Organic compound, and electronic element and electronic device using same

Abstract

The present invention relates to an organic compound, and an electronic element and an electronic device using the same. The organic compound has a structure as shown in a formula 1, and when the organic compound is applied to an organic electroluminescent device, the performance of the device can be remarkably improved. # imgabs0 #

Description

Technical Field

[0001] The present application relates to the field of organic electroluminescence, and specifically, to an organic compound, an electronic component, and an electronic device using the same. Background Art

[0002] With the development of electronic technology and the progress of material science, the application scope of electronic components for realizing electroluminescence or photoelectric conversion is becoming more and more extensive. Such electronic components generally include a cathode and an anode disposed opposite to each other, and a functional layer disposed 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] Taking an organic electroluminescent device as an example, it generally includes an anode, a hole transport layer, an electroluminescent layer as an energy conversion layer, an electron transport layer, and a cathode stacked in sequence. When a voltage is applied between the two electrodes, an electric field is generated between the two electrodes. Under the action of the electric field, electrons on the cathode side move towards the electroluminescent layer, and holes on the anode side also move towards the light-emitting layer. The electrons and holes combine in the electroluminescent layer to form excitons. The excitons are in an excited state and release energy outward, thereby causing the electroluminescent layer to emit light externally. Summary of the Invention

[0004] The purpose of the present application is to provide an organic compound, an electronic component, and an electronic device using the same. Using the organic compound in an organic electroluminescent device can improve the performance of the device.

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

[0006]

[0007] Wherein, Ar is selected from phenyl, naphthyl or biphenyl;

[0008] R1, R2, R3 and R4 are the same or different, and each independently is 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 alkyl group having 1 to 10 carbon atoms, a halogenated alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 12 carbon atoms or a heteroaryl group having 3 to 12 carbon atoms;

[0009] n1 is the number of R1, and n1 is selected from 0, 1, 2, 3 or 4. When n1 is greater than 1, any two R1 are the same or different;

[0010] n2 is the number of R2, and n2 is selected from 0, 1, 2, 3 or 4. When n2 is greater than 1, any two R2 are the same or different;

[0011] n3 is the number of R3, and n3 is selected from 0, 1, 2, 3 or 4. When n3 is greater than 1, any two R3s can be the same or different;

[0012] n4 is the number of R4, and n4 is selected from 0, 1, 2, 3 or 4. When n4 is greater than 1, any two R4s can be the same or different;

[0013] Ar1 and Ar2 are the same or different, and 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 20 carbon atoms;

[0014] L, L1 and L2 are the same or different, and each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms;

[0015] The substituents in Ar1, Ar2, L, L1 and L2 are the same or different, and each independently selected from deuterium, a halogen group, a cyano group, a trialkylsilyl group having 3 to 12 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 12 carbon atoms or a heteroaryl group having 3 to 12 carbon atoms.

[0016] The second aspect of the present application provides an electronic component, including an anode and a cathode arranged oppositely, and a functional layer disposed between the anode and the cathode; the functional layer contains the above-mentioned organic compound.

[0017] The third aspect of the present application provides an electronic device, including the electronic component described in the second aspect of the present application.

[0018] The compound of the present application is a compound formed by taking indolo-spirofluorene substituted with a simple aryl group as the mother nucleus and bonding a triarylamine to the mother nucleus at any position. On the one hand, indolo-spirofluorene has a central carbon, which provides steric hindrance for the entire molecular structure, prevents face-to-face stacking, reduces the possibility of molecular crystallization, increases the stability of the molecular structure, thereby improving the lifetime of the device. And indole is fused with spirofluorene, increasing the electron cloud density of the entire mother nucleus and improving the hole transport ability. On the other hand, after the mother nucleus is bonded to the triarylamine, a strong conjugation effect can be generated, enhancing the local electron cloud density, enabling the material to maintain a high hole mobility while having a relatively deep HOMO energy level, thereby improving the light-emitting efficiency of the device. Using this material in the hole transport layer of an organic electroluminescent device can effectively enhance the device efficiency and improve the device lifetime.

[0019] Other features and advantages of the present application will be described in detail in the subsequent specific implementation section. Description of the Drawings

[0020] 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 detailed description, they are used to explain the present application, but do not constitute a limitation to the present application.

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

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

[0023] Figure 3 It is a schematic structural diagram of a photoelectric conversion device according to an embodiment of the present application.

[0024] Figure 4 It is a schematic diagram of a second electronic device according to an embodiment of the present application.

[0025] Description of the reference numerals

[0026] 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, hole blocking layer; 350, electron transport layer; 360, electron injection layer; 370, photoelectric conversion layer; 400, first electronic device; 500, second electronic device. Detailed description

[0027] 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 described features, structures, or characteristics can 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.

[0028] In a first aspect, the present application provides an organic compound having a structure represented by Formula 1:

[0029]

[0030] Wherein, Ar is selected from phenyl, naphthyl or biphenyl;

[0031] R1, R2, R3 and R4 are the same or different and 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 alkyl group having 1 to 10 carbon atoms, a halogenated alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 12 carbon atoms or a heteroaryl group having 3 to 12 carbon atoms;

[0032] n1 is the number of R1, n1 is selected from 0, 1, 2, 3 or 4, and when n1 is greater than 1, any two R1 are the same or different;

[0033] n2 is the number of R2, n2 is selected from 0, 1, 2, 3 or 4, and when n2 is greater than 1, any two R2 are the same or different;

[0034] n3 is the number of R3, n3 is selected from 0, 1, 2, 3 or 4, and when n3 is greater than 1, any two R3 are the same or different;

[0035] n4 is the number of R4, n4 is selected from 0, 1, 2, 3 or 4, and when n4 is greater than 1, any two R4 are the same or different;

[0036] Ar1 and Ar2 are the same or different and each independently selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 20 carbon atoms;

[0037] L, L1 and L2 are the same or different and each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms;

[0038] The substituents in Ar1, Ar2, L, L1 and L2 are the same or different and each independently selected from deuterium, a halogen group, a cyano group, a trialkylsilyl group having 3 to 12 carbon atoms, a halogenated alkyl group having 1 to 10 carbon atoms, an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 12 carbon atoms or a heteroaryl group having 3 to 12 carbon atoms.

[0039] In this application, the description methods "each... independently is", "... are respectively independently" 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 expressed between the same symbols do not affect each other, or it can also mean that within the same group, the specific options expressed between the same symbols do not affect each other. For example, " Wherein, each q is independently 0, 1, 2 or 3, and each R” is independently selected from hydrogen, deuterium, fluorine, chlorine, which means that: in formula Q-1, 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; in formula Q-2, there are q substituents R” on each benzene ring of the biphenyl, and the number q of the R” substituents on the two benzene rings can be the same or different, and each R” can be the same or different, and the options of each R” do not affect each other.

[0040] In the present application, the term “substituted or unsubstituted” means that the functional group described after this term may or may not have a substituent (hereinafter, for the 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 unsubstituted aryl. Among them, the above-mentioned substituent, i.e., Rc, can be, for example, deuterium, a halogen group, a cyano group, an alkyl group, a trialkylsilyl group, a haloalkyl group, a cycloalkyl group, an aryl group, a heteroaryl group, etc.

[0041] In the present application, the number of carbon atoms of a substituted or unsubstituted functional group refers to all the carbon atoms. For example, if L1 is a substituted arylene having 12 carbon atoms, then all the carbon atoms of the arylene and its substituents are 12.

[0042] In the present application, an aryl group refers to an optional functional group or substituent derived from an aromatic carbocyclic ring. An aryl group can be a monocyclic aryl group (such as a phenyl group) or a polycyclic aryl group. In other words, an aryl group can be a monocyclic aryl group, a fused polycyclic aryl group, two or more monocyclic aryl groups connected by carbon-carbon bonds, a monocyclic aryl group and a fused polycyclic aryl group connected by carbon-carbon bonds, or two or more fused polycyclic aryl groups connected by carbon-carbon bonds. That is, unless otherwise specified, two or more aromatic groups connected by carbon-carbon bonds can also be regarded as the aryl groups in the present application. Among them, the fused polycyclic aryl group can include, for example, a bicyclic fused aryl group (such as a naphthyl group), a tricyclic fused aryl group (such as a phenanthryl group, a fluorenyl group, an anthryl group), etc. The aryl group does not contain heteroatoms such as B, N, O, S, P, Se, and Si. For example, in the present application, a biphenyl group, a terphenyl group, etc. are aryl groups. Examples of aryl groups can include, but are not limited to, a phenyl group, a naphthyl group, a fluorenyl group, an anthryl group, a phenanthryl group, a biphenyl group, a terphenyl group, a benzo[9,10]phenanthryl group, a pyrenyl group, a benzofluoranthenyl group, a spirobifluorenyl group, etc. In the present application, the arylene group involved refers to a divalent group formed by further removing one hydrogen atom from the aryl group.

[0043] In the present application, the terphenyl group includes

[0044] In the present application, the fluorenyl group can be substituted by one or more substituents. In the case where the above-mentioned fluorenyl group is substituted, the substituted fluorenyl group can be: etc., but is not limited thereto.

[0045] In the present application, the substituted aryl may be one or more than two hydrogen atoms in the aryl being substituted by groups such as deuterium atoms, halogen groups, cyano groups, aryl groups, heteroaryl groups, trialkylsilyl groups, alkyl groups, cycloalkyl groups, haloalkyl groups, deuterated alkyl groups, etc. Specific examples of the heteroaryl-substituted aryl include, but are not limited to, diphenylfuran-substituted phenyl, dibenzothiophene-substituted phenyl, pyridine-substituted phenyl, etc. It should be understood that the number of carbon atoms of the substituted aryl refers to the total number of carbon atoms of the aryl and the substituents on the aryl. For example, a substituted aryl with 18 carbon atoms refers to the total number of carbon atoms of the aryl and the substituents being 18.

[0046] In the present application, the heteroaryl refers to a monovalent aromatic ring or its derivative containing at least one heteroatom in the ring, and the heteroatom may be one or more of B, O, N, P, Si, Se, and S. The heteroaryl may be a monocyclic heteroaryl or a polycyclic heteroaryl. In other words, the heteroaryl may be a single aromatic ring system or a plurality of aromatic ring systems connected by carbon-carbon bonds, and any aromatic ring system is an aromatic monocyclic ring or an aromatic fused ring. Exemplarily, the heteroaryl may include thiophenyl, furyl, pyrrolyl, imidazolyl, thiazolyl, oxazolyl, oxadiazolyl, triazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, acridinyl, pyridazinyl, pyrazinyl, quinolinyl, quinazolinyl, quinoxalinyl, phenoxazinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, isoquinolinyl, indolyl, carbazolyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothiophenyl, dibenzothiophenyl, thienothiophenyl, benzofuryl, phenanthrolinyl, isoxazolyl, thiadiazolyl, phenothiazinyl, silafluorene, dibenzofuryl, and N-phenylcarbazolyl, N-pyridylcarbazolyl, N-methylcarbazolyl, etc., and are not limited thereto. In the present application, the sub-heteroaryl involved refers to a divalent group formed by the heteroaryl further losing one hydrogen atom.

[0047] In the present application, the substituted heteroaryl may be one or more than two hydrogen atoms in the heteroaryl being substituted by groups such as deuterium atoms, halogen groups, cyano groups, aryl groups, heteroaryl groups, trialkylsilyl groups, alkyl groups, cycloalkyl groups, haloalkyl groups, deuterated alkyl groups, etc. Specific examples of the aryl-substituted heteroaryl include, but are not limited to, phenyl-substituted dibenzofuryl, phenyl-substituted dibenzothiophene, phenyl-substituted pyridine, etc. It should be understood that the number of carbon atoms of the substituted heteroaryl refers to the total number of carbon atoms of the heteroaryl and the substituents on the heteroaryl.

[0048] In the present application, the number of carbon atoms of the aryl as a substituent may be 6-12. For example, the number of carbon atoms may be 6, 7, 8, 9, 10, 11, 12. Specific examples of the aryl as a substituent include, but are not limited to, phenyl, biphenyl, naphthyl.

[0049] In the present application, the number of carbon atoms of the heteroaryl group as a substituent can be 3 to 12. For example, the number of carbon atoms can be 3, 4, 5, 6, 7, 8, 9, 10, 11, 12. Specific examples of the heteroaryl group as a substituent include, but are not limited to, pyridyl, pyrimidinyl, carbazolyl, dibenzofuranyl, dibenzothiophenyl, quinolinyl, quinazolinyl, quinoxalinyl, isoquinolinyl.

[0050] In the present application, the alkyl group having 1 to 10 carbon atoms can include a straight-chain alkyl group having 1 to 10 carbon atoms and a branched-chain alkyl group having 3 to 10 carbon atoms. The number of carbon atoms of the alkyl group can be, for example, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10. Specific examples of the alkyl group include, but are not limited to, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl, neopentyl, n-hexyl, n-heptyl, n-octyl, 2-ethylhexyl, nonyl, decyl, 3,7-dimethyloctyl, etc.

[0051] In the present application, the halogen group can be, for example, fluorine, chlorine, bromine, iodine.

[0052] In the present application, specific examples of the trialkylsilyl group include, but are not limited to, trimethylsilyl, triethylsilyl, etc.

[0053] In the present application, specific examples of the haloalkyl group include, but are not limited to, trifluoromethyl.

[0054] In the present application, specific examples of the deuterated alkyl group include, but are not limited to, trideuteriomethyl.

[0055] In the present application, the non-positioning linking bond refers to a single bond extending from the ring system It means that one end of the linking bond can be connected to any position in the ring system penetrated by the bond, and the other end is connected to the rest of the compound molecule. For example, as shown in the following formula (f), the naphthyl group represented by formula (f) is connected 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) to (f-10):

[0056]

[0057] For another example, as shown in the following formula (X'), the dibenzofuranyl group represented by formula (X') is connected to other positions of the molecule through a non-positioning linking bond extending from the middle of one benzene ring on one side, and the meaning it represents includes any possible linking mode shown in formulas (X'-1) to (X'-4):

[0058]

[0059] In some embodiments of the present application, the organic compound of the present application is selected from the structures represented by the following Formula I-1, Formula I-2, Formula I-3, Formula I-4 or Formula I-5:

[0060]

[0061] In some embodiments of the present application, R1, R2, R3 and R4 are the same or different, and each independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trimethylsilyl, trideuteriomethyl, trifluoromethyl, phenyl, naphthyl, biphenyl, dibenzofuranyl, dibenzothiophenyl or carbazolyl.

[0062] In some embodiments of the present application, Ar1 and Ar2 are the same or different, and each independently selected from substituted or unsubstituted aryl groups having 6 to 25 carbon atoms, substituted or unsubstituted heteroaryl groups having 12 to 20 carbon atoms. For example, Ar1 and Ar2 are the same or different, and each independently selected from substituted or unsubstituted aryl groups having 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25 carbon atoms, substituted or unsubstituted heteroaryl groups having 12, 13, 14, 15, 16, 17, 18, 19, 20 carbon atoms.

[0063] Optionally, the substituents in Ar1 and Ar2 are each independently selected from deuterium, fluorine, cyano, trialkylsilyl having 3 to 6 carbon atoms, haloalkyl having 1 to 5 carbon atoms, alkyl having 1 to 5 carbon atoms, aryl having 6 to 12 carbon atoms or heteroaryl having 5 to 12 carbon atoms.

[0064] In some embodiments of the present application, Ar1 and Ar2 are the same or different, and each independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted spirobifluorenyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted carbazolyl.

[0065] Optionally, the substituents in Ar1 and Ar2 are each independently selected from deuterium, fluorine, cyano, trimethylsilyl, trifluoromethyl, methyl, ethyl, isopropyl, tert-butyl or phenyl.

[0066] In some embodiments of the present application, Ar1 and Ar2 are the same or different, and each independently selected from the group consisting of the following groups:

[0067]

[0068] In some embodiments of the present application, Ar1 and Ar2 are the same or different and are each independently selected from the group consisting of the following groups:

[0069]

[0070] In some embodiments of the present application, L, L1, and L2 are each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 18 carbon atoms. For example, L, L1, and L2 are each independently selected from a single bond, a substituted or unsubstituted arylene group having 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, or 18 carbon atoms.

[0071] Optionally, the substituents in L, L1, and L2 are each independently selected from deuterium, fluorine, cyano group, trifluoromethyl group, trimethylsilyl group, an alkyl group having 1 to 5 carbon atoms, or a phenyl group.

[0072] In some embodiments of the present application, L, L1, and L2 are each independently selected from a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, or a substituted or unsubstituted biphenylene group.

[0073] Optionally, the substituents in L, L1, and L2 are each independently selected from deuterium, fluorine, cyano group, trifluoromethyl group, trimethylsilyl group, methyl group, ethyl group, isopropyl group, tert-butyl group, or a phenyl group.

[0074] In some embodiments of the present application, L, L1, and L2 are the same or different and are each independently selected from a single bond or the group consisting of the following groups:

[0075]

[0076] In some embodiments of the present application, L, L1, and L2 are the same or different and are each independently selected from a single bond or the group consisting of the following groups:

[0077]

[0078] In some embodiments of the present application, are the same or different and are each independently selected from the group consisting of the following groups:

[0079]

[0080] In some embodiments of the present application, are the same or different and are each independently selected from the group consisting of the following groups:

[0081]

[0082] Specifically, the organic compound is selected from the group consisting of the following compounds:

[0083]

[0084]

[0085]

[0086]

[0087]

[0088]

[0089]

[0090]

[0091]

[0092] In a second aspect, the present application provides an electronic component, comprising an anode and a cathode disposed opposite to each other, and a functional layer disposed between the anode and the cathode; the functional layer contains the organic compound of the present application.

[0093] Optionally, the functional layer includes a hole transport layer, and the hole transport layer contains the organic compound.

[0094] Optionally, the electronic component is an organic electroluminescent device or a photoelectric conversion device.

[0095] Optionally, the organic electroluminescent device is a red organic electroluminescent device.

[0096] Further optionally, the hole transport layer includes a first hole transport layer and a second hole transport layer. Relative to the second hole transport layer, the first hole transport layer is closer to the anode, and wherein, the second hole transport layer contains the organic compound of the present application.

[0097] In one embodiment, the electronic component is an organic electroluminescent device. As Figure 1 shown, the organic electroluminescent device may include an anode 100, a first hole transport layer 321, a second hole transport layer 322, an organic light emitting layer 330, an electron transport layer 350, and a cathode 200 which are stacked. Among them, the first hole transport layer 321 and the second hole transport layer 322 constitute the hole transport layer 320.

[0098] Optionally, the anode 100 includes the following anode materials, which are preferably materials with a large work function (work function) that contribute to 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. Preferably, a transparent electrode including indium tin oxide (ITO) is included as the anode.

[0099] Optionally, the hole transport layer includes one or more hole transport materials, which can be selected from carbazole polymers, carbazole-linked triarylamine compounds, or other types of compounds, and this application does not make special regulations thereon. For example, the material of the first hole transport layer is selected from the group consisting of the following compounds:

[0100]

[0101] In a specific embodiment, the first hole transport layer 321 is HT-5.

[0102] In another specific embodiment, the second hole transport layer 322 is a compound of this application.

[0103] Optionally, the organic light-emitting layer 330 can be composed of a single light-emitting layer 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, and the excitons transfer energy to the host material, and the host material transfers energy to the guest material, thereby enabling the guest material to emit light.

[0104] The host material of the organic light-emitting layer 330 can be a metal chelate compound, a bisstyryl derivative, an aromatic amine derivative, a dibenzofuran derivative, or other types of materials, and this application does not make special restrictions thereon. The host material can be a single host material or a mixed host material. In an embodiment of this application, the host material of the organic light-emitting layer 330 is RH-1

[0105] The guest material of the organic light-emitting layer 330 can be selected with reference to the prior art. For example, it can be selected from iridium(III) organometallic complexes, platinum(II) organometallic complexes, ruthenium(II) complexes, etc. Specific examples of the guest material include, but are not limited to,

[0106]

[0107] In one embodiment of the present application, the guest material of the organic light-emitting layer 330 is RD-1

[0108] In the present application, the hole blocking layer 340 can be a single-layer structure or a multi-layer structure, and it can include one or more hole blocking materials. In a more specific embodiment, the material of the hole blocking layer 340 is HB-1

[0109] Optionally, the electron transport layer 350 can be a single-layer structure or a multi-layer structure, and it can include one or more electron transport materials. The electron transport materials usually can contain metal complexes or / and nitrogen-containing heterocyclic derivatives. Among them, the metal complex materials can be selected from, for example, LiQ, Alq3, etc.; the nitrogen-containing heterocyclic derivatives can be aromatic rings with a nitrogen-containing six-membered ring or five-membered ring skeleton, fused aromatic ring compounds with a nitrogen-containing six-membered ring or five-membered ring skeleton, etc. Specific examples include, but are not limited to, 1,10-phenanthroline compounds such as Bphen, NBphen, ET-20, BimiBphen, or anthracene compounds, triazine compounds or pyrimidine compounds containing heteroaryl groups as shown in the following structure. In one embodiment of the present application, the electron transport layer 350 is composed of ET-20 and LiQ

[0110]

[0111] In the present application, the cathode 200 can include a cathode material, which is a material with a small work function that helps the electron injection material 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 their alloys; or multi-layer materials such as LiF / Al, Liq / Al, LiO2 / Al, LiF / Ca, LiF / Al, and BaF2 / Ca. Preferably, a metal electrode containing magnesium and silver is included as the cathode

[0112] Optionally, as Figure 1 shown, a hole injection layer 310 is further provided between the anode 100 and the first hole transport layer 321 to enhance the ability to inject holes into the first hole transport layer 321. The hole injection layer 310 can be selected from benzidine derivatives, starburst arylamine compounds, phthalocyanine derivatives, or other materials, and the present application does not make special restrictions on this. For example, the compound contained in the hole injection layer 310 is selected from the group consisting of the following compounds

[0113]

[0114]

[0115] In a specific embodiment of the present application, the hole injection layer 310 is HT-5 and NDP.

[0116] Optionally, as Figure 1 shown, an electron injection layer 360 is further provided between the cathode 200 and the electron transport layer 350 to enhance the ability to inject electrons into the electron transport layer 350. The electron injection layer 360 may include inorganic materials such as alkali metal sulfides and alkali metal halides, or may include complexes of alkali metals and organic compounds. For example, the electron injection layer 360 includes Yb.

[0117] According to another embodiment, the electronic component is a photoelectric conversion device. As Figure 3 shown, the photoelectric conversion device may include 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 contains the organic compound provided by the present application.

[0118] According to a specific embodiment, as Figure 3 shown, the photoelectric conversion device includes an anode 100, a hole transport layer 320, a photoelectric conversion layer 370, an electron transport layer 350, and a cathode 200 stacked in sequence. Optionally, the hole transport layer 320 contains the organic compound of the present application.

[0119] Optionally, the photoelectric conversion device may be a solar cell, especially an organic thin film solar cell. For example, in an embodiment of the present application, the solar cell includes an anode, a hole transport layer, a photoelectric conversion layer, an electron transport layer, and a cathode stacked in sequence, wherein the hole transport layer contains the organic compound of the present application.

[0120] In a third aspect, the present application provides an electronic device including the electronic component provided in the second aspect of the present application.

[0121] According to an embodiment, as Figure 2 shown, the electronic device is a first electronic device 400, and the first electronic device 400 includes the above-mentioned organic electroluminescent device. The first electronic device 400 may be, for example, a display device, a lighting device, an optical communication device, or other types of electronic devices, and may 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.

[0122] According to another embodiment, as Figure 4As shown, the electronic device is a second electronic device 500, and the second electronic device 500 includes the above-mentioned photoelectric conversion device. The second electronic device 500 can be, for example, a solar power generation device, a light detector, a fingerprint recognition device, an optical module, a CCD camera or other types of electronic devices.

[0123] The synthesis method of the organic compound of the present application is specifically described below in conjunction with synthesis examples, but the present application is not limited thereto.

[0124] The compounds whose synthesis methods are not mentioned in this application are raw materials obtained from commercial channels.

[0125] Synthesis example

[0126] Intermediate synthesis

[0127] 1. Synthesis of intermediate IM1

[0128]

[0129] Under the protection of nitrogen, 2-bromo-4-chlorobiphenyl (100 g, 374 mmol) and tetrahydrofuran (800 mL) were added to a 2L three-necked round-bottom flask, dissolved at -80°C to -90°C until clear, n-BuLi (148 mL) was slowly added dropwise to the reaction system, and reacted at -80°C to -90°C for 50 min. Then, 5-phenylindeno[1,2-b]indol-10(5h)-one (132.5 g, 449 mmol) was added, 5-phenylindeno[1,2-b]indol-10(5h)-one was dissolved in tetrahydrofuran (260 mL), and then slowly added dropwise to the reaction system, and reacted at -80°C to -90°C for 1 h. After the reaction is completed, the temperature is naturally raised to room temperature, 5% dilute hydrochloric acid is poured into the reaction solution to adjust the pH to <7, and after sufficient stirring, dichloromethane is added for extraction. The organic phases are combined, washed with water until neutral, and dried with anhydrous magnesium sulfate. After filtering, the solvent is removed under reduced pressure, and the obtained oil is added to a flask with n-heptane, heated to reflux until the solution is clarified, and placed at -20°C for recrystallization to obtain the intermediate IM1-1 (123 g, yield 68%) as a white solid.

[0130] The intermediate X-1 shown in Table 1 was prepared by referring to the synthesis method of intermediate IM1-1, except that raw material 1 was used instead of 2-bromo-4-chlorobiphenyl, wherein the main raw materials used, the synthesized intermediates and their yields are shown in Table 1.

[0131] Table 1

[0132]

[0133] 2. Synthesis of intermediate IM1

[0134]

[0135] Under the protection of nitrogen, add intermediate IM1-1 (123 g, 254 mmol) and glacial acetic acid (1.5 L) to a 2 L three-necked round-bottom flask, stir at 50 °C to 60 °C. After the reaction solution becomes completely clear, drop in concentrated sulfuric acid (3.08 mL), continue to heat up to 70 °C - 80 °C, stir for 30 min, then let the reaction solution cool down to room temperature naturally, pour it into deionized water (2 L), stir well and filter. Wash the filter cake with deionized water until neutral, put it into a vacuum drying oven to dry the material for 1 h, dissolve it with dichloromethane, add anhydrous sodium sulfate to dry for 30 min, filter and then remove the solvent under reduced pressure. Add n-heptane and dichloromethane, recrystallize the crude product at -20 °C, filter and dry the material in a vacuum drying oven to obtain intermediate IM1 (108 g, yield 91%) as a white solid.

[0136] Refer to the synthesis method of intermediate IM1 to prepare intermediate X shown in Table 2. The difference is that intermediate IMX-1 is used instead of intermediate IM1-1. Among them, the main raw materials used, the synthesized intermediates and their yields are shown in Table 2.

[0137] Table 2

[0138]

[0139]

[0140] 3. Synthesis of intermediate IM4-1

[0141]

[0142] Under the protection of nitrogen, add indeno[1,2-b]indol-10(5H)-one (100 g, 456 mmol), p-chloroiodobenzene (194 g, 684 mmol), copper(I) iodide (8.5 g, 45.6 mmol), potassium carbonate (157.3 g, 1140 mmol), 1,10-phenanthroline (4.1 g, 22.8 mmol), 18-crown-6 (12 g, 45.6 mmol) and dimethylformamide (1000 mL) to a 2 L three-necked round-bottom flask. Heat up to 150 °C under stirring and keep for 16 h; then cool the reaction mixture to room temperature, add ethyl acetate (200 mL) and deionized water (200 mL), stir for 15 min, separate the organic phase, add anhydrous magnesium sulfate to dry and then remove the solvent under reduced pressure; use dichloromethane / n-heptane as the mobile phase to purify the obtained crude product by silica gel column chromatography to obtain intermediate IM4-1 (97.7 g, yield 65%).

[0143] The intermediate IMX-1 shown in Table 3 was prepared by referring to the synthesis method of the intermediate IM4-1, except that the raw material 2 was used instead of p-chloroiodobenzene, wherein the main raw materials used, the synthesized intermediates and their yields are shown in Table 3.

[0144] Table 3

[0145]

[0146] 4. Intermediate IM4-2

[0147]

[0148] Under the protection of nitrogen, 2-bromobiphenyl (46 g, 197 mmol) and tetrahydrofuran (400 mL) were added to a 2L three-necked round-bottom flask, dissolved at -80°C to -90°C until clear, and n-BuLi (74 mL) was slowly added dropwise. After the reaction was carried out at a constant temperature of -80°C to -90°C for 50 min, the intermediate IM4-1 (97.7 g, 296 mmol) was weighed, dissolved in tetrahydrofuran (130 mL), and then slowly added dropwise to the reaction system, and the reaction was carried out at a constant temperature of -80°C to -90°C for 1 h. After the reaction is completed, the temperature is naturally raised to room temperature, 5% dilute hydrochloric acid is poured into the reaction solution to adjust the pH to <7, and after sufficient stirring, dichloromethane is added for extraction. The organic phases are combined, washed with water until neutral, and dried with anhydrous magnesium sulfate. After filtering, the solvent is removed under reduced pressure, and the obtained oil is added to a flask with n-heptane, heated to reflux until the solution is clear, and placed at -20°C for recrystallization to obtain the intermediate IM4-2 (93 g, yield 65%) as a white solid.

[0149] The intermediate IMX-2 shown in Table 4 was prepared by referring to the synthesis method of the intermediate IM4-2, except that the intermediate IMX-1 was used instead of IM4-1, wherein the main raw materials used, the synthesized intermediates and their yields are shown in Table 4.

[0150] Table 4

[0151]

[0152] 5. Synthesis of intermediate IM4

[0153]

[0154] Under the protection of nitrogen, add intermediate IM4-2 (93 g, 192 mmol) and glacial acetic acid (0.8 L) to a 2 L three-necked round-bottom flask, stir at 50 °C to 60 °C. After the reaction solution becomes completely clear, drop in concentrated sulfuric acid (2.02 mL), continue to heat up to 70 °C to 80 °C, stir for 30 min, then let the reaction solution cool naturally to room temperature, pour it into deionized water (1.5 L), stir well and filter. Wash the filter cake with deionized water until neutral, put it into a vacuum drying oven to dry the material for 1 h, dissolve it with dichloromethane, add anhydrous sodium sulfate to dry for 30 min, filter and then remove the solvent under reduced pressure. Add n-heptane, distill off dichloromethane, recrystallize the crude product at -20 °C, filter and dry the material in a vacuum drying oven to obtain intermediate IM4 as a white solid (78.7 g, yield 88%).

[0155] Prepare intermediate IMX shown in Table 5 according to the synthesis method of intermediate IM4, except that intermediate IMX-2 is used instead of IM4-2. The main raw materials used, the synthesized intermediates and their yields are shown in Table 5.

[0156] Table 5

[0157]

[0158]

[0159] Synthesis Example 1: Synthesis of Compound 4

[0160]

[0161] Under the protection of nitrogen, add intermediate IM1 (10 g, 21 mmol), aniline (2 g, 21 mmol) and toluene (100 mL) to a 250 mL three-necked round-bottom flask. After dissolving and clarifying, reflux and stir for 30 min, then lower the temperature to 70 °C to 80 °C, add sodium tert-butoxide (3 g, 31 mmol), 2-dicyclohexylphosphino-2,4,6-triisopropylbiphenyl (0.2 g, 0.42 mmol) and tris(dibenzylideneacetone)dipalladium (0.21 g, 0.21 mmol), reflux and react for 5 h, then stop the reaction. After the reaction temperature drops to room temperature, extract with toluene and water, wash the organic phase with water until neutral, add anhydrous sodium sulfate to remove water for 30 min, filter and use toluene as the eluent, pass through a sand core silica gel funnel, concentrate the column liquid, and recrystallize with dichloromethane∶n-heptane (v / v = 1∶2) to obtain intermediate IM1-a as a white solid (8.2 g, yield 74.6%).

[0162]

[0163] Under nitrogen protection, intermediate IM1-a (8.2 g, 15.7 mmol), 4-bromobiphenyl (3.4 g, 15.7 mmol) and toluene (80 mL) were added to a 250 mL three-necked round-bottom flask. After dissolution and clarification, and reflux stirring for 30 min, the temperature was lowered to 70 °C to 80 °C, and sodium tert-butoxide (2.5 g, 26 mmol), 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl (0.14 g, 0.35 mmol) and tris(dibenzylideneacetone)dipalladium (0.16 g, 0.17 mmol) were added. After reflux reaction for 5 h, the reaction was stopped. After the reaction temperature dropped to room temperature, extraction was carried out with toluene and water. The organic phase was washed with water until neutral, anhydrous sodium sulfate was added to remove water for 30 min, and after filtration, toluene was used as the eluent, and it was passed through a sand core silica gel funnel. The column eluate was concentrated, and recrystallization was carried out with ethyl acetate∶petroleum ether (v / v = 1∶10) to obtain compound 4 as a white solid (7.1 g, yield 67%), and the mass spectrum (m / z) = 675.27 [M+H] + 。

[0164] The compounds shown in Table 6 were prepared by referring to the synthesis method of compound 4, except that IMX was used instead of IM1, raw material 3 was used instead of aniline, and raw material 4 was used instead of 4-bromobiphenyl. Among them, the main raw materials used, the synthesized compounds, and their final step yields and mass spectra are shown in Table 6.

[0165] Table 6

[0166]

[0167]

[0168]

[0169]

[0170]

[0171] 1H-NMR data of compound 21:

[0172] 1 H-NMR (400 MHz, CD2Cl2) δ ppm 8.26 (d, 1H), 8.12 - 8.04 (m, 2H), 7.95 - 7.56 (m, 24H), 7.49 - 7.42 (m, 2H), 7.20 - 7.15 (m, 2H), 6.90 (d, 1H), 6.85 - 6.78 (m, 3H), 6.71 (s, 1H), 1.61 (s, 6H).

[0173] 1H-NMR data of compound 136:

[0174] 11H-NMR (400 MHz, CD2Cl2) δ ppm 8.38 - 8.27 (m, 4H), 8.04 (d, 1H), 7.95 - 7.56 (m, 24H), 7.56 - 7.51 (m, 4H), 7.46 (d, 2H), 7.37 (d, 1H).

[0175] Example 1: Red Organic Light-Emitting Device

[0176] First, the anode pretreatment is carried out through the following process: The ITO / Ag / ITO substrate with the following thicknesses is cut into a size of 40 mm (length) × 40 mm (width) × 0.7 mm (height). The substrate is cleaned with organic solvents and ultrapure water to remove impurities and organic pollutants on the substrate surface, and surface treatment is carried out using ultraviolet ozone and O2:N2 plasma to increase the work function of the anode.

[0177] On the above substrate, compound HT-5 and NDP are co-evaporated at an evaporation rate ratio of 97%:3% to form a hole injection layer with a thickness of ...

[0178] Compound HT-5 is vacuum-evaporated on the hole injection layer to form a first hole transport layer with a thickness of ...

[0179] Compound 21 is vacuum-evaporated on the first hole transport layer to form a second hole transport layer with a thickness of ...

[0180] On the second hole transport layer, compound RH-1 and compound RD-1 are co-evaporated at an evaporation rate ratio of 98.5%:1.5% to form an organic light-emitting layer with a thickness of ...

[0181] Compound HB-1 is vacuum-evaporated on the organic light-emitting layer to form a hole blocking layer with a thickness of ...

[0182] On the hole blocking layer, compound ET-20 and LiQ are co-evaporated at an evaporation rate ratio of 1:1 to form an electron transport layer with a thickness of ...

[0183] Ytterbium (Yb) is evaporated on the electron transport layer to form an electron injection layer with a thickness of Then, magnesium (Mg) and silver (Ag) are co-evaporated at an evaporation rate ratio of 1:10 to form a cathode with a thickness of ...

[0184] Finally, compound CP-1 is evaporated on the cathode to form a layer with a thickness of of the organic covering layer, thus completing the manufacture of the red organic light-emitting device.

[0185] Examples 2 - 27:

[0186] An organic light-emitting device was prepared by the same method as in Example 1, except that the compound in Table 5 was used to replace Compound 21 in Example 1 when preparing the second hole transport layer.

[0187] Comparative Examples 1 - 4

[0188] An organic light-emitting device was prepared by the same method as in Example 1, except that the comparative compounds A, B, C, and D in Table 4 were used to replace Compound 21 in Example 1 when preparing the second hole transport layer.

[0189] Among them, when preparing the organic light-emitting device, the structures of the respective materials in the comparative examples and examples are as follows:

[0190]

[0191]

[0192] The red organic light-emitting devices prepared in Examples 1 - 27 and Comparative Examples 1 - 4 were subjected to performance tests. The IVL test conditions for the devices were 10 mA / cm 2 , and the device T 95 The lifetime test conditions were 30 mA / cm 2 , and the test results are shown in Table 7 below.

[0193] Table 7

[0194]

[0195]

[0196] Referring to Table 7 above, it can be seen that in Examples 1 - 27, when the compound of the present application was used as the second hole transport layer, compared with Comparative Examples 1 - 4, the current efficiency was increased by at least 10.53%, and the device lifetime was increased by at least 12.22%.

[0197] Compared with Compound A, the compound of the example of the present application had the current efficiency increased by at least 14.93% and the lifetime increased by at least 18.82%. The reason is that the indole of Compound A is fused with diphenylfluorene, and the structure is prone to torsion, while the indole of the compound of the present application is fused with spirofluorene, and the whole molecule is close to a three-dimensional spherical structure, having a large spatial volume, good film-forming property and thermal stability, and high hole mobility. When it is used as the hole transport layer material of the organic light-emitting device, the efficiency and lifetime of the organic light-emitting device can be improved.

[0198] Compared with compound B, the compound of the embodiment of the present application has a narrower band gap and is more conducive to hole transport. Therefore, the current efficiency is increased by at least 13.64%, and the lifetime is increased by at least 16.09%.

[0199] Compared with compound C, the substituents on the core structure of the compound of the embodiment of the present application are all electron-donating groups, and the LUMO is shallower, which can block electron diffusion. The current efficiency is increased by at least 10.53%, and the lifetime is increased by at least 12.22%.

[0200] Compared with compound D, the compound of the embodiment of the present application has better film-forming properties, avoids material crystallization, and also has better thermal stability. The current efficiency is increased by at least 11.06%, and the lifetime is increased by at least 13.91%.

Claims

1. An organic compound, characterized in that, The organic compound has the structure shown in Formula 1: Wherein, Ar is selected from phenyl, naphthyl or biphenyl; R1, R2, R3 and R4 are the same or different, and 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 alkyl group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 12 carbon atoms or a heteroaryl group having 3 to 12 carbon atoms; n1 is the number of R1, n1 is selected from 0, 1, 2, 3 or 4, and when n1 is greater than 1, any two R1 are the same or different; n2 is the number of R2, n2 is selected from 0, 1, 2, 3 or 4, and when n2 is greater than 1, any two R2 are the same or different; n3 is the number of R3, n3 is selected from 0, 1, 2, 3 or 4, and when n3 is greater than 1, any two R3 are the same or different; n4 is the number of R4, n4 is selected from 0, 1, 2, 3 or 4, and when n4 is greater than 1, any two R4 are the same or different; Ar1 and Ar2 are the same or different, and each independently selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 20 carbon atoms; L, L1 and L2 are the same or different, and each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms; The substituents in Ar1, Ar2, L, L1 and L2 are the same or different, and each independently selected from deuterium, a halogen group, a cyano group, a trialkylsilyl group having 3 to 12 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 12 carbon atoms or a heteroaryl group having 3 to 12 carbon atoms.

2. The organic compound according to claim 1, wherein, R1, R2, R3 and R4 are the same or different, and each independently selected from deuterium, fluorine, a cyano group, methyl, ethyl, isopropyl, tert-butyl, trimethylsilyl, trideuteromethyl, trifluoromethyl, phenyl, naphthyl, biphenyl, dibenzofuranyl, dibenzothiophenyl or carbazolyl.

3. The organic compound according to claim 1, wherein, Ar1 and Ar2 are the same or different, and each independently selected from a substituted or unsubstituted aryl group having 6 to 25 carbon atoms, a substituted or unsubstituted heteroaryl group having 12 to 20 carbon atoms; Optionally, the substituents in Ar1 and Ar2 are each independently selected from deuterium, fluorine, a cyano group, a trialkylsilyl group having 3 to 6 carbon atoms, a haloalkyl group having 1 to 5 carbon atoms, an alkyl group having 1 to 5 carbon atoms, an aryl group having 6 to 12 carbon atoms or a heteroaryl group having 5 to 12 carbon atoms.

4. The organic compound according to claim 1, wherein, Ar1 and Ar2 are the same or different, and each independently selected from a substituted or unsubstituted phenyl, a substituted or unsubstituted naphthyl, a substituted or unsubstituted biphenyl, a substituted or unsubstituted terphenyl, a substituted or unsubstituted fluorene, a substituted or unsubstituted spirobifluorene, a substituted or unsubstituted phenanthrene, a substituted or unsubstituted dibenzofuran, a substituted or unsubstituted dibenzothiophene, a substituted or unsubstituted carbazole; Optionally, the substituents in Ar1 and Ar2 are each independently selected from the group consisting of deuterium, fluorine, cyano, trimethylsilyl, trifluoromethyl, methyl, ethyl, isopropyl, tert-butyl, or phenyl.

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

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

7. The organic compound according to claim 1, wherein, L, L1, and L2 are each independently selected from a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, or a substituted or unsubstituted biphenylene group; Optionally, the substituents in L, L1, and L2 are each independently selected from the group consisting of deuterium, fluorine, cyano, trifluoromethyl, trimethylsilyl, methyl, ethyl, isopropyl, tert-butyl, or phenyl.

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

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

10. 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 contains the organic compound according to any one of claims 1 to 9.

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

12. Electronic device, characterized in that, The electronic device includes the electronic component according to claim 10 or 11.

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