Organic compound, and electronic element and electronic device using the same

Abstract

The present application relates to an organic compound, and electronic elements and electronic devices using the same. The organic compound has a structure shown in Formula I, and application of the organic compound to an organic electroluminescent device can significantly improve the performance of the device.

Description

Technical Field

[0001] This application relates to the field of organic electroluminescence technology, and more specifically, to an organic compound and electronic components and devices using the same. Background Technology

[0002] With the development of electronic technology and the advancement of materials science, the application range of electronic components used to achieve electroluminescence or photoelectric conversion is becoming increasingly wide. These electronic components typically include a cathode and an anode positioned opposite each other, and a functional layer disposed between the cathode and the anode. This functional layer consists 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.

[0003] Taking an organic electroluminescent device as an example, it generally includes an anode, a hole transport layer, an electroluminescent layer (serving as an energy conversion layer), an electron transport layer, and a cathode, which are stacked sequentially. When a voltage is applied to the anode and cathode, an electric field is generated between the two electrodes. Under the influence of the electric field, electrons on the cathode side move towards the electroluminescent layer, and holes on the anode side also move towards the electroluminescent layer. Electrons and holes combine in the electroluminescent layer to form excitons. The excitons are in an excited state and release energy outward, thereby causing the electroluminescent layer to emit light.

[0004] In the prior art, CN115141173A, CN114478270A, KR1020170126400A, etc., disclose materials that can be used in organic electroluminescent devices. However, it is still necessary to continue to develop new materials to further improve the performance of electronic components. Summary of the Invention

[0005] The purpose of this application is to provide an organic compound and electronic components and devices using the same, wherein using the organic compound in an organic electroluminescent device can improve the device's performance.

[0006] A first aspect of this application provides an organic compound having the structure shown in Formula I:

[0007]

[0008] Where X is O, S or N (R2), and R2 is selected from aryl groups having 6 to 20 carbon atoms;

[0009] L, L1, and L2 may be the same or different, and each is independently selected from single bonds, substituted or unsubstituted aryl groups with 6 to 30 carbon atoms, and substituted or unsubstituted heteroaryl groups with 3 to 30 carbon atoms.

[0010] Ar1 and Ar2 may be the same or different, and each is independently selected from substituted or unsubstituted aryl groups with 6 to 30 carbon atoms, or substituted or unsubstituted heteroaryl groups with 3 to 30 carbon atoms.

[0011] Each R1 is selected from deuterium, halogen group, cyano, alkyl with 1 to 10 carbon atoms, haloalkyl with 1 to 10 carbon atoms, trialkylsilyl with 3 to 12 carbon atoms, triphenylsilyl, aryl with 6 to 20 carbon atoms, or heteroaryl with 3 to 20 carbon atoms;

[0012] n1 represents the number of R1s, and n1 is selected from 0, 1, 2, 3, 4 or 5; optionally, any two adjacent R1s form a saturated or unsaturated 5 to 14-membered ring;

[0013] The substituents in L, L1, L2, Ar1, and Ar2 may be the same or different, and each is independently selected from deuterium, halogen groups, cyano groups, alkyl groups with 1 to 10 carbon atoms, haloalkyl groups with 1 to 10 carbon atoms, trialkylsilyl groups with 3 to 12 carbon atoms, aryl groups with 6 to 20 carbon atoms, or heteroaryl groups with 3 to 20 carbon atoms.

[0014] A second aspect of this application provides an electronic component including an anode and a cathode disposed opposite to each other, and a functional layer disposed between the anode and the cathode; the functional layer comprising the aforementioned organic compound.

[0015] A third aspect of this application provides an electronic device including the electronic components described in the second aspect of this application.

[0016] The core structure of the organic compound in this application is a dibenzo-p-5-membered ring containing heteroatoms (O, N, S) with tetramethyl-substituted cyclohexane. The lone pair electrons of the heteroatoms in the dibenzo-p-5-membered ring can form conjugations with the plane, thereby increasing the degree of conjugation and resulting in high mobility, which is beneficial for reducing device voltage. Introducing tetramethyl-substituted cyclohexane into the dibenzo-p-5-membered ring structure can adjust the spatial configuration, improve the film-forming properties of such materials, enhance device stability, and thus increase device lifetime. Furthermore, it increases the band gap of the material, improving its ability to block excitons, thereby increasing the exciton recombination probability and improving device efficiency. Connecting aromatic amine groups to this core structure can generate a strong conjugation effect, increasing the local electron cloud density and maintaining high hole mobility. Using this organic compound as a hole transport layer in organic electroluminescent devices can effectively reduce the device's operating voltage while improving device efficiency and lifetime.

[0017] Other features and advantages of this application will be described in detail in the following detailed description section. Attached Figure Description

[0018] The accompanying drawings are provided to further understand this application and form part of the specification. They are used together with the following detailed description to explain this application, but do not constitute a limitation thereof.

[0019] Figure 1 This is a schematic diagram of the structure of an organic electroluminescent device according to one embodiment of this application.

[0020] Figure 2 This is a schematic diagram of a first electronic device according to one embodiment of this application.

[0021] Figure 3 This is a schematic diagram of the structure of a photoelectric conversion device according to one embodiment of this application.

[0022] Figure 4 This is a schematic diagram of a second electronic device according to one embodiment of this application.

[0023] Explanation of reference numerals in the attached figures

[0024] 100, Anode; 200, Cathode; 300, Functional Layer; 310, Hole Injection Layer; 320, Hole Transport Layer; 321, First Hole Transport Layer; 322, Second Hole Transport Layer; 330, Organic Light Emitting Layer; 340, Electron Transport Layer; 350, Electron Injection Layer; 360, Photoelectric Conversion Layer; 400, First Electronic Device; 500, Second Electronic Device Detailed Implementation

[0025] Exemplary embodiments will now be described more fully with reference to the accompanying drawings. However, exemplary embodiments can be implemented in many 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 concept of 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 give a full understanding of embodiments of this application.

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

[0027]

[0028] Where X is O, S or N (R2), and R2 is selected from aryl groups having 6 to 20 carbon atoms;

[0029] L, L1, and L2 may be the same or different, and each is independently selected from single bonds, substituted or unsubstituted aryl groups with 6 to 30 carbon atoms, and substituted or unsubstituted heteroaryl groups with 3 to 30 carbon atoms.

[0030] Ar1 and Ar2 may be the same or different, and each is independently selected from substituted or unsubstituted aryl groups with 6 to 30 carbon atoms, or substituted or unsubstituted heteroaryl groups with 3 to 30 carbon atoms.

[0031] Each R1 is selected from deuterium, halogen group, cyano, alkyl with 1 to 10 carbon atoms, haloalkyl with 1 to 10 carbon atoms, trialkylsilyl with 3 to 12 carbon atoms, triphenylsilyl, aryl with 6 to 20 carbon atoms, or heteroaryl with 3 to 20 carbon atoms;

[0032] n1 represents the number of R1s, and n1 is selected from 0, 1, 2, 3, 4 or 5; optionally, any two adjacent R1s form a saturated or unsaturated 5 to 14-membered ring;

[0033] The substituents in L, L1, L2, Ar1, and Ar2 may be the same or different, and each is independently selected from deuterium, halogen groups, cyano groups, alkyl groups with 1 to 10 carbon atoms, haloalkyl groups with 1 to 10 carbon atoms, trialkylsilyl groups with 3 to 12 carbon atoms, aryl groups with 6 to 20 carbon atoms, or heteroaryl groups with 3 to 20 carbon atoms.

[0034] In this application, the descriptive phrases "each independently selected from" and "separately independently selected from" are interchangeable and should be interpreted broadly. They can mean either that the specific options expressed by the same symbol in different groups do not affect each other, or that the specific options expressed by the same symbol in the same group do not affect each other. For example, " In this formula, each q is independently 0, 1, 2 or 3, and each R is independently selected from hydrogen, deuterium, fluorine or chlorine. The meaning is as follows: Formula Q-1 indicates that there are q substituents R on the benzene ring. Each R can be the same or different, and the options of each R do not affect each other. Formula Q-2 indicates that there are q substituents R on each benzene ring of biphenyl. The number q of substituents R on the two benzene rings can be the same or different, and each R can be the same or different. The options of each R do not affect each other.

[0035] In this application, the term "substituted or unsubstituted" means that the functional group described after the term may or may not have substituents (hereinafter, for ease of description, substituents are collectively referred to as Rc). For example, "substituted or unsubstituted aryl" refers to an aryl group having a substituent Rc or an unsubstituted aryl group. The aforementioned substituents, i.e., Rc, can be, for example, deuterium, halogen groups, cyano, alkyl, trialkylsilyl, haloalkyl, cycloalkyl, aryl, heteroaryl, etc.

[0036] In this application, the number of carbon atoms in substituted or unsubstituted functional groups refers to the total number of carbon atoms. For example, if L1 is a substituted arylene with 12 carbon atoms, then the total number of carbon atoms in the arylene and its substituents is 12.

[0037] In this application, aryl refers to any optional functional group or substituent derived from an aromatic carbon ring. An aryl group can be a monocyclic aryl (e.g., phenyl) or a polycyclic aryl; in other words, an aryl group can be a monocyclic aryl, a fused-ring aryl, two or more monocyclic aryl groups linked by carbon-carbon bonds, a monocyclic aryl and a fused-ring aryl linked by carbon-carbon bonds, or two or more fused-ring aryl groups linked by carbon-carbon bonds. That is, unless otherwise stated, two or more aromatic groups linked by carbon-carbon bonds can also be considered aryl groups in this application. Fused-ring aryl groups may include, for example, bicyclic fused aryl (e.g., naphthyl), tricyclic fused aryl (e.g., phenanthrene, fluorenyl, anthracene), etc. The aryl group does not contain heteroatoms such as B, N, O, S, P, Se, and Si. For example, in this application, biphenyl, terphenyl, etc., are aryl groups. Examples of aryl groups may include, but are not limited to, phenyl, naphthyl, fluorenyl, anthraceneyl, phenanthryl, biphenyl, terphenyl, benzo[9,10]phenanthryl, pyrene, benzofluoranthraceneyl, etc. In this application, the term "arylene" refers to a divalent group formed by the further loss of a hydrogen atom from an aryl group.

[0038] In this application, the substituted aryl group can be one or more hydrogen atoms of the aryl group that are replaced by groups such as deuterium, halogen groups, cyano, aryl, heteroaryl, trialkylsilyl, alkyl, cycloalkyl, haloalkyl, deuteralkyl, 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 the substituted aryl group refers to the total number of carbon atoms of the aryl group and the substituents on the aryl group. For example, a substituted aryl group with 18 carbon atoms means that the total number of carbon atoms of the aryl group and the substituents is 18.

[0039] In this application, a heteroaryl group refers to a monovalent aromatic ring or its derivative containing at least one heteroatom. 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 system of multiple aromatic rings connected by carbon-carbon bonds in a conjugated manner. Any aromatic ring system can be a single aromatic monocyclic ring or a fused aromatic ring. For example, heteroaryl groups may include, but are not limited to, thiopheneyl, furanyl, pyrrolyl, imidazolyl, thiazolyl, oxazolyl, oxadiazolyl, triazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, acridineyl, pyridazinyl, quinolinyl, quinazolinyl, quinoxazinyl, phenoxazinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, isoquinolinyl, indolyl, carbazoleyl, benzoxazolyl, benzoimidazolyl, benzothiazolyl, benzocarbazoleyl, benzothiaphenyl, dibenzothiaphenyl, thiaphenothiaphenyl, benzofuranyl, phenanthrololinyl, isoxazolyl, thiadiazolyl, phenthiaazinyl, silfluorenyl, dibenzofuranyl, and N-phenylcarbazoleyl, N-pyridylcarbazoleyl, N-methylcarbazoleyl, etc. In this application, the term "hybrid aryl" refers to a divalent group formed by the further loss of a hydrogen atom by a heteroaryl group.

[0040] In this application, the substituted heteroaryl group can be one or more hydrogen atoms of the heteroaryl group that are substituted by groups such as deuterium atoms, halogen groups, -CN, aryl, heteroaryl, trialkylsilyl, alkyl, cycloalkyl, haloalkyl, deuteralkyl, etc. Specific examples of aryl-substituted heteroaryl groups include, but are not limited to, phenyl-substituted dibenzofuranyl, phenyl-substituted dibenzothiophenyl, phenyl-substituted pyridyl, etc. It should be understood that the number of carbon atoms in the substituted heteroaryl group refers to the total number of carbon atoms of the heteroaryl group and the substituents on the heteroaryl group.

[0041] In this application, the aryl group used as a substituent can have 6 to 20 carbon atoms, for example, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, or 20 carbon atoms. Specific examples of aryl groups used as substituents include, but are not limited to, phenyl, biphenyl, naphthyl, and anthraceneyl groups. base.

[0042] In this application, the number of carbon atoms in the heteroaryl group used 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, or 20. Specific examples of heteroaryl groups used as substituents include, but are not limited to, pyridinyl, pyrimidinyl, carbazolyl, dibenzofuranyl, dibenzothiophenyl, quinolinyl, quinazolinyl, quinoxalinyl, and isoquinolinyl.

[0043] In this application, alkyl groups having 1 to 10 carbon atoms can include straight-chain alkyl groups having 1 to 10 carbon atoms and branched alkyl groups having 3 to 10 carbon atoms. The number of carbon atoms in an alkyl group can be, for example, 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10. Specific examples of alkyl groups include, but are not limited to, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl, neopentyl, n-hexyl, n-heptyl, n-octyl, 2-ethylhexyl, nonyl, decyl, and 3,7-dimethyloctyl.

[0044] In this application, the halogen group may be, for example, fluorine, chlorine, bromine, or iodine.

[0045] In this application, specific examples of trialkylsilyl groups include, but are not limited to, trimethylsilyl, triethylsilyl, etc.

[0046] In this application, specific examples of alkyl halogens include, but are not limited to, trifluoromethyl.

[0047] In this application, a ring system formed by n atoms is called an n-membered ring. For example, phenyl is a 6-membered aryl group.

[0048] In this application, a non-positioned linker bond refers to a single bond extending from the ring system. This indicates that one end of the linker can connect to any position in the ring system it traverses, and the other end connects to the rest of the compound molecule. For example, as shown in equation (f) below, the naphthyl group represented by equation (f) is connected to other positions in the molecule through two non-positional linkers that traverse the bicyclic ring. This means that any possible connection mode shown in equations (f-1) to (f-10) is included.

[0049]

[0050] For another example, as shown in equation (X'), the dibenzofuran group represented by equation (X') is connected to other positions in the molecule via a non-positional linker extending from the middle of one side of the benzene ring. This means that any possible connection mode shown in equations (X'-1) to (X'-4) is included.

[0051]

[0052] In some embodiments of this application, the organic compound has the structure shown in Formulas I-1 to I-9:

[0053]

[0054]

[0055] In this application, the terms "optional" or "optionally" mean that the event or situation described below may, but does not necessarily, occur. This description includes the possibility that the event or situation may or may not occur. For example, "optionally, any two adjacent substituents ×× form a ring" means that the two substituents may form a ring but are not required to do so, including both scenarios where the two adjacent substituents form a ring and scenarios where the two adjacent substituents do not form a ring. As another example, "optionally, any two adjacent R1s form a saturated or unsaturated 5- to 14-membered ring" means that any two adjacent R1s can connect to each other to form a saturated or unsaturated 5- to 14-membered ring, or any two adjacent R1s can exist independently.

[0056] In some embodiments of this application, R2 is selected from aryl groups having 6 to 12 carbon atoms.

[0057] Optionally, R2 is selected from phenyl, naphthyl, or biphenyl.

[0058] In some embodiments of this application, R1 is selected from deuterium, fluorine, cyano, trimethylsilyl, trifluoromethyl, methyl, ethyl, isopropyl, tert-butyl, phenyl, naphthyl, biphenyl, dibenzofuranyl, dibenzothiopheneyl or carbazoleyl. Optionally, any two adjacent R1s form a benzene ring, a naphthyl ring or a phenanthrene ring.

[0059] In some embodiments of this application, L, L1, and L2 may be the same or different, and each is independently selected from single-bonded substituted or unsubstituted aryl groups with 6 to 18 carbon atoms, or substituted or unsubstituted heteroaryl groups with 5 to 18 carbon atoms. For example, L, L1, and L2 may be the same or different, and each is independently selected from single-bonded substituted or unsubstituted aryl groups with 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, or 18 carbon atoms, or substituted or unsubstituted heteroaryl groups with 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, or 18 carbon atoms.

[0060] Optionally, the substituents in L, L1 and L2 may be the same or different, and each may be independently selected from deuterium, fluorine, cyano, trifluoromethyl, trimethylsilyl, alkyl with 1 to 5 carbon atoms or aryl with 6 to 12 carbon atoms.

[0061] In some embodiments of this application, L, L1, and L2 may be the same or different, and each is independently selected from single bonds, substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted biphenylene, substituted or unsubstituted dibenzofuranylene, substituted or unsubstituted dibenzothiopheneylene, and substituted or unsubstituted carbazolylene.

[0062] Optionally, the substituents in L, L1 and L2 may be the same or different, and each may be independently selected from deuterium, fluorine, cyano, trifluoromethyl, trimethylsilyl, methyl, ethyl, isopropyl, tert-butyl or phenyl.

[0063] In some embodiments of this application, L1 and L2 may be the same or different, and each is independently selected from the group consisting of single bonds or the following groups:

[0064]

[0065] Further optionally, L1 and L2 may be the same or different, and each is independently selected from the group consisting of single bonds or the following groups:

[0066]

[0067]

[0068] In some embodiments of this application, L is selected from single bonds or the following groups:

[0069]

[0070] Further, optionally, L is selected from a single bond or the following groups:

[0071]

[0072] In some embodiments of this application, Ar1 and Ar2 may be the same or different, and each is independently selected from substituted or unsubstituted aryl groups having 6 to 25 carbon atoms, or substituted or unsubstituted heteroaryl groups having 5 to 18 carbon atoms. For example, Ar1 and Ar2 may be the same or different, and each is independently selected from substituted or unsubstituted aryl groups 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 substituted or unsubstituted heteroaryl groups having 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, or 18 carbon atoms.

[0073] Optionally, the substituents in Ar1 and Ar2 may be the same or different, and each may be independently selected from deuterium, fluorine, cyano, trimethylsilyl, trifluoromethyl, alkyl with 1 to 5 carbon atoms, aryl with 6 to 12 carbon atoms, or heteroaryl with 3 to 12 carbon atoms.

[0074] In some embodiments of this application, Ar1 and Ar2 may be the same or different, and each is independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted phenanthyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted triphenylene, substituted or unsubstituted spirofluorene, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, and substituted or unsubstituted carbazole.

[0075] Optionally, the substituents in Ar1 and Ar2 may be the same or different, and each may be independently selected from deuterium, fluorine, cyano, trimethylsilyl, trifluoromethyl, methyl, ethyl, isopropyl, tert-butyl, phenyl, naphthyl, biphenyl, dibenzofuranyl, dibenzothiophenyl, or carbazoyl.

[0076] In some embodiments of this application, Ar1 and Ar2 may be the same or different, and each is independently selected from the group consisting of:

[0077]

[0078] Further, Ar1 and Ar2 may be the same or different, and each may be independently selected from the group consisting of:

[0079]

[0080] In some embodiments of this application, and They may be the same or different, and each is independently selected from the group consisting of the following groups:

[0081]

[0082] Further optional, and They may be the same or different, and each is independently selected from the group consisting of the following groups:

[0083]

[0084] Specifically, the organic compound is selected from the group consisting of:

[0085]

[0086]

[0087]

[0088]

[0089]

[0090]

[0091] Secondly, this application provides an electronic component, including an anode and a cathode disposed opposite to each other, and a functional layer disposed between the anode and the cathode; the functional layer contains the organic compound of this application.

[0092] Optionally, the functional layer includes a hole transport layer, which contains the organic compound.

[0093] Optionally, the electronic component is an organic electroluminescent device or a photoelectric conversion device.

[0094] Optionally, the organic electroluminescent device is a green organic electroluminescent device.

[0095] Further optionally, the hole transport layer includes a first hole transport layer and a second hole transport layer, wherein the first hole transport layer is closer to the anode than the second hole transport layer, and the second hole transport layer contains the organic compound of this application.

[0096] In one embodiment, the electronic component is an organic electroluminescent device. For example... Figure 1 As shown, the organic electroluminescent device may include a stacked anode 100, a first hole transport layer 321, a second hole transport layer 322, an organic light-emitting layer 330, an electron transport layer 340, and a cathode 200. The first hole transport layer 321 and the second hole transport layer 322 constitute the hole transport layer 320.

[0097] Optionally, the anode 100 comprises an anode material, preferably one with a high 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.

[0098] Optionally, the hole transport layer includes one or more hole transport materials, which may be selected from carbazole polymers, carbazole-linked triarylamine compounds, or other types of compounds. This application does not specify any particular type of material. For example, the material of the first hole transport layer may be selected from the group consisting of the following compounds:

[0099]

[0100] In one specific embodiment, the first hole transport layer 321 is HT-31; the second hole transport layer 322 is the compound of this application.

[0101] Optionally, the organic light-emitting layer 330 may be composed of a single light-emitting layer material, or it 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 can 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.

[0102] The host material of the organic light-emitting layer 330 can be a metal chelate compound, a bis(styrene) derivative, an aromatic amine derivative, a dibenzofuran derivative, or other types of materials; this application does not impose any special limitations on this. The host material can be a single host material or a mixture of host materials. In one embodiment of this application, the host materials of the organic light-emitting layer 330 are compound GHP1 and compound GHN1.

[0103] The guest material of the organic light-emitting layer 330 can be selected with reference to existing technologies, such as iridium (III) organometallic complexes, platinum (II) organometallic complexes, ruthenium (II) complexes, etc. Specific examples of the guest material include, but are not limited to,

[0104]

[0105] In one embodiment of this application, the guest material of the organic light-emitting layer 330 is Ir(ppy)3.

[0106] Optionally, the electron transport layer 340 can be a single-layer structure or a multi-layer structure, and may include one or more electron transport materials. The electron transport materials typically include metal complexes and / or nitrogen-containing heterocyclic derivatives. The metal complex material may be selected from, for example, LiQ, Alq3, etc. The nitrogen-containing heterocyclic derivative may be an aromatic ring with a nitrogen-containing six-membered or five-membered ring skeleton, a fused aromatic ring compound with a nitrogen-containing six-membered or five-membered ring skeleton, etc. Specific examples include, but are not limited to, 1,10-phenanthroline compounds such as Bphen, NBphen, ET-1, and BimiBphen, or anthracene compounds, triazine compounds, or pyrimidine compounds containing heteronitrogenous aryl groups as shown below. In one embodiment of this application, the electron transport layer 340 is composed of ET-1 and LiQ.

[0107]

[0108]

[0109] In this application, the cathode 200 may include a cathode material that has a small work function and 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 comprising magnesium and silver is included as the cathode.

[0110] Optionally, such as Figure 1 As shown, a hole injection layer 310 is further disposed 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 can be selected from benzidine derivatives, starburst-like aryl amine compounds, phthalocyanine derivatives, or other materials; this application does not impose any special limitations on this. For example, the compounds contained in the hole injection layer 310 are selected from the group consisting of the following compounds:

[0111]

[0112] In one specific embodiment of this application, the hole injection layer 310 is HT-31 and NDP-9.

[0113] Optionally, such as Figure 1 As shown, an electron injection layer 350 is further disposed between the cathode 200 and the electron transport layer 340 to enhance the ability to inject electrons into the electron transport layer 340. The electron injection layer 350 may include inorganic materials such as alkali metal sulfides and alkali metal halides, or may include complexes of alkali metals and organic materials. For example, the electron injection layer 350 includes Yb.

[0114] According to a specific implementation method, such as Figure 3 As shown, the photoelectric conversion device includes an anode 100, a hole transport layer 320, a photoelectric conversion layer 360, an electron transport layer 340, and a cathode 200, which are stacked sequentially. Optionally, the hole transport layer 320 contains the organic compound of this application.

[0115] Optionally, the photoelectric conversion device can be a solar cell, especially an organic thin-film solar cell. For example, in one embodiment of this application, the solar cell includes an anode, a hole transport layer, a photoelectric conversion layer, an electron transport layer, and a cathode stacked sequentially, wherein the hole transport layer contains the organic compound of this application.

[0116] Thirdly, this application provides an electronic device including the electronic components provided in the second aspect of this application.

[0117] According to one implementation method, such as Figure 2 As shown, the electronic device is a first electronic device 400, which includes the aforementioned organic electroluminescent device. The first electronic device 400 can be, for example, a display device, a lighting device, an optical communication device, or other types of electronic devices, such as, but not limited to, computer screens, mobile phone screens, televisions, electronic paper, emergency lighting, optical modules, etc.

[0118] According to another implementation method, such as Figure 4 As shown, the electronic device is a second electronic device 500, which includes the aforementioned 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.

[0119] The following examples illustrate the synthesis methods of the organic compounds described in this application, but this application is not limited in any way as a result.

[0120] Compounds synthesized using methods not mentioned in this application are all raw material products obtained through commercial means.

[0121] Synthesis example

[0122] 1. Synthesis of IM a1

[0123]

[0124] 2-Bromo-3-fluoro-phenylethanol (50.0 g, 228.3 mmol) and diethyl ether (400 mL) were added to a round-bottom flask, and thionyl chloride (SOCl2) (32.6 g, 274.0 mmol) and pyridine (0.8 g, 10.1 mmol) were slowly added dropwise. The mixture was stirred at room temperature for 2 h. The reaction solution was quenched with water, and the organic phase was separated. The organic phase was dried over anhydrous magnesium sulfate and the solvent was removed under reduced pressure. The crude product was purified by silica gel column chromatography using a heptane system to obtain an oily IM i1 (40.1 g, yield 74%).

[0125]

[0126] IM i1 (40.0 g, 168.4 mmol), 4-chloro-2-hydroxyphenylboronic acid (30.2 g, 176.8 mmol), potassium carbonate (K2CO3) (46.6 g, 336.8 mmol), tetrakis(triphenylphosphine)palladium (Pd(pph3)4) (3.8 g, 3.4 mmol), tetrabutylammonium bromide (TBAB) (10.9 g, 33.7 mmol), toluene (PhMe) (320 mL), ethanol (EtOH) (160 mL), and deionized water (80 mL) were added to a round-bottom flask. The mixture was stirred and heated to 75 °C–80 °C under nitrogen protection and reacted for 16 h. The reaction mixture was cooled to room temperature, washed with water, and the organic phase was separated. The organic phase was dried over anhydrous magnesium sulfate and the solvent was removed under reduced pressure. The crude product was purified by silica gel column chromatography using dichloromethane / n-heptane as eluent to obtain an oily product IM a1 (32.6 g, yield 68.0%).

[0127] The intermediates listed in Table 1 were synthesized using the same method as IM a1, except that starting material 1 was used instead of 4-chloro-2-hydroxyphenylboronic acid. The main starting materials used, the intermediates synthesized, and their yields are shown in Table 1.

[0128] Table 1

[0129]

[0130] 2. Synthesis of IM b1

[0131]

[0132] IM a1 (20.0 g, 70.1 mmol) and dichloromethane (300 mL) were added to a round-bottom flask and stirred under nitrogen protection until the temperature dropped to -5 °C to 0 °C. Boron trifluoride diethyl ether (14.9 g, 105.2 mmol) was slowly added dropwise. After the addition was complete, the mixture was stirred at -5 °C to 0 °C for 30 min, then heated to 20 °C to 25 °C and stirred for 2 h. Sodium bicarbonate aqueous solution and dichloromethane were added to the reaction solution to separate the organic phase. The organic phase was dried over anhydrous magnesium sulfate and the solvent was removed under reduced pressure. The crude product was purified by silica gel column chromatography using a dichloromethane / n-heptane system to obtain a white solid IMb2 (13.0 g, 70% yield).

[0133] The intermediates listed in Table 2 were synthesized using the same method as IM b1, except that raw material 2 was used instead of IMa1. The main raw materials used, the intermediates synthesized, and their yields are shown in Table 2.

[0134] Table 2

[0135]

[0136] 3. Synthesis of IM c1

[0137]

[0138] IM b1 (20.0 g, 75.4 mmol), K2CO3 (20.8 g, 150.8 mmol), Pd(OAc)2 (0.8 g, 3.8 mmol), tricyclohexylphosphine fluoroborate (2.8 g, 7.5 mmol), and N,N-dimethylacetamide (DMAc) (400 mL) were added to a round-bottom flask. The mixture was stirred and heated to 130 °C under nitrogen protection and reacted for 24 h. After cooling to room temperature, dichloromethane and water were added to the reaction solution. The mixture was washed three times with water, and the organic phase was separated. The solution was dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure to obtain the crude product. The crude product was purified by silica gel column chromatography using a dichloromethane / n-heptane system to obtain a white solid IM i2 (12.4 g, yield 72%).

[0139]

[0140] IM i2 (20.0 g, 87.4 mmol), FeCl3 (0.06 g, 0.4 mmol), 70 wt% aqueous solution of tert-butyl hydroperoxide (31.6 g, 349.6 mmol) and acetonitrile (400 mL) were added to a round-bottom flask, stirred, and heated to 60 °C for 16 h. After cooling to room temperature, dichloromethane and water were added to the reaction solution, and the organic phase was separated after washing three times with water. The solution was dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure to obtain the crude product. The crude product was purified by silica gel column chromatography using a dichloromethane / n-heptane system to obtain a white solid IM i3 (16.8 g, yield 75%).

[0141]

[0142] IM i3 (20.0 g, 77.9 mmol) and dry tetrahydrofuran (200 mL) were added to a round-bottom flask. Under nitrogen protection, the mixture was stirred and cooled to -10 °C. A tetrahydrofuran solution of methyl magnesium chloride (46.7 g, 623.6 mmol) was slowly added dropwise. After the addition was complete, the mixture was stirred at -10 °C for 1 h, then heated to 25 °C and stirred for 12 h. A saturated aqueous solution of ammonium chloride was added to the reaction mixture, and the organic phase was separated by extraction with dichloromethane. The organic phase was dried with anhydrous magnesium sulfate and the solvent was removed under reduced pressure. The crude product was purified by silica gel column chromatography using a dichloromethane / n-heptane system to obtain IM c1 (11.6 g, yield 52.3%).

[0143] The intermediates listed in Table 3 were synthesized using the same method as IM c1, except that raw material 3 was used instead of IMb1. The main raw materials used, the intermediates synthesized, and the yield of the final step are shown in Table 3.

[0144] Table 3

[0145]

[0146] 4. Synthesis of IM c6

[0147]

[0148] IM c1 (20 g, 70.2 mmol), pinacol diboronate ((BPin)2, 21.4 g, 84.2 mmol), tris(dibenzylacetone)palladium (Pd2(dba)3, 0.7 g, 0.7 mmol), 2-dicyclohexylphosphine-2',4',6'-triisopropylbiphenyl (X-Phos, 0.6 g, 1.4 mmol), potassium acetate (KOAc, 13.7 g, 140.4 mmol), and 1,4-dioxane (160 mL) were added to a flask and stirred under nitrogen protection at 100-105 °C for 16 h. The mixture was cooled to room temperature, and dichloromethane and water were added to the reaction solution. The mixture was separated, and the organic phase was washed with water and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure to obtain the crude product. The crude product was purified by silica gel column chromatography using a dichloromethane / n-heptane system to obtain a white solid IM. i4 (20.7g, yield 78.2%).

[0149]

[0150] IM i4 (20 g, 53.1 mmol), 4-bromochlorobenzene (11.1 g, 58.4 mmol), tetrakis(triphenylphosphine)palladium (1.3 g, 1.1 mmol), potassium carbonate (14.8 g, 106.2 mmol), tetrabutylammonium bromide (3.4 g, 10.6 mmol), toluene (160 mL), ethanol (80 mL), and deionized water (40 mL) were added to a round-bottom flask. The mixture was stirred and heated to 75 °C–80 °C under nitrogen protection and reacted for 12 h. The reaction mixture was cooled to room temperature, washed with water, and the organic phase was separated. The organic phase was dried over anhydrous magnesium sulfate and the solvent was removed under reduced pressure. The crude product was purified by silica gel column chromatography using dichloromethane / n-heptane as eluent to obtain a white solid IM c6 (15.7 g, yield 81.8%).

[0151] The intermediates listed in Table 4 were synthesized using the same method as IM c6, except that starting material 4 was used instead of 4-bromochlorobenzene. The main starting materials used, the intermediates synthesized, and the yield of the final step are shown in Table 4.

[0152] Table 4

[0153]

[0154] 5. Synthesis of IM i5

[0155]

[0156] IM c1 (20 g, 70.2 mmol), dichloromethane (200 mL), glacial acetic acid (100 mL), and iron powder (1.4 g) were added to a round-bottom flask. 30 mL of a dichloromethane solution containing liquid bromine (13.44 g, 0.084 mmol) was slowly added dropwise at 20 °C–25 °C, and the reaction was carried out at 35 °C–40 °C for 4 h. The reaction mixture was cooled to room temperature, washed with water until neutral, and the organic phase was separated. The organic phase was dried over anhydrous magnesium sulfate and the solvent was removed under reduced pressure. The crude product was purified by silica gel column chromatography using dichloromethane / n-heptane as eluent to give a white solid IM i5 (10.2 g, yield 40.1%).

[0157]

[0158] IM i5 (10 g, 27.5 mmol), phenylboronic acid (3.69 g, 30.3 mmol), tetra(triphenylphosphine)palladium (0.7 g, 0.55 mmol), potassium carbonate (7.7 g, 55 mmol), tetrabutylammonium bromide (1.8 g, 5.5 mmol), toluene (80 mL), ethanol (40 mL), and deionized water (20 mL) were added to a round-bottom flask. The mixture was stirred and heated to 75 °C–80 °C under nitrogen protection and reacted for 6 h. The reaction mixture was cooled to room temperature, washed with water, and the organic phase was separated. The organic phase was dried over anhydrous magnesium sulfate and the solvent was removed under reduced pressure. The crude product was purified by silica gel column chromatography using dichloromethane / n-heptane as eluent to give a white solid IM c10 (8.2 g, yield 83.0%).

[0159] 6. Synthesis of Compound 1

[0160]

[0161] Under nitrogen protection, IM c1 (5 g, 18 mmol), N-phenyl-4-benzidine (4.3 g, 18 mmol), and toluene (50 mL) were added to a three-necked flask. The mixture was heated to reflux and allowed to remove water for 0.5 h. Heating was then stopped, and the mixture was cooled to 80 °C. Sodium tert-butoxide (t-BuONa, 2.6 g, 27 mmol), S-Phos (0.15 g, 0.36 mmol), and Pd2(dba)3 (0.17 g, 0.18 mmol) were added sequentially, and the mixture was refluxed again for 2 h. After the reaction was complete, the mixture was cooled to room temperature, washed three times with water, and the organic phase was separated. The organic phase was dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The crude product was purified by silica gel column chromatography using dichloromethane / n-heptane, followed by recrystallization from toluene / n-heptane to give compound 1 (4 g, yield 46.1%); mass spectrometry (m / z) = 494.2 [M+H]. + .

[0162] The compounds listed in Table 5 below were synthesized using the same method as compound 1, except that IM cX was used instead of IM c1 and starting material 5 was used instead of N-phenyl-4-benzidine. The main starting materials used, the synthesized compounds, their yields, and mass spectra are shown in Table 5.

[0163] Table 5

[0164]

[0165]

[0166]

[0167]

[0168] NMR data for some compounds are shown in Table 6:

[0169] Table 6

[0170]

[0171] Fabrication and evaluation of organic electroluminescent devices:

[0172] Example 1: Fabrication of Green Organic Electroluminescent Devices

[0173] The thicknesses are sequentially as follows: The ITO / Ag / ITO substrate is cut into dimensions of 40mm (length) × 40mm (width) × 0.7mm (thickness). It is then prepared into an experimental substrate with an anode and insulating layer pattern using a photolithography process. The substrate can be surface treated with ultraviolet ozone and O2:N2 plasma to improve the anode work function. The surface of the ITO substrate is cleaned with organic solvents to remove impurities and oil stains.

[0174] First, compounds HT-31 and NDP-9 were co-deposited on the experimental substrate (anode) at a deposition rate ratio of 97%:3% to form a thickness of [missing information]. A hole injection layer is formed, and then HT-31 is vacuum-deposited on the hole injection layer to form a thickness of [thickness missing]. The first hole transport layer.

[0175] Compound 1 is vacuum-deposited on the first hole transport layer to form a thickness of The second hole transport layer.

[0176] On the second hole transport layer, compound GHP1:compound GHN1:Ir(ppy)3 were co-deposited at a deposition rate ratio of 45%:45%:10% to form a layer with a thickness of [missing information]. The organic light-emitting layer.

[0177] On the organic light-emitting layer, ET-1 and LiQ are co-deposited at a 1:1 evaporation rate ratio to form... A thick electron transport layer (ETL) is formed, and then Yb is vacuum-deposited onto the electron transport layer to form a thickness of [thickness value missing]. An electron-injected layer was formed, and then magnesium (Mg) and silver (Ag) were co-deposited onto the electron-injected layer at a evaporation rate ratio of 1:9 to form a thickness of [missing information]. The cathode.

[0178] Finally, CP-1 is deposited on the cathode to form a thickness of [thickness value missing]. The organic coating layer (CPL) is used to complete the fabrication of green organic light-emitting devices.

[0179] Examples 2-23

[0180] Except that, when forming the second hole transport layer, the organic electroluminescent device was prepared using the same method as in Example 1, except that the compound shown in Table 8 was used instead of compound 1 as the second hole transport material.

[0181] Comparative Examples 1-4

[0182] Except that compounds A, B, C, and D were used instead of compound 1 as the second hole transport material when forming the second hole transport layer, the organic electroluminescent device was prepared using the same method as in Example 1.

[0183] The main material structures used in the above embodiments and comparative examples are shown in Table 7 below.

[0184] Table 7

[0185]

[0186] Performance tests were performed on the devices prepared in the examples and comparative examples. IVL (drive voltage, current efficiency, color coordinates) data were obtained at 10 mA / cm². 2 The T95 lifetime is 30 mA / cm² when tested at current density. 2 The results of the tests at current density are shown in Table 8.

[0187] Table 8

[0188]

[0189]

[0190] According to the results in Table 8, compared with Comparative Examples 1 to 4 which use known compounds as the second hole transport layer, Examples 1 to 23 using the organic compounds of this application as the second hole transport layer have a current efficiency that is at least 13.05% higher and a lifetime that is at least 10.5% higher.

[0191] The preferred embodiments of this application have been described in detail above with reference to the accompanying drawings. However, this application is not limited to the specific details of the above embodiments. Within the scope of the technical concept of this application, various simple modifications can be made to the technical solution of this application, and these simple modifications all fall within the protection scope of this application.

Claims

1. An organic compound, characterized in that, The organic compound has the structure shown in Formula I: Formula I Where X is O, S or N (R2), and R2 is selected from aryl groups with 6 to 20 carbon atoms; L, L1, and L2 may be the same or different, and each is independently selected from single bonds, substituted or unsubstituted aryl groups with 6 to 30 carbon atoms, and substituted or unsubstituted heteroaryl groups with 3 to 30 carbon atoms. Ar1 and Ar2 may be the same or different, and each is independently selected from substituted or unsubstituted aryl groups with 6 to 30 carbon atoms, or substituted or unsubstituted heteroaryl groups with 3 to 30 carbon atoms. Each R1 is selected from deuterium, fluorine, cyano, trimethylsilyl, trifluoromethyl, methyl, ethyl, isopropyl, tert-butyl, or phenyl; n1 represents the number of R1s, and n1 can be selected from 0, 1, 2, 3, 4 or 5; The substituents in L, L1, L2, Ar1, and Ar2 may be the same or different, and each is independently selected from deuterium, halogen groups, cyano, alkyl with 1 to 10 carbon atoms, haloalkyl with 1 to 10 carbon atoms, trialkylsilyl with 3 to 12 carbon atoms, aryl with 6 to 20 carbon atoms, or heteroaryl with 3 to 20 carbon atoms; The heteroaryl group refers to a monovalent aromatic ring or its derivative containing at least one heteroatom, wherein the heteroatom is one or more of O, N and S.

2. The organic compound according to claim 1, wherein, R2 is selected from phenyl, naphthyl, or biphenyl.

3. The organic compound according to claim 1, wherein, L, L1, and L2 may be the same or different, and each is independently selected from single bonds, substituted or unsubstituted aryl groups with 6 to 18 carbon atoms, or substituted or unsubstituted heteroaryl groups with 5 to 18 carbon atoms. The substituents in L, L1, and L2 may be the same or different, and each is independently selected from deuterium, fluorine, cyano, trifluoromethyl, trimethylsilyl, alkyl with 1 to 5 carbon atoms, or aryl with 6 to 12 carbon atoms.

4. The organic compound according to claim 1, wherein, L, L1, and L2 may be the same or different, and each is independently selected from single bonds, substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted biphenylene, substituted or unsubstituted dibenzofuranylene, substituted or unsubstituted dibenzothiopheneylene, and substituted or unsubstituted carbazolylene. The substituents in L, L1, and L2 may be the same or different, and each is independently selected from deuterium, fluorine, cyano, trifluoromethyl, trimethylsilyl, methyl, ethyl, isopropyl, tert-butyl, or phenyl.

5. The organic compound according to claim 1, wherein, Ar1 and Ar2 may be the same or different, and each is independently selected from substituted or unsubstituted aryl groups with 6 to 25 carbon atoms, or substituted or unsubstituted heteroaryl groups with 5 to 18 carbon atoms. The substituents in Ar1 and Ar2 may be the same or different, and each is independently selected from deuterium, fluorine, cyano, trimethylsilyl, trifluoromethyl, alkyl with 1 to 5 carbon atoms, aryl with 6 to 12 carbon atoms, or heteroaryl with 3 to 12 carbon atoms.

6. The organic compound according to claim 1, wherein, Ar1 and Ar2 may be the same or different, and each is independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted phenanthyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted triphenylene, substituted or unsubstituted spirofluorene, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted carbazoyl; The substituents in Ar1 and Ar2 may be the same or different, and each is independently selected from deuterium, fluorine, cyano, trimethylsilyl, trifluoromethyl, methyl, ethyl, isopropyl, tert-butyl, phenyl, naphthyl, biphenyl, dibenzofuranyl, dibenzothiophene, or carbazolyl.

7. The organic compound according to claim 1, wherein, Ar1 and Ar2 may be the same or different, and each is 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 includes 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 an organic compound as described in any one of claims 1 to 8.

10. The electronic component according to claim 9, wherein, The functional layer includes a hole transport layer, and the hole transport layer contains the organic compound; The electronic component is an organic electroluminescent device or a photoelectric conversion device; The organic electroluminescent device is a green organic electroluminescent device.

11. An electronic device, characterized in that, The electronic device includes the electronic components as described in claim 9 or 10.

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