[go: up one dir, main page]
More Web Proxy on the site http://driver.im/

WO2022267801A1 - 一种有机化合物及包含其的有机电致发光器件和电子装置 - Google Patents

一种有机化合物及包含其的有机电致发光器件和电子装置 Download PDF

Info

Publication number
WO2022267801A1
WO2022267801A1 PCT/CN2022/094927 CN2022094927W WO2022267801A1 WO 2022267801 A1 WO2022267801 A1 WO 2022267801A1 CN 2022094927 W CN2022094927 W CN 2022094927W WO 2022267801 A1 WO2022267801 A1 WO 2022267801A1
Authority
WO
WIPO (PCT)
Prior art keywords
carbon atoms
group
substituted
unsubstituted
independently selected
Prior art date
Application number
PCT/CN2022/094927
Other languages
English (en)
French (fr)
Inventor
杨敏
刘云
金荣国
Original Assignee
陕西莱特光电材料股份有限公司
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by 陕西莱特光电材料股份有限公司 filed Critical 陕西莱特光电材料股份有限公司
Publication of WO2022267801A1 publication Critical patent/WO2022267801A1/zh

Links

Images

Classifications

    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
    • Y02E10/00—Energy generation through renewable energy sources
    • Y02E10/50—Photovoltaic [PV] energy
    • Y02E10/549—Organic PV cells

Definitions

  • the application belongs to the technical field of organic materials, and in particular relates to an organic compound and an organic electroluminescence device and an electronic device containing the same.
  • Organic electroluminescent diode refers to a diode in which organic light-emitting materials emit light under the action of current and electric field. It can directly convert electrical energy into light energy, and has the advantages of high brightness, fast response, wide viewing angle, simple process, and flexibility. It has a wide range of applications in the fields of high-quality flat panel display and solid-state lighting, and has attracted the attention of science and industry.
  • an organic electroluminescent device it generally includes an anode, a hole transport layer, an electroluminescent layer as an energy conversion layer, an electron transport layer and a cathode, which are stacked in sequence.
  • the two electrodes When a voltage is applied to the cathode and anode, the two electrodes generate an electric field. Under the action of the electric field, the electrons on the cathode side move to the electroluminescent layer, and the holes on the anode side also move to the electroluminescent layer. The layers are combined to form excitons, and the excitons release energy outwards in an excited state, thereby making the electroluminescent layer emit light.
  • the prior art discloses materials from which light-emitting layers can be prepared in organic electroluminescent devices. However, it is still necessary to continue to develop new materials to further improve the performance of electronic components.
  • the purpose of this application is to provide an organic compound and an organic electroluminescent device and an electronic device containing it, so as to improve material carrier mobility and energy transmission efficiency, improve the stability of molecular structure, effectively reduce device voltage and grow the device life.
  • R 1 and R 2 are the same or different from each other, and are each independently selected from hydrogen, deuterium or methyl; n is selected from 1 or 2;
  • R 3 , R 4 and R 5 are the same or different from each other, and are independently selected from hydrogen, deuterium, halogen group, cyano group, alkyl group with 1-10 carbon atoms, ring with 1-10 carbon atoms Alkyl, haloalkyl with 1-10 carbon atoms, aryl with 6-20 carbon atoms, heteroaryl with 3-20 carbon atoms;
  • n 3 represents the number of R 3 , n 3 is selected from 0, 1, 2, 3 or 4, when n 3 is greater than 1, any two R 3 are the same or different, optionally, any two adjacent R 3 forms a ring;
  • n 4 represents the number of R 4 , n 4 is selected from 0, 1 or 2, when n 4 is greater than 1, any two R 4 are the same or different, optionally, the formation of any two adjacent R 4 ring;
  • n 5 represents the number of R 5 , n 5 is selected from 0, 1, 2, 3 or 4, when n 5 is greater than 1, any two R 5 are the same or different, optionally, any two adjacent R 5 forms a ring;
  • Het is selected from nitrogen-containing heteroarylene groups with 3-30 carbon atoms
  • L 1 , L 2 , L 3 , and L are the same or different from each other, and each is independently selected from a single bond, a substituted or unsubstituted arylene group with 6-20 carbon atoms, and a substituted group with 3-30 carbon atoms. or unsubstituted heteroarylene;
  • Ar 1 and Ar 2 are independently selected from hydrogen, substituted or unsubstituted aryl groups with 6-30 carbon atoms, and substituted or unsubstituted heteroaryl groups with 3-30 carbon atoms;
  • the substituents in L 1 , L 2 , L 3 , L 4 , Ar 1 , and Ar 2 are the same or different, and are independently selected from deuterium, halogen, cyano, and C3-20 Heteroaryl, aryl with 6-20 carbon atoms, trialkylsilyl with 3-12 carbon atoms, alkyl with 1-10 carbon atoms, haloalkyl with 1-10 carbon atoms , a cycloalkyl group with 3-10 carbon atoms, a heterocycloalkyl group with 2-10 carbon atoms, and an alkoxy group with 1-10 carbon atoms.
  • an organic electroluminescence device comprising an anode and a cathode arranged oppositely, and a functional layer arranged between the anode and the cathode; the functional layer comprises the above-mentioned organic compound.
  • the functional layer includes an organic electroluminescent layer, and the organic electroluminescent layer contains the organic compound.
  • an electronic device including the above-mentioned organic electroluminescence device.
  • the organic compound of the present application has a structure formed by combining an aza electron-deficient group with an electron-rich indolocarbazole group; wherein, the aza electron-deficient group and an electron-rich indolocarbazole group It has high electron and hole injection and transport characteristics, making the molecular structure of the material bipolar, which is suitable for the light-emitting layer in organic electroluminescent devices; at the same time, the structures of indane and tetralin destroy the SP 3 hybrid structure , so that the whole structure has a large T 1 (triplet state energy level), so the stability of the molecular structure can be effectively improved on the premise of improving the carrier mobility and energy transmission efficiency of the material, thereby effectively improving the device performance.
  • T 1 triplet state energy level
  • FIG. 1 is a schematic structural view of an embodiment of an organic electroluminescent device of the present application.
  • FIG. 2 is a schematic structural diagram of an electronic device according to an embodiment of the present application.
  • Example embodiments will now be described more fully with reference to the accompanying drawings.
  • Example embodiments may, however, be embodied in many forms and should not be construed as limited to the examples set forth herein; rather, these embodiments are provided so that this application will be thorough and complete, and will fully convey the concepts of example embodiments to those skilled in the art.
  • the described features, structures, or characteristics may be combined in any suitable manner in one or more embodiments. In the following description, numerous specific details are provided in order to give a thorough understanding of the embodiments of the application.
  • R 1 and R 2 are the same or different from each other, and are each independently selected from hydrogen, deuterium or methyl; n is selected from 1 or 2;
  • R 3 , R 4 and R 5 are the same or different from each other, and are independently selected from hydrogen, deuterium, halogen group, cyano group, alkyl group with 1-10 carbon atoms, ring with 1-10 carbon atoms Alkyl, haloalkyl with 1-10 carbon atoms, aryl with 6-20 carbon atoms, heteroaryl with 3-20 carbon atoms;
  • n 3 represents the number of R 3 , n 3 is selected from 0, 1, 2, 3 or 4, when n 3 is greater than 1, any two R 3 are the same or different, optionally, any two adjacent R 3 forms a ring;
  • n 4 represents the number of R 4 , n 4 is selected from 0, 1 or 2, when n 4 is greater than 1, any two R 4 are the same or different, optionally, the formation of any two adjacent R 4 ring;
  • n 5 represents the number of R 5 , n 5 is selected from 0, 1, 2, 3 or 4, when n 5 is greater than 1, any two R 5 are the same or different, optionally, any two adjacent R 5 forms a ring;
  • Het is selected from nitrogen-containing heteroarylene groups with 3-30 carbon atoms
  • L 1 , L 2 , L 3 , and L 4 are the same or different from each other, and each is independently selected from a single bond, a substituted or unsubstituted arylene group with 6-30 carbon atoms, and an arylene group with 3-30 carbon atoms. substituted or unsubstituted heteroarylene;
  • Ar 1 and Ar 2 are independently selected from hydrogen, substituted or unsubstituted aryl groups with 6-30 carbon atoms, and substituted or unsubstituted heteroaryl groups with 3-30 carbon atoms;
  • the substituents in L 1 , L 2 , L 3 , L 4 , Ar 1 , and Ar 2 are the same or different, and are independently selected from deuterium, halogen, cyano, and C3-20 Heteroaryl, aryl with 6-20 carbon atoms, trialkylsilyl with 3-12 carbon atoms, alkyl with 1-10 carbon atoms, haloalkyl with 1-10 carbon atoms , a cycloalkyl group with 3-10 carbon atoms, a heterocycloalkyl group with 2-10 carbon atoms, and an alkoxy group with 1-10 carbon atoms.
  • the terms “optionally” and “optionally” mean that the subsequently described event or circumstance can occur but need not occur, and that the description includes instances where the event or circumstance occurs or does not occur.
  • “optionally, two adjacent substituents form a ring;” means that these two substituents may but not necessarily form a ring, including: the situation where two adjacent substituents form a ring and two phases Situations where adjacent substituents do not form a ring.
  • any adjacent substituent may include two substituents on the same atom, and may also include one substitution on two adjacent atoms. group; wherein, when there are two substituents on the same atom, the two substituents can form a saturated or unsaturated ring with the atom they are connected to; when two adjacent atoms have a substituent respectively, These two substituents may be fused to form a ring.
  • the formed ring is saturated or unsaturated with 5-13 carbon atoms Member rings, such as: benzene ring, naphthalene ring, fluorene ring, phenanthrene ring, anthracene ring, cyclopentane, cyclohexane, adamantane, etc.
  • Member rings such as: benzene ring, naphthalene ring, fluorene ring, phenanthrene ring, anthracene ring, cyclopentane, cyclohexane, adamantane, etc.
  • each...independently and “...independently” and “...independently selected from” are interchangeable, and should be understood in a broad sense, which can be It means that in different groups, the specific options expressed by the same symbols do not affect each other, and it can also mean that in the same group, the specific options expressed by the same symbols do not affect each other.
  • each q is independently 0, 1, 2 or 3
  • each R" is independently selected from hydrogen, deuterium, fluorine, chlorine", and its meaning is:
  • Formula Q-1 represents that there are q substituents R" on the benzene ring , each R" can be the same or different, and the options of each R" do not affect each other;
  • Formula Q-2 means that there are q substituents R" on each benzene ring of biphenyl, and the R on the two benzene rings The number q of "substituents may be the same or different, each R" may be the same or different, and the options of each R" do not affect each other.
  • substituted or unsubstituted means that the functional group described after the term may or may not have a substituent (hereinafter, for convenience of description, the substituent is collectively referred to as Rc).
  • substituted or unsubstituted aryl means an aryl group having a substituent Rc or an unsubstituted aryl group.
  • substituent namely Rc
  • Rc can be, for example, deuterium, halogen, cyano, heteroaryl with 3-20 carbon atoms, aryl with 6-20 carbon atoms, and alkyl with 1-10 carbon atoms , a haloalkyl group with 1-10 carbon atoms, a cycloalkyl group with 3-10 carbon atoms, an alkoxy group with 1-10 carbon atoms, and a trialkylsilyl group with 3-12 carbon atoms,
  • any two of the substituents are connected to each other to form a 3-15 membered saturated or unsaturated ring together with the atoms to which they are connected.
  • the "substituted" functional group can be substituted by one or more than two substituents in the above Rc; when two substituents Rc are connected to the same atom, these two substituents Rc can be independently exist or connect with each other to form a ring with the atom; when there are two adjacent substituents Rc on the functional group, the two adjacent substituents Rc can exist independently or be fused with the functional group to which they are attached to form a ring.
  • the number of carbon atoms of a substituted or unsubstituted functional group refers to the number of all carbon atoms. For example, if L is selected from a substituted arylene group with 12 carbon atoms, all the carbon atoms of the arylene group and its substituents are 12. For example: Ar is Then its carbon number is 10; L is Its carbon number is 12.
  • hetero refers to including at least one heteroatom such as B, N, O, S, P, Si or Se in a functional group and the remaining atoms are carbon and hydrogen .
  • alkyl may include straight chain alkyl or branched chain alkyl.
  • the alkyl group may have 1 to 10 carbon atoms, and in the present application, a numerical range such as “1 to 10" refers to each integer in the given range; for example, “1 to 10 carbon atoms” means that may contain 1 Alkanes of 1 carbon atom, 2 carbon atoms, 3 carbon atoms, 4 carbon atoms, 5 carbon atoms, 6 carbon atoms, 7 carbon atoms, 8 carbon atoms, 9 carbon atoms, 10 carbon atoms base.
  • the alkyl group is selected from alkyl groups with 1-5 carbon atoms, and specific examples include, but are not limited to, methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, sec-butyl , tert-butyl and amyl.
  • aryl refers to an optional functional group or substituent derived from an aromatic carbocycle.
  • the aryl group can be a single-ring aryl group (such as phenyl) or a polycyclic aryl group, in other words, the aryl group can be a single-ring aryl group, a condensed ring aryl group, two or more single-ring aryl groups connected by carbon-carbon bond conjugation. Cyclic aryl groups, single-ring aryl groups and condensed-ring aryl groups connected through carbon-carbon bond conjugation, and two or more fused-ring aryl groups connected through carbon-carbon bond conjugation.
  • the fused ring aryl group may include, for example, a bicyclic fused aryl group (such as naphthyl), a tricyclic fused aryl group (such as a phenanthrenyl, a fluorenyl, anthracenyl) and the like.
  • aryl groups may include, but are not limited to, phenyl, naphthyl, fluorenyl, anthracenyl, phenanthrenyl, biphenyl, terphenyl, quaterphenyl, pentphenyl, benzo[9,10] phenanthrenyl, pyrenyl, benzofluoranthene, Base etc.
  • the "substituted or unsubstituted aryl group" in the present application may contain 6-30 carbon atoms, and in some embodiments, the number of carbon atoms in the substituted or unsubstituted aryl group may be 6-12.
  • the number of carbon atoms in the aryl group can be 6, 12, 13, 14, 15, 18, or 20. Of course, the number of carbon atoms can also be other numbers, which will not be listed here.
  • biphenyl can be understood as a phenyl-substituted aryl group, or as an unsubstituted aryl group.
  • the arylene group referred to refers to a divalent group formed by further losing a hydrogen atom from an aryl group.
  • the substituted aryl group can be that one or more than two hydrogen atoms in the aryl group are replaced by such as deuterium atom, halogen group, cyano group, tert-butyl group, trifluoromethyl group, heteroaryl group, trimethyl group, etc. Silicon group, alkyl group, cycloalkyl group, alkoxy group, alkylthio group and other groups are substituted.
  • the number of carbon atoms of a substituted aryl group refers to the total number of carbon atoms of the aryl group and the substituent on the aryl group, for example, a substituted aryl group with 18 carbon atoms refers to the aryl group and its The total number of carbon atoms in the substituents is 18.
  • aryl as a substituent include, but are not limited to: phenyl, naphthyl, anthracenyl, phenanthrenyl, fluorenyl, biphenyl and the like.
  • heteroaryl refers to a monovalent aromatic ring or its derivatives containing 1, 2, 3, 4, 5, 6 or 7 heteroatoms in the ring, and the heteroatoms can be B, O, N, At least one of P, Si, Se and S.
  • the heteroaryl group can be a monocyclic heteroaryl group or a polycyclic heteroaryl group, in other words, a heteroaryl group can be a single aromatic ring system, or a plurality of aromatic ring systems connected by carbon-carbon bond conjugation, and any aromatic
  • the ring system is an aromatic single ring or an aromatic fused ring.
  • heteroaryl groups may include thienyl, furyl, pyrrolyl, imidazolyl, thiazolyl, oxazolyl, oxadiazolyl, triazolyl, pyridyl, bipyridyl, pyrimidyl, triazinyl, Acridyl, pyridazinyl, pyrazinyl, quinolinyl, quinazolinyl, quinoxalinyl, phenoxazinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyridine Azinyl, isoquinolyl, indolyl, carbazolyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothienyl, dibenzothienyl, thiophene Thienyl, benzofuryl, phen
  • thienyl, furyl, phenanthrolinyl, etc. are heteroaryl groups of a single aromatic ring system type
  • N-arylcarbazolyl and N-heteroarylcarbazolyl are polycarbonate groups linked by carbon-carbon bonds.
  • ring system type heteroaryl The "substituted or unsubstituted heteroaryl" of the present application may contain 3-30 carbon atoms, and in some embodiments, the number of carbon atoms in the substituted or unsubstituted heteroaryl may be 12-20.
  • the number of carbon atoms may be 3, 4, 5, 7, 12, 13, 15, 18, or 20.
  • the number of carbon atoms may also be other numbers, which will not be listed here.
  • the heteroarylene referred to refers to a polyvalent group formed by the further loss of one or more hydrogen atoms from the heteroaryl group.
  • the substituted heteroaryl group can be one or more than two hydrogen atoms in the heteroaryl group replaced by such as a deuterium atom, a halogen group, a cyano group, an aryl group, a heteroaryl group, a trimethylsilyl group, an alkane group, etc.
  • Substituted by groups such as radicals, cycloalkyls, alkoxyls, and alkylthio groups. It should be understood that the number of carbon atoms in a substituted heteroaryl group refers to the total number of carbon atoms in the heteroaryl group and the substituents on the heteroaryl group.
  • heteroaryl as a substituent include, but are not limited to: pyridyl, carbazolyl, dibenzofuryl, and dibenzothienyl.
  • the halogen group may include fluorine, iodine, bromine, chlorine and the like.
  • Ring in the present application includes saturated ring, unsaturated ring; saturated ring means cycloalkyl, heterocycloalkyl; unsaturated ring means cycloalkenyl, heterocycloalkenyl, aryl and heteroaryl.
  • a non-positioning linkage refers to a single bond protruding from the ring system It means that one end of the link can be connected to any position in the ring system that the bond runs through, and the other end is connected to the rest of the compound molecule.
  • the naphthyl group represented by the formula (f) is connected to other positions of the molecule through two unpositioned linkages that run through the bicyclic ring, and the meanings represented include the formula (f -1) to any possible connection shown in formula (f-10).
  • the dibenzofuryl group represented by the formula (X') is connected to other positions of the molecule through an unpositioned link extending from the middle of a benzene ring on one side,
  • the meaning represented by it includes any possible connection mode shown in formula (X'-1) to formula (X'-4).
  • the chemical formula 1 has a structure shown in any one of formulas A to F:
  • R 3 , R 4 and R 5 are the same or different from each other, and are independently selected from hydrogen, deuterium, fluorine, cyano, alkyl with 1-5 carbon atoms, carbon Aryl groups with 6-12 atoms and heteroaryl groups with 3-12 carbon atoms;
  • any two adjacent R 3 form a saturated or unsaturated ring with 3-15 carbon atoms
  • any two adjacent R 4 form a saturated or unsaturated ring with 3-15 carbon atoms ring
  • any two adjacent R 5 form a saturated or unsaturated ring with 3-15 carbon atoms.
  • any two adjacent R3s form a benzene ring.
  • any two adjacent R 4 form a benzene ring.
  • any two adjacent R 5 form a benzene ring.
  • n is selected from 1, and both R 1 and R 2 are selected from hydrogen.
  • n is selected from 1, and both R 1 and R 2 are selected from methyl.
  • n is selected from 1, R 1 is selected from hydrogen, and R 2 is selected from methyl.
  • n is selected from 2, and both R 1 and R 2 are selected from hydrogen.
  • n is selected from 2, and R 1 and R 2 are both selected from methyl.
  • n is selected from 2
  • R 1 is selected from hydrogen
  • R 2 is selected from methyl
  • n is selected from 2
  • R 1 is selected from methyl
  • R 2 is selected from hydrogen
  • the Het is selected from nitrogen-containing heteroarylene groups with 3-12 carbon atoms.
  • the Het is selected from triazinylene, pyrimidinylene, quinazolinylene, quinoxalinylene, benzoxazolene, benzothiazolyl or the following Group:
  • Het has only two linkages, which means that the position is connected And L2 is a single bond and Ar2 is hydrogen .
  • the Het is selected from the group consisting of the following groups:
  • said L 1 , L 2 , L 3 , and L 4 are the same or different from each other, and are independently selected from single bonds, substituted or unsubstituted ones with 6-12 carbon atoms an arylene group, a substituted or unsubstituted heteroarylene group having 12 carbon atoms.
  • said L 1 , L 2 , L 3 , and L 4 are the same or different from each other, and are each independently selected from a single bond, substituted or unsubstituted phenylene, substituted or unsubstituted biphenylene, Substituted or unsubstituted naphthylene, substituted or unsubstituted carbazolyl;
  • the substituents in L 1 , L 2 , L 3 , and L 4 are the same or different from each other, and are independently selected from deuterium, halogen, cyano, and alkane with 1-5 carbon atoms base or phenyl.
  • the substituents in L 1 , L 2 , L 3 , and L 4 are the same or different from each other, and are each independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl base or phenyl.
  • the L 1 , L 2 , L 3 , and L 4 are the same or different from each other, and are each independently selected from a single bond, substituted or unsubstituted group V; wherein, the unsubstituted The group V is selected from the group consisting of:
  • the substituted group V has one or more substituents, each of which is independently selected from: deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, phenyl; When the number of substituents of V is greater than 1, each substituent is the same or different.
  • the L 1 , L 2 , L 3 , and L 4 are each independently selected from a single bond or the group consisting of the following groups:
  • the Ar 1 and Ar 2 are independently selected from hydrogen, substituted or unsubstituted aryl groups with 6-20 carbon atoms, substituted or unsubstituted aryl groups with 12-20 carbon atoms Substituted heteroaryl;
  • the substituents in Ar 1 and Ar 2 are independently selected from deuterium, halogen groups, cyano groups, alkyl groups with 1-5 carbon atoms, and aryl groups with 6-12 carbon atoms .
  • the substituents in Ar 1 and Ar 2 are independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl or phenyl.
  • the Ar 1 and Ar 2 are independently selected from hydrogen, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted dibenzofuryl, substituted or unsubstituted dibenzothienyl, substituted or unsubstituted carbazolyl, or substituted or unsubstituted fluorenyl.
  • Ar is selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted dibenzofuryl, substituted or unsubstituted di Benzothienyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted fluorenyl;
  • Ar is selected from hydrogen , substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted dibenzofuryl, substituted or unsubstituted dibenzo Thienyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted fluorenyl.
  • the Ar 1 and Ar 2 are independently selected from hydrogen, substituted or unsubstituted group W; wherein, the unsubstituted group W is selected from the group consisting of the following groups:
  • substituents in Ar 1 and Ar 2 are independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl or phenyl.
  • the Ar 1 and Ar 2 are independently selected from the group consisting of hydrogen or the following groups:
  • the organic compound is selected from the group consisting of the following compounds:
  • the present application also provides an organic electroluminescent device for realizing photoelectric conversion or electro-optic conversion.
  • the organic electroluminescent device includes an anode and a cathode oppositely arranged, and at least one functional layer between the anode and the cathode, and the functional layer contains the organic compound of the application.
  • the organic electroluminescent device of the present application includes an anode 100, a cathode 200, and at least one functional layer 300 between the anode layer and the cathode layer.
  • the functional layer 300 includes a hole injection layer 310, a hole transport layer 320, a hole auxiliary layer 330, an organic electroluminescence layer 340, an electron transport layer 350, and an electron injection layer 360; the hole injection layer 310, the hole transport layer 320 , the hole auxiliary layer 330, the organic electroluminescent layer 340, the electron transport layer 350 and the electron injection layer 360 can be sequentially formed on the anode 100, and the organic electroluminescent layer 340 can contain the organic compound described in the first aspect of the present application, It is preferable to contain at least one of the compounds A1-A252, B1-B188, C1-C88, D1-D76, F1-F32, G1-G24, H1-H24, I1-I56.
  • an organic electroluminescent device includes an anode 100 and a cathode 200 disposed opposite to each other, and a functional layer 300 disposed between the anode 100 and the cathode 200 ; the functional layer 300 includes the organic compound provided in this application.
  • the organic compound provided by the present application can be used to form at least one organic thin layer in the functional layer 300, so as to improve the lifetime characteristics, efficiency characteristics and reduce the driving voltage of the organic electroluminescent device; in some embodiments , can also improve the electrochemical stability and thermal stability of the organic electroluminescent device, and improve the performance uniformity of the mass-produced organic electroluminescent device.
  • the anode 100 includes the following anode material, which is preferably a material with a large work function (work function) that facilitates hole injection into the functional layer.
  • anode materials include: metals such as nickel, platinum, vanadium, chromium, copper, zinc and gold or their alloys; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO) and indium zinc oxide (IZO); Combined metals and oxides such as ZnO:Al or SnO 2 :Sb; or conducting polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene ](PEDT), polypyrrole and polyaniline, but not limited thereto. It preferably includes a transparent electrode comprising indium tin oxide (ITO) as an anode.
  • ITO indium tin oxide
  • the hole transport layer 320 may include one or more hole transport materials.
  • the material of the hole transport layer is selected from carbazole polymer compounds and carbazole-linked triarylamine compounds, which are not specifically limited in this application.
  • the hole transport layer 320 may be composed of TPAC.
  • a hole injection layer 310 may also be provided between the anode 100 and the hole transport layer 320 to enhance the ability to inject holes into the hole transport layer 320 .
  • the hole injection layer 310 can be selected from benzidine derivatives, starburst arylamine compounds, phthalocyanine derivatives or other materials, which are not particularly limited in this application.
  • the hole injection layer 310 is composed of F4-TCNQ.
  • the hole assisting layer 330 may be selected from carbazole polymers, carbazole-linked triarylamine compounds or other materials, which are not particularly limited in this application.
  • the hole assisting layer 330 is composed of HT-01.
  • the organic electroluminescent layer 340 may include the organic compound provided in this application, and may also include other organic electroluminescent layer materials, which are not specifically limited in this application.
  • the organic electroluminescent layer 340 is made of the organic compound provided by the application, GH-P and Ir(3mppy) 3 or by RH-P, the organic compound provided by the application , Ir(dmpq) 2 acac composition.
  • the organic electroluminescent device is a green organic electroluminescent device
  • the organic electroluminescent layer 340 includes the organic compound described in the present application, GH-P and the guest material Ir(3mppy) 3 .
  • the organic electroluminescent device is a red organic electroluminescent device
  • the organic electroluminescent layer 340 comprises the organic compound described in the present application, RH-P and the guest material Ir(dmpq) 2 acac.
  • the electron transport layer 350 can be a single-layer structure or a multilayer structure, which can include one or more electron transport materials, and the electron transport material can be selected from benzimidazole derivatives, oxadiazole derivatives, quinoxaline Derivatives or other electron transport materials, the present application does not make special limitations on this.
  • the electron transport layer 350 may be composed of BCP and LiQ.
  • the cathode 200 includes a cathode material that is a material with a small work function that facilitates injection of electrons into the functional layer.
  • cathode materials include: metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead or alloys thereof; or multilayer materials such as LiF/Al, Liq/ Al, LiO 2 /Al, LiF/Ca, LiF/Al, and BaF 2 /Ca, but not limited thereto.
  • a metal electrode including magnesium and silver is preferably included as the cathode 200 .
  • an electron injection layer 360 may also be provided between the cathode 200 and the electron transport layer 350 to enhance the ability to inject electrons into the electron transport layer 350 .
  • the electron injection layer 360 may include inorganic materials such as alkali metal sulfides and alkali metal halides, or may include complexes of alkali metals and organic compounds.
  • the electron injection layer 360 is Yb.
  • the present application also provides an electronic device, which includes the electronic component described in the present application.
  • the electronic device provided in this application is a first electronic device 400
  • the first electronic device 400 includes any organic electroluminescent device described in the above organic electroluminescent device implementation.
  • the electronic device may be a display device, a lighting device, an optical communication device or other types of electronic devices, such as but not limited to computer screens, mobile phone screens, televisions, electronic paper, emergency lights, optical modules, etc. Since the first electronic device 400 has the above-mentioned organic electroluminescent device, it has the same beneficial effects, and the present application will not repeat them here.
  • IM-i1 (10.0g; 37.4mmol), SM-B (8.7g; 37.4mmol), tetrakistriphenylphosphine palladium (0.43g; 0.37mmol), potassium carbonate (15.5g; 112.3mmol), tetrabutyl Ammonium bromide (0.12g; 0.37mmol), toluene (240mL), water (60mL), and ethanol (60mL) were added to a round-bottomed flask; under nitrogen protection, the temperature was raised to 110°C and stirred for 6 hours; cooled to room temperature, The reaction solution was washed with water and then separated, the organic phase was dried with anhydrous magnesium sulfate, and then the solvent was removed under reduced pressure to obtain the crude product; the crude product was purified by silica gel column chromatography using dichloromethane/n-heptane as the eluent to obtain IM- e1 (9.82 g; 70% yield).
  • IM-i1 (10.0g; 37.4mmol), indolo[2,3-a]carbazole (9.59g; 37.4mmol), tris(dibenzylideneacetone)dipalladium (0.34g; 0.37mmol), Tri-tert-butylphosphine (0.15g; 0.75mmol), sodium tert-butoxide (5.39g; 56.1mmol) and xylene (100mL) were added into a round bottom flask; under nitrogen protection, heated to 140°C and stirred for 10 hours ; down to room temperature, the reaction solution was washed with water and separated, the organic phase was dried with anhydrous magnesium sulfate, and the solvent was removed under reduced pressure to obtain the crude product; the crude product was purified by silica gel column chromatography with dichloromethane/n-heptane as the eluent, IM-a1 was obtained (10.3 g; yield 62%).
  • the anode is formed with indium tin oxide (ITO) on the substrate on which the reflective layer is formed, with a thickness of Cut into a size of 40mm ⁇ 40mm ⁇ 0.7mm, and prepare it into an experimental substrate with cathode, anode and insulating layer patterns by photolithography process, and clean the surface of ITO substrate with organic solvent to remove impurities on the surface; or use ultraviolet Ozone and O 2 : N 2 plasma surface treatment to increase the work function of the anode.
  • ITO indium tin oxide
  • F4-TCNQ is vacuum evaporated by PVD method to form a thickness of The hole injection layer, and evaporated on the hole injection layer
  • the TPAC forms the hole transport layer.
  • the compound A-2: GH-P: Ir(3mppy) 3 is co-evaporated at a ratio of 45%: 45%: 10% (evaporation rate) to form a thickness of Organic electroluminescent layer (green emitting layer).
  • Evaporate BCP and LiQ at a weight ratio of 1:1 to form Thick electron transport layer Yb is vapor-deposited on the electron transport layer to form a thickness of Electron injection layer, magnesium and silver are co-evaporated on the electron injection layer with an evaporation ratio of 1:9 to form a thickness of of the cathode.
  • the CP-02 forms an organic capping layer (CPL), thereby realizing the preparation of organic light-emitting devices.
  • Embodiment 2 ⁇ 37
  • An organic electroluminescent device was prepared by the same method as Device Example 1 except that Compound 1 was used when forming the green light emitting layer.
  • An organic electroluminescent device was fabricated by the same method as Device Example 1, except that compound 2 was used when forming the green light emitting layer.
  • An organic electroluminescent device was fabricated by the same method as Device Example 1, except that compound 3 was used when forming the green light-emitting layer.
  • An organic electroluminescent device was fabricated by the same method as Device Example 1 except that compound 4 was used when forming the green light emitting layer.
  • Table 5 shows the material structures used in device embodiments 1-37 and comparative examples 1-4.
  • the organic compound of the present application is used as the electronic host material of the mixed host of the organic electroluminescent layer in the device embodiments 1 to 37.
  • the current efficiency is at least 14.3%
  • the power efficiency is 14.3%.
  • the substrate was cut into a size of 40mm ⁇ 40mm ⁇ 0.7mm, and it was prepared into an experimental substrate with cathode, anode and insulating layer patterns by photolithography process, and the surface was treated with ultraviolet ozone and O 2 :N 2 plasma to remove surface particles and improve the anode work function.
  • F4-TCNQ is vacuum-evaporated on the substrate by PVD method to form a thickness of The hole injection layer, and TPAC is vapor-deposited on the hole injection layer to form a thickness of hole transport layer.
  • the thickness of evaporation on the hole transport layer is HT-01, forming a hole assisting layer.
  • compound RH-P compound I-22: Ir(dmpq) 2 acac is co-evaporated at a ratio of 49%: 49%: 2% (evaporation rate), forming a thickness of The organic electroluminescent layer (red emitting layer).
  • BCP and LiQ were mixed at a weight ratio of 1:1 and evaporated to form Thick electron transport layer, Yb is evaporated on the electron transport layer to form The electron injection layer, and then magnesium and silver are vacuum evaporated on the electron injection layer at the evaporation rate of 1:10 to form of the cathode.
  • CP-01 Evaporated on the above cathode
  • the thickness of CP-01 forms an organic cover layer (CPL) to complete the manufacture of organic light-emitting devices.
  • CPL organic cover layer
  • Example 7 When forming the red light-emitting layer, the compounds shown in Table 7 were used instead of compound I-22 in Example 1, and an organic electroluminescent device was fabricated by the same method as in Example 38.
  • an organic electroluminescent device was prepared in the same manner as in Example 38 by substituting Compound 5 for Compound I-22 in Example 1.
  • Example 7 compound 6 was used instead of compound I-22 in Example 1, and an organic electroluminescent device was prepared in the same manner as in Example 38.
  • the organic compound of the present application has a structure formed by combining an aza electron-deficient group with an electron-rich indolocarbazole group; wherein, the aza electron-deficient group and an electron-rich indolocarbazole group It has high electron and hole injection and transport characteristics, making the molecular structure of the material bipolar, which is suitable for the light-emitting layer in organic electroluminescent devices; at the same time, the structures of indane and tetralin destroy the SP 3 hybrid structure , so that the whole structure has a large T 1 (triplet state energy level), so the stability of the molecular structure can be effectively improved on the premise of improving the carrier mobility and energy transmission efficiency of the material, thereby effectively improving the device performance.
  • T 1 triplet state energy level

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Electroluminescent Light Sources (AREA)

Abstract

本申请涉及一种有机化合物以及包含该有机化合物的有机电致发光器件和包含该有机电致发光器件的电子装置。本申请的有机化合物的结构如化学式1表示，将该有机化合物应用于有机电致发光器件中，可显著改善器件的性能。

Description

一种有机化合物及包含其的有机电致发光器件和电子装置
本申请要求在2021年06月21日提交中国国家知识产权局、申请号为202110688704.2的中国专利申请的优先权，其全部内容通过引用结合在本公开中。
技术领域
本申请属于有机材料技术领域，尤其涉及一种有机化合物及包含其的有机电致发光器件和电子装置。
背景技术
随着电子技术的发展和材料科学的进步，用于实现电致发光或者光电转化的电子器件的应用范围越来越广泛。有机电致发光二极管是指有机发光材料在电流和电场的作用下发光的二极管，其能够将电能直接转化为光能，具有亮度高、响应快、视角宽、工艺简单、可柔性等优点，因而在高质量的平板显示以及固体照明等领域具有广泛的应用，且已经吸引了科学和工业等各界的关注。在有机电致发光器件中，其一般包括依次层叠设置的阳极、空穴传输层、作为能量转化层的电致发光层、电子传输层和阴极。当阴阳两极施加电压时，两电极产生电场，在电场的作用下，阴极侧的电子向电致发光层移动，阳极侧的空穴也向电致发光层移动，电子和空穴在电致发光层结合形成激子，激子处于激发态向外释放能量，进而使得电致发光层对外发光。
现有技术中公开了可以在有机电致发光器件中制备发光层的材料。然而，依然有必要继续研发新型的材料，以进一步提高电子元器件的性能。
发明内容
本申请的目的在于提供一种有机化合物及包含其的有机电致发光器件和电子装置，以提升材料载流子迁移率和能量传输效率、提升分子结构的稳定性、有效降低器件电压并增长器件寿命。
为实现上述发明目的，本申请采用如下技术方案：
根据本申请的第一个方面，提供一种有机化合物，其具有如化学式1表示的结构：
Figure PCTCN2022094927-appb-000001
其中，
各R 1和R 2彼此相同或不同，且各自独立地选自氢、氘或甲基；n选自1或者2；
R 3、R 4和R 5彼此相同或不同，且各自独立地选自氢、氘、卤素基团、氰基、碳原子数为1-10的烷基、碳原子数为1-10的环烷基、碳原子数为1-10的卤代烷基、碳原子数为6-20的芳基、碳原子数为3-20的杂芳基；
n 3表示R 3的个数，n 3选自0、1、2、3或4，当n 3大于1时，任意两个R 3相同或者不相同，任选地，任意两个相邻的R 3形成环；
n 4表示R 4的个数，n 4选自0、1或2，当n 4大于1时，任意两个R 4相同或者不相同，任选地，任意两个相邻的R 4的形成环；
n 5表示R 5的个数，n 5选自0、1、2、3或4，当n 5大于1时，任意两个R 5相同或者不相同，任选地，任意两个相邻的R 5形成环；
Het选自碳原子数为3-30的含氮亚杂芳基；
L 1、L 2、L 3、L彼此相同或不同，且各自独立地选自单键、碳原子数为6-20的取代或未取代的亚芳基、碳原子数为3-30的取代或未取代的亚杂芳基；
Ar 1，Ar 2分别独立地选自氢、碳原子数为6-30的取代或未取代的芳基、碳原子数为3-30的取代或未取代的杂芳基；
所述L 1、L 2、L 3、L 4、Ar 1、Ar 2中的取代基相同或不同，且分别独立地选自氘、卤素基团、氰基、碳原子数为3-20的杂芳基、碳原子数为6-20的芳基、碳原子数为3-12的三烷基硅基、碳原子数为1-10的烷基、碳原子数为1-10的卤代烷基、碳原子数为3-10的环烷基、碳原子数为2-10的杂环烷基、碳原子数为1-10的烷氧基。
根据本申请的第二个方面，提供一种有机电致发光器件，包括相对设置的阳极和阴极，以及设于所述阳极和所述阴极之间的功能层；所述功能层包含上述的有机化合物。按照本申请的一种实施方式，所述功能层包括有机电致发光层，所述有机电致发光层包含所述的有机化合物。
根据本申请的第三个方面，提供了一种电子装置，包括上述的有机电致发光器件。
本申请的有机化合物具有以氮杂缺电子基团与富电子基团吲哚并咔唑相结合而成的结构；其中，氮杂缺电子基团与富电子的吲哚并咔唑的基团分别具有高的电子和空穴注入传输特性，使得材料分子结构具有双极性，适用于有机电致发光器件中的发光层；同时，二氢化茚、四氢化萘结构破坏了SP 3杂化结构，使得整个结构具有大的T 1(三线态能级)，因而可以在提升材料载流子迁移率和能量传输效率的前提下，有效提升分子结构的稳定性，从而有效改善器件性能。
附图说明
附图是用来提供对本申请的进一步理解，并且构成说明书的一部分，与下面的具体实施方式一起用于解释本申请，但并不构成对本申请的限制。
在附图中：
图1是本申请的有机电致发光器件的一实施方式的结构示意图。
图2是本申请一实施方式的电子装置的结构示意图。
附图标记说明
100、阳极；200、阴极；300、功能层；310、空穴注入层；320、空穴传输层；330、空穴辅助层；340、有机电致发光层；350、电子传输层；360、电子注入层；400、电子装置。
具体实施方式
现在将参考附图更全面地描述示例实施例。然而，示例实施例能够以多种形式实施，且不应被理解为限于在此阐述的范例；相反，提供这些实施例使得本申请将更加全面和完整，并将示例实施例的构思全面地传达给本领域的技术人员。所描述的特征、结构或特性可以以任何合适的方式结合在一个或更多实施例中。在下面的描述中，提供许多具体细节从而给出对本申请的实施例的充分理解。
在图中，为了清晰，可能夸大了区域和层的厚度。在图中相同的附图标记表示相同或类似的结构，因而将省略它们的详细描述。
所描述的特征、结构或特性可以以任何合适的方式结合在一个或更多实施例中。在下面的描述中，提供许多具体细节从而给出对本申请的实施例的充分理解。然而，本领域技术人员将意识到，可以实践本申请的技术方案而没有所述特定细节中的一个或更多，或者可以采用其它的方法、组元、材料等。在其它情况下，不详细示出或描述公知结构、材料或者操作以避免模糊本申请的主要技术创意。
本申请提供一种有机化合物，其具有如化学式1表示的结构：
Figure PCTCN2022094927-appb-000002
其中，
各R 1和R 2彼此相同或不同，且各自独立地选自氢、氘或甲基；n选自1或者2；
R 3、R 4和R 5彼此相同或不同，且各自独立地选自氢、氘、卤素基团、氰基、碳原子数为1-10的烷基、碳原子数为1-10的环烷基、碳原子数为1-10的卤代烷基、碳原子数为6-20的芳基、碳原子数为3-20的杂芳基；
n 3表示R 3的个数，n 3选自0、1、2、3或4，当n 3大于1时，任意两个R 3相同或者不相同，任选地，任意两个相邻的R 3形成环；
n 4表示R 4的个数，n 4选自0、1或2，当n 4大于1时，任意两个R 4相同或者不相同，任选地，任意两个相邻的R 4的形成环；
n 5表示R 5的个数，n 5选自0、1、2、3或4，当n 5大于1时，任意两个R 5相同或者不相同，任选地，任意两个相邻的R 5形成环；
Het选自碳原子数为3-30的含氮亚杂芳基；
L 1、L 2、L 3、L 4彼此相同或不同，且各自独立地选自单键、碳原子数为6-30的取代或未取代的亚芳基、碳原子数为3-30的取代或未取代的亚杂芳基；
Ar 1，Ar 2分别独立地选自氢、碳原子数为6-30的取代或未取代的芳基、碳原子数为3-30的取代或未取代的杂芳基；
所述L 1、L 2、L 3、L 4、Ar 1、Ar 2中的取代基相同或不同，且分别独立地选自氘、卤素基团、氰基、碳原子数为3-20的杂芳基、碳原子数为6-20的芳基、碳原子数为3-12的三烷基硅基、碳原子数为1-10 的烷基、碳原子数为1-10的卤代烷基、碳原子数为3-10的环烷基、碳原子数为2-10的杂环烷基、碳原子数为1-10的烷氧基。
在本申请中，术语“任选”、“任选地”意味着随后所描述的事件或者环境可以发生但不是必须发生，该说明包括该事情或者环境发生或者不发生的场合。例如，“任选地，两个相邻取代基形成环；”意味着这两个取代基可以形成环但不是必须形成环，包括：两个相邻的取代基形成环的情景和两个相邻的取代基不形成环的情景。
在本申请中，“任意两个相邻的取代基形成环”中，“任意相邻”可以包括同一个原子上具有两个取代基，还可以包括两个相邻的原子上分别具有一个取代基；其中，当同一个原子上具有两个取代基时，两个取代基可以与其共同连接的该原子形成饱和或不饱和的环；当两个相邻的原子上分别具有一个取代基时，这两个取代基可以稠合成环。举例而言，当Ar 1中有2个或2个以上的取代基，且任意两个相邻的取代基形成环时，所成的环为饱和或不饱和的碳原子数为5-13的元环，例如：苯环、萘环、芴环、菲环、蒽环、环戊烷、环己烷、金刚烷等等。
在本申请中，所采用的描述方式“各……独立地为”与“……分别独立地为”和“……独立地选自”可以互换，均应做广义理解，其既可以是指在不同基团中，相同符号之间所表达的具体选项之间互相不影响，也可以表示在相同的基团中，相同符号之间所表达的具体选项之间互相不影响。例如，“
Figure PCTCN2022094927-appb-000003
其中，各q独立地为0、1、2或3，各R”独立地选自氢、氘、氟、氯”，其含义是：式Q-1表示苯环上有q个取代基R”，各个R”可以相同也可以不同，每个R”的选项之间互不影响；式Q-2表示联苯的每一个苯环上有q个取代基R”，两个苯环上的R”取代基的个数q可以相同或不同，各个R”可以相同也可以不同，每个R”的选项之间互不影响。
在本申请中，“取代或未取代的”这样的术语是指，在该术语后面记载的官能团可以具有或不具有取代基(下文为了便于描述，将取代基统称为Rc)。例如，“取代或未取代的芳基”是指具有取代基Rc的芳基或者非取代的芳基。其中上述的取代基即Rc例如可以为氘、卤素、氰基、碳原子数为3-20的杂芳基、碳原子数为6-20的芳基、碳原子数为1-10的烷基、碳原子数为1-10的卤代烷基、碳原子数为3-10的环烷基、碳原子数为1-10的烷氧基、碳原子数为3-12的三烷基硅基，任选地，任意两个所述取代基相互连接以与它们所连接的原子一起形成3-15元的饱和或不饱和环。在本申请中，“取代的”官能团可以被上述Rc中的1个或2个以上的取代基取代；当同一个原子上连接有两个取代基Rc时，这两个取代基Rc可以独立地存在或者相互连接以与所述原子形成环；当官能团上存在两个相邻的取代基Rc时，相邻的两个取代基Rc可以独立地存在或者与其所连接的官能团稠合成环。
在本申请中，取代或未取代的官能团的碳原子数，指的是所有碳原子数。举例而言，若L选自取代的碳原子数为12的亚芳基，则亚芳基及其上的取代基的所有碳原子数为12。例如：Ar为
Figure PCTCN2022094927-appb-000004
则其碳原子数为10；L为
Figure PCTCN2022094927-appb-000005
其碳原子数为12。
在本申请中，当没有另外提供具体的定义时，“杂”是指在一个官能团中包括至少1个B、N、O、S、P、Si或Se等杂原子且其余原子为碳和氢。
在本申请中，“烷基”可以包括直链烷基或支链烷基。烷基可具有1至10个碳原子，在本申请中，诸如“1至10”的数值范围是指给定范围中的各个整数；例如，“1至10个碳原子”是指可包含1个碳原 子、2个碳原子、3个碳原子、4个碳原子、5个碳原子、6个碳原子、7个碳原子、8个碳原子、9个碳原子、10个碳原子的烷基。
优选地，烷基选自碳原子数为1-5的烷基，具体施例包括但不限于，甲基、乙基、丙基、异丙基、正丁基、异丁基、仲丁基、叔丁基和戊基。
在本申请中，芳基指的是衍生自芳香碳环的任选官能团或取代基。芳基可以是单环芳基(例如苯基)或多环芳基，换言之，芳基可以是单环芳基、稠环芳基、通过碳碳键共轭连接的两个或者更多个单环芳基、通过碳碳键共轭连接的单环芳基和稠环芳基、通过碳碳键共轭连接的两个或者更多个稠环芳基。即，除非另有说明，通过碳碳键共轭连接的两个或者更多个芳香基团也可以视为本申请的芳基。其中，稠环芳基例如可以包括双环稠合芳基(例如萘基)、三环稠合芳基(例如菲基、芴基、蒽基)等。芳基的实例可以包括但不限于，苯基、萘基、芴基、蒽基、菲基、联苯基、三联苯基、四联苯基、五联苯基、苯并[9,10]菲基、芘基、苯并荧蒽基、
Figure PCTCN2022094927-appb-000006
基等。本申请的“取代或未取代的芳基”可含有6-30个碳原子，在一些实施例中，取代或未取代的芳基中的碳原子数可以是6-12。举例而言，本申请中，芳基的碳原子数量可以是6、12、13、14、15、18、20，当然，碳原子数还可以是其他数量，在此不再一一列举。在本申请中，联苯基可以理解为苯基取代的芳基，也可以理解为未取代的芳基。
在本申请中，涉及的亚芳基是指芳基进一步失去一个氢原子所形成的二价基团。
在本申请中，取代的芳基可以是芳基中的一个或者两个以上氢原子被诸如氘原子、卤素基团、氰基、叔丁基、三氟甲基、杂芳基、三甲基硅基、烷基、环烷基、烷氧基、烷硫基等基团取代。应当理解地是，取代的芳基的碳原子数，指的是芳基和芳基上的取代基的碳原子总数，例如碳原子数为18的取代的芳基，指的是芳基及其取代基的总碳原子数为18。
在本申请中，作为取代基的芳基，具体实例包括但不限于：苯基、萘基、蒽基、菲基、芴基、联苯基等等。
在本申请中，杂芳基是指环中包含1、2、3、4、5、6或7个杂原子的一价芳香环或其衍生物，所述杂原子可以是B、O、N、P、Si、Se和S中的至少一种。杂芳基可以是单环杂芳基或多环杂芳基，换言之，杂芳基可以是单个芳香环体系，也可以是通过碳碳键共轭连接的多个芳香环体系，且任一芳香环体系为一个芳香单环或者一个芳香稠环。示例地，杂芳基可以包括噻吩基、呋喃基、吡咯基、咪唑基、噻唑基、噁唑基、噁二唑基、三唑基、吡啶基、联吡啶基、嘧啶基、三嗪基、吖啶基、哒嗪基、吡嗪基、喹啉基、喹唑啉基、喹喔啉基、吩噁嗪基、酞嗪基、吡啶并嘧啶基、吡啶并吡嗪基、吡嗪并吡嗪基、异喹啉基、吲哚基、咔唑基、苯并噁唑基、苯并咪唑基、苯并噻唑基、苯并咔唑基、苯并噻吩基、二苯并噻吩基、噻吩并噻吩基、苯并呋喃基、菲咯啉基、异噁唑基、噻二唑基、苯并噻唑基、吩噻嗪基、硅芴基、二苯并呋喃基以及N-芳基咔唑基(如N-苯基咔唑基)、N-杂芳基咔唑基(如N-吡啶基咔唑基)、N-烷基咔唑基(如N-甲基咔唑基)等，而不限于此。其中，噻吩基、呋喃基、菲咯啉基等为单个芳香环体系类型的杂芳基，N-芳基咔唑基、N-杂芳基咔唑基为通过碳碳键共轭连接的多环体系类型的杂芳基。本申请的“取代或未取代的杂芳基”可含有3-30个碳原子，在一些实施方案中，取代或未取代的杂芳基中的碳原子数可以是12-20。举例而言，其碳原子数量可以是3、4、5、7、12、13、15、18、20，当然，碳原子数还可以是其他数量，在此不再一一列举。
在本申请中，涉及的亚杂芳基是指杂芳基进一步失去一个或多个氢原子所形成的多价基团。
在本申请中，取代的杂芳基可以是杂芳基中的一个或者两个以上氢原子被诸如氘原子、卤素基 团、氰基、芳基、杂芳基、三甲基硅基、烷基、环烷基、烷氧基、烷硫基等基团取代。应当理解地是，取代的杂芳基的碳原子数，指的是杂芳基和杂芳基上的取代基的碳原子总数。
在本申请中，作为取代基的杂芳基，具体实例包括但不限于：吡啶基、咔唑基、二苯并呋喃基、二苯并噻吩基。
在本申请中，卤素基团可以包括氟、碘、溴、氯等。
本申请中的“环”包含饱和环、不饱和环；饱和环即环烷基、杂环烷基；不饱和环，即环烯基、杂环烯基、芳基和杂芳基。
本申请中，不定位连接键是指从环体系中伸出的单键
Figure PCTCN2022094927-appb-000007
其表示该连接键的一端可以连接该键所贯穿的环体系中的任意位置，另一端连接化合物分子其余部分。
举例而言，如下式(f)中所示地，式(f)所表示的萘基通过两个贯穿双环的不定位连接键与分子其他位置连接，其所表示的含义，包括如式(f-1)～式(f-10)所示出的任一可能的连接方式。
Figure PCTCN2022094927-appb-000008
再举例而言，如下式(X')中所示地，式(X')所表示的二苯并呋喃基通过一个从一侧苯环中间伸出的不定位连接键与分子其他位置连接，其所表示的含义，包括如式(X'-1)～式(X'-4)所示出的任一可能的连接方式。
Figure PCTCN2022094927-appb-000009
下文中对于不定位连接或不定位取代的含义与此处相同，后续将不再进行赘述。
在本申请的一种实施方式中，所述化学式1具有式A至F中任意一项所示的结构：
Figure PCTCN2022094927-appb-000010
Figure PCTCN2022094927-appb-000011
在本申请的一种实施方式中，R 3、R 4和R 5彼此相同或不同，且各自独立地选自氢、氘、氟、氰基、碳原子数为1-5的烷基、碳原子数为6-12的芳基、碳原子数为3-12的杂芳基；
任选地，任意两个相邻的R 3形成碳原子数为3-15的饱和或不饱和环，或者任意两个相邻的R 4的形成碳原子数为3-15的饱和或不饱和环，或者任意两个相邻的R 5形成碳原子数为3-15的饱和或不饱和环。
可选地，所述任意两个相邻的R 3形成苯环。
可选地，所述任意两个相邻的R 4形成苯环。
可选地，所述任意两个相邻的R 5形成苯环。
在本申请一种具体实施方式中，n选自1，R 1、R 2均选自氢。
在本申请一种具体实施方式中，n选自1，R 1、R 2均选自甲基。
在本申请一种具体实施方式中，n选自1，R 1选自氢，R 2选自甲基。
在本申请一种具体实施方式中，n选自2，R 1、R 2均选自氢。
在本申请一种具体实施方式中，n选自2，R 1、R 2均选自甲基。
在本申请一种具体实施方式中，n选自2，R 1选自氢，R 2选自甲基。
在本申请一种具体实施方式中，n选自2，R 1选自甲基，R 2选自氢。
在本申请的一种实施方式中，所述Het选自碳原子数为3-12的含氮亚杂芳基。
在本申请的一种实施方式中，所述Het选自亚三嗪基、亚嘧啶基、亚喹唑啉基、亚喹喔啉基、亚苯并恶唑基、亚苯并噻唑基或以下基团：
Figure PCTCN2022094927-appb-000012
需要说明的是，上述基团中，Het上只带有两个连接键的，代表该位置连接
Figure PCTCN2022094927-appb-000013
且L 2为单键且Ar 2为氢。
可选地，所述Het选自以下基团组成的组：
Figure PCTCN2022094927-appb-000014
其中，
Figure PCTCN2022094927-appb-000015
表示Het与L 3连接位置，
Figure PCTCN2022094927-appb-000016
表示Het与L 1的连接位置，
Figure PCTCN2022094927-appb-000017
表示Het与L 2的连接位置，式中无
Figure PCTCN2022094927-appb-000018
的，代表该位置所连接的
Figure PCTCN2022094927-appb-000019
中，L 2为单键，Ar 2为氢。
在本申请的一种实施方式中，所述L 1、L 2、L 3、L 4彼此相同或不同，且各自独立地选自单键、碳原子数为6-12的取代或未取代的亚芳基、碳原子数为12的取代或未取代的亚杂芳基。
可选地，所述L 1、L 2、L 3、L 4彼此相同或不同，且各自独立地选自单键、取代或未取代的亚苯基、取代或未取代的亚联苯基、取代或未取代的亚萘基、取代或未取代的咔唑基；
可选地，所述L 1、L 2、L 3、L 4中的取代基彼此相同或不同，且各自独立地选自氘、卤素基团、氰基、碳原子数为1-5的烷基或苯基。
具体地，所述L 1、L 2、L 3、L 4中的取代基彼此相同或不同，且各自独立地选自氘、氟、氰基、甲基、乙基、异丙基、叔丁基或苯基。
在本申请的一种实施方式中，所述L 1、L 2、L 3、L 4彼此相同或不同，且各自独立地选自单键、取代或未取代的基团V；其中，未取代的基团V选自以下基团组成的组：
Figure PCTCN2022094927-appb-000020
其中，取代的基团V上具有一个或多个取代基，所述取代基各自独立地选自：氘、氟、氰基、甲基、乙基、异丙基、叔丁基、苯基；当V的取代基个数大于1时，各取代基相同或不同。
可选地，所述L 1、L 2、L 3、L 4各自独立地选自单键或以下基团组成的组：
Figure PCTCN2022094927-appb-000021
在本申请一种实施方式中，所述Ar 1、Ar 2分别独立地选自氢、碳原子数为6-20的取代或未取代的芳基、碳原子数为12-20的取代或未取代的杂芳基；
可选地，所述Ar 1、Ar 2中的取代基分别独立地选自氘、卤素基团、氰基、碳原子数为1-5的烷基、碳原子数为6-12的芳基。
具体地，所述Ar 1、Ar 2中的取代基分别独立地选自氘、氟、氰基、甲基、乙基、异丙基、叔丁基或苯基。
在本申请另一种实施方式中，所述Ar 1、Ar 2分别独立地选自氢、取代或未取代的苯基、取代或未取代的萘基、取代或未取代的联苯基、取代或未取代的二苯并呋喃基、取代或未取代的二苯并噻吩基、取代或未取代的咔唑基、取代或未取代的芴基。
可选地，Ar 1选自取代或未取代的苯基、取代或未取代的萘基、取代或未取代的联苯基、取代或未取代的二苯并呋喃基、取代或未取代的二苯并噻吩基、取代或未取代的咔唑基、取代或未取代的芴基；
Ar 2选自氢、取代或未取代的苯基、取代或未取代的萘基、取代或未取代的联苯基、取代或未取代的二苯并呋喃基、取代或未取代的二苯并噻吩基、取代或未取代的咔唑基、取代或未取代的芴基。
在本申请一种实施方式中，所述Ar 1、Ar 2分别独立地选自氢、取代或未取代的基团W；其中，未取代的基团W选自以下基团组成的组：
Figure PCTCN2022094927-appb-000022
其中，所述Ar 1、Ar 2中的取代基分别独立地选自氘、氟、氰基、甲基、乙基、异丙基、叔丁基或苯基。
可选地，所述Ar 1、Ar 2分别独立地选自氢或以下基团组成的组：
Figure PCTCN2022094927-appb-000023
在本申请的一种实施方式中，
Figure PCTCN2022094927-appb-000024
选自以下基团组成的组：
Figure PCTCN2022094927-appb-000025
Figure PCTCN2022094927-appb-000026
可选地，
Figure PCTCN2022094927-appb-000027
选自以下基团组成的组：
Figure PCTCN2022094927-appb-000028
Figure PCTCN2022094927-appb-000029
在本申请的一种实施方式中，所述有机化合物选自如下化合物组成的组：
Figure PCTCN2022094927-appb-000030
Figure PCTCN2022094927-appb-000031
Figure PCTCN2022094927-appb-000032
Figure PCTCN2022094927-appb-000033
Figure PCTCN2022094927-appb-000034
Figure PCTCN2022094927-appb-000035
Figure PCTCN2022094927-appb-000036
Figure PCTCN2022094927-appb-000037
Figure PCTCN2022094927-appb-000038
Figure PCTCN2022094927-appb-000039
Figure PCTCN2022094927-appb-000040
Figure PCTCN2022094927-appb-000041
Figure PCTCN2022094927-appb-000042
Figure PCTCN2022094927-appb-000043
Figure PCTCN2022094927-appb-000044
Figure PCTCN2022094927-appb-000045
Figure PCTCN2022094927-appb-000046
Figure PCTCN2022094927-appb-000047
Figure PCTCN2022094927-appb-000048
Figure PCTCN2022094927-appb-000049
Figure PCTCN2022094927-appb-000050
Figure PCTCN2022094927-appb-000051
Figure PCTCN2022094927-appb-000052
Figure PCTCN2022094927-appb-000053
Figure PCTCN2022094927-appb-000054
Figure PCTCN2022094927-appb-000055
Figure PCTCN2022094927-appb-000056
Figure PCTCN2022094927-appb-000057
Figure PCTCN2022094927-appb-000058
Figure PCTCN2022094927-appb-000059
Figure PCTCN2022094927-appb-000060
Figure PCTCN2022094927-appb-000061
Figure PCTCN2022094927-appb-000062
Figure PCTCN2022094927-appb-000063
本申请还提供一种有机电致发光器件，用于实现光电转换或者电光转化。该有机电致发光器件包括相对设置的阳极和阴极，以及介于阳极与阴极之间的至少一层功能层，该功能层包含本申请的有机化合物。
在本申请一种具体实施方式中，如图1所示，本申请的有机电致发光器件包括阳极100、阴极200、以及介于阳极层与阴极层之间的至少一层功能层300，该功能层300包括空穴注入层310、空穴传输层320、空穴辅助层330、有机电致发光层340、电子传输层350以及电子注入层360；空穴注入层310、空穴传输层320、空穴辅助层330、有机电致发光层340、电子传输层350以及电子注入层360可以依次形成在阳极100上，有机电致发光层340可以含有本申请第一方面所述的有机化合物，优选含有化合物A1～A252、B1～B188、C1～C88、D1～D76、F1～F32、G1～G24、H1～H24、I1～I56中的至少一种。
如图1所示，有机电致发光器件包括相对设置的阳极100和阴极200，以及设于阳极100和阴极200之间的功能层300；功能层300包含本申请所提供的有机化合物。
可选地，本申请所提供的有机化合物可以用于形成功能层300中的至少一个有机薄层，以改善有机电致发光器件的寿命特性、效率特性并且降低驱动电压；在某些实施例中，还可以提高有机电致发光器件的电化学稳定性和热稳定性，提高量产的有机电致发光器件的性能的均一性。
可选的，阳极100包括以下阳极材料，其优选地是有助于空穴注入至功能层中的具有大逸出功(功函数，work function)材料。阳极材料具体实例包括：金属如镍、铂、钒、铬、铜、锌和金或它们的合金；金属氧化物如氧化锌、氧化铟、氧化铟锡(ITO)和氧化铟锌(IZO)；组合的金属和氧化物如ZnO:Al或SnO 2:Sb；或导电聚合物如聚(3-甲基噻吩)、聚[3,4-(亚乙基-1,2-二氧基)噻吩](PEDT)、聚吡咯和聚苯胺，但不限于此。优选包括包含氧化铟锡(铟锡氧化物，indium tin oxide)(ITO)作为阳极的透明电极。
可选地，空穴传输层320可以包括一种或者多种空穴传输材料。空穴传输层材料选自咔唑多聚体化合物、咔唑连接三芳胺类化合物，本申请对此不做特殊的限定。举例而言，在本申请的一种实施方式中，空穴传输层320可由TPAC组成。
可选地，在阳极100和空穴传输层320之间还可以设置有空穴注入层310，以增强向空穴传输层320注入空穴的能力。空穴注入层310可以选用联苯胺衍生物、星爆状芳基胺类化合物、酞菁衍生物或者其他材料，本申请对此不做特殊的限制。举例而言，在本申请的一种实施方式中，空穴注入层310由F4-TCNQ组成。
可选地，空穴辅助层330可以可以选自咔唑多聚体、咔唑连接三芳胺类化合物或者其他材料，本申请对此不做特殊的限制。举例而言，在本申请的一种实施方式中，空穴辅助层330由HT-01组成。
可选地，有机电致发光层340可以包括本申请所提供的有机化合物，还可以包括其他有机电致发光层材料，本申请对此不做特殊的限制。举例而言，在本申请的一种实施方式中，有机电致发光层340由本申请所提供的有机化合物、GH-P以及Ir(3mppy) 3或者由RH-P、本申请所提供的有机化合物、Ir(dmpq) 2acac组成。
在本申请的一种实施方式中，有机电致发光器件为绿色有机电致发光器件，有机电致发光层340包含本申请所述的有机化合物、GH-P和客体材料Ir(3mppy) 3。
在本申请的一种实施方式中，有机电致发光器件为红色有机电致发光器件，有机电致发光层340包含包含本申请所述的有机化合物、RH-P和客体材料Ir(dmpq) 2acac。
电子传输层350可以为单层结构，也可以为多层结构，其可以包括一种或者多种电子传输材料，电子传输材料可以选自苯并咪唑衍生物、噁二唑衍生物、喹喔啉衍生物或者其他电子传输材料，本申请对此不做特殊的限定。举例而言，在本申请的一种实施方式中，电子传输层350可以由BCP和LiQ组成。
可选地，阴极200包括以下阴极材料，其是有助于电子注入至功能层中的具有小逸出功的材料。阴极材料的具体实例包括：金属如镁、钙、钠、钾、钛、铟、钇、锂、钆、铝、银、锡和铅或它们的合金；或多层材料如LiF/Al、Liq/Al、LiO 2/Al、LiF/Ca、LiF/Al和BaF 2/Ca，但不限于此。优选包括包含镁和银的金属电极作为阴极200。
可选地，在阴极200和电子传输层350之间还可以设置有电子注入层360，以增强向电子传输层350注入电子的能力。电子注入层360可以包括有碱金属硫化物、碱金属卤化物等无机材料，或者可以包括碱金属与有机物的络合物。举例而言，在本申请的一种实施方式中，电子注入层360为Yb。
本申请还提供一种电子装置，该电子装置包括本申请所述的电子元件。
举例而言，如图2所示，本申请提供的电子装置为第一电子装置400，该第一电子装置400包括上述有机电致发光器件实施方式所描述的任意一种有机电致发光器件。该电子装置可以为显示装置、照明装置、光通讯装置或者其他类型的电子装置，例如可以包括但不限于电脑屏幕、手机屏幕、电视机、电子纸、应急照明灯、光模块等。由于第一电子装置400具有上述有机电致发光器件，因此具有相同的有益效果，本申请在此不再赘述。
下面将结合实施例详细描述本申请，但是，以下描述是用于解释本申请，而不是以任意方式限制本申请的范围。
合成实施例
1、中间体IM-eX的合成
中间体IM-e1的合成：
Figure PCTCN2022094927-appb-000064
将IM-i1(10.0g；37.4mmol)，SM-B(8.7g；37.4mmol)，四三苯基膦钯(0.43g；0.37mmol)，碳酸钾(15.5g；112.3mmol)，四丁基溴化铵(0.12g；0.37mmol)，甲苯(240mL)，水(60mL)，乙醇(60mL)加入到圆底烧瓶中；在氮气保护下，升温至110℃搅拌反应6小时；降至室温，反应液使用水洗后分液，将有机相用无水硫酸镁干燥，然后减压除去溶剂得到粗品；以二氯甲烷/正庚烷作为洗脱剂将粗品使用硅胶柱色谱法提纯，得到IM-e1(9.82g；收率70％)。
参照中间体IM-e1的合成方法，使用下表中IM-X替代IM-i1，以及SM-B-Y替代SM-B，合成下表中所示的IM-eX，其中X可为1～13，Y可为1～5；所采用的主要原料以及相应合成的中间体结构及收率如表1所示。
表1
Figure PCTCN2022094927-appb-000065
Figure PCTCN2022094927-appb-000066
2、中间体IM-X的合成
中间体IM-a1的合成：
Figure PCTCN2022094927-appb-000067
将IM-i1(10.0g；37.4mmol)，吲哚并[2,3-a]咔唑(9.59g；37.4mmol)，三(二亚苄基丙酮)二钯(0.34g；0.37mmol)，三叔丁基膦(0.15g；0.75mmol)，叔丁醇钠(5.39g；56.1mmol)和二甲苯(100mL)加入到圆底烧瓶中；在氮气保护下，加热至140℃搅拌反应10小时；降至室温，反应液使用水洗后分液，有机相使用无水硫酸镁干燥，减压除去溶剂得到粗品；以二氯甲烷/正庚烷作为洗脱剂将粗品使用硅胶柱色谱法提纯，得到IM-a1(10.3g；收率62％)。
参照IM-a1的合成方法，使用下表中C替代IM-i1，以及B替代吲哚并[2,3-a]咔唑，合成下表中所示的IM-X，其中，X可为(a/b/c/d/e)1～18；所采用的主要原料以及相应合成的中间体结构及收率如表2所示。
表2
Figure PCTCN2022094927-appb-000068
Figure PCTCN2022094927-appb-000069
Figure PCTCN2022094927-appb-000070
Figure PCTCN2022094927-appb-000071
Figure PCTCN2022094927-appb-000072
Figure PCTCN2022094927-appb-000073
Figure PCTCN2022094927-appb-000074
3、化合物的合成
化合物A-2的合成：
Figure PCTCN2022094927-appb-000075
将中间体IM-a1(5.0g；11.3mmol)和二甲基甲酰胺(50mL)加入到圆底烧瓶中，将体系降至0℃，在氮气保护条件下，加入氢化钠(0.46g；11.3mmol)，保温搅拌1小时；而后向反应液中分批加入2-氯-4，6-二苯基-1，3，5-三嗪(4.54g；16.9mmol)，保温搅拌1小时，而后升温至25℃，搅拌反应8 小时；向反应液中加入100mL去离子水，过滤，将所得固体使用水和乙醇依次淋洗，干燥得到粗品；以二氯甲烷作为洗脱剂，使用硅胶柱色谱法对粗品进行提纯，而后使用甲苯对所得产品进行重结晶提纯，得到A-2(4.57g；收率60％)，m/z＝674.3。
参照A-2的合成方法，使用下表中IM-X替代IM-a1，以及SM-Y替代2-氯-4，6-二苯基-1，3，5-三嗪，合成下表中所示的化合物W；所采用的主要原料以及相应合成的化合物结构及收率如表3所示。
表3
Figure PCTCN2022094927-appb-000076
Figure PCTCN2022094927-appb-000077
Figure PCTCN2022094927-appb-000078
Figure PCTCN2022094927-appb-000079
Figure PCTCN2022094927-appb-000080
Figure PCTCN2022094927-appb-000081
Figure PCTCN2022094927-appb-000082
Figure PCTCN2022094927-appb-000083
部分化合物核磁数据如下表所示：
表4
Figure PCTCN2022094927-appb-000084
有机电致发光器件制备及评估：
器件实施例1：绿色有机电致发光器件
在形成有反射层的基板上以氧化铟锡(ITO)形成阳极，厚度为
Figure PCTCN2022094927-appb-000085
切割成40mm×40mm×0.7mm的尺寸，采用光刻工序，将其制备成具有阴极、阳极以及绝缘层图案的实验基板，采用有机溶剂清洗ITO基板表面，以清除其表面的杂质；或利用紫外臭氧以及O 2:N 2等离子表面处理，以增加阳极的功函数。
在基板阳极上利用PVD法真空蒸镀F4-TCNQ以形成厚度为
Figure PCTCN2022094927-appb-000086
的空穴注入层，并且在空穴注入层上蒸镀
Figure PCTCN2022094927-appb-000087
的TPAC形成空穴传输层。
在空穴传输层上蒸镀厚度
Figure PCTCN2022094927-appb-000088
的HT-01，形成空穴辅助层。
在空穴辅助层上，将化合物A-2：GH-P：Ir(3mppy) 3以45％：45％：10％的(蒸镀速率)比例进行共同蒸镀，形成厚度为
Figure PCTCN2022094927-appb-000089
的有机电致发光层(绿色发光层)。
将BCP和LiQ以1:1的重量比蒸镀形成
Figure PCTCN2022094927-appb-000090
厚的电子传输层，将Yb蒸镀在电子传输层上以形成厚度为
Figure PCTCN2022094927-appb-000091
的电子注入层，将镁和银以1：9的蒸镀比率共蒸在电子注入层上，形成厚度为
Figure PCTCN2022094927-appb-000092
的阴极。
此外，在上述阴极上蒸镀厚度为
Figure PCTCN2022094927-appb-000093
的CP-02，形成有机覆盖层(CPL)，从而实现有机发光器件的制备。
实施例2～37：
在形成绿色发光层时，以表2中所示的化合物替代实施例1中的化合物A-2，利用与实施例1相同的方法制作有机电致发光器件。
比较例1：
除了在形成绿色发光层时使用化合物1以外，采用与器件实施例1相同的方法制备有机电致发光器件。
比较例2：
除了在形成绿色发光层时使用化合物2以外，采用与器件实施例1相同的方法制作有机电致发光器件。
比较例3：
除了在形成绿色发光层时使用化合物3以外，采用与器件实施例1相同的方法制作有机电致发光器件。
比较例4
除了在形成绿色发光层时使用化合物4以外，采用与器件实施例1相同的方法制作有机电致发光器件。
器件实施例1～37和比较例1～4使用的材料结构如表5所示。
表5
Figure PCTCN2022094927-appb-000094
Figure PCTCN2022094927-appb-000095
在20mA/cm 2的条件下，对器件实施例1～37和比较例1～4中制备的有机电致发光器件进行IVL性能分析，在15mA/cm 2的条件下测试T95寿命，测试结果如表6所示。
表6
Figure PCTCN2022094927-appb-000096
Figure PCTCN2022094927-appb-000097
参考上表可知，器件实施例1～37将本申请有机化合物用作有机电致发光层混合主体的电子型主体材料，与比较例1～4相比较，电流效率至少提高了14.3％，功率效率至少提高了20.3％，寿命至少提高了15％。
器件实施例38：红色有机电致发光器件
将ITO厚度为
Figure PCTCN2022094927-appb-000098
的基板切割成40mm×40mm×0.7mm的尺寸，采用光刻工序，将其制备成具有阴极、阳极以及绝缘层图案的实验基板，利用紫外臭氧以及O 2:N 2等离子进行表面处理，以清除表面颗粒并提高阳极功函数。
在基板上采用PVD法真空蒸镀F4-TCNQ以形成厚度为
Figure PCTCN2022094927-appb-000099
的空穴注入层，并且在空穴注入层上蒸镀TPAC，形成厚度为
Figure PCTCN2022094927-appb-000100
的空穴传输层。
在空穴传输层上蒸镀厚度为
Figure PCTCN2022094927-appb-000101
的HT-01，形成空穴辅助层。
在空穴辅助层上，将化合物RH-P：化合物I-22：Ir(dmpq) 2acac以49％：49％：2％(蒸镀速率)的比例进行共同蒸镀，形成厚度为
Figure PCTCN2022094927-appb-000102
的有机电致发光层(红色发光层)。
将BCP和LiQ以1:1的重量比进行混合并蒸镀形成了
Figure PCTCN2022094927-appb-000103
厚的电子传输层，将Yb蒸镀在电子传输层上以形成
Figure PCTCN2022094927-appb-000104
的电子注入层，然后将镁和银以1：10的蒸镀速率，真空蒸镀在电子注入层上，形成
Figure PCTCN2022094927-appb-000105
的阴极。
在上述阴极上蒸镀
Figure PCTCN2022094927-appb-000106
厚度的CP-01，形成有机覆盖层(CPL)，完成有机发光器件的制造。
实施例39～47：
在形成红色发光层时，以表7中所示的化合物替代实施例1中的化合物I-22，利用与实施例38相同的方法制作有机电致发光器件。
比较例5：
参见表7，以化合物5替代实施例1中的化合物I-22，按照与实施例38相同的方法制备有机电致发光器件。
比较例6：
参见表7，以化合物6替代实施例1中的化合物I-22，按照与实施例38相同的方法制备有机电致发光器件。
在实施例38～47和比较例5～7中，所使用的各个材料的结构式如下。
表7
Figure PCTCN2022094927-appb-000107
对如上制得的有机电致发光器件，在20mA/cm 2的条件下分析了器件的性能，其结果如表8所示。
表8有机电致发光器件的性能测试结果
Figure PCTCN2022094927-appb-000108
Figure PCTCN2022094927-appb-000109
根据表8的结果可知，将本申请的有机化合物用作红色发光层的实施例38～47与比较例5～6相比，电流效率至少提高了10.3％，寿命至少提高了18％。
本申请的有机化合物具有以氮杂缺电子基团与富电子基团吲哚并咔唑相结合而成的结构；其中，氮杂缺电子基团与富电子的吲哚并咔唑的基团分别具有高的电子和空穴注入传输特性，使得材料分子结构具有双极性，适用于有机电致发光器件中的发光层；同时，二氢化茚、四氢化萘结构破坏了SP 3杂化结构，使得整个结构具有大的T 1(三线态能级)，因而可以在提升材料载流子迁移率和能量传输效率的前提下，有效提升分子结构的稳定性，从而有效改善器件性能。
本领域的普通技术人员可以理解，上述各实施方式是实现本申请的具体实施例，而在实际应用中，可以在形式上和细节上对其作各种改变，而不偏离本申请的精神和范围。

Claims (13)

  1. 一种有机化合物，其特征在于，所述有机化合物具有如化学式1表示的结构：
    Figure PCTCN2022094927-appb-100001
    其中，
    各R 1和R 2彼此相同或不同，且各自独立地选自氢、氘或甲基；n选自1或者2；
    R 3、R 4和R 5彼此相同或不同，且各自独立地选自氘、卤素基团、氰基、碳原子数为1-10的烷基、碳原子数为1-10的环烷基、碳原子数为1-10的卤代烷基、碳原子数为6-20的芳基、碳原子数为3-20的杂芳基；
    n 3表示R 3的个数，n 3选自0、1、2、3或4，当n 3大于1时，任意两个R 3相同或者不相同，任选地，任意两个相邻的R 3形成环；
    n 4表示R 4的个数，n 4选自0、1或2，当n 4大于1时，任意两个R 4相同或者不相同，任选地，任意两个相邻的R 4的形成环；
    n 5表示R 5的个数，n 5选自0、1、2、3或4，当n 5大于1时，任意两个R 5相同或者不相同，任选地，任意两个相邻的R 5形成环；
    Het选自碳原子数为3-30的含氮亚杂芳基；
    L 1、L 2、L 3、L 4彼此相同或不同，且各自独立地选自单键、碳原子数为6-30的取代或未取代的亚芳基、碳原子数为3-30的取代或未取代的亚杂芳基；
    Ar 1、Ar 2分别独立地选自氢、碳原子数为6-30的取代或未取代的芳基、碳原子数为3-30的取代或未取代的杂芳基；
    所述L 1、L 2、L 3、L 4、Ar 1、Ar 2中的取代基相同或不同，且分别独立地选自氘、卤素基团、氰基、碳原子数为3-20的杂芳基、碳原子数为6-20的芳基、碳原子数为3-12的三烷基硅基、碳原子数为1-10的烷基、碳原子数为1-10的卤代烷基、碳原子数为3-10的环烷基、碳原子数为2-10的杂环烷基、碳原子数为1-10的烷氧基。
  2. 根据权利要求1所述的有机化合物，其特征在于，所述R 3、R 4和R 5彼此相同或不同，且各自独立地选自氘、氟、氰基、碳原子数为1-5的烷基、碳原子数为6-12的芳基、碳原子数为3-12的杂芳基；
    任选地，任意两个相邻的R 3形成碳原子数为3-15的饱和或不饱和环，或者任意两个相邻的R 4形成碳原子数为3-15的饱和或不饱和环，或者任意两个相邻的R 5形成碳原子数为3-15的饱和或不饱和环。
  3. 根据权利要求1所述的有机化合物，其特征在于，所述Het选自碳原子数为3-12的含氮亚杂芳基。
  4. 根据权利要求1所述的有机化合物，其特征在于，所述Het选自亚三嗪基、亚嘧啶基、亚喹唑啉基、亚喹喔啉基、亚苯并噁唑基、亚苯并噻唑基或以下基团：
    Figure PCTCN2022094927-appb-100002
  5. 根据权利要求1所述的有机化合物，其特征在于，所述L 1、L 2、L 3、L 4彼此相同或不同，且各自独立地选自单键、碳原子数为6-12的取代或未取代的亚芳基、碳原子数为12的取代或未取代的亚杂芳基；
    优选地，所述L 1、L 2、L 3、L 4中的取代基各自独立地选自氘、卤素基团、氰基、碳原子数为1-5的烷基或苯基。
  6. 根据权利要求1所述的有机化合物，其特征在于，所述L 1、L 2、L 3、L 4彼此相同或不同，且各自独立地选自单键、取代或未取代的亚苯基、取代或未取代的亚联苯基、取代或未取代的亚萘基、取代或未取代的亚咔唑基；
    优选地，所述L 1、L 2、L 3、L 4中的取代基彼此相同或不同，且各自独立地选自氘、氟、氰基、甲基、乙基、异丙基、叔丁基或苯基。
  7. 根据权利要求1所述的有机化合物，其特征在于，所述L 1、L 2、L 3、L 4彼此相同或不同，且各自独立地选自单键、取代或未取代的基团V；其中，未取代的基团V选自以下基团组成的组：
    Figure PCTCN2022094927-appb-100003
    其中，取代的基团V上具有一个或多个取代基，所述取代基各自独立地选自：氘、氟、氰基、甲基、乙基、异丙基、叔丁基、苯基；当V的取代基个数大于1时，各取代基相同或不同。
  8. 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分别独立地选自氢、碳原子数为6-20的取代或未取代的芳基、碳原子数为12-20的取代或未取代的杂芳基；
    优选地，所述Ar 1、Ar 2中的取代基分别独立地选自氘、卤素基团、氰基、碳原子数为1-5的烷基、碳原子数为6-12的芳基。
  9. 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分别独立地选自氢、取代或未取代的苯基、取代或未取代的萘基、取代或未取代的联苯基、取代或未取代的二苯并呋喃基、取代或未取代的二苯并噻吩基、取代或未取代的咔唑基、取代或未取代的芴基；
    优选地，所述Ar 1、Ar 2中的取代基分别独立地选自氘、氟、氰基、甲基、乙基、异丙基、叔丁基或苯基。
  10. 根据权利要求1所述的有机化合物，其特征在于，
    Figure PCTCN2022094927-appb-100004
    选自以下基团组成的组：
    Figure PCTCN2022094927-appb-100005
    Figure PCTCN2022094927-appb-100006
  11. 根据权利要求1所述的有机化合物，其特征在于，所述有机化合物选自以下化合物所组成的组：
    Figure PCTCN2022094927-appb-100007
    Figure PCTCN2022094927-appb-100008
    Figure PCTCN2022094927-appb-100009
    Figure PCTCN2022094927-appb-100010
    Figure PCTCN2022094927-appb-100011
    Figure PCTCN2022094927-appb-100012
    Figure PCTCN2022094927-appb-100013
    Figure PCTCN2022094927-appb-100014
    Figure PCTCN2022094927-appb-100015
    Figure PCTCN2022094927-appb-100016
    Figure PCTCN2022094927-appb-100017
    Figure PCTCN2022094927-appb-100018
    Figure PCTCN2022094927-appb-100019
    Figure PCTCN2022094927-appb-100020
    Figure PCTCN2022094927-appb-100021
    Figure PCTCN2022094927-appb-100022
    Figure PCTCN2022094927-appb-100023
    Figure PCTCN2022094927-appb-100024
    Figure PCTCN2022094927-appb-100025
    Figure PCTCN2022094927-appb-100026
    Figure PCTCN2022094927-appb-100027
    Figure PCTCN2022094927-appb-100028
    Figure PCTCN2022094927-appb-100029
    Figure PCTCN2022094927-appb-100030
    Figure PCTCN2022094927-appb-100031
    Figure PCTCN2022094927-appb-100032
    Figure PCTCN2022094927-appb-100033
    Figure PCTCN2022094927-appb-100034
    Figure PCTCN2022094927-appb-100035
    Figure PCTCN2022094927-appb-100036
    Figure PCTCN2022094927-appb-100037
    Figure PCTCN2022094927-appb-100038
    Figure PCTCN2022094927-appb-100039
    Figure PCTCN2022094927-appb-100040
  12. 一种有机电致发光器件，其特征在于，包括相对设置的阳极和阴极，以及设于所述阳极和所述阴极之间的功能层；
    所述功能层包含权利要求1～11中任一项所述的有机化合物；
    优选地，所述功能层包括有机电致发光层，所述有机电致发光层包含所述的有机化合物。
  13. 一种电子装置，其特征在于，包括权利要求12所述的有机电致发光器件。
PCT/CN2022/094927 2021-06-21 2022-05-25 一种有机化合物及包含其的有机电致发光器件和电子装置 WO2022267801A1 (zh)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CN202110688704.2A CN114315836B (zh) 2021-06-21 2021-06-21 一种有机化合物及包含其的有机电致发光器件和电子装置
CN202110688704.2 2021-06-21

Publications (1)

Publication Number Publication Date
WO2022267801A1 true WO2022267801A1 (zh) 2022-12-29

Family

ID=81044231

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/CN2022/094927 WO2022267801A1 (zh) 2021-06-21 2022-05-25 一种有机化合物及包含其的有机电致发光器件和电子装置

Country Status (2)

Country Link
CN (1) CN114315836B (zh)
WO (1) WO2022267801A1 (zh)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN114315836B (zh) * 2021-06-21 2024-01-23 陕西莱特光电材料股份有限公司 一种有机化合物及包含其的有机电致发光器件和电子装置
CN115043785B (zh) * 2021-12-30 2023-08-04 陕西莱特光电材料股份有限公司 有机化合物、有机电致发光器件和电子装置
CN116396277A (zh) * 2022-11-09 2023-07-07 陕西莱特光电材料股份有限公司 有机化合物、有机电致发光器件及电子装置

Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20130292654A1 (en) * 2010-07-09 2013-11-07 Udc Ireland Limited Organic Electroluminescent Element
US20160087225A1 (en) * 2014-09-18 2016-03-24 Samsung Display Co., Ltd. Organic light emitting device
US20190140193A1 (en) * 2017-11-07 2019-05-09 Universal Display Corporation Organic electroluminescent materials and devices
CN112110849A (zh) * 2020-10-21 2020-12-22 陕西莱特光电材料股份有限公司 一种含氮化合物以及使用其的电子元件和电子装置
CN112812119A (zh) * 2020-05-20 2021-05-18 陕西莱特光电材料股份有限公司 一种有机化合物以及使用其的电子元件和装置
CN112876486A (zh) * 2021-01-25 2021-06-01 陕西莱特迈思光电材料有限公司 一种有机化合物及包含其的电子元件和电子装置
WO2021107736A1 (ko) * 2019-11-29 2021-06-03 주식회사 엘지화학 유기 발광 소자
CN114315836A (zh) * 2021-06-21 2022-04-12 陕西莱特迈思光电材料有限公司 一种有机化合物及包含其的有机电致发光器件和电子装置

Patent Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20130292654A1 (en) * 2010-07-09 2013-11-07 Udc Ireland Limited Organic Electroluminescent Element
US20160087225A1 (en) * 2014-09-18 2016-03-24 Samsung Display Co., Ltd. Organic light emitting device
US20190140193A1 (en) * 2017-11-07 2019-05-09 Universal Display Corporation Organic electroluminescent materials and devices
WO2021107736A1 (ko) * 2019-11-29 2021-06-03 주식회사 엘지화학 유기 발광 소자
CN112812119A (zh) * 2020-05-20 2021-05-18 陕西莱特光电材料股份有限公司 一种有机化合物以及使用其的电子元件和装置
CN112110849A (zh) * 2020-10-21 2020-12-22 陕西莱特光电材料股份有限公司 一种含氮化合物以及使用其的电子元件和电子装置
CN112876486A (zh) * 2021-01-25 2021-06-01 陕西莱特迈思光电材料有限公司 一种有机化合物及包含其的电子元件和电子装置
CN114315836A (zh) * 2021-06-21 2022-04-12 陕西莱特迈思光电材料有限公司 一种有机化合物及包含其的有机电致发光器件和电子装置

Also Published As

Publication number Publication date
CN114315836B (zh) 2024-01-23
CN114315836A (zh) 2022-04-12

Similar Documents

Publication Publication Date Title
WO2022160661A1 (zh) 一种含氮化合物及包含其的电子元件和电子装置
WO2022089428A1 (zh) 含氮化合物、包含其的电子元件和电子装置
CN113683519B (zh) 一种有机化合物及包含其的电子元件和电子装置
WO2021218588A1 (zh) 一种含氮化合物以及使用其的电子元件和电子装置
WO2022267801A1 (zh) 一种有机化合物及包含其的有机电致发光器件和电子装置
WO2022213905A1 (zh) 有机化合物以及使用其的电子元件和电子装置
WO2022088865A1 (zh) 含氮化合物、电子元件和电子装置
WO2022222737A1 (zh) 含氮化合物及包含其的电子元件和电子装置
WO2022222646A1 (zh) 含氮化合物、电子元件和电子装置
WO2023045729A1 (zh) 含氮化合物及电子元件和电子装置
WO2023231531A1 (zh) 含氮化合物、有机电致发光器件和电子装置
WO2022233243A1 (zh) 有机化合物及包含其的电子元件和电子装置
WO2022100194A1 (zh) 含氮化合物、有机电致发光器件和电子装置
WO2024055658A1 (zh) 含氮化合物和电子元件及电子装置
WO2024007511A1 (zh) 芳胺化合物及有机电致发光器件和电子装置
WO2023160121A1 (zh) 有机化合物及包含其的电子元件和电子装置
CN114335399A (zh) 有机电致发光器件及包括其的电子装置
WO2024164548A1 (zh) 有机化合物、有机电致发光器件及电子装置
WO2024164534A1 (zh) 有机化合物、有机电致发光器件和电子装置
WO2023202198A1 (zh) 有机材料、电子元件和电子装置
WO2023216669A1 (zh) 有机化合物、有机电致发光器件和电子装置
WO2023185078A1 (zh) 有机化合物和电子元件及电子装置
WO2023134228A1 (zh) 含氮化合物及包含其的有机电致发光器件和电子装置
CN117551110A (zh) 有机化合物及使用其的电子元件和电子装置
WO2022028334A1 (zh) 含氮化合物以及包含其的电子元件和电子装置

Legal Events

Date Code Title Description
121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 22827298

Country of ref document: EP

Kind code of ref document: A1

NENP Non-entry into the national phase

Ref country code: DE

122 Ep: pct application non-entry in european phase

Ref document number: 22827298

Country of ref document: EP

Kind code of ref document: A1