WO2022206389A1 - Composé contenant de l'azote, composant électronique le comprenant et dispositif électronique - Google Patents

Composé contenant de l'azote, composant électronique le comprenant et dispositif électronique Download PDF

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WO2022206389A1
WO2022206389A1 PCT/CN2022/081201 CN2022081201W WO2022206389A1 WO 2022206389 A1 WO2022206389 A1 WO 2022206389A1 CN 2022081201 W CN2022081201 W CN 2022081201W WO 2022206389 A1 WO2022206389 A1 WO 2022206389A1
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substituted
group
unsubstituted
carbon atoms
nitrogen
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PCT/CN2022/081201
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Chinese (zh)
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马天天
杨敏
南朋
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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
    • H10K85/631—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 materials, and in particular, to a nitrogen-containing compound and electronic components and electronic devices containing the same.
  • Organic light-emitting diodes have the advantages of DC voltage driving, active light emission, small size, wide viewing angle, fast response speed, bright colors and simple production process, and have broad application prospects in the future display field.
  • the electron blocking layer is used to block the electrons transmitted from the organic light-emitting layer, thereby ensuring that the electrons and holes can be efficiently recombined in the organic light-emitting layer; at the same time, the electron blocking layer can also prevent the organic light-emitting layer from diffusing.
  • the excitons can reduce the triplet quenching of the excitons, thereby ensuring the luminous efficiency of the organic electroluminescent device.
  • the compound of the electron blocking layer has a relatively high LUMO value, which can effectively block the transport and diffusion of electrons and excitons from the organic light-emitting layer to the anode direction.
  • Organic hole transport materials mainly include compounds such as carbazoles, triarylamines, styrenes and butadiene.
  • triarylamines have the characteristics of high hole mobility and good electrochemical performance, and have been used as OLED holes. Transmission materials and luminescent materials are widely studied and applied.
  • Triarylamines are centered on nitrogen atoms and have a propeller structure. Their large steric hindrance and hyperconjugation effect promote the high stability of nitrogen atom radicals. This unique free radical property makes triphenylamines more stable. Compounds have high hole mobility.
  • the present application provides a nitrogen-containing compound and an electronic component and electronic device including the same, wherein the nitrogen-containing compound can improve the performance of the electronic component.
  • a nitrogen-containing compound is provided, and the structure of the nitrogen-containing compound is shown in formula 1:
  • 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 25 carbon atoms, and a substituted or unsubstituted arylene group having 3 to 25 carbon atoms. substituted heteroarylene;
  • Ar 1 , Ar 2 and Ar 3 are the same or different, and are independently selected from substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, and substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms. ;
  • the substituents in L, L 1 , L 2 , Ar 1 , Ar 2 and Ar 3 are the same or different, and are independently selected from deuterium, halogen, cyano, heteroaryl with 3 to 18 carbon atoms, carbon An aryl group having 6 to 18 atoms, a trialkylsilyl group having 3 to 12 carbon atoms, an alkyl group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, or a carbon number of 3-10 cycloalkyl groups; optionally, two adjacent substituents form a ring.
  • an electronic component comprising an anode, a cathode, and a functional layer between the anode and the cathode, the functional layer comprising the nitrogen-containing compound described in the first aspect of the present application.
  • an electronic device including the electronic component described in the second aspect of the present application.
  • the nitrogen-containing compounds provided by the present application have triarylamine and biscarbazole structures, and the triarylamine compounds have good electricity donating properties and can form ammonium cations under the action of an electric field.
  • the compounds have lower ionization potential and higher good hole mobility and good photostability.
  • carbazole is an electron-rich nitrogen-containing heterocyclic structure, with one of the carbazolyl groups (referred to as "carbazolyl A”) as the center, and its N atom is connected to the 1st position of the other carbazolyl group.
  • the benzene ring of carbazolyl A is connected to the triarylamine structure, so that the entire molecular structure is easily functionally modified in part of the active site of carbazolyl A due to its special rigid structure.
  • a natural hole transport material A natural hole transport material.
  • the introduction of the biscarbazole group with a specific linking position on the triarylamine structure can more effectively realize the effective matching between the transport material and the charge generating material, and at the same time improve the solubility of the compound and improve its thermal stability.
  • Applying the nitrogen-containing compound of the present application to an organic electroluminescent device (OLED) can effectively improve the luminous efficiency and service life of the device under the condition that the device has a lower driving voltage.
  • FIG. 1 is a schematic structural diagram of an organic electroluminescent device according to an embodiment of the present application.
  • FIG. 2 is a schematic structural diagram of a first electronic device according to an embodiment of the present application.
  • FIG. 3 is a schematic structural diagram of a photoelectric conversion device according to an embodiment of the present application.
  • FIG. 4 is a schematic structural diagram of a second electronic device according to an embodiment of the present application.
  • each q is independently selected from 0, 1, 2 or 3, and each R" is independently selected from hydrogen, deuterium, fluorine, chlorine", and its meaning is:
  • formula Q-1 represents that there are q substituents R on the benzene ring ", each R” can be the same or different, and the options of each R" do not affect each other;
  • formula Q-2 indicates that each benzene ring of biphenyl has q substituents R", and the two benzene rings have q substituents R".
  • the number q of R" substituents may be the same or different, and each R" may be the same or different, and the options of each R" do not affect each other.
  • the terms “optional” and “optionally” mean that the subsequently described event or circumstance can, but need not, occur, and that the description includes instances where the event or circumstance does or does not occur.
  • “optionally, two adjacent substituents form a ring” means that the two substituents may form a ring but need not form a ring, including: the situation where two adjacent substituents form a ring and the adjacent A scenario where the two substituents do not form a ring.
  • substituted or unsubstituted means that the functional group described after the term may or may not have a substituent (hereinafter, for the convenience of description, the substituents are collectively referred to as R c ), if there is a substitution In the case of a group, the number of substituents may be one or plural.
  • substituted or unsubstituted aryl refers to an aryl group having one or more substituents Rc or an unsubstituted aryl group.
  • the above-mentioned substituent, ie R c can be, for example, deuterium, halogen group, cyano group, heteroaryl group, aryl group, trialkylsilyl group, alkyl group, haloalkyl group, cycloalkyl group and the like.
  • the two substituent groups R c may exist independently or be connected to each other to form a ring with the atom; when there are two adjacent substituent groups R c on the functional group
  • the adjacent substituents R c can exist independently or be condensed with the functional group to which they are connected to form a ring.
  • the number of carbon atoms of a substituted or unsubstituted functional group refers to the number of all carbon atoms. For example, if Ar 1 is a substituted aryl group having 12 carbon atoms, then all carbon atoms of the aryl group and the substituents thereon are 12.
  • aryl refers to an optional functional group or substituent derived from an aromatic carbocyclic ring.
  • Aryl groups can be monocyclic aryl groups (eg, phenyl) or polycyclic aryl groups, in other words, aryl groups can be monocyclic aryl groups, fused-ring aryl groups, two or more monocyclic aryl groups conjugated through carbon-carbon bonds. Cyclic aryl groups, monocyclic aryl groups and fused-ring aryl groups linked by carbon-carbon bond conjugation, two or more fused-ring aryl groups linked by carbon-carbon bond conjugation. That is, unless otherwise specified, two or more aromatic groups linked by carbon-carbon bond conjugation may also be considered aryl groups in the present application.
  • the fused ring aryl group may include, for example, a bicyclic fused aryl group (eg, naphthyl), a tricyclic fused aryl group (eg, phenanthrenyl, fluorenyl, anthracenyl), and the like.
  • the aryl group does not contain heteroatoms such as B, N, O, S, P, Se and Si. It should be noted that both biphenyl and fluorenyl are regarded as aryl groups in this application.
  • aryl groups may include, but are not limited to, phenyl, naphthyl, fluorenyl, anthracenyl, phenanthryl, biphenyl, terphenyl, benzo[9,10]phenanthryl, pyrenyl, benzofluoranthene base, Base et al.
  • a substituted aryl group may be one or more than two hydrogen atoms in the aryl group replaced by a group such as deuterium, halogen group, cyano, aryl, heteroaryl, trialkylsilyl, haloalkyl, Alkyl, cycloalkyl and other groups are substituted.
  • the number of carbon atoms in a substituted aryl group refers to the total number of carbon atoms in the aryl group and the substituents on the aryl group, for example, a substituted aryl group with a carbon number of 18 refers to the aryl group and its substituents. The total number of carbon atoms of the substituents is 18.
  • the fluorenyl group may be substituted, and when there are two substituent groups, the two substituent groups may combine with each other to form a spiro structure.
  • substituted fluorenyl groups include, but are not limited to,
  • heteroaryl refers to a monovalent aromatic ring or a derivative thereof containing 1, 2, 3, 4, 5, 6 or more heteroatoms in the ring, and the heteroatoms can be B, O, N, P At least one of , Si, Se, and S.
  • a heteroaryl group can be a monocyclic heteroaryl group or a polycyclic heteroaryl group, in other words, a heteroaryl group can be a single aromatic ring system or multiple aromatic ring systems linked by carbon-carbon bonds, and any aromatic
  • the ring system is an aromatic monocyclic ring or an aromatic fused ring.
  • heteroaryl groups can include thienyl, furyl, pyrrolyl, imidazolyl, thiazolyl, oxazolyl, oxadiazolyl, triazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, acridinyl, pyridazinyl, pyrazinyl, quinolinyl, quinazolinyl, quinoxalinyl, phenoxazinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl Azinyl, isoquinolinyl, indolyl, carbazolyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothienyl, dibenzothienyl, thiophene thieny
  • heteroarylene group refers to a divalent or higher valent group formed by the further loss of one or more hydrogen atoms from the heteroaryl group.
  • a substituted heteroaryl group may be a heteroaryl group where one or more than two hydrogen atoms are replaced by groups such as deuterium, halogen, cyano, aryl, heteroaryl, trialkylsilyl, alkane substituted by groups such as radicals, cycloalkyls, etc. It should be understood that the number of carbon atoms in a substituted heteroaryl group refers to the total number of carbon atoms in the heteroaryl group and the substituents on the heteroaryl group.
  • a non-positioned connecting bond refers to a single bond extending from the ring system It means that one end of the linking bond can be connected to any position in the ring system through which the bond runs, 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 linkages running through the bicyclic ring. -1) to any possible connection method shown in formula (f-10).
  • the phenanthrene represented by the formula (X') is connected to other positions of the molecule through a non-positioned link extending from the middle of one side of the benzene ring, which represents The meaning of , includes any possible connection modes shown by formula (X'-1) to formula (X'-4).
  • a non-positioned substituent in the present application refers to a substituent attached through a single bond extending from the center of the ring system, which means that the substituent may be attached 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-positioning link, and the meanings represented by the formula (Y-1) to Any possible connection mode shown by formula (Y-7).
  • the number of carbon atoms in the alkyl group may be 1-10, specifically 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10, and the alkyl group may include straight-chain alkyl groups and branched-chain alkyl groups. Alkyl.
  • alkyl groups include, but are not limited to, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl, cyclopentyl, n-hexyl , heptyl, n-octyl, 2-ethylhexyl, nonyl, decyl, 3,7-dimethyloctyl, etc.
  • halogen groups may include fluorine, iodine, bromine, chlorine, and the like.
  • the number of carbon atoms of the aryl group as a substituent may be 6-18, and the number of carbon atoms is specifically 6, 10, 12, 13, 14, 15, etc.
  • Specific examples of the aryl group include, but are not limited to, Phenyl, naphthyl, biphenyl, phenanthryl, anthracenyl, etc.
  • the number of carbon atoms of the heteroaryl group as a substituent may be 3 to 18, and the number of carbon atoms is, for example, 3, 4, 5, 8, 9, 10, 12, 13, 14, 15, etc.
  • Specific examples of aryl groups include, but are not limited to, pyridyl, quinolyl, dibenzofuranyl, dibenzothienyl, carbazolyl, and the like.
  • the number of carbon atoms of the trialkylsilyl group as a substituent may be 3 to 12, such as 3, 6, 7, 8, 9, etc. Specific examples thereof include, but are not limited to, trimethylsilyl , ethyldimethylsilyl, triethylsilyl, etc.
  • the number of carbon atoms of the cycloalkyl group as a substituent may be 3-10, for example, 5-10 or 5-8, and specific examples include, but are not limited to, cyclopentyl, cyclohexyl, adamantyl, etc. .
  • haloalkyl examples include, but are not limited to, trifluoromethyl.
  • the present application provides a nitrogen-containing compound, the structure of which is shown in formula 1:
  • 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 25 carbon atoms, and a substituted or unsubstituted arylene group having 3 to 25 carbon atoms. substituted heteroarylene;
  • Ar 1 , Ar 2 and Ar 3 are the same or different, and are independently selected from substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, and substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms. ;
  • the substituents in L, L 1 , L 2 , Ar 1 , Ar 2 and Ar 3 are the same or different, and are independently selected from deuterium, halogen, cyano, heteroaryl with 3 to 18 carbon atoms, carbon An aryl group having 6 to 18 atoms, a trialkylsilyl group having 3 to 12 carbon atoms, an alkyl group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, or a carbon number of 3-10 cycloalkyl groups; optionally, two adjacent substituents form a ring.
  • the nitrogen-containing compound has the structure shown below:
  • the substituents in L, L 1 , L 2 , Ar 1 , Ar 2 and Ar 3 are independently selected from deuterium, fluorine, cyano, heteroaryl with 5 to 12 carbon atoms, carbon atoms Aryl with 6 to 15 carbon atoms, trialkylsilyl group with 3 to 7 carbon atoms, alkyl group with 1 to 5 carbon atoms, haloalkyl group with 1 to 5 carbon atoms or 5 carbon atoms ⁇ 10 cycloalkyl; optionally, two adjacent substituents form a 5-13 membered saturated or unsaturated ring.
  • L, L 1 and L 2 are each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 18 carbon atoms, and a substituted or unsubstituted arylene group having 5 to 15 carbon atoms.
  • Heteroaryl are each independently selected from a single bond, or selected from substituted or unsubstituted carbon atoms having 6, 7, 8, 9, 10, 12, 14, 15, 16, 17, and 18 carbon atoms.
  • the substituents in L, L 1 and L 2 are selected from deuterium, fluorine, cyano, alkyl with 1 to 4 carbon atoms, trialkylsilyl with 3 to 7 carbon atoms, carbon A haloalkyl group having 1 to 4 atoms, an aryl group having 6 to 12 carbon atoms, or a cycloalkyl group having 5 to 8 carbon atoms.
  • the substituents in L, L 1 , L 2 are selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, phenyl, naphthyl, cyclopentyl, Cyclohexyl, trifluoromethyl or trimethylsilyl.
  • L, L and L are independently selected from single bond, substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted biphenylene, substituted or unsubstituted Substituted dibenzofuranylene group, substituted or unsubstituted dibenzothienylene group, substituted or unsubstituted fluorenylene group, or a divalent group selected from the group consisting of at least two of the above-mentioned groups connected to each other through a single bond group.
  • L is selected from a single bond, or from a substituted or unsubstituted group V, and the unsubstituted group V is selected from the group consisting of:
  • the substituted group V has one or more substituents, each of which is independently selected from deuterium, cyano, fluorine, methyl, ethyl, isopropyl, tert-butyl, phenyl, naphthalene group, cyclopentyl, cyclohexyl, trimethylsilyl or trifluoromethyl; when the number of substituents is greater than 1, the substituents are the same or different.
  • L is selected from single bond or the group that the following groups are formed:
  • L 1 and L 2 are each independently selected from a single bond, a substituted or unsubstituted aryl group having 6 to 12 carbon atoms.
  • L 1 and L 2 are each independently selected from single bond, substituted or unsubstituted phenylene.
  • the substituents in L 1 and L 2 are each independently selected from deuterium, fluorine, cyano, alkyl with 1 to 4 carbon atoms or phenyl.
  • L 1 and L 2 are each independently selected from the group consisting of a single bond or the following groups:
  • Ar 1 , Ar 2 and Ar 3 are each independently selected from substituted or unsubstituted aryl groups with 6-25 carbon atoms, or substituted or unsubstituted heteroaryl groups with 5-25 carbon atoms .
  • Ar 1 , Ar 2 and Ar 3 are each independently selected from the group consisting of 6, 7, 8, 9, 10, 12, 13, 14, 15, 16, 17, 18, 20, 21, 22, 23 carbon atoms , 24 or 25 substituted or unsubstituted aryl groups, or selected from the group consisting of 5, 6, 7, 8, 9, 10, 12, 13, 14, 15, 16, 17, 18, 20, 21, Substituted or unsubstituted heteroaryl of 22, 23, 24 or 25.
  • Ar 1 , Ar 2 and Ar 3 are each independently selected from Ar 1 , Ar 2 and Ar 3 are each independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted Substituted naphthyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothienyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted phenanthrene base.
  • the substituents in Ar 1 , Ar 2 and Ar 3 are each independently selected from deuterium, fluorine, cyano, aryl with 6-12 carbon atoms, and heteroaryl with 5-12 carbon atoms , an alkyl group with 1 to 5 carbon atoms, a trialkylsilyl group with 3 to 7 carbon atoms, a haloalkyl group with 1 to 4 carbon atoms or a cycloalkyl group with 5 to 10 carbon atoms; any Optionally, two adjacent substituents form a 5-13 membered saturated or unsaturated ring.
  • the substituents in Ar 1 , Ar 2 and Ar 3 are each independently selected from deuterium, cyano, fluorine, methyl, ethyl, n-propyl, isopropyl, tert-butyl, phenyl, biphenyl , naphthyl, cyclopentyl, cyclohexyl, carbazolyl, dibenzofuranyl, dibenzothienyl, pyridyl, quinolyl, trimethylsilyl or trifluoromethyl; optionally, phase
  • the adjacent two substituents form a 5- to 13-membered saturated or unsaturated ring (for example, a cyclopentane, cyclohexane or fluorene ring).
  • Ar 1 and Ar 2 are independently selected from substituted or unsubstituted groups W 1 , and the unsubstituted group W 1 is selected from the group consisting of:
  • the substituted group W 1 has one or more than two substituents, each of which is independently selected from: deuterium, cyano, fluorine, methyl, ethyl, isopropyl, tert-butyl, phenyl , naphthyl, cyclopentyl, cyclohexyl, trimethylsilyl or trifluoromethyl; when the number of substituents is greater than 1, each substituent is the same or different; optionally, two adjacent substituents form A 5- to 13-membered saturated or unsaturated ring (eg forming a cyclopentane, cyclohexane or fluorene ring).
  • substituents each of which is independently selected from: deuterium, cyano, fluorine, methyl, ethyl, isopropyl, tert-butyl, phenyl , naphthyl, cyclopentyl, cyclohexyl, trimethylsilyl or triflu
  • Ar 1 and Ar 2 are independently selected from the group consisting of the following groups:
  • Ar 1 and Ar 2 are each independently selected from a substituted or unsubstituted aryl group having 6 to 18 carbon atoms, and a substituted or unsubstituted heteroaryl group having 5 to 18 carbon atoms.
  • Ar 3 is selected from substituted or unsubstituted group W 2 , and unsubstituted group W 2 is selected from the group consisting of the following groups:
  • the substituted group W 2 has one or more substituents, each of which is independently selected from: deuterium, cyano, fluorine, methyl, ethyl, isopropyl, tert-butyl, phenyl , naphthyl, cyclopentyl or cyclohexyl; when the number of substituents is greater than 1, each substituent is the same or different.
  • Ar 3 is selected from the group that the following groups are formed:
  • the nitrogen-containing compound is selected from the group formed by:
  • the present application does not specifically limit the synthesis method of the nitrogen-containing compound provided, and those skilled in the art can determine a suitable synthesis method according to the preparation method provided in the synthesis example section of the present application for the nitrogen-containing compound.
  • the synthesis examples section of the present invention exemplarily provides a method 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 the present application according to these exemplary preparation methods, and all specific preparation methods for preparing the nitrogen-containing compounds will not be described in detail here, and those skilled in the art should not interpret it as a limit.
  • a second aspect of the present application provides an electronic component, comprising an anode, a cathode, and a functional layer 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 .
  • the nitrogen-containing compound provided in the present application can be used to form at least one organic film layer in the functional layer, so as to improve characteristics such as the lifespan of electronic components.
  • the functional layer includes a hole transport layer comprising the nitrogen-containing compound of the present application.
  • the hole transport layer may be composed of the nitrogen-containing compound provided by the present application, or may be composed of the nitrogen-containing compound provided by the present application and other materials.
  • the structure of the hole transport layer may be one layer or two or more layers.
  • the electronic element is an organic electroluminescence device or a photoelectric conversion device.
  • the electronic component is an organic electroluminescent device
  • the hole transport layer includes a first hole transport layer and a second hole transport layer (also referred to as an "electron blocking layer"), the hole transport layer
  • the first hole transport layer is closer to the anode than the second hole transport layer, wherein the second hole transport layer includes the nitrogen-containing compound, ie, the electron blocking layer includes the nitrogen-containing compound.
  • the electronic component is an organic electroluminescent device.
  • the organic electroluminescent device may include an anode 100 , a first hole transport layer 321 , a second hole transport layer 322 , an organic light emitting layer 330 serving as an energy conversion layer, and an electron transport layer 340 , which are stacked in sequence. and cathode 200.
  • 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 alloys thereof; 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 conducting polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene ](PEDT), polypyrrole and polyaniline, but not limited thereto. It is preferable to include a transparent electrode comprising indium tin oxide (ITO) as an anode.
  • ITO indium tin oxide
  • the first hole transport layer 321 may include one or more hole transport materials, and the hole transport materials may be selected from carbazole polymers, carbazole-linked triarylamine compounds or other types of compounds. There are no special restrictions on the application.
  • the first hole transport layer 321 is composed of the compound NPB.
  • 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.
  • 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 to the organic light-emitting layer 330.
  • Host material the host material transfers energy to the guest material, thereby enabling the guest material to emit light.
  • the host material of the organic light-emitting layer 330 may be metal chelate compounds, bis-styryl derivatives, aromatic amine derivatives, dibenzofuran derivatives or other types of materials, which are not specifically limited in this application.
  • the guest material of the organic light-emitting layer 330 may be a compound having a condensed aryl ring or a derivative thereof, a compound having a heteroaryl ring or a derivative thereof, an aromatic amine derivative or other materials, which are not specially made in this application. limit.
  • the electron transport layer 340 may be a single-layer structure or a multi-layer structure, which may include one or more electron transport materials, and the electron transport materials may be selected from, but not limited to, benzimidazole derivatives, oxadiazole derivatives , quinoxaline derivatives or other electron transport materials.
  • the electron transport layer 340 is composed of ET-1 (structure shown below) 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 multi-layer materials such as LiF/Al , Liq/Al, LiO 2 /Al, LiF/Ca, LiF/Al and BaF 2 /Ca.
  • a metal electrode comprising magnesium and silver is preferably included as the cathode.
  • a hole injection layer 310 may be further disposed between the anode 100 and the first hole transport layer 321 to enhance the capability of injecting holes into the first hole transport layer 321 .
  • the hole injection layer 310 can be selected from benzidine derivatives, starburst arylamine compounds, phthalocyanine derivatives or other materials, which are not specifically limited in this application.
  • the hole injection layer 310 is composed of F4-TCNQ.
  • an electron injection layer 350 may also be disposed between the cathode 200 and the electron transport layer 340 to enhance the capability of injecting electrons into the electron transport layer 340 .
  • the electron injection layer 350 may include inorganic materials such as alkali metal sulfide and alkali metal halide, or may include a complex compound of alkali metal and organic matter.
  • the electron injection layer 350 contains LiQ or Yb.
  • the organic electroluminescent device is a blue light device.
  • the electronic component is a photoelectric conversion device.
  • the photoelectric conversion device may include an anode 100 and a cathode 200 disposed opposite to each other, and a functional layer 300 disposed between the anode 100 and the cathode 200 ; the functional layer 300 includes the nitrogen-containing compound provided in the present application.
  • the functional layer 300 includes a hole transport layer 320 , and the hole transport layer 320 includes the nitrogen-containing compound of the present application.
  • the hole transport layer 320 may be composed of the nitrogen-containing compound provided in the present application, or may be composed of the nitrogen-containing compound provided by the present application and other materials.
  • the hole transport layer 320 may further include an inorganic dopant material to improve the hole transport performance of the hole transport layer 320 .
  • 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 which are stacked in sequence.
  • the photoelectric conversion device may be a solar cell, especially an organic thin film solar cell.
  • a solar cell may include an anode, a hole transport layer, a photoelectric conversion layer, an electron transport layer and a cathode that are stacked in sequence, wherein the hole transport layer includes the Nitrogenous compounds.
  • a third aspect of the present application provides an electronic device including the electronic component described in the first aspect of the present application.
  • the electronic device is a first electronic device 400
  • the first electronic device 400 includes the above-mentioned organic electroluminescence 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, such as but not limited to computer screens, mobile phone screens, televisions, electronic paper, emergency lighting, light modules, and the like.
  • 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.
  • intermediate C-X The synthesis of intermediate C-X is described below by taking intermediate C-1 as an example.
  • intermediate E-X The synthesis of intermediate E-X is described below by taking intermediate E-1 as an example.
  • intermediates E-X listed in the following table 2 are synthesized with reference to the synthesis method of intermediate E-1, wherein, intermediate C-1 is replaced by each intermediate C-X, reactant D-1 is replaced by reactant D-X, and the main raw materials used are , the corresponding synthetic intermediates E-X and their yields are shown in Table 2.
  • intermediate G-X The synthesis of intermediate G-X is described below by taking intermediate G-1 as an example.
  • intermediates G-X listed in the following table 3 are synthesized with reference to the synthesis method of intermediate G-1, wherein, intermediate E-1 is replaced by each intermediate E-X, reactant F-1 is replaced by reactant F-X, and the main raw materials used are , the corresponding synthetic intermediates G-X and their yields are shown in Table 3.
  • the substrate was cut into a size of 40mm ⁇ 40mm ⁇ 0.7mm, and a photolithography process was used to prepare it into an experimental substrate with a cathode overlapping area, an anode and an insulating layer pattern, and the surface was treated with ultraviolet ozone and O2:N2 plasma. Increase the work function of the anode (experimental substrate) and remove scum.
  • HIL hole injection layer
  • HTL1 The first hole transport layer
  • Compound 4 was vacuum evaporated on the first hole transport layer to form a thickness of The second hole transport layer (HTL2).
  • BH-1 and BD-1 were co-evaporated at a film thickness ratio of 98%: 2% to form a thickness of The blue light-emitting layer (EML).
  • ET-1 and LiQ were mixed in a weight ratio of 1:1 and evaporated to form Thick electron transport layer (ETL), then Yb was evaporated on the electron transport layer to form a thickness of the electron injection layer (EIL).
  • ETL Thick electron transport layer
  • EIL electron injection layer
  • Magnesium (Mg) and silver (Ag) were vacuum-deposited on the electron injection layer at a film thickness ratio of 1:10 to form a thickness of the cathode.
  • CP-1 was vapor-deposited on the above-mentioned cathode to form a thickness of The cover layer (CPL) of the organic electroluminescent device is completed.
  • An organic electroluminescent device was fabricated by the same method as in Example 1, except that the remaining compounds shown in Table 6 were respectively used instead of Compound 4 when forming the second hole transport layer.
  • the organic electroluminescent device was fabricated by the same method as in Example 1, except that Compound A to Compound D were respectively used instead of Compound 4 when forming the second hole transport layer.
  • the structures of compounds A to D are as follows:
  • the IVL performance of the device was tested under the condition of 20 mA/cm 2
  • the lifetime of the T95 device was also tested under the condition of 20 mA/cm 2 .
  • the results are shown in Table 6.
  • the nitrogen-containing compound of the present application when used as the material of the second hole transport layer (that is, the material of the electron blocking layer), the luminous efficiency and service life of the organic electroluminescence device can be effectively improved, and the device can be kept relatively high. low drive voltage.

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  • Chemical & Material Sciences (AREA)
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  • Physics & Mathematics (AREA)
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  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Optics & Photonics (AREA)
  • Electroluminescent Light Sources (AREA)

Abstract

La présente demande relève du domaine des matériaux organiques, et concerne un composé contenant de l'azote, un composant électronique le comprenant et un dispositif électronique. La structure du composé contenant de l'azote est représentée par la formule 1, dans laquelle L, L1 et L2 sont chacun indépendamment choisis parmi une liaison simple, un groupe arylène substitué ou non substitué ayant de 6 à 25 atomes de carbone, etc. ; Ar1, Ar2 et Ar3 sont choisis parmi un groupe aryle substitué ou non substitué ayant de 6 à 30 atomes de carbone, etc. Le composé contenant de l'azote peut améliorer les performances d'un composant électronique.
PCT/CN2022/081201 2021-03-31 2022-03-16 Composé contenant de l'azote, composant électronique le comprenant et dispositif électronique WO2022206389A1 (fr)

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