Organic compound, organic electroluminescent device, and electronic device

Abstract

The invention relates to the technical field of organic electroluminescent materials, and provides an organic compound, an organic electroluminescent device containing the same and an electronic device. According to the compound, dibenzo [1, 4] hetero-silane and carbazole serve as a compound core structure, when the compound serves as a main body material of a light-emitting layer, carrier balance in the light-emitting layer can be improved, a carrier recombination area can be widened, the energy transfer efficiency from the main body material to a doping material can be improved, the overall light-emitting efficiency of a device can be improved, and the service life of the device can be prolonged.

Description

Technical Field

[0001] The present application relates to the technical field of organic electroluminescent materials, and in particular to organic compounds and organic electroluminescent devices and electronic devices containing the same. Background Art

[0002] With the development of electronic technology and the progress of materials science, the application scope of electronic components for realizing electroluminescence or photoelectric conversion is becoming more and more extensive. Organic electroluminescent devices (OLEDs) generally include a cathode and an anode arranged relatively to each other, and a functional layer arranged between the cathode and the anode. The functional layer is composed of multiple organic or inorganic film layers, and generally includes an organic light-emitting layer, a hole transport layer, an electron transport layer, etc. When a voltage is applied to the anode and the cathode, the two electrodes generate an electric field. Under the action of the electric field, the electrons on the cathode side move toward the electroluminescent layer, and the holes on the anode side also move toward the light-emitting layer. The electrons and holes combine in the electroluminescent layer to form excitons. The excitons are in an excited state and release energy outward, thereby causing the electroluminescent layer to emit light outward.

[0003] The main problems with existing organic electroluminescent devices are lifespan and efficiency. As displays become larger, the driving voltage also increases, and the luminous efficiency and current efficiency also need to be improved. Therefore, it is necessary to continue to develop new materials to further improve the performance of organic electroluminescent devices. Summary of the Invention

[0004] In view of the above problems existing in the prior art, the purpose of this 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 the organic electroluminescent device to improve the performance of the device.

[0005] According to a first aspect of the present application, an organic compound is provided, wherein the organic compound has a structure shown in the following formula 1:

[0006]

[0007] wherein X is selected from O or S;

[0008] Ar1 is selected from a substituted or unsubstituted aryl group having 6 to 40 carbon atoms, or a substituted or unsubstituted heteroaryl group having 3 to 40 carbon atoms;

[0009] Ar2 is selected from a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 40 carbon atoms, and a substituted or unsubstituted heteroaryl group having 3 to 40 carbon atoms;

[0010] L is selected from substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenylene;

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

[0012] n1, n2 and n3 represent the number of substituents R1, R2 and R3 respectively, n1 and n2 are the same or different and are independently selected from 0, 1, 2, 3 or 4; n3 is selected from 0, 1, 2, 3, 4, 5, 6 or 7;

[0013] The substituents in L, 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, triphenylsilyl group, aryl group having 6 to 20 carbon atoms, deuterated aryl group having 6 to 20 carbon atoms, haloaryl group having 6 to 20 carbon atoms, heteroaryl group having 3 to 20 carbon atoms, and cycloalkyl group having 3 to 10 carbon atoms; optionally, any two adjacent substituents in Ar2 form a ring.

[0014] 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.

[0015] According to a third aspect of the present application, an electronic device is provided, comprising the organic electroluminescent device according to the second aspect.

[0016] The structure of the compound of the present application includes a structure in which a silafluorene nucleus is connected to carbazole via a dibenzo pentacyclic ring. The silafluorene nucleus and the two substituents at position 9 are located on three different planes, resulting in a relatively large molecular twist, which gives the compound a higher glass transition temperature and enables the compound to form a good amorphous film. In particular, when the silafluorene and carbazole are connected by a dibenzo pentacyclic ring, the entire molecule has a higher first excited triplet energy level. When the compound of the present application is used as a hole-transporting material in a hybrid blue-light host material, on the one hand, the compound's higher first excited triplet energy level can improve the energy transfer efficiency from the host material to the blue-light dopant material, thereby improving the luminous efficiency of the device; on the other hand, the compound's higher glass transition temperature can ensure that the light-emitting layer forms a good amorphous film and that the film morphology does not change during the long-term operation of the device, thereby improving the device life. BRIEF DESCRIPTION OF THE DRAWINGS

[0017] 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.

[0018] Figure 1 It is a schematic structural diagram of an organic electroluminescent device according to one embodiment of the present application.

[0019] Figure 2 It is a schematic structural diagram of an electronic device according to one embodiment of the present application.

[0020] Reference numerals

[0021] 100, anode 200, cathode 300, functional layer 310, hole injection layer

[0022] 321, hole transport layer 322, electron blocking layer 330, organic light emitting layer 340, electron transport layer

[0023] 350, electron injection layer 400, electronic device DETAILED DESCRIPTION

[0024] The exemplary embodiments will now be described more fully with reference to the accompanying drawings. However, the 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 this application will be more comprehensive and complete and will fully convey the concepts of the exemplary embodiments to those skilled in the art. The described features, structures, or characteristics may be combined in any suitable manner in one or more embodiments. In the following description, numerous specific details are provided to provide a full understanding of the embodiments of the present application.

[0025] In a first aspect, the present application provides an organic compound having a structure shown in the following formula 1:

[0026]

[0027] wherein X is selected from O or S;

[0028] Ar1 is selected from a substituted or unsubstituted aryl group having 6 to 40 carbon atoms, or a substituted or unsubstituted heteroaryl group having 3 to 40 carbon atoms;

[0029] Ar2 is selected from a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 40 carbon atoms, and a substituted or unsubstituted heteroaryl group having 3 to 40 carbon atoms;

[0030] L is selected from substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenylene;

[0031] Each of R1, R2 and R3 is the same or different and is independently selected from deuterium, cyano, a halogen group, an alkyl group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, a deuterated alkyl group having 1 to 10 carbon atoms, a trialkylsilyl group having 3 to 12 carbon atoms, a triphenylsilyl group, an aryl group having 6 to 20 carbon atoms, a deuterated aryl group having 6 to 20 carbon atoms, a haloaryl group having 6 to 20 carbon atoms, a heteroaryl group having 3 to 20 carbon atoms, and a cycloalkyl group having 3 to 10 carbon atoms;

[0032] n1, n2 and n3 represent the number of substituents R1, R2 and R3 respectively, n1 and n2 are the same or different and are independently selected from 0, 1, 2, 3 or 4; n3 is selected from 0, 1, 2, 3, 4, 5, 6 or 7;

[0033] The substituents in L, 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, triphenylsilyl group, aryl group having 6 to 20 carbon atoms, deuterated aryl group having 6 to 20 carbon atoms, haloaryl group having 6 to 20 carbon atoms, heteroaryl group having 3 to 20 carbon atoms, and cycloalkyl group having 3 to 10 carbon atoms; optionally, any two adjacent substituents in Ar2 form a ring.

[0034] 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 ring" means that the two substituents may or may not form a ring, that is, including: the scenario where two adjacent substituents form a ring and the scenario where two adjacent substituents do not form a ring. For another example, "optionally, any two adjacent substituents in Ar2 form a ring" means that any two adjacent substituents in Ar2 are connected to each other to form a ring, or any two adjacent substituents in Ar2 can also exist independently. "Any two adjacent" can include two substituents on the same atom, and can also include one substituent on each of two adjacent atoms; wherein, when there are two substituents on the same atom, the two substituents can form a saturated or unsaturated spirocycle with the atom to which they are commonly connected; when there is one substituent on each of two adjacent atoms, the two substituents can be fused into a ring.

[0035] In this application, the descriptions used in this application are interchangeable with "each ... independently is" and "... independently is" and "... independently is" 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,

[0036] Wherein, each q is independently 0, 1, 2 or 3, and each R" is independently selected from hydrogen, deuterium, fluorine, and chlorine. The meaning is: Formula Q-1 represents 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 represents 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.

[0037] In this application, the term "substituted or unsubstituted" means that the functional group described after the term may or may not have a substituent (hereinafter, for ease of description, the substituents are collectively referred to as Rc). For example, "substituted or unsubstituted aryl" refers to an aryl group having a substituent Rc or an unsubstituted aryl group. The above-mentioned substituent 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 deuterated alkyl group, a deuterated aryl group, a haloaryl group, a cycloalkyl group, etc. The number of substitutions can be one or more.

[0038] In this application, "plurality" refers to more than two, for example, 2, 3, 4, 5, 6, etc.

[0039] 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).

[0040] In this application, the number of carbon atoms in a substituted or unsubstituted functional group refers to the total number of carbon atoms. For example, if L is a substituted arylene group with 12 carbon atoms, the total number of carbon atoms in the arylene group and its substituents is 12.

[0041] In the present application, aryl refers to an optional functional group or substituent derived from an aromatic carbocyclic ring. Aryl can be a monocyclic aryl (such as phenyl) or a polycyclic aryl. In other words, aryl can be a monocyclic aryl, a condensed ring aryl, two or more monocyclic aryl groups connected by a carbon-carbon single bond, a monocyclic aryl and a condensed ring aryl connected by a carbon-carbon single bond, two or more condensed ring aryl groups connected by a carbon-carbon single bond. That is, unless otherwise indicated, two or more aromatic groups connected by a carbon-carbon single bond can also be considered as aryl of the present application. Wherein, condensed ring aryl, for example, can include dicyclic condensed aryl (such as naphthyl), tricyclic condensed aryl (such as phenanthrenyl, fluorenyl, anthryl) etc. Aryl does not contain heteroatoms such as B, N, O, S, P, Se and Si. Examples of aryl groups may include, but are not limited to, phenyl, naphthyl, fluorenyl, phenyl-naphthyl, spirobifluorenyl, anthracenyl, phenanthrenyl, biphenyl, terphenyl, triphenylene, perylenyl, benzo[9,10]phenanthrenyl, pyrenyl, benzofluoranthenyl, Z group, and the like.

[0042] In the present application, the arylene group refers to a divalent or multivalent group formed by further losing one or more hydrogen atoms from an aryl group.

[0043] In this application, terphenyl includes

[0044] In the present application, the number of carbon atoms of a substituted aryl group refers to the total number of carbon atoms of the aryl group and the substituents on the aryl group. For example, a substituted aryl group with 18 carbon atoms refers to the total number of carbon atoms of the aryl group and the substituents being 18.

[0045] In the present application, the number of carbon atoms 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, 26, 28, 30, 31, 33, 34, 35, 36, 38 or 40, etc. In some embodiments, the substituted or unsubstituted aryl group is a substituted or unsubstituted aryl group having 6 to 40 carbon atoms, in other 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, and in other embodiments, the substituted or unsubstituted aryl group is a substituted or unsubstituted aryl group having 6 to 15 carbon atoms.

[0046] In the present application, the fluorenyl group may be substituted by one or more substituents. In the case where the fluorenyl group is substituted, the substituted fluorenyl group may be: etc., but not limited thereto.

[0047] In the present application, the aryl group as a substituent of L, Ar1 and Ar2 includes, but is not limited to, phenyl, naphthyl, phenanthrenyl, biphenyl, fluorenyl, dimethylfluorenyl and the like.

[0048] In the present application, a heteroaryl group 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 can be one or more of B, O, N, P, Si, Se and S. A heteroaryl group can be a monocyclic heteroaryl group or a polycyclic heteroaryl group. In other words, a heteroaryl group can be a single aromatic ring system or multiple aromatic ring systems connected by carbon-carbon single bonds, and any aromatic ring system is an aromatic monocyclic ring or an aromatic condensed ring. For example, heteroaryl groups may include thienyl, furyl, pyrrolyl, imidazolyl, thiazolyl, oxazolyl, oxadiazolyl, triazolyl, pyridyl, bipyridyl, pyrimidyl, triazinyl, acridinyl, pyridazinyl, pyrazinyl, quinolyl, quinazolinyl, quinoxalinyl, phenoxazinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, isoquinolyl, indolyl, carbazolyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothienyl, dibenzothienyl, thienothiphenyl, benzofuranyl, phenanthrolinyl, isoxazolyl, thiadiazolyl, phenothiazinyl, silafluorenyl, dibenzofuranyl, benzodibenzofuranyl Benzodibenzothiophene The base, etc., but not limited to this.

[0049] 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.

[0050] 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, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39 or 40, etc. In some embodiments, the substituted or unsubstituted heteroaryl is a substituted or unsubstituted heteroaryl having a total carbon number of 3 to 40, in other embodiments, the substituted or unsubstituted heteroaryl is a substituted or unsubstituted heteroaryl having a total carbon number of 3 to 30, and in other embodiments, the substituted or unsubstituted heteroaryl is a substituted or unsubstituted heteroaryl having a total carbon number of 5 to 12.

[0051] In the present application, the heteroaryl groups as substituents for L, Ar1 and Ar2 include, but are not limited to, pyridyl, carbazolyl, quinolyl, isoquinolyl, phenanthroline, benzoxazolyl, benzothiazolyl, benzimidazolyl, dibenzothiophenyl and dibenzofuranyl.

[0052] In the present application, a 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, etc. It should be understood that the number of carbon atoms in the substituted heteroaryl group refers to the total number of carbon atoms in the heteroaryl group and the substituents on the heteroaryl group.

[0053] 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 of the alkyl group is, for example, 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10. 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, and n-hexyl.

[0054] In the present application, the halogen group is, for example, fluorine, chlorine, bromine, or iodine.

[0055] In the present application, specific examples of trialkylsilyl include, but are not limited to, trimethylsilyl, triethylsilyl, and the like.

[0056] In the present application, specific examples of the haloalkyl group include, but are not limited to, trifluoromethyl.

[0057] In the present application, specific examples of deuterated alkyl groups include, but are not limited to, trideuterated methyl groups.

[0058] In the present application, a deuterated aryl group refers to an aryl group containing deuterium substitution, such as but not limited to deuterated phenyl, deuterated naphthyl, deuterated biphenyl, and the like.

[0059] In the present application, a halogenated aryl group refers to an aryl group with a halogen substituent, such as but not limited to fluorophenyl, fluoronaphthyl, fluorobiphenyl, and the like.

[0060] In the present application, the number of carbon atoms in the cycloalkyl group having 3 to 10 is, 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.

[0061] In this application, no single bond extending from the ring system is involved in the positioning of the connecting bond. This means that one end of the link can be connected to any position in the ring system that the link 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 via two non-positional linkers that pass through the bicyclic ring. The meaning of this includes any possible connection method shown in formulas (f-1) to (f-10):

[0062]

[0063] For example, as shown in the following formula (X'), the dibenzofuranyl group represented by formula (X') is connected to other positions of the molecule through a non-positional connecting bond extending from the middle of one benzene ring. The meaning represented by it includes any possible connection method shown in formulas (X'-1) to (X'-4):

[0064]

[0065] A non-positional substituent herein refers to a substituent connected via a single bond extending from the center of the ring system, indicating that the substituent can be attached at any possible position within 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 via a non-positional bond, and its meaning includes any possible connection method shown in formulas (Y-1) to (Y-7):

[0066]

[0067] In some embodiments, the organic compound is selected from the structures shown in the following formula (1-1), (1-2) or (1-3):

[0068]

[0069] In some embodiments, Ar1 is selected from a substituted or unsubstituted aryl group having 6 to 25 carbon atoms and a substituted or unsubstituted heteroaryl group having 12 to 18 carbon atoms.

[0070] In some embodiments, Ar1 is selected from substituted or unsubstituted aryl having 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24 or 25 carbon atoms, and substituted or unsubstituted heteroaryl having 12, 13, 14, 15, 16, 17 or 18 carbon atoms.

[0071] In some embodiments, the substituents in Ar1 are each independently selected from deuterium, a halogen group, a cyano group, a haloalkyl group having 1 to 4 carbon atoms, a deuterated alkyl group having 1 to 4 carbon atoms, an alkyl group having 1 to 4 carbon atoms, a cycloalkyl group having 5 to 10 carbon atoms, an aryl group having 6 to 12 carbon atoms, a deuterated aryl group having 6 to 12 carbon atoms, a heteroaryl group having 5 to 12 carbon atoms, or a trialkylsilyl group having 3 to 8 carbon atoms.

[0072] In some embodiments, Ar1 is selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted spirobifluorenyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted pyrenyl, substituted or unsubstituted cyclopentadienyl, substituted or unsubstituted triphenylene, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted benzodibenzofuranyl, substituted or unsubstituted benzodibenzothiophenyl, substituted or unsubstituted carbazolyl.

[0073] Optionally, the substituents in Ar1 are each independently selected from deuterium, fluorine, cyano, trimethylsilyl, trideuteromethyl, trifluoromethyl, cyclopentyl, cyclohexyl, methyl, ethyl, isopropyl, tert-butyl, phenyl, pentadeuterophenyl, naphthyl, dibenzofuran, and dibenzothiophene.

[0074] In some embodiments, Ar1 is selected from the group consisting of:

[0075]

[0076] In some embodiments, Ar1 is selected from the group consisting of:

[0077]

[0078]

[0079] In some embodiments, Ar2 is selected from a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted aryl group having 6 to 25 carbon atoms, and a substituted or unsubstituted heteroaryl group having 5 to 18 carbon atoms.

[0080] In some embodiments, Ar2 is selected from substituted or unsubstituted alkyl having 1, 2, 3, 4, 5 or 6 carbon atoms, substituted or unsubstituted aryl having 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24 or 25 carbon atoms, and substituted or unsubstituted heteroaryl having 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17 or 18 carbon atoms.

[0081] In some embodiments, the substituents in Ar2 are each independently selected from deuterium, a halogen group, a cyano group, a haloalkyl group having 1 to 4 carbon atoms, a deuterated alkyl group having 1 to 4 carbon atoms, an alkyl group having 1 to 4 carbon atoms, a cycloalkyl group having 5 to 10 carbon atoms, an aryl group having 6 to 15 carbon atoms, a deuterated aryl group having 6 to 12 carbon atoms, a heteroaryl group having 5 to 12 carbon atoms, and a trialkylsilyl group having 3 to 8 carbon atoms; optionally, any two adjacent substituents in Ar2 form a 5-13 membered ring.

[0082] In some embodiments, Ar2 is selected from substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted isopropyl, substituted or unsubstituted tert-butyl, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted tert-phenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted pyrenyl, substituted or unsubstituted triphenylene, substituted or unsubstituted spirobifluorenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted carbazolyl.

[0083] Optionally, the substituents in Ar2 are each independently selected from deuterium, fluorine, cyano, trimethylsilyl, trideuteromethyl, trifluoromethyl, cyclopentyl, cyclohexyl, methyl, ethyl, isopropyl, tert-butyl, phenyl, pentadeuterophenyl, naphthyl, biphenyl, phenanthrenyl, dibenzofuranyl, dibenzothiophenyl or carbazolyl; optionally, any two adjacent substituents in Ar2 form a benzene ring or a fluorene ring.

[0084] In some embodiments, Ar2 is selected from the following groups: methyl, ethyl, n-propyl, isopropyl, tert-butyl,

[0085]

[0086] In some embodiments, Ar2 is selected from the following groups: methyl, ethyl, n-propyl, isopropyl, tert-butyl,

[0087]

[0088]

[0089] In some embodiments, L is selected from the group consisting of:

[0090]

[0091] In some embodiments, L is selected from the group consisting of:

[0092]

[0093]

[0094] In some embodiments, each of R1, R2 and R3 is the same or different and is independently selected from deuterium, cyano, fluorine, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, trifluoromethyl, trideuteromethyl, trimethylsilyl, phenyl, pentadeuterophenyl, biphenyl or naphthyl.

[0095] In some embodiments, the organic compound of the present application is selected from the group consisting of the following compounds:

[0096]

[0097]

[0098]

[0099]

[0100]

[0101]

[0102]

[0103] In a second aspect of the present application, an organic electroluminescent device is provided, 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.

[0104] The organic compound provided in the present application can be used to form at least one organic film layer in a functional layer to improve the luminous efficiency, lifespan and other characteristics of an organic electroluminescent device.

[0105] Optionally, the functional layer includes an organic light-emitting layer, and the organic light-emitting layer includes the organic compound. The organic light-emitting layer can be composed of the organic compound provided in this application, or can be composed of the organic compound provided in this application and other materials.

[0106] According to a specific embodiment, the organic electroluminescent device is as follows Figure 1 As shown, the organic electroluminescent device may include an anode 100, a hole injection layer 310, a hole transport layer 321, an electron blocking layer (hole auxiliary layer) 322, an organic light-emitting layer 330, an electron transport layer 340, an electron injection layer 350 and a cathode 200, which are stacked in sequence.

[0107] In the present application, the anode 100 includes an anode material, which is preferably a material with a large work function that facilitates hole injection into the functional layer. Specific examples of anode materials include: metals such as nickel, platinum, vanadium, chromium, copper, zinc, and gold or 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 are not limited thereto. Preferably, a transparent electrode comprising indium tin oxide (ITO) as an anode is included.

[0108] In the present application, the hole transport layer may include one or more hole transport materials. The hole transport layer material may be selected from carbazole polymers, carbazole-linked triarylamine compounds or other types of compounds, and may specifically be selected from the following compounds or any combination thereof:

[0109]

[0110] In one embodiment, the hole transport layer 321 may be composed of HT-1.

[0111] In one embodiment, the electron blocking layer 322 is composed of EB-1.

[0112] Optionally, a hole injection layer 310 is 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 a benzidine derivative, a starburst arylamine compound, a phthalocyanine derivative, or other materials, and this 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:

[0113]

[0114] In one embodiment, the hole injection layer 310 is composed of HATCN.

[0115] In the present application, 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. Holes and electrons injected into the organic light-emitting layer 330 may recombine in the organic light-emitting layer 330 to form excitons. The excitons transfer energy to the host material, and the host material transfers energy to the guest material, thereby enabling the guest material to emit light.

[0116] The host material of the organic light-emitting layer 330 may include a metal chelate compound, a bisphenylethylene derivative, an aromatic amine derivative, a dibenzofuran derivative, or other types of materials. Alternatively, the host material includes the organic compound of the present application. In some embodiments, the host of the light-emitting layer includes the organic compound of the present application and BH—N.

[0117] The guest material of the organic light-emitting layer 330 can be a compound having a condensed aromatic ring or its derivative, a compound having a heteroaromatic ring or its derivative, an aromatic amine derivative or other materials, and this application does not impose any special restrictions on this. The guest material is also called a doping material or dopant. According to the type of luminescence, it can be divided into fluorescent dopants and phosphorescent dopants. Specific examples of the phosphorescent dopant include, but are not limited to,

[0118] In one embodiment of the present application, the organic electroluminescent device is a blue organic electroluminescent device. In one embodiment, the host material of the organic light-emitting layer 330 comprises the organic compound of the present application. The guest material is, for example, BD. In another embodiment, the host material of the organic light-emitting layer 330 comprises the organic compound of the present application and BH-N The guest material is, for example, BD-1.

[0119] In one embodiment of the present application, the organic electroluminescent device is a blue organic electroluminescent device. In a more specific embodiment, the host material of the organic light-emitting layer 330 comprises the organic compound of the present application.

[0120] 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. The electron transport materials may be selected from, but not limited to, BTB, LiQ, mSiTrz, benzimidazole derivatives, oxadiazole derivatives, quinoxaline derivatives, or other electron transport materials, and are not specifically limited in this application. The materials of the electron transport layer 340 include, but are not limited to, the following compounds:

[0121]

[0122] In one embodiment of the present application, the electron transport layer 340 may be composed of ET-1 and LiQ.

[0123] In the present application, cathode 200 may include a cathode material having 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. Alternatively, a metal electrode containing magnesium and silver may be included as the cathode.

[0124] 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 an inorganic material such as an alkali metal sulfide or an alkali metal halide, or may include a complex of an alkali metal and an organic matter. In one embodiment of the present application, the electron injection layer 350 may include ytterbium (Yb).

[0125] 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.

[0126] According to one embodiment, Figure 2 As shown, the provided electronic device is electronic device 400, which includes the above-mentioned organic electroluminescent device. Electronic device 400 can be, for example, a display device, a lighting device, an optical communication device, or other types of electronic devices, including but not limited to computer screens, mobile phone screens, televisions, electronic paper, emergency lighting, optical modules, etc.

[0127] The synthesis method of the organic compound of the present application is described in detail below with reference to synthesis examples, but the present disclosure is not limited thereby.

[0128] Synthesis Example

[0129] Those skilled in the art will recognize that the chemical reactions described herein can be used to appropriately prepare many of the organic compounds described herein, and that other methods for preparing the compounds described herein are considered within the scope of this application. For example, the synthesis of compounds not exemplified herein can be successfully accomplished by one skilled in the art through modifications such as appropriate protection of interfering groups, the use of known reagents other than those described herein, or conventional modifications of reaction conditions. Compounds for which the syntheses are not described herein are obtained from commercially available raw materials.

[0130] Synthesis of Sub-a1:

[0131]

[0132] Under nitrogen, 3-bromocarbazole (20.00 g, 81.27 mmol), RM-1 (CAS: 87666-63-5, 43.42 g, 121.90 mmol), 18-crown-6 (10.74 g, 40.63 mmol), 1,10-phenanthroline (2.93 g, 16.25 mmol), potassium carbonate (33.69 g, 243.80 mmol), and N,N-dimethylformamide (400 mL) were added to a 1L three-necked flask. The temperature was raised to approximately 120°C, and cuprous bromide (1.17 g, 8.13 mmol) was added. The temperature was then raised to reflux, and the reaction was stirred until the 3-bromocarbazole was completely reacted. After the system temperature dropped to room temperature, the reaction solution was poured into 1000 mL of deionized water and stirred until no solid precipitated. The crude product was purified by silica gel column chromatography using n-heptane / dichloromethane as eluent to obtain Sub-a1 (28.91 g, 75% yield) as a white solid.

[0133] Referring to the synthesis method of Sub-a1, Sub-a2 to Sub-a5 were synthesized by using reactant A shown in Table 1 instead of 3-bromocarbazole and reactant B instead of RM-1.

[0134] Table 1: Synthesis of Sub-a2 to Sub-a5

[0135]

[0136] Synthesis of Sub-b1:

[0137]

[0138] Under nitrogen, a 500 mL three-necked flask was charged with Sub-a1 (20.00 g, 42.16 mmol), diboron pinacol ester (10.71 g, 42.16 mmol), potassium acetate (10.34 g, 105.40 mmol), and 1,4-dioxane (250 mL). The temperature was raised to approximately 100°C, followed by the addition of 1,1-bis(diphenylphosphino)ferrocenepalladium dichloride (617 mg, 0.84 mmol). The temperature was then raised to reflux, and the reaction was stirred until Sub-a1 was completely consumed. After the system cooled to room temperature, 200 mL of deionized water was added and stirred for 5 minutes. The organic phase was separated and the aqueous phase was extracted with dichloromethane (100 mL x 3). The combined organic phases were dried over anhydrous sodium sulfate, filtered, and the solvent was removed by distillation under reduced pressure. The crude product was purified by silica gel column chromatography using n-heptane / dichloromethane as eluent to obtain a white solid Sub-b1 (19.80 g, yield 90%).

[0139] Referring to the synthesis method of Sub-b1, reactant C shown in Table 2 was used instead of Sub-a1 to synthesize Sub-b2 to Sub-b6.

[0140] Table 2: Synthesis of Sub-b2 to Sub-b6

[0141]

[0142]

[0143] Synthesis of Sub-c1:

[0144]

[0145] Under nitrogen, a 500 mL three-necked flask was charged sequentially with Sub-b5 (15.00 g, 39.33 mmol), RM-2 (CAS: 2179279-99-1, 11.07 g, 39.33 mmol), anhydrous potassium carbonate (27.18 g, 196.67 mmol), 200 mL of tetrahydrofuran, and 100 mL of deionized water. The mixture was stirred and heated to approximately 50°C before being added with tetrakistriphenylphosphine palladium (909 mg, 0.79 mmol). The mixture was then heated to reflux for 4 h. After cooling to room temperature, the organic phase was separated and the aqueous phase was extracted with dichloromethane (80 mL x 3). The combined organic phases were dried over anhydrous sodium sulfate, filtered, and the solvent was removed by distillation under reduced pressure. The crude product was purified by silica gel column chromatography using dichloromethane / n-heptane as the mobile phase to obtain Sub-c1 (12.9 g, 72% yield) as a white solid.

[0146] Referring to the synthesis method of compound Sub-c1, reactant D shown in Table 3 was used instead of Sub-b5, and reactant E was used instead of RM-2 to synthesize Sub-c2 to Sub-c22.

[0147] Table 3: Synthesis of Sub-c2 to Sub-c22

[0148]

[0149]

[0150]

[0151] Synthesis of Sub-d1:

[0152]

[0153] Under a nitrogen atmosphere, deuterated bromobenzene (9.1 g, 56.14 mmol) and 250 mL of dried tetrahydrofuran were added sequentially to a 500 mL three-necked flask. After cooling the system to -78°C, n-butyllithium solution (2.0 M in n-hexane, 28 mL, 56.00 mmol) was added dropwise, and the reaction was stirred at this temperature for approximately 1 hour. Subsequently, a solution of RM-3 (CAS: 33584-32-6, 15.00 g, 56.14 mmol) in tetrahydrofuran (50 mL) was added dropwise, and the reaction was continued at this temperature for approximately 4 hours. The system was then allowed to warm to room temperature, and the solvent was removed by distillation under reduced pressure to obtain the crude intermediate Sub-d1, which was used directly in the next reaction without purification.

[0154] Referring to the synthesis method of Sub-d1, reactant F shown in Table 4 was used instead of deuterated bromobenzene to react with RM-3 to synthesize Sub-d2 to Sub-d13.

[0155] Table 4: Synthesis of Sub-d2 to Sub-d13

[0156]

[0157]

[0158] Synthesis of compound 221:

[0159]

[0160] Under a nitrogen atmosphere, Sub-c1 (12.00 g, 26.32 mmol) and 100 mL of dried tetrahydrofuran were added sequentially to a 250 mL three-necked flask. The system was cooled to -78°C, and n-butyllithium solution (2.0 M in n-hexane, 14.5 mL, 29.00 mmol) was added dropwise. The reaction was stirred at this temperature for approximately 1 hour. Subsequently, a solution of RM-4 (CAS: 33584-33-7, 8.94 g, 28.95 mmol) in tetrahydrofuran (50 mL) was added dropwise, and the reaction was continued at this temperature for approximately 4 hours. The mixture was quenched by adding 100 mL of deionized water, and the system was allowed to warm to room temperature naturally. The organic phase was separated and the aqueous phase was extracted with dichloromethane (80 mL × 3). The combined organic phases were dried over anhydrous sodium sulfate, filtered, and the solvent was removed by distillation under reduced pressure. The crude product was purified by silica gel column chromatography using dichloromethane / n-heptane as the mobile phase to obtain compound 221 (9.7 g, 53% yield) as a white solid, m / z 694.30 [M+H] + .

[0161] Referring to the synthesis method of compound 221, the compounds of the present application in Table 5 were synthesized using reactant G shown in Table 5 instead of Sub-c1 and reactant H instead of RM-4.

[0162] Table 5: Synthesis of compounds of the present application

[0163]

[0164]

[0165]

[0166]

[0167]

[0168]

[0169]

[0170] Compound 221 NMR: 1 H NMR(400MHz,CCl2D2)δppm 8.25(d,1H),8.14-8.08(m,2H),7.85(d,1H),7.72-7.65(m,3H),7.42-7.29(m,8H),7.21-7.17(m,2H),6.95-6.90(m,2H).

[0171] Preparation and evaluation of organic electroluminescent devices:

[0172] Example 1: Blue organic electroluminescent device

[0173] Compound HT-1 and HATCN were co-evaporated on the experimental substrate at an evaporation rate ratio of 98%:2% to form a film with a thickness of The hole injection layer is then deposited with compound HT-1 to form a hole injection layer with a thickness of Compound EB-1 was evaporated on the hole transport layer to form a hole transport layer with a thickness of electron blocking layer.

[0174] Next, on the electron blocking layer, compound 221 (hole transport type host), compound BH-N (electron transport type host), and BD-1 were co-evaporated at an evaporation rate ratio of 60%:30%:10% to form a layer with a thickness of blue light emitting layer.

[0175] On the blue light emitting layer, compound ET-1 and LiQ were co-evaporated at an evaporation rate ratio of 50%:50% to form a film with a thickness of an electron transport layer;

[0176] Yb is evaporated on the electron transport layer to form a layer with a thickness of Then, magnesium (Mg) and silver (Ag) were co-evaporated on the electron injection layer at an evaporation rate ratio of 10%:90% to form a thickness of cathode.

[0177] Finally, compound CP-1 is evaporated on the cathode to form a layer with a thickness of The cathode covering layer is formed, thereby completing the preparation of the blue organic electroluminescent device.

[0178] Example 2-Example 39:

[0179] An organic electroluminescent device was prepared by the same method as in Example 1, except that Compound 221 was replaced by Compound P in Table 7 below when preparing the light-emitting layer.

[0180] Comparative Example 1-Comparative Example 3

[0181] An organic electroluminescent device was prepared using the same method as in Example 1, except that compound 221 was replaced by compounds A, B, and C in Table 7 below when preparing the light-emitting layer.

[0182] Table 6

[0183]

[0184]

[0185] The performance of the blue organic electroluminescent devices prepared in Examples 1-39 and Comparative Examples 1-3 was tested. Specifically, the blue organic electroluminescent devices were tested at 10 mA / cm 2 The IVL performance of the device was tested under the condition of , and the T90 device life was tested under the condition of 1000nit brightness. The test results are shown in Table 7 below.

[0186] Table 7

[0187]

[0188]

[0189] Referring to Table 7 above, it can be seen that Examples 1-39 use the compounds of the present application as the main materials of the hole transport layer. Compared with Comparative Examples 1-3, the voltage is reduced by at least 0.24 V, the luminous efficiency is increased by at least 14.2%, and the device T90 life is increased by at least 17.8%.

[0190] It can be seen that using the organic compound of the present application as the main material of the light-emitting layer of an organic electroluminescent device can reduce the device voltage and significantly improve the luminous efficiency and device life of the organic electroluminescent device.

Claims

1. An organic compound, characterized in that It has a structure shown in the following formula 1: wherein X is selected from O or S; Ar1 is selected from a substituted or unsubstituted aryl group having 6 to 40 carbon atoms, or a substituted or unsubstituted heteroaryl group having 3 to 40 carbon atoms; Ar2 is selected from a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 40 carbon atoms, and a substituted or unsubstituted heteroaryl group having 3 to 40 carbon atoms; L is selected from substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenylene; Each of R1, R2 and R3 is the same or different and is independently selected from deuterium, cyano, a halogen group, an alkyl group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, a deuterated alkyl group having 1 to 10 carbon atoms, a trialkylsilyl group having 3 to 12 carbon atoms, a triphenylsilyl group, an aryl group having 6 to 20 carbon atoms, a deuterated aryl group having 6 to 20 carbon atoms, a haloaryl group having 6 to 20 carbon atoms, a heteroaryl group having 3 to 20 carbon atoms, and a cycloalkyl group having 3 to 10 carbon atoms; n1, n2 and n3 represent the number of substituents R1, R2 and R3 respectively, n1 and n2 are the same or different and are independently selected from 0, 1, 2, 3 or 4; n3 is selected from 0, 1, 2, 3, 4, 5, 6 or 7; The substituents in L, 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, triphenylsilyl group, aryl group having 6 to 20 carbon atoms, deuterated aryl group having 6 to 20 carbon atoms, haloaryl group having 6 to 20 carbon atoms, heteroaryl group having 3 to 20 carbon atoms, and cycloalkyl group having 3 to 10 carbon atoms; optionally, any two adjacent substituents in Ar2 form a ring.

2. The organic compound according to claim 1, wherein Ar1 is selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted spirobifluorenyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted pyrenyl, substituted or unsubstituted cyclopentadienyl, substituted or unsubstituted triphenylene, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted benzodibenzofuranyl, substituted or unsubstituted benzodibenzothiophenyl, substituted or unsubstituted carbazolyl; Optionally, the substituents in Ar1 are each independently selected from deuterium, fluorine, cyano, trimethylsilyl, trideuteromethyl, trifluoromethyl, cyclopentyl, cyclohexyl, methyl, ethyl, isopropyl, tert-butyl, phenyl, pentadeuterophenyl, naphthyl, dibenzofuran, and dibenzothiophene.

3. The organic compound according to claim 1, wherein Ar1 is selected from the following groups:

4. The organic compound according to claim 1, wherein Ar2 is selected from substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted isopropyl, substituted or unsubstituted tert-butyl, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted pyrenyl, substituted or unsubstituted triphenylene, substituted or unsubstituted spirobifluorenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted carbazolyl; Optionally, the substituents in Ar2 are each independently selected from deuterium, fluorine, cyano, trimethylsilyl, trideuteromethyl, trifluoromethyl, cyclopentyl, cyclohexyl, methyl, ethyl, isopropyl, tert-butyl, phenyl, pentadeuterophenyl, naphthyl, biphenyl, phenanthrenyl, dibenzofuranyl, dibenzothiophenyl or carbazolyl; optionally, any two adjacent substituents in Ar2 form a benzene ring or a fluorene ring.

5. The organic compound according to claim 1, wherein Ar2 is selected from the following groups: methyl, ethyl, n-propyl, isopropyl, tert-butyl, 6. The organic compound according to claim 1, wherein L is selected from the group consisting of:

7. The organic compound according to claim 1, wherein Each of R1, R2 and R3 is the same or different and is independently selected from deuterium, cyano, fluorine, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, trifluoromethyl, trideuteromethyl, trimethylsilyl, phenyl, pentadeuterophenyl, biphenyl or naphthyl.

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

9. 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; characterized in that: The functional layer comprises the organic compound according to any one of claims 1 to 8; Optionally, the functional layer includes an organic light-emitting layer, and the organic light-emitting layer contains the organic compound.

10. An electronic device, characterized in that The organic electroluminescent device according to claim 9 is included.

Images