WO2023207375A1 - Composé azoté, élément électronique et dispositif électronique - Google Patents

Composé azoté, élément électronique et dispositif électronique Download PDF

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WO2023207375A1
WO2023207375A1 PCT/CN2023/081174 CN2023081174W WO2023207375A1 WO 2023207375 A1 WO2023207375 A1 WO 2023207375A1 CN 2023081174 W CN2023081174 W CN 2023081174W WO 2023207375 A1 WO2023207375 A1 WO 2023207375A1
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substituted
unsubstituted
carbon atoms
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nitrogen
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卫彤
岳富民
金荣国
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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
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/56—Ring systems containing three or more rings
    • C07D209/80—[b, c]- or [b, d]-condensed
    • C07D209/82—Carbazoles; Hydrogenated carbazoles
    • C07D209/88—Carbazoles; Hydrogenated carbazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the ring system
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
    • 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
    • H10K50/15—Hole transporting layers
    • 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
    • H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
    • 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
    • H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
    • H10K85/626—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene
    • 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
    • H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
    • H10K85/633—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom
    • 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
    • H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
    • H10K85/636—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising heteroaromatic hydrocarbons as substituents on the nitrogen atom
    • 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
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
    • 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
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6574—Polycyclic condensed heteroaromatic hydrocarbons comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
    • 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
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6576—Polycyclic condensed heteroaromatic hydrocarbons comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
    • Y02E10/00—Energy generation through renewable energy sources
    • Y02E10/50—Photovoltaic [PV] energy
    • Y02E10/549—Organic PV cells

Definitions

  • the present application relates to the field of organic light-emitting materials, and specifically provides a nitrogen-containing compound, electronic components and electronic devices.
  • OLED Organic Light Emission Diodes
  • the OLED photoelectric functional material film layer that constitutes the OLED device includes at least two or more layers of structure.
  • the OLED device structure used in industry includes a hole injection layer, a hole transport layer, an electron blocking layer, a light-emitting layer, a hole blocking layer, and an electron blocking layer.
  • There are various film layers such as transport layer and electron injection layer. That is to say, the optoelectronic functional materials used in OLED devices include at least hole injection materials, hole transport materials, luminescent materials, electron transport materials, etc. The types and combinations of materials are rich. characteristics of sex and diversity.
  • OLED display technology has been applied in smartphones, tablets and other fields, and will further expand to large-size applications such as TVs.
  • the luminous efficiency, service life and other properties of OLED devices Still needs further improvement.
  • Research on improving the performance of OLED light-emitting devices includes: reducing the driving voltage of the device, improving the luminous efficiency of the device, and increasing the service life of the device.
  • OLED optoelectronic functional materials to create higher-performance OLED functional materials.
  • organic OLED devices When organic OLED devices are used in display devices, the organic OLED devices are required to have long life and high efficiency.
  • blue light devices in the blue pixel area (compared with red and green light-emitting devices) have higher driving voltage and shorter lifespan.
  • the hole mobility and glass transition temperature of hole transport materials are increased, thereby extending the life of blue light devices and reducing device voltage.
  • the purpose of this application is to provide a nitrogen-containing compound, electronic components and electronic devices.
  • the nitrogen-containing compound of the present application can effectively improve the performance of electronic components.
  • the application provides a nitrogen-containing compound, the structure of the nitrogen-containing compound is shown in Formula I:
  • R 1 and R 2 are the same or different, and are each independently selected from an alkyl group with 1 to 10 carbon atoms, a cycloalkyl group with 3 to 10 carbon atoms, a substituted or substituted group with 6 to 25 carbon atoms.
  • L is selected from a substituted or unsubstituted arylene group with 6 to 18 carbon atoms, a substituted or unsubstituted heteroarylene group with 5 to 18 carbon atoms;
  • Ar is selected from a substituted or unsubstituted aryl group with 6 to 23 carbon atoms, a substituted or unsubstituted heteroaryl group with 5 to 23 carbon atoms;
  • R 1 , R 2 , L and Ar are the same or different, and are each independently selected from deuterium, cyano group, alkyl group with 1 to 10 carbon atoms, and deuterated alkyl group with 1 to 10 carbon atoms. base, aryl group with 6-12 carbon atoms, heteroaryl group with 5-12 carbon atoms, cycloalkyl group with 3-10 carbon atoms, alkoxy group with 1-10 carbon atoms or carbon Alkylthio group with atoms 1-10.
  • the present application provides an electronic component, including an anode, a cathode, and a functional layer disposed between the anode and the cathode, wherein the functional layer contains the nitrogen-containing compound described in the first aspect of the present application.
  • the present application provides an electronic device, including the electronic component described in the second aspect of the present application.
  • the nitrogen-containing compound of the present application is a triarylamine compound.
  • this triarylamine compound three aromatic groups are connected with the nitrogen atom as the center.
  • the first aromatic group is a 4-carbazolyl group
  • the second aromatic group It is a 4-carbazolyl group connected to the nitrogen atom through an aromatic group (L), and the third one is a small-volume aromatic group (Ar).
  • This combination of specific groups can make the different planes of the entire molecule have appropriate angles and form a stable spatial configuration, which not only improves the thermal stability of the compound, but also prevents the compound from crystallizing during evaporation.
  • this combination of groups also enables the compound to have a suitable HOMO energy level and helps to improve the carrier (hole) injection and transport capabilities of the compound.
  • Using the nitrogen-containing compound of the present application as a hole transport layer in an organic electroluminescent device can effectively improve the luminous efficiency of the device and extend the service life of the device.
  • Figure 1 is a schematic structural diagram of an organic electroluminescent device according to an embodiment of the present application.
  • Figure 2 is a schematic structural diagram of a photoelectric conversion device according to an embodiment of the present application.
  • FIG. 3 is a schematic diagram of an electronic device according to an embodiment of the present application.
  • FIG. 4 is a schematic diagram of an electronic device according to another embodiment of the present application.
  • Electron injection layer 100. Anode; 200. Cathode; 300. Functional layer; 310. Hole injection layer; 320. Hole transport layer; 321. Electron blocking layer; 330. Organic light-emitting layer; 340. Electron transport layer; 350. Electron injection layer ; 360: photoelectric conversion layer; 400: first electronic device; 500: second electronic device.
  • the application provides a nitrogen-containing compound, the structure of the nitrogen-containing compound is shown in Formula I:
  • R 1 and R 2 are the same or different, and are each independently selected from an alkyl group with 1 to 10 carbon atoms, a cycloalkyl group with 3 to 10 carbon atoms, a substituted or substituted group with 6 to 25 carbon atoms.
  • L is selected from a substituted or unsubstituted arylene group with 6 to 18 carbon atoms, a substituted or unsubstituted heteroarylene group with 5 to 18 carbon atoms;
  • Ar is selected from a substituted or unsubstituted aryl group with 6 to 23 carbon atoms, a substituted or unsubstituted heteroaryl group with 5 to 23 carbon atoms;
  • R 1 , R 2 , L and Ar are the same or different, and are each independently selected from deuterium, cyano group, alkyl group with 1 to 10 carbon atoms, Deuterated alkyl group with 1 to 10 carbon atoms, aryl group with 6 to 12 carbon atoms, heteroaryl group with 5 to 12 carbon atoms, cycloalkyl group with 3 to 10 carbon atoms, carbon atoms Alkoxy group with 1-10 carbon atoms or alkylthio group with 1-10 carbon atoms.
  • each... is independently selected from and “... is independently selected from” are interchangeable and should be understood in a broad sense. They can refer to the same symbol in different groups. The specific options expressed between them do not affect each other. It can also be expressed that in the same group, the specific options expressed by the same symbols do not affect each other. For example, “ Among them, each q is independently selected from 0, 1, 2 or 3, and each R" is independently selected from hydrogen, deuterium, fluorine, and chlorine. The meaning is: Formula Q-1 represents that there are q substituents R on the benzene ring.
  • each R can be the same or different, and the options of each R" do not affect each other;
  • Formula Q-2 indicates that 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 R c ).
  • substituted or unsubstituted aryl refers to an aryl group having a substituent Rc or an unsubstituted aryl group.
  • the above-mentioned substituent, namely R c may be, for example, deuterium, cyano group, heteroaryl group, aryl group, alkyl group, deuterated alkyl group, cycloalkyl group, alkoxy group, alkylthio group, etc.
  • the two substituents R c can exist independently or be connected to each other to form a ring with the atom; when there are two adjacent substituents R c on the functional group
  • the two adjacent substituents R c may exist independently or be fused into a ring with the functional group to which they are connected. It is preferred that the two adjacent substituents R c exist independently.
  • the number of carbon atoms of a substituted or unsubstituted functional group refers to the number of all carbon atoms.
  • 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.
  • Ring aryl groups monocyclic aryl groups conjugated through carbon-carbon bonds and fused-ring aryl groups, two or more fused-ring aryl groups conjugated through carbon-carbon bonds.
  • 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. It should be noted that both biphenyl and terphenyl groups are regarded as aryl groups in this application.
  • aryl groups include, but are not limited to, phenyl, naphthyl, fluorenyl, anthracenyl, phenanthrenyl, biphenyl, terphenyl, benzo[9,10]phenanthrenyl, pyrenyl, benzofluoranthenyl , Key et al.
  • the substituted aryl group may be one or more than two hydrogen atoms in the aryl group substituted by deuterium, cyano, aryl, heteroaryl, alkyl, cycloalkyl, deuterated alkyl, alkyl, etc. Substituted with oxygen, alkylthio and other groups.
  • 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 a carbon number of 18 refers to the aryl group and the substituted aryl group.
  • the total number of carbon atoms in the base is 18.
  • heteroaryl refers to a monovalent aromatic ring or its derivatives containing 1, 2, 3, 4, 5, 6 or more heteroatoms in the ring.
  • the heteroatom can be B , at least one of O, N, P, Si, 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 include thienyl, furyl, pyrrolyl, imidazolyl, thiazolyl, oxazolyl, oxadiazolyl, triazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, acridine Aldyl, pyridazinyl, pyrazinyl, quinolinyl, quinazolinyl, quinoxalinyl, phenoxazinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazine base, isoquinolyl, indolyl, carbazolyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothienyl, dibenzothienyl, thieno Thienyl, benzofuranyl,
  • the substituted heteroaryl group may be one or more than two hydrogen atoms in the heteroaryl group substituted by, for example, deuterium, cyano, aryl, heteroaryl, alkyl, cycloalkyl, deuterated alkyl , alkoxy, alkylthio and other groups substituted. 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.
  • non-located connecting bonds refer to single bonds protruding from the ring system. 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 phenanthrene 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, which represents Meaning, including any possible connection method shown in formula (X'-1) to formula (X'-4):
  • a non-positioned substituent in this application refers to a substituent connected through a single bond extending from the center of the ring system, which means that the substituent can be connected at any possible position in the ring system.
  • the substituent R' represented by the formula (Y) is connected to the quinoline ring through a non-positioned bond, and its meaning includes formula (Y-1) ⁇ Any possible connection method shown in formula (Y-7):
  • alkyl groups with 1 to 10 carbon atoms include linear alkyl groups with 1 to 10 carbon atoms and branched chain alkyl groups with 3 to 10 carbon atoms.
  • the number of carbon atoms can be 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10.
  • alkyl groups with 1 to 10 carbon atoms include, but are not limited to, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl base, neopentyl, cyclopentyl, n-hexyl, heptyl, n-octyl, 2-ethylhexyl, nonyl, decyl, 3,7-dimethyloctyl, etc.
  • the number of carbon atoms of the aryl group as a substituent may be 6-12, and the number of carbon atoms is, for example, 6, 10 or 12, etc.
  • Specific examples of the aryl group as a substituent include, but are not limited to, phenyl, Naphthyl, biphenyl.
  • the number of carbon atoms of the heteroaryl group as a substituent may be 5-12, and the number of carbon atoms is, for example, 5, 8, 9, 10 or 12, etc.
  • Specific examples of the heteroaryl group as a substituent include but It is not limited to pyridyl group, quinolyl group, dibenzofuranyl group, dibenzothienyl group, carbazolyl group, etc.
  • the number of carbon atoms of the cycloalkyl group as a substituent may be 3-10, preferably 5-8.
  • Specific examples of cycloalkyl include, but are not limited to, cyclopentyl, cyclohexyl, and the like.
  • the number of carbon atoms of the deuterated alkyl group as a substituent may be 1-10, preferably 1-4.
  • Specific examples of deuterated alkyl groups include, but are not limited to: trideuterated methyl.
  • R 1 and R 2 can each be independently selected from an alkyl group with 1, 2, 3, 4, 5 or 6 carbon atoms, a ring group with 4, 5, 6, 7 or 8 carbon atoms.
  • R 1 and R 2 are the same or different, and are each independently selected from an alkyl group with a carbon number of 1-5, a cycloalkyl group with a carbon number of 5-8, a cycloalkyl group with a carbon number of 6 -18 substituted or unsubstituted aryl group, and substituted or unsubstituted heteroaryl group with 5 to 18 carbon atoms.
  • R 1 and R 2 are the same or different, and are each independently selected from an alkyl group with 1 to 4 carbon atoms, a cycloalkyl group with 5 to 8 carbon atoms, and an alkyl group with 6 to 15 carbon atoms.
  • R 1 and R 2 are the same or different, and are each independently selected from methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopentyl base, cyclohexyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted terphenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted Substituted phenanthrenyl, substituted or unsubstituted pyridyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothienyl, substituted or unsubstituted carbazolyl.
  • the substituents in R 1 and R 2 are the same or different, and are each independently selected from deuterium, cyano group, alkyl group with 1 to 4 carbon atoms, and deuterated alkyl group with 1 to 4 carbon atoms. group, an aryl group with 6 to 10 carbon atoms, a cycloalkyl group with 5 to 8 carbon atoms, an alkoxy group with 1 to 4 carbon atoms, or an alkylthio group with 1 to 4 carbon atoms.
  • R 1 and R 2 are each independently selected from deuterium, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, trideuterated methyl, phenyl, Naphthyl, cyclopentyl or cyclohexyl.
  • R 1 and R 2 are each independently selected from methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopentyl, cyclohexyl, Substituted or unsubstituted group 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, and the substituents are each independently selected from deuterium, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, and trideuterated methyl. , phenyl, naphthyl; when the number of substituents is greater than 1, each substituent may be the same or different.
  • R 1 and R 2 are each independently selected from the group consisting of methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl and the following groups:
  • R 1 and R 2 are each independently selected from the group consisting of methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl and the following groups:
  • L is selected from a substituted or unsubstituted arylene group having 6 to 12 carbon atoms, and a substituted or unsubstituted heteroarylene group having 5 to 12 carbon atoms.
  • L can be selected from: substituted or unsubstituted arylene groups with carbon atoms of 6, 7, 8, 9, 10, 11, 12, or selected from the group consisting of carbon atoms of 5, 6, 7, 8, 9 , 10, 11, 12 substituted or unsubstituted heteroarylene groups.
  • L is selected from substituted or unsubstituted arylene groups having 6 to 12 carbon atoms.
  • L is selected from substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted biphenylene, substituted or unsubstituted pyridylene, substituted or unsubstituted Substituted dibenzofurylene, substituted or unsubstituted dibenzothienylene.
  • L is selected from substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene, and substituted or unsubstituted biphenylene.
  • each substituent in L is independently selected from deuterium, cyano group, alkyl group having 1-4 carbon atoms, deuterated alkyl group having 1-4 carbon atoms or phenyl group.
  • each substituent in L is independently selected from deuterium, cyano, methyl, ethyl, isopropyl, tert-butyl, trideuterated methyl or phenyl.
  • L is selected from the group consisting of:
  • Ar can be selected from a substituted or unsubstituted aryl group with 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19 or 20 carbon atoms.
  • Substituted or unsubstituted heteroaryl groups with 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17 or 18 atoms.
  • Ar is selected from the group consisting of substituted or unsubstituted aryl groups having 6 to 18 carbon atoms, and substituted or unsubstituted heteroaryl groups having 5 to 18 carbon atoms.
  • Ar is selected from a substituted or unsubstituted aryl group having 6 to 15 carbon atoms, and a substituted or unsubstituted heteroaryl group having 12 to 15 carbon atoms.
  • Ar is selected from substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted fluorenyl , substituted or unsubstituted terphenyl, substituted or unsubstituted pyridyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothienyl, substituted or unsubstituted carbazolyl.
  • the substituents in Ar are each independently selected from deuterium, cyano group, alkyl group having 1-4 carbon atoms, deuterated alkyl group having 1-4 carbon atoms, and 6-10 carbon atoms.
  • the substituents in Ar are each independently selected from deuterium, cyano, methyl, ethyl, isopropyl, tert-butyl, trideuterated methyl, phenyl, naphthyl, pyridyl, di Benzofuryl, dibenzothienyl or carbazolyl.
  • Ar is selected from the group consisting of:
  • Ar is selected from the group consisting of:
  • Ar is selected from a substituted or unsubstituted aryl group with 6 to 15 carbon atoms, and a substituted or unsubstituted heteroaryl group with 12 to 15 carbon atoms.
  • the nitrogen-containing compound serving as a hole transport layer can further improve the overall performance of the organic electroluminescent device.
  • the definitions of R 1 and R 2 in Formula IA are as shown above.
  • the nitrogen-containing compound is selected from the group consisting of:
  • the synthesis method of the nitrogen-containing compound provided in this application is not particularly limited. Those skilled in the art can determine the appropriate synthesis method based on the preparation method provided in the synthesis examples section of the nitrogen-containing compound in this application. In other words, the Synthesis Examples section of this application exemplarily provides methods for preparing nitrogen-containing compounds, and the raw materials used can be obtained commercially or by methods well known in the art. Those skilled in the art can obtain all nitrogen-containing compounds provided in this application based on these exemplary preparation methods. All specific preparation methods for preparing the nitrogen-containing compounds will not be described in detail here. Those skilled in the art should not understand that this application is limit.
  • a second aspect of the present application provides an electronic component, including an anode, a cathode, and a functional layer 100 disposed between the anode and the cathode, wherein the functional layer includes the nitrogen-containing compound described in the first aspect of the present application. compound.
  • the functional layer includes a hole transport layer containing the nitrogen-containing compound of the present application.
  • the electronic component may be an organic electroluminescent device or a photoelectric conversion device.
  • the electronic component is an organic electroluminescent device.
  • the organic electroluminescent device includes an anode 100 , a hole transport layer 320 , an organic light-emitting layer 330 , an electron transport layer 340 and a cathode 200 which are stacked in sequence.
  • the anode 100 includes an anode material, which is preferably a material with a large work function that facilitates hole injection into the functional layer.
  • anode materials include: metals such as nickel, platinum, vanadium, chromium, copper, zinc and gold or 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 not limited thereto.
  • a transparent electrode including indium tin oxide (ITO) as an anode is included.
  • the hole transport layer 320 contains the nitrogen-containing compound of the present application.
  • an electron blocking layer 321 (also called a "hole adjustment layer”) is disposed between the hole transport layer 320 and the organic light-emitting layer 330.
  • the material of the electron blocking layer 321 may be selected from carbazole polymers, carbazole-linked aromatic amine compounds, dibenzofuran-linked aromatic amine compounds, substituted fluorenyl-linked triarylamine compounds, or other types of compounds. This application does not impose any special limitations on this.
  • the material of the electron blocking layer is selected from at least one of the following compounds:
  • the material of the electron blocking layer 321 is EB-1.
  • the organic light-emitting layer 330 may be composed of a single light-emitting material, or may include a host material and a guest material (also called a "dopant").
  • the organic light-emitting layer 330 is composed of a host material and a guest material.
  • the holes injected into the organic light-emitting layer 330 and the electrons injected into the organic light-emitting layer 330 can recombine in the organic light-emitting layer 330 to form excitons, and the excitons transfer energy.
  • the host material transfers energy to the guest material, thereby enabling the guest material to emit light.
  • the main material of the organic light-emitting layer 330 may be metal chelate compounds, bistyryl derivatives, aromatic amine derivatives, dibenzofuran derivatives, anthracene derivatives or other types of materials. This application does not Make special restrictions.
  • the host material is selected from one or more than two of the following compounds:
  • the host material of the organic light-emitting layer 330 is BH-1.
  • the guest material of the organic light-emitting layer 330 may be a compound with a condensed aryl ring or a derivative thereof, a compound with a heteroaryl ring or a derivative thereof, a bisarylamine derivative with a condensed aromatic subunit, or other materials.
  • the guest material is selected from at least one of the following compounds:
  • the guest material of the organic light emitting layer 330 is composed of BD-1.
  • the electron transport layer 340 may be a single-layer structure or a multi-layer structure, and may include one or more electron transport materials.
  • the electron transport materials may generally include metal complexes and/or nitrogen-containing heterocyclic derivatives, where , the metal complex material can be selected from, for example LiQ, Alq 3 , Bepq 2 , etc.; the nitrogen-containing heterocyclic derivative can be an aromatic ring with a nitrogen-containing six-membered ring or a five-membered ring skeleton, a condensed aromatic ring with a nitrogen-containing six-membered ring or a five-membered ring skeleton. Specific examples include, but are not limited to, 1,10-phenanthroline compounds such as BCP, Bphen, NBphen, DBimiBphen, BimiBphen, etc., or at least one of the following compounds:
  • electron transport layer 340 is composed of ET-5 and LiQ.
  • the cathode 200 includes a cathode material, which is a material with a small work function that facilitates the injection of electrons 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. It is preferred to include a metal electrode containing magnesium and silver as the cathode.
  • a hole injection layer 310 is also provided between the anode 100 and the hole transport layer 320 to enhance the ability to inject holes into the hole transport layer 320 .
  • the hole injection layer 310 can be made of benzidine derivatives, starburst arylamine compounds, phthalocyanine derivatives or other materials, which are not particularly limited in this application.
  • hole injection layer 310 is selected from the group consisting of:
  • the hole injection layer 310 is composed of HAT-CN.
  • an electron injection layer 350 is also provided between the cathode 200 and the electron transport layer 340 to enhance the ability to inject electrons into the electron transport layer 340 .
  • the electron injection layer 350 may include an inorganic material such as an alkali metal sulfide or an alkali metal halide, or may include a complex of an alkali metal and an organic substance.
  • the electron injection layer 350 contains LiQ or Yb.
  • the organic electroluminescent device may be a blue light device, a red light device or a green light device, preferably a blue light device.
  • the electronic component is a photoelectric conversion device.
  • the photoelectric conversion device may include an anode 100 , a hole transport layer 320 , a photoelectric conversion layer 360 , an electron transport layer 340 and a cathode 200 that are stacked in sequence.
  • the hole transport layer 320 contains the nitrogen-containing compound of the present application.
  • the photoelectric conversion device is a solar cell, such as an organic thin film solar cell.
  • 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 is a first electronic device 400
  • the first electronic device 400 includes the above-mentioned organic electroluminescent device.
  • the first electronic device 400 may be, for example, a display device, a lighting device, an optical communication device, or other types of electronic devices, and 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 electronic device is a second electronic device 500
  • the second electronic device 500 includes the above-mentioned photoelectric conversion device.
  • the second electronic device 500 may be, for example, a solar power generation device, a light detector, a fingerprint identification device, an optical module, a CCD camera, or other types of electronic devices.
  • the compounds of the synthetic methods not mentioned in this application are all commercially available raw material products.
  • IM I-X was synthesized according to the synthesis method of IM 1-A. The difference is that the raw material 1 in Table 1 is used instead of iodobenzene. The obtained intermediate product IM I-X and its yield are shown in Table 1.
  • IM I-I was synthesized according to the synthesis method of IM I-H. The difference is that the raw material 2 in Table 2 is used instead of ethyl iodide. The obtained intermediate product IM I-I and its yield are shown in Table 2.
  • Example 1 Blue organic electroluminescent device
  • the anode is prepared by the following process: the thickness is
  • the ITO/Ag/ITO substrate is cut into a size of 40mm (length) ⁇ 40mm (width) ⁇ 0.7mm (thickness), and the photolithography process is used to prepare it into an experimental substrate with cathode, anode and insulating layer patterns, and can Use ultraviolet ozone and O 2 :N 2 plasma for surface treatment to increase the work function of the anode, and use organic solvents to clean the surface of the ITO substrate to remove impurities and oil stains on the surface of the ITO substrate.
  • HAT-CN was vacuum evaporated on the experimental substrate (anode) to form a thickness of hole injection layer (HIL), and then vacuum evaporate compound A12 on the hole injection layer to form a thickness of hole transport layer.
  • HIL hole injection layer
  • compound BH-1 host
  • compound BD-1 dopant
  • the compound ET-5 and LiQ were co-evaporated at a weight ratio of 1:1 to form Thick electron transport layer (ETL), Yb is evaporated on the electron transport layer to form a thickness of Electron injection layer (EIL), and then magnesium (Mg) and silver (Ag) are vacuum evaporated together on the electron injection layer at an evaporation rate of 1:9 to form a thickness of the cathode.
  • ETL Thick electron transport layer
  • EIL Electron injection layer
  • Mg magnesium
  • Ag silver
  • CPL organic coating layer
  • An organic electroluminescent device was prepared using the same method as in Example 1, except that when preparing the hole transport layer, the remaining compounds listed in Table 6 were used instead of compound A12 in Example 1.
  • the hole transport layer was prepared using the same method as in Example 1, except that in Comparative Examples 1 to 4, Compound A, Compound B, Compound C and Compound D were used instead of Compound A12 in Example 1. Organic electroluminescent devices.
  • the structures of the main materials used to prepare organic electroluminescent devices are as follows:
  • the performance of the blue organic electroluminescent devices prepared in Examples 1-32 and Comparative Examples 1-4 was tested. Specifically, the IVL performance of the device was tested under the condition of 10mA/ cm2 . The T95 device life was at 15mA/ cm2. The test was carried out under the conditions, and the test results are shown in Table 6 below.
  • using the nitrogen-containing compound of the present application as a hole transport layer in an organic electroluminescent device can further improve the luminous efficiency and service life of the device while maintaining a low driving voltage of the device.

Abstract

La présente invention concerne un composé azoté, un élément électronique et un dispositif électronique. Le composé azoté a une structure représentée par la formule I et peut améliorer les performances d'éléments électroniques.
PCT/CN2023/081174 2022-04-28 2023-03-13 Composé azoté, élément électronique et dispositif électronique WO2023207375A1 (fr)

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CN114989069B (zh) * 2022-04-28 2023-10-10 陕西莱特光电材料股份有限公司 含氮化合物和电子元件及电子装置

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