Organic compound, electronic element using same, and electronic device

Abstract

An organic compound, an electronic element using same, and an electronic device. The organic compound has a structure represented by formula I. When the organic compound is used in an organic electroluminescent device, the performance of the device can be significantly improved.

Description

Organic compound and electronic component and electronic device using the same

[0001] CROSS-REFERENCE TO RELATED APPLICATIONS

[0002] This application claims priority to Chinese patent applications with application number CN2023112130289 filed on September 19, 2023 and application number CN2023113009802 filed on October 9, 2023, and the full text of the above-mentioned Chinese patent applications is hereby cited as part of this application. Technical Field

[0003] The present application relates to the field of organic electroluminescence, and in particular to an organic compound and an electronic component and an electronic device using the same. Background Art

[0004] With the development of electronic technology and advancements in materials science, the application range of electronic components used to achieve electroluminescence or photoelectric conversion is becoming increasingly widespread. Such electronic components generally include a cathode and an anode arranged in opposite directions, and a functional layer disposed between the cathode and the anode. This functional layer is composed of multiple organic or inorganic film layers and generally includes an energy conversion layer, a hole transport layer located between the energy conversion layer and the anode, and an electron transport layer located between the energy conversion layer and the cathode.

[0005] Taking an organic electroluminescent device as an example, it generally consists of an anode, a hole transport layer, an electroluminescent layer (which serves as an energy conversion layer), an electron transport layer, and a cathode, all stacked in sequence. When a voltage is applied to the cathode and anode, an electric field is generated between the two electrodes. Under the influence of this electric field, electrons on the cathode side migrate toward the electroluminescent layer, and holes on the anode side also migrate 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, causing the electroluminescent layer to emit light outward.

[0006] Summary of the Invention

[0007] The purpose of the present application is to provide an organic compound and an electronic component and an electronic device using the same, wherein the organic compound is used in an organic electroluminescent device to improve the performance of the device.

[0008] The first aspect of the present application provides an organic compound having a structure shown in Formula I:

[0009] Wherein, X1 and X2 are the same or different and are each independently selected from O or S;

[0010] 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, or a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms;

[0011] Ar1 and Ar2 are the same or different and are each independently selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms;

[0012] The substituents in L, L1, L2, Ar1 and Ar2 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 deuterated alkyl group having 1 to 10 carbon atoms, a trialkylsilyl group having 3 to 12 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms or a heteroaryl group having 3 to 20 carbon atoms;

[0013] Both m and n are the number of D, m is 0, 1, 2, 3 or 4, n is 0, 1, 2, 3, 4, 5 or 6, and m+n≥1.

[0014] The second aspect of 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 first aspect of the present application.

[0015] A third aspect of the present application provides an electronic device comprising the electronic component described in the second aspect of the present application.

[0016] The compound of the present application mainly uses an oxygen- or sulfur-containing benzo[1,2-b:3,4-b']dibenzo pentacyclic ring as the parent core structure, deuterates the parent core, and bonds to a triarylamine structure. The aromatic amine compound of this parent core structure has a high glass transition temperature and molecular thermal stability, suitable HOMO and LUMO energy levels, a high triplet energy level T1 and hole mobility, and has better hole transport performance. Moreover, the parent core contains at least one deuterated compound. Compared with a carbon-hydrogen bond, the carbon-deuterium bond has a shorter bond length and a higher bond energy, which makes the central volume of the compound molecule smaller, effectively improves thermal stability, and at the same time gives the compound a higher carrier mobility. When the compound of the present application is used as a luminescence adjustment layer, the luminous efficiency and life of the device can be improved.

[0017] Other features and advantages of the present application will be described in detail in the subsequent detailed description. BRIEF DESCRIPTION OF THE DRAWINGS

[0018] 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.

[0019] FIG1 is a schematic structural diagram of an organic electroluminescent device according to an embodiment of the present application.

[0020] FIG2 is a schematic diagram of a first electronic device according to an embodiment of the present application.

[0021] FIG3 is a schematic structural diagram of a photoelectric conversion device according to an embodiment of the present application.

[0022] FIG4 is a schematic diagram of a second electronic device according to an embodiment of the present application.

[0023] Description of Reference Numerals

[0024] 100, anode; 200, cathode; 300, functional layer; 310, hole injection layer; 321, first hole transport layer; 322, luminescence adjustment layer; 330, organic light-emitting layer; 340, electron transport layer; 350, electron injection layer; 360, photoelectric conversion layer; 320, hole transport layer; 400, first electronic device; 500, second electronic device. DETAILED DESCRIPTION

[0025] 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.

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

[0027] Wherein, X1 and X2 are the same or different and are each independently selected from O or S;

[0028] 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, or a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms;

[0029] Ar1 and Ar2 are the same or different and are each independently selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms;

[0030] The substituents in L, L1, L2, Ar1 and Ar2 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 deuterated alkyl group having 1 to 10 carbon atoms, a trialkylsilyl group having 3 to 12 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms or a heteroaryl group having 3 to 20 carbon atoms;

[0031] Both m and n are the number of D, m is 0, 1, 2, 3 or 4, n is 0, 1, 2, 3, 4, 5 or 6, and m+n≥1.

[0032] In this application, the descriptions “each independently selected from” and “respectively independently selected from” 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. 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.

[0033] 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 or an unsubstituted aryl group having the substituent Rc. The substituent Rc can be, for example, deuterium, a halogen group, a cyano group, an alkyl group, a trialkylsilyl group, a haloalkyl group, a cycloalkyl group, an aryl group, a heteroaryl group, etc.

[0034] 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 L1 is a substituted arylene group with 12 carbon atoms, the total number of carbon atoms in the arylene group and its substituents is 12.

[0035] 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 bond, a monocyclic aryl and a condensed ring aryl connected by a carbon-carbon bond, two or more condensed ring aryl groups connected by a carbon-carbon bond. That is, unless otherwise indicated, two or more aromatic groups connected by a carbon-carbon bond can also be considered as aryl of the present application. Wherein, condensed ring aryl can, for example, include bicyclic condensed aryl (such as naphthyl), tricyclic condensed aryl (such as phenanthrenyl, fluorenyl, anthracenyl) etc. Aryl does not contain heteroatoms such as B, N, O, S, P, Se and Si. For example, in the present application, biphenyl, terphenyl etc. are aryl. Examples of aryl groups may include, but are not limited to, phenyl, naphthyl, fluorenyl, anthracenyl, phenanthrenyl, biphenyl, terphenyl, benzo[9,10]phenanthrenyl, pyrenyl, benzofluoranthenyl, In the present application, the arylene group refers to a divalent group formed by further losing a hydrogen atom from an aryl group.

[0036] In the present application, a substituted aryl group may be an aryl group in which one or more hydrogen atoms are substituted by groups such as a deuterium atom, a halogen group, a cyano group, an aryl group, a heteroaryl group, a trialkylsilyl group, an alkyl group, a cycloalkyl group, a haloalkyl group, a deuterated alkyl group, etc. Specific examples of heteroaryl-substituted aryl groups include, but are not limited to, dibenzofuranyl-substituted phenyl, dibenzothiophene-substituted phenyl, pyridine-substituted phenyl, etc. It should be understood that the number of carbon atoms in a substituted aryl group refers to the total number of carbon atoms in the aryl group and the substituents on the aryl group. For example, a substituted aryl group having 18 carbon atoms refers to a total number of carbon atoms in the aryl group and the substituents.

[0037] In the present application, a heteroaryl group refers to a monovalent aromatic ring or a derivative thereof containing at least one heteroatom in the ring, and the heteroatom can be one or more of B, O, N, P, Si, Se and S. A heteroaryl group can be a monocyclic heteroaryl group or a polycyclic heteroaryl group. In other words, a heteroaryl group can be a single aromatic ring system or a plurality of aromatic ring systems connected by conjugated carbon-carbon bonds, and any aromatic ring system can be an aromatic monocyclic ring or an aromatic condensed ring. For 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 triazinyl 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 silafluorenyl group, a dibenzofuranyl group, an N-phenylcarbazolyl group, an N-pyridylcarbazolyl group, an N-methylcarbazolyl group, and the like, without being limited thereto. In the present application, the heteroarylene group refers to a divalent group formed by further losing a hydrogen atom from a heteroaryl group.

[0038] In the present application, a substituted heteroaryl group may be a heteroaryl group in which one or more hydrogen atoms are replaced by a group such as a deuterium atom, a halogen group, a cyano group, an aryl group, a heteroaryl group, a trialkylsilyl group, an alkyl group, a cycloalkyl group, a haloalkyl group, a deuterated alkyl group, etc. Specific examples of aryl-substituted heteroaryl groups include, but are not limited to, a phenyl-substituted dibenzofuranyl group, a phenyl-substituted dibenzothienyl group, a phenyl-substituted pyridyl group, etc. It should be understood that the number of carbon atoms in a substituted heteroaryl group refers to the total number of carbon atoms in the heteroaryl group and the substituents on the heteroaryl group.

[0039] In the present application, the number of carbon atoms of the aryl group as a substituent may be 6 to 20, for example, the number of carbon atoms may be 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, and specific examples of the aryl group as a substituent include, but are not limited to, phenyl, biphenyl, naphthyl, anthracenyl, base.

[0040] In the present application, the number of carbon atoms of the heteroaryl group as a substituent can be 3 to 20, for example, the number of carbon atoms can be 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20. Specific examples of the heteroaryl group as a substituent include, but are not limited to, pyridyl, pyrimidinyl, carbazolyl, dibenzofuranyl, dibenzothiophenyl, quinolyl, quinazolinyl, quinoxalinyl, and isoquinolyl.

[0041] 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. 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, n-heptyl, n-octyl, 2-ethylhexyl, nonyl, decyl, 3,7-dimethyloctyl, and the like.

[0042] In the present application, the halogen group may be, for example, fluorine, chlorine, bromine, or iodine.

[0043] In the present application, specific examples of trialkylsilyl include, but are not limited to, trimethylsilyl, triethylsilyl, and the like.

[0044] In the present application, specific examples of haloalkyl include, but are not limited to, trifluoromethyl.

[0045] In the present application, specific examples of deuterated alkyl groups include, but are not limited to, trideuterated methyl groups.

[0046] In the present application, "D" in the compound structural formula represents deuterium.

[0047] In this application, a non-positioned connecting bond refers to a single bond extending from the ring system. , which 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. The meaning represented by it includes any possible connection method shown in formulas (f-1) to (f-10):

[0048] 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):

[0049] In some embodiments of the present application, the organic compound is selected from the structure shown in the following formula I-1, formula I-2, formula I-3 or formula I-4:

[0050] L, L1, L2, Ar1 and Ar2, m and n in Formulas I-1 to I-4 are the same as defined in Formula I.

[0051] In some embodiments of the present application, the organic compound is selected from the structure shown in the following formula IX or formula IY:

[0052] X1, X2, L, L1, L2, Ar1 and Ar2, m and n in Formulas I-1 to I-4 are the same as defined in Formula I.

[0053] In some embodiments of the present application, L, L1 and L2 are the same or different and are each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 18 carbon atoms, or a substituted or unsubstituted heteroarylene group having 5 to 18 carbon atoms. For example, 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, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17 or 18 carbon atoms, or a substituted or unsubstituted heteroarylene group having 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17 or 18 carbon atoms.

[0054] In some embodiments of the present application, the substituents in L, L1 and L2 are the same or different and are independently selected from deuterium, fluorine, cyano, trifluoromethyl, trimethylsilyl, an alkyl group having 1 to 5 carbon atoms or a phenyl group.

[0055] In some embodiments of the present application, L, L1 and L2 are the same or different and are each independently selected from a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted anthrylene group, or a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group or a substituted or unsubstituted carbazolyl group.

[0056] In some embodiments of the present application, the substituents in L, L1 and L2 are the same or different and are each independently selected from deuterium, fluorine, cyano, trifluoromethyl, trimethylsilyl, methyl, ethyl, isopropyl, tert-butyl or phenyl.

[0057] In some embodiments of the present application, L is selected from the group consisting of a single bond or the following groups:

[0058] In some embodiments of the present application, L is selected from the group consisting of a single bond or the following groups:

[0059] In some embodiments of the present application, L1 and L2 are the same or different, and are each independently selected from the group consisting of a single bond or the following groups:

[0060] In some embodiments of the present application, L1 and L2 are the same or different, and are each independently selected from the group consisting of a single bond or the following groups:

[0061] 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. For example, Ar1 and Ar2 are the same or different and are each independently selected from a substituted or unsubstituted aryl group having 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 10, 20, 21, 22, 23, 24 or 25 carbon atoms, or a substituted or unsubstituted heteroaryl group having 12, 13, 14, 15, 16, 17 or 18 carbon atoms.

[0062] In some embodiments of the present application, the substituents in Ar1 and Ar2 are the same or different and are each independently selected from deuterium, fluorine, cyano, trimethylsilyl, an alkyl group having 1 to 5 carbon atoms, a haloalkyl group having 1 to 5 carbon atoms, a deuterated alkyl group having 1 to 5 carbon atoms, an aryl group having 6 to 12 carbon atoms, or a heteroaryl group having 5 to 12 carbon atoms.

[0063] 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 phenyl, a substituted or unsubstituted naphthyl, a substituted or unsubstituted biphenyl, a substituted or unsubstituted terphenyl, a substituted or unsubstituted phenanthrenyl, a substituted or unsubstituted fluorenyl, a substituted or unsubstituted spirobifluorene, a substituted or unsubstituted pyrene, a substituted or unsubstituted anthracenyl, a substituted or unsubstituted dibenzofuranyl, a substituted or unsubstituted dibenzothiophenyl, or a substituted or unsubstituted carbazolyl.

[0064] In some embodiments of the present application, the substituents in Ar1 and Ar2 are the same or different and are each independently selected from deuterium, fluorine, cyano, trimethylsilyl, trideuterated methyl, trifluoromethyl, methyl, ethyl, isopropyl, tert-butyl or phenyl.

[0065] 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:

[0066] 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:

[0067] In some embodiments of the present application, are the same or different and are each independently selected from the group consisting of:

[0068] In some embodiments of the present application, are the same or different and are each independently selected from the group consisting of:

[0069] Specifically, the organic compound is selected from the group consisting of the following compounds:

[0070] 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 disposed between the anode and the cathode; the functional layer comprises the organic compound of the present application.

[0071] In some embodiments of the present application, the functional layer includes a first hole transport layer.

[0072] In some embodiments of the present application, the electronic component is an organic electroluminescent device or a photoelectric conversion device.

[0073] In some embodiments of the present application, the organic electroluminescent device is a red organic electroluminescent device.

[0074] In some embodiments of the present application, the functional layer includes a luminescence adjustment layer, and the luminescence adjustment layer includes the organic compound of the present application.

[0075] In one embodiment, the electronic component is an organic electroluminescent device. As shown in FIG1 , the organic electroluminescent device may include a stacked anode 100 , a first hole transport layer 321 , a luminescence adjustment layer 322 , an organic light emitting layer 330 , an electron transport layer 340 , and a cathode 200 .

[0076] In some embodiments of the present application, the anode 100 includes the following anode materials, which are preferably materials with a large work function that facilitates hole injection into the functional layer. Specific examples of anode materials include: metals such as nickel, platinum, vanadium, chromium, copper, zinc, and gold, or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); combinations of metals and oxides such as ZnO:Al or SnO2:Sb; or conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDT), polypyrrole, and polyaniline, but are not limited thereto. Preferably, a transparent electrode comprising indium tin oxide (ITO) as the anode is included.

[0077] In some embodiments of the present application, the first hole transport layer includes one or more hole transport materials, and the first hole transport material can be selected from carbazole polymers, carbazole-linked triarylamine compounds, or other types of compounds. This application does not make special provisions for this. For example, the material of the first hole transport layer is selected from the group consisting of the following compounds:

[0078] In one specific embodiment, the first hole transport layer 321 is HT-25.

[0079] In another specific embodiment, the luminescence adjustment layer 322 is the compound of the present application.

[0080] In the present application, the organic light-emitting layer 330 may be composed of a single light-emitting layer material, or may include a host material and a guest material. In some embodiments of the present application, 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.

[0081] The main material of the organic light-emitting layer 330 can be a metal chelate compound, a bisphenylethylene derivative, an aromatic amine derivative, a dibenzofuran derivative or other types of materials, and this application does not impose any special restrictions on this. The main material can be a single main material or a mixed main material. In one embodiment of the present application, the main material of the organic light-emitting layer 330 is RH

[0082] The guest material of the organic light-emitting layer 330 can be selected according to the prior art, for example, it can be selected from iridium (III) organometallic complexes, platinum (II) organometallic complexes, ruthenium (II) complexes, etc. Specific examples of guest materials include but are not limited to:

[0083] In one embodiment of the present application, the guest material of the organic light-emitting layer 330 is RD.

[0084] In the present application, 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, which can generally include metal complexes and / or nitrogen-containing heterocyclic derivatives. The metal complex can be selected from, for example, LiQ, Alq3, etc.; the nitrogen-containing heterocyclic derivative can be an aromatic ring having a nitrogen-containing six-membered ring or five-membered ring skeleton, a fused 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, ET-19, BimiBphen, or anthracene compounds, triazines, or pyrimidine compounds containing hetero-nitrogen aromatic groups as shown below:

[0085] In one embodiment of the present application, the electron transport layer 340 is composed of ET-19 and LiQ.

[0086] 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. Preferably, a metal electrode containing magnesium and silver is used as the cathode.

[0087] In one embodiment of the present application, as shown in FIG1 , a hole injection layer 310 is further provided between the anode 100 and the first hole transport layer 321 to enhance the ability to inject holes into the first 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. For example, the compound contained in the hole injection layer 310 is selected from the group consisting of the following compounds:

[0088] In a specific embodiment of the present application, the hole injection layer 310 is composed of HT-25 and PD.

[0089] In some embodiments of the present application, as shown in FIG1 , 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 compound. For example, the electron injection layer 350 includes Yb.

[0090] According to another embodiment, the electronic component is a photoelectric conversion device. As shown in FIG3 , the photoelectric conversion device may include an anode 100 and a cathode 200 disposed opposite each other, and a functional layer 300 disposed between the anode 100 and the cathode 200; the functional layer 300 includes the organic compound provided in this application.

[0091] According to a specific embodiment, as shown in Figure 3, the photoelectric conversion device includes an anode 100, a hole transport layer 320, a photoelectric conversion layer 360, an electron transport layer 350, and a cathode 200 stacked in sequence. Optionally, the hole transport layer 320 comprises the organic compound of the present application.

[0092] Alternatively, the photoelectric conversion device may be a solar cell, in particular an organic thin-film solar cell. For example, in one embodiment of the present application, the solar cell comprises an anode, a hole transport layer, a photoelectric conversion layer, an electron transport layer, and a cathode stacked in sequence, wherein the hole transport layer comprises the organic compound of the present application.

[0093] In a third aspect, the present application provides an electronic device comprising the electronic component provided in the second aspect of the present application.

[0094] According to one embodiment, as shown in FIG2 , the electronic device is a first electronic device 400, which includes the organic electroluminescent device described above. The first electronic device 400 may 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, and the like.

[0095] According to another embodiment, as shown in FIG4 , the electronic device is a second electronic device 500 including the above-mentioned photoelectric conversion device. The second electronic device 500 may be, for example, a solar power generation device, a photodetector, a fingerprint recognition device, an optical module, a CCD camera, or other types of electronic devices.

[0096] The synthesis method of the organic compound of the present application is specifically described below with reference to synthesis examples, but the present application is not limited thereto.

[0097] The compounds whose synthesis methods are not mentioned in this application are all raw materials obtained through commercial channels.

[0098] Synthesis example

[0099] 1. Synthesis of IMA-1

[0100] Under N2 protection, raw material 1 (100 g, 296 mmol) (CAS: 2243465-41-8), deuterated benzene (62.6 g, 740 mmol), trifluoromethanesulfonic acid (3 g, 20 mmol) and 1,4-dioxane (800 mL) were added to a three-necked flask and reacted at 90°C for 24 h. After stopping the reaction, the reaction was cooled to room temperature and extracted with dichloromethane and deionized water. The organic phase was washed with water until neutral, dehydrated with anhydrous magnesium sulfate, and concentrated to obtain a crude product, which was recrystallized with a solvent of dichloromethane: ethyl acetate (v / v) = 1:3 to obtain a white oil IMA-1 (35.8 g, yield 35%).

[0101] The intermediates listed in Table 1 were synthesized in the same manner as IMA-1, except that raw material X was used instead of raw material 1. The main raw materials used, the synthesized intermediates and their yields are shown in Table 1.

[0102] Table 1

[0103] 2. Synthesis of Compound 2

[0104] Under N2 protection, IMA-1 (10 g, 28 mmol) and aniline (2.7 g, 28 mmol) were added to a three-necked flask, refluxed at 110 ° C with stirring for 30 min, and then cooled to 80 ° C ~ 90 ° C, and sodium tert-butoxide (4 g, 42 mmol), X-Phos (0.26 g, 5 mmol) and Pd2 (dba) 3 (0.25 g, 2.8 mmol) were added. After reflux at 110 ° C for 3 h, the reaction was stopped. The reaction solution was cooled to room temperature and extracted with toluene and deionized water. The organic phase was washed with water until neutral, dehydrated with anhydrous magnesium sulfate, and passed through a silica gel funnel column with toluene as the eluent. The crude product was concentrated and recrystallized with a solvent of dichloromethane: n-heptane (v / v) = 1:3 to obtain a gray solid IM B-1 (9.1 g, yield 91%).

[0105] Under N2 protection, IM B-1 (9.1 g, 25 mmol) and bromobenzene (4 g, 25 mmol) were placed in a three-necked flask, refluxed at 110 ° C with stirring for 30 min, and then cooled to 80 ° C ~ 90 ° C, and sodium tert-butoxide (3.6 g, 37.5 mmol), S-Phos (0.2 g, 5 mmol) and Pd2 (dba) 3 (0.2 g, 2.5 mmol) were added. After reflux at 108 ° C for 10 h, the reaction was stopped. The reaction solution was cooled to room temperature and extracted with toluene and deionized water. The organic phase was washed with water until neutral and dehydrated with anhydrous magnesium sulfate. Column chromatography was performed using toluene:n-heptane = 1:8 as the eluent. The product spots were collected and concentrated to obtain a crude product, which was recrystallized from dichloromethane:ethyl acetate (v / v) = 1:4 to obtain white solid compound 2 (8.8 g, yield 81%). Mass spectrum (m / z) = 435.20 [M+H] + .

[0106] The compounds listed in Table 2 were synthesized in the same manner as compound 2, except that IM X-1 was used instead of IMA-1, raw material 2 was used instead of aniline, and raw material 3 was used instead of bromobenzene. The main raw materials used, the synthesized compounds, and their final step yields and mass spectra are shown in Table 2:

[0107] Table 2

[0108] NMR data of some compounds

[0109] Example of fabrication and evaluation of organic electroluminescent devices

[0110] Example 1:

[0111] The device was prepared by the following process

[0112] The thickness is On the ITO / Ag / ITO experimental substrate, the surface was treated with ultraviolet, ozone and O2:N2 plasma to increase the work function of the anode, and the surface of the experimental substrate was cleaned with an organic solvent to remove impurities and oil stains on the surface of the experimental substrate.

[0113] On the experimental substrate, compound HT-25 and PD were co-evaporated at an evaporation rate ratio of 97:3 to form a film with a thickness of hole injection layer.

[0114] Compound HT-25 was evaporated on the hole injection layer to form a layer with a thickness of The first hole transport layer.

[0115] Compound 2 is evaporated on the first hole transport layer to form a layer with a thickness of Glow adjustment layer.

[0116] On the luminescence adjustment layer, compounds RH and RD were co-evaporated at an evaporation rate ratio of 98:2 to form a film with a thickness of organic light-emitting layer.

[0117] On the organic light emitting layer, compound ET-19 and LiQ were co-evaporated at an evaporation rate ratio of 50:50 to form a film with a thickness of electron transport layer.

[0118] Yb is evaporated on the electron transport layer to form a layer with a thickness of Then, on the electron injection layer, magnesium (Mg) and silver (Ag) are co-evaporated at an evaporation rate ratio of 10:90 to form a thickness of cathode.

[0119] 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 red organic electroluminescent device.

[0120] Example 2 to Example 28:

[0121] An organic electroluminescent device was prepared using the same method as in Example 1, except that the compound in Table 4 was used instead of Compound 2 in Example 1 when preparing the luminescence adjustment layer.

[0122] Comparative Examples 1 to 4:

[0123] An organic electroluminescent device was prepared using the same method as in Example 1, except that Compounds A, B, C, and D in Table 3 were used instead of Compound 2 in Example 1 when preparing the luminescence adjustment layer.

[0124] The structures of the compounds used in preparing the devices of the above embodiments and comparative examples are listed in Table 3 below:

[0125] Table 3

[0126] The performance of the red organic electroluminescent devices prepared in Examples 1 to 28 and Comparative Examples 1 to 4 was tested. Specifically, at 15 mA / cm 2 The IVL performance of the device was tested under the conditions of 20mA / cm 2 The T95 device life was tested under the conditions of , and the test results are shown in Table 4 below.

[0127] Table 4

[0128] As shown in Table 1 above, when the compounds of the present invention are used in the luminescence adjustment layer of a red organic electroluminescent device, device performance can be significantly improved. Specifically, compared to the organic electroluminescent devices of Comparative Examples 1-4, the organic electroluminescent devices of Examples 1-28 exhibited at least a 10.11% increase in current efficiency and at least an 11% increase in T95 lifetime.

[0129] The preferred embodiments of the present application are described in detail above in conjunction with the accompanying drawings. However, the present application is not limited to the specific details in the above embodiments. Within the technical concept of the present application, various simple modifications can be made to the technical solution of the present application, and these simple modifications all fall within the scope of protection of the present application.

[0130] It should also be noted that the various specific technical features described in the above specific embodiments can be combined in any appropriate manner unless there is any contradiction. In order to avoid unnecessary repetition, this application will not further describe various possible combinations.

Claims

1. An organic compound having a structure shown in Formula I: in, X1 and X2 are the same or different and are each independently selected from O or S; 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, or a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms; Ar1 and Ar2 are the same or different and are each independently selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms; The substituents in L, L1, L2, Ar1 and Ar2 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 deuterated alkyl group having 1 to 10 carbon atoms, a trialkylsilyl group having 3 to 12 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms or a heteroaryl group having 3 to 20 carbon atoms; Both m and n are the number of D, m is 0, 1, 2, 3 or 4, n is 0, 1, 2, 3, 4, 5 or 6, and m+n≥1.

2. The organic compound according to claim 1, wherein L, L1 and L2 are the same or different and are each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 18 carbon atoms, or a substituted or unsubstituted heteroarylene group having 5 to 18 carbon atoms; The substituents in L, L1 and L2 are the same or different and are each independently selected from deuterium, fluorine, cyano, trifluoromethyl, trimethylsilyl, an alkyl group having 1 to 5 carbon atoms or a phenyl group.

3. The organic compound according to claim 1, wherein L, L1 and L2 are the same or different and are each independently selected from a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted anthrylene group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothienyl group, or a substituted or unsubstituted carbazolyl group; The substituents in L, L1 and L2 are the same or different and are each independently selected from deuterium, fluorine, cyano, trifluoromethyl, trimethylsilyl, methyl, ethyl, isopropyl, tert-butyl or phenyl.

4. The organic compound according to claim 1, wherein 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; The substituents in Ar1 and Ar2 are the same or different and are each independently selected from deuterium, fluorine, cyano, trimethylsilyl, an alkyl group having 1 to 5 carbon atoms, a haloalkyl group having 1 to 5 carbon atoms, a deuterated alkyl group having 1 to 5 carbon atoms, an aryl group having 6 to 12 carbon atoms, or a heteroaryl group having 5 to 12 carbon atoms.

5. The organic compound according to claim 1, wherein Ar1 and Ar2 are the same or different and are each independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted spirobifluorene, substituted or unsubstituted pyrenyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl or substituted or unsubstituted carbazolyl; The substituents in Ar1 and Ar2 are the same or different and are each independently selected from deuterium, fluorine, cyano, trimethylsilyl, trideuterated methyl, trifluoromethyl, methyl, ethyl, isopropyl, tert-butyl or phenyl.

6. The organic compound according to claim 1, wherein Ar1 and Ar2 are the same or different and are each independently selected from the group consisting of:

7. The organic compound according to claim 1, wherein The same or different, and each independently selected from the group consisting of the following groups:

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

9. An electronic component, characterized in that The electronic component comprises an anode and a cathode disposed opposite to each other, and a functional layer disposed between the anode and the cathode; wherein the functional layer comprises the organic compound according to any one of claims 1 to 8.

10. The electronic component according to claim 9, wherein The functional layer includes a luminescence adjustment layer, and the luminescence adjustment layer includes the organic compound; Optionally, the electronic component is an organic electroluminescent device or a photoelectric conversion device.

11. An electronic device, characterized in that The electronic device comprises the electronic component according to claim 9 or 10.

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