Organic Compounds and Electronic Components and Devices Containing the Same

Abstract

This application relates to an organic compound and an electronic component and an electronic device comprising the same. The structural formula of the organic compound of this application comprises the structure shown in Formula I. When the organic compound is applied to an organic electroluminescent device, the performance of the device can be significantly improved.

Description

Technical Field

[0001] This application belongs to the technical field of organic materials, and particularly relates to an organic compound, an electronic component, and an electronic device including the same. Background Art

[0002] Currently, the research on organic electroluminescent materials has been widely carried out in the academic and industrial fields, and a large number of organic electroluminescent materials with excellent performance have been developed one after another. Generally speaking, the future direction of organic electroluminescent devices is to develop white light devices and full-color display devices with high efficiency, long life, and low cost. However, the industrialization process of this technology still faces many key problems. Therefore, designing and finding a stable and efficient compound as a new material for organic electroluminescent devices to overcome the deficiencies that occur in the actual application process is the focus and future research trend of the research work on organic electroluminescent device materials. With the development of electronic technology and the progress of materials science, the application scope of electronic components used to achieve electroluminescence or optoelectronic conversion is becoming more and more extensive. Such electronic components usually include a cathode and an anode arranged opposite to each other, and a functional layer arranged between the cathode and the anode. The functional layer is composed of multiple organic or inorganic film layers, and generally includes an 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] Generally, the stability of electron transport materials is poor and the transport efficiency is low. When used in organic electroluminescent devices, they cannot truly balance the hole and electron transport, resulting in a decrease in the luminous efficiency and a shortening of the lifespan of the device.

[0004] Currently, although a large number of organic electroluminescent materials with excellent performance have been developed one after another, it is still necessary to continue researching and developing new materials to further improve the performance of electronic components. Summary of the Invention

[0005] In view of the above problems existing in the prior art, the purpose of this application is to provide an organic compound, an electronic component, and an electronic device including the same. The organic compound can be used in electronic components to improve the performance of the electronic components.

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

[0007]

[0008] Wherein, X1, X2, and X3 are each independently C(H) or N, and at least one of X1 - X3 is N;

[0009] Ar1 and Ar2 are the same or different, and each independently selected from substituted or unsubstituted aryl groups having 6 to 30 carbon atoms or substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms;

[0010] L, L1 and L2 are the same or different, and each independently selected from a single bond, substituted or unsubstituted arylene groups having 6 to 25 carbon atoms, substituted or unsubstituted heteroarylene groups having 5 to 25 carbon atoms;

[0011] R1 and R2 are the same or different, and each independently selected from deuterium, halogen groups, cyano groups, alkyl groups having 1 to 5 carbon atoms or aryl groups having 6 to 12 carbon atoms; or any two adjacent R1s are connected to form a ring, or any two adjacent R2s are connected to form a ring;

[0012] n1 represents the number of R1s, and is selected from 0, 1, 2, 3 or 4; when n1 is greater than 1, any two R1s are the same or different;

[0013] n2 represents the number of R2s, and is selected from 0, 1, 2, 3 or 4; when n2 is greater than 1, any two R2s are the same or different;

[0014] The substituents in Ar1, Ar2, L, L1 and L2 are the same or different, and each independently selected from deuterium, halogen groups, cyano groups, alkyl groups having 1 to 10 carbon atoms, trialkylsilyl groups having 3 to 12 carbon atoms, deuterated aryl groups having 6 to 12 carbon atoms, aryl groups having 6 to 20 carbon atoms or heteroaryl groups having 3 to 20 carbon atoms; optionally, any two adjacent substituents in Ar1 form a saturated or unsaturated 3- to 15-membered ring; optionally, any two adjacent substituents in Ar2 form a saturated or unsaturated 3- to 15-membered ring.

[0015] The second aspect of the present 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 above-mentioned organic compound.

[0016] The third aspect of the present application provides an electronic device, including the electronic component described in the second aspect.

[0017] The organic compound of the present application uses a specific fused spiro ring structure as the core structure, which has a large conjugated system, and at the same time has relatively high rigidity and high carrier transport efficiency. Further, by introducing a substituted electron-deficient nitrogen-containing six-membered heteroaryl group on one side of the spiro ring structure, the formed organic compound has high electron transport characteristics or hole blocking characteristics. When applied to an organic electroluminescent device, the prepared electroluminescent device can have good optoelectronic properties, improving the luminous efficiency and service life of the device. Description of the Drawings

[0018] The accompanying drawings are used to provide a further understanding of the present application and form 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] Figure 1 It is a schematic structural diagram of an organic electroluminescent device according to an embodiment of the present application.

[0020] Figure 2 It is a schematic diagram of an electronic device according to an embodiment of the present application.

[0021] Reference numerals

[0022] 100, Anode; 200, Cathode; 300, Functional layer; 310, Hole injection layer

[0023] 321, Hole transport layer; 322, Hole auxiliary layer; 330, Organic light-emitting layer; 340, Electron transport layer

[0024] 350, Electron injection layer; 400, Electronic device Specific embodiments

[0025] Exemplary embodiments will now be described more fully with reference to the accompanying drawings. However, the exemplary embodiments can be implemented in various 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 complete and comprehensive, and will fully convey the concept of the exemplary embodiments to those skilled in the art. The features, structures, or characteristics described may be combined in any suitable manner in one or more embodiments. In the following description, numerous specific details are provided to give a thorough understanding of the embodiments of the present application.

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

[0027]

[0028] Wherein, X1, X2, and X3 are each independently C(H) or N, and at least one of X1 - X3 is N;

[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] 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 25 carbon atoms, or a substituted or unsubstituted heteroarylene group having 5 to 25 carbon atoms;

[0031] R1 and R2 are the same or different and are each independently selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 5 carbon atoms, or an aryl group having 6 to 12 carbon atoms; or any two adjacent R1s are connected to form a ring, or any two adjacent R2s are connected to form a ring;

[0032] n1 represents the number of R1s and is selected from 0, 1, 2, 3, or 4; when n1 is greater than 1, any two R1s are the same or different;

[0033] n2 represents the number of R2s and is selected from 0, 1, 2, 3, or 4; when n2 is greater than 1, any two R2s are the same or different;

[0034] The substituents in Ar1, Ar2, L, L1, and L2 are the same or different and are each independently selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 10 carbon atoms, a trialkylsilyl group having 3 to 12 carbon atoms, a deuterated aryl group having 6 to 12 carbon atoms, an aryl group having 6 to 20 carbon atoms, or a heteroaryl group having 3 to 20 carbon atoms; optionally, any two adjacent substituents in Ar1 form a saturated or unsaturated 3- to 15-membered ring; optionally, any two adjacent substituents in Ar2 form a saturated or unsaturated 3- to 15-membered ring.

[0035] In this application, the terms "optionally" and "optionally" mean that the subsequent described event or circumstance may or may not occur. For example, "optionally, any two adjacent substituents form a saturated or unsaturated 3- to 15-membered ring" includes both the scenario where any two adjacent substituents form a ring and the scenario where any two adjacent substituents exist independently of each other and do not form a ring. "Any two adjacent" can include having two substituents on the same atom and can also include having one substituent on each of two adjacent atoms; wherein, when there are two substituents on the same atom, the two substituents can form a saturated or unsaturated spiro ring with the atom to which they are commonly attached; when there is one substituent on each of two adjacent atoms, the two substituents can be fused into a ring.

[0036] In this application, the description mode "each... independently is", "respectively independently is", and "each independently is" can be interchanged and should be understood in a broad sense. It can either mean that among different groups, the specific options represented by the same symbol do not affect each other, or it can also mean that among the same group, the specific options represented by the same symbol 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, chlorine, which means that: 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 each benzene ring of biphenyl has q substituents R”, and the number q of R” substituents on the two benzene rings can be the same or different, and each R” can be the same or different, and the options of each R” do not affect each other.

[0037] In the present application, the term "substituted or unsubstituted" means that the functional group described after this term may or may not have a substituent (hereinafter, for the sake of convenience of description, the substituent is collectively referred to as Rc). For example, "substituted or unsubstituted aryl" means an aryl having a substituent Rc or an aryl without a substituent. Among them, the above-mentioned substituent, namely Rc, can be, for example, deuterium, a halogen group, a cyano group, a heteroaryl group, an aryl group, a trialkylsilyl group, an alkyl group, a haloalkyl group, a cycloalkyl group, etc. The number of substituents can be 1 or more.

[0038] In the present application, "a plurality of" means more than 2, such as 2, 3, 4, 5, 6, etc.

[0039] In the present application, the number of carbon atoms of a substituted or unsubstituted functional group refers to all carbon atoms.

[0040] The hydrogen atoms in the compound structure of the present application include various isotope atoms of hydrogen element, such as hydrogen (H), deuterium (D), or tritium (T).

[0041] "D" in the chemical formula of the compound of the present application represents deuteration.

[0042] In the present application, "aryl" refers to an optionally functionalized or substituted group derived from an aromatic carbocyclic ring. An aryl group can be a monocyclic aryl group (such as phenyl) or a polycyclic aryl group. In other words, an aryl group can be a monocyclic aryl group, a fused-ring aryl group, two or more monocyclic aryl groups conjugated through carbon-carbon bonds, a monocyclic aryl group and a fused-ring aryl group conjugated through carbon-carbon bonds, or two or more fused-ring aryl groups connected through carbon-carbon bonds. That is, unless otherwise specified, two or more aromatic groups connected through carbon-carbon bonds can also be regarded as the aryl groups of the present application. Among them, the fused-ring aryl group can include, for example, a bicyclic fused aryl group (such as naphthyl), a tricyclic fused aryl group (such as phenanthryl, fluorenyl, anthryl), etc. Examples of aryl groups include, but are not limited to, phenyl, naphthyl, fluorenyl, spirobifluorenyl, anthryl, phenanthryl, biphenyl, terphenyl, triphenylene, perylenyl, benzo[9,10]phenanthryl, pyrenyl, benzo[a]pyrenyl, and the like.

[0043] In the present application, "arylene" refers to a divalent group formed by an aryl group losing one or more hydrogen atoms.

[0044] In the present application, the terphenyl includes

[0045] In the present application, the number of carbon atoms of the substituted or unsubstituted aryl (arylene) can be 6, 8, 10, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 30. In some embodiments, the substituted or unsubstituted aryl is a substituted or unsubstituted aryl having 6 to 30 carbon atoms. In some other embodiments, the substituted or unsubstituted aryl is a substituted or unsubstituted aryl having 6 - 25 carbon atoms. In some other embodiments, the substituted or unsubstituted aryl is a substituted or unsubstituted aryl having 6 - 18 carbon atoms. In some other embodiments, the substituted or unsubstituted aryl is a substituted or unsubstituted aryl having 6 - 15 carbon atoms.

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

[0047] In the present application, the aryl as the substituent of L, L1, L2, Ar1 and Ar2 is, for example but not limited to, phenyl, naphthyl, phenanthryl, biphenyl, fluorenyl, dimethylfluorenyl, and the like.

[0048] In the present application, the heteroaryl refers to a monovalent aromatic ring or its derivative containing 1, 2, 3, 4, 5 or 6 heteroatoms in the ring, and the heteroatoms can be one or more of B, O, N, P, Si, Se and S. The heteroaryl can be a monocyclic heteroaryl or a polycyclic heteroaryl. In other words, the heteroaryl can be a single aromatic ring system, or a plurality of aromatic ring systems conjugated through carbon-carbon bonds, and any aromatic ring system is an aromatic monocyclic ring or an aromatic fused ring. Exemplarily, the heteroaryl can include thiophenyl, furyl, pyrrolyl, imidazolyl, thiazolyl, oxazolyl, oxadiazolyl, triazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, acridinyl, pyridazinyl, pyrazinyl, quinolinyl, quinazolinyl, quinoxalinyl, phenoxazinyl, phthalazinyl, pyridinopyrimidinyl, pyridinopyrazinyl, pyrazinopyrazinyl, isoquinolinyl, indolyl, carbazolyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothiophenyl, dibenzothiophenyl, thienothiophenyl, benzofuryl, phenanthrolinyl, isoxazolyl, thiadiazolyl, phenothiazinyl, silafluorenyl, dibenzofuryl, and N-phenylcarbazolyl, N-pyridylcarbazolyl, N-methylcarbazolyl, etc., and is not limited thereto.

[0049] In the present application, the heteroarylene involved refers to a divalent or polyvalent group formed by the heteroaryl further losing one or more hydrogen atoms.

[0050] In the present application, the number of carbon atoms of the substituted or unsubstituted heteroaryl (heteroarylene) can be selected from 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30. In some embodiments, the substituted or unsubstituted heteroaryl is a substituted or unsubstituted heteroaryl having a total of 12 to 18 carbon atoms. In other embodiments, the substituted or unsubstituted heteroaryl is a substituted or unsubstituted heteroaryl having a total of 5 to 12 carbon atoms.

[0051] In the present application, heteroaryl as a substituent of L, L1, L2, Ar1 and Ar2 includes, for example but not limited to, pyridyl, carbazolyl, dibenzothienyl, dibenzofuranyl, benzoxazolyl, benzothiazolyl, benzimidazolyl.

[0052] In the present application, the substituted heteroaryl may be one or more hydrogen atoms in the heteroaryl substituted by groups such as deuterium atoms, halogen groups, -CN, aryl, heteroaryl, trialkylsilyl, alkyl, cycloalkyl, haloalkyl, etc.

[0053] In the present application, the alkyl having 1 to 10 carbon atoms may include a straight-chain alkyl having 1 to 10 carbon atoms and a branched-chain alkyl having 3 to 10 carbon atoms. The number of carbon atoms of the alkyl may be, for example, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10. Specific examples of the alkyl include but are not limited to, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl, neopentyl, n-hexyl, etc.

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

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

[0056] In the present application, specific examples of the deuterated aryl include but are not limited to, deuterated phenyl.

[0057] In the present application, a ring system formed by n atoms is an n-membered ring. For example, phenyl is a 6-membered ring. The 3- to 15-membered ring refers to a cyclic group having 3 to 15 ring atoms. The 3- to 15-membered ring is, for example, cyclopentane, cyclohexane, fluorene ring, benzene ring, etc.

[0058] In the present application, refers to a chemical bond connecting to other groups.

[0059] In the present application, the single bond extending from the ring system involved in the non-positioning connecting bond It means that one end of the linking bond can be linked to any position in the ring system penetrated by the bond, and the other end is linked to the rest of the compound molecule. For example, as shown in the following formula (f), the naphthyl group represented by formula (f) is linked to other positions of the molecule through two non-positioning linking bonds penetrating the bicyclic ring, and the meaning it represents includes any possible linking mode shown in formulas (f-1) - (f-10).

[0060]

[0061] For another example, as shown in the following formula (X'), the dibenzofuranyl group represented by formula (X') is linked to other positions of the molecule through a non-positioning linking bond extending from the middle of one benzene ring, and the meaning it represents includes any possible linking mode shown in formulas (X'-1) - (X'-4).

[0062]

[0063] The non-positioning substituent in this application refers to a substituent linked by a single bond extending from the center of the ring system, which means that the substituent can be linked to any possible position in the ring system. For example, as shown in the following formula (Y), the substituent R' represented by formula (Y) is linked to the quinoline ring through a non-positioning linking bond, and the meaning it represents includes any possible linking mode shown in formulas (Y-1) - (Y-7).

[0064]

[0065] Optionally, two or three of X1 - X3 are N.

[0066] Optionally, X1 is selected from N, X2 is selected from C or N, and X3 is selected from N.

[0067] Optionally, X1 is selected from N, X3 is selected from C or N, and X2 is selected from N.

[0068] Optionally, formula I is selected from the structures shown in the following formulas I-1 to I-3:

[0069]

[0070] Optionally, formula I is selected from the structures shown in the following formulas I-a to I-l:

[0071]

[0072] In one embodiment of this application, R1, R2, and R3 are each independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, or phenyl.

[0073] In one embodiment of the present application, Ar1 and Ar2 are the same or different and are each independently selected from substituted or unsubstituted aryl groups having 6 to 25 carbon atoms or substituted or unsubstituted heteroaryl groups having 12 to 18 carbon atoms.

[0074] Optionally, the substituents in Ar1 and Ar2 are each independently selected from deuterium, fluorine, cyano, alkyl groups having 1 to 5 carbon atoms, trimethylsilyl, deuterated phenyl, aryl groups having 6 to 12 carbon atoms, or heteroaryl groups having 12 to 18 carbon atoms; optionally, in Ar1 and Ar2, any two adjacent substituents form a 5- to 13-membered ring.

[0075] Optionally, Ar1 and Ar2 are each independently selected from substituted or unsubstituted group W, where the unsubstituted group W is selected from the following groups:

[0076]

[0077] Among them, the substituted group W has one or more than two substituents, and the substituents are each independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trimethylsilyl, deuterated phenyl, phenyl, naphthyl, biphenyl, dibenzofuranyl, or dibenzothiophenyl.

[0078] Optionally, Ar1 and Ar2 are each independently selected from the group consisting of the following groups:

[0079]

[0080] Further optionally, Ar1 and Ar2 are each independently selected from the following groups:

[0081]

[0082]

[0083] In some embodiments, L, L1, and L2 are the same or different and are each independently selected from a single bond, substituted or unsubstituted arylene groups having 6 to 14 carbon atoms, or substituted or unsubstituted heteroarylene groups having 5 to 18 carbon atoms. For example, L, L1, and L2 are each independently selected from a single bond, substituted or unsubstituted arylene groups having 6, 7, 8, 9, 10, 11, 12, 13, or 14 carbon atoms, and substituted or unsubstituted heteroarylene groups having 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, or 18 carbon atoms.

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

[0085] In some embodiments, L, L1, and L2 are the same or different and are each independently selected from a single bond, a substituted or unsubstituted phenylene, a substituted or unsubstituted naphthylene, a substituted or unsubstituted biphenylene, a substituted or unsubstituted phenanthrylene, a substituted or unsubstituted anthrylene, a substituted or unsubstituted fluorenylene, a substituted or unsubstituted carbazolylene, a substituted or unsubstituted dibenzothiophenylene, or a substituted or unsubstituted dibenzofuranylene.

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

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

[0088]

[0089]

[0090] In some embodiments, L, L1, and L2 are each independently selected from a single bond or the group consisting of the following groups:

[0091]

[0092] In some embodiments, each is independently selected from the group consisting of the following groups:

[0093]

[0094]

[0095] Optionally, the organic compound is selected from the group consisting of the following compounds.

[0096]

[0097]

[0098]

[0099]

[0100]

[0101]

[0102]

[0103]

[0104]

[0105]

[0106]

[0107] In a second aspect, the present application provides an organic electroluminescent device, comprising an anode, a cathode, and a functional layer disposed between the anode and the cathode; wherein the functional layer contains the organic compound described in the present application.

[0108] Optionally, the electronic component is an organic electroluminescent device.

[0109] In an embodiment of the present application, the structure of the organic electroluminescent device is as Figure 1 shown, comprising an anode 100 and a cathode 200 disposed opposite to each other, and a functional layer 300 disposed between the anode 100 and the cathode 200; the functional layer 300 includes an electron transport layer 340, and the electron transport layer 340 contains the organic compound described in the present application.

[0110] Optionally, the functional layer 300 includes a hole transport layer 321, and the hole transport layer is located between the anode and the organic light-emitting layer. The hole transport material can be selected from triarylamine compounds or other types of compounds, and those skilled in the art can refer to the prior art for selection. For example, the material of the hole transport layer 321 is selected from the group consisting of the following compounds.

[0111]

[0112] In an embodiment of the present application, the material of the hole transport layer 321 contains NPB.

[0113] In an embodiment of the present application, the organic electroluminescent device may include an anode 100, a hole transport layer 321, a hole auxiliary layer 322, an organic electroluminescent layer 330 as an energy conversion layer, an electron transport layer 340, and a cathode 200 stacked in sequence.

[0114] In this application, the anode 100 includes an anode material, which may optionally be a material with a large work function (work function) that helps hole injection into the functional layer. Specific examples of anode materials include: metals such as nickel, platinum, vanadium, chromium, copper, zinc, and gold, or their alloys; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); combinations of metals and oxides such as ZnO:Al or SnO2:Sb; or conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylenedioxy)thiophene] (PEDT), polypyrrole, and polyaniline, but not limited thereto. Optionally, a transparent electrode including indium tin oxide (ITO) as the anode is included.

[0115] Optionally, a hole injection layer 310 is further provided between the anode 100 and the hole transport layer 321 to enhance the ability to inject holes into the hole transport layer 321. The hole injection layer 310 can be selected from benzidine derivatives, starburst arylamine compounds, phthalocyanine derivatives, or other materials, and this application does not make special restrictions thereon. The material of the hole injection layer 310 is, for example, selected from the following compounds or any combination thereof;

[0116]

[0117]

[0118] In one embodiment of this application, the hole injection layer 310 is composed of HAT-CN.

[0119] Optionally, the electron blocking layer 322 includes one or more electron blocking materials, and the electron blocking materials can be selected from carbazole polymers or other types of compounds, and this application does not make special limitations thereon. For example, in some embodiments of this application, the electron blocking layer 322 is composed of the compound EB-1 composed.

[0120] Optionally, the organic light-emitting layer 330 can be composed of a single light-emitting material or can 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. The holes injected into the organic light-emitting layer 330 and the 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.

[0121] The host material of the organic light-emitting layer 330 may include metal chelate compounds, distyryl derivatives, aromatic amine derivatives, dibenzofuran derivatives, or other types of materials. The host material of the organic light-emitting layer 330 may be a single compound or a combination of two or more compounds.

[0122] In one embodiment of the present application, the host material of the organic light-emitting layer 330 is BH-1

[0123] The guest material of the organic light-emitting layer 330 may be a compound having a condensed aryl ring or a derivative thereof, a compound having a heteroaryl ring or a derivative thereof, an aromatic amine derivative, or other materials, and the present application does not impose special restrictions thereon. The guest material is also referred to as a doping material or a dopant. Specific examples of the dopant include, but are not limited to,

[0124]

[0125]

[0126] In some specific embodiments of the present application, the guest material of the organic light-emitting layer 330 is BD-1.

[0127] In the present application, the cathode 200 includes a cathode material, which is a material with a small work function that helps electron injection into the functional layer. Specific examples of the cathode material include, but are not limited to, metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof; or multilayer materials such as LiF / Al, Liq / Al, LiO2 / Al, LiF / Ca, LiF / Al, and BaF2 / Ca. Optionally, a metal electrode containing magnesium and silver is included as the cathode.

[0128] Optionally, an electron injection layer 350 is further provided between the cathode 200 and the electron transport layer 340 to enhance the ability to inject electrons into the electron transport layer 340. The electron injection layer 350 may include inorganic materials such as alkali metal sulfides and alkali metal halides, or may include a complex of an alkali metal and an organic compound. In one embodiment of the present application, the electron injection layer 350 includes Yb.

[0129] The third aspect of the present application provides an electronic device including the electronic component described in the second aspect of the present application.

[0130] According to one embodiment, as Figure 2As shown, the provided electronic device is the electronic device 400, which includes the above-mentioned organic electroluminescent device. The electronic device 400 can be, for example, a display device, a lighting device, an optical communication device, or other types of electronic devices, and can include, for example, but not limited to, a computer screen, a mobile phone screen, a television, an electronic paper, an emergency lighting lamp, an optical module, etc.

[0131] The synthesis method of the organic compound of the present application will be specifically described below in combination with the synthesis examples, but the present application is not limited thereby.

[0132] Synthesis Example

[0133] I. Synthesis of Intermediate

[0134] 1. Synthesis of Intermediate IM a1-dX

[0135] Taking IM a1-d1 as an example to illustrate the synthesis of IM a1-dX:

[0136]

[0137] (1) Add 1,8-dilithionaphthalene (120 g, 856.90 mmol) and diethyl ether into a three-necked flask, cool the system to -10°C to 10°C, add dichlorobis(triphenylphosphine)rhodium(I) dimer (333.14 g, 856.90 mmol), react at -10°C to 10°C for 2 h and then naturally rise to room temperature and react for 6 h. After extracting the reaction solution with ethyl acetate and water, the organic phase is dried with anhydrous magnesium sulfate. After concentrating the organic layer under reduced pressure, a crude product is obtained. Then, the crude product is crystallized with dichloromethane / n-heptane to obtain a white solid IM a1-a0 (37.5 g, yield 31.0%).

[0138]

[0139] (2) Add 2-bromo-4-chloroiodobenzene (80.00 g, 252.09 mmol), phenylboronic acid (30.74 g, 252.09 mmol), potassium carbonate (69.68 g, 504.18 mmol), tetrabutylammonium bromide (8.13 g, 25.21 mmol), toluene (400 mL), ethanol (240 mL) and deionized water (160 mL) into a three-necked flask, stir under nitrogen protection for 15 min, add tetrakis(triphenylphosphine)palladium( ) (2.91 g, 2.52 mmol) and heat to 75°C - 80°C, stir for 24 hours; after cooling the reaction solution to room temperature, wash it with water several times until neutral and then dry it with anhydrous magnesium sulfate. Remove the solvent from the organic phase under reduced pressure, and then recrystallize with dichloromethane / n-heptane to obtain a white solid IM a1-a1 (35.6 g, yield 52.8%).

[0140]

[0141] (3) IM a1-a1 (34.0 g, 127.08 mmol) and THF (204 mL) were added to a 500 mL round-bottom flask. The system was cooled to -90 °C to -78 °C, and a solution of n-butyllithium (2 mol / L; 76.25 mL, 152.50 mmol) in THF was added dropwise. The reaction was carried out at -90 °C to -78 °C for 1 h. Then, IM a1-a0 (35.62 g, 127.08 mmol) was dissolved in THF (142 mL) and slowly added dropwise to the reaction system. The reaction was carried out at -78 °C to -90 °C for 1 h, and then naturally warmed to room temperature and stirred for 6 h. Water (200 mL) was added to the reaction system to terminate the reaction, and extraction was carried out with ethyl acetate and water. The organic layer was concentrated under reduced pressure to obtain a crude product, and the crude product was recrystallized with acetonitrile to obtain IM a1-b1 (33.5 g, yield 56.2%).

[0142]

[0143] (4) IM a1-b1 (33.0 g, 70.37 mmol), acetic acid (330 mL), and sulfuric acid (98 wt%, 1 mL) were placed in a 500 mL round-bottom flask and heated to 75 °C for 3 h. As the reaction proceeded, a solid precipitated. After the reaction was completed, the system was cooled to room temperature, and then filtered. The filter cake was washed with water and ethanol several times to obtain a crude product, and the crude product was crystallized with dichloromethane / n-heptane to obtain IM a1-c1 (29.3 g, yield 92.3%).

[0144]

[0145] (5) IM a1-c1 (29.0 g, 64.31 mmol), bis(pinacolato)diboron (16.33 g, 64.31 mmol), tris(dibenzylideneacetone)dipalladium (0.64 g, 0.59 mmol), 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl (0.61 g, 1.29 mmol), potassium acetate (12.62 g, 128.61 mmol), and 1,4-dioxane (290 mL) were added to a three-necked round-bottom flask. Under nitrogen protection, the mixture was heated to 80 °C and stirred for 4 h. Then, it was cooled to room temperature. The reaction solution was washed with water and dried with magnesium sulfate, and the solvent was removed under reduced pressure after filtration. The crude product was recrystallized and purified using a toluene system to obtain solid IM a1-d1 (26.1 g, yield 74.8%).

[0146] Other IM a1-dX listed in Table 1 were synthesized by referring to the synthesis method of IM a1-d1, except that raw material 1 was used instead of 2-bromo-4-chloroiodobenzene in step (2), raw material 2 was used instead of phenylboronic acid in step (2), and raw material 3 was used instead of IM a1-a1 in step (3). The main raw materials used, the synthesis of IM a1-dX, and the yield of the last step are shown in Table 1.

[0147] Table 1

[0148]

[0149]

[0150] 2. Synthesis of intermediate IM a1-d-bX

[0151] Taking IM a1-d-b1 as an example to illustrate the synthesis of IM a1-d-bX:

[0152]

[0153] (1) Add IM a1-d1 (5.50 g, 10.14 mmol), 4-chlorobromobenzene (1.94 g, 10.14 mmol), potassium carbonate (2.80 g, 20.28 mmol), tetrabutylammonium bromide (0.65 g, 2.03 mmol), toluene (45 mL), ethanol (15 mL), and deionized water (15 mL) into a three-necked flask. After stirring for 15 min under nitrogen protection, add tetrakis(triphenylphosphine)palladium (0.12 g, 0.10 mmol) and heat up to 75 °C - 80 °C, then stir for 6 h. After cooling the reaction solution to room temperature, wash it with water several times until neutral, and then dry it with anhydrous magnesium sulfate. Remove the solvent from the organic phase under reduced pressure, and recrystallize it with dichloromethane / n-heptane to obtain a white solid, namely IM a1-d-a1 (3.65 g, yield 68.3%).

[0154]

[0155] (2) IM a1-d-a1 (3.5 g, 6.64 mmol), bis(pinacolato)diboron (1.69 g, 6.64 mmol), tris(dibenzylideneacetone)dipalladium(0) (0.06 g, 0.07 mmol), 2-(dicyclohexylphosphino)-2′,4′,6′-triisopropylbiphenyl (0.06 g, 0.13 mmol), potassium acetate (1.30 g, 13.28 mmol) and 1,4-dioxane (40 mL) were added to a three-necked round-bottom flask. The mixture was heated to 80 °C under nitrogen protection and stirred for 4 h. Then it was cooled to room temperature. The reaction solution was washed with water and dried over magnesium sulfate. After filtration, the solvent was removed under reduced pressure. The crude product was recrystallized and purified using a toluene system to obtain solid IM a1-d-b1 (2.85 g, yield 69.4%).

[0156] Other IM a1-d-bX were synthesized by referring to the synthesis method of IM a1-d-b1, except that raw material 4 was used instead of IM a1-dX in step (1), and raw material 5 was used instead of 4-chlorobromobenzene. The main raw materials used, the synthesized IM a1-d-bX, and the yield of the last step are shown in Table 2.

[0157] Table 2

[0158]

[0159]

[0160] 3. Synthesis of intermediate IM a1-X

[0161] Taking IM a1-1 as an example to illustrate the synthesis of IM a1-X

[0162]

[0163] IM a1-d1 (20.00 g, 36.87 mmol), cyanuric chloride (6.80 g, 36.87 mmol), potassium carbonate (10.19 g, 73.73 mmol), tetrabutylammonium bromide (1.19 g, 3.69 mmol), toluene (104 mL), ethanol (26 mL) and deionized water (26 mL) were added to a three-necked flask. After stirring for 15 min under nitrogen protection, tetrakis(triphenylphosphine)palladium(0) (0.43 g, 0.37 mmol) was added and the temperature was raised to 75 °C - 80 °C, and then stirred for 5 h. After the reaction solution was cooled to room temperature, it was washed with water several times until neutral and then dried over anhydrous magnesium sulfate. The organic phase was concentrated under reduced pressure to remove the solvent, and then recrystallized with dichloroethane / n-heptane to obtain white solid IM a1-1 (12.15 g, yield 58.4%).

[0164] Other IM a1-X was synthesized according to the synthesis method of IM a1-1, except that raw material 5 was used instead of IM a1-d1. Raw material 5, IM a1-X and their yields are shown in Table 3.

[0165] Table 3

[0166]

[0167]

[0168]

[0169]

[0170] Synthesis of Compounds

[0171] Synthesis Example 1: Synthesis of Compound 1-1

[0172]

[0173] (1) Add IM a1-1 (12 g, 21.26 mmol), 4-fluorophenylboronic acid (1.89 g, 21.26 mmol), potassium carbonate (5.88 g, 42.52 mmol), tetrabutylammonium bromide (0.69 g, 2.13 mmol), toluene (64 mL), ethanol (24 mL) and deionized water (24 mL) into a three-necked flask. After stirring for 15 min under nitrogen protection, add tetrakis(triphenylphosphine)palladium (0.25 g, 0.21 mmol) and heat up to 75 °C - 80 °C, then stir for 8 hours. After cooling the reaction solution to room temperature, wash it with water several times until neutral, then dry it with anhydrous magnesium sulfate. Remove the solvent from the organic phase under reduced pressure, and recrystallize with dichloromethane / n-heptane to obtain a white solid IMA1-a1 (8.2 g, yield 61.8%).

[0174]

[0175] (2) IMA1-a1 (8.0 g, 12.82 mmol), 4-fluorobenzeneboronic acid (1.79 g, 12.82 mmol), potassium carbonate (3.54 g, 25.64 mmol), tetrabutylammonium bromide (0.41 g, 1.28 mmol), toluene (64 mL), ethanol (16 mL) and deionized water (16 mL) were added to a three-necked flask. After stirring for 15 min under nitrogen protection, tetrakis(triphenylphosphine)palladium (0.15 g, 0.13 mmol) was added and the temperature was raised to 75 °C - 80 °C, and then stirred for 12 hours. After the reaction solution was cooled to room temperature, it was washed with water several times until neutral and then dried with anhydrous magnesium sulfate. The organic phase was concentrated under reduced pressure to remove the solvent, and then triturated with toluene to obtain a white solid, namely compound 1-1 (5.6 g, yield 63.9%). Mass spectrum: m / z = 684.2 [M+H] + ;

[0176] The compounds listed in Table 4 were synthesized by referring to the method of compound 1-1, except that raw material 6 was used instead of IMA1-1 in step (1), raw material 7 was used instead of 4-fluorobenzeneboronic acid in step (1), and raw material 8 was used instead of 4-fluorobenzeneboronic acid in step (2). The main raw materials used, the synthesized compounds, their final step yields and mass spectrum results are shown in Table 4.

[0177] Table 4

[0178]

[0179]

[0180]

[0181]

[0182]

[0183]

[0184] The NMR data of the compounds are shown in Table 5:

[0185] Table 5

[0186]

[0187] Example 1

[0188] This example provides an organic electroluminescent device, and the specific preparation method is as follows:

[0189] The anode was prepared through the following process: A three-layer material of ITO / Ag / ITO was plated (with a thickness of The ITO substrate is cut into a size of 40 mm (length) × 40 mm (width) × 0.7 mm (thickness). Using the photolithography process, it is fabricated into an experimental substrate with cathode, anode, and insulating layer patterns. Surface treatment can be carried out using ultraviolet ozone and O2:N2 plasma to increase the work function of the anode, and the surface of the ITO substrate can be cleaned with organic solvents to remove impurities and oil stains on the surface of the ITO substrate.

[0190] HAT-CN is vacuum-evaporated on the experimental substrate (anode) to form a hole injection layer (HIL) with a thickness of Then, NPB is vacuum-evaporated on the hole injection layer to form a hole transport layer with a thickness of

[0191] EB-1 is vacuum-evaporated on the hole transport layer to form an electron blocking layer with a thickness of

[0192] Next, on the electron blocking layer, the compound BH-1 (doping host) and the compound BD-1 (doping guest) are co-evaporated at a ratio of 98%:2% to form a light-emitting layer (EML) with a thickness of

[0193] On the light-emitting layer, the compound 1-1 and LiQ are mixed and evaporated at a thickness ratio of 1:1 to form an electron transport layer (ETL) with a thickness of Yb is evaporated on the electron transport layer to form an electron injection layer (EIL) with a thickness of Then, magnesium (Mg) and silver (Ag) are mixed at an evaporation rate ratio of 1:10 and vacuum-evaporated on the electron injection layer to form a cathode with a thickness of

[0194] In addition, CP-1 with a thickness of is vacuum-evaporated on the above-mentioned cathode, thus completing the fabrication of the green organic electroluminescent device.

[0195] Examples 2 - 35:

[0196] Except that when preparing the electron transport layer, the compound in Table 1 is used to replace compound 1-1 in Example 1, the organic electroluminescent device is prepared using the same method as in Example 1.

[0197] Comparative Examples 1 - 3

[0198] Except that when preparing the electron transport layer, the compound in Table 1 is used to replace compound 1-1 in Example 1, the organic electroluminescent device is prepared using the same method as in Example 1.

[0199] ​​​​Among them, when preparing the organic electroluminescent device, the structures of the various materials used in the comparative examples and the examples are as follows:

[0200] The main material structures used in the above examples and comparative examples are shown in Table 6.

[0201] Table 6

[0202]

[0203]

[0204] The performance of the green organic electroluminescent devices prepared in Examples 1-35 and Comparative Examples 1-3 was tested. Specifically, the IVL data (operating voltage, external quantum efficiency, color coordinates) of the devices were tested under the condition of 10 mA / cm 2 . The T 95 lifetime was tested under the condition of 15 mA / cm 2 . The test results are shown in Table 7 below.

[0205] Table 7 Test Results of the Performance of Blue Organic Electroluminescent Devices

[0206]

[0207]

[0208] Referring to Table 7 above, compared with the organic electroluminescent devices of Comparative Examples 1-3, the performance of the organic electroluminescent devices of Examples 1-35 has been greatly improved. The main manifestations are that the operating voltage of the device has decreased slightly, the external quantum efficiency has increased by at least 15.7%, and the T 95 lifetime has increased by at least 16.9%. It can be seen that using the organic compound of the present application in the electron transport layer of the organic electroluminescent device can significantly improve the external quantum efficiency and T 95 lifetime of the organic electroluminescent device.

[0209] The preferred embodiments of the present application have been described in detail above. However, the present application is not limited to the specific details in the above embodiments. Within the scope of the technical concept of the present application, various simple modifications can be made to the technical solutions of the present application, and these simple modifications all belong to the protection scope of the present application.

Claims

1. An organic compound, characterized in that, The organic compound has a structure represented by Formula I-1: Wherein, Ar1 and Ar2 are the same or different, and each independently selected from a substituted or unsubstituted group W, and the unsubstituted group W is selected from the following groups: Wherein, the substituted group W has one or more substituents, and each of the substituents is independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trimethylsilyl, deuterated phenyl, phenyl, naphthyl or biphenyl; L, L1 and L2 are the same or different, and each independently selected from a single bond, a substituted or unsubstituted phenylene, a substituted or unsubstituted naphthylene, a substituted or unsubstituted biphenylene, a substituted or unsubstituted fluorenylene, a substituted or unsubstituted carbazolylene, a substituted or unsubstituted dibenzothiophenylene, a substituted or unsubstituted dibenzofuranylene; The substituents in L, L1 and L2 are the same or different, and each independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trimethylsilyl, deuterated phenyl, phenyl or naphthyl; R1 and R2 are the same or different, and each independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl or phenyl; n1 represents the number of R1, and is selected from 0, 1, 2, 3 or 4; when n1 is greater than 1, any two R1 are the same or different; n2 represents the number of R2, and is selected from 0, 1, 2, 3 or 4; when n2 is greater than 1, any two R2 are the same or different.

2. The organic compound according to claim 1, each independently selected from the group consisting of the following groups:

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

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

5. The electronic component according to claim 4, characterized in that, The electronic component is an organic electroluminescent device.

6. An electronic device, characterized in that, Including the electronic component according to claim 4 or 5.

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