WO2023273997A1 - Organic compound and application thereof - Google Patents

Organic compound and application thereof Download PDF

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Publication number
WO2023273997A1
WO2023273997A1 PCT/CN2022/100562 CN2022100562W WO2023273997A1 WO 2023273997 A1 WO2023273997 A1 WO 2023273997A1 CN 2022100562 W CN2022100562 W CN 2022100562W WO 2023273997 A1 WO2023273997 A1 WO 2023273997A1
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substituted
unsubstituted
organic compound
organic
heteroaryl
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PCT/CN2022/100562
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French (fr)
Chinese (zh)
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黄金华
黄鑫鑫
方仁杰
曾礼昌
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北京鼎材科技有限公司
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Publication of WO2023273997A1 publication Critical patent/WO2023273997A1/en

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C211/00—Compounds containing amino groups bound to a carbon skeleton
    • C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
    • C07C211/57—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton
    • C07C211/61—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton with at least one of the condensed ring systems formed by three or more rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/56—Ring systems containing three or more rings
    • C07D209/80—[b, c]- or [b, d]-condensed
    • C07D209/82—Carbazoles; Hydrogenated carbazoles
    • C07D209/86—Carbazoles; Hydrogenated carbazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/56—Ring systems containing three or more rings
    • C07D209/80—[b, c]- or [b, d]-condensed
    • C07D209/82—Carbazoles; Hydrogenated carbazoles
    • C07D209/88—Carbazoles; Hydrogenated carbazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the ring system
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    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D213/36—Radicals substituted by singly-bound nitrogen atoms
    • C07D213/38—Radicals substituted by singly-bound nitrogen atoms having only hydrogen or hydrocarbon radicals attached to the substituent nitrogen atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D307/91—Dibenzofurans; Hydrogenated dibenzofurans
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
    • C07D333/76—Dibenzothiophenes
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
    • C07F7/02—Silicon compounds
    • C07F7/08—Compounds having one or more C—Si linkages
    • C07F7/0803—Compounds with Si-C or Si-Si linkages
    • C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
    • C07F7/0812—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring
    • C07F7/0816—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring said ring comprising Si as a ring atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
    • C07F7/02—Silicon compounds
    • C07F7/08—Compounds having one or more C—Si linkages
    • C07F7/10—Compounds having one or more C—Si linkages containing nitrogen having a Si-N linkage
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/06—Systems containing only non-condensed rings with a five-membered ring
    • C07C2601/08—Systems containing only non-condensed rings with a five-membered ring the ring being saturated
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2603/00—Systems containing at least three condensed rings
    • C07C2603/02—Ortho- or ortho- and peri-condensed systems
    • C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
    • C07C2603/06—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members
    • C07C2603/10—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings
    • C07C2603/12—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings only one five-membered ring
    • C07C2603/18—Fluorenes; Hydrogenated fluorenes
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2603/00—Systems containing at least three condensed rings
    • C07C2603/93—Spiro compounds
    • C07C2603/94—Spiro compounds containing "free" spiro atoms

Definitions

  • the application belongs to the technical field of organic electroluminescent materials, and specifically relates to an organic compound and its application.
  • OLED Organic Light Emission Diodes
  • the OLED device has a sandwich-like structure, including positive and negative electrodes and an organic functional material layer sandwiched between the two electrodes; when a voltage is applied to the electrodes of the OLED device, electrons and holes are respectively injected, transported to the light-emitting region and recombined there , thereby generating excitons and emitting light.
  • the core of an OLED device is an organic functional material layer.
  • the common organic functional materials that make up the material layer include: hole injection materials, hole transport materials, hole blocking materials, electron injection materials, electron transport materials, electron blocking materials, and light-emitting hosts. Materials and luminescent guests (dye), etc.
  • Common fluorescent emitters mainly use singlet excitons generated when electrons and holes combine to emit light, and are still widely used in various OLED products.
  • Some metal complexes such as iridium complexes
  • phosphorescent emitters can simultaneously utilize triplet excitons and singlet excitons to emit light, which are called phosphorescent emitters, and their energy conversion efficiency can be up to four times higher than that of traditional fluorescent emitters.
  • Thermally Excited Delayed Fluorescence (TADF) technology promotes the transformation of triplet excitons to singlet excitons, and can still effectively utilize triplet excitons to achieve high luminous efficiency without using metal complexes.
  • Thermally-stimulated sensitized fluorescence (TASF) technology uses materials with TADF properties to sensitize light emitters through energy transfer, and can also achieve higher luminous efficiency.
  • the hole transport material has a significant impact on the performance of the device.
  • the hole transport material needs to have a suitable HOMO energy level, and a suitable energy gap between the hole material and the anode is conducive to the injection of holes and can help reduce the operating voltage.
  • the hole transport material regulates the transport balance of carriers in the device and improves the carrier mobility of the hole transport material, thereby improving the luminous efficiency and delaying the decay of the device.
  • the purpose of this application is to provide an organic compound and its application.
  • the organic compound is applied to an organic electroluminescent device, and is especially suitable as an electron blocking layer material and/or a hole transporting layer material,
  • the luminous efficiency of the device can be improved and the driving voltage can be reduced.
  • Ar 1 and Ar 2 are each independently selected from any one of substituted or unsubstituted C6-C30 aryl groups and substituted or unsubstituted C3-C30 heteroaryl groups.
  • Ar 3 is selected from any one of substituted or unsubstituted C6-C12 aryl, substituted or unsubstituted C3-C11 heteroaryl.
  • X is selected from any one of O, S, CR 1 R 2 , NR 3 or SiR 4 R 5 .
  • R 1 , R 2 , R 3 , R 4 , and R 5 are each independently selected from hydrogen, substituted or unsubstituted C1-C20 linear or branched chain alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted Or any of unsubstituted C2-C12 alkenyl, substituted or unsubstituted C2-C12 alkynyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl;
  • R 1 and R 2 are not connected or are connected to form a ring by a chemical bond
  • R 4 and R 5 are not connected or are connected to form a ring by a chemical bond
  • R f1 , R f2 , and R f3 are each independently selected from halogen, cyano, substituted or unsubstituted C1-C20 linear or branched chain alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted Any one of C2-C12 alkenyl, substituted or unsubstituted C2-C12 alkynyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl;
  • Ar 1 , Ar 2 , R 1 , R 2 , R 3 , R 4 , R 5 , R f1 , R f2 , and R f3 are each independently selected from halogen, C1-C10 straight chain or branched Alkanyl, C3-C10 cycloalkyl, C2-C10 heterocycloalkyl, C1-C10 alkoxy, C1-C10 alkylthio, C6-C30 arylamino, C3-C30 heteroarylamino, C6- At least one of C30 aryl or C3-C30 heteroaryl;
  • the substituted substituent in Ar 3 is at least one selected from halogen, C1-C6 linear or branched chain alkyl, C3-C6 cycloalkyl, C1-C6 alkoxy or C1-C6 alkylthio.
  • k 1 and k 2 are each independently an integer of 0-3, such as 0, 1, 2 or 3; k 3 is an integer of 0-4, such as 0, 1, 2, 3 or 4.
  • the organic compound provided by this application has a structure as shown in formula I.
  • the arylamine N is directly connected to the condensed structure of the dibenzo five-membered ring, which is conducive to the improvement of the mobility, and the molecular packing is denser; and N is connected to the 2-position of the dibenzo five-membered ring fused structure, which can further improve the mobility and performance of the device;
  • N, Ar 1 and Ar 2 are located adjacent to the benzene ring, which can make the LUMO energy The level becomes shallow, thereby further blocking the diffusion of excitons to the hole layer, and improving the performance of the device;
  • the Ar 3 is selected from C6-C12 aryl or C3-C11 heteroaryl with a smaller molecular weight, which is beneficial to the overall molecular weight of the compound Controlling, so as to avoid excessive evaporation temperature in the device preparation process due to excessive molecular weight, which is more conducive to production.
  • halogens can all be fluorine, chlorine, bromine or iodine.
  • the following descriptions refer to the same, and all have the same meaning.
  • the "substituted or unsubstituted” group may be substituted with one substituent, or may be substituted with multiple substituents.
  • substituents at least 2
  • they may be the same or different Substituents; when the same expressions are mentioned below, they all have the same meaning, and the selection range of the substituents is as shown above, and will not be repeated.
  • hydrogen (H) includes 1 H (protium), 2 H (deuterium, D), 3 H ( tritium, T), etc.
  • carbon (C) includes 12 C, 13 C, etc.
  • heteroatoms of the heteroaryl group are selected from N, O, S, P, B, Si or Se.
  • the expression of the ring structure crossed by "—" indicates that the linking site is at any position on the ring structure that can form a bond.
  • the expression of Ca-Cb means that the number of carbon atoms of the group is a-b, unless otherwise specified, generally speaking, the number of carbon atoms does not include the number of carbon atoms of the substituent.
  • each independently means that when there are plural subjects, they may be the same or different from each other.
  • the C6-C30 can all be C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26 or C28, etc.
  • the C3-C30 can all be C3, C4, C5, C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26 or C28, etc.
  • the C6-C12 can all be C6, C9, C10, or C12, etc.; the C3-C11 can all be C3, C4, C5, C6, C9, or C10, etc.
  • the C1-C20 can all be C2, C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18 or C19, etc.
  • the C3-C20 can all be C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18 or C19, etc.
  • the C2-C12 can all be C3, C4, C5, C6, C7, C8, C9, C10 or C11, etc.
  • the C1-C10 can all be C1, C2, C3, C4, C5, C6, C7, C8, C9 or C10.
  • the C3-C10 can all be C3, C4, C5, C6, C7, C8, C9 or C10.
  • the C2-C10 can all be C2, C3, C4, C5, C6, C7, C8, C9 or C10.
  • the C1-C6 can all be C1, C2, C3, C4, C5 or C6; the C3-C6 can all be C3, C4, C5 or C6.
  • the C6-C30 aryl group preferably C6-C20 aryl group, includes a single-ring aryl group and a fused-ring aryl group;
  • the single-ring aryl group means that the group contains at least one phenyl group, when containing When there are at least two phenyl groups, the phenyl groups are connected by a single bond, exemplarily including but not limited to: phenyl, biphenyl, terphenyl, etc.
  • the condensed aromatic group means that the group contains at least 2 two aromatic rings, and two adjacent carbon atoms are fused together between the aromatic rings, examples include but not limited to: naphthyl, anthracenyl, phenanthrenyl, indenyl, fluorenyl and derivatives thereof (9,9-Dimethylfluorenyl, 9,9-diethylfluorenyl, 9,9-dipropylfluorenyl, 9,9-dibutylfluoren
  • the C3-C30 heteroaryl includes monocyclic heteroaryl and condensed ring heteroaryl.
  • the monocyclic heteroaryl group means that the molecule contains at least one heteroaryl group.
  • the heteroaryl group and other The groups are connected by a single bond, exemplarily including but not limited to: furyl, thienyl, pyrrolyl, pyridyl and the like.
  • the fused-ring heteroaryl group means a group that contains at least one aromatic heterocycle and one aromatic ring (aromatic heterocycle or aromatic ring) in the molecule, and the two share two adjacent atoms that are fused to each other.
  • Exemplary Including but not limited to: benzofuryl, benzothienyl, isobenzofuryl, isobenzothienyl, indolyl, dibenzofuryl, dibenzothienyl, carbazolyl and derivatives thereof (for example, the carbazolyl and its derivatives can be N-phenylcarbazolyl, N-naphthylcarbazolyl, benzocarbazolyl, dibenzocarbazolyl, indolocarbazolyl , azacarbazolyl, etc.), acridinyl, phenothiazinyl, phenoxazinyl, hydrogenated acridinyl, etc.
  • arylene group described below in the present application may include divalent groups obtained by removing one hydrogen atom from the above-mentioned aryl group; specific examples of the heteroarylene group may include the above-mentioned heteroaryl group The divalent group obtained by removing a hydrogen atom in the example.
  • the C1-C20 straight-chain or branched-chain alkyl exemplary includes but not limited to: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl , isopentyl, neopentyl, n-hexyl, n-octyl, n-heptyl, n-nonyl, n-decyl, etc.
  • the C3-C20 cycloalkyl group exemplarily includes, but is not limited to: cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl and the like.
  • the Ar 1 and Ar 2 are each independently selected from any one of substituted or unsubstituted C6-C20 aryl groups, substituted or unsubstituted C10-C20 fused ring heteroaryl groups.
  • the Ar 1 and Ar 2 are each independently selected from any of the following substituted or unsubstituted groups:
  • * represents the connection site of the group
  • Z is selected from any one of O, S, CR 11 R 12 , NR 13 or SiR 14 R 15 ;
  • R 11 , R 12 , R 13 , R 14 , and R 15 are each independently selected from hydrogen, substituted or unsubstituted C1-C20 linear or branched chain alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted Or unsubstituted C2-C12 alkenyl, substituted or unsubstituted C2-C12 alkynyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl.
  • R 11 and R 12 are not connected or are connected to form a ring through a chemical bond
  • R 14 and R 15 are not connected or are connected to form a ring through a chemical bond.
  • the R 11 , R 12 , R 13 , R 14 , and R 15 are each independently methyl or phenyl; R 11 and R 12 are not connected or connected to form a ring through a chemical bond (a fluorene ring), and R 14 and R 15 are not connected or connected by a chemical bond to form a ring.
  • the Ar is selected from any one of the substituted or unsubstituted following groups:
  • * represents the linking site of the group.
  • the Ar is selected from any one of the following substituted or unsubstituted groups : Among them, * represents the linking site of the group.
  • the Ar 1 and Ar 2 are not simultaneously phenyl.
  • the Ar3 is substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, and the substituted substituent is selected from halogen, C1-C6 straight chain or branched chain alkyl, C3-C6 ring At least one of alkyl, C1-C6 alkoxy or C1-C6 alkylthio.
  • the Ar 3 is biphenyl or phenyl, more preferably phenyl.
  • the X is CR 1 R 2 , NR 3 or SiR 4 R 5 , more preferably CR 1 R 2 .
  • the R 1 , R 2 , R 3 , R 4 , and R 5 are each independently selected from substituted or unsubstituted C1-C6 straight chain or branched chain alkyl, substituted or unsubstituted C6-C18 aryl , any of substituted or unsubstituted C3-C18 heteroaryl groups.
  • the R 1 , R 2 , R 3 , R 4 , and R 5 are each independently methyl or phenyl; the R 1 and R 2 are not connected or connected to form a fluorene ring through a chemical bond, and the R 4 and R 5 are not connected or connected by a chemical bond to form a ring.
  • the R f1 , R f2 , and R f3 are each independently selected from halogen, cyano, substituted or unsubstituted C1-C6 linear or branched chain alkyl, substituted or unsubstituted C3-C6 cycloalkyl , substituted or unsubstituted C6-C18 aryl, substituted or unsubstituted C3-C18 heteroaryl.
  • the k 1 , k 2 and k 3 are all 0.
  • the substituting groups are each independently selected from halogen, C1-C10 straight chain or branched chain alkyl, C3-C10 cycloalkyl, C2-C10 heterocycloalkyl, C1-C10 alkoxy, C1-C10 alkylthio , at least one of C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 aryl or C3-C30 heteroaryl, more preferably halogen, C1-C10 straight chain or branched chain alkyl, At least one of C3-C10 cycloalkyl, C2-C10 heterocycloalkyl, C6-C30 aryl or C3
  • the substituent group in Ar 3 is at least one selected from halogen, C1-C6 linear or branched chain alkyl, C3-C6 cycloalkyl, C1-C6 alkoxy or C1-C6 alkylthio.
  • the organic compound has the structure shown in any one of the following P1-P496:
  • the above-mentioned organic compound when the above-mentioned organic compound is selected from any one or more of the above-mentioned P9, P49, P237, P245, P250, P251, P252, P269, P309, P393 or P394, its application Used as an electron blocking layer material and/or a hole transporting layer material in an organic electroluminescent device, it can more effectively improve the luminous efficiency of the device and reduce the driving voltage.
  • the second purpose of the present application is to provide an application of the organic compound described in the first purpose, and the organic compound is applied to an organic electroluminescent device.
  • the organic compound acts as an electron blocking material and/or a hole transporting material in an organic electroluminescent device.
  • organic compounds of the present application can also be applied to lighting elements, organic thin film transistors, organic field effect transistors, organic thin film solar cells, information labels, electronic artificial skin sheets, sheet type scanners or electronic paper .
  • the third object of the present application is to provide an organic electroluminescence device, which comprises a first electrode, a second electrode and at least one organic layer arranged between the first electrode and the second electrode ;
  • the organic layer includes at least one organic compound as described in one of the purposes.
  • the organic layer includes an electron blocking layer
  • the electron blocking layer includes at least one organic compound as described in one of the purposes.
  • the organic compound provided by the application is applied to organic electroluminescent devices, and it is used as an electron blocking layer material, especially as a green photoelectron blocking layer material, which can improve the luminous efficiency of the device, reduce the driving voltage, and make the device have better performance.
  • the organic layer includes a hole transport layer
  • the hole transport layer includes at least one organic compound as described in one of the purposes.
  • the organic electroluminescent device includes a first electrode and a second electrode, and an organic layer located between the first electrode and the second electrode.
  • the organic layer can be further divided into multiple regions, for example including a hole transport region, a light emitting layer, and an electron transport region.
  • a substrate may be used either below the first electrode or above the second electrode.
  • the substrates are all glass or polymer materials with excellent mechanical strength, thermal stability, water resistance and transparency.
  • a thin-film transistor (TFT) may be provided on a substrate for a display.
  • the first electrode may be formed by sputtering or depositing a material used as the first electrode on the substrate.
  • oxide transparent conductive materials such as indium tin oxide (ITO), indium zinc oxide (IZO), tin dioxide (SnO 2 ), zinc oxide (ZnO) and any combination thereof can be used.
  • magnesium (Mg) silver (Ag), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), ytterbium (Yb), magnesium-indium (Mg-In ), magnesium-silver (Mg-Ag) and other metals or alloys and any combination thereof.
  • the organic layer can be formed on the electrode by vacuum thermal evaporation, spin coating, printing and other methods.
  • Compounds used as organic layers can be small organic molecules, organic macromolecules or polymers, and combinations thereof.
  • the hole transport region is located between the anode and the light emitting layer.
  • the hole transport region can be a hole transport layer (HTL) with a single-layer structure, including a single-layer hole-transport layer containing only one compound and a single-layer hole-transport layer containing multiple compounds.
  • HTL hole transport layer
  • the hole transport region can also be a multilayer structure comprising at least one of a hole injection layer (HIL), a hole transport layer (HTL), and an electron blocking layer (EBL); wherein the HIL is positioned between the anode and the HTL, and the EBL It is located between the HTL and the light-emitting layer; the HTL and/or the EBL contain at least one organic compound with the structure of formula I, preferably the EBL contains at least one organic compound with the structure of formula I.
  • HIL hole injection layer
  • HTL hole transport layer
  • EBL electron blocking layer
  • the material of the hole transport region can also be selected from, but not limited to, phthalocyanine derivatives such as CuPc, conductive polymers or polymers containing conductive dopants such as polyphenylene vinylene, polyaniline/dodecylbenzenesulfonic acid ( Pani/DBSA), poly(3,4-ethylenedioxythiophene)/poly(4-styrenesulfonate) (PEDOT/PSS), polyaniline/camphorsulfonic acid (Pani/CSA), polyaniline/poly (4-styrene sulfonate) (Pani/PSS), aromatic amine derivatives, wherein the aromatic amine derivatives include the following compounds shown in HT-1 to HT-51; or any combination thereof.
  • a hole injection layer is located between the anode and the hole transport layer.
  • the hole injection layer can be a single compound material, or a combination of multiple compounds.
  • the hole injection layer can use one or more compounds of the above-mentioned HT-1 to HT-51, or one or more compounds in the following HI-1 to HI-3; HT-1 can also be used
  • One or more compounds to HT-51 are doped with one or more compounds from HI-1 to HI-3 described below.
  • the luminescent layer includes luminescent dyes (that is, dopant) that can emit different wavelength spectra, and can also include a host material (Host) at the same time.
  • the light-emitting layer may be a monochromatic light-emitting layer that emits a single color such as red, green, or blue.
  • a plurality of monochromatic light emitting layers of different colors can be arranged in a plane according to the pixel pattern, and can also be stacked together to form a colored light emitting layer. When the light-emitting layers of different colors are stacked together, they can be separated from each other or connected to each other.
  • the light-emitting layer can also be a single color light-emitting layer capable of simultaneously emitting different colors such as red, green, and blue.
  • different materials such as fluorescent electroluminescent materials, phosphorescent electroluminescent materials, and heat-activated delayed fluorescent luminescent materials can be used as materials for the light-emitting layer.
  • a single light-emitting technology can be used, or a combination of multiple different light-emitting technologies can be used.
  • These different luminescent materials classified by technology can emit light of the same color or of different colors.
  • the light-emitting layer adopts fluorescence electroluminescence technology.
  • the fluorescent host material of the light-emitting layer can be selected from, but not limited to, one or more combinations of BFH-1 to BFH-17 listed below.
  • the light-emitting layer adopts fluorescence electroluminescence technology.
  • the fluorescent dopant in the light-emitting layer can be selected from, but not limited to, one or more combinations of BFD-1 to BFD-24 listed below.
  • the light-emitting layer adopts phosphorescence electroluminescence technology.
  • the host material of the light-emitting layer is selected from, but not limited to, one or more combinations of PH-1 to PH-85.
  • the light-emitting layer adopts phosphorescence electroluminescence technology.
  • the phosphorescent dopant in the light-emitting layer can be selected from, but not limited to, one or more combinations of GPD-1 to GPD-47 listed below.
  • the light-emitting layer adopts phosphorescence electroluminescence technology.
  • the phosphorescent dopant in the light-emitting layer can be selected from, but not limited to, one or more combinations of RPD-1 to RPD-28 listed below.
  • the light-emitting layer adopts phosphorescence electroluminescence technology.
  • the phosphorescent dopant in the light-emitting layer can be selected from, but not limited to, one or more combinations of YPD-1 to YPD-11 listed below.
  • the OLED organic layers may also include an electron transport region between the light emitting layer and the cathode.
  • the electron transport region may be a single-layer electron transport layer (ETL), including a single-layer electron-transport layer containing only one compound and a single-layer electron-transport layer containing multiple compounds.
  • the electron transport region may also be a multilayer structure including at least one of an electron injection layer (EIL), an electron transport layer (ETL), and a hole blocking layer (HBL).
  • EIL electron injection layer
  • ETL electron transport layer
  • HBL hole blocking layer
  • the electron transport layer material may be selected from, but not limited to, one or more combinations of ET-1 to ET-73 listed below.
  • a hole blocking layer is located between the electron transport layer and the light emitting layer.
  • Hole blocking layer can adopt, but not limited to, one or more compounds of above-mentioned ET-1 to ET-73, or adopt, but not limited to one or more compounds in PH-1 to PH-46; Mixtures of one or more compounds from ET-1 to ET-73 and one or more compounds from PH-1 to PH-46 are used, but are not limited to.
  • the device may also include an electron injection layer located between the electron transport layer and the cathode, and the materials of the electron injection layer include but are not limited to one or more combinations of the following: LiQ, LiF, NaCl, CsF, Li 2 O, Cs 2 CO 3 , BaO, Na, Li, Ca, Mg or Yb.
  • the thicknesses of the above hole injection layer, hole transport layer, electron blocking layer, light emitting layer, hole blocking layer, electron transport layer and electron injection layer are not limited.
  • the thickness of the hole injection layer is preferably 8 to 12 nm
  • the thickness of the hole transport layer is preferably 55 to 65 nm
  • the thickness of the electron blocking layer is preferably 30 to 40 nm.
  • the thickness of the light-emitting layer is 35-45 nm
  • the thickness of the hole blocking layer is preferably 3-8 nm
  • the thickness of the electron transport layer is preferably 20-30 nm
  • the thickness of the electron injection layer is preferably 0.8-1.2 nm.
  • the thickness of the hole injection layer is 10nm
  • the thickness of the hole transport layer is 60nm
  • the thickness of the electron blocking layer is 35nm
  • the thickness of the light-emitting layer is 40nm
  • the thickness of the hole blocking layer is 5nm
  • the thickness of the electron transport layer is When the thickness of the electron injection layer is 25nm and the thickness of the electron injection layer is 1nm, the obtained electroluminescent device has more excellent luminous efficiency and lower driving voltage.
  • the organic compound provided by this application has a structure as shown in formula I.
  • the organic compound has better stability and photoelectric properties through the design of molecular structure, which can improve and balance carrier transport and improve device performance; at the same time, the The molecular weight of the above-mentioned organic compound is suitable, and the evaporation temperature is relatively low, which is beneficial to the industrial production of organic electroluminescent devices.
  • the organic compound is used as an electron blocking layer material of an organic electroluminescent device, which can reduce the driving voltage of the device, improve luminous efficiency, and make the OLED device have better comprehensive performance.
  • the preparation method of the organic compound is simple, the raw materials are readily available, and it is easy to realize large-scale mass production.
  • Ar 1 , Ar 2 , Ar 3 , X, R f1 , R f2 , R f3 , k 1 , k 2 , and k 3 have the same meanings as in formula I;
  • Pd(PPh 3 ) 4 represents tetrakistriphenyl Palladium phosphine
  • Pd 2 (dba) 3 represents tris(dibenzylacetone) dipalladium (0)
  • Sphos represents 2-bicyclohexylphosphine-2′,6′-dimethoxybiphenyl
  • IPr.HCl represents 1 , 3-bis(2,6-diisopropylphenyl) imidazolium chloride
  • NaOBu-t represents sodium tert-butoxide
  • (t-Bu) 3 P represents tri-tert-butylphosphine.
  • the preparation of the organic compound described in the present application includes, but is not limited to, the above-mentioned method.
  • the organic compound represented by formula I synthesized by those skilled in the art by other methods also belongs to the protection scope of the present application.
  • synthesis examples in this application exemplarily provide the specific synthesis methods of the organic compounds.
  • the solvents and reagents used in the following synthesis examples can be purchased or customized from the chemical product market.
  • those skilled in the art can also synthesize by other known methods.
  • the mass spectrometric characterization data in the following synthesis examples were obtained by testing with a ZAB-HS mass spectrometer manufactured by Micromass, UK.
  • M1-1 m/z theoretical value: 309; m/z measured value: 310.
  • M1-2 m/z theoretical value: 351; m/z measured value: 352.
  • M1-3 m/z theoretical value: 321; m/z measured value: 322.
  • M1-4 m/z theoretical value: 513; m/z measured value: 514.
  • a kind of organic electroluminescence device comprises anode (ITO), hole injection layer, hole transport layer, electron blocking layer, light-emitting layer, hole blocking layer, electron transport layer, electron injection layer and negative electrode (Al ).
  • ITO anode
  • hole injection layer hole transport layer
  • electron blocking layer hole blocking layer
  • light-emitting layer hole blocking layer
  • electron transport layer electron injection layer
  • negative electrode Al
  • the preparation method of the organic electroluminescent device is as follows: the glass plate coated with the ITO transparent conductive layer is ultrasonically treated in a commercial cleaning agent, rinsed in deionized water, and ultrasonically degreased in a mixed solvent of acetone/ethanol.
  • An organic electroluminescent device the only difference from Example 1 is that the electronic blocking layer material organic compound P9 is replaced by P49, P237, P245, P250, P251, P252, P269, P309, P393, P394.
  • An organic electroluminescent device the only difference from Example 1 is that the electron blocking layer material organic compound P9 is replaced by CCP-1, CCP-2, CCP-3, CCP-4, CCP-5.
  • the organic compound provided by the present application is applied to an organic electroluminescent device, which can make the driving voltage of the device under the brightness of 10000cd/m 2 be 4.0-4.2V, and the current efficiency is 66.4-68.1cd/A, Therefore, the driving voltage can be effectively reduced, the current efficiency can be improved, and it is a green photoelectron blocking layer material with good performance.
  • the difference between the electron blocking layer material CCP-1 in Comparative Example 1 and P237 in Example 2 is that the fluorenyl group in CCP-1 is connected to the N atom through a phenylene group, which reduces the mobility of CCP-1.
  • the molecular packing density is poor, which affects the luminous efficiency and driving voltage of the device; in the electron blocking layer materials in Comparative Examples 2-4, the N atoms of the arylamine are connected to the 1-position, 3-position, and 4-position of the fluorenyl group respectively , compared with the 2-position where the N atom is connected to the fluorenyl group, the mobility is lower, which is not conducive to the transmission of excitons, so the device performance is poor; the N-ortho position of the arylamine in Comparative Example 5 has no substituents connected, so that the molecular The LUMO energy level is deep, which reduces the luminescent performance of the device.

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Abstract

An organic compound and an application thereof. The organic compound has a structure represented by formula I, has better stability and photoelectric properties, and can enhance and balance carrier transport, thereby improving device performance. The organic compound is used as an electron blocking layer material of an organic light-emitting diode (OLED) device, and can reduce the driving voltage of the device and improve the luminous efficiency, so that the OLED device has better comprehensive performance. In addition, according to the organic compound, the preparation method is simple, the raw materials are easily available, and large-scale mass production is easy to be realized.

Description

一种有机化合物及其应用A kind of organic compound and its application
相关申请的交叉引用Cross References to Related Applications
本申请要求在2021年06月28日提交中国专利局、申请号为202110719937.4、申请名称为“一种有机化合物及其应用”的中国专利申请的优先权，其全部内容通过引用结合在本申请中。This application claims the priority of the Chinese patent application with the application number 202110719937.4 and the application title "An Organic Compound and Its Application" submitted to the China Patent Office on June 28, 2021, the entire contents of which are incorporated by reference in this application .
技术领域technical field
本申请属于有机电致发光材料技术领域，具体涉及一种有机化合物及其应用。The application belongs to the technical field of organic electroluminescent materials, and specifically relates to an organic compound and its application.
背景技术Background technique
有机电致发光(Organic Light Emission Diodes，OLED)器件是近年来新兴的显示技术，具有亮度高、响应快、能耗低、视角宽、可柔性化、温度适应范围大、工艺简单等特点，已被广泛应用于照明灯具、智能手机及平板电脑等产品的显示面板中，并进一步向电视等大尺寸显示产品应用领域扩展。Organic Light Emission Diodes (OLED) devices are emerging display technologies in recent years. They have the characteristics of high brightness, fast response, low energy consumption, wide viewing angle, flexibility, wide temperature range, and simple process. It is widely used in the display panels of products such as lighting fixtures, smart phones and tablet computers, and further expands to the application fields of large-size display products such as TVs.
OLED器件具有类三明治结构，包括正负电极及夹在两个电极之间的有机功能材料层；对OLED器件的电极施加电压时，电子和空穴被分别注入、传输到发光区域并在此复合，从而产生激子并发光。OLED器件的核心为有机功能材料层，构成该材料层的常见有机功能材料包括：空穴注入材料、空穴传输材料、空穴阻挡材料、电子注入材料、电子传输材料、电子阻挡材料以及发光主体材料和发光客体(染料)等。The OLED device has a sandwich-like structure, including positive and negative electrodes and an organic functional material layer sandwiched between the two electrodes; when a voltage is applied to the electrodes of the OLED device, electrons and holes are respectively injected, transported to the light-emitting region and recombined there , thereby generating excitons and emitting light. The core of an OLED device is an organic functional material layer. The common organic functional materials that make up the material layer include: hole injection materials, hole transport materials, hole blocking materials, electron injection materials, electron transport materials, electron blocking materials, and light-emitting hosts. Materials and luminescent guests (dye), etc.
常见的荧光发光体主要利用电子和空穴结合时产生的单线态激子发光，现在仍然广泛地应用于各种OLED产品中。有些金属络合物(例如铱络合物)可以同时利用三线态激子和单线态激子进行发光，被称为磷光发光体，其能量转换效率可以比传统的荧光发光体提升高达四倍。热激发延迟荧光(TADF)技术通过促进三线态激子向单线态激子的转变，在不采用金属配合物的情况下，仍然可以有效地利用三线态激子而实现较高的发光效率。热激发敏化荧光(TASF)技术则采用具TADF性质的材料，通过能量转移的方式来敏化发光体，同样可以实现较高的发光效率。Common fluorescent emitters mainly use singlet excitons generated when electrons and holes combine to emit light, and are still widely used in various OLED products. Some metal complexes (such as iridium complexes) can simultaneously utilize triplet excitons and singlet excitons to emit light, which are called phosphorescent emitters, and their energy conversion efficiency can be up to four times higher than that of traditional fluorescent emitters. Thermally Excited Delayed Fluorescence (TADF) technology promotes the transformation of triplet excitons to singlet excitons, and can still effectively utilize triplet excitons to achieve high luminous efficiency without using metal complexes. Thermally-stimulated sensitized fluorescence (TASF) technology uses materials with TADF properties to sensitize light emitters through energy transfer, and can also achieve higher luminous efficiency.
空穴传输材料对器件的性能有着显著影响，一方面，空穴传输材料需要有适合的HOMO能级，空穴材料与阳极间的合适的能隙，利于空穴的注入，可帮助降低工作电压；另一方面，空穴传输材料调控器件内载流子的传输平衡，提升空穴传输材料的载流子迁移率，从而提高发光效率、延缓器件衰减。虽然目前采用OLED显示技术的产品已经商品化，但是对器件的效率、使用寿命等方面还有进一步提升的要求。The hole transport material has a significant impact on the performance of the device. On the one hand, the hole transport material needs to have a suitable HOMO energy level, and a suitable energy gap between the hole material and the anode is conducive to the injection of holes and can help reduce the operating voltage. On the other hand, the hole transport material regulates the transport balance of carriers in the device and improves the carrier mobility of the hole transport material, thereby improving the luminous efficiency and delaying the decay of the device. Although products using OLED display technology have been commercialized, there are still requirements for further improvement in terms of device efficiency and service life.
因此，本领域亟待开发更多种类、更高性能的有机材料，以改善有机电致发光器件的性能，使器件具有更高的发光效率和更低的驱动电压。Therefore, there is an urgent need to develop more types of organic materials with higher performance in this field to improve the performance of organic electroluminescent devices, so that the devices have higher luminous efficiency and lower driving voltage.
发明内容Contents of the invention
针对现有技术的不足，本申请的目的在于提供一种有机化合物及其应用，所述有机化合物应用于有机电致发光器件，尤其适于作为电子阻挡层材料和/或空穴传输层材料，可以提升器件的发光效率，降低驱动电压。In view of the deficiencies in the prior art, the purpose of this application is to provide an organic compound and its application. The organic compound is applied to an organic electroluminescent device, and is especially suitable as an electron blocking layer material and/or a hole transporting layer material, The luminous efficiency of the device can be improved and the driving voltage can be reduced.
为达此目的，本申请采用以下技术方案：For this purpose, the application adopts the following technical solutions:
本申请的目的之一提供一种有机化合物，所述有机化合物具有如式I所示结构：One of the purposes of the present application provides a kind of organic compound, and described organic compound has structure as shown in formula I:
Figure PCTCN2022100562-appb-000001
Figure PCTCN2022100562-appb-000001
式I中，Ar 1、Ar 2各自独立地选自取代或未取代的C6-C30芳基、取代或未取代的C3-C30杂芳基中的任意一种。 In formula I, Ar 1 and Ar 2 are each independently selected from any one of substituted or unsubstituted C6-C30 aryl groups and substituted or unsubstituted C3-C30 heteroaryl groups.
式I中，Ar 3选自取代或未取代的C6-C12芳基、取代或未取代的C3-C11杂芳基中的任意一种。 In formula I, Ar 3 is selected from any one of substituted or unsubstituted C6-C12 aryl, substituted or unsubstituted C3-C11 heteroaryl.
式I中，X选自O、S、CR 1R 2、NR 3或SiR 4R 5中的任意一种。 In formula I, X is selected from any one of O, S, CR 1 R 2 , NR 3 or SiR 4 R 5 .
R 1、R 2、R 3、R 4、R 5各自独立地选自氢、取代或未取代的C1-C20直链或支链烷基、取代或未取代的C3-C20环烷基、取代或未取代的C2-C12烯基、取代或未取代的C2-C12炔基、取代或未取代的C6-C30芳基、取代或未取代的C3-C30杂芳基中的任意一种； R 1 , R 2 , R 3 , R 4 , and R 5 are each independently selected from hydrogen, substituted or unsubstituted C1-C20 linear or branched chain alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted Or any of unsubstituted C2-C12 alkenyl, substituted or unsubstituted C2-C12 alkynyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl;
R 1和R 2不连接或通过化学键连接成环，R 4和R 5不连接或通过化学键连接成环； R 1 and R 2 are not connected or are connected to form a ring by a chemical bond, R 4 and R 5 are not connected or are connected to form a ring by a chemical bond;
R f1、R f2、R f3各自独立地选自卤素、氰基、取代或未取代的C1-C20直链或支链烷基、取代或未取代的C3-C20环烷基、取代或未取代的C2-C12烯基、取代或未取代的C2-C12炔基、取代或未取代的C6-C30芳基、取代或未取代的C3-C30杂芳基中的任意一种； R f1 , R f2 , and R f3 are each independently selected from halogen, cyano, substituted or unsubstituted C1-C20 linear or branched chain alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted Any one of C2-C12 alkenyl, substituted or unsubstituted C2-C12 alkynyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl;
Ar 1、Ar 2、R 1、R 2、R 3、R 4、R 5、R f1、R f2、R f3中所述取代的取代基各自独立地选自卤素、C1-C10直链或支链烷基、C3-C10环烷基、C2-C10杂环烷基、C1-C10烷氧基、C1-C10烷硫基、C6-C30芳基氨基、C3-C30杂芳基氨基、C6-C30芳基或C3-C30杂芳基中的至少一种； Ar 1 , Ar 2 , R 1 , R 2 , R 3 , R 4 , R 5 , R f1 , R f2 , and R f3 are each independently selected from halogen, C1-C10 straight chain or branched Alkanyl, C3-C10 cycloalkyl, C2-C10 heterocycloalkyl, C1-C10 alkoxy, C1-C10 alkylthio, C6-C30 arylamino, C3-C30 heteroarylamino, C6- At least one of C30 aryl or C3-C30 heteroaryl;
Ar 3中所述取代的取代基选自卤素、C1-C6直链或支链烷基、C3-C6环烷基、C1-C6烷氧基或C1-C6烷硫基中的至少一种。 The substituted substituent in Ar 3 is at least one selected from halogen, C1-C6 linear or branched chain alkyl, C3-C6 cycloalkyl, C1-C6 alkoxy or C1-C6 alkylthio.
k 1、k 2各自独立地为0-3的整数，例如可以为0、1、2或3；k 3为0-4的整数，例如可以为0、1、2、3或4。 k 1 and k 2 are each independently an integer of 0-3, such as 0, 1, 2 or 3; k 3 is an integer of 0-4, such as 0, 1, 2, 3 or 4.
本申请提供的有机化合物具有如式I所示结构，通过分子结构的设计，芳胺N与二苯并五元环稠合结构直接相连，有利于迁移率的提升，且分子堆积更致密；且N与二苯并五元环稠合结构的2-位相连，可以使器件迁移率进一步提升、性能变好；N与Ar 1、Ar 2分别位于苯环相邻的位置，这可以使LUMO能级变浅，从而进一步阻挡激子向空穴层扩散，使器件性能提高；同时，所述Ar 3选自分子量较小的C6-C12芳基或C3-C11杂芳基，有利于化合物整体分子量的调控，从而避免因分子量过大而导致在器件制备过程中的蒸镀温度过高，更有利于生产。所述有机化合物用于有机电致发光器件中，其作为电子阻挡层材料和/或空穴传输层材料，能有效降低器件的驱动电压，提高发光效率。 The organic compound provided by this application has a structure as shown in formula I. Through the design of the molecular structure, the arylamine N is directly connected to the condensed structure of the dibenzo five-membered ring, which is conducive to the improvement of the mobility, and the molecular packing is denser; and N is connected to the 2-position of the dibenzo five-membered ring fused structure, which can further improve the mobility and performance of the device; N, Ar 1 and Ar 2 are located adjacent to the benzene ring, which can make the LUMO energy The level becomes shallow, thereby further blocking the diffusion of excitons to the hole layer, and improving the performance of the device; at the same time, the Ar 3 is selected from C6-C12 aryl or C3-C11 heteroaryl with a smaller molecular weight, which is beneficial to the overall molecular weight of the compound Controlling, so as to avoid excessive evaporation temperature in the device preparation process due to excessive molecular weight, which is more conducive to production. The organic compound is used in an organic electroluminescent device, and as an electron blocking layer material and/or a hole transporting layer material, it can effectively reduce the driving voltage of the device and improve luminous efficiency.
需要说明的是，本申请中为了便于说明对各个基团/特征可能的作用分别进行了描述，但这并不表示这些基团/特征是孤立地起作用的。实际上，获得良好性能的原因本质上是整个分子的优化组合，是各个基团之间协同作用的结果，而不是单一基团的效果。It should be noted that, for the convenience of explanation, the possible functions of each group/feature are described separately in this application, but this does not mean that these groups/features function in isolation. In fact, the reason for obtaining good performance is essentially the optimized combination of the entire molecule, which is the result of the synergistic effect between the various groups, rather than the effect of a single group.
本申请中，所述卤素均可以为氟、氯、溴或碘。下文涉及到相同的描述，均具有相同的含义。In the present application, the halogens can all be fluorine, chlorine, bromine or iodine. The following descriptions refer to the same, and all have the same meaning.
本申请中，所述“取代或未取代”的基团，可以取代有一个取代基，也可以取代有多个取代基，当取代基为多个(至少2个)时，可以为相同或不同的取代基；下文涉及到相同 的表达方式时，均具有同样的含义，且取代基的选择范围均如上所示，不再赘述。In the present application, the "substituted or unsubstituted" group may be substituted with one substituent, or may be substituted with multiple substituents. When there are multiple substituents (at least 2), they may be the same or different Substituents; when the same expressions are mentioned below, they all have the same meaning, and the selection range of the substituents is as shown above, and will not be repeated.
本申请中，对于化学元素的表述，若无特别说明，则包含化学性质相同的同位素的概念，例如，氢(H)则包括 1H(氕)、 2H(氘，D)、 3H(氚，T)等；碳(C)则包括 12C、 13C等。 In this application, for the expression of chemical elements, unless otherwise specified, the concept of isotopes with the same chemical properties is included, for example, hydrogen (H) includes 1 H (protium), 2 H (deuterium, D), 3 H ( tritium, T), etc.; carbon (C) includes 12 C, 13 C, etc.
本申请中，如无特别说明，杂芳基的杂原子选自N、O、S、P、B、Si或Se。In the present application, unless otherwise specified, the heteroatoms of the heteroaryl group are selected from N, O, S, P, B, Si or Se.
本申请中，“—”划过的环结构的表达方式，表示连接位点于该环结构上任意能够成键的位置。In the present application, the expression of the ring structure crossed by "—" indicates that the linking site is at any position on the ring structure that can form a bond.
在本申请中，Ca-Cb的表达方式代表该基团具有的碳原子数为a-b，除非特殊说明，一般而言该碳原子数不包括取代基的碳原子数。In the present application, the expression of Ca-Cb means that the number of carbon atoms of the group is a-b, unless otherwise specified, generally speaking, the number of carbon atoms does not include the number of carbon atoms of the substituent.
在本说明书中，“各自独立地”表示其主语具有多个时，彼此之间可以相同也可以不同。In this specification, "each independently" means that when there are plural subjects, they may be the same or different from each other.
本申请中，所述C6-C30均可以为C6、C9、C10、C12、C14、C16、C18、C20、C22、C24、C26或C28等。In the present application, the C6-C30 can all be C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26 or C28, etc.
所述C3-C30均可以为C3、C4、C5、C6、C9、C10、C12、C14、C16、C18、C20、C22、C24、C26或C28等。The C3-C30 can all be C3, C4, C5, C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26 or C28, etc.
所述C6-C12均可以为C6、C9、C10或C12等；所述C3-C11均可以为C3、C4、C5、C6、C9或C10等。The C6-C12 can all be C6, C9, C10, or C12, etc.; the C3-C11 can all be C3, C4, C5, C6, C9, or C10, etc.
所述C1-C20均可以为C2、C3、C4、C5、C6、C7、C8、C9、C10、C11、C12、C13、C14、C15、C16、C17、C18或C19等。The C1-C20 can all be C2, C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18 or C19, etc.
所述C3-C20均可以为C4、C5、C6、C7、C8、C9、C10、C11、C12、C13、C14、C15、C16、C17、C18或C19等。The C3-C20 can all be C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18 or C19, etc.
所述C2-C12均可以为C3、C4、C5、C6、C7、C8、C9、C10或C11等。The C2-C12 can all be C3, C4, C5, C6, C7, C8, C9, C10 or C11, etc.
所述C1-C10均可以为C1、C2、C3、C4、C5、C6、C7、C8、C9或C10。The C1-C10 can all be C1, C2, C3, C4, C5, C6, C7, C8, C9 or C10.
所述C3-C10均可以为C3、C4、C5、C6、C7、C8、C9或C10。The C3-C10 can all be C3, C4, C5, C6, C7, C8, C9 or C10.
所述C2-C10均可以为C2、C3、C4、C5、C6、C7、C8、C9或C10。The C2-C10 can all be C2, C3, C4, C5, C6, C7, C8, C9 or C10.
所述C1-C6均可以为C1、C2、C3、C4、C5或C6；所述C3-C6均可以为C3、C4、C5或C6。The C1-C6 can all be C1, C2, C3, C4, C5 or C6; the C3-C6 can all be C3, C4, C5 or C6.
本申请中，所述C6-C30芳基，优选C6-C20芳基，包括单环芳基和稠环芳基；所述单环芳基意指基团中含有至少1个苯基，当含有至少2个苯基时，苯基之间通过单键相连，示例性地包括但不限于：苯基、联苯基、三联苯基等；所述稠环芳基意指基团中含有至少2个芳环，且芳环之间共用两个相邻的碳原子互相稠合的基团，示例性地包括但不限于：萘基、蒽基、菲基、茚基、芴基及其衍生物(9，9-二甲基芴基、9，9-二乙基芴基、9，9-二丙基芴基、9，9-二丁基芴基、9，9-二戊基芴基、9，9-二己基芴基、9，9-二苯基芴基、9，9-二萘基芴基、螺二芴基、苯并芴基等)、荧蒽基、三亚苯基、芘基、苝基、
Figure PCTCN2022100562-appb-000002
基或并四苯基等。 In the present application, the C6-C30 aryl group, preferably C6-C20 aryl group, includes a single-ring aryl group and a fused-ring aryl group; the single-ring aryl group means that the group contains at least one phenyl group, when containing When there are at least two phenyl groups, the phenyl groups are connected by a single bond, exemplarily including but not limited to: phenyl, biphenyl, terphenyl, etc.; the condensed aromatic group means that the group contains at least 2 two aromatic rings, and two adjacent carbon atoms are fused together between the aromatic rings, examples include but not limited to: naphthyl, anthracenyl, phenanthrenyl, indenyl, fluorenyl and derivatives thereof (9,9-Dimethylfluorenyl, 9,9-diethylfluorenyl, 9,9-dipropylfluorenyl, 9,9-dibutylfluorenyl, 9,9-dipentylfluorenyl , 9,9-dihexylfluorenyl, 9,9-diphenylfluorenyl, 9,9-dinaphthylfluorenyl, spirobifluorenyl, benzofluorenyl, etc.), fluoranthenyl, triphenylene, pyrenyl, perylene,
Figure PCTCN2022100562-appb-000002
base or naphthacene, etc.
所述C3-C30杂芳基，包括单环杂芳基和稠环杂芳基。所述单环杂芳基意指分子中含有至少一个杂芳基，当分子中含有一个杂芳基和其他基团(如芳基、杂芳基、烷基等)时，杂芳基和其他基团之间通过单键进行连接，示例性地包括但不限于：呋喃基、噻吩基、吡咯基、吡啶基等。所述稠环杂芳基意指分子中至少含有一个芳杂环和一个芳香性环(芳杂环或芳环)，且二者共用两个相邻的原子互相稠合的基团，示例性地包括但不限于：苯并呋喃基、苯并噻吩基、异苯并呋喃基、异苯并噻吩基、吲哚基、二苯并呋喃基、二苯并噻吩基、咔唑基及其衍生物(例如，所述咔唑基及其衍生物可以为N-苯基咔唑基、N-萘基咔唑基、苯并咔唑基、二苯并咔唑基、吲哚并咔唑基、氮杂咔唑基等)、吖啶基、吩噻嗪基、吩恶嗪基、氢化吖啶基等。The C3-C30 heteroaryl includes monocyclic heteroaryl and condensed ring heteroaryl. The monocyclic heteroaryl group means that the molecule contains at least one heteroaryl group. When the molecule contains a heteroaryl group and other groups (such as aryl, heteroaryl, alkyl, etc.), the heteroaryl group and other The groups are connected by a single bond, exemplarily including but not limited to: furyl, thienyl, pyrrolyl, pyridyl and the like. The fused-ring heteroaryl group means a group that contains at least one aromatic heterocycle and one aromatic ring (aromatic heterocycle or aromatic ring) in the molecule, and the two share two adjacent atoms that are fused to each other. Exemplary Including but not limited to: benzofuryl, benzothienyl, isobenzofuryl, isobenzothienyl, indolyl, dibenzofuryl, dibenzothienyl, carbazolyl and derivatives thereof (for example, the carbazolyl and its derivatives can be N-phenylcarbazolyl, N-naphthylcarbazolyl, benzocarbazolyl, dibenzocarbazolyl, indolocarbazolyl , azacarbazolyl, etc.), acridinyl, phenothiazinyl, phenoxazinyl, hydrogenated acridinyl, etc.
本申请下文所述亚芳基的具体例，可以举出上述芳基的例子中去掉一个氢原子而得到 的二价基团；所述亚杂芳基的具体例，可以举出上述杂芳基的例子中去掉一个氢原子而得到的二价基团。Specific examples of the arylene group described below in the present application may include divalent groups obtained by removing one hydrogen atom from the above-mentioned aryl group; specific examples of the heteroarylene group may include the above-mentioned heteroaryl group The divalent group obtained by removing a hydrogen atom in the example.
所述C1-C20直链或支链烷基，示例性地包括但不限于：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、正辛基、正庚基、正壬基、正癸基等。The C1-C20 straight-chain or branched-chain alkyl, exemplary includes but not limited to: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl , isopentyl, neopentyl, n-hexyl, n-octyl, n-heptyl, n-nonyl, n-decyl, etc.
所述C3-C20环烷基，示例性地包括但不限于：环丙基、环丁基、环戊基、环己基、金刚烷基等。The C3-C20 cycloalkyl group exemplarily includes, but is not limited to: cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl and the like.
优选地，所述Ar 1、Ar 2各自独立地选自取代或未取代的C6-C20芳基、取代或未取代的C10-C20稠环杂芳基中的任意一种。 Preferably, the Ar 1 and Ar 2 are each independently selected from any one of substituted or unsubstituted C6-C20 aryl groups, substituted or unsubstituted C10-C20 fused ring heteroaryl groups.
优选地，所述Ar 1、Ar 2各自独立地选自取代或未取代的如下基团中的任意一种： Preferably, the Ar 1 and Ar 2 are each independently selected from any of the following substituted or unsubstituted groups:
Figure PCTCN2022100562-appb-000003
Figure PCTCN2022100562-appb-000003
其中，*代表基团的连接位点；Wherein, * represents the connection site of the group;
Z选自O、S、CR 11R 12、NR 13或SiR 14R 15中的任意一种； Z is selected from any one of O, S, CR 11 R 12 , NR 13 or SiR 14 R 15 ;
R 11、R 12、R 13、R 14、R 15各自独立地选自氢、取代或未取代的C1-C20直链或支链烷基、取代或未取代的C3-C20环烷基、取代或未取代的C2-C12烯基、取代或未取代的C2-C12炔基、取代或未取代的C6-C30芳基、取代或未取代的C3-C30杂芳基中的任意一种。 R 11 , R 12 , R 13 , R 14 , and R 15 are each independently selected from hydrogen, substituted or unsubstituted C1-C20 linear or branched chain alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted Or unsubstituted C2-C12 alkenyl, substituted or unsubstituted C2-C12 alkynyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl.
R 11和R 12不连接或通过化学键连接成环，R 14和R 15不连接或通过化学键连接成环。 R 11 and R 12 are not connected or are connected to form a ring through a chemical bond, and R 14 and R 15 are not connected or are connected to form a ring through a chemical bond.
优选地，所述R 11、R 12、R 13、R 14、R 15各自独立地为甲基或苯基；R 11和R 12不连接或通过化学键连接成环(成芴环)，R 14和R 15不连接或通过化学键连接成环。 Preferably, the R 11 , R 12 , R 13 , R 14 , and R 15 are each independently methyl or phenyl; R 11 and R 12 are not connected or connected to form a ring through a chemical bond (a fluorene ring), and R 14 and R 15 are not connected or connected by a chemical bond to form a ring.
优选地，所述Ar 1选自取代或未取代的如下基团中的任意一种： Preferably, the Ar is selected from any one of the substituted or unsubstituted following groups:
Figure PCTCN2022100562-appb-000004
Figure PCTCN2022100562-appb-000004
Figure PCTCN2022100562-appb-000005
Figure PCTCN2022100562-appb-000005
其中，*代表基团的连接位点。Among them, * represents the linking site of the group.
优选地，所述Ar 2选自取代或未取代的如下基团中的任意一种：
Figure PCTCN2022100562-appb-000006
Figure PCTCN2022100562-appb-000007
其中，*代表基团的连接位点。 Preferably, the Ar is selected from any one of the following substituted or unsubstituted groups :
Figure PCTCN2022100562-appb-000006
Figure PCTCN2022100562-appb-000007
Among them, * represents the linking site of the group.
优选地，所述Ar 1和Ar 2不同时为苯基。 Preferably, the Ar 1 and Ar 2 are not simultaneously phenyl.
优选地，所述Ar 3为取代或未取代的苯基、取代或未取代的联苯基，所述取代的取代基选自卤素、C1-C6直链或支链烷基、C3-C6环烷基、C1-C6烷氧基或C1-C6烷硫基中的至少一种。 Preferably, the Ar3 is substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, and the substituted substituent is selected from halogen, C1-C6 straight chain or branched chain alkyl, C3-C6 ring At least one of alkyl, C1-C6 alkoxy or C1-C6 alkylthio.
优选地，所述Ar 3为联苯基或苯基，进一步优选为苯基。 Preferably, the Ar 3 is biphenyl or phenyl, more preferably phenyl.
优选地，所述X为CR 1R 2、NR 3或SiR 4R 5，进一步优选为CR 1R 2。 Preferably, the X is CR 1 R 2 , NR 3 or SiR 4 R 5 , more preferably CR 1 R 2 .
优选地，所述R 1、R 2、R 3、R 4、R 5各自独立地选自取代或未取代的C1-C6直链或支链烷基、取代或未取代的C6-C18芳基、取代或未取代的C3-C18杂芳基中的任意一种。 Preferably, the R 1 , R 2 , R 3 , R 4 , and R 5 are each independently selected from substituted or unsubstituted C1-C6 straight chain or branched chain alkyl, substituted or unsubstituted C6-C18 aryl , any of substituted or unsubstituted C3-C18 heteroaryl groups.
优选地，所述R 1、R 2、R 3、R 4、R 5各自独立地为甲基或苯基；所述R 1和R 2不连接或通过化学键连接成芴环，所述R 4和R 5不连接或通过化学键连接成环。 Preferably, the R 1 , R 2 , R 3 , R 4 , and R 5 are each independently methyl or phenyl; the R 1 and R 2 are not connected or connected to form a fluorene ring through a chemical bond, and the R 4 and R 5 are not connected or connected by a chemical bond to form a ring.
优选地，所述R f1、R f2、R f3各自独立地选自卤素、氰基、取代或未取代的C1-C6直链或支链烷基、取代或未取代的C3-C6环烷基、取代或未取代的C6-C18芳基、取代或未取代的C3-C18杂芳基中的任意一种。 Preferably, the R f1 , R f2 , and R f3 are each independently selected from halogen, cyano, substituted or unsubstituted C1-C6 linear or branched chain alkyl, substituted or unsubstituted C3-C6 cycloalkyl , substituted or unsubstituted C6-C18 aryl, substituted or unsubstituted C3-C18 heteroaryl.
优选地，所述k 1、k 2、k 3均为0。 Preferably, the k 1 , k 2 and k 3 are all 0.
本申请前述提及的“取代或未取代”中存在取代基团时，Ar 1、Ar 2、R 1、R 2、R 3、R 4、R 5、R f1、R f2、R f3中所述取代基团各自独立地选自卤素、C1-C10直链或支链烷基、C3-C10环烷基、C2-C10杂环烷基、C1-C10烷氧基、C1-C10烷硫基、C6-C30芳基氨基、C3-C30杂芳基氨基、C6-C30芳基或C3-C30杂芳基中的至少一种，进一步优选为卤素、C1-C10直链或支链烷基、C3-C10环烷基、C2-C10杂环烷基、C6-C30芳基或C3-C30杂芳基中的至少一种。Ar 3中所述取代基团选自卤素、C1-C6直链或支链烷基、C3-C6环烷基、C1-C6烷氧基或C1-C6烷硫基中的至少一种。 When there is a substituent group in the "substituted or unsubstituted" mentioned above in this application, all of Ar 1 , Ar 2 , R 1 , R 2 , R 3 , R 4 , R 5 , R f1 , R f2 , and R f3 The substituting groups are each independently selected from halogen, C1-C10 straight chain or branched chain alkyl, C3-C10 cycloalkyl, C2-C10 heterocycloalkyl, C1-C10 alkoxy, C1-C10 alkylthio , at least one of C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 aryl or C3-C30 heteroaryl, more preferably halogen, C1-C10 straight chain or branched chain alkyl, At least one of C3-C10 cycloalkyl, C2-C10 heterocycloalkyl, C6-C30 aryl or C3-C30 heteroaryl. The substituent group in Ar 3 is at least one selected from halogen, C1-C6 linear or branched chain alkyl, C3-C6 cycloalkyl, C1-C6 alkoxy or C1-C6 alkylthio.
优选地，所述有机化合物具有如下P1-P496中任一项所示的结构：Preferably, the organic compound has the structure shown in any one of the following P1-P496:
Figure PCTCN2022100562-appb-000008
Figure PCTCN2022100562-appb-000008
Figure PCTCN2022100562-appb-000009
Figure PCTCN2022100562-appb-000009
Figure PCTCN2022100562-appb-000010
Figure PCTCN2022100562-appb-000010
Figure PCTCN2022100562-appb-000011
Figure PCTCN2022100562-appb-000011
Figure PCTCN2022100562-appb-000012
Figure PCTCN2022100562-appb-000012
Figure PCTCN2022100562-appb-000013
Figure PCTCN2022100562-appb-000013
Figure PCTCN2022100562-appb-000014
Figure PCTCN2022100562-appb-000014
Figure PCTCN2022100562-appb-000015
Figure PCTCN2022100562-appb-000015
Figure PCTCN2022100562-appb-000016
Figure PCTCN2022100562-appb-000016
Figure PCTCN2022100562-appb-000017
Figure PCTCN2022100562-appb-000017
Figure PCTCN2022100562-appb-000018
Figure PCTCN2022100562-appb-000018
Figure PCTCN2022100562-appb-000019
Figure PCTCN2022100562-appb-000019
Figure PCTCN2022100562-appb-000020
Figure PCTCN2022100562-appb-000020
Figure PCTCN2022100562-appb-000021
Figure PCTCN2022100562-appb-000021
Figure PCTCN2022100562-appb-000022
Figure PCTCN2022100562-appb-000022
Figure PCTCN2022100562-appb-000023
Figure PCTCN2022100562-appb-000023
Figure PCTCN2022100562-appb-000024
Figure PCTCN2022100562-appb-000024
Figure PCTCN2022100562-appb-000025
Figure PCTCN2022100562-appb-000025
Figure PCTCN2022100562-appb-000026
Figure PCTCN2022100562-appb-000026
Figure PCTCN2022100562-appb-000027
Figure PCTCN2022100562-appb-000027
Figure PCTCN2022100562-appb-000028
Figure PCTCN2022100562-appb-000028
Figure PCTCN2022100562-appb-000029
Figure PCTCN2022100562-appb-000029
Figure PCTCN2022100562-appb-000030
Figure PCTCN2022100562-appb-000030
Figure PCTCN2022100562-appb-000031
Figure PCTCN2022100562-appb-000031
在本申请的一些实施例中，上述有机化合物选自上述P9、P49、P237、P245、P250、P251、P252、P269、P309、P393或P394中的任意一种或多种的混合物时，其应用于有机电致发光器件作为电子阻挡层材料和/或空穴传输层材料，能够更有效提升器件的发光效率和降低驱动电压。In some embodiments of the present application, when the above-mentioned organic compound is selected from any one or more of the above-mentioned P9, P49, P237, P245, P250, P251, P252, P269, P309, P393 or P394, its application Used as an electron blocking layer material and/or a hole transporting layer material in an organic electroluminescent device, it can more effectively improve the luminous efficiency of the device and reduce the driving voltage.
本申请的目的之二在于提供一种如目的之一所述的有机化合物的应用，所述有机化合物应用于有机电致发光器件。The second purpose of the present application is to provide an application of the organic compound described in the first purpose, and the organic compound is applied to an organic electroluminescent device.
优选地，所述有机化合物在有机电致发光器件中作为电子阻挡材料和/或空穴传输材料。Preferably, the organic compound acts as an electron blocking material and/or a hole transporting material in an organic electroluminescent device.
除了有机电致发光器件，本申请的有机化合物还可以应用于照明元件、有机薄膜晶体管、有机场效应晶体管、有机薄膜太阳能电池、信息标签、电子人工皮肤片材、片材型扫描器或电子纸。In addition to organic electroluminescent devices, the organic compounds of the present application can also be applied to lighting elements, organic thin film transistors, organic field effect transistors, organic thin film solar cells, information labels, electronic artificial skin sheets, sheet type scanners or electronic paper .
本申请的目的之三在于提供一种有机电致发光器件，所述有机电致发光器件包括第一电极、第二电极以及设置于所述第一电极与第二电极之间的至少一个有机层；所述有机层中包括至少一种如目的之一所述的有机化合物。The third object of the present application is to provide an organic electroluminescence device, which comprises a first electrode, a second electrode and at least one organic layer arranged between the first electrode and the second electrode ; The organic layer includes at least one organic compound as described in one of the purposes.
优选地，所述有机层包括电子阻挡层，所述电子阻挡层中包括至少一种如目的之一所述的有机化合物。Preferably, the organic layer includes an electron blocking layer, and the electron blocking layer includes at least one organic compound as described in one of the purposes.
本申请提供的有机化合物应用于有机电致发光器件，其作为电子阻挡层材料，尤其作为绿光电子阻挡层材料，能够提高器件的发光效率，并降低驱动电压，使器件具有更好的性能。The organic compound provided by the application is applied to organic electroluminescent devices, and it is used as an electron blocking layer material, especially as a green photoelectron blocking layer material, which can improve the luminous efficiency of the device, reduce the driving voltage, and make the device have better performance.
优选地，所述有机层包括空穴传输层，所述空穴传输层中包括至少一种如目的之一所述的有机化合物。Preferably, the organic layer includes a hole transport layer, and the hole transport layer includes at least one organic compound as described in one of the purposes.
在一个具体技术方案中，所述有机电致发光器件(OLED)包括第一电极和第二电极，以及位于第一电极和第二电极之间的有机层。所述有机层又可以分为多个区域，例如包括空穴传输区、发光层、电子传输区。In a specific technical solution, the organic electroluminescent device (OLED) includes a first electrode and a second electrode, and an organic layer located between the first electrode and the second electrode. The organic layer can be further divided into multiple regions, for example including a hole transport region, a light emitting layer, and an electron transport region.
在具体实施方式中，在第一电极下方或者第二电极上方可以使用基板。基板均为具有机械强度、热稳定性、防水性、透明度优异的玻璃或聚合物材料。此外，作为显示器用的基板上也可以带有薄膜晶体管(TFT)。In particular embodiments, a substrate may be used either below the first electrode or above the second electrode. The substrates are all glass or polymer materials with excellent mechanical strength, thermal stability, water resistance and transparency. In addition, a thin-film transistor (TFT) may be provided on a substrate for a display.
第一电极可以通过在基板上溅射或者沉积用作第一电极的材料的方式来形成。当第一电极作为阳极时，可以采用铟锡氧(ITO)、铟锌氧(IZO)、二氧化锡(SnO 2)、氧化锌(ZnO)等氧化物透明导电材料和它们的任意组合。第一电极作为阴极时，可以采用镁(Mg)、银(Ag)、铝(Al)、铝-锂(Al-Li)、钙(Ca)、镱(Yb)、镁-铟(Mg-In)、镁-银(Mg-Ag)等金属或合金以及它们之间的任意组合。 The first electrode may be formed by sputtering or depositing a material used as the first electrode on the substrate. When the first electrode is used as the anode, oxide transparent conductive materials such as indium tin oxide (ITO), indium zinc oxide (IZO), tin dioxide (SnO 2 ), zinc oxide (ZnO) and any combination thereof can be used. When the first electrode is used as the cathode, magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), ytterbium (Yb), magnesium-indium (Mg-In ), magnesium-silver (Mg-Ag) and other metals or alloys and any combination thereof.
有机层可以通过真空热蒸镀、旋转涂敷、打印等方法形成于电极之上。用作有机层的化合物可以为有机小分子、有机大分子或聚合物，以及它们的组合。The organic layer can be formed on the electrode by vacuum thermal evaporation, spin coating, printing and other methods. Compounds used as organic layers can be small organic molecules, organic macromolecules or polymers, and combinations thereof.
空穴传输区位于阳极和发光层之间。空穴传输区可以为单层结构的空穴传输层(HTL)，包括只含有一种化合物的单层空穴传输层和含有多种化合物的单层空穴传输层。空穴传输区也可以为包括空穴注入层(HIL)、空穴传输层(HTL)、电子阻挡层(EBL)中的至少一层的多层结构；其中HIL位于阳极和HTL之间，EBL位于HTL与发光层之间；HTL和/或EBL中含有至少一种具有式I结构的有机化合物，优选EBL中含有至少一种具有式I结构的有机化合物。The hole transport region is located between the anode and the light emitting layer. The hole transport region can be a hole transport layer (HTL) with a single-layer structure, including a single-layer hole-transport layer containing only one compound and a single-layer hole-transport layer containing multiple compounds. The hole transport region can also be a multilayer structure comprising at least one of a hole injection layer (HIL), a hole transport layer (HTL), and an electron blocking layer (EBL); wherein the HIL is positioned between the anode and the HTL, and the EBL It is located between the HTL and the light-emitting layer; the HTL and/or the EBL contain at least one organic compound with the structure of formula I, preferably the EBL contains at least one organic compound with the structure of formula I.
空穴传输区的材料还可以选自、但不限于酞菁衍生物如CuPc、导电聚合物或含导电掺杂剂的聚合物如聚苯撑乙烯、聚苯胺/十二烷基苯磺酸(Pani/DBSA)、聚(3，4-乙撑二氧噻吩)/聚(4-苯乙烯磺酸盐)(PEDOT/PSS)、聚苯胺/樟脑磺酸(Pani/CSA)、聚苯胺/聚(4-苯乙烯磺酸盐)(Pani/PSS)、芳香胺衍生物，其中芳香胺衍生物包括如下HT-1至HT-51所示的化 合物；或者其任意组合。The material of the hole transport region can also be selected from, but not limited to, phthalocyanine derivatives such as CuPc, conductive polymers or polymers containing conductive dopants such as polyphenylene vinylene, polyaniline/dodecylbenzenesulfonic acid ( Pani/DBSA), poly(3,4-ethylenedioxythiophene)/poly(4-styrenesulfonate) (PEDOT/PSS), polyaniline/camphorsulfonic acid (Pani/CSA), polyaniline/poly (4-styrene sulfonate) (Pani/PSS), aromatic amine derivatives, wherein the aromatic amine derivatives include the following compounds shown in HT-1 to HT-51; or any combination thereof.
Figure PCTCN2022100562-appb-000032
Figure PCTCN2022100562-appb-000032
Figure PCTCN2022100562-appb-000033
Figure PCTCN2022100562-appb-000033
Figure PCTCN2022100562-appb-000034
Figure PCTCN2022100562-appb-000034
空穴注入层位于阳极和空穴传输层之间。空穴注入层可以是单一化合物材料，也可以是多种化合物的组合。例如，空穴注入层可以采用上述HT-1至HT-51的一种或多种化合物，或者采用下述HI-1至HI-3中的一种或多种化合物；也可以采用HT-1至HT-51的一种或多种化合物掺杂下述HI-1至HI-3中的一种或多种化合物。A hole injection layer is located between the anode and the hole transport layer. The hole injection layer can be a single compound material, or a combination of multiple compounds. For example, the hole injection layer can use one or more compounds of the above-mentioned HT-1 to HT-51, or one or more compounds in the following HI-1 to HI-3; HT-1 can also be used One or more compounds to HT-51 are doped with one or more compounds from HI-1 to HI-3 described below.
Figure PCTCN2022100562-appb-000035
Figure PCTCN2022100562-appb-000035
发光层包括可以发射不同波长光谱的发光染料(即掺杂剂，dopant)，还可以同时包括主体材料(Host)。发光层可以是发射红、绿、蓝等单一颜色的单色发光层。多种不同颜色 的单色发光层可以按照像素图形进行平面排列，也可以堆叠在一起而形成彩色发光层。当不同颜色的发光层堆叠在一起时，它们可以彼此隔开，也可以彼此相连。发光层也可以是能同时发射红、绿、蓝等不同颜色的单一彩色发光层。The luminescent layer includes luminescent dyes (that is, dopant) that can emit different wavelength spectra, and can also include a host material (Host) at the same time. The light-emitting layer may be a monochromatic light-emitting layer that emits a single color such as red, green, or blue. A plurality of monochromatic light emitting layers of different colors can be arranged in a plane according to the pixel pattern, and can also be stacked together to form a colored light emitting layer. When the light-emitting layers of different colors are stacked together, they can be separated from each other or connected to each other. The light-emitting layer can also be a single color light-emitting layer capable of simultaneously emitting different colors such as red, green, and blue.
根据不同的技术，发光层材料可以采用荧光电致发光材料、磷光电致发光材料、热活化延迟荧光发光材料等不同的材料。在一个OLED器件中，可以采用单一的发光技术，也可以采用多种不同的发光技术的组合。这些按技术分类的不同发光材料可以发射同种颜色的光，也可以发射不同种颜色的光。According to different technologies, different materials such as fluorescent electroluminescent materials, phosphorescent electroluminescent materials, and heat-activated delayed fluorescent luminescent materials can be used as materials for the light-emitting layer. In an OLED device, a single light-emitting technology can be used, or a combination of multiple different light-emitting technologies can be used. These different luminescent materials classified by technology can emit light of the same color or of different colors.
在本申请的一方面，发光层采用荧光电致发光的技术。其发光层荧光主体材料可以选自、但不限于以下所列举的BFH-1至BFH-17的一种或多种的组合。In one aspect of the present application, the light-emitting layer adopts fluorescence electroluminescence technology. The fluorescent host material of the light-emitting layer can be selected from, but not limited to, one or more combinations of BFH-1 to BFH-17 listed below.
Figure PCTCN2022100562-appb-000036
Figure PCTCN2022100562-appb-000036
在本申请的一方面，发光层采用荧光电致发光的技术。其发光层荧光掺杂剂可以选自、但不限于以下所列举的BFD-1至BFD-24的一种或多种的组合。In one aspect of the present application, the light-emitting layer adopts fluorescence electroluminescence technology. The fluorescent dopant in the light-emitting layer can be selected from, but not limited to, one or more combinations of BFD-1 to BFD-24 listed below.
Figure PCTCN2022100562-appb-000037
Figure PCTCN2022100562-appb-000037
Figure PCTCN2022100562-appb-000038
Figure PCTCN2022100562-appb-000038
Figure PCTCN2022100562-appb-000039
Figure PCTCN2022100562-appb-000039
在本申请的一方面，发光层采用磷光电致发光的技术。其发光层主体材料选自、但不限于PH-1至PH-85中的一种或多种的组合。In one aspect of the present application, the light-emitting layer adopts phosphorescence electroluminescence technology. The host material of the light-emitting layer is selected from, but not limited to, one or more combinations of PH-1 to PH-85.
Figure PCTCN2022100562-appb-000040
Figure PCTCN2022100562-appb-000040
Figure PCTCN2022100562-appb-000041
Figure PCTCN2022100562-appb-000041
Figure PCTCN2022100562-appb-000042
Figure PCTCN2022100562-appb-000042
Figure PCTCN2022100562-appb-000043
Figure PCTCN2022100562-appb-000043
在本申请的一方面，发光层采用磷光电致发光的技术。其发光层磷光掺杂剂可以选自、但不限于以下所列举的GPD-1至GPD-47的一种或多种的组合。In one aspect of the present application, the light-emitting layer adopts phosphorescence electroluminescence technology. The phosphorescent dopant in the light-emitting layer can be selected from, but not limited to, one or more combinations of GPD-1 to GPD-47 listed below.
Figure PCTCN2022100562-appb-000044
Figure PCTCN2022100562-appb-000044
Figure PCTCN2022100562-appb-000045
Figure PCTCN2022100562-appb-000045
Figure PCTCN2022100562-appb-000046
Figure PCTCN2022100562-appb-000046
在本申请的一方面，发光层采用磷光电致发光的技术。其发光层磷光掺杂剂可以选自、但不限于以下所列举的RPD-1至RPD-28的一种或多种的组合。In one aspect of the present application, the light-emitting layer adopts phosphorescence electroluminescence technology. The phosphorescent dopant in the light-emitting layer can be selected from, but not limited to, one or more combinations of RPD-1 to RPD-28 listed below.
Figure PCTCN2022100562-appb-000047
Figure PCTCN2022100562-appb-000047
Figure PCTCN2022100562-appb-000048
Figure PCTCN2022100562-appb-000048
在本申请的一方面，发光层采用磷光电致发光的技术。其发光层磷光掺杂剂可以选自、但不限于以下所列举的YPD-1至YPD-11的一种或多种的组合。In one aspect of the present application, the light-emitting layer adopts phosphorescence electroluminescence technology. The phosphorescent dopant in the light-emitting layer can be selected from, but not limited to, one or more combinations of YPD-1 to YPD-11 listed below.
Figure PCTCN2022100562-appb-000049
Figure PCTCN2022100562-appb-000049
OLED有机层还可以包括发光层与阴极之间的电子传输区。电子传输区可以为单层结构的电子传输层(ETL)，包括只含有一种化合物的单层电子传输层和含有多种化合物的单层电子传输层。电子传输区也可以为包括电子注入层(EIL)、电子传输层(ETL)、空穴阻挡层(HBL)中的至少一层的多层结构。The OLED organic layers may also include an electron transport region between the light emitting layer and the cathode. The electron transport region may be a single-layer electron transport layer (ETL), including a single-layer electron-transport layer containing only one compound and a single-layer electron-transport layer containing multiple compounds. The electron transport region may also be a multilayer structure including at least one of an electron injection layer (EIL), an electron transport layer (ETL), and a hole blocking layer (HBL).
本申请的一方面，电子传输层材料可以选自、但不限于以下所列举的ET-1至ET-73的一种或多种的组合。In one aspect of the present application, the electron transport layer material may be selected from, but not limited to, one or more combinations of ET-1 to ET-73 listed below.
Figure PCTCN2022100562-appb-000050
Figure PCTCN2022100562-appb-000050
Figure PCTCN2022100562-appb-000051
Figure PCTCN2022100562-appb-000051
Figure PCTCN2022100562-appb-000052
Figure PCTCN2022100562-appb-000052
Figure PCTCN2022100562-appb-000053
Figure PCTCN2022100562-appb-000053
本申请的一方面，空穴阻挡层(HBL)位于电子传输层与发光层之间。空穴阻挡层可以采用、但不限于上述ET-1至ET-73的一种或多种化合物，或者采用、但不限于PH-1至PH-46中的一种或多种化合物；也可以采用、但不限于ET-1至ET-73的一种或多种化合物与PH-1至PH-46中的一种或多种化合物之混合物。In one aspect of the present application, a hole blocking layer (HBL) is located between the electron transport layer and the light emitting layer. Hole blocking layer can adopt, but not limited to, one or more compounds of above-mentioned ET-1 to ET-73, or adopt, but not limited to one or more compounds in PH-1 to PH-46; Mixtures of one or more compounds from ET-1 to ET-73 and one or more compounds from PH-1 to PH-46 are used, but are not limited to.
器件中还可以包括位于电子传输层与阴极之间的电子注入层，电子注入层材料包括但不限于以下列举的一种或多种的组合：LiQ、LiF、NaCl、CsF、Li 2O、Cs 2CO 3、BaO、Na、Li、Ca、Mg或Yb。 The device may also include an electron injection layer located between the electron transport layer and the cathode, and the materials of the electron injection layer include but are not limited to one or more combinations of the following: LiQ, LiF, NaCl, CsF, Li 2 O, Cs 2 CO 3 , BaO, Na, Li, Ca, Mg or Yb.
上述空穴注入层、空穴传输层、电子阻挡层、发光层、空穴阻挡层、电子传输层以及电子注入层的厚度均不作限制。为了进一步提高发光器件的发光效率以及进一步降低驱动电压，优选空穴注入层的厚度为8～12nm，优选空穴传输层的厚度为55～65nm，优选电子阻挡层的厚度为30～40nm，优选发光层的厚度为35～45nm，优选空穴阻挡层的厚度为3～8nm，优选电子传输层的厚度为20～30nm，优选电子注入层的厚度为0.8～1.2nm。尤其是当空穴注入层的厚度为10nm，空穴传输层的厚度为60nm，电子阻挡层的厚度为35nm，发光层的厚度为40nm，空穴阻挡层的厚度为5nm，电子传输层的厚度为25nm，电子注入层的厚度为1nm时，得到的电致发光器件具有更为优异的发光效率和更低的驱动电压。The thicknesses of the above hole injection layer, hole transport layer, electron blocking layer, light emitting layer, hole blocking layer, electron transport layer and electron injection layer are not limited. In order to further improve the luminous efficiency of the light-emitting device and further reduce the driving voltage, the thickness of the hole injection layer is preferably 8 to 12 nm, the thickness of the hole transport layer is preferably 55 to 65 nm, and the thickness of the electron blocking layer is preferably 30 to 40 nm. The thickness of the light-emitting layer is 35-45 nm, the thickness of the hole blocking layer is preferably 3-8 nm, the thickness of the electron transport layer is preferably 20-30 nm, and the thickness of the electron injection layer is preferably 0.8-1.2 nm. Especially when the thickness of the hole injection layer is 10nm, the thickness of the hole transport layer is 60nm, the thickness of the electron blocking layer is 35nm, the thickness of the light-emitting layer is 40nm, the thickness of the hole blocking layer is 5nm, and the thickness of the electron transport layer is When the thickness of the electron injection layer is 25nm and the thickness of the electron injection layer is 1nm, the obtained electroluminescent device has more excellent luminous efficiency and lower driving voltage.
相对于现有技术，本申请具有以下有益效果：Compared with the prior art, the present application has the following beneficial effects:
本申请提供的有机化合物具有如式I所示结构，所述有机化合物通过分子结构的设计，具有更好的稳定性和光电性质，可以提高和平衡载流子传输，改善器件性能；同时，所述有机化合物的分子量适宜，蒸镀温度相对较低，有利于有机电致发光器件的工业化生产。所述有机化合物用于有机电致发光器件的电子阻挡层材料，能够降低器件的驱动电压，提升发光效率，使OLED器件具有更好的综合性能。同时，所述有机化合物的制备方法简单，原料易得，易于实现规模化量产。The organic compound provided by this application has a structure as shown in formula I. The organic compound has better stability and photoelectric properties through the design of molecular structure, which can improve and balance carrier transport and improve device performance; at the same time, the The molecular weight of the above-mentioned organic compound is suitable, and the evaporation temperature is relatively low, which is beneficial to the industrial production of organic electroluminescent devices. The organic compound is used as an electron blocking layer material of an organic electroluminescent device, which can reduce the driving voltage of the device, improve luminous efficiency, and make the OLED device have better comprehensive performance. At the same time, the preparation method of the organic compound is simple, the raw materials are readily available, and it is easy to realize large-scale mass production.
具体实施方式detailed description
下面通过具体实施方式来进一步说明本申请的技术方案。本领域技术人员应该明了，所述实施例仅仅是帮助理解本申请，不应视为对本申请的具体限制。The technical solutions of the present application will be further described below through specific implementation methods. It should be clear to those skilled in the art that the embodiments are only for helping to understand the present application, and should not be regarded as a specific limitation on the present application.
本申请中，具有式I所示结构的有机化合物的代表合成路径如下所示：In the present application, the representative synthetic route of the organic compound having the structure shown in formula I is as follows:
Figure PCTCN2022100562-appb-000054
Figure PCTCN2022100562-appb-000054
Figure PCTCN2022100562-appb-000055
Figure PCTCN2022100562-appb-000055
其中，Ar 1、Ar 2、Ar 3、X、R f1、R f2、R f3、k 1、k 2、k 3具有与式I中的相同的含义；Pd(PPh 3) 4代表四三苯基膦钯，Pd 2(dba) 3代表三(二苄基丙酮)二钯(0)，Sphos代表2-双环己基磷-2′，6′-二甲氧基联苯，IPr.HCl代表1，3-双(2，6-二异丙基苯基)氯化咪唑鎓，NaOBu-t代表叔丁醇钠，(t-Bu) 3P代表三叔丁基膦。 Among them, Ar 1 , Ar 2 , Ar 3 , X, R f1 , R f2 , R f3 , k 1 , k 2 , and k 3 have the same meanings as in formula I; Pd(PPh 3 ) 4 represents tetrakistriphenyl Palladium phosphine, Pd 2 (dba) 3 represents tris(dibenzylacetone) dipalladium (0), Sphos represents 2-bicyclohexylphosphine-2′,6′-dimethoxybiphenyl, IPr.HCl represents 1 , 3-bis(2,6-diisopropylphenyl) imidazolium chloride, NaOBu-t represents sodium tert-butoxide, (t-Bu) 3 P represents tri-tert-butylphosphine.
本申请所述有机化合物的制备包括上述方法，但不限于上述方法，本领域技术人员采用其他方法合成得到的式I所示有机化合物同样属于本申请的保护范围。The preparation of the organic compound described in the present application includes, but is not limited to, the above-mentioned method. The organic compound represented by formula I synthesized by those skilled in the art by other methods also belongs to the protection scope of the present application.
更具体地，本申请如下合成例示例性地提供了所述有机化合物的具体合成方法，如下合成例中所用溶剂和试剂，均可以从化工产品市场购买或定制。另外，本领域技术人员也可以通过其他公知方法合成。More specifically, the following synthesis examples in this application exemplarily provide the specific synthesis methods of the organic compounds. The solvents and reagents used in the following synthesis examples can be purchased or customized from the chemical product market. In addition, those skilled in the art can also synthesize by other known methods.
以下合成例中的质谱表征数据通过英国Micromass公司制造的ZAB-HS型质谱仪测试得到。The mass spectrometric characterization data in the following synthesis examples were obtained by testing with a ZAB-HS mass spectrometer manufactured by Micromass, UK.
合成例1：有机化合物P9Synthesis Example 1: Organic Compound P9
Figure PCTCN2022100562-appb-000056
Figure PCTCN2022100562-appb-000056
Figure PCTCN2022100562-appb-000057
Figure PCTCN2022100562-appb-000057
在1000mL单口瓶中，加入20.0g的M1、20.7g的2-联苯硼酸、1.2g四三苯基膦钯Pd(PPh 3) 4、28.9g碳酸钾、300mL 1，4-二氧六环和100mL水，抽真空换氮气3次，反应升温至100℃反应5h。反应完毕，停止反应。冷却至室温，对反应液分液，有机相经过两次硅胶柱纯化，浓缩有机相，加入甲醇回流搅拌1h，抽滤得到淡黄色粉末M1-1，然后用乙酸乙酯重结晶得到纯品22.9g。 In a 1000mL single-necked bottle, add 20.0g of M1, 20.7g of 2-biphenylboronic acid, 1.2g of tetrakistriphenylphosphine palladium Pd(PPh 3 ) 4 , 28.9g of potassium carbonate, 300mL of 1,4-dioxane and 100mL of water, vacuumed and changed nitrogen for 3 times, and the reaction temperature was raised to 100°C for 5h. After the reaction is complete, stop the reaction. Cool to room temperature, separate the reaction liquid, purify the organic phase through silica gel column twice, concentrate the organic phase, add methanol to reflux and stir for 1 h, filter with suction to obtain light yellow powder M1-1, and then recrystallize with ethyl acetate to obtain pure product 22.9 g.
M1-1：m/z理论值：309；m/z实测值：310。M1-1: m/z theoretical value: 309; m/z measured value: 310.
在1000mL单口瓶中，加入22.9g的M1-1、13.5g的苯硼酸、0.7g三(二苄基丙酮)二钯(0)Pd 2(dba) 3、0.6g 2-双环己基膦-2′，6′-二甲氧基联苯(Sphos)，31.4g无水磷酸钾，400mL 1，4-二氧六环和40mL水，抽真空换氮气3次，反应升温至100℃反应5h。反应完毕，停止反应。冷却至室温，对反应液分液，有机相经过两次硅胶柱纯化，浓缩有机相，加入甲醇回流搅拌1h，抽滤得到淡黄色粉末M1-2，然后用乙酸乙酯重结晶得到纯品16.9g。 In a 1000mL single-necked bottle, add 22.9g of M1-1, 13.5g of phenylboronic acid, 0.7g of tris(dibenzylacetone)dipalladium(0)Pd 2 (dba) 3 , 0.6g of 2-bicyclohexylphosphine-2 ',6'-Dimethoxybiphenyl (Sphos), 31.4g of anhydrous potassium phosphate, 400mL of 1,4-dioxane and 40mL of water, vacuumed and changed nitrogen for 3 times, and the reaction temperature was raised to 100°C for 5h. After the reaction is complete, stop the reaction. Cool to room temperature, separate the reaction liquid, purify the organic phase through silica gel column twice, concentrate the organic phase, add methanol to reflux and stir for 1 h, filter with suction to obtain light yellow powder M1-2, and then recrystallize with ethyl acetate to obtain pure product 16.9 g.
M1-2：m/z理论值：351；m/z实测值：352。M1-2: m/z theoretical value: 351; m/z measured value: 352.
在1000mL单口瓶中，加入16.9g的M1-2、2mL水合肼、0.5g钯碳(Pd/C)和300mL乙醇，抽真空换氮气3次，反应升温至90℃反应5h。反应完毕，停止反应。冷却至室温，对反应液分液，有机相经过两次硅胶柱纯化，浓缩有机相，加入甲醇回流搅拌1h，抽滤得到白色粉末M1-3，然后用乙酸乙酯重结晶得到纯品14.5g。In a 1000mL single-necked bottle, add 16.9g of M1-2, 2mL of hydrazine hydrate, 0.5g of palladium carbon (Pd/C) and 300mL of ethanol, vacuum and change nitrogen for 3 times, and the reaction temperature is raised to 90°C for 5h. After the reaction is complete, stop the reaction. Cool to room temperature, separate the reaction liquid, purify the organic phase through silica gel column twice, concentrate the organic phase, add methanol to reflux and stir for 1 h, filter with suction to obtain white powder M1-3, and then recrystallize with ethyl acetate to obtain 14.5 g of pure product .
M1-3：m/z理论值：321；m/z实测值：322。M1-3: m/z theoretical value: 321; m/z measured value: 322.
在1000mL单口瓶中，加入14.5g的M1-3、12.3g的2-溴-9，9-二甲基芴、0.4g的Pd 2(dba) 3、0.4g的1，3-双(2，6-二异丙基苯基)氯化咪唑鎓(IPr.HCl)，13.0g叔丁醇钠NaOBu-t，300mL甲苯，抽真空换氮气3次，反应升温至90℃反应5h。反应完毕，停止反应。冷却至室温，对反应液分液，有机相经过两次硅胶柱纯化，浓缩有机相，加入甲醇回流搅拌1h，抽滤得到淡黄色粉末M1-4，然后用乙酸乙酯重结晶得到纯品17.1g。 In a 1000mL single-necked bottle, add 14.5g of M1-3, 12.3g of 2-bromo-9,9-dimethylfluorene, 0.4g of Pd 2 (dba) 3 , 0.4g of 1,3-bis(2 , 6-diisopropylphenyl)imidazolium chloride (IPr.HCl), 13.0g sodium tert-butoxide NaOBu-t, 300mL toluene, vacuum and change nitrogen 3 times, and the reaction temperature was raised to 90°C for 5h. After the reaction is complete, stop the reaction. Cool to room temperature, separate the reaction solution, purify the organic phase through silica gel column twice, concentrate the organic phase, add methanol to reflux and stir for 1 h, filter with suction to obtain light yellow powder M1-4, and then recrystallize with ethyl acetate to obtain pure product 17.1 g.
M1-4：m/z理论值：513；m/z实测值：514。M1-4: m/z theoretical value: 513; m/z measured value: 514.
在1000mL单口瓶中，加入17.1g的M1-4、7.7g的4-溴联苯、0.3g的Pd 2(dba) 3、0.4mL叔丁基膦(t-Bu) 3P、9.6g叔丁醇钠和300mL甲苯，抽真空换氮气3次，反应升温至110℃反应5h。反应完毕，停止反应。冷却至室温，对反应液分液，有机相经过两次硅胶柱纯化，浓缩有机相，加入甲醇回流搅拌1h，抽滤得到淡黄色粉末P9，然后乙酸乙酯重结晶三次的到纯品8.5g。 In a 1000 mL single-necked bottle, add 17.1 g of M1-4, 7.7 g of 4-bromobiphenyl, 0.3 g of Pd 2 (dba) 3 , 0.4 mL of tert-butylphosphine (t-Bu) 3 P, 9.6 g of t- Sodium butoxide and 300mL of toluene were vacuumed and replaced with nitrogen three times, and the reaction temperature was raised to 110°C for 5 hours. After the reaction is complete, stop the reaction. Cool to room temperature, separate the reaction liquid, purify the organic phase through silica gel column twice, concentrate the organic phase, add methanol to reflux and stir for 1 h, filter with suction to obtain light yellow powder P9, and then recrystallize three times from ethyl acetate to obtain 8.5 g of pure product .
有机化合物P9：m/z理论值：665；m/z实测值：666。Organic compound P9: m/z theoretical: 665; m/z found: 666.
合成例2-11Synthesis Example 2-11
合成例2-11的工艺路线与合成例1相同，区别在于原料不同，原料、目标产物及结果表征数据如表1所示。The process routes of Synthesis Examples 2-11 are the same as those of Synthesis Example 1, except that the raw materials are different. The raw materials, target products and characterization data of the results are shown in Table 1.
表1Table 1
Figure PCTCN2022100562-appb-000058
Figure PCTCN2022100562-appb-000058
Figure PCTCN2022100562-appb-000059
Figure PCTCN2022100562-appb-000059
实施例1Example 1
一种有机电致发光器件，包括依次设置的阳极(ITO)、空穴注入层、空穴传输层、电子阻挡层、发光层、空穴阻挡层、电子传输层、电子注入层和阴极(Al)。A kind of organic electroluminescence device, comprises anode (ITO), hole injection layer, hole transport layer, electron blocking layer, light-emitting layer, hole blocking layer, electron transport layer, electron injection layer and negative electrode (Al ).
所述有机电致发光器件的制备方法如下：将涂布了ITO透明导电层的玻璃板在商用清洗剂中超声处理，在去离子水中冲洗，在丙酮/乙醇的混合溶剂中超声除油，在洁净环境下烘烤至完全除去水分，用紫外光和臭氧清洗，并用低能阳离子束轰击表面；把上述带有阳极的玻璃基片置于真空腔内，抽真空至＜1×10 -5Pa，在上述阳极层膜上按先后顺序真空热蒸镀10nm的化合物HT-4∶HI-3(97/3，w/w)混合物作为空穴注入层，60nm的化合物HT-4作为空穴传输层，35nm的本申请提供的有机化合物P9作为电子阻挡层；40nm的化合物PH-61∶PH-3∶GPD-12(100∶100∶20，w/w)三元混合物作为发光层；5nm的ET-23作为空穴阻挡层，25nm的化合物ET-69∶ET-57(50/50，w/w)混合物作为电子传输层，1nm的LiF作 为电子注入层，150nm的金属铝作为阴极；所有有机层和LiF的蒸镀总速率控制在0.1nm/s，金属电极的蒸镀速率控制在1nm/s。 The preparation method of the organic electroluminescent device is as follows: the glass plate coated with the ITO transparent conductive layer is ultrasonically treated in a commercial cleaning agent, rinsed in deionized water, and ultrasonically degreased in a mixed solvent of acetone/ethanol. Baking in a clean environment until moisture is completely removed, cleaning with ultraviolet light and ozone, and bombarding the surface with a low-energy positive ion beam; placing the above-mentioned glass substrate with an anode in a vacuum chamber, and evacuating to <1×10 -5 Pa, On the above-mentioned anode layer film, 10nm compound HT-4: HI-3 (97/3, w/w) mixture was vacuum thermally evaporated sequentially as the hole injection layer, and 60nm compound HT-4 was used as the hole transport layer , 35nm of the organic compound P9 provided by the application as an electron blocking layer; 40nm of the compound PH-61:PH-3:GPD-12 (100:100:20, w/w) ternary mixture as the light-emitting layer; 5nm of ET -23 as hole blocking layer, 25nm compound ET-69:ET-57 (50/50, w/w) mixture as electron transport layer, 1nm LiF as electron injection layer, 150nm metal aluminum as cathode; all organic The total evaporation rate of layer and LiF is controlled at 0.1nm/s, and the evaporation rate of metal electrode is controlled at 1nm/s.
实施例2-11Example 2-11
一种有机电致发光器件，其与实施例1的区别仅在于，将电子阻挡层材料有机化合物P9替换为P49、P237、P245、P250、P251、P252、P269、P309、P393、P394。An organic electroluminescent device, the only difference from Example 1 is that the electronic blocking layer material organic compound P9 is replaced by P49, P237, P245, P250, P251, P252, P269, P309, P393, P394.
对比例1-5Comparative example 1-5
一种有机电致发光器件，其与实施例1的区别仅在于，将电子阻挡层材料有机化合物P9替换为CCP-1、CCP-2、CCP-3、CCP-4、CCP-5。An organic electroluminescent device, the only difference from Example 1 is that the electron blocking layer material organic compound P9 is replaced by CCP-1, CCP-2, CCP-3, CCP-4, CCP-5.
Figure PCTCN2022100562-appb-000060
Figure PCTCN2022100562-appb-000060
对上述实施例1-11和对比例1-5提供的有机电致发光器件进行如下性能测试：在同样亮度下，使用数字源表及亮度计测定有机电致发光器件的驱动电压和电流效率。具体而言，以每秒0.1V的速率提升电压，测定当有机电致发光器件的亮度达到10000cd/m 2时的电压即驱动电压，同时测出此时的电流密度；亮度与电流密度的比值即为电流效率；测试结果如表2所示。 The following performance tests were performed on the organic electroluminescent devices provided in Examples 1-11 and Comparative Examples 1-5: Under the same brightness, the driving voltage and current efficiency of the organic electroluminescent devices were measured using a digital source meter and a luminance meter. Specifically, increase the voltage at a rate of 0.1V per second , measure the voltage when the brightness of the organic electroluminescent device reaches 10000cd/m2, that is, the driving voltage, and measure the current density at this time; the ratio of brightness to current density That is the current efficiency; the test results are shown in Table 2.
表2Table 2
Figure PCTCN2022100562-appb-000061
Figure PCTCN2022100562-appb-000061
Figure PCTCN2022100562-appb-000062
Figure PCTCN2022100562-appb-000062
根据表2的结果可知，本申请提供的有机化合物应用于有机电致发光器件，可以使器件在10000cd/m 2亮度下的驱动电压为4.0-4.2V，电流效率为66.4-68.1cd/A，从而有效地降低驱动电压，提高电流效率，是性能良好的绿光电子阻挡层材料。 According to the results in Table 2, it can be seen that the organic compound provided by the present application is applied to an organic electroluminescent device, which can make the driving voltage of the device under the brightness of 10000cd/m 2 be 4.0-4.2V, and the current efficiency is 66.4-68.1cd/A, Therefore, the driving voltage can be effectively reduced, the current efficiency can be improved, and it is a green photoelectron blocking layer material with good performance.
对比例1中的电子阻挡层材料CCP-1与实施例2的P237的区别仅在于，CCP-1中的芴基与N原子之间通过亚苯基连接，使CCP-1的迁移率降低，分子堆积致密性差，从而影响了器件的发光效率和驱动电压；对比例2-4中的电子阻挡层材料中，芳胺N原子分别连接于芴基的1-位、3-位、4-位，与N原子连接于芴基的2-位相比，迁移率较低，不利于激子的传输，故而器件性能较差；对比例5中的芳胺N邻位没有连接取代基，使分子的LUMO能级较深，降低了器件的发光性能。The difference between the electron blocking layer material CCP-1 in Comparative Example 1 and P237 in Example 2 is that the fluorenyl group in CCP-1 is connected to the N atom through a phenylene group, which reduces the mobility of CCP-1. The molecular packing density is poor, which affects the luminous efficiency and driving voltage of the device; in the electron blocking layer materials in Comparative Examples 2-4, the N atoms of the arylamine are connected to the 1-position, 3-position, and 4-position of the fluorenyl group respectively , compared with the 2-position where the N atom is connected to the fluorenyl group, the mobility is lower, which is not conducive to the transmission of excitons, so the device performance is poor; the N-ortho position of the arylamine in Comparative Example 5 has no substituents connected, so that the molecular The LUMO energy level is deep, which reduces the luminescent performance of the device.
申请人声明，本申请通过上述实施例来说明本申请的一种有机化合物及其应用，但本申请并不局限于上述实施例，即不意味着本申请必须依赖上述实施例才能实施。所属技术领域的技术人员应该明了，对本申请的任何改进，对本申请产品各原料的等效替换及辅助成分的添加、具体方式的选择等，均落在本申请的保护范围和公开范围之内。The applicant declares that the application uses the above examples to illustrate an organic compound of the application and its application, but the application is not limited to the above examples, that is, it does not mean that the application must rely on the above examples to be implemented. Those skilled in the art should understand that any improvement to the present application, the equivalent replacement of each raw material of the product of the present application, the addition of auxiliary components, the selection of specific methods, etc., all fall within the scope of protection and disclosure of the present application.

Claims (11)

  1. 一种有机化合物，其特征在于，所述有机化合物具有如式I所示结构：An organic compound, characterized in that the organic compound has a structure as shown in formula I:
    Figure PCTCN2022100562-appb-100001
    Figure PCTCN2022100562-appb-100001
    其中，Ar 1、Ar 2各自独立地选自取代或未取代的C6-C30芳基、取代或未取代的C3-C30杂芳基中的任意一种； Wherein, Ar 1 and Ar 2 are each independently selected from any one of substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl;
    Ar 3选自取代或未取代的C6-C12芳基、取代或未取代的C3-C11杂芳基中的任意一种； Ar 3 is selected from any one of substituted or unsubstituted C6-C12 aryl, substituted or unsubstituted C3-C11 heteroaryl;
    X选自O、S、CR 1R 2、NR 3或SiR 4R 5中的任意一种； X is selected from any one of O, S, CR 1 R 2 , NR 3 or SiR 4 R 5 ;
    R 1、R 2、R 3、R 4、R 5各自独立地选自氢、取代或未取代的C1-C20直链或支链烷基、取代或未取代的C3-C20环烷基、取代或未取代的C2-C12烯基、取代或未取代的C2-C12炔基、取代或未取代的C6-C30芳基、取代或未取代的C3-C30杂芳基中的任意一种； R 1 , R 2 , R 3 , R 4 , and R 5 are each independently selected from hydrogen, substituted or unsubstituted C1-C20 linear or branched chain alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted Or any of unsubstituted C2-C12 alkenyl, substituted or unsubstituted C2-C12 alkynyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl;
    R 1和R 2不连接或通过化学键连接成环，R 4和R 5不连接或通过化学键连接成环； R 1 and R 2 are not connected or are connected to form a ring by a chemical bond, R 4 and R 5 are not connected or are connected to form a ring by a chemical bond;
    R f1、R f2、R f3各自独立地选自卤素、氰基、取代或未取代的C1-C20直链或支链烷基、取代或未取代的C3-C20环烷基、取代或未取代的C2-C12烯基、取代或未取代的C2-C12炔基、取代或未取代的C6-C30芳基、取代或未取代的C3-C30杂芳基中的任意一种； R f1 , R f2 , and R f3 are each independently selected from halogen, cyano, substituted or unsubstituted C1-C20 linear or branched chain alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted Any one of C2-C12 alkenyl, substituted or unsubstituted C2-C12 alkynyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl;
    Ar 1、Ar 2、R 1、R 2、R 3、R 4、R 5、R f1、R f2、R f3中所述取代的取代基各自 独立地选自卤素、C1-C10直链或支链烷基、C3-C10环烷基、C2-C10杂环烷基、C1-C10烷氧基、C1-C10烷硫基、C6-C30芳基氨基、C3-C30杂芳基氨基、C6-C30芳基或C3-C30杂芳基中的至少一种； Ar 1 , Ar 2 , R 1 , R 2 , R 3 , R 4 , R 5 , R f1 , R f2 , and R f3 are each independently selected from halogen, C1-C10 straight chain or branched Alkanyl, C3-C10 cycloalkyl, C2-C10 heterocycloalkyl, C1-C10 alkoxy, C1-C10 alkylthio, C6-C30 arylamino, C3-C30 heteroarylamino, C6- At least one of C30 aryl or C3-C30 heteroaryl;
    Ar 3中所述取代的取代基选自卤素、C1-C6直链或支链烷基、C3-C6环烷基、C1-C6烷氧基或C1-C6烷硫基中的至少一种； The substituted substituent in Ar 3 is selected from at least one of halogen, C1-C6 linear or branched chain alkyl, C3-C6 cycloalkyl, C1-C6 alkoxy or C1-C6 alkylthio;
    k 1、k 2各自独立地为0-3的整数；k 3为0-4的整数。 k 1 and k 2 are each independently an integer of 0-3; k 3 is an integer of 0-4.
  2. 根据权利要求1所述的有机化合物，其特征在于，所述Ar 1、Ar 2各自独立地选自取代或未取代的C6-C20芳基、取代或未取代的C10-C20稠环杂芳基中的任意一种； The organic compound according to claim 1, wherein said Ar 1 and Ar 2 are each independently selected from substituted or unsubstituted C6-C20 aryl, substituted or unsubstituted C10-C20 fused ring heteroaryl any of the
    优选地，所述Ar 1、Ar 2各自独立地选自取代或未取代的如下基团中的任意一种： Preferably, the Ar 1 and Ar 2 are each independently selected from any of the following substituted or unsubstituted groups:
    Figure PCTCN2022100562-appb-100002
    Figure PCTCN2022100562-appb-100002
    其中，*代表基团的连接位点；Wherein, * represents the connection site of the group;
    Z选自O、S、CR 11R 12、NR 13或SiR 14R 15中的任意一种； Z is selected from any one of O, S, CR 11 R 12 , NR 13 or SiR 14 R 15 ;
    R 11、R 12、R 13、R 14、R 15各自独立地选自氢、取代或未取代的C1-C20直链 或支链烷基、取代或未取代的C3-C20环烷基、取代或未取代的C2-C12烯基、取代或未取代的C2-C12炔基、取代或未取代的C6-C30芳基、取代或未取代的C3-C30杂芳基中的任意一种； R 11 , R 12 , R 13 , R 14 , and R 15 are each independently selected from hydrogen, substituted or unsubstituted C1-C20 linear or branched chain alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted Or any of unsubstituted C2-C12 alkenyl, substituted or unsubstituted C2-C12 alkynyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl;
    R 11和R 12不连接或通过化学键连接成环，R 14和R 15不连接或通过化学键连接成环； R 11 and R 12 are not connected or are connected to form a ring through a chemical bond, R 14 and R 15 are not connected or are connected to form a ring through a chemical bond;
    优选地，所述R 11、R 12、R 13、R 14、R 15各自独立地为甲基或苯基；R 11和R 12不连接或通过化学键连接成环，R 14和R 15不连接或通过化学键连接成环。 Preferably, the R 11 , R 12 , R 13 , R 14 , and R 15 are each independently methyl or phenyl; R 11 and R 12 are not connected or connected to form a ring through a chemical bond, and R 14 and R 15 are not connected Or connect to form a ring by chemical bonds.
  3. 根据权利要求1或2所述的有机化合物，其特征在于，所述Ar 1选自取代或未取代的如下基团中的任意一种： The organic compound according to claim 1 or 2, wherein the Ar is selected from any one of substituted or unsubstituted following groups:
    Figure PCTCN2022100562-appb-100003
    Figure PCTCN2022100562-appb-100003
    其中，*代表基团的连接位点；Wherein, * represents the connection site of the group;
    优选地，所述Ar 2选自取代或未取代的如下基团中的任意一种：
    Figure PCTCN2022100562-appb-100004
    Figure PCTCN2022100562-appb-100005
    Preferably, the Ar is selected from any one of the following substituted or unsubstituted groups :
    Figure PCTCN2022100562-appb-100004
    Figure PCTCN2022100562-appb-100005
    其中，*代表基团的连接位点。Among them, * represents the linking site of the group.
  4. 根据权利要求1所述的有机化合物，其特征在于，所述Ar 1和Ar 2不同时为苯基。 The organic compound according to claim 1, characterized in that, the Ar 1 and Ar 2 are not simultaneously phenyl groups.
  5. 根据权利要求1所述的有机化合物，其特征在于，所述Ar 3为取代或未取代的苯基、取代或未取代的联苯基，所述取代的取代基选自卤素、C1-C6直链或支链烷基、C3-C6环烷基、C1-C6烷氧基或C1-C6烷硫基中的至少一种； The organic compound according to claim 1 , wherein the Ar is substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, and the substituted substituent is selected from halogen, C1-C6 straight At least one of chain or branched alkyl, C3-C6 cycloalkyl, C1-C6 alkoxy or C1-C6 alkylthio;
    优选地，所述Ar 3为苯基。 Preferably, the Ar 3 is phenyl.
  6. 根据权利要求1所述的有机化合物，其特征在于，所述X为CR 1R 2、NR 3或SiR 4R 5，优选为CR 1R 2； The organic compound according to claim 1, wherein the X is CR 1 R 2 , NR 3 or SiR 4 R 5 , preferably CR 1 R 2 ;
    优选地，所述R 1、R 2、R 3、R 4、R 5各自独立地选自取代或未取代的C1-C6直链或支链烷基、取代或未取代的C6-C18芳基、取代或未取代的C3-C18杂芳基中的任意一种； Preferably, the R 1 , R 2 , R 3 , R 4 , and R 5 are each independently selected from substituted or unsubstituted C1-C6 straight chain or branched chain alkyl, substituted or unsubstituted C6-C18 aryl , any of substituted or unsubstituted C3-C18 heteroaryl;
    优选地，所述R 1、R 2、R 3、R 4、R 5各自独立地为甲基或苯基；所述R 1和R 2不连接或通过化学键连接成芴环，所述R 4和R 5不连接或通过化学键连接成环。 Preferably, the R 1 , R 2 , R 3 , R 4 , and R 5 are each independently methyl or phenyl; the R 1 and R 2 are not connected or connected to form a fluorene ring through a chemical bond, and the R 4 and R 5 are not connected or connected by a chemical bond to form a ring.
  7. 根据权利要求1所述的化合物，其特征在于，所述R f1、R f2、R f3各自独立地选自卤素、氰基、取代或未取代的C1-C6直链或支链烷基、取代或未取代的C3-C6环烷基、取代或未取代的C6-C18芳基、取代或未取代的C3-C18杂芳基中的任意一种； The compound according to claim 1, wherein each of said R f1 , R f2 , and R f3 is independently selected from halogen, cyano, substituted or unsubstituted C1-C6 straight or branched chain alkyl, substituted Or any of unsubstituted C3-C6 cycloalkyl, substituted or unsubstituted C6-C18 aryl, substituted or unsubstituted C3-C18 heteroaryl;
    优选地，所述k 1、k 2、k 3均为0。 Preferably, the k 1 , k 2 and k 3 are all 0.
  8. 根据权利要求1所述的有机化合物，其特征在于，所述有机化合物具有如下P1-P496中任一项所示的结构：The organic compound according to claim 1, wherein the organic compound has a structure shown in any one of the following P1-P496:
    Figure PCTCN2022100562-appb-100006
    Figure PCTCN2022100562-appb-100006
    Figure PCTCN2022100562-appb-100007
    Figure PCTCN2022100562-appb-100007
    Figure PCTCN2022100562-appb-100008
    Figure PCTCN2022100562-appb-100008
    Figure PCTCN2022100562-appb-100009
    Figure PCTCN2022100562-appb-100009
    Figure PCTCN2022100562-appb-100010
    Figure PCTCN2022100562-appb-100010
    Figure PCTCN2022100562-appb-100011
    Figure PCTCN2022100562-appb-100011
    Figure PCTCN2022100562-appb-100012
    Figure PCTCN2022100562-appb-100012
    Figure PCTCN2022100562-appb-100013
    Figure PCTCN2022100562-appb-100013
    Figure PCTCN2022100562-appb-100014
    Figure PCTCN2022100562-appb-100014
    Figure PCTCN2022100562-appb-100015
    Figure PCTCN2022100562-appb-100015
    Figure PCTCN2022100562-appb-100016
    Figure PCTCN2022100562-appb-100016
    Figure PCTCN2022100562-appb-100017
    Figure PCTCN2022100562-appb-100017
    Figure PCTCN2022100562-appb-100018
    Figure PCTCN2022100562-appb-100018
    Figure PCTCN2022100562-appb-100019
    Figure PCTCN2022100562-appb-100019
    Figure PCTCN2022100562-appb-100020
    Figure PCTCN2022100562-appb-100020
    Figure PCTCN2022100562-appb-100021
    Figure PCTCN2022100562-appb-100021
    Figure PCTCN2022100562-appb-100022
    Figure PCTCN2022100562-appb-100022
    Figure PCTCN2022100562-appb-100023
    Figure PCTCN2022100562-appb-100023
    Figure PCTCN2022100562-appb-100024
    Figure PCTCN2022100562-appb-100024
    Figure PCTCN2022100562-appb-100025
    Figure PCTCN2022100562-appb-100025
    Figure PCTCN2022100562-appb-100026
    Figure PCTCN2022100562-appb-100026
    Figure PCTCN2022100562-appb-100027
    Figure PCTCN2022100562-appb-100027
    Figure PCTCN2022100562-appb-100028
    Figure PCTCN2022100562-appb-100028
    Figure PCTCN2022100562-appb-100029
    Figure PCTCN2022100562-appb-100029
  9. 根据权利要求8所述的有机化合物，其特征在于，所述有机化合物选自P9、P49、P237、P245、P250、P251、P252、P269、P309、P393或P394中的至少一种。The organic compound according to claim 8, wherein the organic compound is selected from at least one of P9, P49, P237, P245, P250, P251, P252, P269, P309, P393 or P394.
  10. 一种如权利要求1-9中任一项所述的有机化合物的应用，其特征在于，所述有机化合物应用于有机电致发光器件、照明元件、有机薄膜晶体管、有机场效应晶体管、有机薄膜太阳能电池、信息标签、电子人工皮肤片材、片材型扫描器或电子纸；A kind of application of the organic compound as described in any one in claim 1-9, it is characterized in that, described organic compound is applied to organic electroluminescence device, illuminating element, organic thin film transistor, organic field effect transistor, organic thin film Solar cells, information labels, electronic artificial skin sheets, sheet-type scanners or electronic paper;
    优选地，所述有机化合物在有机电致发光器件中作为电子阻挡材料和/或空穴传输材料。Preferably, the organic compound acts as an electron blocking material and/or a hole transporting material in an organic electroluminescent device.
  11. 一种有机电致发光器件，其特征在于，所述有机电致发光器件包括第一电极、第二电极以及设置于所述第一电极与第二电极之间的至少一个有机层；所述有机层中包括至少一种如权利要求1-9中任一项所述的有机化合物；An organic electroluminescent device, characterized in that the organic electroluminescent device comprises a first electrode, a second electrode and at least one organic layer arranged between the first electrode and the second electrode; the organic The layer comprises at least one organic compound according to any one of claims 1-9;
    优选地，所述有机层包括电子阻挡层，所述电子阻挡层中包括至少一种如权利要求1-9中任一项所述的有机化合物；Preferably, the organic layer includes an electron blocking layer, and the electron blocking layer includes at least one organic compound according to any one of claims 1-9;
    优选地，所述有机层包括空穴传输层，所述空穴传输层中包括至少一种如权利要求1-9中任一项所述的有机化合物。Preferably, the organic layer includes a hole transport layer, and the hole transport layer includes at least one organic compound according to any one of claims 1-9.
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