WO2022105313A1 - 有机化合物以及使用其的有机电致发光器件和电子装置 - Google Patents

有机化合物以及使用其的有机电致发光器件和电子装置 Download PDF

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WO2022105313A1
WO2022105313A1 PCT/CN2021/111341 CN2021111341W WO2022105313A1 WO 2022105313 A1 WO2022105313 A1 WO 2022105313A1 CN 2021111341 W CN2021111341 W CN 2021111341W WO 2022105313 A1 WO2022105313 A1 WO 2022105313A1
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carbon atoms
substituted
unsubstituted
independently selected
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马天天
杨雷
张孔燕
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陕西莱特光电材料股份有限公司
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Definitions

  • the present application belongs to the technical field of organic materials, and specifically provides an organic compound and an organic electroluminescence device and electronic device using the same.
  • Such electronic components usually include oppositely disposed cathodes and anodes, and functional layers disposed between the cathodes and the anodes.
  • the functional layer is composed of multiple organic or inorganic film layers, and generally includes an energy conversion layer, a hole transport layer between the energy conversion layer and the anode, and an electron transport layer between the energy conversion layer and the cathode.
  • an organic electroluminescence device as an example, it generally includes an anode, a hole transport layer, an electroluminescence layer as an energy conversion layer, an electron transport layer and a cathode which are stacked in sequence.
  • an electric field is generated between the two electrodes.
  • the electrons on the cathode side move to the electroluminescent layer, and the holes on the anode side also move to the light-emitting layer, and the electrons and holes combine in the electroluminescent layer.
  • Excitons are formed, and the excitons are in an excited state to release energy to the outside, thereby causing the electroluminescent layer to emit light to the outside.
  • the purpose of the present application is to provide an organic compound to further improve the performance of organic electroluminescent devices.
  • ring A is selected from the group shown in formula A:
  • R 6 , R 7 , R 8 and R 9 are each independently selected from hydrogen, deuterium, a substituted or unsubstituted aryl group with 6-30 carbon atoms, a substituted or unsubstituted hetero group with 6-30 carbon atoms Aryl;
  • R 6 , R 7 , R 8 and R 9 are connected to each other to form an aromatic ring with 6-14 carbon atoms;
  • Ar 1 and Ar 2 are each independently selected from an unsubstituted arylene group having 6-20 carbon atoms and an unsubstituted heteroarylene group having 3-20 carbon atoms;
  • R 1 and R 2 are the same or different, and are each independently selected from hydrogen, deuterium, halogen group, cyano group, alkyl group having 1-30 carbon atoms, cycloalkyl group having 3-30 carbon atoms, carbon An alkoxy group with 1-30 atoms, a trialkylsilyl group with 3-12 carbon atoms, a triarylsilyl group with 18-24 carbon atoms, or the structure shown in formula B;
  • L 1 and L 2 are the same or different, and are independently selected from a single bond, a substituted or unsubstituted arylene group with 6-30 carbon atoms, and a substituted or unsubstituted heteroarylene group with 3-30 carbon atoms Aryl;
  • Ar is selected from substituted or unsubstituted aryl groups with 6-30 carbon atoms, and substituted or unsubstituted heteroaryl groups with 3-30 carbon atoms;
  • R 3 , R 4 and R 5 are the same or different, and are each independently selected from deuterium, halogen group, cyano group, alkyl group having 1-10 carbon atoms, aryl group having 6-20 carbon atoms, carbon Heteroaryl with 3-20 atoms;
  • n 3 represents the number of R 3
  • n 4 represents the number of R 4
  • n 5 represents the number of R 5 ;
  • n 3 is selected from: 0, 1, 2, 3 or 4;
  • n 4 is selected from: 0, 1 or 2;
  • n 5 is selected from: 0, 1, 2, 3 or 4;
  • R 6 , R 7 , R 8 , R 9 , L 1 , L 2 and Ar are each independently selected from deuterium, halogen group, cyano group, heteroaryl group having 3-20 carbon atoms, any Aryl having 6-20 carbon atoms, optionally substituted by 0, 1, 2, 3, 4 or 5 substituents independently selected from deuterium, fluorine, cyano, methyl, tert-butyl Trialkylsilyl with 3-12 atoms, triarylsilyl with 18-24 carbon atoms, alkyl group with 1-10 carbon atoms, halogenated alkyl group with 1-10 carbon atoms, carbon atom Cycloalkyl with 3-10 carbon atoms, heterocycloalkyl with 2-10 carbon atoms.
  • a second aspect of the present application provides an organic electroluminescence device, the electronic component includes an anode and a cathode disposed oppositely, and a functional layer disposed between the anode and the cathode; the functional layer comprises the The organic compound described in the first aspect of the application;
  • the functional layer includes an organic light-emitting layer, and the organic light-emitting layer includes the organic compound;
  • the organic light-emitting layer contains a host material, and the host material contains the organic compound.
  • a third aspect of the present application provides an electronic device including the organic electroluminescent device described in the second aspect of the present application.
  • the compound of the present application has the following characteristics:
  • the compound of the present application uses indolo[2,3-a]carbazole as the core group, and three aromatic ring systems are connected together at its N and N' positions to form a macrocyclic structure; in this structure, indole
  • the [2,3-a]carbazole group has a high first triplet energy level and excellent energy transport properties.
  • the macrocyclic structure formed by three aromatic ring systems interconnected by single bonds has both a twisted structure and high rigidity.
  • the high carrier mobility characteristics, good exciton energy transfer characteristics, and good film-forming properties of materials resulting from reduced intermolecular stacking; and through different arylene or heteroarylene groups and the The adjustment of the types of substituents can easily adjust the energy levels and physical properties of the molecules.
  • the second connecting group (the ring A group not directly connected to indolo[2,3-a]carbazole) is an ortho-connected arylene group, so that the maximum To a certain extent, the deformation of the single bond between the linking groups and the tension of the macrocycle are reduced, so that the compound of the present application has higher thermodynamic and chemical stability.
  • the compound of the present application is used in the organic light-emitting layer of an organic electroluminescent device, the light-emitting efficiency and lifetime of the device can be effectively improved on the premise of maintaining a lower driving voltage.
  • FIG. 1 is a schematic structural diagram of an organic electroluminescent device according to an embodiment of the present application.
  • FIG. 2 is a schematic structural diagram of an electronic device according to an embodiment of the present application.
  • a first aspect of the present application provides an organic compound, the structure of which is shown in formula I:
  • ring A is selected from the group shown in formula A:
  • R 6 , R 7 , R 8 and R 9 are each independently selected from hydrogen, deuterium, a substituted or unsubstituted aryl group with 6-30 carbon atoms, a substituted or unsubstituted hetero group with 6-30 carbon atoms Aryl;
  • R 6 , R 7 , R 8 and R 9 are connected to each other to form an aromatic ring with 6-14 carbon atoms;
  • Ar 1 and Ar 2 are each independently selected from an unsubstituted arylene group having 6-20 carbon atoms and an unsubstituted heteroarylene group having 3-20 carbon atoms;
  • R 1 and R 2 are the same or different, and are each independently selected from hydrogen, deuterium, halogen group, cyano group, alkyl group having 1-30 carbon atoms, cycloalkyl group having 3-30 carbon atoms, carbon An alkoxy group with 1-30 atoms, a trialkylsilyl group with 3-12 carbon atoms, a triarylsilyl group with 18-24 carbon atoms, or the structure shown in formula B;
  • L 1 and L 2 are the same or different, and are independently selected from a single bond, a substituted or unsubstituted arylene group with 6-30 carbon atoms, and a substituted or unsubstituted heteroarylene group with 3-30 carbon atoms base;
  • Ar is selected from substituted or unsubstituted aryl groups with 6-30 carbon atoms, and substituted or unsubstituted heteroaryl groups with 3-30 carbon atoms;
  • R 3 , R 4 and R 5 are the same or different, and are each independently selected from deuterium, halogen group, cyano group, alkyl group having 1-10 carbon atoms, aryl group having 6-20 carbon atoms, carbon Heteroaryl with 3-20 atoms;
  • n 3 represents the number of R 3
  • n 4 represents the number of R 4
  • n 5 represents the number of R 5 ;
  • n 3 is selected from: 0, 1, 2, 3 or 4;
  • n 4 is selected from: 0, 1 or 2;
  • n 5 is selected from: 0, 1, 2, 3 or 4;
  • R 6 , R 7 , R 8 , R 9 , L 1 , L 2 and Ar are each independently selected from deuterium, halogen group, cyano group, heteroaryl group having 3-20 carbon atoms, any Aryl having 6-20 carbon atoms, optionally substituted by 0, 1, 2, 3, 4 or 5 substituents independently selected from deuterium, fluorine, cyano, methyl, tert-butyl Trialkylsilyl with 3-12 atoms, triarylsilyl with 18-24 carbon atoms, alkyl group with 1-10 carbon atoms, halogenated alkyl group with 1-10 carbon atoms, carbon atom Cycloalkyl with 3-10 carbon atoms, heterocycloalkyl with 2-10 carbon atoms.
  • the terms “optional” and “optionally” mean that the subsequently described event or circumstance can, but need not, occur, and that the description includes instances where the event or circumstance does or does not occur.
  • “optionally, two adjacent substituents XX form a ring;” means that the two substituents may form a ring but need not form a ring, including: the situation where two adjacent substituents form a ring and two A scenario where adjacent substituents do not form a ring.
  • the number of carbon atoms optionally substituted by 0, 1, 2, 3, 4 or 5 substituents independently selected from deuterium, fluorine, cyano, methyl, tert-butyl is 6- 20
  • Aryl means that the aryl group may be substituted by one or more of deuterium, fluorine, cyano, methyl, and tert-butyl, or not by deuterium, fluorine, cyano, methyl, or tert-butyl. , and when the number of substituents on the aryl group is greater than or equal to 2, the substituents may be the same or different.
  • each independently is” and “are independently” and “are independently selected from” can be interchanged, and should be understood in a broad sense, which can either refer to In different groups, the specific options expressed between the same symbols do not affect each other, and it can also mean that in the same group, the specific options expressed between the same symbols do not affect each other.
  • each q is independently 0, 1, 2 or 3
  • each R" is independently selected from hydrogen, deuterium, fluorine, chlorine
  • formula Q-1 represents that there are q substituents R" on the benzene ring.
  • each R" can be the same or different, and the options of each R" do not affect each other;
  • formula Q-2 indicates that each benzene ring of biphenyl has q substituents R", and the R" on the two benzene rings The number q of "substituents" can be the same or different, each R" can be the same or different, and the options of each R" do not affect each other.
  • substituted or unsubstituted means that the functional group described after the term may or may not have a substituent (hereinafter, for the convenience of description, the substituents are collectively referred to as Rc).
  • substituted or unsubstituted aryl refers to an aryl group having a substituent Rc or an unsubstituted aryl group.
  • substituent namely Rc
  • Rc can be, for example, deuterium, halogen group, cyano group, heteroaryl group with 3-20 carbon atoms, optionally independently selected from 0, 1, 2, 3, 4 or 5
  • two adjacent Ris form an aromatic ring means that any two adjacent Ris may form an aromatic ring, or may not form a ring.
  • the ring may be an unsaturated 6-14 membered aromatic ring , such as benzene ring, naphthalene ring, phenanthrene ring, etc., but not limited thereto.
  • the number of carbon atoms of a substituted or unsubstituted functional group refers to the number of all carbon atoms. For example, if L1 is selected from a substituted arylene group having 12 carbon atoms, then all carbon atoms in the arylene group and the substituents thereon are 12. For example: R 6 is Then the number of carbon atoms is 7; L 2 is Its carbon number is 12.
  • aryl refers to an optional functional group or substituent derived from an aromatic carbocyclic ring.
  • Aryl groups can be monocyclic aryl groups (eg, phenyl) or polycyclic aryl groups, in other words, aryl groups can be monocyclic aryl groups, fused-ring aryl groups, two or more monocyclic aryl groups conjugated through carbon-carbon bonds. Cyclic aryl groups, monocyclic aryl groups and fused-ring aryl groups linked by carbon-carbon bond conjugation, two or more fused-ring aryl groups linked by carbon-carbon bond conjugation. That is, unless otherwise specified, two or more aromatic groups linked by carbon-carbon bond conjugation may also be considered aryl groups in the present application.
  • the fused ring aryl group may include, for example, a bicyclic fused aryl group (eg, naphthyl), a tricyclic fused aryl group (eg, phenanthrenyl, fluorenyl, anthracenyl), and the like.
  • the aryl group does not contain heteroatoms such as B, N, O, S, P, Se and Si.
  • biphenyl, terphenyl, etc. are aryl groups.
  • aryl groups may include, but are not limited to, phenyl, naphthyl, fluorenyl, anthracenyl, phenanthryl, biphenyl, terphenyl, tetraphenyl, pentaphenyl, benzo[9,10] phenanthryl, pyrenyl, benzofluoranthene, Base et al.
  • substituted or unsubstituted aryl group may contain 6-30 carbon atoms, in some embodiments, the number of carbon atoms in the substituted or unsubstituted aryl group may be 6-25, in other implementations The number of carbon atoms in the substituted or unsubstituted aryl group in the examples may be 6-18, and the number of carbon atoms in the substituted or unsubstituted aryl group in other embodiments may be 6-13.
  • the number of carbon atoms of a substituted or unsubstituted aryl group can be 6, 12, 13, 14, 15, 18, 20, 24, 25, 30 , 31, 32, 33, 34, 35, 36 or 40, of course, the number of carbon atoms may also be other numbers, which will not be listed here.
  • biphenyl can be understood as a phenyl substituted aryl group, and can also be understood as an unsubstituted aryl group.
  • the arylene group referred to refers to a divalent group formed by the further loss of one hydrogen atom from the aryl group.
  • the substituted aryl group may be one or more hydrogen atoms in the aryl group replaced by a group such as a deuterium atom, a halogen group, a cyano group, an aryl group, a heteroaryl group, a trialkylsilyl group, an alkyl group, Cycloalkyl, alkoxy, alkylthio and other groups are substituted.
  • a group such as a deuterium atom, a halogen group, a cyano group, an aryl group, a heteroaryl group, a trialkylsilyl group, an alkyl group, Cycloalkyl, alkoxy, alkylthio and other groups are substituted.
  • heteroaryl-substituted aryl groups include, but are not limited to, dibenzofuranyl-substituted phenyl groups, dibenzothiophene-substituted phenyl groups, pyridine-substituted pheny
  • the number of carbon atoms in a substituted aryl group refers to the total number of carbon atoms in the aryl group and the substituents on the aryl group, for example, a substituted aryl group with a carbon number of 18 refers to the aryl group and its substituents.
  • the total number of carbon atoms of the substituents is 18.
  • aryl groups as substituents include but are not limited to: phenyl, naphthyl, anthracenyl, phenanthryl, dimethylfluorenyl, biphenyl, diphenylfluorenyl, spirobifluorene base, triphenylene, etc.
  • the fluorenyl group can be substituted, and the two substituent groups can be combined with each other to form a spiro structure.
  • Specific examples include but are not limited to the following structures:
  • a heteroaryl group refers to a monovalent aromatic ring or a derivative thereof containing at least one heteroatom in the ring, and the heteroatom may be at least one of B, O, N, P, Si, Se and S.
  • a heteroaryl group can be a monocyclic heteroaryl group or a polycyclic heteroaryl group, in other words, a heteroaryl group can be a single aromatic ring system or multiple aromatic ring systems linked by carbon-carbon bonds, and any aromatic The ring system is an aromatic monocyclic ring or an aromatic fused ring.
  • heteroaryl groups can include thienyl, furyl, pyrrolyl, imidazolyl, thiazolyl, oxazolyl, oxadiazolyl, triazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, acridinyl, pyridazinyl, pyrazinyl, quinolinyl, quinazolinyl, quinoxalinyl, phenoxazinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl Azinyl, isoquinolinyl, indolyl, carbazolyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothienyl, dibenzothienyl, thiophene thieny
  • thienyl, furyl, phenanthroline, etc. are heteroaryl groups of a single aromatic ring system type
  • N-arylcarbazolyl and N-heteroarylcarbazolyl are polycarbazolyl groups conjugated through carbon-carbon bonds.
  • Heteroaryl of ring system type is the same as thienyl, furyl, phenanthroline, etc.
  • the "substituted or unsubstituted heteroaryl" of the present application may contain 3-30 carbon atoms, in some embodiments, the number of carbon atoms in the substituted or unsubstituted heteroaryl may be 3-25, in other In the embodiments, the number of carbon atoms in the substituted or unsubstituted heteroaryl group may be 3-20, and in other embodiments, the number of carbon atoms in the substituted or unsubstituted aryl group may be 12-20.
  • the number of carbon atoms can be 3, 4, 5, 7, 12, 13, 18, 20, 24, 25 or 30, of course, the number of carbon atoms can also be other The number will not be listed here.
  • the heteroarylene group referred to refers to a divalent group formed by the further loss of one hydrogen atom from the heteroaryl group.
  • a substituted heteroaryl group may be a heteroaryl group in which one or more than two hydrogen atoms are replaced by, for example, a deuterium atom, a halogen group, a cyano group, an aryl group, a heteroaryl group, a trialkylsilyl group, an alkane group group, cycloalkyl, alkoxy, alkylthio and other groups.
  • aryl-substituted heteroaryl groups include, but are not limited to, phenyl-substituted dibenzofuranyl, phenyl-substituted dibenzothienyl, N-phenylcarbazolyl, and the like. It should be understood that the number of carbon atoms in a substituted heteroaryl group refers to the total number of carbon atoms in the heteroaryl group and the substituents on the heteroaryl group.
  • heteroaryl groups as substituents include but are not limited to: pyridyl, dibenzofuranyl, dibenzothienyl, carbazolyl, N-phenylcarbazolyl, phenanthroline base, benzoxazolyl, and the like.
  • R 6 , R 7 , R 8 and R 9 are connected to each other to form an aromatic ring with 6-14 carbon atoms
  • R 6 and R 7 , R 7 and R 8 or R 8 and R 9 may form a ring with each other.
  • the number of carbon atoms in the formed ring is 6-14, and the ring is an aromatic ring, such as a benzene ring, a naphthalene ring, a phenanthrene ring, and an anthracene ring.
  • the unpositioned linker 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 through which the bond runs, and the other end is connected to the rest of the compound molecule.
  • the naphthyl group represented by the formula (f) is connected to other positions of the molecule through two non-positioned linkages running through the bicyclic ring. -1) to any possible connection method shown in formula (f-10).
  • the phenanthrene represented by the formula (X') is connected to other positions of the molecule through a non-positioned link extending from the middle of one side of the benzene ring, which represents The meaning of , includes any possible connection modes shown by formula (X'-1) to formula (X'-4).
  • a non-positioned substituent in the present application refers to a substituent attached through a single bond extending from the center of the ring system, which means that the substituent may be attached at any possible position in the ring system.
  • the substituent R' represented in the formula (Y) is connected to the quinoline ring through a non-positioning linkage, and the meanings represented by it include such as the formula (Y-1) ⁇ Any possible connection mode shown by formula (Y-7).
  • the alkyl group having 1 to 10 carbon atoms may include a straight-chain alkyl group having 1 to 10 carbon atoms and a branched alkyl group having 3 to 10 carbon atoms.
  • the number of carbon atoms may be, for example, 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10.
  • alkyl group having 1 to 10 carbon atoms include, but are not limited to, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl base, neopentyl, n-hexyl, n-heptyl, n-octyl, 2-ethylhexyl, nonyl, decyl.
  • the number of carbon atoms of the cycloalkyl group having 3 to 10 carbon atoms may be, for example, 3, 5, 6, 7, 8, 9, or 10.
  • Specific examples of the cycloalkyl group having 3 to 10 carbon atoms include, but are not limited to, cyclopentyl, cyclohexyl, adamantyl.
  • a halogen group can be, for example, fluorine, chlorine, bromine, iodine.
  • trialkylsilyl include, but are not limited to, trimethylsilyl, triethylsilyl, and the like.
  • triarylsilyl group examples include, but are not limited to, triphenylsilyl and the like.
  • the organic compound may have the structure shown in any one of Formula 1-1 to Formula 1-18:
  • the ring A is selected from the group consisting of:
  • the ring A is selected from the group consisting of:
  • Ar 1 and Ar 2 are independently selected from unsubstituted arylene groups with 6-14 carbon atoms, unsubstituted heteroarylene groups with 3-16 carbon atoms .
  • Ar 1 and Ar 2 are each independently selected from the following groups:
  • L 1 and L 2 are independently selected from a single bond, a substituted or unsubstituted arylene group having 6-12 carbon atoms, a substituted or unsubstituted arylene group having 12-18 carbon atoms, or a single bond. Unsubstituted heteroarylene.
  • L 1 and L 2 are independently selected from single bond, substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted phenanthrene, Substituted or unsubstituted anthracylene, substituted or unsubstituted biphenylene, substituted or unsubstituted carbazole, substituted or unsubstituted N-phenylcarbazolylidene.
  • the substituents in L 1 and L 2 are each independently selected from: deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, phenyl, naphthalene base.
  • L 1 and L 2 are independently selected from a single bond or a substituted or unsubstituted group T 1 , and the unsubstituted group T 1 is selected from the group consisting of the following groups:
  • the substituents in the substituted group T 1 are each independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, phenyl, and naphthyl.
  • the L 1 and L 2 are independently selected from the group consisting of a single bond or the following groups:
  • Ar is selected from a substituted or unsubstituted aryl group with 6-25 carbon atoms, and a substituted or unsubstituted heteroaryl group with 5-20 carbon atoms.
  • the substituents in the Ar are selected from deuterium, fluorine, cyano, alkyl groups with 1-5 carbon atoms, aryl groups with 6-20 carbon atoms, and aryl groups with 5-18 carbon atoms. Heteroaryl.
  • substituents in Ar include but are not limited to: deuterium, fluorine, cyano, n-propyl, isopropyl, tert-butyl, phenyl, naphthyl, biphenyl, dimethylfluorene phenyl, phenanthryl, anthracenyl, terphenyl, pyridyl, dibenzofuranyl, dibenzothienyl, carbazolyl, N-phenylcarbazolyl, and the like.
  • Ar is selected from a substituted or unsubstituted group T 2 , and the unsubstituted group T 2 is selected from the group consisting of:
  • the substituted group T 2 has one or more substituents, and the substituents of the substituted T 2 are each independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl base, phenyl, naphthyl, biphenyl, phenanthryl, terphenyl.
  • the Ar is selected from the group consisting of the following groups:
  • R 3 , R 4 and R 5 are the same or different, and are each independently selected from deuterium, cyano, halogen, alkyl with 1-10 carbon atoms, carbon Aryl having 6-12 atoms.
  • R 3 , R 4 and R 5 include, but are not limited to: deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, phenyl, naphthyl, Biphenyl.
  • substituted or unsubstituted groups G are independently selected from substituted or unsubstituted groups G, wherein unsubstituted groups G are selected from the group consisting of:
  • the substituted group G has one or more substituents, each of which is independently selected from: deuterium, cyano, fluorine, methyl, ethyl, n-propyl, isopropyl, tertiary Butyl, phenyl, naphthyl, biphenyl, phenanthrenyl, dibenzofuranyl, dibenzothienyl, dimethylfluorenyl, benzoxazolyl, N-phenylcarbazolyl, carbazole group; when the number of substituents in group G is greater than 1, each substituent is the same or different.
  • the, are each independently selected from the group consisting of:
  • the organic compound is selected from the group consisting of the following compounds:
  • the synthesis method of the organic compounds provided in this application is not particularly limited, and those skilled in the art can determine a suitable synthesis method according to the preparation methods provided in the organic compounds combined with the synthesis examples section of the application.
  • the Synthesis Examples section of the present application exemplarily provides methods for preparing organic compounds, and the raw materials used can be obtained commercially or by methods well known in the art.
  • Those skilled in the art can obtain all the organic compounds provided in the present application according to these exemplary preparation methods, and all specific preparation methods for preparing the organic compounds will not be described in detail here, and those skilled in the art should not interpret the present application as a limitation.
  • a second aspect of the present application provides an organic electroluminescent device, comprising an anode and a cathode disposed opposite to each other, and a functional layer disposed between the anode and the cathode; the functional layer comprises the first aspect of the present application. the mentioned organic compounds.
  • the organic compounds provided in the present application can be used to form at least one organic film layer in the functional layer, so as to improve the efficiency characteristics and lifetime characteristics of electronic components.
  • the organic electroluminescent device may be, for example, a green organic electroluminescent device. As shown in FIG. 1 , 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 serving as an energy conversion layer, and an electron transport layer 340 , which are stacked in sequence. and cathode 200.
  • the anode 100 includes an anode material, which is preferably a material with a large work function that facilitates hole injection into the functional layer.
  • anode materials include: metals such as nickel, platinum, vanadium, chromium, copper, zinc and gold or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO) and indium zinc oxide (IZO); Combined metals and oxides such as ZnO:Al or SnO2 :Sb; or conducting polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene ](PEDT), polypyrrole and polyaniline, but not limited thereto. It is preferable to include a transparent electrode comprising indium tin oxide (ITO) as an anode.
  • ITO indium tin oxide
  • the first hole transport layer 321 and the second hole transport layer 322 respectively include one or more hole transport materials, and the hole transport materials can be selected from carbazole polymers, carbazole-linked triarylamines Compounds or other types of compounds are not specifically limited in this application.
  • the first hole transport layer 321 may be composed of the compound NPB.
  • the first hole transport layer is composed of HT-01
  • the second hole transport layer 322 is composed of HT-02.
  • the organic light-emitting layer 330 may be composed of a single light-emitting material, or may include a host material and a guest material.
  • the host material and/or the guest material of the organic light-emitting layer may contain the organic compound of the present application.
  • the organic light-emitting layer 330 may be composed of a single light-emitting material, or may include a host material and a guest material.
  • the host material of the organic light-emitting layer may contain the organic compound of the present application.
  • 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, the host material transfers energy to the guest material, thereby enabling the guest material to emit light.
  • 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, which are not specially made in this application. limit.
  • the organic electroluminescent device is a green light-emitting device, wherein the organic light-emitting layer includes a host material and a guest material, wherein the host material is a dual-host light-emitting material, that is, includes a p-type light-emitting material Host material and n-type host material, the organic compound of the present application can be used as both p-type host material and n-type host material.
  • the host material of the organic light-emitting layer contains the organic compound of the present application.
  • the electron transport layer 340 may be a single-layer structure or a multi-layer structure, which may include one or more electron transport materials, and the electron transport materials may be selected from, but not limited to, benzimidazole derivatives, oxadiazole derivatives , quinoxaline derivatives or other electron transport materials.
  • the electron transport layer 340 may be composed of ET-01 and LiQ.
  • the cathode 200 may include a cathode material, which is a material with a small work function that facilitates electron injection into the functional layer.
  • cathode materials include, but are not limited to, metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead or alloys thereof; or multi-layer materials such as LiF/Al , Liq/Al, LiO 2 /Al, LiF/Ca, LiF/Al and BaF 2 /Ca.
  • a metal electrode comprising magnesium and silver is preferably included as the cathode.
  • a hole injection layer 310 may be further disposed between the anode 100 and the first hole transport layer 321 to enhance the capability of injecting 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, which are not specifically limited in this application.
  • the hole injection layer 310 may be composed of F4-TCNQ.
  • an electron injection layer 350 may also be disposed between the cathode 200 and the electron transport layer 340 to enhance the capability of injecting electrons into the electron transport layer 340 .
  • the electron injection layer 350 may include inorganic materials such as alkali metal sulfide and alkali metal halide, or may include a complex compound of alkali metal and organic matter.
  • the electron injection layer 350 may include LiQ.
  • a third aspect of the present application provides an electronic device including the organic electroluminescent device described in the second aspect of the present application.
  • the electronic device is an electronic device 400
  • the electronic device 400 includes the above-mentioned organic electroluminescence device.
  • the electronic device 400 may be, for example, a display device, a lighting device, an optical communication device, or other types of electronic devices, such as but not limited to computer screens, mobile phone screens, televisions, electronic paper, emergency lighting, light modules, and the like.
  • Anhydrous tetrahydrofuran, dioxane, toluene and diethyl ether are obtained by refluxing and drying with metallic sodium.
  • Anhydrous dichloromethane and chloroform were obtained by refluxing with calcium hydride.
  • Ethyl acetate, petroleum ether, n-hexane, N,N-dimethylacetamide and N,N-dimethylformamide were previously dried over anhydrous sodium sulfate and used.
  • reaction flasks are plugged with suitable rubber stoppers, and the substrate is injected through a syringe. Glassware is dry.
  • the chromatographic column is a silica gel column.
  • Silica gel 300-400 mesh was purchased from Qingdao Ocean Chemical Factory.
  • the measurement conditions for low-resolution mass spectrometry (MS) data are: Agilent 6120 quadrupole HPLC-M (column model: Zorbax SB-C18, 2.1 ⁇ 30 mm, 3.5 ⁇ m, 6 min, flow rate 0.6 mL/min.
  • Mobile phase 5 % - 95% ( CH3CN with 0.1% formic acid) in ( H2O with 0.1% formic acid) using electrospray ionization (ESI) at 210 nm/254 nm with UV detection.
  • ESI electrospray ionization
  • Phenylboronic acid (20.0 g; 164.0 mmol), 1,3-dibromo-5-iodobenzene (65.3 g; 180.4 mmol), tetrakis(triphenylphosphine)palladium (3.8 g; 3.3 mmol), tetrabutyl bromide
  • Ammonium chloride (10.6 g; 32.8 mmol), potassium carbonate (49.9 g; 360.9 mmol), toluene (320 mL), ethanol (80 mL) and deionized water (80 mL) were added to a round-bottomed flask under nitrogen protection, and the temperature was raised under stirring conditions to 55-60°C for 8 hours; then the reaction mixture was cooled to room temperature, deionized water was added, stirred for 10 minutes, the organic phase was separated, dried by adding anhydrous magnesium sulfate, and the solvent was removed under reduced pressure; the crude product obtained was used in n-heptane Silica
  • Phenylboronic acid (35.0 g; 287.0 mmol), 3-chloro-4-fluorobromobenzene (60.1 g; 287.0 mmol), tetrakis(triphenylphosphine)palladium (6.6 g; 5.7 mmol), tetrabutylammonium bromide (18.5 g; 57.4 mmol), potassium carbonate (87.3 g; 637.5 mmol), toluene (280 mL), ethanol (70 mL) and deionized water (70 mL) were added to a round-bottomed flask under nitrogen protection, and the temperature was raised to 75 under stirring conditions.
  • the reactant P in the following table 10 replaces the intermediate b3c1d1, and the intermediate shown in the following table 10 is synthesized:
  • Methylacetamide (300mL) solution was then incubated for 48h, cooled to room temperature, toluene was added to the reaction solution and washed with a large amount of deionized water, the organic phase was separated and dried over anhydrous magnesium sulfate, the solvent was removed under reduced pressure, and the obtained crude product was used Purification by silica gel column chromatography using dichloromethane/n-heptane as an eluent, followed by recrystallization and purification using toluene/n-heptane as a solvent, gave compound A16 (3.8 g; 34%) as a white solid.
  • the anode is prepared by the following process: the thickness is The ITO substrate (manufactured by Corning) was cut into a size of 40mm ⁇ 40mm ⁇ 0.7mm, and a photolithography process was used to prepare it into an experimental substrate with patterns of cathodes, anodes and insulating layers. Ultraviolet ozone and O 2 :N 2 plasma were used for Surface treatment to increase the work function of the anode (experimental substrate) and remove scum.
  • HIL hole injection layer
  • HT-02 was vacuum evaporated on the first hole transport layer to form a thickness of the second hole transport layer.
  • compound A2:GH-n1:Ir(ppy) 3 was co-evaporated at a weight ratio of 50%:45%:5% to form a thickness of green organic light-emitting layer (EML).
  • EML green organic light-emitting layer
  • ET-01 and LiQ were mixed at a weight ratio of 1:1 and evaporated to form Thick electron transport layer (ETL), LiQ was evaporated on the electron transport layer to form a thickness of The electron injection layer (EIL) of the the cathode.
  • ETL Thick electron transport layer
  • EIL electron injection layer
  • the thickness of the vapor deposition on the above-mentioned cathode is The CP-1 is formed to form an organic capping layer (CPL), thereby completing the fabrication of the organic light-emitting device.
  • CPL organic capping layer
  • An organic electroluminescent device was fabricated by the same method as in Example 1, except that the compounds shown in Table 14 below were used in place of Compound A2 in forming the organic light-emitting layer.
  • An organic electroluminescent device was fabricated by the same method as in Example 1, except that GH-p1 was used instead of Compound A2 and the compounds shown in Table 14 below were used instead of GH-n1 in forming the organic light-emitting layer.
  • An organic electroluminescent device was fabricated by the same method as in Example 1, except that GH-p1 was used instead of compound A2 in forming the organic light-emitting layer.
  • An organic electroluminescent device was fabricated by the same method as in Example 1, except that Compound I shown in the following table was substituted for Compound A2 in forming the organic light-emitting layer.
  • An organic electroluminescent device was fabricated by the same method as in Example 1, except that GH-p1 was used instead of Compound A2 and Compound II was used instead of GH-n1 when forming the organic light-emitting layer.
  • An organic electroluminescent device was fabricated in the same manner as in Example 1, except that GH-p1 was used instead of Compound A2 and Compound III was used instead of GH-n1 when forming the organic light-emitting layer.
  • the compounds of the present application are used as the hole-type host material in the mixed host material of the green light-emitting layer.
  • the luminous efficiency and life of the device have been significantly improved; and Compared with Comparative Example 2, the lifespan was greatly improved.
  • the organic electroluminescent devices prepared by using the compounds of the present application in Examples 1-11 have a lifetime increased by at least 22.67% and a luminous efficiency Cd/A increased by at least 10.2%.
  • the compounds of the present application were used as the electronic host material in the mixed host material of the green light-emitting layer.
  • the luminous efficiency and life of the device were significantly improved; Under the premise of similar device lifetimes, the luminous efficiency has been significantly improved; the reason may be the higher carrier and energy transfer efficiency caused by the rigid structure of the compound of the present application; compared with Comparative Example 4 , under the premise of similar device luminous efficiency, the lifetime has been greatly improved.
  • the organic electroluminescent devices prepared by the compounds of the present application in Examples 12-25 have a lifetime increased by at least 12.4%, a luminous efficiency Cd/A increased by at least 10.5%, and an external quantum efficiency. EQE improved by at least 9.9%.
  • the novel compound of the present application when used to prepare a green organic electroluminescent device, the luminous efficiency of the organic electroluminescent device can be effectively improved and its lifespan can be prolonged.

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Abstract

本申请涉及一种有机化合物以及使用其的有机电致发光器件和电子装置，所述有机化合物的结构如式I所示。本申请的有机化合物用于有机电致发光器件的有机发光层时，可以有效地提升器件的器件效率，并延长有机电致发光器件的寿命

Description

有机化合物以及使用其的有机电致发光器件和电子装置
相关申请的交叉引用
本申请要求于2020年11月19日递交的申请号为CN202011303761.6的中国专利申请的优先权，在此引用上述中国专利申请的内容全文以作为本申请的一部分。
技术领域
本申请属于有机材料技术领域，具体提供一种有机化合物以及使用其的有机电致发光器件和电子装置。
背景技术
随着电子技术的发展和材料科学的进步，用于实现电致发光或者光电转化的电子元器件的应用范围越来越广泛。该类电子元器件通常包括相对设置的阴极和阳极，以及设置于阴极和阳极之间的功能层。该功能层由多层有机或者无机膜层组成，且一般包括能量转化层、位于能量转化层与阳极之间的空穴传输层、位于能量转化层与阴极之间的电子传输层。
以有机电致发光器件为例，其一般包括依次层叠设置的阳极、空穴传输层、作为能量转化层的电致发光层、电子传输层和阴极。当阴阳两极施加电压时，两电极产生电场，在电场的作用下，阴极侧的电子向电致发光层移动，阳极侧的空穴也向发光层移动，电子和空穴在电致发光层结合形成激子，激子处于激发态向外释放能量，进而使得电致发光层对外发光。
目前，对于绿色有机电致发光器件而言，仍存在驱动电压过高、低发光效率和寿命短的问题，从而导致器件性能下降。因此，有必要研发新型的材料，以进一步提高电子元器件的性能。
发明内容
本申请的目的在于提供一种有机化合物以进一步提高有机电致发光器件的性能。
为了实现上述目的，本申请的第一个方面提供了一种有机化合物，所述有机化合物的结构如式I所示：
Figure PCTCN2021111341-appb-000001
其中，环A选自式A所示的基团：
Figure PCTCN2021111341-appb-000002
Figure PCTCN2021111341-appb-000003
表示与Ar 1、Ar 2键合；
R 6、R 7、R 8和R 9分别独立地选自氢、氘、碳原子数为6-30的取代或未取代的芳基、碳原子数为6-30的取代或未取代的杂芳基；
或者任选地，R 6、R 7、R 8、R 9中两个相邻基团相互连接形成碳原子数为6-14的芳环；
Ar 1和Ar 2分别独立地选自碳原子数为6-20的未取代的亚芳基、碳原子数为3-20的未取代的亚杂芳基；
R 1和R 2相同或不同，且各自独立地选自氢、氘、卤素基团、氰基、碳原子数为1-30的烷基、碳原子数为3-30的环烷基、碳原子数为1-30的烷氧基、碳原子数为3-12的三烷基硅基、碳原子数为18-24的三芳基硅基或式B所示的结构；
Figure PCTCN2021111341-appb-000004
L 1和L 2相同或不同，且分别独立地选自单键、碳原子数为6-30的取代或未取代的亚芳基、碳原子数为3-30的取代或未取代的亚杂芳基；
Ar选自碳原子数为6-30的取代或未取代的芳基、碳原子数为3-30的取代或未取代的杂芳基；
R 3、R 4和R 5相同或不同，且各自独立地选自氘、卤素基团、氰基、碳原子数为1-10的烷基、碳原子数为6-20的芳基、碳原子数为3-20的杂芳基；
n 3表示R 3的个数，n 4表示R 4的个数，n 5表示R 5的个数；
n 3选自：0、1、2、3或4；
n 4选自：0、1或2；
n 5选自：0、1、2、3或4；
R 6、R 7、R 8、R 9、L 1、L 2和Ar中的取代基各自独立地选自氘，卤素基团，氰基，碳原子数为3-20的杂芳基，任选地被0、1、2、3、4或5个独立地选自氘、氟、氰基、甲基、叔丁基的取代基所取代的碳原子数为6-20的芳基，碳原子数为3-12的三烷基硅基，碳原子数为18-24的三芳基硅基，碳原子数为1-10的烷基，碳原子数为1-10的卤代烷基，碳原子数为3-10的环烷基，碳原子数为2-10的杂环烷基。
本申请的第二方面提供了一种有机电致发光器件，所述电子元件包括相对设置的阳极和阴极，以及设于所述阳极和所述阴极之间的功能层；所述功能层包含本申请第一方面所述的有机化合物；
优选地，所述功能层包括有机发光层，所述有机发光层包含所述有机化合物；
更优选地，所述有机发光层包含主体材料，所述主体材料含有所述的有机化合物。
本申请的第三方面提供了一种电子装置，所述电子装置包括本申请第二方面所述的有机电致发光器件。
通过上述技术方案，本申请的化合物具有以下特点：
1、本申请的化合物以吲哚并[2,3-a]咔唑作为核心基团，在其N和N’位置共同连接三个芳香性环体系而形成大环结构；此结构中吲哚并[2,3-a]咔唑基团具有高的第一三重态能级和优秀的能量传输特性。三个芳香性环体系通过单键互相连接而成的大环结构同时具有扭曲的结构和高的刚性，在保持化合物高的第一三重态能级的前提下，同时具有低重组能带来的高的载流子迁移率特性，好的激子能量传输特性，以及降低分子间堆叠而产生的好的材料成膜性能；并且通过不同的亚芳基或亚杂芳基和连接其上的取代基的种类的调整，可以方便地调节分子的能级和物理特性。
2、本申请化合物的大环结构中第二个连接基团(与吲哚并[2,3-a]咔唑不直接相连的环A基团)为邻位相连接的亚芳基，从而最大程度上降低了连接基团之间单键形变以及大环的张力，使得本申请化合物具有更高的热力学和化学稳定性。将本申请的化合物用于有机电致发光器件的有机发光层时，可以在维持较低驱动电压的前提下，有效提升器件的发光效率和寿命。
本申请的其他特征和优点将在随后的具体实施方式部分予以详细说明。
附图说明
附图是用来提供对本申请的进一步理解，并且构成说明书的一部分，与下面的具体实施方式一起用于解释本申请，但并不构成对本申请的限制。在附图中：
图1是本申请一种实施方式的有机电致发光器件的结构示意图。
图2是本申请一种实施方式的电子装置的结构示意图。
附图标记说明
100、阳极；200、阴极；300、功能层；310、空穴注入层；320、空穴传输层；321、第一空穴传输层；322、第二空穴传输层；330、有机发光层；340、电子传输层；350、电子注入层；400、电子装置。
具体实施方式
以下对本申请的具体实施方式进行详细说明。应当理解的是，此处所描述的具体实施方式仅用于说明和解释本申请，并不用于限制本申请。
本申请的第一个方面提供了一种有机化合物，所述有机化合物的结构如式I所示：
Figure PCTCN2021111341-appb-000005
其中，环A选自式A所示的基团：
Figure PCTCN2021111341-appb-000006
Figure PCTCN2021111341-appb-000007
表示与Ar 1、Ar 2键合，即环A与Ar 1、Ar 2连接的化学键；
R 6、R 7、R 8和R 9分别独立地选自氢、氘、碳原子数为6-30的取代或未取代的芳基、碳原子数为6-30的取代或未取代的杂芳基；
或者任选地，R 6、R 7、R 8、R 9中相邻的两个相互连接形成碳原子数为6-14的芳环；
Ar 1和Ar 2分别独立地选自碳原子数为6-20的未取代的亚芳基、碳原子数为3-20的未取代的亚杂芳基；
R 1和R 2相同或不同，且各自独立地选自氢、氘、卤素基团、氰基、碳原子数为1-30的烷基、碳原子数为3-30的环烷基、碳原子数为1-30的烷氧基、碳原子数为3-12的三烷基硅基、碳原子数为18-24的三芳基硅基或式B所示的结构；
Figure PCTCN2021111341-appb-000008
Figure PCTCN2021111341-appb-000009
L 1和L 2相同或不同，且分别独立地选自单键、碳原子数6-30的取代或未取代的亚芳基、碳原子数为3-30的取代或未取代的亚杂芳基；
Ar选自碳原子数为6-30的取代或未取代的芳基、碳原子数为3-30的取代或未取代的杂芳基；
R 3、R 4和R 5相同或不同，且各自独立地选自氘、卤素基团、氰基、碳原子数为1-10的烷基、碳原子数为6-20的芳基、碳原子数为3-20的杂芳基；
n 3表示R 3的个数，n 4表示R 4的个数，n 5表示R 5的个数；
n 3选自：0、1、2、3或4；
n 4选自：0、1或2；
n 5选自：0、1、2、3或4；
R 6、R 7、R 8、R 9、L 1、L 2和Ar中的取代基各自独立地选自氘，卤素基团，氰基，碳原子数为3-20的杂芳基，任选地被0、1、2、3、4或5个独立地选自氘、氟、氰基、甲基、叔丁基的取代基所取代的碳原子数为6-20的芳基，碳原子数为3-12的三烷基硅基，碳原子数为18-24的三芳基硅基，碳原子数为1-10的烷基，碳原子数为1-10的卤代烷基，碳原子数为3-10的环烷基，碳原子数为2-10的杂环烷基。
在本申请中，术语“任选”、“任选地”意味着随后所描述的事件或者环境可以但不必发生，该说明包括该事情或者环境发生或者不发生的场合。例如，“任选地，两个相邻取代基××形成环；”意味着这两个取代基可以形成环但不是必须形成环，包括：两个相邻的取代基形成环的情景和两个相邻的取代基不形成环的情景。
在本申请中，“任选地被0、1、2、3、4或5个独立选自氘、氟、氰基、甲基、叔丁基的取代基所取代的碳原子数为6-20的芳基”是指芳基可以被氘、氟、氰基、甲基、叔丁基中的一个或多个取代，也可以不被氘、氟、氰基、甲基、叔丁基取代，且当芳基上的取代基的个数大于等于2时，取代基可以相同或不同。
本申请中，所采用的描述方式“各……独立地为”与“……分别独立地为”和“……独立地选自”可以互换，均应做广义理解，其既可以是指在不同基团中，相同符号之间所表达的具体选项之间互相不影响，也可以表示在相同的基团中，相同符号之间所表达的具体选项之间互相不影响。例如，“
Figure PCTCN2021111341-appb-000010
其中，各q独立地为0、1、2或3，各R”独立地选自氢、氘、氟、氯”，其含义是：式Q-1表示苯环上有q个取代基R”，各个R”可以相同也可以不同，每个R”的选项之间互不影响；式Q-2表示联苯的每一个苯环上有q个取代基R”，两个苯环上的R”取代基的个数q可以相同或不同，各个R”可以相同也可以不同，每个R”的选项之间互不影响。
在本申请中，“取代或未取代的”这样的术语是指，在该术语后面记载的官能团可以具有或不具有取代基(下文为了便于描述，将取代基统称为Rc)。例如，“取代或未取代的芳基”是指具有取代基Rc的芳基或者非取代的芳基。其中上述的取代基即Rc例如可以为氘，卤素基团，氰基，碳原子数为3-20的杂芳基，任选地被0、1、2、3、4或5个独立地选自氘、氟、氰基、甲基、叔丁基的取代基所取代的碳原子数为6-20的芳基，碳原子数为3-12的三烷基硅基，碳原子数为18-24的三芳基硅基，碳原子数为1-10的烷基，碳原子数为1-10的卤代烷基，碳原子数为3-10的环烷基，碳原子数为2-10的杂环烷基。
在本申请中，表述“两个所述取代基相互连接以与它们所连接的原子一起形成环”中，其中，当同一个原子上具有两个取代基时，两个取代基可以与其共同连接的该原子形成饱和或不饱和的环(例如，3-18元的饱和或不饱和环)；当两个相邻的原子上分别具有一个取代基时，这两个取代 基可以稠合成环。
在本申请中，“任选地，Ri中相邻的两个形成芳环”是指任意两个相邻的Ri可以形成芳环，也可以不形成环。举例而言，当相邻的R 6和R 7、相邻的R 7与R 8、相邻的两个R 8与R 9成环时，该环可以是不饱和的6-14元芳环，例如苯环、萘环、菲环等，但不限于此。
在本申请中，取代或未取代的官能团的碳原子数，指的是所有碳原子数。举例而言，若L 1选自碳原子数为12的取代的亚芳基，则亚芳基及其上的取代基的所有碳原子数为12。例如：R 6为
Figure PCTCN2021111341-appb-000011
则其碳原子数为7；L 2为
Figure PCTCN2021111341-appb-000012
其碳原子数为12。
在本申请中，芳基指的是衍生自芳香碳环的任选官能团或取代基。芳基可以是单环芳基(例如苯基)或多环芳基，换言之，芳基可以是单环芳基、稠环芳基、通过碳碳键共轭连接的两个或者更多个单环芳基、通过碳碳键共轭连接的单环芳基和稠环芳基、通过碳碳键共轭连接的两个或者更多个稠环芳基。即，除非另有说明，通过碳碳键共轭连接的两个或者更多个芳香基团也可以视为本申请的芳基。其中，稠环芳基例如可以包括双环稠合芳基(例如萘基)、三环稠合芳基(例如菲基、芴基、蒽基)等。芳基中不含有B、N、O、S、P、Se和Si等杂原子。举例而言，在本申请中，联苯基、三联苯基等为芳基。芳基的实例可以包括但不限于，苯基、萘基、芴基、蒽基、菲基、联苯基、三联苯基、四联苯基、五联苯基、苯并[9,10]菲基、芘基、苯并荧蒽基、
Figure PCTCN2021111341-appb-000013
基等。本申请的“取代或未取代的芳基”可含有6-30个碳原子，在一些实施例中，取代或未取代的芳基中的碳原子数可以是6-25个，在另一些实施例中取代或未取代的芳基中的碳原子数可以是6-18个，在另一些实施例中取代或未取代的芳基中的碳原子数可以是6-13个。举例而言，本申请中，取代或未取代的芳基的碳原子数量可以是6个、12个、13个、14个、15个、18个、20个、24个、25个、30个、31个、32个、33个、34个、35个、36个或40个，当然，碳原子数还可以是其他数量，在此不再一一列举。在本申请中，联苯基可以理解为苯基取代的芳基，也可以理解为未取代的芳基。
本申请中，涉及的亚芳基是指芳基进一步失去一个氢原子所形成的二价基团。
在本申请中，取代的芳基可以是芳基中的一个或者两个以上氢原子被诸如氘原子、卤素基团、氰基、芳基、杂芳基、三烷基硅基、烷基、环烷基、烷氧基、烷硫基等基团取代。杂芳基取代的芳基的具体实例包括但不限于，二苯并呋喃基取代的苯基、二苯并噻吩取代的苯基、吡啶取代的苯基等。应当理解地是，取代的芳基的碳原子数，指的是芳基和芳基上的取代基的碳原子总数，例如碳原子数为18的取代的芳基，指的是芳基及其取代基的总碳原子数为18。
在本申请中，作为取代基的芳基，具体实例包括但不限于：苯基、萘基、蒽基、菲基、二甲基芴基、联苯基、二苯基芴基、螺二芴基、三亚苯基等等。
在本申请中，芴基可以是取代的，两个取代基可以彼此结合形成螺结构，具体施例包括但不限于以下结构：
Figure PCTCN2021111341-appb-000014
在本申请中，杂芳基是指环中包含至少一个杂原子的一价芳香环或其衍生物，杂原子可以是B、O、N、P、Si、Se和S中的至少一种。杂芳基可以是单环杂芳基或多环杂芳基，换言之，杂芳基可以是单个芳香环体系，也可以是通过碳碳键共轭连接的多个芳香环体系，且任一 芳香环体系为一个芳香单环或者一个芳香稠环。示例地，杂芳基可以包括噻吩基、呋喃基、吡咯基、咪唑基、噻唑基、噁唑基、噁二唑基、三唑基、吡啶基、联吡啶基、嘧啶基、三嗪基、吖啶基、哒嗪基、吡嗪基、喹啉基、喹唑啉基、喹喔啉基、吩噁嗪基、酞嗪基、吡啶并嘧啶基、吡啶并吡嗪基、吡嗪并吡嗪基、异喹啉基、吲哚基、咔唑基、苯并噁唑基、苯并咪唑基、苯并噻唑基、苯并咔唑基、苯并噻吩基、二苯并噻吩基、噻吩并噻吩基、苯并呋喃基、菲咯啉基、异噁唑基、噻二唑基、苯并噻唑基、吩噻嗪基、硅芴基、二苯并呋喃基以及N-芳基咔唑基(如N-苯基咔唑基)、N-杂芳基咔唑基(如N-吡啶基咔唑基)、N-烷基咔唑基(如N-甲基咔唑基)等，而不限于此。其中，噻吩基、呋喃基、菲咯啉基等为单个芳香环体系类型的杂芳基，N-芳基咔唑基、N-杂芳基咔唑基为通过碳碳键共轭连接的多环体系类型的杂芳基。本申请的取代或未取代的杂芳基”可含有3-30个碳原子，在一些实施例中，取代或未取代的杂芳基中的碳原子数可以是3-25个，在另一些实施例中取代或未取代的杂芳基中的碳原子数可以是3-20个，在另一些实施例中取代或未取代的芳基中的碳原子数可以是12-20个。举例而言，其碳原子数量可以是3个、4个、5个、7个、12个、13个、18个、20个、24个、25个或30个，当然，碳原子数还可以是其他数量，在此不再一一列举。
本申请中，涉及的亚杂芳基是指杂芳基进一步失去一个氢原子所形成的二价基团。
在本申请中，取代的杂芳基可以是杂芳基中的一个或者两个以上氢原子被诸如氘原子、卤素基团、氰基、芳基、杂芳基、三烷基硅基、烷基、环烷基、烷氧基、烷硫基等基团取代。芳基取代的杂芳基的具体实例包括但不限于，苯基取代的二苯并呋喃基、苯基取代的二苯并噻吩基、N-苯基咔唑基等。应当理解地是，取代的杂芳基的碳原子数，指的是杂芳基和杂芳基上的取代基的碳原子总数。
在本申请中，作为取代基的杂芳基，具体实例包括但不限于：吡啶基、二苯并呋喃基、二苯并噻吩基、咔唑基、N-苯基咔唑基、菲咯啉基、苯并噁唑基等等。
在本申请中，“R 6、R 7、R 8、R 9中两个相邻基团相互连接形成碳原子数为6-14的芳环”指的是R 6和R 7、R 7和R 8或R 8和R 9可以相互形成环。所形成的环的碳原子数为6-14，且该环为芳环，例如：苯环、萘环、菲环、蒽环。
本申请中，不定位连接键涉及的是从环体系中伸出的单键
Figure PCTCN2021111341-appb-000015
其表示该连接键的一端可以连接该键所贯穿的环体系中的任意位置，另一端连接化合物分子其余部分。
举例而言，如下式(f)中所示地，式(f)所表示的萘基通过两个贯穿双环的不定位连接键与分子其他位置连接，其所表示的含义，包括如式(f-1)～式(f-10)所示出的任一可能的连接方式。
Figure PCTCN2021111341-appb-000016
再举例而言，如下式(X')中所示地，式(X')所表示的菲基通过一个从一侧苯环中间伸出的不定位连接键与分子其他位置连接，其所表示的含义，包括如式(X'-1)～式(X'-4)所示出的任一可能的连接方式。
Figure PCTCN2021111341-appb-000017
本申请中的不定位取代基，指的是通过一个从环体系中央伸出的单键连接的取代基，其表示该取代基可以连接在该环体系中的任何可能位置。例如，如下式(Y)中所示地，式(Y)中所表示的取代基R'通过一个不定位连接键与喹啉环连接，其所表示的含义，包括如式(Y-1)～式(Y-7)所示出的任一可能的连接方式。
Figure PCTCN2021111341-appb-000018
在本申请中，碳原子数为1-10的烷基可以包括碳原子数为1至10的直链烷基和碳原子数为3至10的支链烷基。碳原子数例如可以为1、2、3、4、5、6、7、8、9、10。碳原子数为1-10的烷基的具体实例包括但不限于，甲基、乙基、正丙基、异丙基、正丁基、异丁基、叔丁基、正戊基、异戊基、新戊基、正己基、正庚基、正辛基、2-乙基己基、壬基、癸基。
在本申请中，碳原子数为3-10的环烷基的碳原子数例如可以为3、5、6、7、8、9、10。碳原子数为3-10的环烷基的具体实例包括但不限于，环戊基、环己基、金刚烷基。
在本申请中，卤素基团例如可以为氟、氯、溴、碘。
在本申请中，三烷基硅基的具体实例包括但不限于，三甲基硅基、三乙基硅基等。
在本申请中，三芳基硅基的具体实例包括但不限于，三苯基硅基等。
根据本申请的第一个方面，所述有机化合物可以具有式1-1至式1-18中任意一项所示的结构：
Figure PCTCN2021111341-appb-000019
Figure PCTCN2021111341-appb-000020
在本申请的一种实施方式中，所述环A选自如下基团所组成的组：
Figure PCTCN2021111341-appb-000021
Figure PCTCN2021111341-appb-000022
可选地，所述环A选自如下基团所组成的组：
Figure PCTCN2021111341-appb-000023
在本申请的一种实施方式中，Ar 1和Ar 2分别独立地选自碳原子数为6-14的未取代的亚芳基、碳原子数为3-16的未取代的亚杂芳基。
在本申请另一种实施方式中，Ar 1和Ar 2分别独立地选自以下基团：
Figure PCTCN2021111341-appb-000024
在本申请的一种实施方式中，L 1和L 2分别独立地选自单键、碳原子数为6-12的取代或未取代的亚芳基、碳原子数为12-18的取代或未取代的亚杂芳基。
在本申请另一种实施方式中，L 1和L 2分别独立地选自单键、取代或未取代的亚苯基、取代或未取代的亚萘基、取代或未取代的亚菲基、取代或未取代的亚蒽基、取代或未取代的亚联苯基、取代或未取代的亚咔唑、取代或未取代的N-苯基咔唑基亚基。
可选地，所述L 1和L 2中的取代基各自独立地选自：氘、氟、氰基、甲基、乙基、正丙基、异丙基、叔丁基、苯基、萘基。
在本申请的一种实施方式中，L 1和L 2分别独立地选自单键或取代或未取代的基团T 1，未取代的基团T 1选自如下基团所组成的组：
Figure PCTCN2021111341-appb-000025
其中，取代的基团T 1中的取代基各自独立地选自氘、氟、氰基、甲基、乙基、正丙基、异丙基、叔丁基、苯基、萘基。
可选地，所述L 1和L 2分别独立地选自单键或如下基团组成的组：
Figure PCTCN2021111341-appb-000026
Figure PCTCN2021111341-appb-000027
在本申请的一种实施方式中，Ar选自碳原子数为6-25的取代或未取代的芳基、碳原子数为5-20的取代或未取代的杂芳基。
可选地，所述Ar中的取代基选自氘、氟、氰基、碳原子数为1-5的烷基、碳原子数为6-20的芳基、碳原子数为5-18的杂芳基。
具体地，所述Ar中的取代基具体实例包括但不限于：氘、氟、氰基、正丙基、异丙基、叔丁基、苯基、萘基、联苯基、二甲基芴基、菲基、蒽基、三联苯基、吡啶基、二苯并呋喃基、二苯并噻吩基、咔唑基、N-苯基咔唑基等等。
在本申请的一种实施方式中，Ar选自取代或未取代的基团T 2，未取代的基团T 2选自如下基团所组成的组：
Figure PCTCN2021111341-appb-000028
取代的基团T 2具有一个或两个以上取代基，取代的T 2的取代基各自独立地选自氘、氟、氰基、甲基、乙基、正丙基、异丙基、叔丁基、苯基、萘基、联苯基、菲基、三联苯基。
可选地，所述Ar选自如下基团组成的组：
Figure PCTCN2021111341-appb-000029
Figure PCTCN2021111341-appb-000030
在本申请的一种实施方式中，R 3、R 4和R 5相同或者不相同，且各自独立地选自氘、氰基、卤素基团、碳原子数为1-10的烷基、碳原子数为6-12的芳基。
可选地，R 3、R 4和R 5具体实例包括但不限于：氘、氟、氰基、甲基、乙基、正丙基、异丙基、叔丁基、苯基、萘基、联苯基。
在本申请的一种实施方式中，
Figure PCTCN2021111341-appb-000031
分别独立地选自取代或未取代的基团G，其中未取代的基团G选自如下基团组成的组：
Figure PCTCN2021111341-appb-000032
Figure PCTCN2021111341-appb-000033
其中，
Figure PCTCN2021111341-appb-000034
表示化学键；取代的基团G上具有一个或多个的取代基，所述取代基各自独立地选自：氘、氰基、氟、甲基、乙基、正丙基、异丙基、叔丁基、苯基、萘基、联苯基、菲基、二苯并呋喃基、二苯并噻吩基、二甲基芴基、苯并噁唑基、N-苯基咔唑基、咔唑基；当基团G中的取代基个数大于1时，各取代基相同或不同。
可选地，所述，
Figure PCTCN2021111341-appb-000035
分别独立地选自以下基团组成的组：
Figure PCTCN2021111341-appb-000036
Figure PCTCN2021111341-appb-000037
Figure PCTCN2021111341-appb-000038
在本申请的一种实施方式中，所述有机化合物选自如下化合物组成的组：
Figure PCTCN2021111341-appb-000039
Figure PCTCN2021111341-appb-000040
Figure PCTCN2021111341-appb-000041
Figure PCTCN2021111341-appb-000042
Figure PCTCN2021111341-appb-000043
Figure PCTCN2021111341-appb-000044
Figure PCTCN2021111341-appb-000045
Figure PCTCN2021111341-appb-000046
Figure PCTCN2021111341-appb-000047
本申请对提供的有机化合物的合成方法没有特别限定，本领域技术人员可以根据本申请的有机化合物结合合成例部分提供的制备方法确定合适的合成方法。换言之，本申请的合成例部分示例性地提供了有机化合物的制备方法，所采用的原料可通过商购获得或本领域熟知的方法获得。本领域技术人员可以根据这些示例性的制备方法得到本申请提供的所有有机化合物，在此不再详述制备该有机化合物的所有具体制备方法，本领域技术人员不应理解为对本申请的限制。
本申请的第二方面提供一种有机电致发光器件，包括相对设置的阳极和阴极，以及设于所述阳极和所述阴极之间的功能层；所述功能层包含本申请第一方面所述的有机化合物。
本申请所提供的有机化合物可以用于形成功能层中的至少一个有机膜层，以改善电子元件的效率特性和寿命特性。
按照一种实施方式，所述有机电致发光器件例如可以为绿色有机电致发光器件。如图1所示，有机电致发光器件可以包括依次层叠设置的阳极100、第一空穴传输层321、第二空穴传输层322、作为能量转化层的有机发光层330、电子传输层340和阴极200。
可选地，阳极100包括以下阳极材料，其优选地是有助于空穴注入至功能层中的具有大逸出功(功函数，work function)材料。阳极材料具体实例包括：金属如镍、铂、钒、铬、铜、锌和金或它们的合金；金属氧化物如氧化锌、氧化铟、氧化铟锡(ITO)和氧化铟锌(IZO)；组合的金属和氧化物如ZnO:Al或SnO 2:Sb；或导电聚合物如聚(3-甲基噻吩)、聚[3,4-(亚乙基-1,2-二氧基)噻吩](PEDT)、聚吡咯和聚苯胺，但不限于此。优选包括包含氧化铟锡(铟锡氧化物，indium tin oxide)(ITO)作为阳极的透明电极。
可选地，第一空穴传输层321和第二空穴传输层322分别包括一种或者多种空穴传输材料，空穴传输材料可以选自咔唑多聚体、咔唑连接三芳胺类化合物或者其他类型的化合物，本申请对此不做特殊的限定。例如，第一空穴传输层321可以由化合物NPB组成。在本申请一种实施方式中，第一空穴传输层由HT-01组成，第二空穴传输层322由HT-02组成。
可选地，有机发光层330可以由单一发光材料组成，也可以包括主体材料和客体材料。有机发光层的主体材料和/或客体材料可以含有本申请的有机化合物。
可选地，有机发光层330可以由单一发光材料组成，也可以包括主体材料和客体材料。有机发光层的主体材料可以含有本申请的有机化合物。进一步可选地，有机发光层330由主体材料和客体材料组成，注入有机发光层330的空穴和注入有机发光层330的电子可以在有机发光层330复 合而形成激子，激子将能量传递给主体材料，主体材料将能量传递给客体材料，进而使得客体材料能够发光。
有机发光层330的客体材料可以为具有缩合芳基环的化合物或其衍生物、具有杂芳基环的化合物或其衍生物、芳香族胺衍生物或者其他材料，本申请对此不做特殊的限制。
按照一种具体的实施方式，所述有机电致发光器件为绿光器件，其中的有机发光层包括主体材料和客体材料，其中所述主体材料为双主体发光材料，即，包括p-type型主体材料和n-type型主体材料，本申请的有机化合物既可作为p type型主体材料，也可以作为n type型主体材料。
在本申请的一种实施方式中，有机发光层的主体材料含有本申请的有机化合物。
电子传输层340可以为单层结构，也可以为多层结构，其可以包括一种或者多种电子传输材料，电子传输材料可以选自但不限于，苯并咪唑衍生物、噁二唑衍生物、喹喔啉衍生物或者其他电子传输材料。在本申请的一种实施方式中，电子传输层340可以由ET-01和LiQ组成。
本申请中，阴极200可以包括阴极材料，其是有助于电子注入至功能层中的具有小逸出功的材料。阴极材料的具体实例包括但不限于，金属如镁、钙、钠、钾、钛、铟、钇、锂、钆、铝、银、锡和铅或它们的合金；或多层材料如LiF/Al、Liq/Al、LiO 2/Al、LiF/Ca、LiF/Al和BaF 2/Ca。优选包括包含镁和银的金属电极作为阴极。
可选地，如图1所示，在阳极100和第一空穴传输层321之间还可以设置有空穴注入层310，以增强向第一空穴传输层321注入空穴的能力。空穴注入层310可以选用联苯胺衍生物、星爆状芳基胺类化合物、酞菁衍生物或者其他材料，本申请对此不做特殊的限制。例如，空穴注入层310可以由F4-TCNQ组成。
可选地，如图1所示，在阴极200和电子传输层340之间还可以设置有电子注入层350，以增强向电子传输层340注入电子的能力。电子注入层350可以包括有碱金属硫化物、碱金属卤化物等无机材料，或者可以包括碱金属与有机物的络合物。例如，电子注入层350可以包括LiQ。
本申请中，HT-01、HT-02和ET-01等化合物的具体结构如下文的实施例所示，在此不再赘述。
本申请第三方面提供一种电子装置包含本申请第二方面所述的有机电致发光器件。
按照一种实施方式，如图2所示，所述电子装置为电子装置400，该电子装置400包括上述有机电致发光器件。电子装置400例如可以为显示装置、照明装置、光通讯装置或者其他类型的电子装置，例如可以包括但不限于电脑屏幕、手机屏幕、电视机、电子纸、应急照明灯、光模块等。
下面所描述的实施例，除非其他方面表明所有的温度定为摄氏度。试剂购买于商品供应商如Aldrich Chemical Company,Arco Chemical Company and Alfa ChemicalCompany，使用时都没有经过进一步纯化，除非其他方面表明。一般的试剂从汕头西陇化工厂、广东光华化学试剂厂、广州化学试剂厂、天津好寓宇化学品有限公司、天津市福晨化学试剂厂、武汉鑫华远科技发展有限公司、青岛腾龙化学试剂有限公司和青岛海洋化工厂购买得到。
无水四氢呋喃、二氧六环、甲苯、乙醚是经过金属钠回流干燥得到。无水二氯甲烷和氯仿是经过氢化钙回流干燥得到。乙酸乙酯、石油醚、正己烷、N,N-二甲基乙酰胺和N,N-二甲基甲酰胺是经无水硫酸钠事先干燥使用。
以下反应一般是在氮气或氩气正压下或在无水溶剂上套一干燥管(除非其他方面表明)，反应瓶都塞上合适的橡皮塞，底物通过注射器打入。玻璃器皿都是干燥过的。
色谱柱是使用硅胶柱。硅胶(300-400目)购于青岛海洋化工厂。
低分辨率质谱(MS)数据的测定条件是：Agilent 6120四级杆HPLC-M(柱子型号：Zorbax SB-C18，2.1×30mm，3.5微米，6min，流速为0.6mL/min。流动相：5％-95％(含0.1％甲酸的CH 3CN) 在(含0.1％甲酸的H 2O)中的比例，采用电喷雾电离(ESI)，在210nm/254nm下，用UV检测。
纯的化合物的使用Agilent 1260pre-HPLC或Calesep pump 250pre-HPLC(柱子型号：NOVASEP 50/80mm DAC)，在210nm/254nm用UV检测。
中间体IM-a1的合成：
Figure PCTCN2021111341-appb-000048
将苯硼酸(20.0g；164.0mmol)，1,3-二溴-5-碘苯(65.3g；180.4mmol)，四(三苯基膦)钯(3.8g；3.3mmol)，四丁基溴化铵(10.6g；32.8mmol)，碳酸钾(49.9g；360.9mmol)，甲苯(320mL)，乙醇(80mL)和去离子水(80mL)加入氮气保护下的圆底烧瓶中，搅拌条件下升温至55-60℃，保持8h；而后将反应混合物降至室温，加入去离子水，搅拌10分钟，分离有机相，加入无水硫酸镁干燥后，减压除去溶剂；将所得粗产品使用正庚烷作为流动相进行硅胶柱色谱提纯，得到白色晶体中间体化合物IM-a1(31.1g；61％)。
参照中间体IM-a1的方法，以下表1中反应物A替代苯硼酸，以反应物B替代1,3-二溴-5-碘苯，合成下表1所示的中间体：
表1
Figure PCTCN2021111341-appb-000049
Figure PCTCN2021111341-appb-000050
中间体IM-b3的合成：
Figure PCTCN2021111341-appb-000051
将2-联苯硼酸(30.0g；150.5mmol)，三聚氯氰(55.9g；303.0mmol)，四(三苯基膦)钯(3.5g；3.0mmol)，四丁基溴化铵(9.8g；30.3mmol)，碳酸钾(46.1g；333.3mmol)，甲苯(240mL)和去离子水(60mL)加入氮气保护下的圆底烧瓶中，搅拌条件下升温至60-65℃，保持6h；而后将反应混合物降至室温，加入去离子水，搅拌后分离有机相，加入无水硫酸镁干燥后，减压除去溶剂；将所得粗产品使用二氯甲烷/正庚烷作为流动相进行硅胶柱色谱提纯，得到白色晶体中间体化合物IM-b3(19.0g；42％)。
参照中间体IM-b3的方法，以下表2中反应物C替代2-联苯硼酸，合成下表2所示的中间体：
表2
Figure PCTCN2021111341-appb-000052
Figure PCTCN2021111341-appb-000053
中间体IM-d1的合成：
Figure PCTCN2021111341-appb-000054
将苯硼酸(35.0g；287.0mmol)，3-氯-4-氟溴苯(60.1g；287.0mmol)，四(三苯基膦)钯(6.6g；5.7mmol)，四丁基溴化铵(18.5g；57.4mmol)，碳酸钾(87.3g；637.5mmol)，甲苯(280mL)，乙醇(70mL)和去离子水(70mL)加入氮气保护下的圆底烧瓶中，搅拌条件下升温至75-80℃，保持12h；而后将反应混合物降至室温，加入去离子水，搅拌15分钟，分离有机相，加入无水硫酸镁干燥后，减压除去溶剂；将所得粗产品使用正庚烷作为流动相进行硅胶柱色谱提纯，得到淡黄色固体中间体化合物IM-d1(37.7g；65％)。
参照中间体IM-d1的方法，以下表3中反应物D替代苯硼酸，以反应物E替代3-氯-4-氟溴苯，合成下表3所示的中间体：
表3
Figure PCTCN2021111341-appb-000055
Figure PCTCN2021111341-appb-000056
中间体IM-d1p的合成：
Figure PCTCN2021111341-appb-000057
将中间体IM-d1(37.0g；179.1mmol)，联硼酸频哪醇酯(68.2g；253.9mmol)，三(二亚苄基丙酮)二钯(1.6g；1.8mmol)，2-二环己基磷-2’,4’,6’-三异丙基联苯(1.7g；3.6mmol)，醋酸钾(35.1g；358.1mmol)和1,4-二氧六环(400mL)加入圆底烧瓶中，氮气保护条件下于95-100℃回流搅拌12小时，降至室温，向反应液中加入二氯甲烷和水，分液，有机相使用水洗后用无水硫酸镁干燥，减压条件下除去溶剂得到粗品；粗品使用二氯甲烷/正庚烷体系进行硅胶柱色谱提纯，得到白色固体中间体IM-d1p(41.0g；77％)。
参照中间体IM-d1p的方法，以下表4中反应物F替代中间体IM-d1，合成下表4所示的中间体：
表4
Figure PCTCN2021111341-appb-000058
Figure PCTCN2021111341-appb-000059
中间体IM-c1d1的合成：
Figure PCTCN2021111341-appb-000060
将中间体IM-c1(35.7g；134.2mmol)、中间体IM-d1p(40.0g；134.2mmol)、四(三苯基膦)钯(3.1g；2.7mmol)、四丁基溴化铵、(8.6g；26.8mmol)、碳酸钾(37.1g；268.5mmol)，甲苯(300mL)、乙醇(80mL)和去离子水(80mL)加入氮气保护下的圆底烧瓶中，搅拌条件下升温至75-80℃，保持14小时；而后将反应混合物降至室温，加入去离子水，搅拌分离有机相，加入无水硫酸镁干燥后，减压除去溶剂；将所得粗产品使用二氯甲烷/正庚烷作为流动相进行硅胶柱色谱提纯，得到白色固体中间体IM-c1d1(30.9g；64％)。
参照中间体IM-c1d1的方法，以下表5中反应物G替代中间体IM-c1，以反应物H替代中间体IM-d1p，合成下表5所示的中间体：
表5
Figure PCTCN2021111341-appb-000061
Figure PCTCN2021111341-appb-000062
中间体IM-c1d1p的合成：
Figure PCTCN2021111341-appb-000063
将中间体IM-c1d1(30.0g；83.6mmol)、联硼酸频哪醇酯(31.8g；125.4mmol)、三(二亚苄基丙酮)二钯(0.8g；0.8mmol)、2-二环己基磷-2’,4’,6’-三异丙基联苯(0.8g；1.7mmol)、醋酸钾(16.4g；167.2mmol)和1，4-二氧六环(300mL)加入圆底烧瓶中，氮气保护条件下于95-100℃回流搅拌10小时，降至室温，向反应液中加入二氯甲烷和水，分液，有机相使用水洗后用无水硫酸镁干燥，减压条件下除去溶剂得到粗品；粗品使用乙酸乙酯/正庚烷体系进行硅胶柱色谱提纯，得到白色固体中间体IM-c1d1p(22.2g；59％)。
参照中间体IM-c1d1p的方法，以下表6中反应物I替代中间体IM-c1d1，合成下表6所示的 中间体：
表6
Figure PCTCN2021111341-appb-000064
Figure PCTCN2021111341-appb-000065
中间体IM-a1c1d1的合成：
Figure PCTCN2021111341-appb-000066
将中间体IM-a1(15.0g；48.1mmol)、中间体IM-c1d1p(19.5g；43.3mmol)、四(三苯基膦)钯(1.1g；1.0mmol)、四丁基溴化铵(3.1g；9.6mmol)、碳酸钾(13.3g；96.2mmol)、甲苯(120mL)，乙醇(30mL)和去离子水(30mL)加入氮气保护下的圆底烧瓶中，搅拌条件下升温至55-60℃，保持8h；而后将反应混合物降至室温，加入去离子水，搅拌15分钟，分离有机相，加入无水硫酸镁干燥后，减压除去溶剂；将所得粗产品使用二氯甲烷/正庚烷作为流动相进行硅胶柱色谱提纯，得到白色晶体中间体IM-a1c1d1(17.2g；72％)。
参照中间体IM-a1c1d1的方法，以下表7中反应物J替代中间体IM-a1，以反应物K替代中间体IM-c1d1p，合成下表7所示的中间体：
表7
Figure PCTCN2021111341-appb-000067
Figure PCTCN2021111341-appb-000068
中间体IM-b3c1d1的合成：
Figure PCTCN2021111341-appb-000069
将中间体IM-b3(10.0g；33.1mmol)、中间体IM-c1d1p(13.4g；29.8mmol)、四(三苯基膦)钯 (0.8g；0.7mmol)、四丁基溴化铵(2.1g；6.6mmol)、碳酸钾(9.1g；66.2mmol)、甲苯(80mL)和去离子水(40mL)加入氮气保护下的圆底烧瓶中，搅拌条件下升温至60-65℃，保持6小时；而后将反应混合物降至室温，加入去离子水，搅拌10分钟，分离有机相，加入无水硫酸镁干燥后，减压除去溶剂；将所得粗产品使用二氯甲烷/正庚烷作为流动相进行硅胶柱色谱提纯，得到白色固体中间体IM-b3c1d1(11.2g；61％)。
参照中间体IM-b3c1d1的方法，以下表8中反应物M替代中间体IM-b3，以反应物N替代中间体IM-c1d1p,合成下表8所示的中间体：
表8
Figure PCTCN2021111341-appb-000070
Figure PCTCN2021111341-appb-000071
中间体IM-a1c1d1p的合成：
Figure PCTCN2021111341-appb-000072
将中间体IM-a1c1d1(15.0g；27.0mmol)、吲哚并[2,3-a]咔唑(7.6g；29.7mmol)，三(二亚苄基丙酮)二钯(0.5g；0.5mmol)、叔丁醇钠(5.7g；59.4mmol)、三叔丁基膦(0.2g；1.1mmol)和二甲苯(200mL)加入氮气保护下的圆底烧瓶中，搅拌条件下升温至135-140℃，保持3h；而后将反应混合物降至室温，加入去离子水，搅拌10分钟，分离有机相，加入无水硫酸镁干燥后，减压除去溶剂；将所得粗产品使用二氯甲烷/正庚烷作为流动相进行硅胶柱色谱提纯，而后使用二氯甲烷/正庚烷对粗品进行重结晶提纯，得到白色固体中间体化合物IM-a1c1d1i(14.7g；74％)。
参照中间体IM-a1c1d1i的方法，以下表9中反应物O替代中间体IM-a1c1d1，合成下表9中中间体：
表9
Figure PCTCN2021111341-appb-000073
Figure PCTCN2021111341-appb-000074
中间体IM-b3c1d1的合成：
Figure PCTCN2021111341-appb-000075
向氮气保护下的圆底烧瓶中加入氢化钠(0.4g；16.9mmol)和二甲基甲酰胺(10mL)，降温至零下10℃至零下15℃，搅拌条件下滴加吲哚并[2,3-a]咔唑(3.9g；15.3mmol)的二甲基甲酰胺(10mL)溶液；零下10℃至零下15℃保温1小时，而后滴加中间体IM-b3c1d1(10.0g；16.9mmol)的二甲基甲酰胺(30mL)溶液，零下10℃至零下15℃保温1h，而后升温至45℃-50℃，搅拌8小时，降至室温，过滤，所得固体使用去离子水和乙醇淋洗，减压条件下干燥，所得粗品使用二氯甲烷作为溶剂进行重结晶提纯，得到白色固体中间体IM-b3c1d1i(9.5g；69％)。
参照中间体IM-b3c1d1i的方法，以下表10中反应物P替代中间体b3c1d1，合成下表10所示的中间体：
表10
Figure PCTCN2021111341-appb-000076
Figure PCTCN2021111341-appb-000077
Figure PCTCN2021111341-appb-000078
化合物A16的合成：
Figure PCTCN2021111341-appb-000079
将碳酸铯(44.5g；136.8mmol)和二甲基乙酰胺(200mL)加入圆底烧瓶中，于145-150℃搅拌条件下，缓慢滴加中间体IM-a1c1d1i(10g；13.7mmol)的二甲基乙酰胺(300mL)溶液，而后保温反应48h，降至室温，向反应液中加入甲苯而后使用大量去离子水洗，分离有机相并使用无水硫酸镁干燥，减压除去溶剂，所得粗品使用二氯甲烷/正庚烷作为洗脱液进行硅胶柱色谱提纯，而后使用甲苯/正庚烷作为溶剂进行重结晶提纯，得到白色固体化合物A16(3.8g；34％)。
参照化合物A16相同的方法，以下表11中反应物A替代中间体IM-a1c1d1i，合成下表11所示的中间体：
表11
Figure PCTCN2021111341-appb-000080
Figure PCTCN2021111341-appb-000081
Figure PCTCN2021111341-appb-000082
Figure PCTCN2021111341-appb-000083
部分化合物质谱数据如下表12所示。
表12
化合物A2 m/z＝559.2[M+H] + 化合物B74 m/z＝611.2[M+H] +
化合物A5 m/z＝635.2[M+H] + 化合物C3 m/z＝635.2[M+H] +
化合物A7 m/z＝609.2[M+H] + 化合物C11 m/z＝609.2[M+H] +
化合物A12 m/z＝649.2[M+H] + 化合物C24 m/z＝741.2[M+H] +
化合物A14 m/z＝675.3[M+H] + 化合物C31 m/z＝714.3[M+H] +
化合物A16 m/z＝711.3[M+H] + 化合物D2 m/z＝638.2[M+H] +
化合物A25 m/z＝714.3[M+H] + 化合物D8 m/z＝638.2[M+H] +
化合物B1 m/z＝562.2[M+H] + 化合物D25 m/z＝714.3[M+H] +
化合物B5 m/z＝638.2[M+H] + 化合物D37 m/z＝652.2[M+H] +
化合物B13 m/z＝714.3[M+H] + 化合物D51 m/z＝727.3[M+H] +
化合物B21 m/z＝790.3[M+H] + 化合物D56 m/z＝764.3[M+H] +
化合物B47 m/z＝668.2[M+H] + 化合物D63 m/z＝661.2[M+H] +
化合物B60 m/z＝688.2[M+H] +    
部分化合物核磁数据如下表13所示。
表13
Figure PCTCN2021111341-appb-000084
使用以下方法进行绿色有机电致发光器件的制作：
实施例1：绿色有机电致发光器件
通过以下过程制备阳极：将厚度为
Figure PCTCN2021111341-appb-000085
的ITO基板(康宁制造)切割成40mm×40mm×0.7mm的尺寸，采用光刻工序，将其制备成具有阴极、阳极以及绝缘层图案的实验基板，利用紫外臭氧以及O 2:N 2等离子进行表面处理，以增加阳极(实验基板)的功函数的和清除浮渣。
在实验基板(阳极)上真空蒸镀F4-TCNQ以形成厚度为的厚度为
Figure PCTCN2021111341-appb-000086
的空穴注入层(HIL)，并且在空穴注入层蒸镀HT-01，形成厚度为
Figure PCTCN2021111341-appb-000087
的第一空穴传输层。
在第一空穴传输层上真空蒸镀HT-02，形成厚度为
Figure PCTCN2021111341-appb-000088
的第二空穴传输层。
在第二空穴传输层上，将化合物A2：GH-n1：Ir(ppy) 3以50％：45％：5％的重量比进行共同蒸镀，形成厚度为
Figure PCTCN2021111341-appb-000089
的绿色有机发光层(EML)。
将ET-01和LiQ以1:1的重量比进行混合并蒸镀形成了
Figure PCTCN2021111341-appb-000090
厚的电子传输层(ETL)，将LiQ蒸镀在电子传输层上以形成厚度为
Figure PCTCN2021111341-appb-000091
的电子注入层(EIL)，然后将镁(Mg)和银(Ag)以1：9的蒸镀速率混合，真空蒸镀在电子注入层上，形成厚度为
Figure PCTCN2021111341-appb-000092
的阴极。
此外，在上述阴极上蒸镀厚度为
Figure PCTCN2021111341-appb-000093
的CP-1，形成有机覆盖层(CPL)，从而完成有机发光器件的制造，结构如图1所示。
实施例2-实施例11
除了在形成有机发光层时，以下表14中所示的化合物替代化合物A2以外，利用与实施例1相同的方法制作有机电致发光器件。
实施例12-实施例25
除了在形成有机发光层时，以GH-p1替代化合物A2，以及以下表14中所示的化合物替代GH-n1以外，利用与实施例1相同的方法制作有机电致发光器件。
比较例1
除了在形成有机发光层时，以GH-p1替代化合物A2以外，利用与实施例1相同的方法制作有机电致发光器件。
比较例2
除了在形成有机发光层时，以下表中所示的化合物I替代化合物A2以外，利用与实施例1相同的方法制作有机电致发光器件。
比较例3
除了在形成有机发光层时，以GH-p1替代化合物A2以及化合物II替代GH-n1以外，利用与实施例1相同的方法制作有机电致发光器件。
比较例4
除了在形成有机发光层时，以GH-p1替代化合物A2以及化合物III替代GH-n1以外，利用与实施例1相同的方法制作有机电致发光器件。
以上实施例和对比例使用的材料结构如下所示：
Figure PCTCN2021111341-appb-000094
对如上制得的有机电致发光器件，在20mA/cm 2的条件下分析了器件的性能，其结果示于下表14：
表14
Figure PCTCN2021111341-appb-000095
Figure PCTCN2021111341-appb-000096
Figure PCTCN2021111341-appb-000097
参考上表可知，实施例1-11将本申请化合物用作绿色发光层混合主体材料中的空穴型主体材料，与比较例1相比，器件发光效率与寿命得到了较为明显的提升；与比较例2相比，寿命得到了大幅度的提升。相比于比较例1和比较例2，实施例1-11用本申请化合物制备得有机电致发光器件，寿命至少提高了22.67％，发光效率Cd/A至少提高了10.2％。
实施例12-25将本申请化合物用作绿色发光层混合主体材料中的电子型主体材料，与比较例1相比，器件发光效率与寿命得到了较为明显的提升；与比较例3相比，在器件寿命相近的前提下，发光效率得到了较为明显的提升；究其原因，可能在于本申请化合物具有的刚性结构所引起的更高的载流子和能量传输效率；与比较例4相比，在器件发光效率类似的前提下，寿命得到了大幅度的提升。相比于比较例3和比较例4，实施例12-25用本申请化合物制备得到的有机电致发光器件，寿命至少提高了12.4％，发光效率Cd/A至少提高了10.5％，外量子效率EQE至少提高了9.9％。
因此，本申请的新型化合物用于制备绿色有机电致发光器件时，可以有效地改善有机电致发光器件的发光效率，并延长其寿命。
以上详细描述了本申请的优选实施方式，但是，本申请并不限于上述实施方式中的具体细节，在本申请的技术构思范围内，可以对本申请的技术方案进行多种简单变型，这些简单变型均属于本申请的保护范围。
另外需要说明的是，在上述具体实施方式中所描述的各个具体技术特征，在不矛盾的情况下，可以通过任何合适的方式进行组合。为了避免不必要的重复，本申请对各种可能的组合方式不再另行说明。
此外，本申请的各种不同的实施方式之间也可以进行任意组合，只要其不违背本申请的思想，其同样应当视为本申请所公开的内容。

Claims (12)

  1. 一种有机化合物，其特征在于，所述有机化合物的结构如式I所示：
    Figure PCTCN2021111341-appb-100001
    其中，环A选自式A所示的基团：
    Figure PCTCN2021111341-appb-100002
    Figure PCTCN2021111341-appb-100003
    表示与Ar 1、Ar 2键合；
    R 6、R 7、R 8和R 9分别独立地选自氢、氘、碳原子数为6-30的取代或未取代的芳基、碳原子数为6-30的取代或未取代的杂芳基；
    或者任选地，R 6、R 7、R 8、R 9中两个相邻基团相互连接形成碳原子数为6-14的芳环；
    Ar 1和Ar 2分别独立地选自碳原子数为6-20的未取代的亚芳基、碳原子数为3-20的未取代的亚杂芳基；
    R 1和R 2相同或不同，且各自独立地选自氢、氘、卤素基团、氰基、碳原子数为1-30的烷基、碳原子数为3-30的环烷基、碳原子数为1-30的烷氧基、碳原子数为3-12的三烷基硅基、碳原子数为18-24的三芳基硅基或式B所示的结构；
    Figure PCTCN2021111341-appb-100004
    L 1和L 2相同或不同，且分别独立地选自单键、碳原子数为6-30的取代或未取代的亚芳基、碳原子数为3-30的取代或未取代的亚杂芳基；
    Ar选自碳原子数为6-30的取代或未取代的芳基、碳原子数为3-30的取代或未取代的杂芳基；
    R 3、R 4和R 5相同或不同，且各自独立地选自氘、卤素基团、氰基、碳原子数为1-10的烷基、碳原子数为6-20的芳基、碳原子数为3-20的杂芳基；
    n 3表示R 3的个数，n 4表示R 4的个数，n 5表示R 5的个数；
    n 3选自：0、1、2、3或4；
    n 4选自：0、1或2；
    n 5选自：0、1、2、3或4；
    R 6、R 7、R 8、R 9、L 1、L 2和Ar中的取代基各自独立地选自氘，卤素基团，氰基，碳原子数为3-20的杂芳基，任选地被0、1、2、3、4或5个独立地选自氘、氟、氰基、甲基、叔丁基的取代基所 取代的碳原子数为6-20的芳基，碳原子数为3-12的三烷基硅基，碳原子数为18-24的三芳基硅基，碳原子数为1-10的烷基，碳原子数为1-10的卤代烷基，碳原子数为3-10的环烷基，碳原子数为2-10的杂环烷基。
  2. 根据权利要求1所述的有机化合物，其中，所述环A选自如下基团所组成的组：
    Figure PCTCN2021111341-appb-100005
  3. 根据权利要求1所述的有机化合物，其中，Ar 1和Ar 2分别独立地选自碳原子数为6-14的未取代的亚芳基、碳原子数为3-16的未取代的亚杂芳基。
  4. 根据权利要求1所述的有机化合物，其中，Ar 1和Ar 2分别独立地选自以下基团组成的组：
    Figure PCTCN2021111341-appb-100006
  5. 根据权利要求1所述的有机化合物，其中，L 1和L 2分别独立地选自单键、碳原子数为6-12的取代或未取代的亚芳基、碳原子数为12-18的取代或未取代的亚杂芳基；
    优选地，所述L 1和L 2中的取代基分别独立地选自氘、氟、氰基、甲基、乙基、正丙基、异丙基、叔丁基、苯基、萘基。
  6. 根据权利要求1所述的有机化合物，其中，L 1和L 2分别独立地选自单键、取代或未取代的基团T 1，未取代的基团T 1选自如下基团所组成的组：
    Figure PCTCN2021111341-appb-100007
    其中，取代的基团T 1中的取代基各自独立地选自氘、氟、氰基、甲基、乙基、正丙基、异丙基、叔丁基、苯基、萘基。
  7. 根据权利要求1所述的有机化合物，其中，Ar选自碳原子数为6-25的取代或未取代的芳基、碳原子数为5-20的取代或未取代的杂芳基；
    优选地，所述Ar中的取代基选自氘、氟、氰基、碳原子数为1-5的烷基、碳原子数为6-20的芳基、碳原子数为5-18的杂芳基。
  8. 根据权利要求1所述的有机化合物，其中，Ar选自取代或未取代的基团T 2，未取代的基团T 2选自如下基团所组成的组：
    Figure PCTCN2021111341-appb-100008
    取代的基团T 2具有一个或两个以上取代基，取代的基团T 2中的取代基各自独立地选自氘、氟、氰基、甲基、乙基、正丙基、异丙基、叔丁基、苯基、萘基、联苯基、菲基、三联苯基。
  9. 根据权利要求1所述的有机化合物，其中，
    Figure PCTCN2021111341-appb-100009
    分别独立地选自取代或未取代的基团G，其中未取代的基团G选自如下基团组成的组：
    Figure PCTCN2021111341-appb-100010
    Figure PCTCN2021111341-appb-100011
    Figure PCTCN2021111341-appb-100012
    其中，
    Figure PCTCN2021111341-appb-100013
    表示化学键；取代的基团G上具有一个或多个的取代基，所述取代基各自独立地选自：氘、氰基、氟、甲基、乙基、正丙基、异丙基、叔丁基、苯基、萘基、联苯基、菲基、二苯并呋喃基、二苯并噻吩基、二甲基芴基、苯并噁唑基、N-苯基咔唑基、咔唑基；当基团G中的取代基个数大于1时，各取代基相同或不同。
  10. 根据权利要求1所述的有机化合物，其中，所述有机化合物选自如下化合物组成的组：
    Figure PCTCN2021111341-appb-100014
    Figure PCTCN2021111341-appb-100015
    Figure PCTCN2021111341-appb-100016
    Figure PCTCN2021111341-appb-100017
    Figure PCTCN2021111341-appb-100018
    Figure PCTCN2021111341-appb-100019
    Figure PCTCN2021111341-appb-100020
    Figure PCTCN2021111341-appb-100021
    Figure PCTCN2021111341-appb-100022
  11. 一种有机电致发光器件，其特征在于，包括相对设置的阳极和阴极，以及设于所述阳极和所述阴极之间的功能层；
    所述功能层包含权利要求1-10中任意一项所述的有机化合物；
    优选地，所述功能层包括有机发光层，所述有机发光层包含所述有机化合物；
    更优选地，所述有机发光层包含主体材料，所述主体材料含有所述的有机化合物。
  12. 一种电子装置，其特征在于，包含权利要求11所述的有机电致发光器件。
PCT/CN2021/111341 2020-11-19 2021-08-06 有机化合物以及使用其的有机电致发光器件和电子装置 WO2022105313A1 (zh)

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