Organic compound and organic electroluminescent device and electronic device containing the same

Abstract

The present application belongs to the field of organic electroluminescence technology, and provides an organic compound and an organic electroluminescent device and an electronic device containing the same. The organic compound has a structure shown in Formula I, and an organic electroluminescent device prepared by using the compound as a hole transport layer material has good photoelectric properties.

Description

Technical Field

[0001] The invention relates to the field of organic electroluminescence, and in particular to an organic compound and an organic electroluminescent device and an electronic device containing the organic compound. Background Art

[0002] Organic electroluminescent devices (OLEDs) are devices made by depositing a layer of organic material between two metal electrodes by spin coating or vacuum evaporation. A classic three-layer organic electroluminescent device includes a hole transport layer, a light-emitting layer, and an electron transport layer. The holes generated by the anode pass through the hole transport layer and the electrons generated by the cathode pass through the electron transport layer to combine in the light-emitting layer to form excitons, which then emit light. Organic electroluminescent devices can be adjusted to emit various required lights by changing the material of the light-emitting layer as needed.

[0003] At present, products based on OLED light-emitting and display technology have been industrialized. Compared with liquid crystal display technology, OLED display technology has many advantages such as self-luminescence, no radiation, light weight, thin thickness, wide viewing angle, wide color gamut, stable color, fast response speed, strong environmental adaptability, and flexible display. Therefore, OLED display technology has received more and more attention and corresponding technical investment.

[0004] At present, many prior arts disclose that aromatic amine compounds can be used as hole transport materials or auxiliary hole transport layer materials in OLED devices to regulate the transport and injection of carriers into the organic light-emitting layer. However, it is still necessary to continue to develop new materials to further improve the performance of electronic components. Summary of the invention

[0005] The purpose of the present application is to provide an organic compound and an organic electroluminescent device and an electronic device containing the same. The organic compound is used in an organic electroluminescent device to improve the performance of the device.

[0006] According to the first aspect of the present application, an organic compound is provided, wherein the organic compound has a structure shown in Formula I:

[0007]

[0008] in,

[0009] X is selected from a single bond, C(R4R 5) , O or S;

[0010] R4 and R5 are the same or different and are each independently selected from hydrogen, an alkyl group having 1 to 10 carbon atoms, or an aryl group having 6 to 20 carbon atoms;

[0011] R1, R2 and R3 are the same or different and are independently selected from deuterium, cyano, halogen, alkyl having 1 to 10 carbon atoms, haloalkyl having 1 to 10 carbon atoms, deuterated alkyl having 1 to 10 carbon atoms, deuterated aryl having 6 to 12 carbon atoms, trialkylsilyl having 3 to 12 carbon atoms, aryl having 6 to 20 carbon atoms, heteroaryl having 3 to 20 carbon atoms or cycloalkyl having 3 to 10 carbon atoms;

[0012] m is the number of L connected in sequence, and m is selected from 0, 1 or 2;

[0013] n1 is the number of R1, and n1 is selected from 0, 1, 2, 3 or 4; when n1 is greater than 1, any two R1 are the same or different; optionally, any two adjacent R1 form a ring;

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

[0015] n3 is the number of R3, and n3 is selected from 0, 1, 2, 3 or 4; when n3 is greater than 1, any two R3 are the same or different; optionally, any two adjacent R3 form a ring;

[0016] L, L1 and L2 are the same or different and are each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, and a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms;

[0017] Ar1 and Ar2 are each independently selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms;

[0018] The substituents in L, L1, L2, Ar1 and Ar2 are the same or different and are independently selected from deuterium, cyano, halogen group, alkyl group having 1 to 10 carbon atoms, haloalkyl group having 1 to 10 carbon atoms, deuterated alkyl group having 1 to 10 carbon atoms, trialkylsilyl group having 3 to 12 carbon atoms, aryl group having 6 to 20 carbon atoms, heteroaryl group having 3 to 20 carbon atoms or cycloalkyl group having 3 to 10 carbon atoms; optionally, any two adjacent substituents in Ar1 form a saturated or unsaturated 3 to 15-membered ring; optionally, any two adjacent substituents in Ar2 form a saturated or unsaturated 3 to 15-membered ring.

[0019] According to a second aspect of the present application, an organic electroluminescent device is provided, comprising an anode and a cathode arranged opposite to each other, and a functional layer arranged between the anode and the cathode; the functional layer comprises the above-mentioned organic compound.

[0020] According to a third aspect of the present application, an electronic device is provided, comprising the organic electroluminescent device according to the second aspect.

[0021] The parent core structure of the compound of the present application is a spirobifluorene of a tetramethylcyclohexyl fused on a benzene ring, wherein the two fluorene ring planes are perpendicular to each other, and the fused polyalkyl-substituted cycloalkyl further adjusts the steric hindrance of the compound molecule, which can effectively avoid the stacking between molecules and improve the film-forming property of the compound. On the non-fused fluorene group of the parent core, an aromatic amine group is connected, and the fused cycloalkyl in the parent core is far away from the N atom in the aromatic amine, thereby reducing the effect of the electron-rich alkyl on hole injection and improving the hole injection capacity of the compound. Therefore, the compound of the present application is evaporated into an organic electroluminescent device as a hole transport layer material, which can not only improve the luminous efficiency of the device, but also improve the film-forming property of the material, thereby significantly improving the device life. BRIEF DESCRIPTION OF THE DRAWINGS

[0022] The accompanying drawings are used to provide further understanding of the present application and constitute a part of the specification. Together with the following specific embodiments, they are used to explain the present application, but do not constitute a limitation to the present application.

[0023] Figure 1 It is a schematic diagram of the structure of an organic electroluminescent device according to one embodiment of the present application.

[0024] Figure 2 It is a schematic diagram of the structure of an electronic device according to an embodiment of the present application.

[0025] Reference numerals

[0026] 100, anode 200, cathode 300, functional layer 310, hole injection layer

[0027] 321, hole transport layer 322, hole auxiliary layer 330, organic light emitting layer 340, electron transport layer

[0028] 350. Electron injection layer 400. Electronic device DETAILED DESCRIPTION

[0029] Exemplary embodiments will now be described more fully with reference to the accompanying drawings. However, exemplary embodiments can be implemented in a variety of forms and should not be construed as limited to the examples set forth herein; rather, these embodiments are provided so that the present application will be more comprehensive and complete and the concepts of the exemplary embodiments are fully conveyed 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, many specific details are provided to provide a full understanding of the embodiments of the present application.

[0030] In a first aspect, the present application provides an organic compound having a structure shown in Formula I:

[0031]

[0032] in,

[0033] X is selected from a single bond, CR4R5, O or S;

[0034] R4 and R5 are the same or different and are each independently selected from hydrogen, an alkyl group having 1 to 10 carbon atoms, or an aryl group having 6 to 20 carbon atoms;

[0035] R1, R2 and R3 are the same or different and are independently selected from deuterium, cyano, halogen, alkyl having 1 to 10 carbon atoms, haloalkyl having 1 to 10 carbon atoms, deuterated alkyl having 1 to 10 carbon atoms, deuterated aryl having 6 to 12 carbon atoms, trialkylsilyl having 3 to 12 carbon atoms, aryl having 6 to 20 carbon atoms, heteroaryl having 3 to 20 carbon atoms or cycloalkyl having 3 to 10 carbon atoms;

[0036] m is the number of L connected in sequence, and m is selected from 0, 1 or 2;

[0037] n1 is the number of R1, and n1 is selected from 0, 1, 2, 3 or 4; when n1 is greater than 1, any two R1 are the same or different; optionally, any two adjacent R1 form a ring;

[0038] n2 is the number of R2, n2 is selected from 0, 1, 2, 3 or 4; when n2 is greater than 1, any two R2 are the same or different; optionally, any two adjacent R2 form a ring;

[0039] n3 is the number of R3, n3 is selected from 0, 1, 2, 3 or 4; when n3 is greater than 1, any two R3 are the same or different; optionally, any two adjacent R3 form a ring; L, L1 and L2 are the same or different, and are each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, and a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms;

[0040] Ar1 and Ar2 are each independently selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms;

[0041] The substituents in L, L1, L2, Ar1 and Ar2 are the same or different and are independently selected from deuterium, cyano, halogen group, alkyl group having 1 to 10 carbon atoms, haloalkyl group having 1 to 10 carbon atoms, deuterated alkyl group having 1 to 10 carbon atoms, trialkylsilyl group having 3 to 12 carbon atoms, aryl group having 6 to 20 carbon atoms, heteroaryl group having 3 to 20 carbon atoms or cycloalkyl group having 3 to 10 carbon atoms; optionally, any two adjacent substituents in Ar1 form a saturated or unsaturated 3 to 15-membered ring; optionally, any two adjacent substituents in Ar2 form a saturated or unsaturated 3 to 15-membered ring.

[0042] In the present application, the terms "optionally" and "optionally" mean that the event or environment described subsequently 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 and do not form a ring. "Any two adjacent" can include two substituents on the same atom, and can also include two adjacent atoms each having one substituent; wherein, when there are two substituents on the same atom, the two substituents can form a saturated or unsaturated spiro ring with the atom to which they are commonly connected; when there is one substituent on two adjacent atoms respectively, the two substituents can be fused into a ring.

[0043] In this application, the descriptions "each... independently is" and "... are independently" and "... are independently" are interchangeable and should be understood in a broad sense. They can mean that in different groups, the specific options expressed by the same symbols do not affect each other, or in the same group, the specific options expressed by the same symbols do not affect each other. For example, Wherein, each q is independently 0, 1, 2 or 3, and each R" is independently selected from hydrogen, deuterium, fluorine, and chlorine, which means: Formula Q-1 indicates that there are q substituents R" on the benzene ring, and 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, and the number q of R" substituents on the two benzene rings can be the same or different, and each R" can be the same or different, and the options of each R" do not affect each other.

[0044] In the present application, the term "substituted or unsubstituted" means that the functional group recorded after the term may or may not have a substituent (hereinafter, for the convenience of description, the substituents are collectively referred to as Rc). For example, "substituted or unsubstituted aryl" refers to an aryl with a substituent Rc or an aryl without a substituent. The above-mentioned 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 1 or more.

[0045] In the present application, "plurality" means more than 2, for example, 2, 3, 4, 5, 6, etc.

[0046] In the present application, the number of carbon atoms in a substituted or unsubstituted functional group refers to the number of all carbon atoms.

[0047] The hydrogen atoms in the structures of the compounds of the present application include various isotope atoms of the hydrogen element, such as hydrogen (H), deuterium (D) or tritium (T).

[0048] The "D" in the structural formula of the compound of the present application represents deuteration.

[0049] In the present application, "aryl" refers to an optional functional group or substituent derived from an aromatic carbocyclic ring. The aryl group can be a monocyclic aryl group (e.g., phenyl) or a polycyclic aryl group. In other words, the aryl group can be a monocyclic aryl group, a condensed ring aryl group, two or more monocyclic aryl groups connected by conjugation of carbon-carbon bonds, monocyclic aryl groups and condensed ring aryl groups connected by conjugation of carbon-carbon bonds, and two or more condensed ring aryl groups connected by carbon-carbon bonds. That is, unless otherwise specified, two or more aromatic groups connected by carbon-carbon bonds can also be regarded as aryl groups of the present application. Among them, condensed ring aryl groups can, for example, include bicyclic condensed aryl groups (e.g., naphthyl), tricyclic condensed aryl groups (e.g., phenanthrenyl, fluorenyl, anthracenyl), etc. The aryl group does not contain heteroatoms such as B, N, O, S, P, Se, and Si. Examples of aryl groups include, but are not limited to, phenyl, naphthyl, fluorenyl, spirobifluorenyl, anthracenyl, phenanthrenyl, biphenyl, terphenyl, triphenylene, peryl, benzo[9,10]phenanthrenyl, pyrenyl, benzofluoranthenyl, Ji et al.

[0050] In the present application, "arylene group" refers to a divalent group formed by further losing one or more hydrogen atoms from an aryl group.

[0051] In the present application, terphenyl includes

[0052] In the present application, the carbon number of the substituted or unsubstituted aryl (arylene) group can be 6, 8, 10, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 30. In some embodiments, the substituted or unsubstituted aryl group is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, in other embodiments, the substituted or unsubstituted aryl group is a substituted or unsubstituted aryl group having 6 to 25 carbon atoms, in other embodiments, the substituted or unsubstituted aryl group is a substituted or unsubstituted aryl group having 6 to 18 carbon atoms, and in other embodiments, the substituted or unsubstituted aryl group is a substituted or unsubstituted aryl group having 6 to 15 carbon atoms.

[0053] In the present application, the fluorenyl group may be substituted by one or more substituents. When the fluorenyl group is substituted, the substituted fluorenyl group may be: etc., but not limited thereto.

[0054] In the present application, the aryl group as a substituent of L, L1, L2, Ar1 and Ar2 is exemplified but not limited to phenyl, naphthyl, phenanthrenyl, biphenyl, fluorenyl, dimethylfluorenyl and the like.

[0055] In the present application, heteroaryl refers to a monovalent aromatic ring or a derivative thereof containing 1, 2, 3, 4, 5 or 6 heteroatoms in the ring, and the heteroatoms may be one or more of B, O, N, P, Si, Se and S. The heteroaryl may be a monocyclic heteroaryl or a polycyclic heteroaryl, in other words, the heteroaryl may be a single aromatic ring system or a plurality of aromatic ring systems conjugated by carbon-carbon bonds, and any aromatic ring system may be an aromatic monocyclic ring or an aromatic condensed ring. By way of example, the heteroaryl group may include a thienyl group, a furyl group, a pyrrolyl group, an imidazolyl group, a thiazolyl group, an oxazolyl group, an oxadiazolyl group, a triazolyl group, a pyridyl group, a bipyridyl group, a pyrimidyl group, a triazine group, an acridinyl group, a pyridazinyl group, a pyrazinyl group, a quinolyl group, a quinazolinyl group, a quinoxalinyl group, a phenoxazinyl group, a phthalazinyl group, a pyridopyrimidinyl group, a pyridopyrazinyl group, a pyrazinopyrazinyl group, an isoquinolyl group, an indolyl group, a carbazolyl group, a benzoxazolyl group, a benzimidazolyl group, a benzothiazolyl group, a benzocarbazolyl group, a benzothienyl group, a dibenzothienyl group, a thienothiphenyl group, a benzofuranyl group, a phenanthrolinyl group, an isoxazolyl group, a thiadiazolyl group, a phenothiazinyl group, a silyfluorenyl group, a dibenzofuranyl group, and an N-phenylcarbazolyl group, an N-pyridylcarbazolyl group, an N-methylcarbazolyl group, and the like, without being limited thereto.

[0056] In the present application, the heteroarylene group refers to a divalent or multivalent group formed by further losing one or more hydrogen atoms from a heteroaryl group.

[0057] In the present application, the number of carbon atoms of the substituted or unsubstituted heteroaryl (heteroarylene) can be selected from 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30. In some embodiments, the substituted or unsubstituted heteroaryl is a substituted or unsubstituted heteroaryl having a total carbon number of 12 to 18, and in other embodiments, the substituted or unsubstituted heteroaryl is a substituted or unsubstituted heteroaryl having a total carbon number of 5 to 12.

[0058] In the present application, the heteroaryl group as a substituent of L, L1, L2, Ar1 and Ar2 is, for example but not limited to, pyridyl, carbazolyl, dibenzothiophenyl, dibenzofuranyl, benzoxazolyl, benzothiazolyl, benzimidazolyl.

[0059] In the present application, the substituted heteroaryl group may be a heteroaryl group in which one or more hydrogen atoms are replaced by groups such as a deuterium atom, a halogen group, -CN, an aryl group, a heteroaryl group, a trialkylsilyl group, an alkyl group, a cycloalkyl group, a haloalkyl group, and the like.

[0060] In the present application, the alkyl group having 1 to 10 carbon atoms may include a straight-chain alkyl group having 1 to 10 carbon atoms and a branched-chain alkyl group having 3 to 10 carbon atoms. The number of carbon atoms in the alkyl group may be, for example, 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10, and specific examples of the alkyl group include, but are not limited to, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl, neopentyl, n-hexyl, and the like.

[0061] In the present application, the halogen group may be, for example, fluorine, chlorine, bromine, or iodine.

[0062] In the present application, specific examples of trialkylsilyl include, but are not limited to, trimethylsilyl, triethylsilyl, and the like.

[0063] In the present application, specific examples of the haloalkyl group include, but are not limited to, trifluoromethyl.

[0064] In the present application, the carbon number of the cycloalkyl group having 3 to 10 carbon atoms may be, for example, 3, 4, 5, 6, 7, 8 or 10. Specific examples of the cycloalkyl group include, but are not limited to, cyclopentyl, cyclohexyl, and adamantyl.

[0065] In the present application, the carbon number of the deuterated alkyl group having 1 to 10 carbon atoms is, for example, 1, 2, 3, 4, 5, 6, 7, 8 or 10. Specific examples of the deuterated alkyl group include, but are not limited to, trideuterated methyl group.

[0066] In the present application, the carbon number of the haloalkyl group having 1 to 10 carbon atoms is, for example, 1, 2, 3, 4, 5, 6, 7, 8 or 10. Specific examples of the haloalkyl group include, but are not limited to, trifluoromethyl.

[0067] In the present application, a ring system formed by n atoms is 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 ring, benzene ring, etc.

[0068] In this application, Refers to the chemical bonds that connect to other groups.

[0069] In this application, no single bond extending from the ring system is involved in the positioning of the connecting bond. It means that one end of the connecting bond can be connected to any position in the ring system that the bond passes through, and the other end is connected to the rest of the compound molecule. For example, as shown in the following formula (f), the naphthyl represented by formula (f) is connected to other positions of the molecule through two non-positional connecting bonds that pass through the bicyclic ring, and the meaning represented by it includes any possible connection mode shown in formula (f-1) to formula (f-10).

[0070]

[0071] For another example, as shown in the following formula (X'), the dibenzofuranyl represented by formula (X') is connected to other positions of the molecule through a non-positional connecting bond extending from the middle of one side of the benzene ring, and its meaning includes any possible connection method shown in formulas (X'-1) to (X'-4).

[0072]

[0073] The non-positioning substituent in the present application refers to a substituent connected by a single bond extending from the center of the ring system, which means that the substituent can be connected to any possible position in the ring system. For example, as shown in the following formula (Y), the substituent R' represented by formula (Y) is connected to the quinoline ring through a non-positioning connection bond, and the meaning represented includes any possible connection mode shown in formula (Y-1) to formula (Y-7).

[0074]

[0075] In some embodiments, the organic compound has a structure shown in Formula I-1 to I-3:

[0076]

[0077] Wherein, X, L, L1, L2, Ar1, Ar2, R1, R2, R3, n1, n2, n3, and m are defined the same as in Formula I.

[0078] In some embodiments, the organic compound has a structure shown in Formula Ia to Il:

[0079]

[0080] Wherein, L, L1, L2, Ar1, Ar2, R1, R2, R3, n1, n2, n3, and m are defined the same as in Formula I.

[0081] In some embodiments, X is selected from a single bond, C(R4R5), O, or S.

[0082] Optionally, R4 and R5 are each independently selected from hydrogen, an alkyl group having 1 to 6 carbon atoms, or an aryl group having 6 to 15 carbon atoms.

[0083] Optionally, R4 and R5 are each independently selected from methyl, ethyl, n-propyl, isopropyl or phenyl.

[0084] In some embodiments, X is selected from a single bond or O.

[0085] Optionally, R1, R2 and R3 are the same or different and are each independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, cyclohexyl, phenyl, deuterated phenyl or naphthyl.

[0086] In some embodiments, Ar1 and Ar2 are each independently selected from a substituted or unsubstituted aryl group having 6 to 25 carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 18 carbon atoms; for example, Ar1 and Ar2 are each independently selected from a substituted or unsubstituted aryl group having 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24 or 25 carbon atoms, or a substituted or unsubstituted heteroaryl group having 5, 6, 7, 8, 9, 10, 12, 13, 14, 15, 16, 17 or 18 carbon atoms.

[0087] Optionally, the substituents in Ar1 and Ar2 are the same or different and are independently selected from deuterium, fluorine, cyano, trimethylsilyl, alkyl having 1 to 5 carbon atoms, cycloalkyl having 5 to 10 carbon atoms, haloalkyl having 1 to 5 carbon atoms, aryl having 6 to 12 carbon atoms or heteroaryl having 5 to 12 carbon atoms. Optionally, any two adjacent substituents in Ar1 form a saturated or unsaturated ring having 5 to 13 carbon atoms. Optionally, any two adjacent substituents in Ar2 form a saturated or unsaturated ring having 5 to 13 carbon atoms.

[0088] In some embodiments, Ar1 and Ar2 are each independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted spirobifluorenyl.

[0089] Optionally, the substituents in Ar1 and Ar2 are each independently selected from deuterium, fluorine, cyano, trimethylsilyl, trifluoromethyl, methyl, ethyl, isopropyl, tert-butyl, phenyl, naphthyl, dibenzofuranyl, dibenzothienyl or carbazolyl.

[0090] In some embodiments, Ar1 and Ar2 are each independently selected from a substituted or unsubstituted group W, and the unsubstituted group W is selected from the group consisting of the following groups:

[0091]

[0092] The substituted group W has one or more substituents, each of which is independently selected from deuterium, fluorine, cyano, trimethylsilyl, trifluoromethyl, methyl, ethyl, isopropyl, tert-butyl, phenyl, naphthyl, dibenzofuranyl, dibenzothienyl or carbazolyl, and when the number of substituents in the group W is greater than 1, each substituent is the same or different.

[0093] In some embodiments, Ar1 and Ar2 are each independently selected from the group consisting of:

[0094]

[0095]

[0096] In some embodiments, L, L1 and L2 are the same or different, and are each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 18 carbon atoms, and a substituted or unsubstituted heteroarylene group having 5 to 18 carbon atoms. For example, L, L1 and L2 are each independently selected from a single bond, a substituted or unsubstituted arylene group having 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17 or 18 carbon atoms, and a substituted or unsubstituted heteroarylene group having 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17 or 18 carbon atoms.

[0097] Optionally, the substituents in L, L1 and L2 are each independently selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 5 carbon atoms, a haloalkyl group having 1 to 5 carbon atoms, a deuterated alkyl group having 1 to 5 carbon atoms, a trialkylsilyl group having 3 to 8 carbon atoms, an aryl group having 6 to 10 carbon atoms or a heteroaryl group having 5 to 12 carbon atoms.

[0098] In some embodiments, L, L1 and L2 are each independently selected from a single bond, a substituted or unsubstituted phenylene, a substituted or unsubstituted naphthylene, a substituted or unsubstituted biphenylene, a substituted or unsubstituted terphenylene, a substituted or unsubstituted fluorenylene, a substituted or unsubstituted carbazolylene, a substituted or unsubstituted dibenzothiophenylene, and a substituted or unsubstituted dibenzofuranylene.

[0099] Optionally, the substituents in L, L1 and L2 are each independently selected from deuterium, fluorine, cyano, trimethylsilyl, trideuterated methyl, trifluoromethyl, methyl, ethyl, isopropyl, tert-butyl, phenyl or naphthyl.

[0100] In some embodiments, L1 and L2 are each independently selected from a single bond or the group consisting of:

[0101]

[0102] In some embodiments, each L is independently selected from a single bond, a substituted or unsubstituted phenylene, a substituted or unsubstituted naphthylene, a substituted or unsubstituted biphenylene, a substituted or unsubstituted fluorenylene, a substituted or unsubstituted carbazolylene, a substituted or unsubstituted dibenzothiophenylene, or a substituted or unsubstituted dibenzofuranylene.

[0103] Optionally, the substituents in L are selected from deuterium, fluorine, cyano, trimethylsilyl, trideuteratedmethyl, trifluoromethyl, methyl, ethyl, isopropyl, tert-butyl, phenyl or naphthyl.

[0104] In some embodiments, each L is independently selected from the group consisting of a single bond or the following groups:

[0105]

[0106] In some embodiments, is selected from the group consisting of a single bond or the following groups:

[0107]

[0108] In some embodiments, L1 and L2 are each independently selected from a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted biphenylene group, and a substituted or unsubstituted carbazolylene group.

[0109] Optionally, the substituents in L1 and L2 are each independently selected from deuterium, fluorine, cyano, trimethylsilyl, trideuterated methyl, trifluoromethyl, methyl, ethyl, isopropyl, tert-butyl, phenyl or naphthyl.

[0110] In some embodiments, L1 and L2 are each independently selected from a single bond or the group consisting of:

[0111]

[0112] In some embodiments, L1 and L2 are each independently selected from a single bond or the group consisting of:

[0113]

[0114]

[0115] In some embodiments, Each is independently selected from the group consisting of:

[0116]

[0117] Specifically, the organic compound can be selected from the group consisting of the following compounds:

[0118]

[0119]

[0120]

[0121]

[0122]

[0123]

[0124]

[0125] In a second aspect, the present application provides an organic electroluminescent device, comprising an anode, a cathode, and a functional layer disposed between the anode and the cathode; wherein the functional layer comprises the organic compound described in the first aspect of the present application.

[0126] 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 that are arranged opposite to each other, and a functional layer 300 arranged between the anode 100 and the cathode 200; the functional layer 300 contains the organic compound provided in the present application.

[0127] Optionally, the functional layer 300 includes a hole transport layer 321, which is located between the anode and the organic light-emitting layer. The hole transport layer 321 includes the organic compound provided in the present application, and the hole transport layer 321 can be composed of the organic compound provided in the present application, or can be composed of the organic compound provided in the present application and other materials.

[0128] In a specific embodiment of the present application, the organic electroluminescent device may include an anode 100, a hole transport layer 321, a hole auxiliary layer 322, an organic electroluminescent layer 330 as an energy conversion layer, an electron transport layer 340, and a cathode 200 stacked in sequence. The organic compound provided in the present application can be applied to the hole transport layer 321 of the organic electroluminescent device, effectively improving the luminous efficiency, lifespan and thermal stability of the organic electroluminescent device, and reducing the driving voltage of the organic electroluminescent device.

[0129] In the present application, the anode 100 includes an anode material, which is 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 their alloys; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO) and indium zinc oxide (IZO); combined 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 not limited thereto. Optionally, a transparent electrode including indium tin oxide (indium tin oxide) (ITO) as an anode is included.

[0130] Optionally, a hole injection layer 310 is further provided 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 made of benzidine derivatives, starburst arylamine compounds, phthalocyanine derivatives or other materials, and the present application does not impose any particular limitation thereto. The material of the hole injection layer 310 is, for example, selected from the following compounds or any combination thereof;

[0131]

[0132]

[0133] In one embodiment of the present application, the hole injection layer 310 is composed of HAT-CN.

[0134] Optionally, the electron blocking layer 322 includes one or more electron blocking materials, and the electron blocking materials can be selected from carbazole polymers or other types of compounds, which are not specifically limited in the present application. For example, in some embodiments of the present application, the electron blocking layer 322 is composed of compound EB-01 composition.

[0135] Optionally, the organic light-emitting layer 330 may be composed of a single light-emitting material, or 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, and holes injected into the organic light-emitting layer 330 and electrons injected into the organic light-emitting layer 330 may be recombined in the organic light-emitting layer 330 to form excitons, and 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.

[0136] The main material of the organic light emitting layer 330 may include metal chelate compounds, bisphenylethylene derivatives, aromatic amine derivatives, dibenzofuran derivatives or other types of materials. The main material of the organic light emitting layer 330 may be one compound or a combination of two or more compounds.

[0137] In one embodiment of the present application, the main material of the organic light-emitting layer 330 is BH-01

[0138] The guest material of the organic light-emitting layer 330 can be a compound having a condensed aromatic ring or a derivative thereof, a compound having a heteroaromatic ring or a derivative thereof, an aromatic amine derivative or other materials, and the present application does not impose any special restrictions on this. The guest material is also called a doping material or a dopant. Specific examples of the dopant include, but are not limited to,

[0139]

[0140]

[0141] In some specific embodiments of the present application, the guest material of the organic light-emitting layer 330 is BD-01.

[0142] The electron transport layer 340 may be a single-layer structure or a multi-layer structure, and may include one or more electron transport materials, which may be selected from but not limited to LiQ, benzimidazole derivatives, oxadiazole derivatives, quinoxaline derivatives or other electron transport materials, and the present application does not specifically limit this. The materials of the electron transport layer 340 include but are not limited to the following compounds:

[0143]

[0144] In one embodiment of the present application, the electron transport layer 340 is composed of ET-18 and LiQ.

[0145] In the present application, cathode 200 includes a cathode material, which is a material with a small work function that facilitates electron injection into the functional layer. 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.

[0146] Optionally, an electron injection layer 350 is further provided between the cathode 200 and the electron transport layer 340 to enhance the ability to inject electrons into the electron transport layer 340. The electron injection layer 350 may include inorganic materials such as alkali metal sulfides and alkali metal halides, or may include a complex of an alkali metal and an organic substance. In one embodiment of the present application, the electron injection layer 350 includes LiF.

[0147] A third aspect of the present application provides an electronic device, comprising the organic electroluminescent device described in the second aspect of the present application.

[0148] According to one embodiment, Figure 2 As shown, the provided electronic device is an electronic device 400, which includes the above-mentioned organic electroluminescent device. The 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 but not limited to a computer screen, a mobile phone screen, a television, an electronic paper, an emergency lighting lamp, an optical module, etc.

[0149] The synthesis method of the organic compound of the present application is specifically described below in conjunction with synthesis examples, but the present application is not limited thereto.

[0150] Synthesis Example

[0151] Those skilled in the art will recognize that the chemical reactions described herein can be used to appropriately prepare many of the organic compounds of the present invention, and that other methods for preparing the compounds of the present invention are considered to be within the scope of the present invention. For example, the synthesis of the compounds not exemplified herein can be successfully accomplished by those skilled in the art by modification methods, such as appropriate protection of interfering groups, by utilizing other known reagents in addition to those described herein, or by making some conventional modifications to the reaction conditions. The compounds for which no synthesis methods are mentioned in the present invention are raw materials obtained from commercial sources.

[0152] The compounds in this application are prepared by reacting IM-I and IM-II intermediates (including some intermediates that can be directly purchased). The synthesis methods of the two types of intermediates are listed below:

[0153] 1. Synthesis of intermediate IM-I-a1

[0154]

[0155] (1) Under N2 protection, raw material Sub-I-a1 (80.0 g, 299.39 mmol), 2-methoxycarbonylphenylboronic acid pinacol ester (78.5 g, 299.40 mmol), potassium carbonate (91.0 g, 658.65 mmol), toluene (700 mL), ethanol (350 mL), and water (150 mL) were added to a three-necked flask in sequence, and the mixture was stirred and heated to 50-60°C. Tetrakis(triphenylphosphine)palladium (6.9 g, After the addition, the temperature was continued to rise to 70-75 ° C and refluxed for 12 hours. After the reaction was completed, the temperature was naturally cooled to room temperature and extracted with dichloromethane. After separation, the organic phase was washed with water until neutral, and then dried, filtered and concentrated to obtain a crude product, which was recrystallized with a mixed solvent of ethyl acetate and n-heptane. The obtained white solid was the intermediate IM-I-a1-1# (77.0 g, yield 79.8%).

[0156]

[0157] (2) At room temperature, NaOH (38.2 g, 955.19 mmol) was dissolved in 400 mL of deionized water, stirred to fully dissolve, and then 400 mL of methanol was added to the solution to obtain a mixed alkali solution of NaOH / methanol / water. The intermediate IM-I-a1-1# (76.6 g, 237.56 mmol) and the above mixed alkali solution were added to a 1L three-necked flask, heated to 50°C and stirred for hydrolysis for 24 hours. After the reaction was completed, the methanol was distilled off under reduced pressure, and 300 mL of deionized water was added to dilute the reaction solution, and then 3M dilute hydrochloric acid was added to adjust the pH to 2-3, followed by extraction with dichloromethane and deionized water. After separation, the organic phase was dried over anhydrous magnesium sulfate, filtered, and the solvent was distilled off under reduced pressure. The resulting white solid was the intermediate IM-I-a1-2# (60.5 g, yield 82.6%).

[0158]

[0159] (3) Under N2 protection, the intermediate IM-I-a1-2# (60.0 g, 194.54 mmol), (1,5-cyclooctadiene)rhodium chloride (I) dimer (Cas: 12092-47-6, 2.4 g, 4.86 mmol), 1,2-bis(diphenylphosphine)ethane (DPPE, 3.9 g, 9.73 mmol), potassium iodide (16.1 g, 97.25 mmol), pivalic anhydride (Piv2O, 108.7 g, 5 83.62mmol), the reaction bottle was placed in a microwave reactor and heated to 200°C for 30min, the reaction was stopped and the temperature was cooled to room temperature, then extracted with dichloromethane / deionized water, the organic phase was washed with water to neutrality after separation, and then separated, dried, filtered and concentrated to obtain a yellow solid crude product, which was then passed through a silica gel column with dichloromethane / n-hexane (volume ratio of 1:5) as the mobile phase, and then the solvent was distilled off under reduced pressure to obtain a white solid intermediate IM-I-a1 (53.2g, yield 94.2%).

[0160] 2. Synthesis of intermediate IM-I-a2

[0161]

[0162] The intermediate IM-I-a2 was prepared by the same method as the intermediate IM-I-a1, except that: the raw material Sub-I-a2 (30.0 g, 112.27 mmol) was used to replace the raw material Sub-I-a1 in step (1), and the other raw materials remained unchanged, to obtain the intermediate IM-I-a2-1# (26.2 g, yield 72.4%); the intermediate IM-I-a2-1# (26.0 g, 80.63 mmol) was used to replace the intermediate IM-I-a1-1# in step (2) to obtain the intermediate IM-I-a2-2# (19.8 g, yield 79.5%); the intermediate IM-I-a2-2# (19.5 g, 63.23 mmol) was used to replace the intermediate IM-I-a1-2# in step (3) to obtain the intermediate IM-I-a2 (16.7 g, yield 91.1%).

[0163] 3. Synthesis of intermediate IM-I-b1:

[0164]

[0165] (1) Under N2 protection, raw material Sub-I-b1 (40.0 g, 195.79 mmol), o-chlorobenzoic acid (32.2 g, 205.59 mmol), potassium carbonate (40.6 g, 293.68 mmol), copper powder (0.25 g, 3.92 mmol), cuprous iodide (0.75 g, 3.92 mmol), and anisole (350 mL) were added to a three-necked flask in sequence, and the mixture was stirred and refluxed for 5 h. After the reaction was completed, the mixture was naturally cooled to room temperature and extracted with dichloromethane / deionized water. After separation, the organic phase was washed with water until neutral, and then dried, filtered, and concentrated. The obtained pale yellow solid crude product was purified by recrystallization with ethyl acetate and n-hexane. The obtained white solid was the intermediate IM-I-b1-1# (43.7 g, yield 68.8%).

[0166]

[0167] (2) Under N2 protection, add intermediate IM-I-b1-1# (43.2 g, mmol) and 200 mL of concentrated sulfuric acid (mass fraction ≥ 98%) to an enamel reactor with a polytetrafluoroethylene stirring rod and stir at room temperature for 1 h. After the reaction, slowly pour the reaction solution into ice water, filter to obtain a white solid, wash with deionized water until neutral, and dry to obtain a white solid, which is intermediate IM-I-b1 (26.8 g, yield 65.8%).

[0168] The intermediate IM-I-xm in Table 1 was prepared by the same method as the intermediate IM-I-b1, except that the raw material 1 in Table 1 was used to replace Sub-I-b1, and the raw material 2 was used to replace o-chlorobenzoic acid, and other conditions remained unchanged.

[0169] Table 1

[0170]

[0171] 4. Synthesis of intermediate IM-I-d1

[0172] Referring to the synthesis method disclosed in patent CN109867652, the specific synthesis process is as follows:

[0173]

[0174] (1) Under N2 protection, the raw material Sub-I-a1 (50.0 g, 187.12 mmol) and 400 mL of dry THF were added to a 2L three-necked flask, stirred at 0°C for 15 min to completely dissolve the raw materials, and then magnesium chips (4.9 g, 204.22 mmol) were added and refluxed for 3 hours. After the reaction was completed, the newly prepared Grignard reagent was slowly dripped into 250 mL of 2-chloromethylbenzoic acid methyl ester (34.5 g, 187.12 mmol) tetrahydrofuran solution at 0°C. The mixture was stirred for 30 minutes, naturally heated to room temperature and stirred for 24 hours. After the reaction was completed, water was slowly dripped into the reaction flask for quenching, extracted with ethyl acetate and distilled water, and filtered with anhydrous magnesium sulfate. Recrystallization and purification were performed using ethyl acetate and n-hexane to obtain the intermediate compound IM-I-d1-1# (30.5 g, yield 72.0%).

[0175]

[0176] (2) After adding compound IM-I-d1-1# (30.0 g, 132.46 mmol) and 450 ml of ether to a 2 L reaction flask, stir and cool to -78 ° C. Under the protection of N2, slowly drop 166 mL of 1.6 M methyl lithium ether solution (265.60 mmol) into the reaction flask. After the reaction is completed and kept warm for 1 hour, the temperature is naturally raised to room temperature and stirred for 24 hours. After the reaction is completed, methanol is slowly added dropwise to the reaction system, extracted with ethyl acetate, and filtered with anhydrous magnesium sulfate. Recrystallize and purify using dichloromethane and n-hexane to obtain a white solid, the intermediate compound IM-I-d1-2# (34.1 g, yield 76.5%).

[0177]

[0178] (3) Add compound IM-I-d1-2# (32.3 g, 95.98 mmol) and 300 mL of dichloromethane to a three-necked flask, stir and dissolve completely, then add 6 mL of concentrated sulfuric acid (mass fraction ≥ 98%) under N2 protection, and stir at room temperature for 2 hours. After the reaction is completed, slowly add the reactants into ice water. After the reaction system is cooled to room temperature, slowly add a 5% NaOH aqueous solution and adjust to pH = 7. Extract the reaction solution with dichloromethane and distilled water, and filter with anhydrous magnesium sulfate. Recrystallize and purify using dichloromethane and n-hexane to obtain a white solid, the intermediate compound IM-I-d1-3# (26.3 g, yield 86.0%)

[0179]

[0180] (4) Add compound IM-I-d1-3# (26.0 g, 81.63 mmol) and 150 ml of glacial acetic acid to a 2 L reaction flask, stir and heat to 55°C to 58°C. Under N2 protection, slowly drop 80 mL of glacial acetic acid solution containing chromium trioxide (9.8 g, 97.96 mmol) into the reaction flask and stir at 55°C to 58°C for 4 hours. After the reaction is completed, remove the solvent by distillation under reduced pressure, add 150 ml of deionized water to the residue and stir for 10 minutes to disperse the solid. After filtering, wash the filter cake with deionized water, extract with dichloromethane and distilled water, and filter the organic phase after passing through anhydrous magnesium sulfate. The obtained pale yellow solid crude product is recrystallized with ethanol and water in a volume ratio of 3:1 to obtain a white solid, the intermediate compound IM-I-d1 (18.8 g, yield 69.3%)

[0181] The intermediates IM-I-g1 and IM-I-g2 in Table 2 were prepared by the same method as the intermediate IM-I-d1, except that the raw material 3 in Table 2 was used to replace the 2-chloromethylbenzoic acid methyl ester in step (1), and other conditions remained unchanged. The intermediates and product structures and yields (the yield of the last step) obtained in each step are listed in Table 2.

[0182] Table 2

[0183]

[0184] 5. Synthesis of intermediate IM-I-A1

[0185]

[0186] In a three-necked flask, add 2-bromo-4'-chloro-1,1'-biphenyl (22.0 g, 82.23 mmol) and anhydrous tetrahydrofuran (200 mL) in sequence, stir and cool to -78 °C under nitrogen protection, slowly drop 2M n-butyl lithium n-hexane solution (45 mL, 90.00 mmol), keep warm and stir for 2 h after the addition is complete, then add 200 mL of anhydrous tetrahydrofuran solution dissolved with IM-I-a1 (23.9 g, 82.23 mmol), keep warm and stir for 30 min, and continue to heat to room temperature naturally. After stirring for 2 hours, 1M hydrochloric acid solution (100 mL, 100 mmol) was slowly dripped into the reaction flask for sufficient hydrolysis, and the reaction solution was extracted with ethyl acetate. The organic phase was dried over magnesium sulfate and distilled under reduced pressure. 200 mL of glacial acetic acid and 4 mL of concentrated sulfuric acid were added to the obtained pale yellow solid crude product, and the mixture was heated under reflux and stirred for 2 hours. After the reaction solution was cooled to room temperature, it was slowly poured into 400 mL of deionized water to precipitate a white solid, which was filtered and rinsed with deionized water until neutral. The obtained solid was recrystallized from ethyl acetate to obtain the intermediate IMA1 (20.5 g, yield 44.48%).

[0187] The intermediate IM-I-Xn in Table 3 was prepared by the same method as the intermediate IM-I-A1, except that: the raw material 4 was used to replace 2-bromo-4'-chloro-1,1'-biphenyl, and the intermediate IM-I-xm in Table 3 was used to replace the intermediate IM-I-a1, and other conditions remained unchanged. The structures and yields of the obtained products are shown in Table 3.

[0188] Table 3

[0189]

[0190]

[0191]

[0192] 6. Synthesis of intermediate IM-I-A1-L

[0193]

[0194] (1) IM-I-A1 (6.0 g, 13.04 mmol) and 1,4-dioxane (60 ml) were added to a 100 ml three-necked reaction flask, nitrogen was passed through, and then diboric acid pinacol ester (3.5 g, 13.82 mmol) and potassium acetate (2.56 g, 26.08 mol) were added in sequence. The temperature was raised to 80°C to 90°C under mechanical stirring, and Pd2(dba)3 (0.12 g, 0.13 mmol) and x-phos (0.12 g, 0.26 mmol) were quickly added. The temperature was maintained at 80°C to 90°C for 12 hours. After the reaction was completed, the temperature was lowered to room temperature, the reaction solution was extracted with toluene, washed with water, and the organic phase was dried over anhydrous magnesium sulfate after separation to obtain a crude product. The crude product was recrystallized from toluene to obtain IM-I-A1-Bpe (5.4 g, yield 74.9%).

[0195]

[0196] (2) The intermediate IM-I-A1-L was prepared by the same method as the intermediate IM-I-a1-1#, except that the intermediate IM-I-A1-Bpe (6.0 g, 10.86 mmol) was used instead of the raw material Sub-I-a1, and 2-bromo-7-chloronaphthalene (2.6 g, 10.86 mmol) was used instead of 2-methoxycarbonylphenylboronic acid pinacol ester, and the other raw materials and reaction conditions remained unchanged to obtain the intermediate IM-I-A1-L (4.8 g, yield 75.4%).

[0197] The intermediate IM-I-Xn-L in Table 4 was synthesized by referring to the synthesis method of IM-I-A1-L, except that: first, the intermediate IM-I-Xn in Table 4 was used to replace the intermediate IM-I-A1 to synthesize the intermediate IM-I-Xn-Bpe; then, the intermediate IM-I-A1-Bpe was replaced by IM-I-Xn-Bpe, and the raw material 5 was used to replace 2-bromo-7-chloronaphthalene. The other raw materials and conditions remained unchanged. The products and yields of the two-step reactions are shown in Table 4.

[0198] Table 4

[0199]

[0200]

[0201] 7. Synthesis of intermediate IM-Ⅱ-N1

[0202]

[0203] Under nitrogen protection, 2-bromobiphenyl (10.0 g, 42.90 mmol), 3-aminobiphenyl (7.6 g, 45.04 mmol), tris(dibenzylideneacetone)dipalladium (0.4 g, 0.42 mmol), 2-dicyclohexylphosphine-2',6'-dimethoxybiphenyl (0.4 g, 0.85 mmol) and sodium tert-butoxide (6.2 g, 64.35 mmol) were added to toluene (100 mL) in a reaction bottle, heated to 108°C under nitrogen protection, and stirred for 3 h; then cooled to room temperature, the reaction solution was washed with water and dried with magnesium sulfate, filtered, and the filtrate was decompressed to remove the solvent to obtain a yellow solid crude product; the crude product was then recrystallized and purified using toluene / n-hexane to obtain intermediate IM B1 (10.4 g, yield 75.5%).

[0204] The intermediate IM-Ⅱ-Nx in Table 5 was synthesized by referring to the synthesis method of intermediate IM-Ⅱ-N1, except that: raw material 6 was used to replace 2-bromobiphenyl, and raw material 7 was used to replace 3-aminobiphenyl, and other raw materials and conditions remained unchanged. The structures and yields of the obtained products are shown in Table 5.

[0205] Table 5

[0206]

[0207]

[0208] Synthesis of compounds: Taking compound A04 as an example

[0209]

[0210] Under N2 protection, the intermediate IM-I-A1 (4.7 g, 10.19 mmol), di(4-biphenyl)amine (3.3 g, 10.20 mmol), tri(dibenzylideneacetone)dipalladium (0.1 g, 0.11 mmol), 2-dicyclohexylphosphine-2',6'-dimethoxybiphenyl (0.1 g, 0.22 mmol) and sodium tert-butoxide (1.47 g, 15.29 mmol) were added to a round-bottom flask in sequence and added to toluene (40 mL). The mixture was heated to 108°C under nitrogen protection and stirred for 4 h; then cooled to room temperature, the reaction solution was washed with water and dried with magnesium sulfate, filtered, and the filtrate was decompressed to remove the solvent, and the crude product was purified by recrystallization with toluene / n-hexane to obtain a white solid compound (4.3 g, yield 56.6%). Mass spectrum LC-MS (ESI, pos.ion): m / z=776.4[M+H] + .

[0211] The compounds in Table 6 were prepared by the same method as compound A04, except that the raw material 8 in Table 6 was used instead of intermediate IM-I-A1, and the raw material 9 was used instead of di(4-biphenyl)amine, and other conditions remained unchanged. The structures of the raw materials used, the product structures and the yields are all listed in Table 6.

[0212] Table 6

[0213]

[0214]

[0215]

[0216]

[0217] The NMR data of some compounds are shown in Table 7:

[0218] Table 7

[0219]

[0220]

[0221] Embodiment 1:

[0222] This embodiment provides an organic electroluminescent device, and the specific preparation method is as follows:

[0223] The glass plate coated with the ITO transparent conductive layer was ultrasonically treated in a commercial cleaning agent, rinsed in deionized water, ultrasonically degreased in an acetone:ethanol mixed solvent, baked in a clean environment to completely remove moisture, and surface treated with ultraviolet ozone and O2:N2 plasma to increase the work function of the anode and remove scum.

[0224] Place the glass substrate with the anode in a vacuum chamber and evacuate the chamber to a vacuum of less than 1×10 -5 Pa, vacuum evaporating a compound HAT-CN on the anode layer film to form a hole injection layer (HIL) with a thickness of 10 nm;

[0225] Compound A04 is vacuum-deposited on the electron injection layer to form a layer with a thickness of A hole transport layer (HTL);

[0226] Compound EB-01 was vacuum-deposited on the hole transport layer to form a layer with a thickness of An electron blocking layer (EBL);

[0227] The light-emitting layer of the device is vacuum-evaporated on the electron blocking layer. Compound BH-01 (host) and compound BD-01 (doped guest) are co-evaporated at a mass ratio of 97%:3% by using a multi-source co-evaporation method to form a layer with a thickness of of an organic light-emitting layer (EML).

[0228] On the organic light-emitting layer, compound ET-18 and LiQ were evaporated at a weight ratio of 1:1 to form a layer with a thickness of The electron transport layer (ETL);

[0229] The thickness of the vacuum evaporation on the electron transport layer (ETL) is LiF was used as an electron injection layer (EIL), and magnesium (Mg) and silver (Ag) were co-evaporated on the electron injection layer at an evaporation rate of 1:9 (mass ratio) to form a layer with a thickness of cathode.

[0230] In addition, the thickness of the vacuum evaporation layer on the cathode is The CP-01 forms an organic cover layer (CPL), thereby completing the manufacture of the organic electroluminescent device.

[0231] Example 2-Example 27:

[0232] An organic electroluminescent device was prepared by the same method as in Example 1, except that, when preparing the hole transport layer, the compound in Table 8 was used instead of Compound A04 in Example 1.

[0233] Comparative Example 1-Comparative Example 3:

[0234] An organic electroluminescent device was prepared by the same method as in Example 1, except that, when preparing the hole transport layer, Compounds A to C in Table 8 were used instead of Compound A04 in Example 1.

[0235] When preparing the organic electroluminescent device, the structures of the materials used in the comparative examples and the examples are as follows:

[0236]

[0237]

[0238] The performance of the organic electroluminescent devices prepared in Examples 1-27 and Comparative Examples 1-3 was tested. Specifically, at 10 mA / cm 2 The IVL performance of the device was tested under the conditions of T 95 Device life at 15mA / cm 2 The test was carried out under the conditions of , and the test results are shown in Table 8 below.

[0239] Table 8

[0240]

[0241]

[0242] Referring to Table 8 above, it can be seen that compared with the organic electroluminescent devices of Comparative Examples 1-3, the performance of the organic electroluminescent devices of Examples 1-27 is greatly improved, mainly manifested in that the operating voltage of the device is slightly reduced, the luminous efficiency is increased by at least 12.5%, and the T95 life is increased by at least 18.3%. It can be seen that using the organic compound of the present application in the hole transport layer of the organic electroluminescent device can significantly improve the luminous efficiency and T95 life of the organic electroluminescent device. 95 life.

[0243] The preferred embodiments of the present invention are described in detail above. However, the present invention is not limited to the specific details in the above embodiments. Within the technical concept of the present invention, a variety of simple modifications can be made to the technical solution of the present invention, and these simple modifications all belong to the protection scope of the present invention.

Claims

1. An organic compound having a structure shown in Formula I: in, X is selected from a single bond, C(R4R5), O or S; R4 and R5 are the same or different and are each independently selected from methyl, ethyl, n-propyl, isopropyl or phenyl; R1, R2 and R3 are the same or different and are independently selected from deuterium, cyano, halogen group, and alkyl group with 1 to 10 carbon atoms; m is the number of L connected in sequence, m is selected from 1 or 2; n1 is the number of R1, and n1 is selected from 0, 1, 2, 3 or 4; when n1 is greater than 1, any two R1 are the same or different; 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; n3 is the number of R3, and n3 is selected from 0, 1, 2, 3 or 4; when n3 is greater than 1, any two R3 are the same or different; L, L1 and L2 are the same or different and are each independently selected from a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted fluorenylene group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothienyl group, or a substituted or unsubstituted carbazolyl group; The substituents in L, L1 and L2 are the same or different and are each independently selected from deuterium, fluorine, cyano, trimethylsilyl, trideuterated methyl, trifluoromethyl, methyl, ethyl, isopropyl, tert-butyl or phenyl; Ar1 and Ar2 are the same or different and are each independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothienyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted spirobifluorenyl; The substituents in Ar1 and Ar2 are the same or different and are each independently selected from deuterium, fluorine, cyano, trimethylsilyl, trifluoromethyl, methyl, ethyl, isopropyl, tert-butyl or phenyl; Provided that it does not contain the following compounds:

2. The organic compound according to claim 1, which has a structure as shown in the following formula I-1 to formula I-3: X, L, L1, L2, Ar1, Ar2, R1, R2, R3, m, n1, n2, and n3 are defined the same as in Formula I.

3. The organic compound according to claim 1 or 2, wherein R1, R2 and R3 are each independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl.

4. The organic compound according to claim 1 or 2, wherein L1 and L2 are each independently selected from a single bond or the group consisting of:

5. The organic compound according to claim 1 or 2, and Each is independently selected from the group consisting of:

6. The organic compound according to claim 1 or 2, which is selected from the group consisting of the following compounds:

7. 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 comprises the organic compound according to any one of claims 1 to 6.

8. The organic electroluminescent device according to claim 7, wherein: The functional layer includes a hole transport layer, and the hole transport layer includes the organic compound.

9. An electronic device comprising the organic electroluminescent device according to claim 7 or 8.

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