WO2024041183A1 - 有机化合物、有机电致发光器件和电子装置 - Google Patents

有机化合物、有机电致发光器件和电子装置 Download PDF

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WO2024041183A1
WO2024041183A1 PCT/CN2023/103475 CN2023103475W WO2024041183A1 WO 2024041183 A1 WO2024041183 A1 WO 2024041183A1 CN 2023103475 W CN2023103475 W CN 2023103475W WO 2024041183 A1 WO2024041183 A1 WO 2024041183A1
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substituted
carbon atoms
unsubstituted
independently selected
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French (fr)
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马天天
杨雷
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陕西莱特光电材料股份有限公司
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    • 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
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    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing aromatic rings
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    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
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    • 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
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    • C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
    • C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
    • C07D491/04—Ortho-condensed systems
    • C07D491/044—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring
    • C07D491/048—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring the oxygen-containing ring being five-membered
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    • C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
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    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
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Definitions

  • the present application relates to the technical field of organic compounds, and in particular to an organic compound and an organic electroluminescent device and electronic device containing the organic compound.
  • An organic electroluminescent device usually includes a cathode and an anode arranged oppositely, and a functional layer arranged between the cathode and anode.
  • the functional layer is composed of multiple organic or inorganic film layers, and generally includes an organic light-emitting layer, a hole transport layer, an electron transport layer, etc.
  • the purpose of this application is to provide an organic compound and an organic electroluminescent device and an electronic device containing the organic compound.
  • the organic compound can improve the performance of the organic electroluminescent device and electronic device, such as reducing the performance of the device. driving voltage to improve device efficiency and life.
  • a first aspect of the application provides an organic compound having a structure shown in Formula 1:
  • X is selected from C(R 4 R 5 ), O, S or N(R 6 );
  • R 1 and R 6 are the same or different, and are independently selected from a substituted or unsubstituted aryl group with 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group with 3 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group of formula 2. The group shown;
  • R 2 and R 3 are the same or different, and are independently selected from hydrogen, deuterium, cyano group, halogen group, substituted or unsubstituted aryl group with 6 to 30 carbon atoms, and substituted aryl group with 3 to 30 carbon atoms. Or unsubstituted heteroaryl or a group represented by formula 2;
  • R 1 , R 6 , R 2 and R 3 is a group represented by formula 2;
  • R 4 and R 5 are the same or different, and are independently selected from alkyl groups with 1 to 10 carbon atoms, substituted or unsubstituted aryl groups with 6 to 30 carbon atoms, or substituted aryl groups with 3 to 30 carbon atoms. or unsubstituted heteroaryl;
  • Each L, L 1 and L 2 are the same or different, and are independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, or a substituted or unsubstituted arylene group having 3 to 30 carbon atoms. heteroarylene;
  • n is the number of L groups connected in sequence, selected from 1, 2 or 3. When n is greater than 1, any two L groups are the same or different;
  • Ar 1 and Ar 2 are the same or different, and are each independently selected from a substituted or unsubstituted aryl group with 6 to 30 carbon atoms or a substituted or unsubstituted heteroaryl group with 3 to 30 carbon atoms;
  • R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , L, L 1 , L 2 , Ar 1 and Ar 2 are the same or different, and are independently selected from deuterium, halogen groups, Cyano group, alkyl group with 1 to 10 carbon atoms, cycloalkyl group with 3 to 20 carbon atoms, heteroaryl group with 3 to 20 carbon atoms, aryl group with 6 to 20 carbon atoms, carbon Deuterated aryl group with 6 to 20 atoms, haloaryl group with 6 to 20 carbon atoms, trialkylsilyl group with 3 to 12 carbon atoms, haloalkyl group with 1 to 10 carbon atoms or Deuterated alkyl group with 1 to 10 carbon atoms.
  • a second aspect of the present application provides an organic electroluminescent device, including an anode and a cathode arranged oppositely, and a functional layer disposed between the anode and the cathode; the functional layer includes the above-mentioned organic compound.
  • a third aspect of the present application provides an electronic device, including the organic electroluminescent device described in the second aspect.
  • the core group of the organic compound of the present application is composed of a five-membered dibenzo ring and a benzoxazole fused in a specific manner, and the core group has a planar, ring-like structure.
  • the compound can maintain a high first triplet energy level while possessing strong carrier transport capabilities and high energy transfer capabilities.
  • the organic compound of the present application is used as the host material of the emitting layer in a red organic electroluminescent device, the device performance can be significantly improved.
  • Figure 1 is a schematic structural diagram of an organic electroluminescent device of the present application.
  • FIG. 2 is a schematic structural diagram of an electronic device according to the present application.
  • the purpose of this application is to provide an organic compound and an organic electroluminescent device and an electronic device containing the organic compound.
  • the organic compound can improve the performance of the organic electroluminescent device and electronic device. , such as reducing the drive voltage of the device and improving device efficiency and life.
  • a first aspect of the application provides an organic compound having a structure shown in Formula 1:
  • X is selected from C(R 4 R 5 ), O, S or N(R 6 );
  • R 1 and R 6 are the same or different, and are independently selected from a substituted or unsubstituted aryl group with 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group with 3 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group of formula 2. The group shown;
  • R 2 and R 3 are the same or different, and are independently selected from hydrogen, deuterium, cyano group, halogen group, substituted or unsubstituted aryl group with 6 to 30 carbon atoms, and substituted aryl group with 3 to 30 carbon atoms. Or unsubstituted heteroaryl or a group represented by formula 2;
  • R 1 , R 6 , R 2 and R 3 is a group represented by formula 2;
  • R 4 and R 5 are the same or different, and are independently selected from alkyl groups with 1 to 10 carbon atoms, substituted or unsubstituted aryl groups with 6 to 30 carbon atoms, or substituted aryl groups with 3 to 30 carbon atoms. or unsubstituted heteroaryl;
  • Each L, L 1 and L 2 are the same or different, and are independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, or a substituted or unsubstituted arylene group having 3 to 30 carbon atoms. heteroarylene;
  • n is the number of L groups connected in sequence, selected from 1, 2 or 3. When n is greater than 1, any two L groups are the same or different;
  • Ar 1 and Ar 2 are the same or different, and are each independently selected from a substituted or unsubstituted aryl group with 6 to 30 carbon atoms or a substituted or unsubstituted heteroaryl group with 3 to 30 carbon atoms;
  • R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , L, L 1 , L 2 , Ar 1 and Ar 2 are the same or different, and are independently selected from deuterium, halogen groups, Cyano group, alkyl group with 1 to 10 carbon atoms, cycloalkyl group with 3 to 20 carbon atoms, heteroaryl group with 3 to 20 carbon atoms, aryl group with 6 to 20 carbon atoms, carbon Deuterated aryl group with 6 to 20 atoms, haloaryl group with 6 to 20 carbon atoms, trialkylsilyl group with 3 to 12 carbon atoms, haloalkyl group with 1 to 10 carbon atoms or Deuterated alkyl group with 1 to 10 carbon atoms.
  • each...independently is and “...respectively and independently are” and “...each independently is” are interchangeable, and should be understood in a broad sense. They can both refer to In different groups, the specific options expressed by the same symbols do not affect each other. 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, and chlorine.
  • Formula Q-1 represents that there are q substituents R" on the benzene ring.
  • each R can be the same or different, and the options of each R” do not affect each other;
  • Formula Q-2 indicates that there are q substituents R” on each benzene ring of biphenyl, and the R on the two benzene rings "The number of substituents q can be the same or different, each R" can be the same or different, and the options for 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 substituents are collectively referred to as Rc).
  • substituted or unsubstituted aryl refers to an aryl group having a substituent Rc or an unsubstituted aryl group.
  • the above-mentioned substituent Rc can be, for example, deuterium, cyano group, halogen group, alkyl group, haloalkyl group, deuterated alkyl group, trialkylsilyl group, aryl group, deuterated aryl group, heteroaryl group, cycloalkyl group Key et al.
  • the number of substitutions can be one or more.
  • plural refers to more than 2, such as 2, 3, 4, 5, 6, etc.
  • the number of carbon atoms of a substituted or unsubstituted functional group refers to the number of all carbon atoms. For example, if L 1 is a substituted arylene group having 12 carbon atoms, then all carbon atoms in the arylene group and the substituents thereon are 12.
  • aryl refers to an optional functional group or substituent derived from an aromatic carbocyclic ring.
  • the aryl group can be a single-ring aryl group (such as phenyl) or a polycyclic aryl group.
  • the aryl group can be a single-ring aryl group, a fused-ring aryl group, or two or more single-ring aryl groups conjugated through a carbon-carbon bond.
  • the condensed ring aryl group may include, for example, bicyclic condensed aryl group (such as naphthyl), tricyclic condensed aryl group (such as phenanthrenyl, fluorenyl, anthracenyl), etc.
  • Aryl groups do not contain heteroatoms such as B, N, O, S, P, Se and Si.
  • aryl groups may include, but are not limited to, phenyl, naphthyl, fluorenyl, anthracenyl, phenanthrenyl, biphenyl, terphenyl, triphenylene, perylene, benzo[9,10]phenanthrenyl, Pyrenyl, benzofluoranthene, base, spirobifluorenyl base, etc.
  • the arylene group refers to a bivalent group formed by the aryl group further losing one hydrogen atom.
  • terphenyl includes
  • the number of carbon atoms of a substituted aryl group refers to the total number of carbon atoms of the aryl group and the substituents on the aryl group.
  • a substituted aryl group with 18 carbon atoms refers to the aryl group and the substituent.
  • the total number of carbon atoms is 18.
  • the number of carbon atoms of the substituted or unsubstituted aryl group may be 6, 10, 12, 13, 14, 15, 16, 17, 18, 20, 25 or 30.
  • the substituted or unsubstituted aryl group is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.
  • the substituted or unsubstituted aryl group is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms. 25 substituted or unsubstituted aryl groups.
  • the substituted or unsubstituted aryl groups are substituted or unsubstituted aryl groups with 6 to 20 carbon atoms.
  • the substituted or unsubstituted aryl groups are The aryl group is a substituted or unsubstituted aryl group having 6 to 18 carbon atoms. In other embodiments, the substituted or unsubstituted aryl group is a substituted or unsubstituted aryl group having 6 to 12 carbon atoms.
  • the fluorenyl group can be substituted by one or more substituents, wherein any two adjacent substituents can be combined with each other to form a substituted or unsubstituted spirocyclic structure.
  • the substituted fluorenyl group can be: etc., but are not limited to this.
  • the aryl groups as substituents of R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , L, L 1 , L 2 , Ar 1 and Ar 2 are, for example, but not limited to, phenyl, Naphthyl and so on.
  • heteroaryl refers to a monovalent aromatic ring or its derivatives containing 1, 2, 3, 4, 5 or 6 heteroatoms in the ring.
  • the heteroatoms can be B, O, N, P, Si, One or more of Se and S.
  • a heteroaryl group can be a monocyclic heteroaryl group or a polycyclic heteroaryl group.
  • a heteroaryl group can be a single aromatic ring system or multiple aromatic ring systems conjugated through carbon-carbon bonds, 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, pyrimidinyl, triazinyl, Acridinyl, pyridazinyl, pyrazinyl, quinolinyl, quinazolinyl, quinoxalinyl, phenoxazinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyridyl Azinyl, isoquinolinyl, indolyl, carbazolyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothienyl, dibenzothienyl, thiophene Thiophenyl
  • the number of carbon atoms of the substituted or unsubstituted heteroaryl group can be selected from 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18 , 20, 21, 22, 23, 24, 25, 26, 27, 28, 29 or 30.
  • the substituted or unsubstituted heteroaryl group is a substituted or unsubstituted heteroaryl group having a total carbon number of 5 to 20. In other embodiments, the substituted or unsubstituted heteroaryl group is a total carbon number. Substituted or unsubstituted heteroaryl group having 12 to 18 atoms.
  • the substituted heteroaryl group may be one or more hydrogen atoms in the heteroaryl group substituted by deuterium atoms, halogen atoms, etc. Group, -CN, aryl, heteroaryl, trialkylsilyl, alkyl, cycloalkyl, haloalkyl and other group substitutions. It should be understood that the number of carbon atoms of a substituted heteroaryl group refers to the total number of carbon atoms of the heteroaryl group and the substituents on the heteroaryl group.
  • the alkyl group having 1 to 10 carbon atoms may include a linear alkyl group having 1 to 10 carbon atoms and a branched alkyl group having 3 to 10 carbon atoms.
  • the number of carbon atoms of the alkyl group may be, for example, 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10.
  • Specific examples of the alkyl group include, but are not limited to, methyl, ethyl, n-propyl, Isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl, neopentyl, n-hexyl, etc.
  • the halogen group can be, for example, fluorine, chlorine, bromine, or iodine.
  • trialkylsilyl include, but are not limited to, trimethylsilyl and the like.
  • haloalkyl groups include, but are not limited to, trifluoromethyl.
  • deuterated alkyl groups include, but are not limited to, trideuterated methyl.
  • the number of carbon atoms of the cycloalkyl group having 3 to 20 carbon atoms may be, for example, 3, 4, 5, 6, 7, 8, 10, 12 or 16.
  • Specific examples of cycloalkyl include, but are not limited to, cyclopentyl, cyclohexyl, and adamantyl.
  • the single bond extending from the ring system involved in the connecting key is not located. It means that one end of the bond can be connected to any position in the ring system that the bond penetrates, and the other end is connected to the rest of the compound molecule.
  • the naphthyl group represented by the formula (f) is connected to other positions of the molecule through two non-positioned bonds that penetrate the bicyclic ring, and its meaning includes such as the formula (f) -1) ⁇ Any possible connection method shown in formula (f-10).
  • the dibenzofuryl group represented by the formula (X') is connected to other positions of the molecule through an unpositioned bond extending from the middle of one side of the benzene ring, Its meaning includes any possible connection method shown in formula (X'-1) to formula (X'-4).
  • the substituents in R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , L, L 1 , L 2 , Ar 1 and Ar 2 are the same or different, respectively independently.
  • the organic compound has Formula 1-1, Formula 1-2, Formula 1-3, Formula 1-4, Formula 1-5, Formula 1-6, Formula 1-7, Formula 1 -8, the structure shown in Formula 1-9, Formula 1-10, Formula 1-11, Formula 1-12 or Formula 1-13:
  • n is selected from 1 or 2.
  • each L is the same or different, and is independently selected from a single bond or a substituted or unsubstituted arylene group having 6 to 12 carbon atoms.
  • the substituents in L are the same or different, and are independently selected from deuterium, halogen group, cyano group, alkyl group with 1 to 5 carbon atoms or phenyl group.
  • each L is the same or different, and is independently selected from a single bond, a phenylene group, a naphthylene group or a naphthylene group. biphenyl.
  • each L is the same or different, and is independently selected from the group consisting of a single bond or the following groups:
  • each L is the same or different, and is independently selected from the group consisting of a single bond or the following groups:
  • Equation 2 Selected from the group consisting of a single bond or the following groups:
  • L 1 and L 2 are the same or different, and are independently selected from single bonds, substituted or unsubstituted arylene groups with 6 to 12 carbon atoms, or arylene groups with 12 to 18 carbon atoms. Substituted or unsubstituted heteroarylene.
  • the substituents in L 1 and L 2 are the same or different, and are independently selected from deuterium, halogen group, cyano group, alkyl group with 1 to 5 carbon atoms or phenyl group.
  • L 1 and L 2 are the same or different, and are independently selected from a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted naphthylene group, Biphenyl, substituted or unsubstituted carbazolylene, substituted or unsubstituted dibenzofurylene or substituted or unsubstituted dibenzothienylene.
  • the substituents in L 1 and L 2 are the same or different, and are independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl or phenyl.
  • L 1 and L 2 are the same or different, and are independently selected from a single bond, a substituted or unsubstituted group V, and the unsubstituted group V is selected from the group consisting of the following groups:
  • the substituted group V contains one or more substituents selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl or phenyl; And when the substituted group V contains multiple substituents, the substituents may be the same or different.
  • L 1 and L 2 are the same or different, and are each independently selected from the group consisting of a single bond or the following groups:
  • Ar 1 and Ar 2 are the same or different, and are independently selected from substituted or unsubstituted aryl groups with 6 to 20 carbon atoms or substituted or unsubstituted aryl groups with 5 to 20 carbon atoms. of heteroaryl.
  • the substituents in Ar 1 and Ar 2 are the same or different, and are independently selected from deuterium, halogen group, cyano group, alkyl group with 1 to 5 carbon atoms, and alkyl group with 1 to 5 carbon atoms.
  • Ar 1 and Ar 2 are the same or different, and are independently selected from substituted or unsubstituted terphenyl, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or Unsubstituted biphenyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted triphenylene, substituted or unsubstituted pyridyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl or substituted or unsubstituted dibenzothienyl.
  • the substituents in Ar 1 and Ar 2 are the same or different, and are independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, cyclohexyl, Trifluoromethyl, trimethylsilyl or phenyl.
  • Ar 1 and Ar 2 are the same or different, and are independently selected from substituted or unsubstituted group W; wherein, unsubstituted group W is selected from the group consisting of the following groups:
  • the substituted group W has one or more substituents, each substituent is independently selected from deuterium, fluorine, cyano, cyclohexyl, methyl, ethyl, n-propyl, isopropyl, tert. Butyl, phenyl, trimethylsilyl or trifluoromethyl, and when the number of substituents on group W is greater than 1, each substituent may be the same or different.
  • Ar 1 and Ar 2 are the same or different, and are independently selected from the group consisting of the following groups:
  • Ar 1 and Ar 2 are the same or different, and are independently selected from the group consisting of the following groups:
  • R 4 and R 5 are the same or different, and are independently selected from methyl or substituted or unsubstituted phenyl.
  • substituents in R 4 and R 5 are the same or different, and are independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl or phenyl.
  • R 4 and R 5 are both methyl.
  • R 1 is selected from the group represented by formula 2 or the group consisting of the following groups:
  • R 6 is selected from the group represented by formula 2 or the group consisting of the following groups:
  • R 1 and R 6 are the same or different, and are independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl or formula 2. The group shown;
  • R 2 and R 3 are the same or different, and are independently selected from hydrogen or a group represented by formula 2;
  • R 1 , R 6 , R 2 and R 3 is a group represented by formula 2;
  • substituents in R 1 and R 6 are the same or different, and are independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl or phenyl.
  • R 1 is selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl or a group represented by Formula 2;
  • R 1 The substituents in R 1 are the same or different, and are independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl or phenyl.
  • R 6 is selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl or a group represented by Formula 2;
  • R 6 The substituents in R 6 are the same or different, and are independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl or phenyl.
  • R 2 is selected from hydrogen or a group represented by formula 2.
  • R3 is selected from hydrogen or a group represented by formula 2.
  • one and only one of R 1 , R 6 , R 2 and R 3 is a group represented by Formula 2.
  • X is O or S
  • R 2 and R 3 are the same or different, and are independently selected from hydrogen or the group represented by Formula 2;
  • R 6 is selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl or a group represented by formula 2;
  • R 1 , R 2 and R 3 is a group represented by Formula 2;
  • R 6 The substituents in R 6 are the same or different, and are independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl or phenyl.
  • the organic compound is selected from the group consisting of the following compounds:
  • the present application provides an organic electroluminescent device, including an anode and a cathode arranged oppositely, and a functional layer disposed between the anode and the cathode; the functional layer contains the organic compound of the present application.
  • the organic electroluminescent device is a red organic electroluminescent device.
  • the organic electroluminescent device may include an anode 100 , a first hole transport layer 320 , a second hole transport layer 330 , an organic light-emitting layer 340 , an electron transport layer 350 , and an electron injection layer 360 that are stacked in sequence. and cathode 200.
  • the anode 100 includes an anode material, which is optionally a material with a large work function that facilitates injection of holes 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 SnO2 :Sb; or conductive polymers such as polyethylene (3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDT), polypyrrole and polyaniline, but are not limited thereto.
  • a transparent electrode including indium tin oxide (ITO) as an anode is preferred.
  • the first hole transport layer 320 and the second hole transport layer 330 include one or more hole transport materials.
  • the hole transport materials may be selected from carbazole polymers and carbazole-linked triarylamine compounds. or other types of compounds. Persons skilled in the art can refer to the existing technology for selection, and this application does not impose special limitations on this.
  • the first hole transport layer 320 is HT-20
  • the second hole transport layer 330 is HT-21.
  • a hole injection layer 310 may also be provided between the anode 100 and the first hole transport layer 320 to enhance the ability to inject holes into the first hole transport layer 320 .
  • the hole injection layer 310 can be made of benzidine derivatives, starburst arylamine compounds, phthalocyanine derivatives or other materials, which are not particularly limited in this application.
  • the material of the hole injection layer 310 may, for example, be selected from the following compounds or any combination thereof;
  • the hole injection layer 310 is composed of HAT-CN.
  • the organic light-emitting layer 340 may be composed of a single light-emitting layer material, or may include a host material and a doping material.
  • the organic light-emitting layer 340 is composed of a host material and a doping material. The holes injected into the organic light-emitting layer 340 and the electrons injected into the organic light-emitting layer 340 can recombine in the organic light-emitting layer 340 to form excitons, and the excitons transfer energy. To the host material, the host material transfers energy to the doping material, thereby enabling the doping material to emit light.
  • the main material of the organic light-emitting layer 340 may be metal chelate compounds, bistyryl derivatives, aromatic amine derivatives, dibenzofuran derivatives or other types of materials, which are not specifically limited in this application.
  • the organic light-emitting layer 340 includes an organic compound of the present application.
  • the organic compound of the present application is used as the host material (electronic host material) of the organic light-emitting layer 340.
  • the hole-type host material of the organic light-emitting layer 340 is
  • the guest material of the organic light-emitting layer 340 may be a compound with a condensed aryl ring or its derivatives, a compound with a heteroaryl ring or its derivatives, an aromatic amine derivative or other materials, which is not specified in this application. limit. Guest materials are also called doping materials or dopants. Specific examples of red phosphorescent dopants for red organic electroluminescent devices include, but are not limited to,
  • the host material of the organic light-emitting layer 340 is the organic compound of the present application and RH-P, and the guest material is RD-01.
  • the electron transport layer 350 may have a single-layer structure or a multi-layer structure, and may include one or more electron transport materials.
  • the electron transport materials may be selected from, but are not limited to, ET-01, LiQ, and benzimidazole derivatives. , oxadiazole derivatives, quinoxaline derivatives or other electron transport materials, there are no special limitations for comparison in this application.
  • the materials of the electron transport layer 350 include but are not limited to the following compounds:
  • the electron transport layer 350 is composed of ET-01 and LiQ.
  • the cathode 200 may include a cathode material, which is a material with a small work function that facilitates electron injection into the functional layer.
  • cathode materials include, but are not limited to, metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead or alloys thereof; or multilayer materials such as LiF/Al , Liq/Al, LiO 2 /Al, LiF/Ca, LiF/Al and BaF 2 /Ca.
  • a metal electrode containing magnesium and silver is included as the cathode.
  • the electron injection layer 360 may include ytterbium (Yb).
  • a third aspect of this application provides an electronic device, including the electronic component described in the second aspect of this application.
  • the electronic device provided is an electronic device 400 , which includes the above-mentioned organic electroluminescent device.
  • the electronic device 400 may be, for example, a display device, a lighting device, an optical communication device, or other types of electronic devices.
  • it may include but is not limited to a computer screen, a mobile phone screen, a television, electronic paper, emergency lighting, an optical module, etc.
  • the compounds of the synthesis methods not mentioned in this application are all raw material products obtained through commercial channels.
  • This application does not specifically limit the synthesis method of the organic compounds provided. Those skilled in the art can determine a suitable synthesis method based on the organic compounds of this application combined with the preparation methods provided in the Preparation Examples section. Those skilled in the art can obtain all the organic compounds provided in the application based on these exemplary preparation methods. All specific preparation methods for preparing the organic compounds will not be described in detail here. Those skilled in the art should not understand it as a limitation of the application.
  • the organic phase is dried with anhydrous magnesium sulfate.
  • the solvent is removed under reduced pressure to obtain the crude product.
  • the crude product is purified by silica gel column chromatography using methylene chloride/n-heptane as the eluent, and then used The toluene/n-heptane solvent system was used for recrystallization and purification to obtain white solid compound B24 (4.0 g; yield 61%).
  • reaction solution was lowered to room temperature, deionized water (50 mL) was added, and the liquids were separated.
  • the organic phase was washed with water and dried over anhydrous magnesium sulfate.
  • the solvent was removed under reduced pressure; the crude product was subjected to silica gel column chromatography using a methylene chloride/n-heptane solvent system. Purify, and then use toluene/n-heptane solvent system for recrystallization and purification to obtain white solid compound A2 (2.3g; yield 55%).
  • HAT-CN was vacuum evaporated on the experimental substrate (anode) to form a thickness of hole injection layer (HIL), and then vacuum evaporate HT-20 on the hole injection layer to form a thickness of the first hole transport layer.
  • HIL hole injection layer
  • Compound HT-21 was vacuum evaporated on the first hole transport layer to form a thickness of the second hole transport layer.
  • RH-P Compound A2: RD-01 were co-evaporated at a evaporation rate ratio of 47%: 47%: 6% to form an organic light-emitting layer with a thickness of 400 ( EML).
  • compound ET-01 and LiQ are mixed at a weight ratio of 1:1 and evaporated to form Thick electron transport layer (ETL), Yb is evaporated on the electron transport layer to form a thickness of
  • the electron injection layer (EIL) is then mixed with magnesium (Mg) and silver (Ag) at an evaporation rate of 1:9, and vacuum evaporated on the electron injection layer to form a thickness of the cathode.
  • CP-1 was vacuum evaporated on the above cathode to form a thickness of The organic covering layer is used to complete the fabrication of red organic electroluminescent devices.
  • An organic electroluminescent device was prepared using the same method as in Example 1, except that the compounds in Table 15 below (collectively referred to as "Compound X”) were used instead of Compound A2 in Example 1 when making the organic light-emitting layer.
  • An organic electroluminescent device was prepared using the same method as in Example 1, except that when preparing the organic light-emitting layer, compound I and compound II were used instead of compound A2 in Example 1.
  • the red organic electroluminescent devices prepared in Examples 1 to 21 and Comparative Examples 1 to 2 were tested for performance. Specifically, the IVL performance of the device was tested under the condition of 10mA/cm 2 , and the T95 device life was tested under the condition of 20mA/cm 2 The test was carried out below, and the test results are shown in Table 15.
  • the core group of the organic compound of the present application is composed of a dibenzo five-membered ring and a benzoxazole fused in a specific manner, and the core group has a planar ring-like structure.
  • this core group is combined with a triazine group, the compound can maintain a high first triplet energy level while possessing strong carrier transport capabilities and high energy transfer capabilities.
  • the organic compound of the present application is used as the host material of the emitting layer in a red organic electroluminescent device, the device performance can be significantly improved.
  • the five-membered dibenzo ring is dibenzofuran/dibenzothiophene, the device performance is optimal.

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Abstract

本申请涉及一种有机化合物、有机电致发光器件和电子装置。本申请的有机化合物具有如式（1）所示的结构，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

有机化合物、有机电致发光器件和电子装置
相关申请的交叉引用
本申请要求于2022年8月22日递交的申请号为202211008191.7的中国专利申请的优先权，在此引用上述中国专利申请的内容全文以作为本申请的一部分。
技术领域
本申请涉及有机化合物技术领域，尤其涉及一种有机化合物及包含该有机化合物的有机电致发光器件和电子装置。
背景技术
随着电子技术的发展和材料科学的进步，用于实现电致发光或者光电转化的电子元器件的应用范围越来越广泛。有机电致发光器件(OLED)，通常包括相对设置的阴极和阳极，以及设置于阴极和阳极之间的功能层。该功能层由多层有机或者无机膜层组成，且一般包括有机发光层、空穴传输层、电子传输层等。当阴阳两极施加电压时，两电极产生电场，在电场的作用下，阴极侧的电子向电致发光层移动，阳极侧的空穴也向发光层移动，电子和空穴在电致发光层结合形成激子，激子处于激发态向外释放能量，进而使得电致发光层对外发光。根据电子自旋的统计定理，以1：3的比例生成单重态激子及三重态激子。使用利用单重态激子的发光的荧光发光型有机电致发光器件内部量子效率的极限是25％。另一方面，已知使用利用三重态激子的发光的磷光发光型有机电致发光器件在自单重态激子有效率地进行系间跨越(intersystemcrossing)的情况下，内部量子效率可提高至100％。
尽管如此，但是目前，在有机电致发光材料方面，对于磷光材料，仍存在许多问题。例如：寿命短、效率低。因此，有必要开发新的材料，从而提高电子元器件的性能。
所述背景技术部分公开的上述信息仅用于加强对本申请的背景的理解，因此它可以包括不构成对本领域普通技术人员已知的现有技术的信息。
发明内容
为解决上述问题，本申请目的在于提供一种有机化合物及包含该有机化合物的有机电致发光器件和电子装置，所述有机化合物可以改善有机电致发光器件和电子装置的性能，例如降低器件的驱动电压，提升器件效率和寿命。
本申请的第一方面，提供一种有机化合物，该有机化合物具有如式1所示的结构：
其中，X选自C(R4R5)、O、S或N(R6)；
R1和R6相同或不同，分别独立地选自碳原子数为6～30的取代或未取代的芳基、碳原子数为3～30的取代或未取代的杂芳基或式2所示的基团；
R2和R3相同或不同，分别独立地选自氢、氘、氰基、卤素基团、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或式2所示的基团；
R1、R6、R2和R3中有且只有一个为式2所示的基团；
R4和R5相同或不同，分别独立地选自碳原子数为1～10的烷基、碳原子数为6～30的取代或未取代的芳基或者碳原子数为3～30的取代或未取代的杂芳基；
各L、L1和L2相同或不同，分别独立地选自单键、碳原子数为6～30的取代或未取代的亚芳基或者碳原子数为3～30的取代或未取代的亚杂芳基；
n为依次连接的L基团的个数，选自1、2或3，当n大于1时，任意两个L相同或不同；
Ar1和Ar2相同或不同，分别独立地选自碳原子数为6～30的取代或未取代的芳基或者碳原子数为3～30的取代或未取代的杂芳基；
R1、R2、R3、R4、R5、R6、L、L1、L2、Ar1和Ar2中的取代基相同或不同，分别独立地选自氘、卤素基团、氰基、碳原子数为1～10的烷基、碳原子数为3～20的环烷基、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6～20的氘代芳基、碳原子数为6～20的卤代芳基、碳原子数为3～12的三烷基硅基、碳原子数为1～10的卤代烷基或者碳原子数为1～10的氘代烷基。
本申请的第二方面，提供一种有机电致发光器件，包括相对设置的阳极和阴极，以及设于所述阳极和所述阴极之间的功能层；所述功能层包含上述的有机化合物。
本申请的第三方面，提供了一种电子装置，包括第二方面所述的有机电致发光器件。
本申请有机化合物的核心基团是由二苯并五元环和苯并噁唑以特定方式稠合而成，该核心基团具有平面性的类环形的结构。将该核心基团与三嗪结合，化合物可在保持较高的第一三重态能级值的同时，拥有强的载流子传输能力以及高的能量转移能力。将本申请有机化合物用作红色有机电致发光器件中的发光层主体材料时，可以显著改善器件性能。
本申请的其他特征和优点将在随后的具体实施方式部分予以详细说明。
附图说明
附图是用来提供对本申请的进一步理解，并且构成说明书的一部分，与下面的具体实施方式一起用于解释本申请，但并不构成对本申请的限制。
图1是本申请一种的有机电致发光器件的结构示意图。
图2是本申请一种的电子装置的结构示意图。
附图标记
100、阳极 200、阴极 300、功能层 310、空穴注入层
320、空穴传输层 320、第一空穴传输层 330、第二空穴传输层 340、有机发光层
350、电子传输层 360、电子注入层 400、电子装置
具体实施方式
针对现有技术存在的上述问题，本申请的目的在于提供一种有机化合物及包含该有机化合物的有机电致发光器件和电子装置，所述有机化合物可以改善有机电致发光器件和电子装置的性能，例如降低器件的驱动电压，提升器件效率和寿命。
本申请的第一方面，提供一种有机化合物，该有机化合物具有如式1所示的结构：
其中，X选自C(R4R5)、O、S或N(R6)；
R1和R6相同或不同，分别独立地选自碳原子数为6～30的取代或未取代的芳基、碳原子数为3～30的取代或未取代的杂芳基或式2所示的基团；
R2和R3相同或不同，分别独立地选自氢、氘、氰基、卤素基团、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或式2所示的基团；
R1、R6、R2和R3中有且只有一个为式2所示的基团；
R4和R5相同或不同，分别独立地选自碳原子数为1～10的烷基、碳原子数为6～30的取代或未取代的芳基或者碳原子数为3～30的取代或未取代的杂芳基；
各L、L1和L2相同或不同，分别独立地选自单键、碳原子数为6～30的取代或未取代的亚芳基或者碳原子数为3～30的取代或未取代的亚杂芳基；
n为依次连接的L基团的个数，选自1、2或3，当n大于1时，任意两个L相同或不同；
Ar1和Ar2相同或不同，分别独立地选自碳原子数为6～30的取代或未取代的芳基或者碳原子数为3～30的取代或未取代的杂芳基；
R1、R2、R3、R4、R5、R6、L、L1、L2、Ar1和Ar2中的取代基相同或不同，分别独立地选自氘、卤素基团、氰基、碳原子数为1～10的烷基、碳原子数为3～20的环烷基、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6～20的氘代芳基、碳原子数为6～20的卤代芳基、碳原子数为3～12的三烷基硅基、碳原子数为1～10的卤代烷基或者碳原子数为1～10的氘代烷基。
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“……各自独立地为”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，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。
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)。举例来讲，“取代或未取代的芳基”是指具有取代基Rc的芳基或者没有取代的芳基。其中上述的取代基即Rc例如可以为氘、氰基、卤素基团、烷基、卤代烷基、氘代烷基、三烷基硅基、芳基、氘代芳基、杂芳基、环烷基等。取代的个数可以是1个或多个。
本申请中，“多个”是指2个以上，例如2个、3个、4个、5个、6个，等。
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L1为碳原子数为12的取代的亚芳基，则亚芳基及其上的取代基的所有碳原子数为12。
本申请中，芳基指的是衍生自芳香碳环的任选官能团或取代基。芳基可以是单环芳基(例如苯基)或多环芳基，换言之，芳基可以是单环芳基、稠环芳基、通过碳碳键共轭连接的两个或者更多个单环芳基、通过碳碳键共轭连接的单环芳基和稠环芳基、通过碳碳键共轭连接的两个或 者更多个稠环芳基。即，除非另有说明，通过碳碳键共轭连接的两个或者更多个芳香基团也可以视为本申请的芳基。其中，稠环芳基例如可以包括双环稠合芳基(例如萘基)、三环稠合芳基(例如菲基、芴基、蒽基)等。芳基中不含有B、N、O、S、P、Se和Si等杂原子。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、三亚苯基、苝基、苯并[9,10]菲基、芘基、苯并荧蒽基、基、螺二芴基等。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。
本申请中，三联苯基包括
本申请中，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，指的是芳基和取代基的总碳原子数为18。
本申请中，取代或未取代的芳基的碳原子数可以为6、10、12、13、14、15、16、17、18、20、25或30。在一些实施方案中，取代或未取代的芳基是碳原子数为6～30的取代或未取代的芳基，另一些实施方式中，取代或未取代的芳基是碳原子数为6～25的取代或未取代的芳基，另一些实施方式中，取代或未取代的芳基是碳原子数为6～20的取代或未取代的芳基，另一些实施方式中，取代或未取代的芳基是碳原子数为6～18的取代或未取代的芳基，另一些实施方式中，取代或未取代的芳基是碳原子数为6～12的取代或未取代的芳基。
本申请中，芴基可以被1个或多个取代基取代，其中，任意相邻的2个取代基可以彼此结合而形成取代或未取代的螺环结构。在上述芴基被取代的情况下，取代的芴基可以为： 等，但并不限定于此。
本申请中，作为R1、R2、R3、R4、R5、R6、L、L1、L2、Ar1和Ar2的取代基的芳基例如但不限于，苯基、萘基等等。
在本申请中，杂芳基是指环中包含1、2、3、4、5或6个杂原子的一价芳香环或其衍生物，杂原子可以是B、O、N、P、Si、Se和S中的一种或多种。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、吩噻嗪基、硅芴基、二苯并呋喃基以及N-苯基咔唑基、N-吡啶基咔唑基、N-甲基咔唑基等，而不限于此。
本申请中，取代或未取代的杂芳基的碳原子数可以选自3、4、5、6、7、8、9、10、11、12、13、14、15、16、17、18、20、21、22、23、24、25、26、27、28、29或30。在一些实施方案中，取代或未取代的杂芳基是总碳原子数为5～20的取代或未取代的杂芳基，另一些实施方式中，取代或未取代的杂芳基是总碳原子数为12～18的取代或未取代的杂芳基。
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、-CN、芳基、杂芳基、三烷基硅基、烷基、环烷基、卤代烷基等基团取代。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。
本申请中，碳原子数为1～10的烷基可以包括碳原子数1至10的直链烷基和碳原子数3至10的支链烷基。烷基的碳原子数例如可以为1、2、3、4、5、6、7、8、9、10个，烷基的具体实例包括但不限于，甲基、乙基、正丙基、异丙基、正丁基、异丁基、叔丁基、正戊基、异戊基、新戊基、正己基等。
本申请中，卤素基团例如可以为氟、氯、溴、碘。
本申请中，三烷基硅基的具体实例包括但不限于，三甲基硅基等。
本申请中，卤代烷基的具体实例包括但不限于，三氟甲基。
本申请中，氘代烷基的具体实例包括但不限于，三氘代甲基。
本申请中，碳原子数为3～20的环烷基的碳原子数例如可以为3、4、5、6、7、8、10、12或16等。环烷基的具体实例包括但不限于，环戊基、环己基、金刚烷基。
本申请中，不定位连接键涉及的从环体系中伸出的单键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。
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。
在本申请一些实施方式中，R1、R2、R3、R4、R5、R6、L、L1、L2、Ar1和Ar2中的取代基相同或不同，分别独立地选自氘、卤素基团、氰基、碳原子数为1～10的烷基、碳原子数为3～20的环烷基、碳原子数为3～20的杂芳基、碳原子数为6～20的氘代芳基、碳原子数为6～20的卤代芳基、碳原子数为3～12的三烷基硅基、碳原子数为1～10的卤代烷基或者碳原子数为1～10的氘代烷基。
在本申请一些实施方式中，所述有机化合物具有式1-1、式1-2、式1-3、式1-4、式1-5、式1-6、式1-7、式1-8、式1-9、式1-10、式1-11、式1-12或式1-13所示的结构：
在本申请一些实施方式中，n选自1或2。
在本申请一些实施方式中，各L相同或不同，分别独立地选自单键或者碳原子数为6～12的取代或未取代的亚芳基。
可选地，L中的取代基相同或不同，分别独立地选自氘、卤素基团、氰基、碳原子数为1～5的烷基或苯基。
在本申请另一些实施方式中，各L相同或不同，分别独立地选自单键、亚苯基、亚萘基或亚 联苯基。
在本申请一些实施方式中，各L相同或不同，分别独立地选自单键或如下基团组成的组：
具体地，各L相同或不同，分别独立地选自单键或如下基团组成的组：
在本申请一些实施方式中，式2中的选自单键或如下基团组成的组：
可选地，式2中的选自单键或如下基团组成的组：
在本申请一些实施方式中，L1和L2相同或不同，分别独立地选自单键、碳原子数为6～12的取代或未取代的亚芳基或者碳原子数为12～18的取代或未取代的亚杂芳基。
可选地，L1和L2中的取代基相同或不同，分别独立地选自氘、卤素基团、氰基、碳原子数为1～5的烷基或苯基。
在本申请另一些实施方式中，L1和L2相同或不同，分别独立地选自单键、取代或未取代的亚苯基、取代或未取代的亚萘基、取代或未取代的亚联苯基、取代或未取代的亚咔唑基、取代或未取代的亚二苯并呋喃基或者取代或未取代的亚二苯并噻吩基。
可选地，L1和L2中的取代基相同或不同，分别独立地选自氘、氟、氰基、甲基、乙基、正丙基、异丙基、叔丁基或苯基。
在本申请一些实施方式中，L1和L2相同或不同，分别独立地选自单键、取代或未取代的基团V，未取代的基团V选自如下基团组成的组：

其中，表示化学键；取代的基团V含有一个或多个取代基，所述取代基选自氘、氟、氰基、甲基、乙基、正丙基、异丙基、叔丁基或苯基；且当所述取代的基团V含有多个取代基时，所述取代基相同或者不相同。
在本申请一些实施方式中，L1和L2相同或不同，分别独立地选自单键或以下基团组成的组：
在本申请一些实施方式中，Ar1和Ar2相同或不同，分别独立地选自碳原子数为6～20的取代或未取代的芳基或者碳原子数为5～20的取代或未取代的杂芳基。
可选地，Ar1和Ar2中的取代基相同或不同，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1～5的卤代烷基、碳原子数为1～10的环烷基、三甲基硅基或苯基。
在本申请另一些实施方式中，Ar1和Ar2相同或不同，分别独立地选自取代或未取代的三联苯基、取代或未取代的苯基、取代或未取代的萘基、取代或未取代的联苯基、取代或未取代的菲基、取代或未取代的芴基、取代或未取代的三亚苯基、取代或未取代的吡啶基、取代或未取代的咔唑基、取代或未取代的二苯并呋喃基或者取代或未取代的二苯并噻吩基。
可选地，Ar1和Ar2中的取代基相同或不同，分别独立地选自氘、氟、氰基、甲基、乙基、正丙基、异丙基、叔丁基、环己基、三氟甲基、三甲基硅基或苯基。
在本申请一些实施方式中，Ar1和Ar2相同或不同，分别独立地选自取代或未取代的基团W；其中，未取代的基团W选自如下基团组成的组：
其中，表示化学键；取代的基团W中具有一个或两个以上取代基，取代基各自独立地选自氘、氟、氰基、环己基、甲基、乙基、正丙基、异丙基、叔丁基、苯基、三甲基硅基或三氟甲基，且当基团W上的取代基个数大于1时，各取代基相同或不同。
可选地，Ar1和Ar2相同或不同，分别独立地选自以下基团组成的组：
具体地，Ar1和Ar2相同或不同，分别独立地选自以下基团组成的组：
在本申请一些实施方式中，和相同或不同，各自独立地选自以下基团组成的组：

在本申请一些实施方式中，选自以下结构：


在本申请一些实施方式中，R4和R5相同或不同，分别独立地选自甲基或者取代或未取代的苯基。
可选地，R4和R5中的取代基相同或不同，分别独立地选自氘、氟、氰基、甲基、乙基、正丙基、异丙基、叔丁基或苯基。
在本申请一些更具体的实施方式中，R4和R5均为甲基。
在本申请一些实施方式中，R1选自式2所示的基团或如下基团组成的组：
在本申请一些实施方式中，R6选自式2所示的基团或如下基团组成的组：
在本申请一些实施方式中，R1和R6相同或不同，分别独立地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或式2所示的基团；
R2和R3相同或不同，分别独立地选自氢或式2所示的基团；
且R1、R6、R2和R3中有且仅有一个为式2所示的基团；
可选地，R1和R6中的取代基相同或不同，分别独立地选自氘、氟、氰基、甲基、乙基、正丙基、异丙基、叔丁基或苯基。
在本申请一些具体地实施方式中，R1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或式2所示的基团；
R1中的取代基相同或不同，分别独立地选自氘、氟、氰基、甲基、乙基、正丙基、异丙基、叔丁基或苯基。
在本申请一些实施方式中，R6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或式2所示的基团；
R6中的取代基相同或不同，分别独立地选自氘、氟、氰基、甲基、乙基、正丙基、异丙基、叔丁基或苯基。
R2选自氢或式2所示的基团。
R3选自氢或式2所示的基团。
在本申请一些实施方式中，R1、R6、R2和R3中有且仅有一个为式2所示的基团。
在本申请一些更具体的实施方式中，X为O或S，R2和R3相同或不同，分别独立地选自氢或式2所示的基团；
R6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或式2所示的基团；
且R1、R2和R3中有且仅有一个为式2所示的基团；
R6中的取代基相同或不同，分别独立地选自氘、氟、氰基、甲基、乙基、正丙基、异丙基、叔丁基或苯基。
在本申请一些实施方式中，所述有机化合物选自如下化合物组成的组：









本申请的第二方面，本申请提供一种有机电致发光器件，包括相对设置的阳极和阴极，以及设于阳极和阴极之间的功能层；所述功能层包含本申请的有机化合物。
在本申请一些实施方式中，有机电致发光器件为红色有机电致发光器件。如图1所示，有机电致发光器件可以包括依次层叠设置的阳极100、第一空穴传输层320、第二空穴传输层330、有机发光层340、电子传输层350、电子注入层360和阴极200。
可选地，阳极100包括以下阳极材料，其可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SnO2∶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。优选包括氧化铟锡(铟锡氧化物，indium tin oxide)(ITO)作为阳极的透明电极。
可选地，第一空穴传输层320和第二空穴传输层330包括一种或者多种空穴传输材料，空穴传输材料可以选自咔唑多聚体、咔唑连接三芳胺类化合物或者其他类型的化合物。本领域技术人员可参照现有技术选择，本申请对此不做特殊的限定。在本申请一些实施方式中，第一空穴传输层320为HT-20，第二空穴传输层330为HT-21。
可选地，在阳极100和第一空穴传输层320之间还可以设置有空穴注入层310，以增强向第一空穴传输层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。所述空穴注入层310的材料例如可以选自如下化合物或者其任意组合；
在本申请一些实施方式中，空穴注入层310由HAT-CN组成。
可选地，有机发光层340可以由单一发光层材料组成，也可以包括主体材料和掺杂材料。可选地，有机发光层340由主体材料和掺杂材料组成，注入有机发光层340的空穴和注入有机发光层340的电子可以在有机发光层340复合而形成激子，激子将能量传递给主体材料，主体材料将能量传递给掺杂材料，进而使得掺杂材料能够发光。
有机发光层340的主体材料可以为金属螯合类化合物、双苯乙烯基衍生物、芳香族胺衍生物、二苯并呋喃衍生物或者其他类型的材料，本申请对此不做特殊的限制。
在本申请一种实施方式中，有机发光层340包含本申请有机化合物。
可选地，本申请有机化合物用作有机发光层340的主体材料(电子型主体材料)。
在本申请一些实施方式中，有机发光层340的空穴型主体材料为
有机发光层340的客体材料可以为具有缩合芳基环的化合物或其衍生物、具有杂芳基环的化合物或其衍生物、芳香族胺衍生物或者其他材料，本申请对此不做特殊的限制。客体材料又称为掺杂材料或掺杂剂。用于红色有机电致发光器件的红光磷光掺杂剂的具体实例包括但不限于，

在一种更具体的实施方式中，有机发光层340的主体材料为本申请有机化合物和RH-P，客体材料为RD-01。
电子传输层350可以为单层结构，也可以为多层结构，其可以包括一种或者多种电子传输材料，电子传输材料可以选自但不限于，ET-01、LiQ、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，本申请对比不作特殊限定。所述电子传输层350的材料包含但不限于以下化合物：
在本申请一些具体实施方式中，电子传输层350由ET-01和LiQ组成。
本申请中，阴极200可以包括阴极材料，其是有助于电子注入至功能层中的具有小逸出功的材料。阴极材料的具体实例包括但不限于，金属如镁、钙、钠、钾、钛、铟、钇、锂、钆、铝、银、锡和铅或它们的合金；或多层材料如LiF/Al、Liq/Al、LiO2/Al、LiF/Ca、LiF/Al和BaF2/Ca。可选地，包括包含镁和银的金属电极作为阴极。
在本申请一些实施方式中，电子注入层360可以包括镱(Yb)。
本申请第三方面提供一种电子装置，包括本申请第二方面所述的电子元件。
按照一种实施方式，如图2所示，所提供的电子装置为电子装置400，其包括上述有机电致发光器件。电子装置400例如可以为显示装置、照明装置、光通讯装置或者其他类型的电子装置，例如可以包括但不限于电脑屏幕、手机屏幕、电视机、电子纸、应急照明灯、光模块等。
下面结合合成实施例来具体说明本申请的有机化合物的合成方法，但是本申请并不因此而受到任何限制。
本申请中未提到的合成方法的化合物的都是通过商业途径获得的原料产品。
本申请对提供的有机化合物的合成方法没有特别限定，本领域技术人员可以根据本申请的有机化合物结合制备例部分提供的制备方法确定合适的合成方法。本领域技术人员可以根据这些示例性的制备方法得到本申请提供的所有有机化合物，在此不再详述制备该有机化合物的所有具体制备方法，本领域技术人员不应理解为对本申请的限制。
合成实施例
所属领域的专业人员应该认识到，本申请所描述的化学反应可以用来合适地制备许多本申请的有机化合物，且用于制备本申请的化合物的其它方法都被认为是在本申请的范围之内。例如，根据本申请那些非例证的化合物的合成可以成功地被所属领域的技术人员通过修饰方法完成，如适当的保护干扰基团，通过利用其他已知的试剂除了本申请所描述的，或将反应条件做一些常规的修改。本申请中未提到的合成方法的化合物的都是通过商业途径获得的原料产品。
中间体a1的合成：
将2-溴-4-氯苯酚(25.0g；120.5mmol)，联硼酸频哪醇酯(30.6g；120.5mmol)，三(二亚苄基丙酮)二钯(1.1g；1.2mmol)，2-二环己基磷-2’,4’,6’-三异丙基联苯(1.1g；2.4mmol)，醋酸钾(17.7g；180.8mmol)和1,4-二氧六环(250mL)加入氮气保护的圆底烧瓶中，搅拌条件下于90℃～95℃反应48小时。降至室温，向反应液中加入二氯甲烷(250mL)和去离子水(500mL)，分液，有机相水洗后使用无水硫酸镁干燥，减压除去溶剂；所得粗品使用二氯甲烷/正庚烷作为溶剂进行硅胶柱色谱提纯，得到白色固体中间体a1(16.1g；收率52％)。
参照中间体a1的合成方法，以反应物A替代2-溴-4-氯苯酚，合成下表1所示的中间体：
表1

中间体b1的合成：
将中间体a1(16.1g；63.4mmol)，1,8-二溴萘(18.1g；63.4mmol)，四三苯基膦钯(1.5g；1.3mmol)，碳酸钾(17.5g；126.7mmol)，四丁基溴化铵(4.1g；12.7mmol)，甲苯(120mL)，乙醇(30mL)和去离子水(30mL)加入氮气保护的圆底烧瓶中，升温至75℃～80℃，搅拌反应24小时。将反应液降至室温，加入去离子水(200mL)，分液，有机相水洗后使用无水硫酸镁干燥，减压除去溶剂；所得粗品使用二氯甲烷/正庚烷溶剂体系进行硅胶柱色谱提纯，得到淡黄色油状物中间体b1(15.5g；收率73％)。
参照中间体b1的合成方法，以反应物C替代中间体a1，反应物B替代1,8-二溴萘，合成下表2所示的中间体：
表2


中间体c1的合成：
将中间体b1(15.5g；46.5mmol)，醋酸钯(1.0g；4.6mmol)，3-硝基吡啶(0.6g；4.6mmol)，六氟苯(60mL)，1,3-二甲基-2-咪唑啉酮(50mL)和过氧化苯甲酸叔丁酯(18.0g；92.9mmol)加入氮气保护的圆底烧瓶中，升温至90℃～95℃，反应12小时。停止反应并将其降至室温，向反应液中加入二氯甲烷(100mL)和去离子水(200mL)，分液，有机相水洗后使用无水硫酸镁干燥，减压除去溶剂；所得粗品使用二氯甲烷/正庚烷作为溶剂进行硅胶柱色谱提纯，得到白色固体中间体c1(8.0g；收率52％)。
参照中间体c1的合成方法，以反应物I替代中间体b1，合成下表3所示的中间体：
表3

中间体c6的合成：
将中间体b6(15.0g；41.4mmol)，三苯基膦(27.1g；103.4mmol)，邻二氯苯(150mL)加入氮气保护的圆底烧瓶中，搅拌条件下升温至175℃～180℃，反应48小时。将反应液降至室温，加入去离子水(200mL)，分液，有机相水洗后用无水硫酸镁干燥，高温减压条件下除去溶剂；所得粗品使用二氯甲烷/正庚烷体系进行硅胶柱色谱提纯，得到白色固体中间体c6(9.2g；收率67％)。
参照中间体c6的合成方法，以反应物E替代中间体b6，合成下表4所示的中间体：
表4

中间体c11的合成：
将中间体b11(8.5g；24.4mmol)，氯化钯(0.2g；1.2mmol)和二甲基亚砜(80mL)加入氮气保护的圆底烧瓶中，搅拌条件下于140℃～145℃反应24小时。降至室温，向反应液中加入二氯甲烷(100mL)和去离子水(150mL)，分液，有机相水洗后使用无水硫酸镁干燥，减压除去溶剂；所得粗品使用二氯甲烷/正庚烷体系进行硅胶柱色谱提纯，得到白色固体中间体c11(6.0g；收率71％)。
参照中间体c11的合成方法，以反应物G替代中间体b11，合成下表5所示的中间体：
表5
中间体c15的合成：
将中间体b15(18.0g；46.7mmol)和二氯乙烷(150mL)加入氮气保护的圆底烧瓶中，于20℃ ～25℃搅拌条件下，缓慢滴加三甲基铝的正己烷溶液(116.7mL,233.4mmol,2M)，滴加完毕后于20℃～25℃继续反应2小时；向反应液中加入盐酸(25.5g；700.2mmol)水溶液，使用乙醚进行萃取，合并有机相，干燥，减压除去溶剂；使用二氯甲烷/正庚烷作为溶剂体系对粗品进行硅胶色谱法提纯，得到白色固体中间体c15(7.5g；收率45％)。
参照中间体c15的合成方法，以反应物L替代中间体b15，合成下表6所示的中间体：
表6
中间体d1的合成：
将中间体c1(7.9g；23.8mol)，碘化亚铜(0.5g；2.4mmol)，8-羟基喹哪啶(0.8g；4.8mmol)，四丁基氢氧化铵(18.5g；71.5mmol)，二甲基亚砜(80mL)和去离子水(120mL)加入氮气保护的圆底烧瓶中，搅拌条件下升温至125℃～130℃，反应24小时。降至室温，向反应液中加入二氯甲烷(150mL)和去离子水(200mL)，分液，有机相水洗后使用无水硫酸镁干燥，减压除去溶剂；所得粗品使用二氯甲烷/正庚烷体系进行硅胶柱色谱提纯，得到白色固体中间体d1(5.1g；收率80％)。
参照中间体d1的合成方法，以反应物M替代中间体c1，合成下表7所示的中间体：
表7


中间体e1的合成：
将中间体d1(5.0g；18.6mmol),六水合硝酸镍(5.4g；18.6mmol)，对甲苯磺酸(0.04g；0.2mmol)和丙酮(100mL)加入氮气保护的圆底烧瓶中，于20℃～25℃搅拌条件下反应2小时。停止反应，向反应液中加入二氯甲烷(100mL)和去离子水(150mL)，分液，有机相水洗后使用无水硫酸镁干燥，减压除去溶剂；所得粗品使用二氯甲烷/正庚烷体系进行硅胶柱色谱提纯，得到白色固体中间体e1(4.7g；收率81％)。
参照中间体e1的合成方法，以反应物N替代中间体d1，合成下表8所示的中间体：
表8


中间体o1-cl的合成：
将中间体e1(4.7g；15.0mmol)，苯甲醇(1.9g,18.0mmol)，1,1’-双(二苯基膦)二茂铁(0.2g；0.4mmol)和二甲苯(50mL)加入氮气保护的圆底烧瓶中，搅拌条件下升温至130℃～135℃，回流反应48h。降至室温，向反应液中加入甲苯(50mL)和去离子水(100mL)，合并有机相，无水硫酸镁干燥有机层，过滤，进行浓缩；使用二氯甲烷/正庚烷体系对粗品进行硅胶柱色谱提纯，得到白色固体中间体 o1-cl(3.5g；收率63％)。
参照中间体o1-cl的合成方法，以反应物P替代中间体e1，反应物Q替代苯甲醇，合成下表9所示的中间体：
表9


中间体n1-cl的合成
将中间体n1-h(5.5g；14.9mmol)，碘苯(3.3g；16.4mmol)，碘化亚铜(0.6g；3.0mmol)，无水碳酸钾(4.5g；32.8mmol)，1,10-菲罗啉(1.1g；6.0mmol)，18-冠醚-6(0.8g；3.0mmol)和二甲基甲酰胺(50mL)加入氮气保护的圆底烧瓶中，搅拌条件下升温至135℃～140℃，反应24小时。停止反应，将反应液降至室温，加入去离子水(100mL)和二氯甲烷(100mL)，分液，有机相使用大量水洗后使用无水硫酸镁干燥，减压除去溶剂；所得粗品使用二氯甲烷/正庚烷溶剂体系进行硅胶柱色谱提纯，后使用二氯甲烷/正庚烷混合溶剂进行重结晶提纯，得到白色固体中间体n1-cl(5.1g；收率77％)。
参照中间体n1-cl的合成方法，以反应物R替代中间体n1-h，反应物U替代碘苯，合成下表10所示的中间体/化合物：
表10

化合物B24的合成：
将中间体n0-h(3.0g；9.0mmol)，2-氯-4-(联苯-4-基)-6-(二苯并呋喃-3-基)-1,3,5-三嗪(5.8g；13.5mmol)和N,N-二甲基甲酰胺(30mL)加入圆底烧瓶中，氮气保护下搅拌降温至-5℃～0℃，加入氢化钠(0.3g；10.8mmol)，于-5℃～0℃搅拌反应30分钟后，升至20℃～25℃，反应16小时。停止反应，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，而后使用甲苯/正庚烷溶剂体系进行重结晶提纯，得到白色固体化合物B24(4.0g；收率61％)。
中间体o1-bo的合成：
将中间体o1-cl(3.5g；9.5mmol)，联硼酸频哪醇酯(3.6g；14.2mmol)，三(二亚苄基丙酮)二钯(0.2g；0.2mmol)，2-二环己基磷-2’,4’,6’-三异丙基联苯(0.2g；0.4mmol)，醋酸钾(1.4g；14.2mmol)和1,4-二氧六环(30mL)加入氮气保护的圆底烧瓶中，搅拌条件下于100℃～105℃反应24小时。降至室温，向反应液中加入二氯甲烷(50mL)和去离子水(50mL)，分液，有机相水洗后使用无水硫酸镁干燥，减压除去溶剂；所得粗品使用二氯甲烷/正庚烷作为溶剂进行硅胶柱色谱提纯，得到白色固体中间体o1-bo(3.1g；收率71％)。
参照中间体o1-bo的合成方法，以反应物V替代中间体o1-cl，合成下表11所示的中间体：
表11


化合物A2的合成：
将中间体o1-bo(3.0g；6.5mmol)，2-氯-4-(联苯-4-基)-6-苯基-1,3,5-三嗪(2.3g；6.8mmol)，四三苯基膦钯(0.2g；0.1mmol)，碳酸钾(1.8g；13.0mmol)，四丁基溴化铵(0.4g；1.3mmol)，甲苯(24mL)，乙醇(6mL)和去离子水(6mL)加入氮气保护的圆底烧瓶中，升温至75℃～80℃，搅拌反应24小时。将反应液降至室温，加入去离子水(50mL)，分液，有机相水洗后使用无水硫酸镁干燥，减压除去溶剂；所得粗品使用二氯甲烷/正庚烷溶剂体系进行硅胶柱色谱提纯，而后使用甲苯/正庚烷溶剂体系进行重结晶提纯，得到白色固体化合物A2(2.3g；收率55％)。
参照化合物A2的合成方法，以反应物Y替代中间体o1-bo，反应物Z替代2-氯-4-(联苯-4-基)-6-苯基-1,3,5-三嗪，合成下表12所示的化合物：
表12


部分化合物的质谱数据如下表13所示：
表13
部分化合物的核磁数据如下表14所示：
表14
有机电致发光器件的制备
实施例1：红色有机电致发光器件的制备
先通过以下过程进行阳极预处理：在厚度依次为的ITO/Ag/ITO基板上，利用紫外臭氧以及O2:N2等离子进行表面处理，以增加阳极的功函数，采用有机溶剂清洗ITO/Ag/ITO基板表面，以清除基板表面的杂质及油污。
在实验基板(阳极)上真空蒸镀HAT-CN以形成厚度为的空穴注入层(HIL)，然后在空穴注入层上真空蒸镀HT-20，形成厚度为的第一空穴传输层。
在第一空穴传输层上真空蒸镀化合物HT-21，形成厚度为的第二空穴传输层。
接着，在第二空穴传输层上，将RH-P:化合物A2:RD-01以47％﹕47％:6％的蒸镀速率比例进行共同蒸镀，形成厚度为400的有机发光层(EML)。
在有机发光层上，将化合物ET-01和LiQ以1:1的重量比进行混合并蒸镀形成厚的电子传输层(ETL)，将Yb蒸镀在电子传输层上以形成厚度为的电子注入层(EIL)，然后将镁(Mg)和银(Ag)以1:9的蒸镀速率混合，真空蒸镀在电子注入层上，形成厚度为的阴极。
此外，在上述阴极上真空蒸镀CP-1，形成厚度为的有机覆盖层，从而完成红色有机电致发光器件的制造。
实施例2～21
除了在制作有机发光层时，以下表15中的化合物(统称为“化合物X”)代替实施例1中的化合物A2之外，利用与实施例1相同的方法制备有机电致发光器件。
比较例1～2
除了在制作有机发光层时，分别以化合物Ⅰ和化合物Ⅱ代替实施例1中的化合物A2之外，利用与实施例1相同的方法制备有机电致发光器件。
其中，在制备各实施例及比较例时，所用的主要化合物结构如下：
对实施例1～21和比较例1～2制备所得的红色有机电致发光器件进行性能测试，具体在10mA/cm2的条件下测试器件的IVL性能，T95器件寿命在20mA/cm2的条件下进行测试，测试结果见表15。
表15

根据表15可知，将本申请化合物用作红色发光层混合主体材料中的电子型主体材料的实施例1～21，与比较例1和2相比，器件电压、电流效率及寿命均得到了明显改善。具体而言，器件效率至少提高了13.4％，寿命至少提高了12.3％。
本申请有机化合物的核心基团是由二苯并五元环和苯并噁唑以特定方式稠合而的，该核心基团在具有平面性的类环形的结构。将该核心基团与三嗪基团结合时，化合物可在保持较高的第一三重态能级值的同时，拥有强的载流子传输能力以及高的能量转移能力。将本申请有机化合物用作为红色有机电致发光器件中的发光层主体材料时，可以显著改善器件性能。特别地，当二苯并五元环为二苯并呋喃/二苯并噻吩时，器件性能最优。
应当理解的是，本申请并不局限于上面已经描述并在附图中示出的精确结构，并且可以在不脱离其范围进行各种修改和改变。本申请的范围仅由所附的权利要求书来限制。

Claims (15)

  1. 一种有机化合物，其特征在于，该有机化合物具有如式1所示的结构：
    其中，X选自C(R4R5)、O、S或N(R6)；
    R1和R6相同或不同，分别独立地选自碳原子数为6～30的取代或未取代的芳基、碳原子数为3～30的取代或未取代的杂芳基或式2所示的基团；
    R2和R3相同或不同，分别独立地选自氢、氘、氰基、卤素基团、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或式2所示的基团；
    R1、R6、R2和R3中有且只有一个为式2所示的基团；
    R4和R5相同或不同，分别独立地选自碳原子数为1～10的烷基、碳原子数为6～30的取代或未取代的芳基或者碳原子数为3～30的取代或未取代的杂芳基；
    各L、L1和L2相同或不同，分别独立地选自单键、碳原子数为6～30的取代或未取代的亚芳基或者碳原子数为3～30的取代或未取代的亚杂芳基；
    n为依次连接的L基团的个数，选自1、2或3，当n大于1时，任意两个L相同或不同；
    Ar1和Ar2相同或不同，分别独立地选自碳原子数为6～30的取代或未取代的芳基或者碳原子数为3～30的取代或未取代的杂芳基；
    R1、R2、R3、R4、R5、R6、L、L1、L2、Ar1和Ar2中的取代基相同或不同，分别独立地选自氘、卤素基团、氰基、碳原子数为1～10的烷基、碳原子数为3～20的环烷基、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6～20的氘代芳基、碳原子数为6～20的卤代芳基、碳原子数为3～12的三烷基硅基、碳原子数为1～10的卤代烷基或者碳原子数为1～10的氘代烷基。
  2. 根据权利要求1所述的有机化合物，其特征在于，R1、R2、R3、R4、R5、R6、L、L1、L2、Ar1和Ar2中的取代基相同或不同，分别独立地选自氘、卤素基团、氰基、碳原子数为1～10的烷基、碳原子数为3～20的环烷基、碳原子数为3～20的杂芳基、碳原子数为6～20的氘代芳基、碳原子数为6～20的卤代芳基、碳原子数为3～12的三烷基硅基、碳原子数为1～10的卤代烷基或者碳原子数为1～10的氘代烷基。
  3. 根据权利要求1或2所述的有机化合物，其特征在于，所述有机化合物具有式1-1、式1-2、式1-3、式1-4、式1-5、式1-6、式1-7、式1-8、式1-9、式1-10、式1-11、式1-12或式1-13所示的结构：
  4. 根据权利要求1或2所述的有机化合物，其特征在于，各L相同或不同，分别独立地选自单键或者碳原子数为6～12的取代或未取代的亚芳基；
    可选地，L中的取代基相同或不同，分别独立地选自氘、卤素基团、氰基、碳原子数为1～5的烷基或苯基。
  5. 根据权利要求1或2所述的有机化合物，其特征在于，各L相同或不同，分别独立地选自单键、亚苯基、亚萘基或亚联苯基。
  6. 根据权利要求1或2所述的有机化合物，其特征在于，式2中的选自单键或如下基团组成的组：
  7. 根据权利要求1或2所述的有机化合物，其特征在于，L1和L2相同或不同，分别独立地选自单键、碳原子数为6～12的取代或未取代的亚芳基或者碳原子数为12～18的取代或未取代的亚杂芳基；
    可选地，L1和L2中的取代基相同或不同，分别独立地选自氘、卤素基团、氰基、碳原子数为1～5的烷基或苯基。
  8. 根据权利要求1或2所述的有机化合物，其特征在于，L1和L2相同或不同，分别独立地选自单键、取代或未取代的亚苯基、取代或未取代的亚萘基、取代或未取代的亚联苯基、取代或未取代的亚咔唑基、取代或未取代的亚二苯并呋喃基或者取代或未取代的亚二苯并噻吩基；
    可选地，L1和L2中的取代基相同或不同，分别独立地选自氘、氟、氰基、甲基、乙基、正丙基、异丙基、叔丁基或苯基。
  9. 根据权利要求1或2所述的有机化合物，其特征在于，Ar1和Ar2相同或不同，分别独立地选自碳原子数为6～20的取代或未取代的芳基或者碳原子数为5～20的取代或未取代的杂芳基；
    可选地，Ar1和Ar2中的取代基相同或不同，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1～5的卤代烷基、碳原子数为1～10的环烷基、三甲基硅基或苯基。
  10. 根据权利要求1或2所述的有机化合物，其特征在于，Ar1和Ar2相同或不同，分别独立地选自取代或未取代的三联苯基、取代或未取代的苯基、取代或未取代的萘基、取代或未取代的联苯基、取代或未取代的菲基、取代或未取代的芴基、取代或未取代的三亚苯基、取代或未取代的吡啶基、取代或未取代的咔唑基、取代或未取代的二苯并呋喃基或者取代或未取代的二苯并噻吩基；
    可选地，Ar1和Ar2中的取代基相同或不同，分别独立地选自氘、氟、氰基、甲基、乙基、正丙基、异丙基、叔丁基、环己基、三氟甲基、三甲基硅基或苯基。
  11. 根据权利要求1或2所述的有机化合物，其特征在于，R4和R5相同或不同，分别独立地选自甲基或者取代或未取代的苯基；
    可选地，R4和R5中的取代基相同或不同，分别独立地选自氘、氟、氰基、甲基、乙基、正丙基、异丙基、叔丁基或苯基。
  12. 根据权利要求1或2所述的有机化合物，其特征在于，R1和R6相同或不同，分别独立地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或式2所示的基团；
    R2和R3相同或不同，分别独立地选自氢或式2所示的基团；
    且R1、R6、R2和R3中有且仅有一个为式2所示的基团；
    可选地，R1和R6中的取代基相同或不同，分别独立地选自氘、氟、氰基、甲基、乙基、正丙基、异丙基、叔丁基或苯基。
  13. 根据权利要求1或2所述的有机化合物，其特征在于，所述有机化合物选自如下化合物组成的组：









  14. 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1～13任意一项所述的有机化合物；
    可选地，所述功能层包含有机发光层；所述有机发光层包含所述有机化合物；
    可选地，所述有机电致发光器件为红色有机电致发光器件。
  15. 电子装置，其特征在于，包括权利要求14所述的有机电致发光器件。
PCT/CN2023/103475 2022-08-22 2023-06-28 有机化合物、有机电致发光器件和电子装置 WO2024041183A1 (zh)

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