediate b1 (15.5 g; 46.5 mmol), palladium acetate (1.0 g; 4.6 mmol), 3-nitropyridine (0.6 g; 4.6 mmol), hexafluorobenzene (60 mL), 1,3-dimethyl-2-imidazolinone (50 mL), and tert-butyl peroxide (18.0 g; 92.9 mmol) were added to a round-bottom flask under nitrogen protection. The mixture was heated to 90-95 °C and reacted for 12 hours. The reaction was stopped and cooled to room temperature. Dichloromethane (100 mL) and deionized water (200 mL) were added to the reaction mixture. The mixture was separated, and the organic phase was washed with water and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure. The crude product was purified by silica gel column chromatography using dichloromethane / n-heptane as solvent to give a white solid intermediate c1 (8.0 g; yield 52%).

[0188] Following the method used to synthesize intermediate c1, reactant C was used to replace intermediate b1 to synthesize the intermediates shown in Table 2 below:

[0189] Table 2

[0190]

[0191]

[0192] Synthesis of intermediate C7:

[0193]

[0194] Intermediate B7 (15.0 g; 41.4 mmol), triphenylphosphine (27.1 g; 103.4 mmol), and o-dichlorobenzene (150 mL) were added to a round-bottom flask under nitrogen protection. The mixture was heated to 175-180 °C with stirring and reacted for 48 hours. The reaction mixture was cooled to room temperature, and deionized water (200 mL) was added. The mixture was separated, and the organic phase was washed with water and dried over anhydrous magnesium sulfate. The solvent was removed under high temperature and reduced pressure. The crude product was purified by silica gel column chromatography using a dichloromethane / n-heptane system to give a white solid intermediate C6 (9.2 g; yield 67%).

[0195] Following the synthetic method for intermediate c7, reactant E was used to replace intermediate b7 to synthesize the intermediates shown in Table 3 below:

[0196] Table 3

[0197]

[0198]

[0199] Synthesis of intermediate C12:

[0200]

[0201] Intermediate B12 (9.0 g; 25.7 mmol), palladium chloride (0.2 g; 1.3 mmol), and dimethyl sulfoxide (90 mL) were added to a round-bottom flask under nitrogen protection and reacted at 140-145 °C for 36 hours with stirring. After cooling to room temperature, dichloromethane (100 mL) and deionized water (150 mL) were added to the reaction mixture. The mixture was separated, the organic phase was washed with water, and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure. The crude product was purified by silica gel column chromatography using a dichloromethane / n-heptane system to give a white solid intermediate C12 (6.6 g; yield 74%).

[0202] Following the synthetic method for intermediate c12, reactant G was used to replace intermediate b12 to synthesize the intermediates shown in Table 4 below:

[0203] Table 4

[0204]

[0205] Synthesis of intermediate C16:

[0206]

[0207] Intermediate B16 (15.8 g; 41.0 mmol) and dichloroethane (140 mL) were added to a round-bottom flask under nitrogen protection. Trimethylaluminum (14.8 g; 204.9 mmol) hexane solution was slowly added dropwise under stirring at 20-25 °C. After the addition was complete, the reaction was continued at 20-25 °C for 1 hour. Hydrochloric acid (22.4 g; 614.6 mmol) aqueous solution was added to the reaction mixture, and extraction was performed using diethyl ether. The organic phases were combined, dried, and the solvent was removed under reduced pressure. The crude product was purified by silica gel chromatography using dichloromethane / n-heptane as the solvent system to obtain a white solid intermediate C16 (7.2 g; yield 49%).

[0208] Following the synthetic method for intermediate C16, reactant I was used to replace intermediate B15 to synthesize the intermediates shown in Table 5 below:

[0209] Table 5

[0210]

[0211] Synthesis of intermediate d1:

[0212]

[0213] Intermediate C1 (7.9 g; 23.8 mol), cuprous iodide (0.5 g; 2.4 mmol), 8-hydroxyquinalidine (0.8 g; 4.8 mmol), tetrabutylammonium hydroxide (18.5 g; 71.5 mmol), dimethyl sulfoxide (80 mL), and deionized water (120 mL) were added to a round-bottom flask under nitrogen protection. The mixture was heated to 125-130 °C with stirring and reacted for 24 hours. After cooling to room temperature, dichloromethane (150 mL) and deionized water (200 mL) were added to the reaction mixture. The mixture was separated, and the organic phase was washed with water and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure. The crude product was purified by silica gel column chromatography using a dichloromethane / n-heptane system to give a white solid intermediate D1 (5.1 g; yield 80%).

[0214] Following the synthetic method for intermediate d1, reactant L was used to replace intermediate c1 to synthesize the intermediates shown in Table 6 below:

[0215] Table 6

[0216]

[0217]

[0218]

[0219] Synthesis of intermediate e1:

[0220]

[0221] Intermediate d1 (5.0 g; 18.6 mmol), nickel nitrate hexahydrate (5.4 g; 18.6 mmol), p-toluenesulfonic acid (0.04 g; 0.2 mmol), and acetone (100 mL) were added to a round-bottom flask under nitrogen protection and reacted at 20-25 °C with stirring for 2 hours. The reaction was stopped, and dichloromethane (100 mL) and deionized water (150 mL) were added to the reaction mixture. The mixture was separated, the organic phase was washed with water, dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The crude product was purified by silica gel column chromatography using a dichloromethane / n-heptane system to give a white solid intermediate e1 (4.7 g; yield 81%).

[0222] Following the synthetic method for intermediate e1, reactant M was used to replace intermediate d1 to synthesize the intermediates shown in Table 7 below:

[0223] Table 7

[0224]

[0225]

[0226]

[0227] Synthesis of intermediate o1-cl:

[0228]

[0229] Intermediate e1 (4.7 g; 15.0 mmol), benzyl alcohol (1.9 g, 18.0 mmol), 1,1'-bis(diphenylphosphine)ferrocene (0.2 g; 0.4 mmol), and xylene (50 mL) were added to a round-bottom flask under nitrogen protection. The mixture was heated to 130-135 °C under stirring and refluxed for 48 h. After cooling to room temperature, toluene (50 mL) and deionized water (100 mL) were added to the reaction mixture. The organic phases were combined, and the organic layer was dried over anhydrous magnesium sulfate. The mixture was filtered and concentrated. The crude product was purified by silica gel column chromatography using a dichloromethane / n-heptane system to obtain a white solid intermediate o1-cl (3.5 g; yield 63%).

[0230] Following the synthetic method of intermediate o1-cl, reactant N was used to replace intermediate e1, and reactant P was used to replace benzyl alcohol to synthesize the intermediates shown in Table 8 below:

[0231] Table 8

[0232]

[0233]

[0234]

[0235] Synthesis of intermediate n1-cl

[0236]

[0237] Intermediate n1-h (5.5 g; 14.9 mmol), iodobenzene (3.3 g; 16.4 mmol), cuprous iodide (0.6 g; 3.0 mmol), anhydrous potassium carbonate (4.5 g; 32.8 mmol), 1,10-phenanthroline (1.1 g; 6.0 mmol), 18-crown ether-6 (0.8 g; 3.0 mmol), and dimethylformamide (50 mL) were added to a round-bottom flask under nitrogen protection, and the mixture was heated to 13°C with stirring. The reaction was carried out at 5℃-140℃ for 24 hours. The reaction was then stopped, and the reaction solution was cooled to room temperature. Deionized water (100 mL) and dichloromethane (100 mL) were added, and the mixture was separated. The organic phase was washed thoroughly with plenty of water and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure. The crude product was purified by silica gel column chromatography using a dichloromethane / n-heptane solvent system, followed by recrystallization using a dichloromethane / n-heptane mixed solvent to obtain a white solid intermediate, n1-cl (5.1 g; yield 77%).

[0238] Following the synthetic method of intermediate n1-cl, reactant Q was used to replace intermediate n1-h, and reactant R was used to replace iodobenzene to synthesize the intermediates shown in Table 9 below:

[0239] Table 9

[0240]

[0241]

[0242] Synthesis of intermediate o1-bo:

[0243]

[0244] Intermediate O1-Cl (3.5 g; 9.5 mmol), pinacol diborate (3.6 g; 14.2 mmol), tris(dibenzylacetone)palladium (0.2 g; 0.2 mmol), 2-dicyclohexylphosphine-2',4',6'-triisopropylbiphenyl (0.2 g; 0.4 mmol), potassium acetate (1.4 g; 14.2 mmol), and 1,4-dioxane (30 mL) were added to a round-bottom flask under nitrogen protection and reacted at 100-105 °C for 24 hours with stirring. After cooling to room temperature, dichloromethane (50 mL) and deionized water (50 mL) were added to the reaction solution. The mixture was separated, and the organic phase was washed with water and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure. The crude product was purified by silica gel column chromatography using dichloromethane / n-heptane as solvent to obtain a white solid intermediate O1-BO (3.1 g; yield 71%).

[0245] Following the synthetic method for intermediate o1-bo, reactant U was used to replace intermediate o1-cl to synthesize the intermediates shown in Table 10 below:

[0246] Table 10

[0247]

[0248] Synthesis of intermediate o1-ph:

[0249]

[0250] Intermediate O1-BO (3.1 g; 6.7 mmol), 1-bromo-4-chlorobenzene (1.4 g; 7.1 mmol), tetratetraphenylphosphine palladium (0.2 g; 0.1 mmol), potassium carbonate (1.9 g; 13.4 mmol), tetrabutylammonium bromide (0.4 g; 1.3 mmol), toluene (25 mL), ethanol (6 mL), and deionized water (6 mL) were added to a round-bottom flask under nitrogen protection. The mixture was heated to 75-80 °C and stirred for 48 hours. The reaction mixture was cooled to room temperature, and deionized water (50 mL) was added. The mixture was separated, and the organic phase was washed with water and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure. The crude product was purified by silica gel column chromatography using a dichloromethane / n-heptane solvent system to obtain a white solid intermediate O1-PH (2.5 g; yield 83%).

[0251] Following the same method as intermediate o1-ph, reactant V replaced intermediate o1-bo, and reactant W replaced 1-bromo-4-chlorobenzene, to synthesize the intermediates shown in Table 11 below:

[0252] Table 11

[0253]

[0254] Synthesis of compound A2:

[0255]

[0256] Intermediate o1-cl (5.0 g; 13.5 mmol), N-phenyl-2-naphthylamine (3.1 g; 14.2 mmol), tris(dibenzylideneacetone)dipalladium (0.1 g; 0.1 mmol), 2-dicyclohexylphosphine-2',4',6'-triisopropylbiphenyl (0.1 g; 0.3 mmol), sodium tert-butoxide (1.9 g; 20.3 mmol), and toluene (50 mL) were added to a round-bottom flask under nitrogen protection. The mixture was heated to 100 °C–105 °C and stirred for 16 hours. The reaction mixture was cooled to room temperature, and deionized water (100 mL) was added. The mixture was separated, and the organic phase was washed with water and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure. The crude product was purified by silica gel column chromatography using a dichloromethane / n-heptane solvent system, and then purified by recrystallization using a toluene / n-heptane solvent system to give a white solid compound A2 (5.5 g; yield 74%).

[0257] Following the same method as compound A2, reactant Y replaced intermediate o1-cl, and reactant Z replaced N-phenyl-2-naphthylamine, to synthesize the compounds shown in Table 12 below:

[0258] Table 12

[0259]

[0260]

[0261]

[0262]

[0263]

[0264] The mass spectrometry data of some compounds are shown in Table 13 below:

[0265] Table 13

[0266] Compound A2 <![CDATA[m / z=553.2(M+H) + ]]> Compound B33 <![CDATA[m / z=818.3(M+H) + ]]> Compound A7 <![CDATA[m / z=579.2(M+H) + ]]> Compound B46 <![CDATA[m / z=758.2(M+H) + ]]> Compound A14 <![CDATA[m / z=679.2(M+H) + ]]> Compound B55 <![CDATA[m / z=770.3(M+H) + ]]> Compound A20 <![CDATA[m / z=709.2(M+H) + ]]> Compound C1 <![CDATA[m / z=671.2(M+H) + ]]> Compound A39 <![CDATA[m / z=744.3(M+H) + ]]> Compound C9 <![CDATA[m / z=735.2(M+H) + ]]> Compound A46 <![CDATA[m / z=653.2(M+H) + ]]> Compound C18 <![CDATA[m / z=745.2(M+H) + ]]> Compound A52 <![CDATA[m / z=609.2(M+H) + ]]> Compound C48 <![CDATA[m / z=721.2(M+H) + ]]> Compound B8 <![CDATA[m / z=846.3(M+H) + ]]> Compound D7 <![CDATA[m / z=757.3(M+H) + ]]> Compound B14 <![CDATA[m / z=743.3(M+H) + ]]> Compound D21 <![CDATA[m / z=757.3(M+H) + ]]> Compound B21 <![CDATA[m / z=654.3(M+H) + ]]> Compound D32 <![CDATA[m / z=781.3(M+H) + ]]> Compound A61 <![CDATA[m / z=512.2(M+H) + ]]> Compound A62 <![CDATA[m / z=741.3(M+H) + ]]> Compound A63 <![CDATA[m / z=744.3(M+H) + ]]> Compound A64 <![CDATA[m / z=745.3(M+H) + ]]>

[0267] The NMR data for some compounds are shown in Table 14 below:

[0268] Table 14

[0269]

[0270] Fabrication of organic electroluminescent devices

[0271] Example 1: Fabrication of a red organic electroluminescent device

[0272] First, anodizing pretreatment is performed through the following process: [The process is repeated in the original text, so the translation is incomplete.] On the ITO / Ag / ITO substrate, surface treatment is performed using ultraviolet ozone and O2:N2 plasma to increase the work function of the anode. The surface of the ITO / Ag / ITO substrate is cleaned with organic solvents to remove impurities and oil stains.

[0273] F4-TCNQ and HT-20 were co-deposited on the experimental substrate (anode) at a deposition rate of 1%:99%, forming a layer with a thickness of [missing information]. A hole injection layer (HIL) is formed, and then HT-20 is vacuum-deposited on the hole injection layer to form a thickness of [missing information]. The first hole transport layer.

[0274] Compound HT-21 was vacuum-deposited onto the first hole transport layer to form a thickness of [missing information]. The second hole transport layer.

[0275] Next, on the second hole transport layer, RH-01:compound A2:RD-01 were co-deposited at a deposition rate of 49%:49%:2% to form a layer with a thickness of [missing information]. Organic light-emitting layer (EML).

[0276] On the organic light-emitting layer, compounds ET-01 and LiQ are mixed in a 1:1 weight ratio and deposited by vapor deposition. A thick electron transport layer (ETL) is formed by depositing Yb onto the electron transport layer to create a layer with a thickness of [thickness value missing]. An electron-injected layer (EIL) was formed, and then magnesium (Mg) and silver (Ag) were mixed at a evaporation rate of 1:9 and vacuum-deposited onto the electron-injected layer to form a layer with a thickness of [missing information]. The cathode.

[0277] Furthermore, CP-1 is vacuum-deposited onto the aforementioned cathode to form a thickness of [missing information]. An organic coating layer is applied to complete the fabrication of a red organic electroluminescent device.

[0278] Examples 2-24

[0279] Organic electroluminescent devices were prepared using the same method as in Example 1, except that the compounds listed in Table 15 below (collectively referred to as "Compound X") were used instead of Compound A2 in Example 1 when fabricating the light-emitting layer.

[0280] Comparative Examples 1-2

[0281] Except that, when fabricating the light-emitting layer, compounds I and II were used instead of compound A2 in Example 1, the organic electroluminescent device was prepared using the same method as in Example 1.

[0282] The main compound structures used in the preparation of each example and comparative example are as follows:

[0283]

[0284]

[0285] The performance of the red organic electroluminescent devices prepared in Examples 1-24 and Comparative Examples 1-2 was tested, specifically at 10 mA / cm². 2 The IVL performance of the device was tested under the specified conditions. The lifetime of the T95 device was 20 mA / cm. 2 The test was conducted under the specified conditions, and the test results are shown in Table 15.

[0286] Table 15

[0287]

[0288] As shown in Table 15 above, Examples 1-24, in which the compounds of this application were used as the hole-type host material in the red emitting layer hybrid host material, showed significant improvements in device voltage, current efficiency, and lifetime compared to Comparative Examples 1 and 2. Specifically, the current efficiency was increased by at least 15.1%, and the lifetime T95(h) was increased by at least 12.2%.

[0289] The core group of the organic compound in this application is formed by the fusion of a dibenzo-5-membered ring and benzoxazole in a specific manner. This core group has a planar, ring-like structure, which can maintain a high first triplet energy level while possessing strong carrier transport and high energy transfer capabilities; at the same time, this group has good electron dispersion ability. Combining this core group with a triarylamine, the resulting compound can effectively improve the electron tolerance of the molecule as a hole transport material. When the organic compound of this application is used as the host material of the light-emitting layer in a red organic electroluminescent device, it can significantly improve device performance. In particular, the device performance is optimal when the dibenzo-5-membered ring is dibenzofuran / dibenzothiophene.

[0290] It should be understood that this application is not limited to the precise structure described above and shown in the accompanying drawings, and various modifications and changes can be made without departing from its scope. The scope of this application is limited only by the appended claims.

Claims

1. An organic compound, characterized in that, This organic compound has the structure shown in Formula 1: Formula 1 Formula 2 Where X is selected from C(R4R5), O, S or N(Ar); R1 is selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl or the group shown in Formula 2; The substituents in R1 may be the same or different, and are independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, or phenyl. Ar is a phenylene or naphthylene group substituted with one, two, three, four, or five R6 groups; Each R6 may be the same or different, and is independently selected from hydrogen, deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, phenyl, naphthyl, biphenyl or the group shown in Formula 2; R2 and R3 may be the same or different, and are independently selected from hydrogen, deuterium or the group shown in Formula 2; Furthermore, one or two of R1, R6, R2, and R3 are selected from the groups shown in Formula 2; Both R4 and R5 are methyl groups; L is selected from single bond, phenylene, naphthylene, or biphenylene; L1 and L2 may be the same or different, and are independently selected from single bonds, substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted biphenylene, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophene. The substituents in L1 and L2 may be the same or different, and are independently selected from deuterium, halogen groups, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, or phenyl. Ar1 and Ar2 may be the same or different, and are independently selected from substituted or unsubstituted terphenyl, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted phenanthyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted triphenylene, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted spirodifluorenyl; The substituents in Ar1 and Ar2 may be the same or different, and are independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, cyclohexyl, adamantyl, phenyl, and naphthyl.

2. The organic compound according to claim 1, characterized in that, The organic compound is selected from compounds represented by formula 1-1, formula 1-2, formula 1-3, formula 1-4, formula 1-5, formula 1-6, formula 1-7, formula 1-8, formula 1-9, formula 1-10, formula 1-11, formula 1-12 or formula 1-13:

3. The organic compound according to claim 1, characterized in that, L is selected from the group consisting of single bonds or the following groups: 。 4. The organic compound according to claim 1, characterized in that, R2 and R3 may be the same or different, and are independently selected from hydrogen or the group shown in Formula 2; Furthermore, there is one and only one of R1, R6, R2 and R3 that is a group represented by Formula 2.

5. The organic compound according to claim 1, characterized in that, The organic compounds are selected from the group consisting of the following compounds:

6. An organic electroluminescent device, characterized in that, It includes an anode and a cathode arranged opposite to each other, and a functional layer disposed between the anode and the cathode; The functional layer comprises the organic compound as described in any one of claims 1 to 5.

7. The organic electroluminescent device according to claim 6, characterized in that, The functional layer includes an organic light-emitting layer; the organic light-emitting layer contains the organic compound.

8. The organic electroluminescent device according to claim 6, characterized in that, The organic electroluminescent device is a red organic electroluminescent device.

9. An electronic device, characterized in that, Includes the organic electroluminescent device according to any one of claims 6 to 8.

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