WO2024098735A1 - Composé organique, appareil électroluminescent organique et dispositif électronique - Google Patents

Composé organique, appareil électroluminescent organique et dispositif électronique Download PDF

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WO2024098735A1
WO2024098735A1 PCT/CN2023/098162 CN2023098162W WO2024098735A1 WO 2024098735 A1 WO2024098735 A1 WO 2024098735A1 CN 2023098162 W CN2023098162 W CN 2023098162W WO 2024098735 A1 WO2024098735 A1 WO 2024098735A1
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carbon atoms
organic compound
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徐先彬
杨雷
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陕西莱特光电材料股份有限公司
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • 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
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
    • C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
    • C07D493/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
    • C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
    • C07D495/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • 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
    • C07D498/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
    • C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
    • C07D513/04—Ortho-condensed systems
    • 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
    • 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]
    • H10K50/14—Carrier transporting layers
    • H10K50/16—Electron transporting layers
    • H10K50/165—Electron transporting layers comprising dopants
    • 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
    • H10K85/60—Organic compounds having low molecular weight

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 an electronic device comprising the organic compound.
  • Such electronic components generally include a cathode and an anode arranged relatively to each other, and a functional layer arranged between the cathode and the anode.
  • the functional layer is composed of multiple layers of organic or inorganic film layers, and generally includes an organic light-emitting layer, a hole transport layer located between the organic light-emitting layer and the anode, and an electron transport layer located between the organic light-emitting layer and the cathode.
  • an organic electroluminescent device as an example, it generally includes an anode, a hole transport layer, an organic light-emitting layer, an electron transport layer and a cathode stacked in sequence.
  • the two electrodes When a voltage is applied to the positive and negative electrodes, the two electrodes generate an electric field. Under the action of the electric field, the electrons on the cathode side move toward the organic light-emitting layer, and the holes on the anode side also move toward the organic light-emitting layer.
  • the electrons and holes combine in the organic light-emitting layer to form excitons, and the excitons are in an excited state and release energy outward, thereby causing the organic light-emitting layer to emit light outward.
  • the prior art discloses host materials that can be used to prepare organic light-emitting layers in organic electroluminescent devices. However, it is still necessary to continue to develop new materials to further improve the performance of electronic components.
  • the purpose of the present application is to provide an organic compound and an organic electroluminescent device and an electronic device containing the organic compound, wherein the organic compound can improve the performance of the organic electroluminescent device and the electronic device, such as reducing the driving voltage of the device and improving the efficiency and life of the device.
  • an organic compound wherein the organic compound has a structure as shown in Formula 1:
  • ring A is a benzene ring or a naphthalene ring
  • X1 is O
  • S or X2 is O
  • S or and one of X1 and X2 is O or S, and the other is
  • L 1 , L 2 and L 3 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, and a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms;
  • L is selected from a substituted or unsubstituted arylene group having 6 to 30 carbon atoms and a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms;
  • Ar 1 , Ar 2 and Ar 3 are the same or different and are independently selected from a substituted or unsubstituted aryl group having 6 to 40 carbon atoms and a substituted or unsubstituted heteroaryl group having 3 to 40 carbon atoms;
  • the substituents of L, L 1 , L 2 , L 3 , Ar 1 , Ar 2 and Ar 3 are the same or different and are independently selected from deuterium, cyano, halogen groups, alkyl groups having 1 to 10 carbon atoms, halogenated alkyl groups having 1 to 10 carbon atoms, deuterated alkyl groups having 1 to 10 carbon atoms, aryl groups having 6 to 20 carbon atoms, deuterated aryl groups having 6 to 20 carbon atoms, halogenated aryl groups having 6 to 20 carbon atoms, A heteroaryl group having 5 to 20 carbon atoms, or a cycloalkyl group having 3 to 10 carbon atoms;
  • any two adjacent substituents form a ring
  • Each R1 and R2 is the same or different and is independently selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 5 carbon atoms, a haloalkyl group having 1 to 5 carbon atoms, a deuterated alkyl group having 1 to 5 carbon atoms, an aryl group having 6 to 18 carbon atoms, a deuterated aryl group having 6 to 18 carbon atoms, a heteroaryl group having 5 to 18 carbon atoms, or a cycloalkyl group having 3 to 10 carbon atoms;
  • n 1 represents the number of R 1 , n 1 is selected from 0, 1, 2, 3, 4, 5 or 6, and when n 1 is greater than 1, each R 1 is the same or different;
  • n2 represents the number of R2 , n2 is selected from 0, 1, 2, 3 or 4, and when n2 is greater than 1, each R2 is the same or different.
  • an organic electroluminescent device comprising an anode and a cathode arranged opposite to each other, and a functional layer arranged between the anode and the cathode; the functional layer comprises the above-mentioned organic compound.
  • an electronic device comprising the organic electroluminescent device described in the second aspect.
  • the core group of the organic compound of the present application is a benzoxazole-fused carbazole group, which has a large conjugated system. It is connected with the triazine group to form a new compound.
  • the substituent at the 2nd position of benzoxazole is in the same direction or parallel position as the triazine group in space. On the one hand, it can enhance the intermolecular force and improve the carrier mobility of the compound; on the other hand, it is beneficial to reduce the molecular volume and reduce the evaporation temperature.
  • the organic compound of the present application when used as an electron transport type main material in a hybrid main material, it can improve the carrier balance in the light-emitting layer, broaden the carrier recombination area, improve the exciton generation and utilization efficiency, and improve the device luminous efficiency and life.
  • FIG. 1 is a schematic diagram of the structure of an organic electroluminescent device of the present application.
  • FIG. 2 is a schematic diagram of the structure of an electronic device of the present application.
  • the purpose of the present application is to provide an organic compound and an organic electroluminescent device and an electronic device comprising the organic compound, wherein the organic compound can improve the performance of the organic electroluminescent device and the electronic device, such as reducing the driving voltage of the device and improving the efficiency and life of the device.
  • an organic compound wherein the organic compound has a structure as shown in Formula 1:
  • ring A is a benzene ring or a naphthalene ring
  • X1 is O
  • S or X2 is O
  • S or and one of X1 and X2 is O or S, and the other is
  • L 1 , L 2 and L 3 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, and a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms;
  • L is selected from a substituted or unsubstituted arylene group having 6 to 30 carbon atoms and a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms;
  • Ar 1 , Ar 2 and Ar 3 are the same or different and are independently selected from a substituted or unsubstituted aryl group having 6 to 40 carbon atoms and a substituted or unsubstituted heteroaryl group having 3 to 40 carbon atoms;
  • the substituents of L, L 1 , L 2 , L 3 , Ar 1 , Ar 2 and Ar 3 are the same or different and are independently selected from deuterium, cyano, halogen group, alkyl group having 1 to 10 carbon atoms, halogenated alkyl group having 1 to 10 carbon atoms, deuterated alkyl group having 1 to 10 carbon atoms, aryl group having 6 to 20 carbon atoms, deuterated aryl group having 6 to 20 carbon atoms, halogenated aryl group having 6 to 20 carbon atoms, heteroaryl group having 5 to 20 carbon atoms, and cycloalkyl group having 3 to 10 carbon atoms;
  • any two adjacent substituents form a ring
  • Each R1 and R2 is the same or different and is independently selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 5 carbon atoms, a haloalkyl group having 1 to 5 carbon atoms, a deuterated alkyl group having 1 to 5 carbon atoms, an aryl group having 6 to 18 carbon atoms, a deuterated aryl group having 6 to 18 carbon atoms, a heteroaryl group having 5 to 18 carbon atoms, or a cycloalkyl group having 3 to 10 carbon atoms;
  • n 1 represents the number of R 1 , n 1 is selected from 0, 1, 2, 3, 4, 5 or 6, and when n 1 is greater than 1, each R 1 is the same or different;
  • n2 represents the number of R2 , n2 is selected from 0, 1, 2, 3 or 4, and when n2 is greater than 1, each R2 is the same or different.
  • each q is independently 0, 1, 2 or 3, and each R" is independently selected from hydrogen, deuterium, fluorine, and chlorine, which means:
  • Formula Q-1 indicates that there are q substituents R" on the benzene ring, and 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 number q of R" substituents on the two benzene rings can be the same or different, and each R" can be the same or different, and the options of each R" do not affect each other.
  • substituted or unsubstituted means that the functional group recorded after the term may or may not have a substituent (hereinafter, for the convenience of description, the substituents are collectively referred to as Rc).
  • substituted or unsubstituted aryl refers to an aryl group having a substituent Rc or an unsubstituted aryl group.
  • Rc can be, for example, deuterium, cyano, halogen group, alkyl, haloalkyl, deuterated alkyl, aryl, deuterated aryl, haloaryl, heteroaryl, cycloalkyl, etc.
  • the number of substitutions can be 1 or more.
  • plural means more than 2, for example, 2, 3, 4, 5, 6, etc.
  • the number of carbon atoms of a substituted or unsubstituted functional group refers to the total number of carbon atoms.
  • L1 is a substituted arylene group having 12 carbon atoms
  • the total number of carbon atoms of the arylene group and the substituents thereon is 12.
  • aryl refers to an optional functional group or substituent derived from an aromatic carbocyclic ring.
  • Aryl can be a monocyclic aryl (e.g., phenyl) or a polycyclic aryl.
  • aryl can be a monocyclic aryl, a condensed ring aryl, two or more monocyclic aryl groups connected by carbon-carbon bond conjugation, a monocyclic aryl and a condensed ring aryl connected by carbon-carbon bond conjugation, and two or more condensed ring aryl groups connected by carbon-carbon bond conjugation.
  • condensed ring aryl can, for example, include bicyclic condensed aryl (e.g., naphthyl), tricyclic condensed aryl (e.g., phenanthrenyl, fluorenyl, anthracenyl), etc.
  • Aryl does 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, peryl, benzo[9,10]phenanthrenyl, pyrenyl, benzofluoranthenyl,
  • the arylene group refers to a divalent group formed by further losing a hydrogen atom from an aryl group.
  • 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 total number of carbon atoms of the aryl group and the substituents 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, 19, 20, 24, 25, 30, 31, 32, 33, 35, 36, 37, 38, 39 or 40.
  • 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 25 carbon atoms
  • the substituted or unsubstituted aryl group is a substituted or unsubstituted aryl group having 6 to 20 carbon atoms
  • the substituted or unsubstituted aryl group is a substituted or unsubstituted aryl group having 6 to 12 carbon atoms.
  • the fluorenyl group may be substituted by one or more substituents, wherein any two adjacent substituents may be combined with each other to form a ring structure.
  • the substituted fluorenyl group may be: etc., but not limited thereto.
  • examples of aryl groups as substituents for L, L 1 , L 2 , Ar 1 and Ar 2 include, but are not limited to, phenyl, naphthyl and the like.
  • heteroaryl refers to a monovalent aromatic ring or a derivative thereof containing 1 or more, for example 1, 2, 3, 4, 5 or 6 heteroatoms in the ring, and the heteroatoms may be one or more of B, O, N, P, Si, Se and S.
  • the heteroaryl may be a monocyclic heteroaryl or a polycyclic heteroaryl, in other words, the heteroaryl may be a single aromatic ring system or a plurality of aromatic ring systems conjugated by carbon-carbon bonds, and any aromatic ring system may be an aromatic monocyclic ring or an aromatic condensed ring.
  • the heteroaryl group may include a thienyl group, a furyl group, a pyrrolyl group, an imidazolyl group, a thiazolyl group, an oxazolyl group, an oxadiazolyl group, a triazolyl group, a pyridyl group, a bipyridyl group, a pyrimidyl group, a triazine group, an acridinyl group, a pyridazinyl group, a pyrazinyl group, a quinolyl group, a quinazolinyl group, a quinoxalinyl group, a phenoxazinyl group, a phthalazinyl group, a pyridopyrimidinyl group, a pyridopyrazinyl group, a pyrazinopyrazinyl group, an isoquinolyl group, an indolyl group, an
  • 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, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 35, 36, 37, 38, 39 or 40.
  • the substituted or unsubstituted heteroaryl group is a substituted or unsubstituted heteroaryl group having 5 to 20 carbon atoms
  • the substituted or unsubstituted heteroaryl group is a substituted or unsubstituted heteroaryl group having 12 to 18 carbon atoms.
  • the substituted heteroaryl group may be a heteroaryl group in which one or more hydrogen atoms are replaced by groups such as deuterium atoms, halogen groups, -CN, aryl groups, heteroaryl groups, trialkylsilyl groups, alkyl groups, cycloalkyl groups, haloalkyl groups, etc.
  • groups such as deuterium atoms, halogen groups, -CN, aryl groups, heteroaryl groups, trialkylsilyl groups, alkyl groups, cycloalkyl groups, haloalkyl groups, etc.
  • the number of carbon atoms in the substituted heteroaryl group refers to the total number of carbon atoms in the heteroaryl group and the substituents on the heteroaryl group.
  • the alkyl group having 1 to 10 carbon atoms may include a straight-chain alkyl group having 1 to 10 carbon atoms and a branched-chain alkyl group having 3 to 10 carbon atoms.
  • the number of carbon atoms in the alkyl group may be, for example, 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10, and 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, and the like.
  • the halogen group may be, for example, fluorine, chlorine, bromine, or iodine.
  • trialkylsilyl include, but are not limited to, trimethylsilyl and the like.
  • haloalkyl group examples include, but are not limited to, trifluoromethyl.
  • deuterated alkyl groups include, but are not limited to, trideuterated methyl groups.
  • the carbon number of the cycloalkyl group having 3 to 10 carbon atoms may be, for example, 3, 4, 5, 6, 7, 8, 9 or 10.
  • Specific examples of the cycloalkyl group include, but are not limited to, cyclopentyl, cyclohexyl, and adamantyl.
  • the dibenzofuranyl represented by formula (X') is connected to other positions of the molecule through a non-positional connecting bond extending from the middle of one side of the benzene ring, and its meaning includes any possible connection method shown in formula (X'-1) to formula (X'-4).
  • X1 is O
  • X2 is
  • X1 is X2 is O.
  • the organic compound is selected from the compound represented by Formula 1-A or Formula 1-B:
  • the organic compound is selected from the compounds shown in Formula 1-1, Formula 1-2, Formula 1-3, Formula 1-4, Formula 1-5, Formula 1-6, Formula 1-7 or Formula 1-8:
  • L is selected from a single bond, a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, and a substituted or unsubstituted heteroarylene group having 12 to 20 carbon atoms.
  • the substituents in L are the same or different and are independently selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 5 carbon atoms or a phenyl group.
  • L is selected from a single bond, and a substituted or unsubstituted arylene group having 6 to 12 carbon atoms.
  • L is selected from a single bond, a substituted or unsubstituted phenylene, a substituted or unsubstituted naphthylene, a substituted or unsubstituted biphenylene, a substituted or unsubstituted fluorenylene, a substituted or unsubstituted dibenzofuranylene, a substituted or unsubstituted dibenzothiophenylene, or a substituted or unsubstituted carbazolylene.
  • the substituents in L are the same or different and are independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl and phenyl.
  • L is selected from a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, and a substituted or unsubstituted biphenylene group.
  • L is selected from a single bond or the group consisting of:
  • L is selected from the group consisting of a single bond or the following groups:
  • L 1 , L 2 and L 3 are the same or different and are independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, and a substituted or unsubstituted heteroarylene group having 12 to 20 carbon atoms.
  • the substituents in L 1 , L 2 and L 3 are the same or different and are independently selected from deuterium, a halogen group, a cyano group, An alkyl group having 1 to 5 carbon atoms or a phenyl group.
  • L1 and L2 are the same or different, and are independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 18 carbon atoms, and a substituted or unsubstituted heteroarylene group having 12 to 18 carbon atoms.
  • L 3 is selected from a single bond, a substituted or unsubstituted arylene group having 6 to 12 carbon atoms.
  • L 1 , L 2 and L 3 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 biphenylene group, a substituted or unsubstituted fluorenylene group, a substituted or unsubstituted carbazolylene group, a substituted or unsubstituted dibenzofuranyl group, and a substituted or unsubstituted dibenzothiophenylene group.
  • the substituents in L 1 , L 2 and L 3 are the same or different, and are independently selected from deuterium, a halogen group, a cyano group, a methyl group, an ethyl group, a n-propyl group, an isopropyl group, a tert-butyl group or a phenyl group.
  • L 3 is selected from a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, and a substituted or unsubstituted biphenylene group.
  • L1 and L2 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, and the substituents are 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 are the same or different.
  • L1 and L2 are the same or different and are independently selected from a single bond or the following groups:
  • L 3 is selected from a single bond, a substituted or unsubstituted group V 1 , and the unsubstituted group V 1 is selected from the group consisting of the following groups:
  • the substituted group V 1 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 1 contains multiple substituents, the substituents are the same or different.
  • L3 is selected from a single bond or the group consisting of:
  • L3 is selected from a single bond or the group consisting of:
  • Ar 1 , Ar 2 and Ar 3 are the same or different, and are independently selected from a substituted or unsubstituted aryl group having 6 to 25 carbon atoms, and a substituted or unsubstituted heteroaryl group having 12 to 24 carbon atoms.
  • the substituents in Ar 1 , Ar 2 and Ar 3 are the same or different, and are independently selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 5 carbon atoms, a halogenated alkyl group having 1 to 5 carbon atoms, a deuterated alkyl group having 1 to 5 carbon atoms, a pentadeuterated phenyl group or a phenyl group;
  • any two adjacent substituents form a ring having 5 to 13 carbon atoms.
  • any two adjacent substituents form a cyclohexane ring.
  • Ar 1 and Ar 2 are the same or different, and are independently selected from a substituted or unsubstituted aryl group having 6 to 25 carbon atoms, and a substituted or unsubstituted heteroaryl group having 12 to 20 carbon atoms.
  • Ar 3 is selected from a substituted or unsubstituted aryl group having 6 to 20 carbon atoms and a substituted or unsubstituted heteroaryl group having 12 to 20 carbon atoms.
  • Ar 1 , Ar 2 and Ar 3 are the same or different, and are independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted fluorenyl, substituted or unsubstituted spirobifluorenyl, substituted or unsubstituted triphenylene, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl.
  • the substituents in Ar 1 , Ar 2 and Ar 3 are the same or different, and are independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, pentadeuterated phenyl or phenyl.
  • Ar 3 is selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted fluorenyl, substituted or unsubstituted triphenylene, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl.
  • Ar 1 and Ar 2 are the same or different, and are independently selected from substituted or unsubstituted groups W; wherein the unsubstituted group W is selected from the group consisting of the following groups:
  • the substituted group W has one or more substituents, each of which is independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, phenyl or pentadeuterated phenyl, and when the number of substituents on the group W is greater than 1, each substituent is 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:
  • Ar 3 is selected from a substituted or unsubstituted group W 1 ; wherein the unsubstituted group W 1 is selected from the group consisting of the following groups:
  • the substituted group W1 has one or more substituents, each of which is independently selected
  • the substituents on the W 1 group are selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, phenyl or pentadeuterated phenyl.
  • the number of substituents on the W 1 group is greater than 1, the substituents are the same or different.
  • Ar 3 is selected from the group consisting of:
  • Ar 3 is selected from the group consisting of:
  • R 1 and R 2 are the same or different, and are independently deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl or phenyl.
  • n1 and n2 are both 0.
  • the organic compound is selected from the group consisting of the following compounds:
  • the present application provides an organic electroluminescent device, comprising an anode and a cathode arranged opposite to each other, and a functional layer arranged between the anode and the cathode; the functional layer comprises 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, an electron injection layer 360 and a cathode 200 stacked in sequence.
  • the anode 100 includes the following anode material, which is optionally a material with a large work function that facilitates hole injection into the functional layer.
  • anode materials include: metals such as nickel, platinum, vanadium, chromium, copper, zinc and gold or 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 conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDT), polypyrrole and polyaniline, but are not limited thereto. It is preferred to include indium tin oxide (ITO) as a transparent electrode of the anode.
  • ITO indium tin oxide
  • the first hole transport layer 320 and the second hole transport layer 330 include one or more hole transport materials, and the hole transport material can be selected from carbazole polymers, carbazole-linked triarylamine compounds or other types of compounds. Those skilled in the art can refer to the prior art for selection, and this application does not make any special restrictions on this.
  • the first hole transport layer 320 is HT-22 and the second hole transport layer 330 is HT-23.
  • a hole injection layer 310 may 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 may be made of benzidine derivatives, starburst arylamine compounds, phthalocyanine derivatives or other materials, and the present application does not impose any particular limitation on this.
  • the material of the hole injection layer 310 may be selected from the following compounds or any combination thereof, for example;
  • the hole injection layer 310 is composed of PD and HT-22.
  • the organic light-emitting layer 340 may be composed of a single light-emitting layer material, or may include a main material and a doping material.
  • the organic light-emitting layer 340 is composed of a main material and a doping material, and holes injected into the organic light-emitting layer 340 and electrons injected into the organic light-emitting layer 340 may be recombined in the organic light-emitting layer 340 to form excitons, and the excitons transfer energy to the main material, and the main 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 a metal chelate compound, a bisphenylethylene derivative, an aromatic amine derivative, a dibenzofuran derivative or other types of materials, and the present application does not impose any special limitation thereto.
  • the organic light-emitting layer 340 includes the organic compound of the present application.
  • the organic compound of the present application is used as a 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 can be a compound having a condensed aromatic ring or a derivative thereof, a compound having a heteroaromatic ring or a derivative thereof, an aromatic amine derivative or other materials, and the present application does not impose any special restrictions on this.
  • the guest material is also called a doping material or a dopant.
  • 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.
  • the electron transport layer 350 may be a single-layer structure or a multi-layer structure, and may include one or more electron transport materials, which may be selected from but not limited to ET-01, LiQ, benzimidazole derivatives, oxadiazole derivatives, quinoxaline derivatives or other electron transport materials, and the present application does not make any special restrictions.
  • 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 the present application provides an electronic device, comprising the electronic component described in the second aspect of the present application.
  • the provided electronic device 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, such as, but not limited to, a computer screen, a mobile phone screen, a television, an electronic paper, an emergency lighting lamp, an optical module, etc.
  • the compounds whose synthesis methods are not mentioned in this application are all raw materials obtained through commercial channels.
  • the present application does not particularly limit the synthesis method of the organic compound provided, and those skilled in the art can determine a suitable synthesis method based on the organic compound of the present application in combination with the preparation method provided in the preparation example section. Those skilled in the art can obtain all the organic compounds provided in the present application based on these exemplary preparation methods, and all specific preparation methods for preparing the organic compound will not be described in detail here, and those skilled in the art should not be understood as limiting the present application.
  • 8-bromo-2-hydroxynaphthalene (11.1 g, 50 mmol), benzylamine (10.71 g, 100 mmol), ammonium persulfate ((NH 4 ) 2 S 2 O 8 , 22.82 g, 100 mmol), 2,2,6,6-tetramethylpiperidinoxide (TEMPO, 15.63 g, 100 mmol) and acetonitrile (CH 3 CN, 150 mL) were added to a 250 mL three-necked flask in sequence, stirring and heating were started, and the temperature was raised to 50°C and stirred for 24 h.
  • benzylamine (10.71 g, 100 mmol)
  • ammonium persulfate (NH 4 ) 2 S 2 O 8 , 22.82 g, 100 mmol)
  • TEMPO 2,2,6,6-tetramethylpiperidinoxide
  • CH 3 CN acetonitrile
  • reactant A shown in Table 1 was used instead of benzylamine to synthesize intermediates Sub-a2 to Sub-a6 respectively.
  • reactant B shown in Table 2 was used to replace Sub-a1
  • reactant C was used to replace o-chloroaniline to synthesize intermediates Sub-b2 to Sub-b9 respectively.
  • reactant D shown in Table 3 was used instead of Sub-b1 to synthesize intermediates Sub-c2 to Sub-c9 respectively.
  • 2-chloro-4-(2-naphthyl)-6-phenyl-1,3,5-triazine (15.85 g, 50 mmol), 5-chloro-1-naphthaleneboric acid (11.33 g, 55 mmol), tetrakis(triphenylphosphine)palladium (Pd(PPh 3 ) 4 , 0.58 g, 0.5 mmol), anhydrous sodium carbonate (Na 2 CO 3 , 10.60 g, 100 mmol), toluene (160 mL), tetrahydrofuran (THF, 40 mL) and deionized water (40 mL) were added to a 500 mL three-necked flask in sequence, and stirring and heating were started.
  • reactant E shown in Table 4 was used instead of 2-chloro-4-(2-naphthyl)-6-phenyl-1,3,5-triazine, and reactant F was used instead of 5-chloro-1-naphthaleneboric acid to synthesize intermediates Sub-d2 to Sub-d6.
  • Sub-c1 (16.70 g, 50 mmol), 2-chloro-4-(biphenyl-4-yl)-6-phenyl-1,3,5-triazine (25.73 g, 75 mmol) and dry DMF (500 mL) were added to a 1000 mL three-necked flask in sequence, the system was cooled to -10 ° C, sodium hydrogen (NaH, 60% content, 2.2 g, 55 mmol) was quickly added, and the reaction was stirred overnight.
  • sodium hydrogen NaH, 60% content, 2.2 g, 55 mmol
  • the anode pretreatment is carried out through the following process: the thickness is On the ITO/Ag/ITO substrate, the surface is treated by ultraviolet ozone and O 2 :N 2 plasma to increase the work function of the anode.
  • the surface of the ITO substrate can also be cleaned with an organic solvent to remove impurities and oil stains on the surface of the ITO substrate.
  • PD:HT-22 was co-evaporated at an evaporation rate ratio of 2%:98% to form a layer with a thickness of Then, HT-22 was vacuum-deposited on the HIL to form a HIL with a thickness of The first hole transport layer is formed by vacuum evaporating the compound HT-23 on the first hole transport layer to form a layer with a thickness of The second hole transport layer is formed by a plurality of holes.
  • compound 4:RH-P:RD was co-evaporated at an evaporation rate ratio of 49%:49%:2% to form a layer with a thickness of of an organic light-emitting layer (EML).
  • EML organic light-emitting layer
  • compound ET-01 and LiQ are co-evaporated at an evaporation rate ratio of 1:1 to form A thick electron transport layer (ETL) is formed by evaporating Yb on the electron transport layer to form a layer with a thickness of Then, magnesium (Mg) and silver (Ag) were mixed at a deposition rate of 1:9 and vacuum-deposited on the electron injection layer to form a layer with a thickness of cathode.
  • ETL electron transport layer
  • compound CP-1 is vacuum-evaporated on the cathode to form a layer with a thickness of An organic covering layer is formed, thereby completing the manufacture of a red organic electroluminescent device.
  • An organic electroluminescent device was prepared by the same method as in Example 1, except that compound Y in the following Table 8 was used instead of compound 4 in Example 1 when preparing the light-emitting layer.
  • An organic electroluminescent device was prepared by the same method as in Example 1, except that compound A, compound B and compound C were used to replace compound 4 in Example 1 when preparing the light-emitting layer.
  • the red organic electroluminescent devices prepared in Examples 1 to 37 and Comparative Examples 1 to 3 were subjected to performance tests. Specifically, the IVL performance of the devices was tested under the condition of 10 mA/cm 2 , and the T95 device life was tested under the condition of 20 mA/cm 2. The test results are shown in Table 8.
  • the organic compound of the present application is used as an organic electroluminescent device, and compared with Comparative Examples 1 to 3, the current efficiency is at least increased by 9.9%, and the T95 life is at least increased by 11.1%.

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Abstract

La présente demande appartient au domaine technique de l'électroluminescence organique, et concerne un composé organique, ainsi qu'un appareil électroluminescent organique et un dispositif électronique l'utilisant. Le composé organique a une structure telle que représentée par la formule (1), et l'utilisation du composé organique dans un appareil électroluminescent organique peut améliorer significativement les performances de l'appareil électroluminescent organique.
PCT/CN2023/098162 2022-11-11 2023-06-02 Composé organique, appareil électroluminescent organique et dispositif électronique WO2024098735A1 (fr)

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Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN103570737A (zh) * 2012-07-25 2014-02-12 三星显示有限公司 杂环化合物，包含其的有机发光装置和有机发光显示器
KR20140074729A (ko) * 2012-12-10 2014-06-18 주식회사 두산 인돌로카바졸계 유기 화합물 및 이를 포함하는 유기 전계 발광 소자
KR20140120090A (ko) * 2013-04-02 2014-10-13 에스에프씨 주식회사 유기발광 화합물 및 이를 포함하는 유기전계발광소자
CN113429395A (zh) * 2021-07-27 2021-09-24 北京八亿时空液晶科技股份有限公司 咪唑衍生物、有机电致发光材料、发光元件及消费型产品
WO2022030265A1 (fr) * 2020-08-07 2022-02-10 国立大学法人京都大学 Composé, matériau électroluminescent et élément électroluminescent organique

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN103570737A (zh) * 2012-07-25 2014-02-12 三星显示有限公司 杂环化合物，包含其的有机发光装置和有机发光显示器
KR20140074729A (ko) * 2012-12-10 2014-06-18 주식회사 두산 인돌로카바졸계 유기 화합물 및 이를 포함하는 유기 전계 발광 소자
WO2014092354A1 (fr) * 2012-12-10 2014-06-19 주식회사 두산 Composé organique et élément électroluminescent organique le comprenant
KR20140120090A (ko) * 2013-04-02 2014-10-13 에스에프씨 주식회사 유기발광 화합물 및 이를 포함하는 유기전계발광소자
WO2022030265A1 (fr) * 2020-08-07 2022-02-10 国立大学法人京都大学 Composé, matériau électroluminescent et élément électroluminescent organique
CN113429395A (zh) * 2021-07-27 2021-09-24 北京八亿时空液晶科技股份有限公司 咪唑衍生物、有机电致发光材料、发光元件及消费型产品

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