WO2023202198A1 - Matériau organique, élément électronique et appareil électronique - Google Patents

Matériau organique, élément électronique et appareil électronique Download PDF

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WO2023202198A1
WO2023202198A1 PCT/CN2023/076636 CN2023076636W WO2023202198A1 WO 2023202198 A1 WO2023202198 A1 WO 2023202198A1 CN 2023076636 W CN2023076636 W CN 2023076636W WO 2023202198 A1 WO2023202198 A1 WO 2023202198A1
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substituted
carbon atoms
unsubstituted
organic material
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马天天
呼琳琳
张鹤鸣
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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
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C211/00—Compounds containing amino groups bound to a carbon skeleton
    • C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
    • C07C211/44—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to only one six-membered aromatic ring
    • C07C211/49—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to only one six-membered aromatic ring having at least two amino groups bound to the carbon skeleton
    • C07C211/50—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to only one six-membered aromatic ring having at least two amino groups bound to the carbon skeleton with at least two amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
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    • C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
    • C07C211/57—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton
    • C07C211/61—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton with at least one of the condensed ring systems formed by three or more rings
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    • C07D—HETEROCYCLIC COMPOUNDS
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    • C07D209/56—Ring systems containing three or more rings
    • C07D209/80—[b, c]- or [b, d]-condensed
    • C07D209/82—Carbazoles; Hydrogenated carbazoles
    • C07D209/86—Carbazoles; Hydrogenated carbazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system
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    • 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
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    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D307/91—Dibenzofurans; Hydrogenated dibenzofurans
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    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
    • C07D333/76—Dibenzothiophenes
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    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
    • C07F7/02—Silicon compounds
    • C07F7/08—Compounds having one or more C—Si linkages
    • C07F7/0803—Compounds with Si-C or Si-Si linkages
    • C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
    • C07F7/0812—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring
    • C—CHEMISTRY; METALLURGY
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    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/06—Systems containing only non-condensed rings with a five-membered ring
    • C07C2601/08—Systems containing only non-condensed rings with a five-membered ring the ring being saturated
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/14—The ring being saturated
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/18—Systems containing only non-condensed rings with a ring being at least seven-membered
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    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2603/00—Systems containing at least three condensed rings
    • C07C2603/02—Ortho- or ortho- and peri-condensed systems
    • C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
    • C07C2603/06—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members
    • C07C2603/10—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings
    • C07C2603/12—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings only one five-membered ring
    • C07C2603/18—Fluorenes; Hydrogenated fluorenes
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    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2603/00—Systems containing at least three condensed rings
    • C07C2603/02—Ortho- or ortho- and peri-condensed systems
    • C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
    • C07C2603/22—Ortho- or ortho- and peri-condensed systems containing three rings containing only six-membered rings
    • C07C2603/26—Phenanthrenes; Hydrogenated phenanthrenes
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    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2603/00—Systems containing at least three condensed rings
    • C07C2603/93—Spiro compounds
    • C07C2603/94—Spiro compounds containing "free" spiro atoms
    • 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 belongs to the technical field of organic materials, and in particular relates to an organic material and electronic components and electronic devices containing the same.
  • organic electroluminescent devices also called organic light-emitting diodes
  • This type of electronic component usually includes a cathode and an anode arranged oppositely, and a functional layer arranged between the cathode and anode.
  • the functional layer is composed of multiple organic or inorganic film layers, and generally includes an energy conversion layer, a hole transport layer located between the energy conversion layer and the anode, and an electron transport layer located between the energy conversion layer and the cathode.
  • an organic electroluminescent device as an example, it generally includes an anode, a hole transport layer, an electroluminescent layer as an energy conversion layer, an electron transport layer and a cathode that are stacked in sequence.
  • anode When a voltage is applied to the cathode and anode, the two electrodes generate an electric field. Under the action of the electric field, the electrons on the cathode side move toward the electroluminescent layer, and the holes on the anode side also move toward the luminescent layer. The electrons and holes combine in the electroluminescent layer. Excitons are formed, and the excitons release energy outwards in the excited state, thereby causing the electroluminescent layer to emit light.
  • Organic charge transport materials are a type of organic semiconductor material that can achieve directional and orderly controllable migration of carriers under the action of an electric field to transport charges when carriers (electrons or holes) are injected.
  • This type of material requires excellent electron donating properties, low ionization potential, high hole mobility, good solubility and amorphous film-forming properties, strong fluorescence properties and photostability.
  • the excellent performance of triarylamine materials among hole transport layer materials is one of the hot spots of research.
  • existing triarylamine hole transport layer materials do not perform well in terms of voltage, luminous efficiency, power and lifetime in the device. . Therefore, it is still necessary to continue to develop new materials to further improve the performance of electronic components.
  • the purpose of this application is to provide an organic material and an electronic component and electronic device containing the same.
  • the organic material can improve the performance of the electronic component and electronic device, such as reducing the driving voltage of the device. Improve device efficiency and lifespan.
  • a first aspect of the present application provides an organic material having a structure represented by Formula 1:
  • n is selected from 1, 2 or 3. When n is greater than or equal to 2, any two R 1s are the same or different, and any two R 2s are the same or different;
  • L is selected from a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms;
  • L 1 , L 2 and L 3 are each independently selected from a single bond, a substituted or unsubstituted arylene group with 6 to 30 carbon atoms, and a substituted or unsubstituted heteroarylene group with 3 to 30 carbon atoms. ;
  • Ar 1 and Ar 2 are independently selected from substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted di Benzofuranyl, substituted or unsubstituted dibenzothienyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted 9,9'-spirobifluorenyl;
  • Ar 3 is selected from substituted or unsubstituted aryl groups with 6-30 carbon atoms;
  • the substituents in L, L 1 , L 2 , L 3 , Ar 1 and Ar 2 are the same or different, and are independently selected from deuterium, halogen group, cyano group, alkyl group with 1-10 carbon atoms, carbon Cycloalkyl group with 3-10 carbon atoms, aryl group with 6-20 carbon atoms, heteroaryl group with 5-20 carbon atoms, deuterated aryl group with 6-20 carbon atoms, carbon number A haloaryl group with 6-20 carbon atoms and a triarylsilyl group with 18-24 carbon atoms;
  • the substituents in Ar 3 are the same or different, and are independently selected from deuterium, halogen, cyano group, alkyl group with 1 to 10 carbon atoms, deuterated alkyl group with 1 to 10 carbon atoms, and Cycloalkyl group with 3-10 carbon atoms, aryl group with 6-20 carbon atoms, deuterated aryl group with 6-20 carbon atoms, halogenated aryl group with 6-20 carbon atoms, 18 carbon atoms -24 triarylsilyl;
  • any two adjacent substituents form a ring.
  • a second aspect of the present application provides an electronic component, including an anode and a cathode arranged oppositely, and a functional layer disposed between the anode and the cathode; the functional layer includes the above-mentioned organic material.
  • a third aspect of the present application provides an electronic device, including the electronic component described in the second aspect.
  • the structure of the compound of the present application contains a triarylamine group and an aryl group, both of which are combined through the same methylene group on the cycloalkyl group, and the aromatic group in the triarylamine group is selected from several specific groups. These specific groups create a steric conjugation effect between the groups of the compound molecules. Through the spatial conjugation effect, the molecule has a suitable HOMO energy level and higher hole mobility, which is suitable for use in the hole auxiliary layer of organic electroluminescent devices; at the same time, the molecular structure has good amorphous stacking properties. It can reduce the crystallinity of the material and extend the device life; in particular, when the aromatic group in the triarylamine selects a specific group, the electron tolerance of the material can be effectively improved, thereby further improving the life of the organic electroluminescent device.
  • Figure 1 is a schematic structural diagram of an organic electroluminescent device of the present application.
  • FIG. 2 is a schematic structural diagram of an electronic device according to the present application.
  • Example embodiments will now be described more fully with reference to the accompanying drawings.
  • Example embodiments may, however, be embodied in various forms and should not be construed as limited to the examples set forth herein; rather, these embodiments are provided so that this disclosure will be thorough and complete and will fully convey the concepts of the example embodiments. be communicated to those skilled in the art.
  • the described features, structures or characteristics may be combined in any suitable manner in one or more embodiments. In the following description, numerous specific details are provided to provide a thorough understanding of embodiments of the present application.
  • the present application provides an organic material having a structure shown in Formula 1:
  • n is selected from 1, 2 or 3. When n is greater than or equal to 2, any two R 1s are the same or different, and any two R 2s are the same or different;
  • L is selected from a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms;
  • L 1 , L 2 and L 3 are each independently selected from a single bond, a substituted or unsubstituted arylene group with 6 to 30 carbon atoms, and a substituted or unsubstituted heteroarylene group with 3 to 30 carbon atoms. ;
  • Ar 1 and Ar 2 are independently selected from substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted di Benzofuranyl, substituted or unsubstituted dibenzothienyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted 9,9'-spirobifluorenyl;
  • Ar 3 is selected from substituted or unsubstituted aryl groups with 6-30 carbon atoms;
  • the substituents in L, L 1 , L 2 , L 3 , Ar 1 and Ar 2 are the same or different, and are independently selected from deuterium, halogen group, cyano group, alkyl group with 1-10 carbon atoms, carbon Cycloalkyl group with 3-10 carbon atoms, aryl group with 6-20 carbon atoms, heteroaryl group with 5-20 carbon atoms, deuterated aryl group with 6-20 carbon atoms, carbon number A haloaryl group with 6-20 carbon atoms and a triarylsilyl group with 18-24 carbon atoms;
  • the substituents in Ar 3 are the same or different, and are independently selected from deuterium, halogen, cyano group, alkyl group with 1 to 10 carbon atoms, deuterated alkyl group with 1 to 10 carbon atoms, and Cycloalkyl group with 3-10 carbon atoms, aryl group with 6-20 carbon atoms, deuterated aryl group with 6-20 carbon atoms, halogenated aryl group with 6-20 carbon atoms, 18 carbon atoms -24 triarylsilyl;
  • any two adjacent substituents form a ring.
  • the terms “optionally” and “optionally” mean that the subsequently described event or circumstance may occur but need not occur, and the description includes occasions where the event or circumstance does or does not occur.
  • “optionally, two adjacent substituents form a ring;” means that the two substituents can form a ring but do not have to form a ring, including: the situation where two adjacent substituents form a ring and the two phases. The adjacent substituents do not form a ring.
  • any two adjacent substituents form a ring can include two substituents on the same atom, and can also include two adjacent atoms each having one substituent. group; where, when there are two substituents on the same atom, the two substituents can form a saturated or unsaturated ring with the atom they are jointly connected to; when two adjacent atoms have one substituent each, These two substituents can be fused to form a ring. For example, when Ar 1 has 2 or two or more substituents.
  • a saturated or unsaturated cyclic group is formed, such as: benzene ring, naphthalene ring, phenanthrene ring, anthracene ring, fluorene ring, ring Pentane, cyclohexane, adamantane, etc.
  • the fluorenyl group can be substituted by 1 or 2 substituents, wherein, in the case where the above fluorenyl group is substituted, it can be: etc., but are not limited to this.
  • each...independently is and “...respectively and independently are” and “...are each independently selected from” are interchangeable, and should be understood in a broad sense. They can either be It means that in different groups, the specific options expressed by the same symbols do not affect each other. It can also mean that in the same group, the specific options expressed by the same symbols do not affect each other.
  • each q is independently 0, 1, 2 or 3
  • each R is independently selected from hydrogen, deuterium, fluorine, and chlorine.
  • Formula Q-1 represents that there are q substituents R" on the benzene ring.
  • each R can be the same or different, and the options of each R” do not affect each other;
  • Formula Q-2 indicates that there are q substituents R” on each benzene ring of biphenyl, and the R on the two benzene rings "The number of substituents q can be the same or different, each R" can be the same or different, and the options for each R" do not affect each other.
  • non-located connecting bonds refer to single bonds protruding from the ring system" ”, which means that one end of the bond can be connected to any position in the ring system that the bond penetrates, and the other end is connected to the rest of the compound molecule.
  • the naphthyl group represented by the formula (f) is connected to other positions of the molecule through two non-positioned bonds that penetrate the bicyclic ring, and its meaning includes such as the formula (f) -1)-Any possible connection method shown in formula (f-10).
  • the dibenzofuryl group represented by the formula (X') is connected to other positions of the molecule through an unpositioned bond extending from the middle of one side of the benzene ring, Its meaning includes any possible connection method shown in formula (X'-1) to formula (X'-4).
  • substituted or unsubstituted means that the functional group described after the term may or may not have a substituent (hereinafter, for convenience of description, the substituents are collectively referred to as Rc).
  • substituted or unsubstituted aryl refers to an aryl group having a substituent Rc or an unsubstituted aryl group.
  • the above-mentioned substituent Rc may be, for example, deuterium, halogen group, cyano group, alkyl group, cycloalkyl group, aryl group, heteroaryl group, deuterated aryl group, haloaryl group, triarylsilyl group, etc.
  • the number of carbon atoms of a substituted or unsubstituted functional group refers to the number of all carbon atoms. For example, if L 1 is a substituted arylene group having 12 carbon atoms, then all of the carbon atoms in the arylene group and the substituents thereon are 12.
  • aryl refers to an optional functional group or substituent derived from an aromatic carbocyclic ring.
  • the aryl group may be a monocyclic aryl group (e.g. phenyl) or polycyclic aryl, in other words, the aryl group can be a single-ring aryl group, a fused-ring aryl group, two or more single-ring aryl groups conjugated through a carbon-carbon bond, a conjugated through a carbon-carbon bond Connected single-ring aryl groups 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.
  • aryl groups may include, but are not limited to, phenyl, naphthyl, fluorenyl, anthracenyl, phenanthrenyl, biphenyl, terphenyl, benzo[9,10]phenanthrenyl, pyrenyl, benzofluoranthene base, base, spirobifluorenyl base, etc.
  • the arylene group refers to a bivalent group formed by the aryl group further losing one hydrogen atom.
  • terphenyl includes
  • the substituted aryl group may be one or more hydrogen atoms in the aryl group substituted by groups such as deuterium atoms, halogen groups, cyano groups, aryl groups, heteroaryl groups, alkyl groups, cycloalkyl groups, etc. .
  • 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 7 heteroatoms in the ring.
  • the heteroatoms can be B, O, N, P, Si At least one of , Se and S.
  • a heteroaryl group can be a monocyclic heteroaryl group or a polycyclic heteroaryl group.
  • a heteroaryl group can be a single aromatic ring system or multiple aromatic ring systems conjugated through carbon-carbon bonds, and any aromatic
  • the ring system is an aromatic single ring or an aromatic fused ring.
  • heteroaryl groups may include thienyl, furyl, pyrrolyl, imidazolyl, thiazolyl, oxazolyl, oxadiazolyl, triazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, Acridinyl, pyridazinyl, pyrazinyl, quinolinyl, quinazolinyl, quinoxalinyl, phenoxazinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyridyl Azinyl, isoquinolinyl, indolyl, carbazolyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothienyl, dibenzothienyl, thiophene Thiophenyl
  • a substituted heteroaryl group may be one or more hydrogen atoms in the heteroaryl group substituted by a group such as a deuterium atom, a halogen group, a cyano group, an aryl group, a heteroaryl group, an alkyl group, a cycloalkyl group, etc. group replaced.
  • a group such as a deuterium atom, a halogen group, a cyano group, an aryl group, a heteroaryl group, an alkyl group, a cycloalkyl group, etc. group replaced.
  • the number of carbon atoms of a substituted heteroaryl group refers to the total number of carbon atoms of the heteroaryl group and the substituents on the heteroaryl group.
  • the number of carbon atoms of the substituted or unsubstituted aryl group may be 6-30, for example, the number of carbon atoms may be 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17 , 18, 19, 20, 21, 22, 23, 24, 25 or 30.
  • aryl groups as substituents include, but are not limited to, phenyl, biphenyl, naphthyl, fluorenyl, phenanthrenyl, anthracenyl, base.
  • the number of carbon atoms of the substituted or unsubstituted heteroaryl group may be 3-30, for example, the number of carbon atoms may be 3, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20 or 30.
  • heteroaryl groups as substituents include, but are not limited to, triazinyl, pyridyl, pyrimidinyl, carbazolyl, dibenzofuranyl, dibenzothienyl, quinolyl, Quinazolinyl, quinoxalinyl, isoquinolinyl, carbazolyl, N-phenylcarbazolyl.
  • the alkyl group having 1 to 10 carbon atoms may include a linear alkyl group having 1 to 10 carbon atoms and a branched alkyl group having 3 to 10 carbon atoms.
  • the number of carbon atoms of the alkyl group may be, for example, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10.
  • groups include, but are not limited to, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl, neopentyl, n-hexyl, n-octyl, 2-ethylhexyl, nonyl, decyl, 3,7-dimethyloctyl, etc.
  • the halogen group can be, for example, fluorine, chlorine, bromine, or iodine.
  • the number of carbon atoms of the cycloalkyl group having 3 to 10 carbon atoms may be, for example, 3, 4, 5, 6, 7, 8 or 10.
  • Specific examples of cycloalkyl include, but are not limited to, cyclopentyl and cyclohexyl.
  • triarylsilyl groups with carbon atoms of 18-24 include, but are not limited to, triphenylsilyl groups and the like.
  • deuterated alkyl groups having 1 to 10 carbon atoms include, but are not limited to, trideuterated methyl.
  • deuterated aryl groups with 6 to 20 carbon atoms include, but are not limited to, monodeuterated phenyl, dideuterated phenyl, trideuterated phenyl, tetradeuterated phenyl, and pentadeuterated phenyl. Substituted phenyl.
  • halogenated aryl groups with 6 to 20 carbon atoms include, but are not limited to, monofluorophenyl, difluorophenyl, trifluorophenyl, tetrafluorophenyl, pentafluorophenyl, etc. Substituted phenyl.
  • the organic material has the structure shown in Formula 1-1 or Formula 1-2:
  • each R 1 and each R 2 are hydrogen.
  • n is selected from 1 or 2.
  • L is selected from a substituted or unsubstituted arylene group with 6-15 carbon atoms, and a substituted or unsubstituted heteroarylene group with 12-20 carbon atoms.
  • the substituents in L are the same or different, and are independently selected from deuterium, halogen group, cyano group, alkyl group with 1 to 5 carbon atoms, phenyl, naphthyl or biphenyl group.
  • L is selected from substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted biphenylene, substituted or unsubstituted anthracene, substituted Or unsubstituted phenanthrene group, substituted or unsubstituted fluorenylene group, substituted or unsubstituted carbazolylene group, substituted or unsubstituted dibenzofurylene group, substituted or unsubstituted dibenzothienylene group .
  • the substituents in L are the same or different, and are independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, naphthyl, biphenyl or phenyl.
  • L is selected from a substituted or unsubstituted group W, wherein the unsubstituted group W is selected from the group consisting of:
  • the substituted group W has one or more substituents, and the substituents are independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, phenyl, and naphthyl. or biphenyl, and when the number of substituents is greater than 1, each substituted The basis is the same or different.
  • L is selected from the group consisting of:
  • L 1 , L 2 and L 3 are the same or different, and are independently selected from single bonds or phenylene groups.
  • L 1 , L 2 and L 3 are the same or different, and are independently selected from the group consisting of single bonds or the following groups:
  • the substituents in Ar 1 and Ar 2 are the same or different, and are independently selected from deuterium, halogen groups, cyano groups, alkyl groups with 1 to 5 carbon atoms, and Deuterated alkyl group with 1-5 carbon atoms, aryl group with 6-12 carbon atoms, deuterated aryl group with 6-12 carbon atoms, haloaryl group or triphenyl group with 6-12 carbon atoms Silicon based;
  • any two adjacent substituents form a saturated or unsaturated ring with 5-13 carbon atoms.
  • any two adjacent substituents can form cyclohexane cyclopentane benzene ring naphthalene ring or fluorene ring
  • the substituents in Ar 1 and Ar 2 are the same or different, and are independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, phenyl , naphthyl, biphenyl, trideuterated methyl, pentadeuterated phenyl, monofluorophenyl or triphenylsilyl.
  • Ar 1 and Ar 2 are the same or different, and are independently selected from substituted or unsubstituted group V, wherein unsubstituted group V is selected from the group of the following groups:
  • the substituted group V has one or more substituents, and the substituents in the substituted group V are independently selected from deuterium, fluorine, cyano, phenyl, methyl, ethyl, n-propyl , isopropyl, tert-butyl, phenyl, naphthyl, biphenyl, trideuterated methyl, pentadeuterated phenyl, monofluorophenyl or triphenylsilyl group, and when the base When the number of substituents on group V is greater than 1, each substituent may be the same or different.
  • Ar 1 and Ar 2 are the same or different, and are independently selected from the group consisting of the following groups:
  • Ar 3 is selected from substituted or unsubstituted aryl groups with carbon atoms of 6-25.
  • the substituents in Ar 3 are the same and different, and are independently selected from deuterium, halogen group, cyano group, alkyl group with 1-5 carbon atoms, and deuterated alkyl group with 1-5 carbon atoms. or phenyl;
  • any two adjacent substituents form a saturated or unsaturated ring with 5-13 carbon atoms.
  • any two adjacent substituents can form cyclohexane cyclopentane benzene ring naphthalene ring or fluorene ring
  • Ar 3 is selected from substituted or unsubstituted aryl groups having 6 to 20 carbon atoms.
  • Ar 3 is selected from substituted or unsubstituted aryl groups having 6 to 15 carbon atoms.
  • Ar 3 is selected from substituted or unsubstituted aryl groups having 6 to 12 carbon atoms.
  • Ar 3 is selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted fluorenyl, substituted or unsubstituted 9,9'-spirobifluorenyl.
  • the substituents in Ar 3 are the same and different, and are independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, trideuterated methyl or benzene base.
  • Ar 3 is selected from a substituted or unsubstituted group G, wherein the unsubstituted group G is selected from the following group:
  • the substituted group G has one or more substituents, and the substituents in the substituted group G are independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, A group consisting of tert-butyl, trideuterated methyl or phenyl, and when the number of substituents on group G is greater than 1, each substituent may be the same or different.
  • Ar 3 is selected from the group consisting of:
  • the organic material is selected from the group consisting of the following compounds:
  • the present application provides an electronic component, including an anode and a cathode arranged oppositely, and a functional layer disposed between the anode and the cathode; the functional layer contains the organic compound of the present application.
  • the electronic component is an organic electroluminescent device.
  • the electronic component is an organic electroluminescent device.
  • the organic electroluminescent device may include an anode 100 , a hole transport layer 320 , a hole auxiliary layer 330 , an organic light emitting layer 340 , an electron transport layer 350 and a cathode 200 that are stacked in sequence.
  • the organic electroluminescent device is a red organic electroluminescent device.
  • the anode 100 includes an anode material, which is optionally a material with a large work function that facilitates injection of holes into the functional layer.
  • anode materials include: metals such as nickel, platinum, vanadium, chromium, copper, zinc and gold or their alloys; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO) and indium zinc oxide (IZO); Combined metals and oxides such as ZnO:Al or SnO2 :Sb ; or conductive polymers such as 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 preferred.
  • the hole transport layer 320 includes one or more hole transport materials.
  • the hole transport materials may be selected from carbazole polymers, carbazole-linked triarylamine compounds, or other types of compounds. Those skilled in the art The selection can be made with reference to the existing technology, and this application does not impose special limitations on this. In some embodiments of the present application, the hole transport layer 320 is HT-15.
  • the hole auxiliary layer 330 is an organic material of the present application.
  • a hole injection layer 310 may also be provided between the anode 100 and the hole transport layer 320 to enhance the ability to inject holes into the hole transport layer 320.
  • the hole injection layer 310 can be made of benzidine derivatives, starburst arylamine compounds, phthalocyanine derivatives or other materials, which are not particularly limited in this application.
  • the material of the hole injection layer 310 may, for example, be selected from the following compounds or any combination thereof;
  • the hole injection layer 310 is composed of HAT-CN.
  • the organic light-emitting layer 340 may be composed of a single light-emitting layer material, or may include a host material and a doping material.
  • the organic light-emitting layer 340 is composed of a host material and a doping material. The holes injected into the organic light-emitting layer 340 and the electrons injected into the organic light-emitting layer 340 can recombine in the organic light-emitting layer 340 to form excitons, and the excitons transfer energy. To the host material, the host material transfers energy to the doping material, thereby enabling the doping material to emit light.
  • the main material of the organic light-emitting layer 340 may be metal chelate compounds, bistyryl derivatives, aromatic amine derivatives, dibenzofuran derivatives or other types of materials, which are not specifically limited in this application.
  • the host material of the organic light-emitting layer 340 is RH-01.
  • the guest material of the organic light-emitting layer 340 may be a compound with a condensed aryl ring or its derivatives, a compound with a heteroaryl ring or its derivatives, an aromatic amine derivative or other materials, which is not specified in this application. limit. Guest materials are also called doping materials or dopants. Specific examples of red phosphorescent dopants for red organic electroluminescent devices include, but are not limited to,
  • the host material of the organic light-emitting layer 340 is RH-01, and the guest material is Ir(piq) 2 (acac).
  • the electron transport layer 350 may have a single-layer structure or a multi-layer structure, and may include one or more electron transport materials.
  • the electron transport materials may be selected from, but are not limited to, ET-01, LiQ, and benzimidazole derivatives. , oxadiazole derivatives, quinoxaline derivatives or other electron transport materials, there are no special limitations for comparison in this application.
  • the materials of the electron transport layer 350 include but are not limited to the following compounds:
  • the electron transport layer 350 is composed of ET-01 and LiQ.
  • the cathode 200 may include a cathode material, which is a material with a small work function that facilitates electron injection into the functional layer.
  • cathode materials include, but are not limited to, metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead or alloys thereof; or multilayer materials such as LiF/Al , Liq/Al, LiO 2 /Al, LiF/Ca, LiF/Al and BaF 2 /Ca.
  • a metal electrode containing magnesium and silver is included as the cathode.
  • an electron injection layer may also be provided between the cathode 200 and the electron transport layer 350 360, the electron injection layer 360 may include ytterbium (Yb).
  • Yb ytterbium
  • a third aspect of this application provides an electronic device, including the electronic component described in the second aspect of this application.
  • the electronic device provided is an electronic device 400 , which includes the above-mentioned organic electroluminescent device.
  • the electronic device 400 may be, for example, a display device, a lighting device, an optical communication device, or other types of electronic devices.
  • it may include but is not limited to a computer screen, a mobile phone screen, a television, electronic paper, emergency lighting, an optical module, etc.
  • the compounds of the synthesis methods not mentioned in this application are all raw material products obtained through commercial channels.
  • Example 1 Red organic electroluminescent device
  • the anode is prepared by the following process: ITO/Ag/ITO with a thickness of The glass substrate (manufactured by Corning) was cut into a size of 40 mm ⁇ 40 mm ⁇ 0.7 mm, and the photolithography process was used to prepare it into an experimental substrate with cathode, anode and insulating layer patterns, using ultraviolet ozone and O 2 : N 2 plasma. Surface treatment to increase the work function of the anode (experimental substrate) and remove scum.
  • HIL hole injection layer
  • HTL hole transport layer
  • Compound 1 was vacuum evaporated on the hole transport layer to form hole auxiliary layer.
  • RH-01 and Ir(piq) 2 were co-evaporated with a film thickness ratio of 94%:6% to form organic light-emitting layer (R-EML).
  • ETL Electron transport layer
  • Yb is evaporated on the electron transport layer to form a thickness of
  • the electron injection layer (EIL) is then mixed with magnesium (Mg) and silver (Ag) at an evaporation rate of 1:9, and vacuum evaporated on the electron injection layer to form a thickness of the cathode.
  • the evaporation thickness on the cathode is of HT-16 to form an organic covering layer (CPL), thereby completing the manufacture of organic light-emitting devices.
  • An organic electroluminescent device was produced using the same method as in Example 1, except that the compound shown in Table 6 below was used instead of Compound 1 when forming the hole auxiliary layer.
  • Organic electroluminescence was produced using the same method as in Example 1, except that Compound A, Compound B, Compound C, Compound D, Compound E and Compound F in Table 6 were used instead of Compound 1 when forming the hole auxiliary layer. device.
  • Examples 1-35 and Comparative Examples 1-6 were tested for IVL (current, voltage, brightness, etc.) under a current density of 10mA/ cm2 , and their T95 lifespan was tested under a current density of 20mA/ cm2 .
  • IVL current, voltage, brightness, etc.
  • T95 lifespan was tested under a current density of 20mA/ cm2 .
  • Table 6 The test results are shown in Table 6 below.
  • the performance of the organic electroluminescent device of Example 1-35 is improved.
  • the driving voltage of the organic electroluminescent devices of Examples 1-35 is close to that of the comparative example, the current efficiency is increased by at least 15.5%, and the lifetime is increased by at least 10.2%. Therefore, using the organic material of the present application as a hole auxiliary layer of an organic electroluminescent device can improve efficiency and effectiveness while maintaining a low operating voltage.
  • Examples 1-35 of the present application have an increase rate of current efficiency of at least 26% and an increase of lifespan of at least 10.2%.
  • the reason may be that the aryl part of the triarylamine group in Compound A and Compound F uses a specific binaphthyl group, and the binaphthyl group is connected to the amine group, which reduces the T1 energy level of the compound, resulting in organic electroluminescence. The efficiency of the device decreases.
  • Examples 1-35 of the present application have the current efficiency increased by at least 15.5% and the service life increased by at least 20.4%.
  • the reason may be that the aryl part of the triarylamine group of Compound B, Compound C and Compound D is phenyl or benzyl.
  • the conjugation range of phenyl or benzyl is small, resulting in insufficient molecular stability of the compounds. , resulting in reduced lifetime of organic electroluminescent devices.
  • the core structure of this application is a combination of a triarylamine group and an aryl group through 1,1-substitution of a cycloalkyl group, and the aromatic group in the triarylamine group is selected from several specific group. These specific groups create a steric conjugation effect between the groups of the compound molecules. Through the spatial conjugation effect, the molecule has a suitable HOMO energy level and higher hole mobility, which is suitable for use in the hole auxiliary layer of organic electroluminescent devices; at the same time, the molecular structure has good amorphous stacking properties.
  • the material can reduce the crystallinity of the material and extend the device life; in particular, when the aromatic group in the triarylamine selects a specific group, the electron tolerance of the material can be effectively improved, thereby further improving the life of the organic electroluminescent device. Especially when the cycloalkyl group is cyclopentane, the device performance is better.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Electroluminescent Light Sources (AREA)

Abstract

La présente invention concerne un matériau organique, un élément électronique et un appareil électronique. Le matériau organique fourni par la présente invention a une structure telle que représentée dans la formule 1. Le matériau organique est appliqué à un dispositif électroluminescent organique, de telle sorte que les performances du dispositif peuvent être remarquablement améliorées.
PCT/CN2023/076636 2022-04-19 2023-02-16 Matériau organique, élément électronique et appareil électronique WO2023202198A1 (fr)

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CN115521212A (zh) * 2022-04-19 2022-12-27 陕西莱特光电材料股份有限公司 有机材料、电子元件和电子装置

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CN109456256A (zh) * 2018-12-28 2019-03-12 武汉天马微电子有限公司 化合物、显示面板以及显示装置
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