Organic compound, electronic component and electronic device containing the same

Abstract

The present application relates to the technical field of organic electroluminescent materials, and provides an organic compound and an electronic component and an electronic device containing the organic compound. The organic compound of the present application contains a double spirocyclic structure, and when the compound is used as a main material of an organic electroluminescent device, the efficiency and life of the device can be significantly improved.

Description

Technical Field

[0001] The present application belongs to the technical field of organic materials, and in particular, relates to an organic compound and an electronic component and an electronic device containing the organic compound. Background Art

[0002] At present, the research on organic electroluminescent materials has been widely carried out in academia and industry, and a large number of organic electroluminescent materials with excellent performance have been developed one after another. In general, the future direction of organic electroluminescent devices is to develop high-efficiency, long-life, low-cost white light devices and full-color display devices, but the industrialization process of this technology still faces many key problems. Therefore, designing and finding a stable and efficient compound as a new material for organic electroluminescent devices to overcome its shortcomings in practical applications is the focus of research on organic electroluminescent device materials and the future research and development trend. With the development of electronic technology and the progress of materials science, the application range of electronic components used to achieve electroluminescence or photoelectric conversion is becoming more and more extensive. 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 are combined with the electrons generated by the cathode through the hole transport layer to form excitons in the light-emitting layer, and then emit light. Organic electroluminescent devices can adjust the emission of various required light by changing the material of the light-emitting layer as needed.

[0003] At present, during the use of the material of the light-emitting layer, the material is easily crystallized due to repeated charging and discharging, and the uniformity of the film is destroyed, thus affecting the service life of the material. Therefore, it is necessary to develop stable and efficient organic materials to reduce the driving voltage, improve the luminous efficiency of the device, and extend the life of the device, so as to further improve the performance of organic electroluminescent devices. Summary of the invention

[0004] In view of the above problems existing in the prior art, the purpose of the present application is to provide an organic compound and an electronic component and an electronic device containing the organic compound, wherein the organic compound can be used in the electronic component to improve the performance of the electronic component.

[0005] The first aspect of the present application provides an organic compound having a structure shown in Formula 1:

[0006]

[0007] wherein n and m are the same or different and are each independently selected from 1, 2 or 3;

[0008] R1, R2, R3 and R4 are the same or different and are each independently selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 10 carbon atoms or an aryl group having 6 to 12 carbon atoms;

[0009] A, B, C and D are the same or different and are independently selected from hydrogen or a group shown in Formula 2, and at least one of A, B, C and D is a group shown in Formula 2;

[0010] n1 represents the number of R1, and is selected from 0, 1, 2, 3 or 4; when n1 is greater than 1, any two R1 are the same or different;

[0011] n2 represents the number of R2 and is selected from 0, 1, 2, 3 or 4; when n2 is greater than 1, any two R2 are the same or different;

[0012] n3 represents the number of R3, and is selected from 0, 1, 2, 3 or 4; when n3 is greater than 1, any two R3 are the same or different;

[0013] n4 represents the number of R4, and is selected from 0, 1, 2, 3 or 4; when n4 is greater than 1, any two R4 are the same or different;

[0014] Ar1 and Ar2 are the same or different and are independently selected from hydrogen, 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;

[0015] 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;

[0016] The substituents in Ar1, Ar2, L, L1 and L2 are the same or different and are independently selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 10 carbon atoms, a trialkylsilyl group having 3 to 12 carbon atoms, a deuterated aryl group having 6 to 12 carbon atoms, an aryl group having 6 to 20 carbon atoms or a heteroaryl group having 3 to 20 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.

[0017] A second aspect of the present application provides an electronic component, 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 above-mentioned organic compound.

[0018] A third aspect of the present application provides an electronic device, comprising the electronic component described in the second aspect.

[0019] The cycloalkyl group and the two fluorenes in the organic compound of the present application form a multi-spiro ring structure, which is connected to the electron-deficient heteroaryl group. Among them, the two fluorene planes can effectively improve the carrier mobility of the compound. At the same time, the multi-spiro ring structure can reduce the stacking between molecules and improve the film forming property of the material. When the compound of the present application is used as an electron transport material in a hybrid host material, on the one hand, it can improve the carrier balance in the light-emitting layer and improve the luminous efficiency; on the other hand, it can promote the formation of an amorphous film and increase the life of the device. BRIEF DESCRIPTION OF THE DRAWINGS

[0020] 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.

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

[0022] Figure 2 is a schematic diagram of an electronic device according to an embodiment of the present application.

[0023] Reference numerals

[0024] 100, anode; 200, cathode; 300, functional layer; 310, hole injection layer; 320, hole transport layer; 321, first hole transport layer; 322, second hole transport layer; 330, organic light emitting layer; 340, electron transport layer; 350, electron injection layer; 360, photoelectric conversion layer; 400, electronic device; DETAILED DESCRIPTION

[0025] 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 being 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 will be 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.

[0026] In a first aspect, the present application provides an organic compound having a structure shown in Formula 1:

[0027]

[0028] wherein n and m are the same or different and are each independently selected from 1, 2 or 3;

[0029] R1, R2, R3 and R4 are the same or different and are each independently selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 10 carbon atoms or an aryl group having 6 to 12 carbon atoms;

[0030] A, B, C and D are the same or different and are independently selected from hydrogen or a group shown in Formula 2, and at least one of A, B, C and D is a group shown in Formula 2;

[0031] n1 represents the number of R1, and is selected from 0, 1, 2, 3 or 4; when n1 is greater than 1, any two R1 are the same or different;

[0032] n2 represents the number of R2 and is selected from 0, 1, 2, 3 or 4; when n2 is greater than 1, any two R2 are the same or different;

[0033] n3 represents the number of R3, and is selected from 0, 1, 2, 3 or 4; when n3 is greater than 1, any two R3 are the same or different;

[0034] n4 represents the number of R4, and is selected from 0, 1, 2, 3 or 4; when n4 is greater than 1, any two R4 are the same or different;

[0035] Ar1 and Ar2 are the same or different and are independently selected from hydrogen, 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;

[0036] 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;

[0037] The substituents in Ar1, Ar2, L, L1 and L2 are the same or different and are independently selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 10 carbon atoms, a trialkylsilyl group having 3 to 12 carbon atoms, a deuterated aryl group having 6 to 12 carbon atoms, an aryl group having 6 to 20 carbon atoms or a heteroaryl group having 3 to 20 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.

[0038] 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.

[0039] 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.

[0040] 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.

[0041] In the present application, "plurality" means more than 2, for example, 2, 3, 4, 5, 6, etc.

[0042] In the present application, the number of carbon atoms in a substituted or unsubstituted functional group refers to the number of all carbon atoms.

[0043] 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).

[0044] The "D" in the structural formula of the compound of the present application represents deuteration.

[0045] 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.

[0046] In the present application, "arylene group" refers to a divalent group formed by further losing one or more hydrogen atoms from an aryl group.

[0047] In the present application, terphenyl includes

[0048] 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.

[0049] 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.

[0050] 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.

[0051] 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.

[0052] 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.

[0053] 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.

[0054] 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.

[0055] 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.

[0056] 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.

[0057] In the present application, the halogen group may be, for example, fluorine, chlorine, bromine, or iodine.

[0058] In the present application, specific examples of trialkylsilyl include, but are not limited to, trimethylsilyl, triethylsilyl, and the like.

[0059] In the present application, specific examples of deuterated aryl groups include, but are not limited to, deuterated phenyl groups.

[0060] 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.

[0061] In this application, Refers to the chemical bonds that connect to other groups.

[0062] 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).

[0063]

[0064] 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).

[0065]

[0066] 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).

[0067]

[0068] In some embodiments of the present application, A, B, C and D are the same or different, and are independently selected from hydrogen or a group shown in Formula 2, and only one or two of A, B, C, and D are groups shown in Formula 2, and the rest are hydrogen.

[0069] Optionally, Formula 1 is selected from the structures shown in the following Formulas I-1 to I-3:

[0070]

[0071] Optionally, the organic compound described in the present application is selected from the structures shown in the following formulas Ia to Ii:

[0072]

[0073] In some embodiments of the present application, R1, R2, R3 and R4 are each independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl or phenyl.

[0074] In some embodiments of the present application, Ar1 and Ar2 are the same or different and 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 12 to 18 carbon atoms.

[0075] Optionally, the substituents in Ar1 and Ar2 are each independently selected from deuterium, fluorine, cyano, an alkyl group having 1 to 5 carbon atoms, a trimethylsilyl group, a deuterated phenyl group, an aryl group having 6 to 12 carbon atoms, or a heteroaryl group having 12 to 18 carbon atoms; optionally, any two adjacent substituents in Ar1 form a saturated or unsaturated 5 to 15-membered ring; optionally, any two adjacent substituents in Ar2 form a saturated or unsaturated 5 to 15-membered ring.

[0076] In some embodiments of the present application, Ar1 and Ar2 are the same or different and are each independently selected from a substituted or unsubstituted group W, wherein the unsubstituted group W is selected from the following groups:

[0077]

[0078] The substituted group W has one or more substituents, each of which is independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trimethylsilyl, deuterated phenyl, phenyl, naphthyl, biphenyl, dibenzofuranyl or dibenzothiophenyl.

[0079] In some embodiments of the present application, Ar1 and Ar2 are the same or different and are each independently selected from the group consisting of the following groups:

[0080]

[0081] Further optionally, Ar1 and Ar2 are the same or different and are each independently selected from the following groups:

[0082]

[0083] 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 12 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 or 12 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.

[0084] Optionally, the substituents in L, L1 and L2 are each independently selected from deuterium, fluorine, cyano, an alkyl group having 1 to 5 carbon atoms, a trimethylsilyl group, a deuterated phenyl group, an aryl group having 6 to 10 carbon atoms or a heteroaryl group having 5 to 12 carbon atoms.

[0085] 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 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.

[0086] Optionally, the substituents in L, L1 and L2 are each independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trimethylsilyl, deuterated phenyl, phenyl or naphthyl.

[0087] In some embodiments, L, L1 and L2 are the same or different and are each independently selected from a single bond or the group consisting of the following groups:

[0088]

[0089] In some embodiments, L, L1 and L2 are selected from the group consisting of a single bond or the following groups:

[0090]

[0091]

[0092] In some embodiments, and Each is independently selected from the group consisting of:

[0093]

[0094] Optionally, the organic compound is selected from the group consisting of the following compounds:

[0095]

[0096]

[0097]

[0098]

[0099]

[0100]

[0101]

[0102]

[0103]

[0104] In a second aspect, the present application provides an electronic component, 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 organic compound of the present application.

[0105] Optionally, the functional layer includes an organic light-emitting layer, and the organic light-emitting layer includes the organic compound described in the present application.

[0106] Optionally, the electronic component is an organic electroluminescent device.

[0107] In one embodiment of the present application, the structure of the organic electroluminescent device is as follows: Figure 1 As shown, it includes an anode 100 and a cathode 200 arranged opposite to each other, and a functional layer 300 arranged between the anode 100 and the cathode 200; the functional layer 300 includes an organic light-emitting layer 330, and the organic light-emitting layer 330 contains the organic compound described in the present application.

[0108] Optionally, the functional layer 300 includes a hole transport layer 320, which is located between the anode and the organic light-emitting layer. Optionally, the hole transport layer 320 includes a first hole transport layer 321 and a second hole transport layer 322 which are stacked, and the first hole transport layer 321 is closer to the anode than the second hole transport layer 322.

[0109] Optionally, the hole transport material can be selected from triarylamine compounds or other types of compounds, and those skilled in the art can select them with reference to the prior art. For example, the material of the hole transport layer is selected from the group consisting of the following compounds.

[0110]

[0111] In one embodiment of the present application, the material of the first hole transport layer 321 includes HT-1.

[0112] In one embodiment of the present application, the material of the second hole transport layer 322 includes HT-2.

[0113] In one embodiment of the present application, the material of the second hole transport layer 322 includes HT-3.

[0114] 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 (indiumtin oxide) (ITO) as an anode is included.

[0115] 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;

[0116]

[0117] In one embodiment of the present application, the material of the hole injection layer 310 includes PD-2.

[0118] 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.

[0119] 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.

[0120] In one embodiment of the present application, the main material of the organic light-emitting layer 330 is an organic compound described in the present application and

[0121] combination.

[0122] In one embodiment of the present application, the main material of the organic light-emitting layer 330 is an organic compound described in the present application and

[0123] combination.

[0124] The guest material of the organic light-emitting layer 330 may 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 thereon. The guest material is also called a doping material or a dopant.

[0125] In some specific embodiments of the present application, the guest material of the organic light-emitting layer 330 is

[0126] In some specific embodiments of the present application, the guest material of the organic light-emitting layer 330 is

[0127] 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.

[0128] Optionally, the electron transport layer 340 can be a single-layer structure or a multi-layer structure, which can include one or more electron transport materials, and the electron transport material can generally include a metal complex or / and a nitrogen-containing heterocyclic derivative, wherein the metal complex material can be selected from LiQ, Alq3, Bepq2, etc.; the nitrogen-containing heterocyclic derivative can be an aromatic ring having a nitrogen-containing six-membered ring or five-membered ring skeleton, a condensed aromatic ring compound having a nitrogen-containing six-membered ring or five-membered ring skeleton, etc. Specific examples include but are not limited to 1,10-phenanthroline compounds such as Bphen, NBphen, DBimiBphen, BimiBphen, or nitrogen-containing aromatic compounds as shown below. In one embodiment of the present application, the electron transport layer 340 is composed of ET-10 and LiQ.

[0129] 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 Yb.

[0130] 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.

[0131] 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.

[0132] 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.

[0133] Synthesis example

[0134] 1. Synthesis of intermediates

[0135] Synthesis of intermediate Sub-A1

[0136]

[0137] (1) Under nitrogen atmosphere, 2-chlorofluorene (100.0 g, 498.33 mmol), methyl acrylate (94.4 g, 1.10 mol), sodium hydroxide (aq., 50%, 996.66 mmol) were added to a three-necked flask, and toluene (1 L) was added to dissolve the system, and the mixture was stirred and heated to reflux for 3 h. After monitoring the completion of the reaction, the heating was stopped. After cooling to room temperature, the reaction solution was washed with water until neutral, filtered, dried, and the solvent was removed by distillation under reduced pressure. The crude product was purified by recrystallization with ethyl acetate / petroleum ether to obtain a white solid, which was the product Sub-a1 (149.0 g, yield 80.2%).

[0138]

[0139] (2) Under nitrogen atmosphere, Sub-a1 (149.0 g, 399.62 mmol), sodium methoxide (32.4 g, 502.90 mmol), and toluene (1500 mL) were added to a reaction flask, and the mixture was stirred and heated to reflux for 12 h. The reaction was monitored for completion. After cooling to room temperature, the reaction solution was washed with water until neutral, filtered, dried, and distilled under reduced pressure to remove toluene. The crude product was recrystallized from ethyl acetate / petroleum ether to obtain a white solid, which was the product Sub-a2 (95.7 g, yield 70.8%).

[0140]

[0141] (3) Sub-a2 (95.0 g, 278.75 mmol) and glacial acetic acid (950 mL) were added to the reaction flask. After stirring, 12 M concentrated hydrochloric acid (28.3 mL, 339.27 mmol) was slowly added to the reaction flask using a constant pressure dropping funnel. After the addition was completed, the temperature was slowly raised to reflux and stirred for 8 h. The reaction solution was cooled to room temperature and added to 1 L of water. A white solid was precipitated. The solution was filtered and washed with high-purity water until neutral. The crude product was purified by silica gel chromatography to obtain a white solid, which was the product Sub-a3 (37.4 g, yield 47.5%).

[0142]

[0143] (4) Sub-a3 (37.0 g, 130.85 mmol), catechol (18.7 g, 170.10 mmol) and toluene (600 mL) were added to a three-necked flask, heated and stirred until the raw materials were dissolved, and water was removed by a water separator, and then concentrated sulfuric acid (98%, 1.4 g, 13.85 mmol) was slowly added dropwise. Then, stirring and refluxing were continued to remove water until no Sub-a3 remained when monitored by TLC. The reaction was completed. After the reaction solution was cooled to room temperature, it was washed with water until neutral, extracted, separated, and the organic phase was concentrated. The crude product was recrystallized with diethyl ether. The obtained product was the intermediate Sub-a4 (36.4 g, yield 74.2%).

[0144]

[0145] (5) Under nitrogen protection, the intermediate Sub-a4 (36.4 g, 97.10 mmol) was dissolved in dichloromethane (500 mL), stirred and cooled to 0°C in an ice bath, and boron tribromide (36.5 g, 145.65 mmol) was slowly added to the reaction system using a constant pressure dropping funnel, and the reaction was kept warm for 8 h. The reaction was slowly restored to room temperature, and then NaOH (7.8 g, 170.73 mmol), tetrabutylammonium hydrogen sulfate (n-Bu4NHSO4, 6.6 g, 19.42 mmol), and deionized water (10 mL) were added, and the reaction was continued at room temperature for 72 h. 500 mL of water was added to quench the reaction, and the organic phase was washed with water and extracted after separation. The organic phase was concentrated to obtain a solid crude product. After recrystallization and purification using dichloromethane / n-heptane, the intermediate Sub-a5 (28.4 g, yield: 84.6%) was obtained.

[0146]

[0147] (6) Under nitrogen atmosphere, add intermediate Sub-a5 (28.4 g, 82.16 mmol), 2-biphenylboronic acid (17.1 g, 86.27 mmol), potassium carbonate (25.0 g, 180.75 mmol) to a three-necked flask, dissolve in toluene (280 mL), ethanol (120 mL) and water (60 mL), heat to 60°C, quickly add tetrakis(triphenylphosphine)palladium (1.9 g, 1.65 mmol) and tetrabutylammonium bromide TBAB (2.7 g, 8.2 mmol), continue to heat to 75°C and react for 20 h. After the reaction is completed, cool to room temperature. The reaction solution is extracted with dichloromethane, and the organic phase is concentrated. The crude product is purified by column chromatography using a mixed solvent of dichloromethane and n-heptane to obtain the target product Sub-a6 (34.4 g, yield 88.3%) as a white solid.

[0148]

[0149] (7) Under nitrogen atmosphere, add Sub-a6 (34.4 g, 82.10 mmol) to a three-necked flask and dissolve it in dichloromethane (350 mL). Cool the reaction system to 0°C, slowly add methanesulfonic acid (1.6 g, 17.10 mmol) dropwise with sufficient stirring, and keep stirring for 2 h. Then cool the reaction solution to -10°C and add 150 mL of ice water to quench the reaction, then slowly warm it to room temperature. Extract with dichloromethane and wash with water, and concentrate the organic phase. Purify with dichloromethane and n-heptane, and then recrystallize with ethyl acetate / n-heptane until HPLC>98%. Dry to obtain a white solid Sub-A1 (32.7 g, yield 95.1%).

[0150] Synthesis of intermediates Sub-A2 to Sub-A8:

[0151] Intermediates Sub-A2 to Sub-A8 were synthesized by the same method as intermediate Sub-A1, except that raw material 1 in Table 1 was used to replace 2-chlorofluorene in step (1), and raw material 2 was used to replace 2-biphenylboronic acid in step (6). Other conditions remained unchanged. The structures and yields of the raw materials used, intermediates in each step, and products are shown in Table 1.

[0152] Table 1

[0153]

[0154]

[0155] Synthesis of intermediate Sub-B1

[0156]

[0157] (1) The intermediate Sub-b2 was synthesized by the same preparation method as the intermediate Sub-a4, except that Sub-b1 (Cas.113163-16-9, commercially available) was used to replace the intermediate Sub-a3, and other conditions remained unchanged to obtain the intermediate Sub-b2 (32 g, yield 71.5%).

[0158]

[0159] (2) The intermediate Sub-b3 was synthesized by the same preparation method as the intermediate Sub-a5, except that Sub-b2 was used to replace the intermediate Sub-a4. Other conditions remained unchanged to obtain the intermediate Sub-b3 (22.3 g, yield 79.6%).

[0160]

[0161] (3) Intermediate Sub-b4 was synthesized by the same preparation method as intermediate Sub-a6, except that Sub-b3 was used to replace intermediate Sub-a5, and 4-chloro-2'-biphenylboronic acid was used to replace 2-biphenylboronic acid; other conditions remained unchanged, and intermediate Sub-b4 (24.1 g, yield 80.2%) was obtained.

[0162]

[0163] (4) The intermediate Sub-B1 was synthesized by the same preparation method as the intermediate Sub-A1, except that Sub-b4 was used to replace the intermediate Sub-a6. Other conditions remained unchanged to obtain the intermediate Sub-B1 (21.9 g, yield 91.2%).

[0164] Synthesis of intermediates Sub-B2 to Sub-B4:

[0165] Intermediates Sub-B2 to Sub-B4 were synthesized by the same method as intermediate Sub-B1, except that raw material 3 in Table 2 was used instead of 4-chloro-2'-biphenylborane. Other conditions remained unchanged. The structures and yields of the raw materials, intermediates in each step, and products are shown in Table 2.

[0166] Table 2

[0167]

[0168]

[0169] Synthesis of intermediates Sub-C1 and Sub-C2:

[0170]

[0171] (1) Under nitrogen atmosphere, 9-(trimethylsilyl)fluorene (50.0 g, 209.72 mmol) was dissolved in dry THF (500 mL) in a three-necked reaction flask. The reaction system was cooled to -78°C with liquid nitrogen, and a 2M n-butyllithium n-hexane solution (113 mL, 224.73 mmol) was slowly added dropwise. After the addition was completed, the mixture was kept warm and stirred for 2 h. Then, 250 mL of a THF solution containing 1,2-bis(tolyloxy)ethane (42.5 g, 114.72 mmol) was slowly added dropwise. After the addition was completed, the mixture was kept warm for 1 h and then naturally heated to room temperature. After the reaction was completed, the reaction was quenched with deionized water, the pH of the reaction solution was adjusted to 6.0 with dilute hydrochloric acid, and the reaction solution was extracted with dichloromethane and water to concentrate the organic phase. The crude product was purified by recrystallization from dichloromethane / n-heptane to obtain the intermediate Sub-c1 (59.9 g, yield 56.8%).

[0172] (2) Under nitrogen protection, in a three-necked reaction flask, the intermediate Sub-c1 (59.9 g, 119.12 mmol) and tetrabutylammonium fluoride (6.2 g, 23.82 mmol) were dissolved in dichloromethane (500 mL) and stirred at room temperature for 2 days. After the reaction was completed, the organic phase was extracted and concentrated. The obtained crude oil was separated and purified by silica gel column using dichloromethane / n-heptane as eluent to obtain the intermediate Sub-c2 (10.8 g, yield 24.5%).

[0173] (3) Under nitrogen atmosphere, the intermediate Sub-c2 (10.8 g, 29.15 mmol) was dissolved in carbon tetrachloride (120 mL) in a three-necked reaction flask. After the raw material was dissolved, azobisisobutyronitrile (AIBN, 0.09 g, 0.58 mmol) and N-bromosuccinimide (7.8 g, 43.73 mmol) were added, stirred and heated to reflux. The reaction was stopped after 12 h. After naturally cooling to room temperature, deionized water was added to quench the reaction. After separation, the organic phase was extracted and washed with water. The organic phase was collected and concentrated by rotary evaporation. The crude product was separated and purified by passing through a silica gel column with dichloromethane / n-heptane to obtain monobrominated product Sub-C1 (7.9 g, yield 60.5%) and dibrominated product Sub-C2 (2.9 g, yield 18.9%).

[0174] 2. Synthesis of compounds

[0175]

[0176] (1) Under nitrogen protection, the intermediate Sub-A1 (10.0 g, 23.87 mmol), bipyralidin (8.5 g, 33.42 mmol) and potassium acetate (4.7 g, 47.74 mmol) were dissolved in 1,4-dioxane (100 mL), stirred and heated to 50°C, tri(dibenzylideneacetone)dipalladium (0.44 g, 0.48 mmol) and 2-dicyclohexylphosphine-2',4',6'-triisopropylbiphenyl (0.46 g, 0.95 mmol) were added, and heated to 80°C and stirred for 8 h. After the reaction was completed, the reaction solution was cooled to room temperature, extracted with dichloromethane and washed with water, and the organic phases were combined, concentrated and the solvent was removed. The crude product was purified by recrystallization using dichloromethane / n-heptane to obtain a gray solid Sub-A1-B (6.7 g, yield 55.3%).

[0177]

[0178] (2) Under nitrogen protection, in a 250 ml three-necked flask, the intermediate Sub-A1-B (6.7 g, 13.47 mmol), the raw material Ra (3.3 g, 12.25 mmol), potassium carbonate (4.3 g, 30.98 mmol) and tetrabutylammonium bromide TBAB (0.8 g, 2.69 mmol) were dissolved in toluene: ethanol: water (80 mL: 40 mL: 20 mL), and the temperature was raised to 50°C. Tetrakis(triphenylphosphine)palladium (0.3 g, 0.27 mmol) was quickly added, and the temperature was raised to reflux for 20 h. After the reaction was completed, it was cooled to room temperature, extracted with dichloromethane, washed with water, dried with anhydrous magnesium sulfate, filtered, and concentrated. The crude product was purified by recrystallization using toluene / n-heptane to obtain the product A01 (4.1 g, yield 49.5%) (m / z = 616.27 [M+H] + ).

[0179] The compounds in Table 4 were prepared by the same method as compound A01, except that intermediate Sub-Xx in Table 3 was used to replace intermediate Sub-A1 to prepare intermediate Sub-Ax-B, and raw material Ra was replaced by raw material 4, while other conditions remained unchanged; the structures, yields and mass spectrometry characterization results of the materials and products used are listed in Table 3.

[0180] Table 3

[0181]

[0182]

[0183]

[0184]

[0185]

[0186]

[0187] Synthesis of Compound A122

[0188]

[0189] (1) Under nitrogen protection, the intermediate Sub-A1 (15.0 g, 35.10 mmol), diboronic acid pinacol ester (22.3 g, 87.72 mmol) and potassium acetate (7.0 g, 70.17 mmol) were dissolved in 1,4-dioxane (150 mL), stirred and heated to 50°C, tri(dibenzylideneacetone)dipalladium (0.65 g, 0.70 mmol) and 2-dicyclohexylphosphine-2',4',6'-triisopropylbiphenyl (0.67 g, 1.40 mmol) were added, and heated to 80°C and stirred for 8 h; after the reaction was completed, the reaction solution was cooled to room temperature, extracted with dichloromethane and washed with water, and the organic phases were combined, concentrated and the solvent was removed; the crude product was purified by recrystallization using dichloromethane / n-heptane to obtain a gray solid Sub-A1-2B (11.96 g, yield 53.8%).

[0190]

[0191] (2) Under nitrogen protection, in a 250 ml three-necked flask, the intermediate Sub-A1-2B (11.9 g, 19.17 mmol), the raw material Ra (10.6 g, 39.45 mmol), potassium carbonate (5.2 g, 37.57 mmol) and tetrabutylammonium bromide TBAB (1.2 g, 3.75 mmol) were dissolved in toluene: ethanol: water (120 mL: 60 mL: 30 mL), and the temperature was raised to 50 ° C. After that, tetrakis(triphenylphosphine)palladium (0.4 g, 0.37 mmol) was quickly added, and the temperature was raised to reflux for 20 h. After the reaction was completed, it was cooled to room temperature, extracted with dichloromethane, washed with water, dried with anhydrous magnesium sulfate, filtered, and concentrated. The crude product was purified by recrystallization using toluene / n-heptane to obtain the product A122 (7.6 g, 48.5%) (m / z=847.35 [M+H] + ).

[0192] The compounds in Table 4 were prepared by the same method as compound A122, except that intermediate Sub-Xx in Table 4 was used to replace intermediate Sub-A4 to prepare intermediate Sub-Ax-2B, and raw material Ra was replaced by raw material 5, while other conditions remained unchanged; the structures, yields and mass spectrometry characterization results of the materials and products used are listed in Table 4.

[0193] Table 4

[0194]

[0195] The NMR data of the compound are shown in Table 5:

[0196] Table 5

[0197]

[0198] Example 1 Green organic electroluminescent device

[0199] The anode was prepared by the following process: On the ITO / Ag / ITO substrate, the surface is treated with UV ozone and O2:N2 plasma to increase the work function of the anode. The surface of the ITO substrate can also be cleaned with an organic solvent to remove impurities and oil stains on the surface of the ITO substrate.

[0200] On the experimental substrate (anode), PD-2:HT-1 was co-evaporated at an evaporation rate ratio of 2%:98% to form a film with a thickness of A hole injection layer (HIL) is formed by evaporating HT-1 on the hole injection layer to form a thickness of The first hole transport layer is formed by a plurality of holes.

[0201] HT-2 is vacuum evaporated on the first hole transport layer to form a layer with a thickness of The second hole transport layer is

[0202] On the second hole transport layer, compound A01:GH-P:GD was co-evaporated at an evaporation rate ratio of 4:6:1 to form a layer with a thickness of Green emitting layer (EML).

[0203] ET and LiQ were mixed in a weight ratio of 1:1 and evaporated to form A thick electron transport layer (ETL) is formed by evaporating Yb on the electron transport layer to form a layer with a thickness of Then, magnesium (Mg) and silver (Ag) were mixed at a deposition rate ratio of 1:9 and vacuum-deposited on the electron injection layer to form a layer with a thickness of cathode.

[0204] In addition, a layer with a thickness of A CP is formed to form an organic cover layer (CPL), thereby completing the manufacture of the organic light-emitting device.

[0205] Device Examples 2 to 24

[0206] Organic electroluminescent devices were prepared in the same manner as in Example 1, except that the compounds shown in Table 6 were used instead of Compound A01 when forming the light-emitting layer. The prepared devices are recorded as Examples 2 to 24.

[0207] Comparative Examples 1-2

[0208] An organic electroluminescent device was prepared by the same method as in Example 1, except that compound A01 in Example 1 was replaced by compound A and compound B respectively when preparing the light-emitting layer.

[0209] The green organic electroluminescent devices prepared in Examples 1 to 24 and Comparative Examples 1 to 2 were tested for performance. Specifically, at 10 mA / cm 2 The IVL performance of the device was tested under the conditions of T 95 Device life at 20mA / cm 2 The test was carried out under the conditions of , and the test results are shown in Table 6.

[0210] Table 6

[0211]

[0212]

[0213] Example 24: Red organic electroluminescent device

[0214] First, the anode pretreatment is carried out through the following process: the thickness is On the ITO / Ag / ITO substrate, the surface is treated with UV ozone and O2:N2 plasma to increase the work function of the anode. The surface of the ITO substrate can also be cleaned with an organic solvent to remove impurities and oil stains on the surface of the ITO substrate.

[0215] On the experimental substrate (anode), PD-2:HT-1 was co-evaporated at an evaporation rate ratio of 2%:98% to form a film with a thickness of Then, HT-1 was vacuum-deposited on the hole injection layer to form a hole injection layer with a thickness of The compound HT-3 is vacuum-deposited on the first hole transport layer to form a hole transport layer with a thickness of The second hole transport layer

[0216] Next, on the second hole transport layer, compound A16:RH-P:RD was co-evaporated at a ratio of 49%:49%:2% to form a layer with a thickness of Red light emitting layer (EML)

[0217] On the light-emitting layer, compound ET and LiQ are co-evaporated at an evaporation rate ratio of 1:1 to form A thick electron transport layer (ETL) is formed by evaporating Yb on the electron transport layer to form a layer with a thickness of Then, magnesium (Mg) and silver (Ag) were mixed at a evaporation rate of 1:9 and vacuum evaporated on the electron injection layer to form a layer with a thickness of cathode.

[0218] In addition, the thickness of the vacuum evaporation layer on the cathode is CP, thereby completing the manufacture of the red organic electroluminescent device.

[0219] Embodiments 25 to 35

[0220] An organic electroluminescent device was prepared by the same method as in Example 24, except that the compounds in the following Table 7 were used instead of Compound A16 in Example 24 when preparing the light-emitting layer.

[0221] Comparative Examples 1 to 3

[0222] An organic electroluminescent device was prepared by the same method as in Example 24, except that Compound C and Compound D were used to replace Compound A16 in Example 24 when preparing the light-emitting layer.

[0223] The performance of the red organic electroluminescent devices prepared in Examples 24-35 and Comparative Examples 3-4 was tested. Specifically, at 10 mA / cm 2 The IVL performance of the device was tested under the conditions of T95 Device life at 20mA / cm 2 The test was carried out under the conditions of , and the test results are shown in Table 7.

[0224] Table 7

[0225]

[0226]

[0227] Wherein, when preparing each of Examples 1-35 and Comparative Examples 1-4, the compound structures used are as follows:

[0228]

[0229] As shown in Table 6, when the compound of the present invention is used as the main material of the green organic electroluminescent device, the luminous efficiency is at least increased by 13.9%, and the device life is at least increased by 16.4%. As shown in Table 7, when the compound of the present invention is used as the main material of the red organic electroluminescent device, the luminous efficiency is at least increased by 12.4%, and the device life is at least increased by 15.2. It can be seen that the use of the organic compound of the present application as the main material of the organic electroluminescent device can significantly improve the luminous efficiency and device life of the organic electroluminescent device.

[0230] The reason is that the organic compound of the present application contains a multi-spiro ring structure formed by a cycloalkyl group and two fluorenes, and the multi-spiro ring structure is connected to an electron-deficient heteroaryl group. Among them, the two fluorene planes can effectively improve the carrier mobility of the compound. At the same time, the multi-spiro ring structure can reduce the stacking between molecules and improve the film-forming property of the material. When the compound of the present application is used as an electron transport material in a hybrid host material, on the one hand, it can improve the carrier balance in the light-emitting layer and improve the luminous efficiency; on the other hand, it can promote the formation of an amorphous film and increase the life of the device.

[0231] The preferred embodiments of the present application are described in detail above; however, the present application is not limited to the specific details in the above embodiments. Within the technical concept of the present application, a variety of simple modifications can be made to the technical solution of the present application, and these simple modifications all fall within the protection scope of the present application.

Claims

1. An organic compound, characterized in that The organic compound has a structure shown in Formula 1: Wherein, Formula I is selected from the structures shown in the following Formulas I-1 to I-3: R1, R2, R3 and R4 are the same or different and are each independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl; Only one or two of A, B, C, and D are groups represented by formula 2, and the rest are hydrogen atoms; n1 represents the number of R1, and is selected from 0, 1, 2, 3 or 4; when n1 is greater than 1, any two R1 are the same or different; n2 represents the number of R2 and is selected from 0, 1, 2, 3 or 4; when n2 is greater than 1, any two R2 are the same or different; n3 represents the number of R3, and is selected from 0, 1, 2, 3 or 4; when n3 is greater than 1, any two R3 are the same or different; n4 represents the number of R4, and is selected from 0, 1, 2, 3 or 4; when n4 is greater than 1, any two R4 are the same or different; Ar1 and Ar2 are the same or different and are each independently selected from a substituted or unsubstituted group W, wherein the unsubstituted group W is selected from the following groups: Wherein, the substituted group W has one or more substituents, and the substituents are each independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trimethylsilyl, deuterated phenyl or phenyl; 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, or a substituted or unsubstituted biphenylene group; The substituents in L, L1 and L2 are each independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trimethylsilyl, deuterated phenyl or phenyl.

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

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

4. An electronic component comprising an anode and a cathode disposed opposite to each other, and a functional layer disposed between the anode and the cathode; characterized in that: The functional layer contains the organic compound according to any one of claims 1 to 3.

5. The electronic component according to claim 4, wherein: The electronic component is an organic electroluminescent device.

6. The electronic component according to claim 4 or 5, wherein: The functional layer includes an organic light-emitting layer, and the organic light-emitting layer includes the organic compound.

7. An electronic device, characterized in that An electronic component comprising any one of claims 4 to 6.

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