WO2022183798A1 - 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 - Google Patents

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 Download PDF

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WO2022183798A1
WO2022183798A1 PCT/CN2021/135441 CN2021135441W WO2022183798A1 WO 2022183798 A1 WO2022183798 A1 WO 2022183798A1 CN 2021135441 W CN2021135441 W CN 2021135441W WO 2022183798 A1 WO2022183798 A1 WO 2022183798A1
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carbon atoms
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organic compound
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刘文强
李应文
韩超
冯震
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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.
  • patent CN107459466A discloses light-emitting layer materials that can be prepared in organic electroluminescent devices. However, it is still necessary to continue to develop new materials to further improve the performance of electronic components.
  • the purpose of the present application is to provide an organic compound and an organic electroluminescent device and electronic device using the same.
  • the organic compound of the present application is used for the hole adjustment layer material of the organic electroluminescent device, the luminous efficiency and service life.
  • a first aspect of the present application provides an organic compound, the structure of which is shown in formula 1:
  • ring A is adamantyl or norbornyl
  • L 1 , L 2 and L 3 are the same or different, and are each independently selected from a single bond, a substituted or unsubstituted arylene group having 6-30 carbon atoms, and a substituted or unsubstituted group having 3-30 carbon atoms the heteroarylene;
  • R 1 , R 2 , R 3 , R 4 and R 5 are the same as or different from each other, and are each independently selected from deuterium, halogen group, cyano group, alkyl group having 1 to 20 carbon atoms, and alkyl group having 3 carbon atoms. -20 cycloalkyl, aryl with 6-30 carbon atoms, heteroaryl with 3-30 carbon atoms;
  • R 6 is selected from deuterium, halogen group, cyano group, alkyl group with 1-20 carbon atoms, cycloalkyl group with 3-20 carbon atoms, heteroaryl group with 3-30 carbon atoms;
  • n 1 , n 2 , n 4 and n 6 are the same or different from each other, and are each independently selected from 0, 1, 2, 3 or 4; n 3 is selected from 0, 1, 2 or 3;
  • n 5 is selected from 0, 1, 2, 3, 4 or 5;
  • Ar 1 is selected from substituted or unsubstituted aryl groups with 6-30 carbon atoms, and substituted or unsubstituted heteroaryl groups with 3-30 carbon atoms;
  • the substituents in the L 1 , L 2 , L 3 and Ar 1 are independently selected from deuterium, halogen group, cyano group, heteroaryl group with 3-20 carbon atoms, and 6-20 carbon atoms aryl, trialkylsilyl with 3-12 carbon atoms, triarylsilyl with 18-24 carbon atoms, alkyl group with 1-10 carbon atoms, 1-10 carbon atoms haloalkyl, alkenyl with 2-6 carbon atoms, alkynyl with 2-6 carbon atoms, cycloalkyl with 3-10 carbon atoms, heterocycloalkyl with 2-10 carbon atoms, Cycloalkenyl with 5-10 carbon atoms, heterocycloalkenyl with 4-10 carbon atoms, alkoxy with 1-10 carbon atoms, alkylthio group with 1-10 carbon atoms, carbon An aryloxy group having 6-18 atoms, an arylthio group having 6-18 carbon atoms, and a pho
  • a second aspect of the present application provides an organic electroluminescence 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 organic compound provided in the first aspect of the present application.
  • the functional layer includes a hole adjustment layer, and the hole adjustment layer contains the organic compound.
  • a third aspect of the present application provides an electronic device, including the organic electroluminescence device provided in the second aspect of the present application.
  • an aryl group in the triarylamine group is fixed as a 9-fluorenyl group connected by a phenylene group, and combined with a fluorene spiro ring structure, wherein the 9-fluorenyl group connected by a phenylene group is -
  • the fluorenyl group avoids the disadvantage of poor thermal stability of the 9,9-disubstituted fluorenyl group, and at the same time makes full use of the excellent hole transport properties of fluorene, combining N and phenyl
  • the adjustment of the connection position makes these materials have an excellent spatial configuration, a more easily regulated HOMO energy level, a better hole transport ability than the disubstituted fluorenyl group connected at the 1-4 position, and is not easy to crystallize.
  • the luminous efficiency of the device can be greatly improved.
  • such materials can maintain a relatively long life while maintaining high efficiency.
  • the introduction of an adamantyl group or a norbornyl group on the fluorene ring can provide good mobility.
  • the organic compound of the present application When the organic compound of the present application is used as the material for the hole adjustment layer of the green light device of the organic electroluminescence device, the luminous efficiency and lifespan of the device will be effectively improved.
  • FIG. 1 is a schematic structural diagram of a specific embodiment of the organic electroluminescent device of the present application.
  • FIG. 2 is a schematic structural diagram of an embodiment of an electronic device including the organic electroluminescent device of the present application.
  • a first aspect of the present application provides an organic compound, and the structure of the organic compound is shown in Formula 1:
  • ring A is adamantyl or norbornyl
  • L 1 , L 2 and L 3 are the same or different, and are each independently selected from a single bond, a substituted or unsubstituted arylene group having 6-30 carbon atoms, and a substituted or unsubstituted group having 3-30 carbon atoms the heteroarylene;
  • R 1 , R 2 , R 3 , R 4 and R 5 are the same as or different from each other, and are each independently selected from deuterium, halogen group, cyano group, alkyl group having 1 to 20 carbon atoms, and alkyl group having 3 carbon atoms. -20 cycloalkyl, aryl with 6-30 carbon atoms, heteroaryl with 3-30 carbon atoms;
  • R 6 is selected from deuterium, halogen group, cyano group, alkyl group with 1-20 carbon atoms, cycloalkyl group with 3-20 carbon atoms, heteroaryl group with 3-30 carbon atoms;
  • n 1 , n 2 , n 4 and n 6 are the same or different from each other, and are each independently selected from 0, 1, 2, 3 or 4; n 3 is selected from 0, 1, 2 or 3;
  • n 5 is selected from 0, 1, 2, 3, 4 or 5;
  • Ar 1 is selected from substituted or unsubstituted aryl groups with 6-30 carbon atoms, and substituted or unsubstituted heteroaryl groups with 3-30 carbon atoms;
  • the substituents in the L 1 , L 2 , L 3 and Ar 1 are independently selected from deuterium, halogen group, cyano group, heteroaryl group with 3-20 carbon atoms, and 6-20 carbon atoms aryl, trialkylsilyl with 3-12 carbon atoms, triarylsilyl with 18-24 carbon atoms, alkyl group with 1-10 carbon atoms, 1-10 carbon atoms haloalkyl, alkenyl with 2-6 carbon atoms, alkynyl with 2-6 carbon atoms, cycloalkyl with 3-10 carbon atoms, heterocycloalkyl with 2-10 carbon atoms, Cycloalkenyl with 5-10 carbon atoms, heterocycloalkenyl with 4-10 carbon atoms, alkoxy with 1-10 carbon atoms, alkylthio group with 1-10 carbon atoms, carbon An aryloxy group having 6-18 atoms, an arylthio group having 6-18 carbon atoms, and a pho
  • n 1 , n 2 , n 3 , n 4 , n 5 and n 6 are all zero.
  • each independently is can be interchanged, and should be understood in a broad sense, which can be either It means that 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, and each R" is independently selected from hydrogen, deuterium, fluorine, chlorine", and its meaning is:
  • 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 selected from, for example, deuterium, halogen group, cyano group, heteroaryl with 3-20 carbon atoms, aryl with 6-20 carbon atoms, and 3-12 carbon atoms in the group.
  • trialkylsilyl group triarylsilyl group with 18-24 carbon atoms, alkyl group with 1-10 carbon atoms, halogenated alkyl group with 1-10 carbon atoms, 2-6 carbon atoms Alkenyl, alkynyl with 2-6 carbon atoms, cycloalkyl with 3-10 carbon atoms, heterocycloalkyl with 2-10 carbon atoms, cycloalkenyl with 5-10 carbon atoms , Heterocycloalkenyl with 4-10 carbon atoms, alkoxy with 1-10 carbon atoms, alkylthio with 1-10 carbon atoms, aryloxy with 6-18 carbon atoms, An arylthio group having 6 to 18 carbon atoms, and a phosphineoxy group having 6 to 18 carbon atoms.
  • the number of carbon atoms of a substituted or unsubstituted functional group refers to the number of all carbon atoms in the functional group and the substituents on it.
  • Ar 1 is selected from a substituted aryl group with a carbon number of 30, then all the carbon atoms of the aryl group and the substituents thereon are 30; for another example, if L 1 is selected from a carbon number of carbon atoms If the substituted arylene group is 15, the number of all carbon atoms in the arylene group and the substituents thereon is 15.
  • the number of carbon atoms refers to all carbon atoms.
  • L 1 is a substituted arylene group with 12 carbon atoms, then all the carbon atoms in the arylene group and the substituents therein are 12.
  • Ar 1 is Then the number of carbon atoms is 7; L 1 is Its carbon number is 12.
  • 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 (eg, phenyl) or a polycyclic aryl group, in other words, the aryl group can be a monocyclic aryl group, a fused-ring aryl group, two aryl groups that are conjugated through a carbon-carbon bond Or more monocyclic aryl groups, monocyclic aryl groups and condensed aryl groups conjugated through carbon-carbon bonds, two or more condensed aryl groups conjugated through carbon-carbon bonds. 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.
  • phenyl and the like are aryl groups.
  • aryl groups may include, but are not limited to, phenyl, naphthyl, fluorenyl, 9,9-dimethylfluorenyl, spirobifluorenyl, indenyl, anthracenyl, phenanthryl, biphenyl, terphenyl base, tetraphenyl, pentaphenyl, benzo[9,10]phenanthryl, pyrenyl, fluoranthene, benzofluoranthyl, base, perylene base, etc.
  • An "aryl group” as used herein may have one or more linkages to the rest of the molecule.
  • the substituted aryl group may be one or two or more hydrogen atoms in the aryl group replaced by a group such as a deuterium atom, a halogen group, a cyano group (-CN), an aryl group, a heteroaryl group, a trialkylsilyl group , alkyl, cycloalkyl, alkoxy, alkylthio and other groups are substituted.
  • a group such as a deuterium atom, a halogen group, a cyano group (-CN), an aryl group, a heteroaryl group, a trialkylsilyl group , alkyl, cycloalkyl, alkoxy, alkylthio and other groups are substituted.
  • the number of carbon atoms of a substituted aryl group refers to the total number of carbon atoms of the aryl group and the substituents on the aryl group, for example, a substituted aryl group with a carbon number of 20 refers to the aryl group and the substituted aryl group.
  • the total number of carbon atoms in the base is 20.
  • the number of carbon atoms of the aryl group having 6 to 30 carbon atoms is, for example, 6 (phenyl), 10 (naphthyl), 12 (for example, biphenyl), 14, 15, 16, 18, 20, 24, 25, etc.
  • aryl groups as substituents include, but are not limited to, phenyl, naphthyl, biphenyl, terphenyl, phenanthrenyl, anthracenyl, fluorenyl and the like.
  • the arylene group referred to refers to a group formed by the further loss of a hydrogen atom from an aryl group.
  • the arylene group includes a group formed by the further loss of one or two or more hydrogen atoms from the aryl group, eg, a arylene group.
  • the definition of aryl can apply to arylene and arylene.
  • heteroaryl refers to a monovalent aromatic ring or its derivatives containing 1, 2, 3, 4, 5, 6 or 7 heteroatoms in the ring, wherein the heteroatoms may be B, O, At least one of 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, phenothiazinyl, phenoxazinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl , pyrazinopyrazinyl, isoquinolinyl, indolyl, carbazolyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothienyl, diphenyl thienyl,
  • 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 It is understood that the "heteroaryl” may have one bond, two bonds, or more bonds to the rest of the molecule.
  • the number of carbon atoms of the heteroaryl group having 3 to 30 carbon atoms is, for example, 3, 4, 5, 8, 9, 12, 15, 18, 24 and the like.
  • the number of carbon atoms in the arylene group having 6 to 18 carbon atoms is, for example, 6, 12, 18, and the like.
  • heteroaryl groups as substituents include, but are not limited to: phenanthroline, furyl, thienyl, pyridyl, dibenzofuranyl, dibenzothienyl, carbazolyl, N - Phenylcarbazolyl, etc.
  • alkyl refers to a saturated straight or branched chain monovalent hydrocarbon radical, wherein the alkyl group may be optionally substituted with one or more substituents described herein.
  • the alkyl group having 1-20 carbon atoms may be a straight-chain alkyl group having 1-20 carbon atoms, or a branched-chain alkyl group having 3-20 carbon atoms.
  • the number of carbon atoms may be, for example, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, and 20.
  • the alkyl group in the present application contains 1-10 carbon atoms; in other embodiments, the alkyl group in the present application contains 1-6 carbon atoms; in still other embodiments, the present application In other embodiments, the alkyl group in this application contains 1-3 carbon atoms.
  • alkyl groups include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n-pentyl, isopentyl, neopentyl, tert-amyl, hexyl, n-hexyl, 2-methylpentyl, 2-ethylbutyl, heptyl, n- Heptyl, octyl, n-octyl, t-octyl, n-nonyl, decyl, etc., but not limited thereto.
  • alkyl groups having 1 to 4 carbon atoms in the present application include, but are not limited to: methyl (Me, -CH 3 ), ethyl (Et, -CH 2 CH 3 ), n-propyl (n-Pr, -CH 2 CH 2 CH 3 ), isopropyl (i-Pr, -CH(CH 3 ) 2 ), n-butyl (n-Bu, -CH 2 CH 2 CH 2 CH), tert-butyl (t- Bu,-C(CH 3 ) 3 ) and the like.
  • the halogen group may be fluorine, chlorine, bromine, iodine.
  • haloalkyl group having 1 to 10 carbon atoms include, but are not limited to, trifluoromethyl.
  • connection key is used for express.
  • a non-positioned connecting 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 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 dibenzofuranyl group represented by the formula (X') is connected to other positions of the molecule through a non-positional linkage extending from the middle of one side of the benzene ring,
  • the meaning represented by it includes any possible connection modes shown by formula (X'-1) to formula (X'-4).
  • Ar 1 is selected from a substituted or unsubstituted aryl group with 6-20 carbon atoms and a substituted or unsubstituted heteroaryl group with 12-20 carbon atoms.
  • the substituent in Ar 1 is selected from deuterium, halogen group, cyano group, alkyl group with 1-5 carbon atoms, aryl group with 6-12 carbon atoms, aryl group with 12-14 carbon atoms Heteroaryl, haloalkyl with 1-5 carbon atoms.
  • substituents in Ar 1 include but are not limited to: deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, phenyl, naphthyl, biphenyl , phenanthryl, dimethylfluorenyl, dibenzofuranyl, dibenzothienyl, carbazolyl, trifluoromethyl, etc.
  • Ar 1 is selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted Substituted dimethylfluorenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted 9,9-dimethyl-9H-9-silylfluorenyl, substituted or unsubstituted dibenzothienyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted carbazolyl.
  • Ar 1 is selected from a substituted or unsubstituted group W, and the unsubstituted group W is selected from the group consisting of the following groups:
  • substituents when the group W is substituted by one or more substituents, the substituents are the same or different, and each is independently selected from: deuterium, fluorine, cyano, methyl, ethyl, n-propyl, Isopropyl, tert-butyl, phenyl, naphthyl, biphenyl, trifluoromethyl.
  • Ar 1 is selected from the group consisting of:
  • the L 1 , L 2 and L 3 are the same or different, and each is independently selected from a single bond, a substituted or unsubstituted arylene group with 6-20 carbon atoms, A substituted or unsubstituted heteroarylene group having 12-20 carbon atoms.
  • the substituents in the L 1 , L 2 and L 3 are independently selected from deuterium, halogen group, cyano group, alkyl group with 1-5 carbon atoms, and alkyl group with 6-12 carbon atoms aryl group.
  • substituents in L 1 , L 2 and L 3 include but are not limited to: deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, benzene base, naphthyl, biphenyl.
  • the L 1 , L 2 and L 3 are the same or different, and each is independently selected from a single bond, a substituted or unsubstituted phenylene group, and a substituted or unsubstituted naphthylene group , substituted or unsubstituted phenanthrene, substituted or unsubstituted biphenylene, substituted or unsubstituted fluorenylene, substituted or unsubstituted carbazolylylene, substituted or unsubstituted dibenzofuranyl , substituted or unsubstituted dibenzothienylene, substituted or unsubstituted N-phenylcarbazolidene.
  • the L 1 , L 2 and L 3 are each independently selected from a single bond, a substituted or unsubstituted group V; the unsubstituted group V is selected from the following groups The group consists of:
  • each of the substituents is the same or different, and each is independently selected from: deuterium, fluorine, cyano, methyl, ethyl, n-propyl, Isopropyl, tert-butyl, phenyl, naphthyl.
  • L 3 is selected from a single bond or phenylene.
  • L is selected from the group consisting of a single bond or the following groups:
  • the R 1 , R 2 , R 3 , R 4 and R 5 are the same or different from each other, and are each independently selected from deuterium, halogen group, cyano group, and the number of carbon atoms is 1-10 alkyl group, 3-15 carbon atom cycloalkyl group, 6-25 carbon atom aryl group, 3-25 carbon atom heteroaryl group;
  • said R 1 , R 2 , R 3 , R 4 and R 5 are the same or different from each other, and are each independently selected from deuterium, halogen group, cyano, methyl, ethyl, n-propyl, isopropyl Propyl, cyclopropyl, cyclobutyl, cyclopentyl, phenyl, naphthyl, phenanthryl, anthracenyl, carbazolyl, dibenzothienyl, dibenzofuranyl.
  • R 6 is selected from deuterium, halogen group, cyano group, alkyl group with 1-10 carbon atoms, cycloalkyl group with 3-15 carbon atoms, heteroaryl group with 3-25 carbon atoms;
  • said R 6 is selected from deuterium, halogen group, cyano, methyl, ethyl, n-propyl, isopropyl, cyclopropyl, cyclobutyl, cyclopentyl, carbazolyl, diphenyl And thienyl, dibenzofuranyl.
  • the adamantyl group refers to an unsubstituted adamantyl group
  • the norbornyl group refers to an unsubstituted norbornyl group
  • the ring A is selected from the following groups:
  • the organic compound is selected from the group consisting of the following organic compounds:
  • 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. of organic compounds.
  • the organic electroluminescent device may include an anode 100 and a cathode 200 disposed oppositely, and a functional layer 300 disposed between the anode 100 and the cathode 200; the functional layer 300 contains the organic compounds.
  • the functional layer 300 includes a hole adjustment layer 322, and the hole adjustment layer 322 includes the organic compound provided in the present application.
  • the organic electroluminescent device may be, for example, a green organic electroluminescent device.
  • the organic electroluminescent device may include an anode 100, a hole transport layer 321, a hole adjustment layer 322, an organic light emitting layer 330 serving as an energy conversion layer, and an electron transport layer, which are stacked in sequence. 350 and cathode 200.
  • the anode 100 contains 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.
  • the anode 100 includes a transparent electrode including indium tin oxide (ITO) as an anode.
  • a hole injection layer 310 may also be disposed between the anode 100 and the hole transport layer 321 to enhance the capability of injecting holes into the hole transport layer 321 .
  • the hole injection layer 310 can be selected from benzidine derivatives, starburst arylamine compounds, phthalocyanine derivatives or other materials, which are not specifically limited in this application.
  • the hole injection layer 310 may be composed of HAT-CN.
  • a hole transport layer 321 may also be disposed between the hole injection layer 310 and the hole adjustment layer 322, and the hole transport layer 321 may further include one or more hole transport materials.
  • the material can be selected from carbazole polymers, carbazole-linked triarylamine compounds or other types of compounds, which are not specifically limited in this application.
  • the hole transport layer 321 contains the compound NPB, and the hole transport layer 321 is adjacent to the hole injection layer 310 .
  • the functional layer 300 includes a hole adjustment layer 322, and the hole adjustment layer 322 includes the organic compound provided in this application.
  • the hole adjustment layer 322 may be composed of the organic compound provided in the present application, or may be composed of the organic compound provided in the present application and other materials.
  • 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 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 organic light-emitting layer 330.
  • Host material the host material transfers energy to the guest material, thereby enabling the guest material to emit light.
  • the host material of the organic light-emitting layer 330 may be metal chelate compounds, bis-styryl derivatives, aromatic amine derivatives, dibenzofuran derivatives or other types of materials, which are not specifically limited in this application.
  • the dopant 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. limits.
  • the organic light emitting layer 330 may contain CBP and Ir(ppy) 3 .
  • the cathode 200 contains a cathode material, which is preferably 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 silver and magnesium is preferably included as the cathode.
  • the electron transport layer 350 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 350 may be composed of TPyQB and LiQ.
  • an electron injection layer 360 may also be disposed between the cathode 200 and the electron transport layer 350 to enhance the capability of injecting electrons into the electron transport layer 350 .
  • the electron injection layer 360 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 360 may include ytterbium (Yb).
  • a hole blocking layer 340 may also be disposed between the organic light-emitting layer 330 and the electron transport layer 350 .
  • 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. Since the electronic device has the organic electroluminescence device described above, it has the same beneficial effects, and details are not described here in this application.
  • the present application provides an electronic device 400 , and the electronic device 400 includes any organic electroluminescent device described in the above organic electroluminescent device embodiments.
  • the electronic device 400 may be 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. Since the electronic device 400 has any of the organic electroluminescence devices described in the above organic electroluminescence device embodiments, it has the same beneficial effects, and details are not described herein again.
  • 1,2-Dibromo-3-chlorobenzene (80.0 g; 298.7 mmol), phenylboronic acid (36.5 g; 298.7 mmol), tetrakis(triphenylphosphine)palladium (6.9 g; 6.0 mmol), potassium carbonate (103.2 g; 746.7 mmol), tetrabutylammonium bromide (19.2 g; 59.7 mmol) was added to the flask, and a mixed solvent of toluene (600 mL), ethanol (150 mL) and water (150 mL) was added, and the temperature was raised to 80 under nitrogen protection.
  • intermediate b-2, intermediate c-2 and intermediate d-2 shown in Table 2 were synthesized by referring to the method of intermediate a-2 by replacing intermediate a-1 with reactant B in Table 2.
  • intermediate b-3, intermediate c-3 and intermediate d-3 shown in Table 3 were synthesized by referring to the method of intermediate a-3 by substituting reactant C in table 3 for intermediate a-2.
  • intermediate b-II, intermediate c-II and intermediate d-II shown in Table 4 were synthesized by referring to the method of intermediate a-II by substituting reactant D in table 4 for intermediate a-1.
  • reaction solution after the dropwise addition, the reaction solution was raised to 80 ° C and stirred for 2 hours; then the reaction solution was lowered to room temperature, the precipitated solid was filtered, the filter cake was rinsed with water and ethanol, and the crude product was obtained by drying; using dichloromethane/ The crude product was purified by silica gel column chromatography in n-heptane system to obtain intermediate a-III (20.0 g; 89%) as a white solid.
  • intermediate b-III, intermediate c-III and intermediate d-III shown in Table 5 were synthesized by referring to the method of intermediate a-III by substituting reactant E in table 5 for intermediate a-II.
  • intermediate a-3 with reactant F in Table 6, and synthesize intermediate b-4, intermediate c-4, intermediate d-4, intermediate a- shown in Table 6 with reference to the method of intermediate a-4 IV, intermediate b-IV, intermediate c-IV and intermediate d-IV.
  • Anode 1 was prepared by the following procedure: ITO thickness was The ITO substrate was cut into a size of 40mm (length) ⁇ 40mm (width) ⁇ 0.7mm (thickness), and a photolithography process was used to prepare it into an experimental substrate with cathode, anode and insulating layer patterns.
  • O 2 N 2 plasma is used for surface treatment to increase the work function of the anode, and organic solvent can be used to clean the surface of the ITO substrate to remove impurities and oil stains on the surface of the ITO substrate. It should be noted that the ITO substrate can also be cut into other sizes according to actual needs, and the size of the ITO substrate in this application is not specifically limited.
  • HAT-CN was vacuum evaporated on the experimental substrate (anode) to form a thickness of A hole injection layer (HIL) of
  • NPB was vacuum evaporated on the hole injection layer to form a thickness of the hole transport layer.
  • Compound 2 was vacuum evaporated on the hole transport layer to form a thickness of the hole adjusting layer.
  • CBP is used as a host and Ir(ppy) 3 is used as a dopant.
  • Co-evaporation is carried out according to the ratio of 90%: 10% of the material weight to form a thickness of green organic light-emitting layer (EML).
  • EML green organic light-emitting layer
  • TPyQB and LiQ were mixed in a weight ratio of 1:1 and evaporated to form Thick electron transport layer (ETL), Yb 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
  • the thickness of vacuum evaporation on the above-mentioned cathode is CP-1, thus completing the fabrication of organic electroluminescent devices.
  • the organic electroluminescent device was prepared by the same method as in Example 1, except that the compounds shown in Table 9 were used instead of Compound 2 when forming the hole adjustment layer.
  • the performance parameters of each device are shown in Table 9. .
  • the organic electroluminescent device was prepared by the same method as in Example 1, except that Compound A-Compound F were used instead of Compound 2 when forming the hole adjusting layer.
  • the performance parameters of each device are shown in Table 9. Wherein, the structural formulas of compound A-compound F are respectively as follows:
  • the IVL (current, voltage, brightness) data are compared with the test results at 10 mA/cm 2 , and the T95 lifetime is the test results at a current density of 20 mA/cm 2 .
  • the organic compounds of the present application have improved efficiency and lifespan compared with the compounds A-D of Comparative Examples 1-4.
  • the reason may be that the organic compound of the present application avoids the disadvantage of poor thermal stability of 9,9-dimethylfluorene by introducing a phenyl group between the arylamine group and the 9-position of the fluorene group.

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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，有机化合物的结构如式（1）所示，将本申请的有机化合物用作有机电致发光器件的空穴调整层材料时可以提高器件的发光效率和使用寿命。

Description

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
相关申请的交叉引用
本申请要求于2021年3月3日递交的申请号为202110237053.5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。
现有技术中，专利CN107459466A公开了可以在有机电致发光器件中制备的发光层材料。然而，依然有必要继续研发新型的材料，以进一步提高电子元器件的性能。
发明内容
本申请的目的是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，将本申请的有机化合物用于有机电致发光器件的空穴调整层材料时可以提高器件的发光效率和使用寿命。
为了实现上述目的，本申请第一方面提供一种有机化合物，所述有机化合物的结构如式1所示：
Figure PCTCN2021135441-appb-000001
式1中，环A为金刚烷基或降冰片烷基；
L 1、L 2和L 3相同或不同，且各自独立地选自单键、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；
R 1、R 2、R 3、R 4和R 5彼此相同或不同，且各自独立地选自氘、卤素基团、氰基、碳原子数为1-20的烷基、碳原子数为3-20的环烷基、碳原子数为6-30的芳基、碳原子数为3-30的杂芳基；
R 6选自氘、卤素基团、氰基、碳原子数为1-20的烷基、碳原子数为3-20的环烷基、碳原子数为3-30的杂芳基；
n 1、n 2、n 4和n 6彼此相同或不同，且各自独立地选自0、1、2、3或4；n 3选自0、1、2或3；
n 5选自0、1、2、3、4或5；
Ar 1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；
所述L 1、L 2、L 3和Ar 1中的取代基分别独立地选自氘、卤素基团、氰基、碳原子数为3-20的杂芳基、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2-6的烯基、碳原子数为2-6的炔基、碳原子数为3-10的环烷基、碳原子数为2-10的杂环烷基、碳原子数为5-10的环烯基、碳原子数为4-10的杂环烯基、碳原子数为1-10的烷氧基、碳原子数为1-10的烷硫基、碳原子数为6-18的芳氧基、碳原子数为6-18的芳硫基、碳原子数为6-18的膦氧基。
本申请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提供的有机化合物；
优选地，所述功能层包括空穴调整层，所述空穴调整层含有所述的有机化合物。
本申请第三方面提供一种电子装置，包括本申请第二方面提供的有机电致发光器件。
通过上述技术方案，本申请的有机化合物将三芳胺基团中一个芳基固定为通过亚苯基连接的9-芴基，并且与芴类螺环结构相结合，其中，亚苯基连接的9-芴基相比于直接连接芴基的1-4号位，避免了9,9-二取代芴基热稳定性差的缺点，同时充分利用了芴优良的空穴传输特性，结合N与苯基连接位置的调节，使得此类材料具有优良的空间构型，具有更易调控的HOMO能级水平，具有优于1-4号位连接的二取代芴基的空穴传输能力，且不易结晶，用于有机电致发光器件，可以极大提高器件的发光效率。同时结合环烷基-螺芴型结构优秀的空穴传输能力及优良的成膜性，使得此类材料在保持高效率的同时，能保持相对较长的寿命。特别是在芴环上引入金刚烷基或降冰片基，能够提供良好的迁移率。
将本申请有机化合物用作有机电致发光器件的绿光器件的空穴调整层材料时，将有效提升器件的发光效率以及寿命。
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是本申请的有机电致发光器件的一种具体实施方式的结构示意图；
图2是包括本申请的有机电致发光器件的电子装置的一种具体实施方式的结构示意图。
附图标记说明
100阳极                   200阴极                 300功能层
310空穴注入层             321空穴传输层           322空穴调整层
330有机发光层             340空穴阻挡层           350电子传输层
360电子注入层             400电子装置
具体实施方式
以下结合附图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。
用语“该”和“所述”用以表示存在一个或多个要素/组成部分/等；用语“包括”“包含”和“含有”用以表示开放式的包括在内的意思并且是指除了列出的要素/组成部分/等之外还可存在另外的要素/ 组成部分/等。
本申请第一方面提供一种有机化合物，所述有机化合物的结构如式1所示：
Figure PCTCN2021135441-appb-000002
式1中，环A为金刚烷基或降冰片烷基；
L 1、L 2和L 3相同或不同，且各自独立地选自单键、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；
R 1、R 2、R 3、R 4和R 5彼此相同或不同，且各自独立地选自氘、卤素基团、氰基、碳原子数为1-20的烷基、碳原子数为3-20的环烷基、碳原子数为6-30的芳基、碳原子数为3-30的杂芳基；
R 6选自氘、卤素基团、氰基、碳原子数为1-20的烷基、碳原子数为3-20的环烷基、碳原子数为3-30的杂芳基；
n 1、n 2、n 4和n 6彼此相同或不同，且各自独立地选自0、1、2、3或4；n 3选自0、1、2或3；
n 5选自0、1、2、3、4或5；
Ar 1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；
所述L 1、L 2、L 3和Ar 1中的取代基分别独立地选自氘、卤素基团、氰基、碳原子数为3-20的杂芳基、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2-6的烯基、碳原子数为2-6的炔基、碳原子数为3-10的环烷基、碳原子数为2-10的杂环烷基、碳原子数为5-10的环烯基、碳原子数为4-10的杂环烯基、碳原子数为1-10的烷氧基、碳原子数为1-10的烷硫基、碳原子数为6-18的芳氧基、碳原子数为6-18的芳硫基、碳原子数为6-18的膦氧基。
优选地，n 1、n 2、n 3、n 4、n 5和n 6均为0。
在本申请中，所采用的描述方式“各……独立地为”、“……各自独立地为”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 PCTCN2021135441-appb-000003
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例如可以选自氘、卤素基团、氰基、碳原子数为3-20的杂芳基、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2-6 的烯基、碳原子数为2-6的炔基、碳原子数为3-10的环烷基、碳原子数为2-10的杂环烷基、碳原子数为5-10的环烯基、碳原子数为4-10的杂环烯基、碳原子数为1-10的烷氧基、碳原子数为1-10的烷硫基、碳原子数为6-18的芳氧基、碳原子数为6-18的芳硫基、碳原子数为6-18的膦氧基。
在本申请中，取代或未取代的官能团的碳原子数，指的是该官能团及其上的取代基中的所有碳原子数。举例而言，若Ar 1选自碳原子数为30的取代的芳基，则芳基及其上的取代基的所有碳原子数为30；再举例而言，若L 1选自碳原子数为15的取代的亚芳基，则亚芳基及其上的取代基的所有的碳原子数为15。
在本申请中，碳原子数指的是所有碳原子数。举例而言：L 1为取代的碳原子数为12的亚芳基，则亚芳基及其中的取代基的所有碳原子数为12。例如：Ar 1为
Figure PCTCN2021135441-appb-000004
则其碳原子数为7；L 1为
Figure PCTCN2021135441-appb-000005
其碳原子数为12。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。
在本申请中，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，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、9,9-二甲基芴基、螺二芴基、茚基、蒽基、菲基、二联苯基、三联苯基、四联苯基、五联苯基、苯并[9,10]菲基、芘基、荧蒽基、苯并荧蒽基、
Figure PCTCN2021135441-appb-000006
基、苝基等。本申请的“芳基”上可以有一个或多个连接键与分子其余部分相连。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(-CN)、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。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20的取代的芳基，指的是芳基和取代基的总碳原子数为20。
本申请中，碳原子数为6-30的芳基的碳原子数例如为6(苯基)、10(萘基)、12(例如联苯基)、14、15、16、18、20、24、25等。
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、联苯基、三联苯基、菲基、蒽基、芴基等。
本申请中，涉及的亚芳基是指芳基进一步失去氢原子所形成的基团。在本申请的一些实施方案中，亚芳基包含芳基进一步失去一个或两个或更多个氢原子所形成的基团，例如次芳基。芳基的定义可以适用于亚芳基和次芳基。
在本申请中，杂芳基是指环中包含1、2、3、4、5、6或7个杂原子的一价芳香环或其衍生物，其中所述的杂原子可以是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、吩噻嗪基、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。可以理解的是，“杂芳基”上可以有一个键、两个键或多个键与分子中其他部分相连接。
在本申请中，碳原子数为3-30的杂芳基的碳原子数例如为3、4、5、8、9、12、15、18、24等。碳原子数为6-18的亚芳基碳原子数例如为6、12、18等。
在本申请中，作为取代基的杂芳基具体实例包括但不限于：菲咯啉基、呋喃基、噻吩基、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。
在本申请中，“烷基”是指饱和的直链或支链一价烃基基团，其中，所述烷基可以任选地被一个或多个本申请描述的取代基所取代。具体而言，碳原子数为1-20的烷基可以为碳原子数为1-20的直链烷基，或碳原子数为3-20的支链烷基。碳原子数例如可以为1、2、3、4、5、6、7、8、9、10、11、12、13、14、15、16、17、18、19、20。在一些实施方案中，本申请中的烷基含有1-10个碳原子；在另一些实施方案中，本申请中的烷基含有1-6个碳原子；在又一些实施方案中，本申请中的烷基含有1-4个碳原子；在另一些实施方案中，本申请中的烷基含有1-3个碳原子。烷基的具体实例包括甲基、乙基、丙基、正丙基、异丙基、丁基、正丁基、异丁基、叔丁基、仲丁基、1-甲基-丁基、1-乙基-丁基、戊基、正戊基、异戊基、新戊基、叔戊基、己基、正己基、2-甲基戊基、2-乙基丁基、庚基、正庚基、辛基、正辛基、叔辛基、正壬基、癸基等，但并不限于此。本申请中的碳原子数1-4的烷基的实例包括但不限于：甲基(Me、-CH 3)、乙基(Et、-CH 2CH 3)、正丙基(n-Pr、-CH 2CH 2CH 3)、异丙基(i-Pr、-CH(CH 3) 2)、正丁基(n-Bu、-CH 2CH 2CH 2CH)、叔丁基(t-Bu,-C(CH 3) 3)等。
在本申请中，卤素基团可以为氟、氯、溴、碘。
在本申请中，碳原子数为1-10的卤代烷基具体实例包括但不限于，三氟甲基。
本申请文件中，基团未明确指明是否为取代的，均为未取代的。
本申请中连接键用
Figure PCTCN2021135441-appb-000007
表示。
本申请中，不定位连接键是指从环体系中伸出的单键
Figure PCTCN2021135441-appb-000008
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 PCTCN2021135441-appb-000009
再举例而言，如下式(X')中所示地，式(X')所表示的二苯并呋喃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 PCTCN2021135441-appb-000010
在本申请一种具体实施方式中，Ar 1选自碳原子数为6-20的取代或者未取代的芳基、碳原子数为12-20的取代或者未取代的杂芳基。
可选地，Ar 1中的取代基选自氘、卤素基团、氰基、碳原子数为1-5的烷基、碳原子数为6-12的芳基、碳原子数为12-14的杂芳基、碳原子数为1-5的卤代烷基。
具体地，Ar 1中的取代基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、菲基、二甲基芴基、二苯并呋喃基、二苯并噻吩基、咔唑基、三氟甲基等。
在本申请另一种实施方式中，Ar 1选自取代或未取代的苯基、取代或未取代的萘基、取代或未取代的联苯基、取代或未取代的菲基、取代或未取代的二甲基芴基、取代或未取代的三联苯基、取代或未取代的9,9-二甲基-9H-9-硅芴基、取代或未取代的二苯并噻吩基、取代或未取代的二苯并呋喃基、取代或未取代的咔唑基。
在本申请一种具体实施方式中，Ar 1选自取代或者未取代的基团W，所述未取代的基团W选自如下基团所组成的组：
Figure PCTCN2021135441-appb-000011
其中，
Figure PCTCN2021135441-appb-000012
表示化学键；基团W被一个或多个取代基所取代时，各所述取代基相同或不同，且各自独立地选自：氘、氟、氰基、甲基、乙基、正丙基、异丙基、叔丁基、苯基、萘基、联苯基、三氟甲基。
可选地，Ar 1选自如下基团所组成的组：
Figure PCTCN2021135441-appb-000013
Figure PCTCN2021135441-appb-000014
在本申请一种具体实施方式中，所述L 1、L 2和L 3相同或不同，且各自独立地选自单键、碳原子数为6-20的取代或未取代的亚芳基、碳原子数为12-20的取代或未取代的亚杂芳基。
可选地，所述L 1、L 2和L 3中的取代基分别独立地选自氘、卤素基团、氰基、碳原子数为1-5的烷基、碳原子数为6-12的芳基。
具体地，所述L 1、L 2和L 3中的取代基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。
在本申请一种具体实施方式中，所述L 1、L 2和L 3相同或不同，且各自独立地选自单键、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、取代或未取代的亚联苯基、取代或未取代的亚芴基、取代或未取代的亚咔唑基、取代或未取代的亚二苯并呋喃基、取代或未取代的亚二苯并噻吩基、取代或未取代的N-苯基咔唑亚基。
在本申请另一种实施方式中，所述L 1、L 2和L 3分别独立地选自单键、取代或未取代的基团V；所述未取代的基团V选自如下基团所组成的组：
Figure PCTCN2021135441-appb-000015
其中，
Figure PCTCN2021135441-appb-000016
表示化学键；基团V被一个或多个取代基所取代时，各所述取代基相同或不同，且各自独立地选自：氘、氟、氰基、甲基、乙基、正丙基、异丙基、叔丁基、苯基、萘基。
可选地，
Figure PCTCN2021135441-appb-000017
选自以下基团组成的组：
Figure PCTCN2021135441-appb-000018
Figure PCTCN2021135441-appb-000019
可选地，L 3选自单键或亚苯基。
进一步可选地，L 3选自单键或如下基团组成的组：
Figure PCTCN2021135441-appb-000020
在本申请一种具体实施方式中，所述R 1、R 2、R 3、R 4和R 5彼此相同或不同，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3-15的环烷基、碳原子数为6-25的芳基、碳原子数为3-25的杂芳基；
优选地，所述R 1、R 2、R 3、R 4和R 5彼此相同或不同，且各自独立地选自氘、卤素基团、氰基、甲基、乙基、正丙基、异丙基、环丙基、环丁基、环戊基、苯基、萘基、菲基、蒽基、咔唑基、二苯并噻吩基、二苯并呋喃基。
R 6选自氘、卤素基团、氰基、碳原子数为1-10的烷基、碳原子数为3-15的环烷基、碳原子数为3-25的杂芳基；
优选地，所述R 6选自氘、卤素基团、氰基、甲基、乙基、正丙基、异丙基、环丙基、环丁基、环戊基、咔唑基、二苯并噻吩基、二苯并呋喃基。
在本申请中，所述金刚烷基指的是未取代的金刚烷基，所述降冰片烷基指的是未取代的降冰片烷基。
在本申请一种实施方式中，所述环A选自以下基团：
Figure PCTCN2021135441-appb-000021
在本申请一种具体实施方式中，所述有机化合物选自以下有机化合物组成的组：
Figure PCTCN2021135441-appb-000022
Figure PCTCN2021135441-appb-000023
Figure PCTCN2021135441-appb-000024
Figure PCTCN2021135441-appb-000025
Figure PCTCN2021135441-appb-000026
Figure PCTCN2021135441-appb-000027
Figure PCTCN2021135441-appb-000028
Figure PCTCN2021135441-appb-000029
Figure PCTCN2021135441-appb-000030
Figure PCTCN2021135441-appb-000031
Figure PCTCN2021135441-appb-000032
Figure PCTCN2021135441-appb-000033
Figure PCTCN2021135441-appb-000034
Figure PCTCN2021135441-appb-000035
Figure PCTCN2021135441-appb-000036
Figure PCTCN2021135441-appb-000037
Figure PCTCN2021135441-appb-000038
Figure PCTCN2021135441-appb-000039
Figure PCTCN2021135441-appb-000040
本申请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。
举例而言，如图1所示，有机电致发光器件可以包括相对设置的阳极100和阴极200，以及设于阳极100和阴极200之间的功能层300；功能层300含有本申请所提供的有机化合物。在本申请的一种具体实施方式中，功能层300包括空穴调整层322，空穴调整层322包含本申请所提供的有机化合物。
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。
在本申请的一种具体实施方式中，有机电致发光器件可以包括依次层叠设置的阳极100、空穴传输层321、空穴调整层322、作为能量转化层的有机发光层330、电子传输层350和阴极200。
在本申请中，阳极100含有阳极材料，阳极材料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。优选地，阳极100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。
在本申请中，如图1所示，在阳极100和空穴传输层321之间还可以设置有空穴注入层310，以增强向空穴传输层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。在本申请的一种实施方式中，空穴注入层310可以由HAT-CN组成。
在本申请中，在空穴注入层310和空穴调整层322之间还可以设置有空穴传输层321，空穴传输层321还可以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。举例而言，在本申请的一种实施方式中，空穴传输层321中含有化合物NPB，空穴传输层321紧邻空穴注入层310。
在本申请中，功能层300包括空穴调整层322，空穴调整层322包含本申请所提供的有机化合物。其中，空穴调整层322既可以由本申请所提供的有机化合物组成，也可以由本申请所提供的有机化合物和其他材料共同组成。
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。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的主体材料可以为金属螯合类化合物、双苯乙烯基衍生物、芳香族胺衍生物、二苯并呋喃衍生物或者其他类型的材料，本申请对此不做特殊的限制。有机发光层330的掺杂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。例如，有机发光层330可以含有CBP和Ir(ppy) 3。
在本申请中，阴极200含有阴极材料，阴极材料优选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。优选包括包含银和镁的金属电极作为阴极。
可选地，电子传输层350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350可以由TPyQB和LiQ组成。
在本申请中，如图1所示，在阴极200和电子传输层350之间还可以设置有电子注入层360，以增强向电子传输层350注入电子的能力。电子注入层360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。在本申请的一种实施方式中，电子注入层360可以包括镱(Yb)。
在本申请一种具体实施方式中，在有机发光层330和电子传输层350之间还可以设置有空穴阻挡层340。
本申请第三方面提供一种电子装置，包括本申请第二方面所述的有机电致发光器件。由于该电子装置具有上述所描述的有机电致发光器件，因此具有相同的有益效果，本申请在此不再赘述。
举例而言，如图2所示，本申请提供电子装置400，该电子装置400包括上述有机电致发光器件实施方式所描述的任意一种有机电致发光器件。该电子装置400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。由于该电子装置400具有上述有机电致发光器件实施方式所描述的任意一种有机电致发光器件，因此具有相同的有益效果，本申请在此不再赘述。
下面通过实施例来进一步说明本申请，但是本申请并不因此而受到任何限制
合成例1中间体的制备
Figure PCTCN2021135441-appb-000041
将1,2-二溴-3-氯苯(80.0g；298.7mmol)，苯硼酸(36.5g；298.7mmol)，四(三苯基膦)钯(6.9g；6.0mmol)，碳酸钾(103.2g；746.7mmol)，四丁基溴化铵(19.2g；59.7mmol)加入烧瓶中，并加入甲苯(600mL)、乙醇(150mL)和水(150mL)的混合溶剂，氮气保护下，升温至80℃，保持温度搅拌18小时；将反应液冷却至室温，停止搅拌，反应液水洗后分离有机相，使用无水硫酸镁 干燥，减压除去溶剂，得到粗品；使用二氯甲烷/正庚烷作为流动相对粗品进行硅胶柱色谱提纯，得到白色固体产物中间体a-1(42.0g；53％)。
以表1中反应物A替代1,2-二溴-3-氯苯，参照中间体a-1的方法合成表1所示的中间体b-1和中间体c-1。
表1
Figure PCTCN2021135441-appb-000042
Figure PCTCN2021135441-appb-000043
将1-溴-2-碘苯(50g；176.73mmol)，3-氯苯硼酸(27.64g；176.73mmol)，四(三苯基膦)钯(1.02g；0.88mmol)，碳酸钾(48.79g；353.4mmol)，四丁基溴化铵(11.4g；35.3mmol)加入烧瓶中，并加入甲苯(400mL)、乙醇(100mL)和水(100mL)的混合溶剂，氮气保护下，升温至80℃，保持温度搅拌12小时；将反应液冷却至室温，停止搅拌，反应液水洗后分离有机相，使用无水硫酸镁干燥，减压除去溶剂，得到粗品；使用二氯甲烷/正庚烷作为流动相对粗品进行硅胶柱色谱提纯，得到白色固体产物中间体d-1(29.3g；62％)。
Figure PCTCN2021135441-appb-000044
将中间体a-1(42.0g；157.9mmol)和四氢呋喃(300mL)加入烧瓶中，氮气保护下，降温至-78℃，于搅拌条件下，滴加正丁基锂的四氢呋喃(2.5M)溶液(95mL；236.9mmol)，滴加完毕后保温搅拌1小时，保持-78℃滴加溶有金刚烷酮(19.0g；126.3mmol)的四氢呋喃(100mL)溶液，滴加完毕后保温1小时后升至室温，搅拌24小时；向反应液中加入盐酸(12M)(26.3mL；315.8mmol)的水(100mL)溶液，搅拌1小时；将反应液分液，有机相使用水洗至中性，加入无水硫酸镁干燥，减压除去溶剂得到粗品；使用乙酸乙酯/正庚烷体系对粗品进行硅胶柱色谱提纯，得到白色固体产物中间体a-2(25.8g；48％)。
以表2中反应物B替代中间体a-1，参照中间体a-2的方法合成表2所示的中间体b-2、中间体c-2和中间体d-2。
表2
Figure PCTCN2021135441-appb-000045
Figure PCTCN2021135441-appb-000046
将中间体a-2(25.8g；76.3mmol)和冰醋酸(300mL)加入烧瓶中，氮气保护常温搅拌条件下缓慢滴加浓硫酸(98％)(0.8mL；15.3mmol)的醋酸(20mL)溶液，滴加完毕后升至80℃，搅拌2小时；降至室温，过滤析出的固体，使用水和乙醇淋洗滤饼，烘干得到粗品；使用二氯甲烷/正庚烷体系对粗品进行硅胶柱色谱提纯，得到白色固体中间体a-3(20.4g；84％)。
以表3中反应物C替代中间体a-2，参照中间体a-3的方法合成表3所示的中间体b-3、中间体c-3和中间体d-3。
表3
Figure PCTCN2021135441-appb-000047
Figure PCTCN2021135441-appb-000048
Figure PCTCN2021135441-appb-000049
将中间体a-1(42.0g；157.9mmol)和四氢呋喃(300mL)加入烧瓶中，氮气保护下，降温至-78℃，于搅拌条件下，滴加正丁基锂的四氢呋喃(2.5M)溶液(95mL；236.9mmol)，滴加完毕后保温搅拌1小时，保持-78℃，向反应液滴加溶有降冰片酮(17.29g；156.98mmol)的四氢呋喃(100mL)溶液，滴加完毕后保温1小时后升至室温，搅拌24小时；向反应液中加入盐酸(12M)(26.3mL；315.8mmol)的水(100mL)溶液，搅拌1小时；将反应液分液，有机相使用水洗至中性，加入无水硫酸镁干燥，减压除去溶剂得到粗品；使用乙酸乙酯/正庚烷体系对粗品进行硅胶柱色谱提纯，得到白色固体产物中间体a-Ⅱ(23.92g；51％)。
以表4中反应物D替代中间体a-1，参照中间体a-Ⅱ的方法合成表4所示的中间体b-Ⅱ、中间体c-Ⅱ和中间体d-Ⅱ。
表4
Figure PCTCN2021135441-appb-000050
Figure PCTCN2021135441-appb-000051
将中间体a-Ⅱ(23.92g；80.05mmol)和冰醋酸(300mL)加入烧瓶中，氮气保护常温搅拌条件下缓慢滴加浓硫酸(98％)(0.8mL；15.3mmol)的醋酸(20mL)溶液，滴加完毕后将反应液升至80℃，搅拌2小时；然后将反应液降至室温，过滤析出的固体，使用水和乙醇淋洗滤饼，烘干得到粗品；使用二氯甲烷/正庚烷体系对粗品进行硅胶柱色谱提纯，得到白色固体中间体a-Ⅲ(20.0g；89％)。
以表5中反应物E替代中间体a-Ⅱ，参照中间体a-Ⅲ的方法合成表5所示的中间体b-Ⅲ、中间体c-Ⅲ和中间体d-Ⅲ。
表5
Figure PCTCN2021135441-appb-000052
合成例2化合物2的合成
Figure PCTCN2021135441-appb-000053
将中间体a-3(12.57g；39.17mmol)，3-氨基联苯(6.63g；39.17mmol)，三(二亚苄基丙酮)二钯(0.18g；0.2mmol)，2-二环己基磷-2’,4’,6’-三异丙基联苯(0.2g；0.4mmol)，叔丁醇钠(5.64g；58.76mmol)和甲苯(50mL)加入烧瓶中，氮气保护条件下，将反应液在110℃回流搅拌4小时；将反应液降至室温，反应液使用水洗，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b-3(11.55g；65％)。质谱：m/z＝454.13[M+H] +。
Figure PCTCN2021135441-appb-000054
将中间体b-3(11.55g；25.46mmol)，原料RM-A(10.12g；25.46mmol)，三(二亚苄基丙酮)二钯(0.23g；0.25mmol)，2-二环己基磷-2’,4’,6’-三异丙基联苯(0.23g；0.46mmol)，叔丁醇钠(3.67g；38.19mmol)和甲苯(96mL)加入烧瓶中，氮气保护条件下，将反应液在108℃回流搅拌4小时；降至室温，反应液使用水洗，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，得到白色固体化合物2(6.86g；35％)。质谱：m/z＝770.3[M+H] +。
合成例3化合物450的合成
Figure PCTCN2021135441-appb-000055
将中间体c-Ⅲ(12.57g；39.17mmol)，中间体c(13.06g；39.17mmol)，三(二亚苄基丙酮)二钯(0.18g；0.2mmol)，2-二环己基磷-2’,4’,6’-三异丙基联苯(0.2g；0.4mmol)，叔丁醇钠(5.64g；58.76mmol)和甲苯(50mL)加入烧瓶中，氮气保护条件下于110℃回流搅拌4小时；降至室温，反应液使用水洗，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c-4(10.86g；48％)。
Figure PCTCN2021135441-appb-000056
将中间体c-4(10.86g；18.8mmol)，3-溴二苯并噻吩(4.92g；18.8mmol)，三(二亚苄基丙酮)二钯(0.23g；0.25mmol)，2-二环己基磷-2’,4’,6’-三异丙基联苯(0.23g；0.46mmol)，叔丁醇钠(3.67g；38.19mmol)和甲苯(96mL)加入烧瓶中，氮气保护条件下，将反应液在108℃回流搅拌4小时；降至室温，反应液使用水洗，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，得到化合物450(6.14g；43％)。质谱：m/z＝760.3[M+H] +。
合成例4化合物285的合成
Figure PCTCN2021135441-appb-000057
将中间体a-3(20.4g；63.7mmol)，联硼酸频那醇酯(19.4g；76.5mmol)，三(二亚苄基丙酮)二钯(0.6g；0.6mmol)，2-二环己基磷-2’,4’,6’-三异丙基联苯(0.6g；1.3mmol)，醋酸钾(12.5g；127.4mmol)和1,4-二氧六环(150mL)加入烧瓶中，氮气保护条件下，将反应液在100℃回流搅拌16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a-4(13.3g；51％)。
以表6中反应物F替代中间体a-3，参照中间体a-4的方法合成表6所示的中间体b-4、中间体c-4、中间体d-4、中间体a-Ⅳ、中间体b-Ⅳ、中间体c-Ⅳ和中间体d-Ⅳ。
表6
Figure PCTCN2021135441-appb-000058
Figure PCTCN2021135441-appb-000059
Figure PCTCN2021135441-appb-000060
将中间体b-4(13.3g；32.3mmol)，3-氯苯胺(4.12g；32.3mmol)，四(三苯基膦)钯(0.7g；0.6mmol)，碳酸钾(11.1g；80.7mmol)，四丁基溴化铵(2.1g；6.5mmol)加入烧瓶中，并加入甲苯(80mL)、乙醇(20mL)和水(20mL)的混合溶剂，氮气保护下，升温至80℃，保持温度搅拌24小时；冷却至室温，停止搅拌，反应液水洗后分离有机相，使用无水硫酸镁干燥，减压除去溶剂，得到粗品；使用二氯甲烷/正庚烷作为流动相对粗品进行硅胶柱色谱提纯，得到白色固体产物中间体b-5(7.56g；62％)。
Figure PCTCN2021135441-appb-000061
将中间体b-5(7.56g；20.0mmol)，溴苯(3.14g；20.0mmol)，三(二亚苄基丙酮)二钯(0.18g；0.2mmol)，2-二环己基磷-2’,4’,6’-三异丙基联苯(0.2g；0.4mmol)，叔丁醇钠(5.64g；58.76mmol)和甲苯(50mL)加入烧瓶中，氮气保护条件下，将反应液在105℃回流搅拌3小时；将反应液降至室温，反应液使用水洗，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b-6(6.35g；70％)。质谱：m/z＝454.13[M+H] +。
Figure PCTCN2021135441-appb-000062
将中间体b-6(6.35g；14mmol)，溴苯(5.56g；14.0mmol)，三(二亚苄基丙酮)二钯(0.18g；0.2mmol)，2-二环己基磷-2’,4’,6’-三异丙基联苯(0.2g；0.4mmol)，叔丁醇钠(5.64g；58.76mmol)和甲苯(50mL)加入烧瓶中，氮气保护条件下，将反应液105℃回流搅拌3小时；将反应液降至室温，反应液使用水洗，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，得到白色固体化合物285(6.35g；61％)。质谱：m/z＝744.26[M+H] +。
参照化合物2的合成方法，且使用原料1代替中间体a-3，原料2代替3-氨基联苯，原料3代替原料RM-A，制备表7中所示的化合物。其中，化合物的编号、结构、原料、最后一步的合成收率、表征数据等如表7所示。
表7：化合物的结构、制备及表征数据
Figure PCTCN2021135441-appb-000063
Figure PCTCN2021135441-appb-000064
Figure PCTCN2021135441-appb-000065
Figure PCTCN2021135441-appb-000066
Figure PCTCN2021135441-appb-000067
部分化合物核磁数据如下表8所示
表8
Figure PCTCN2021135441-appb-000068
实施例1：绿色有机电致发光器件的制作
通过以下过程制备阳极1：将ITO厚度为
Figure PCTCN2021135441-appb-000069
的ITO基板切割成40mm(长)×40mm(宽)×0.7mm(厚)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，并可利用紫外臭氧以及O 2:N 2等离子进行表面处理，以增加阳极的功函数，并可采用有机溶剂清洗ITO基板表面，以清除ITO基板表面的杂质及油污。需要说明的是，ITO基板还可以根据实际需要切割成其他尺寸，在此不对本申请中ITO基板的尺寸做特殊限定。
在实验基板(阳极)上真空蒸镀一层HAT-CN以形成厚度为
Figure PCTCN2021135441-appb-000070
的空穴注入层(HIL)，并且在空穴注入层上真空蒸镀NPB，以形成厚度为
Figure PCTCN2021135441-appb-000071
的空穴传输层。
在空穴传输层上真空蒸镀化合物2，形成厚度为
Figure PCTCN2021135441-appb-000072
的空穴调整层。
接着在空穴调整层上，将CBP作为主体，Ir(ppy) 3作为掺杂剂。按照材料重量90％：10％的比例进行共同蒸镀，形成厚度为
Figure PCTCN2021135441-appb-000073
的绿色有机发光层(EML)。
然后将TPyQB和LiQ以1:1的重量比进行混合并蒸镀形成
Figure PCTCN2021135441-appb-000074
厚的电子传输层(ETL)，将Yb蒸镀在电子传输层上以形成厚度为
Figure PCTCN2021135441-appb-000075
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 PCTCN2021135441-appb-000076
的阴极。
此外，在上述阴极上真空蒸镀厚度为
Figure PCTCN2021135441-appb-000077
的CP-1，从而完成有机电致发光器件的制造。
实施例以及比较例中所采用的有机化合物的结构如下所示：
Figure PCTCN2021135441-appb-000078
Figure PCTCN2021135441-appb-000079
实施例2-25
采用与实施例1相同的方法制备有机电致发光器件，不同之处仅在于，在形成空穴调整层时分别使用表9中所示的化合物替代化合物2，各器件的性能参数详见表9。
比较例1-6
采用与实施例1相同的方法制备有机电致发光器件，不同之处仅在于，在形成空穴调整层时分别使用化合物A-化合物F替代化合物2，各器件的性能参数详见表9。其中，化合物A-化合物F的结构式分别如下所示：
Figure PCTCN2021135441-appb-000080
实施例和对比例中，IVL(电流、电压、亮度)数据对比的是在10mA/cm 2下的测试结果，T95寿命是20mA/cm 2电流密度下的测试结果。
表9绿色有机电致发光器件性能
Figure PCTCN2021135441-appb-000081
Figure PCTCN2021135441-appb-000082
根据上述表9的结果可知，与使用化合物A-化合物F的比较例1-6相比，采用本申请的化合物作为空穴调整层的实施例1-实施例25的有机电致发光器件的发光效率和器件寿命均有很高提升。其中，发光效率至少提升了20.7％，寿命至少提升了43％。
从上述结果可知，本申请的有机化合物与比较例1-4的化合物A-D相比，在效率和寿命上均有所提升。究其原因，可能在于，本申请的有机化合物通过在芳胺基与芴基的9-号位之间引入苯基，避免了9,9-二甲基芴热稳定性差的缺点。
本申请的有机化合物与比较例5和6相比，本申请的有机化合物的三芳胺结构中，其中一个芳基固定为9位螺合多环烷基的芴基，另一个芳基固定为9-苯基芴基取代的亚苯基，芳胺中氮原子所连接的芳香基团之间的空间结构更匹配，具备更强的刚性和更合适的空间位阻，可以提高化合物的空穴迁移率和热稳定性。因此，当将本申请的有机化合物用作绿光器件的空穴调整层材料时，能够显著提高器件的发光效率和寿命。
以上结合附图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 (11)

  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1所示：
    Figure PCTCN2021135441-appb-100001
    式1中，环A为金刚烷基或降冰片烷基；
    L 1、L 2和L 3相同或不同，且各自独立地选自单键、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；
    R 1、R 2、R 3、R 4和R 5彼此相同或不同，且各自独立地选自氘、卤素基团、氰基、碳原子数为1-20的烷基、碳原子数为3-20的环烷基、碳原子数为6-30的芳基、碳原子数为3-30的杂芳基；
    R 6选自氘、卤素基团、氰基、碳原子数为1-20的烷基、碳原子数为3-20的环烷基、碳原子数为3-30的杂芳基；
    n 1、n 2、n 4和n 6彼此相同或不同，且各自独立地选自0、1、2、3或4；n 3选自0、1、2或3；
    n 5选自0、1、2、3、4或5；
    Ar 1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；
    所述L 1、L 2、L 3和Ar 1中的取代基分别独立地选自氘、卤素基团、氰基、碳原子数为3-20的杂芳基、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2-6的烯基、碳原子数为2-6的炔基、碳原子数为3-10的环烷基、碳原子数为2-10的杂环烷基、碳原子数为5-10的环烯基、碳原子数为4-10的杂环烯基、碳原子数为1-10的烷氧基、碳原子数为1-10的烷硫基、碳原子数为6-18的芳氧基、碳原子数为6-18的芳硫基、碳原子数为6-18的膦氧基。
  2. 根据权利要求1所述的有机化合物，其特征在于，Ar 1选自碳原子数为6-20的取代或者未取代的芳基、碳原子数为12-20的取代或者未取代的杂芳基；
    优选地，所述Ar 1中的取代基选自氘、卤素基团、氰基、碳原子数为1-5的烷基、碳原子数为6-12的芳基、碳原子数为12-14的杂芳基、碳原子数为1-5的卤代烷基。
  3. 根据权利要求1所述的有机化合物，其特征在于，所述Ar 1选自取代或者未取代的基团W，所述未取代的基团W选自如下基团所组成的组：
    Figure PCTCN2021135441-appb-100002
    其中，
    Figure PCTCN2021135441-appb-100003
    表示化学键；基团W被一个或多个取代基所取代时，各所述取代基相同或不同，且各自独立地选自：氘、氟、氰基、甲基、乙基、正丙基、异丙基、叔丁基、苯基、萘基、联苯基、三氟 甲基。
  4. 根据权利要求1所述的有机化合物，其特征在于，所述L 1、L 2和L 3相同或不同，且各自独立地选自单键、碳原子数为6-20的取代或未取代的亚芳基、碳原子数为12-20取代或未取代的亚杂芳基；
    优选地，所述L 1、L 2和L 3中的取代基各自独立地选自氘、卤素基团、氰基、碳原子数为1-5的烷基、碳原子数为6-12的芳基。
  5. 根据权利要求1所述的有机化合物，其特征在于，所述L 1、L 2和L 3相同或不同，且各自独立地选自单键、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、取代或未取代的亚联苯基、取代或未取代的亚芴基、取代或未取代的亚咔唑基、取代或未取代的亚二苯并呋喃基、取代或未取代的亚二苯并噻吩基、取代或未取代的N-苯基咔唑亚基；
    优选地，所述L 1、L 2和L 3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、联苯基。
  6. 根据权利要求1所述的有机化合物，其特征在于，所述L 1、L 2和L 3分别独立地选自单键、取代或未取代的基团V；所述未取代的基团V选自如下基团所组成的组：
    Figure PCTCN2021135441-appb-100004
    其中，
    Figure PCTCN2021135441-appb-100005
    表示化学键；基团V被一个或多个取代基所取代时，各所述取代基相同或不同，且各自独立地选自：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，其特征在于，n 1、n 2、n 3、n 4、n 5和n 6均为0。
  8. 根据权利要求1所述的有机化合物，其特征在于，所述环A选自以下基团：
    Figure PCTCN2021135441-appb-100006
  9. 根据权利要求1所述的有机化合物，其特征在于，所述有机化合物选自以下有机化合物组成的组：
    Figure PCTCN2021135441-appb-100007
    Figure PCTCN2021135441-appb-100008
    Figure PCTCN2021135441-appb-100009
    Figure PCTCN2021135441-appb-100010
    Figure PCTCN2021135441-appb-100011
    Figure PCTCN2021135441-appb-100012
    Figure PCTCN2021135441-appb-100013
    Figure PCTCN2021135441-appb-100014
    Figure PCTCN2021135441-appb-100015
    Figure PCTCN2021135441-appb-100016
    Figure PCTCN2021135441-appb-100017
    Figure PCTCN2021135441-appb-100018
    Figure PCTCN2021135441-appb-100019
    Figure PCTCN2021135441-appb-100020
    Figure PCTCN2021135441-appb-100021
    Figure PCTCN2021135441-appb-100022
    Figure PCTCN2021135441-appb-100023
    Figure PCTCN2021135441-appb-100024
    Figure PCTCN2021135441-appb-100025
  10. 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1-9中任一项所述的有机化合物；
    优选地，所述功能层包括空穴调整层，所述空穴调整层含有所述的有机化合物。
  11. 一种电子装置，其特征在于，包括权利要求10所述的有机电致发光器件。
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