WO2023229228A1 - Composé hétérocyclique et dispositif électroluminescent organique le comprenant - Google Patents

Composé hétérocyclique et dispositif électroluminescent organique le comprenant Download PDF

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WO2023229228A1
WO2023229228A1 PCT/KR2023/005090 KR2023005090W WO2023229228A1 WO 2023229228 A1 WO2023229228 A1 WO 2023229228A1 KR 2023005090 W KR2023005090 W KR 2023005090W WO 2023229228 A1 WO2023229228 A1 WO 2023229228A1
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이남진
정원장
김동준
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엘티소재주식회사
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    • C—CHEMISTRY; METALLURGY
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    • 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
    • C07D307/93—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 condensed with a ring other than six-membered
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    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
    • C07D407/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings
    • C07D407/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
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    • 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
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
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    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
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    • 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
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    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
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    • H10K50/14—Carrier transporting layers
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    • 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
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    • 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
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Definitions

  • the present invention relates to heterocyclic compounds and organic light-emitting devices containing the same.
  • Organic light emitting devices are a type of self-emitting display devices and have the advantages of a wide viewing angle, excellent contrast, and fast response speed.
  • Organic light-emitting devices have a structure in which an organic thin film is placed between two electrodes. When voltage is applied to an organic light emitting device with this structure, electrons and holes injected from two electrodes combine in the organic thin film to form a pair and then disappear, emitting light.
  • the organic thin film may be composed of a single layer or multiple layers, depending on need.
  • the material of the organic thin film may have a light-emitting function as needed.
  • a compound that can independently form a light-emitting layer may be used, or a compound that can act as a host or dopant of a host-dopant-based light-emitting layer may be used.
  • compounds that can perform roles such as hole injection, hole transport, electron blocking, hole blocking, electron transport, and electron injection may be used.
  • Patent Document 1 U.S. Patent No. 4,356,429
  • the present invention seeks to provide a heterocyclic compound and an organic light-emitting device containing the same.
  • the present invention provides a heterocyclic compound represented by the following formula (1):
  • At least one of R2 to R12 is a group represented by the following formula (2),
  • R13 and R14 are -CRaRbRc, and Ra to Rc are the same or different from each other and are each independently hydrogen; heavy hydrogen; halogen; Cyano group; Substituted or unsubstituted C1 to C60 alkyl group; Substituted or unsubstituted C2 to C60 alkenyl group; Substituted or unsubstituted C2 to C60 alkynyl group; Substituted or unsubstituted C1 to C60 alkoxy group; Substituted or unsubstituted C3 to C60 cycloalkyl group; And a substituted or unsubstituted C2 to C60 heterocycloalkyl group; selected from the group consisting of,
  • L1 and L2 are the same or different from each other and are each independently a single bond; Substituted or unsubstituted C6 to C60 arylene group; Or a substituted or unsubstituted C2 to C60 heteroarylene group;
  • Ar1 and Ar2 are the same or different from each other, and are each independently a substituted or unsubstituted aryl group of C6 to C60; Or a substituted or unsubstituted C2 to C60 heteroaryl group;
  • n are the same as or different from each other and are each independently an integer from 0 to 3,
  • the present invention includes a first electrode; a second electrode provided opposite the first electrode; and at least one organic material layer provided between the first electrode and the second electrode, wherein at least one layer of the organic material layer contains a heterocyclic compound according to the present invention.
  • the heterocyclic compound according to one embodiment can be used as an organic layer material of an organic light-emitting device.
  • the heterocyclic compound may serve as a hole injection layer material, an electron blocking layer material, a hole transport layer material, a light emitting layer material, an electron transport layer material, a hole blocking layer material, an electron blocking layer material, an electron injection layer material, etc. in an organic light emitting device. You can.
  • the heterocyclic compound can be used as a hole transport layer material, a hole transport auxiliary layer material, or an electron blocking layer material of an organic light emitting device.
  • the driving voltage of the organic light-emitting device can be lowered, luminous efficiency can be improved, and lifespan characteristics can be improved.
  • 1 to 3 are diagrams schematically showing the stacked structure of an organic light-emitting device according to an embodiment of the present invention.
  • substitution means changing a hydrogen atom bonded to a carbon atom of a compound to another substituent, and the position to be substituted is not limited as long as it is the position where the hydrogen atom is substituted, that is, a position where the substituent can be substituted. , when two or more substituents are substituted, the two or more substituents may be the same or different from each other.
  • the halogen may be fluorine, chlorine, bromine, or iodine.
  • the alkyl group includes a straight chain or branched chain having 1 to 60 carbon atoms, and may be further substituted by another substituent.
  • the carbon number of the alkyl group may be 1 to 60, specifically 1 to 40, and more specifically 1 to 20.
  • Specific examples include methyl group, ethyl group, propyl group, n-propyl group, isopropyl group, butyl group, n-butyl group, isobutyl group, tert-butyl group, sec-butyl group, 1-methyl-butyl group, 1- Ethyl-butyl group, pentyl group, n-pentyl group, isopentyl group, neopentyl group, tert-pentyl group, hexyl group, n-hexyl group, 1-methylpentyl group, 2-methylpentyl group, 4-methyl- 2-pentyl group, 3,3-dimethylbutyl group, 2-ethylbutyl group, heptyl group, n-heptyl group, 1-methylhexyl group, cyclopentylmethyl group, cyclohexylmethyl group, octyl group, n-octyl group,
  • the alkenyl group includes a straight chain or branched chain having 2 to 60 carbon atoms, and may be further substituted by another substituent.
  • the alkenyl group may have 2 to 60 carbon atoms, specifically 2 to 40 carbon atoms, and more specifically 2 to 20 carbon atoms.
  • Specific examples include vinyl group, 1-propenyl group, isopropenyl group, 1-butenyl group, 2-butenyl group, 3-butenyl group, 1-pentenyl group, 2-pentenyl group, 3-pentenyl group, 3-methyl-1 -Butenyl group, 1,3-butadienyl group, allyl group, 1-phenylvinyl-1-yl group, 2-phenylvinyl-1-yl group, 2,2-diphenylvinyl-1-yl group, 2-phenyl-2 -(naphthyl-1-yl)vinyl-1-yl group, 2,2-bis(diphenyl-1-yl)vinyl-1-yl group, stilbenyl group, styrenyl group, etc., but is not limited thereto. .
  • the alkynyl group includes a straight chain or branched chain having 2 to 60 carbon atoms, and may be further substituted by another substituent.
  • the carbon number of the alkynyl group may be 2 to 60, specifically 2 to 40, and more specifically, 2 to 20.
  • the alkoxy group may be straight chain, branched chain, or ring chain.
  • the number of carbon atoms of the alkoxy group is not particularly limited, but is preferably 1 to 20 carbon atoms.
  • the cycloalkyl group includes a monocyclic or polycyclic ring having 3 to 60 carbon atoms and may be further substituted by another substituent.
  • polycyclic refers to a group in which a cycloalkyl group is directly connected to or condensed with another ring group.
  • the other ring group may be a cycloalkyl group, but may also be another type of ring group, such as a heterocycloalkyl group, an aryl group, or a heteroaryl group.
  • the carbon number of the cycloalkyl group may be 3 to 60, specifically 3 to 40, and more specifically 5 to 20.
  • the heterocycloalkyl group contains O, S, Se, N or Si as a hetero atom, contains a monocyclic or polycyclic ring having 2 to 60 carbon atoms, and may be further substituted by another substituent.
  • polycyclic refers to a group in which a heterocycloalkyl group is directly connected to or condensed with another ring group.
  • the other ring group may be a heterocycloalkyl group, but may also be another type of ring group, such as a cycloalkyl group, an aryl group, or a heteroaryl group.
  • the carbon number of the heterocycloalkyl group may be 2 to 60, specifically 2 to 40, and more specifically 3 to 20.
  • the aryl group includes a monocyclic or polycyclic ring having 6 to 60 carbon atoms, and may be further substituted by another substituent.
  • polycyclic refers to a group in which an aryl group is directly connected to or condensed with another ring group.
  • the other ring group may be an aryl group, but may also be another type of ring group, such as a cycloalkyl group, heterocycloalkyl group, heteroaryl group, etc.
  • the aryl group may include a spiro group.
  • the aryl group may have 6 to 60 carbon atoms, specifically 6 to 40 carbon atoms, and more specifically 6 to 25 carbon atoms.
  • aryl group examples include phenyl group, biphenyl group, terphenyl group, naphthyl group, anthryl group, chrysenyl group, phenanthrenyl group, perylenyl group, fluoranthenyl group, triphenylenyl group, phenalenyl group, and pyrethyl group.
  • Nyl group tetracenyl group, pentacenyl group, fluorenyl group, indenyl group, acenaphthylenyl group, benzofluorenyl group, spirobifluorenyl group, 2,3-dihydro-1H-indenyl group, and condensed rings thereof etc., but is not limited to this.
  • the phosphine oxide group includes diphenylphosphine oxide group, dinaphthylphosphine oxide, etc., but is not limited thereto.
  • the silyl group is a substituent that contains Si and is directly connected to the Si atom as a radical, and is represented by -SiR101R102R103, and R101 to R103 are the same or different from each other, and are each independently hydrogen; heavy hydrogen; halogen group; Alkyl group; alkenyl group; Alkoxy group; Cycloalkyl group; Aryl group; And it may be a substituent consisting of at least one of a heterocyclic group.
  • silyl groups include trimethylsilyl group, triethylsilyl group, t-butyldimethylsilyl group, vinyldimethylsilyl group, propyldimethylsilyl group, triphenylsilyl group, diphenylsilyl group, and phenylsilyl group. It is not limited.
  • the fluorenyl group may be substituted, and adjacent substituents may combine with each other to form a ring.
  • a spiro group is a group containing a spiro structure and may have 15 to 60 carbon atoms.
  • the spiro group may include a structure in which a 2,3-dihydro-1H-indene group or a cyclohexane group is spiro bonded to a fluorenyl group.
  • the spiro group below may include any one of the groups of the structural formula below.
  • the heteroaryl group contains S, O, Se, N or Si as a hetero atom, contains a monocyclic or polycyclic ring having 2 to 60 carbon atoms, and may be further substituted by another substituent.
  • the polycyclic refers to a group in which a heteroaryl group is directly connected to or condensed with another ring group.
  • the other ring group may be a heteroaryl group, but may also be another type of ring group, such as a cycloalkyl group, heterocycloalkyl group, or aryl group.
  • the carbon number of the heteroaryl group may be 2 to 60, specifically 2 to 40, and more specifically 3 to 25.
  • heteroaryl group examples include pyridyl group, pyrrolyl group, pyrimidyl group, pyridazinyl group, furanyl group, thiophenyl group, imidazolyl group, pyrazolyl group, oxazolyl group, isoxazolyl group, and thiazolyl group.
  • isothiazolyl group triazolyl group, furazanyl group, oxadiazolyl group, thiadiazolyl group, dithiazolyl group, tetrazolyl group, pyranyl group, thiopyranyl group, diazinyl group, oxazinyl group, Thiazinyl group, deoxynyl group, triazinyl group, tetrazinyl group, quinolyl group, isoquinolyl group, quinazolinyl group, isoquinazolinyl group, quinozolyryl group, naphthyridyl group, acridinyl group, phenanthridinyl group , imidazopyridinyl group, diazanaphthalenyl group, triazindenyl group, 2-indolyl group, indolizinyl group, benzothiazolyl group, benzoxazolyl group, benzimidazolyl group, benzo
  • the amine group is a monoalkylamine group; monoarylamine group; Monoheteroarylamine group; -NH 2 ; dialkylamine group; Diarylamine group; Diheteroarylamine group; Alkylarylamine group; Alkylheteroarylamine group; and an arylheteroarylamine group, and the number of carbon atoms is not particularly limited, but is preferably 1 to 30.
  • amine group examples include methylamine group, dimethylamine group, ethylamine group, diethylamine group, phenylamine group, naphthylamine group, biphenylamine group, dibiphenylamine group, anthracenylamine group, 9- Methyl-anthracenylamine group, diphenylamine group, phenylnaphthylamine group, ditolylamine group, phenyltolylamine group, triphenylamine group, biphenylnaphthylamine group, phenylbiphenylamine group, biphenyl fluorescein Examples include a nylamine group, phenyltriphenylenylamine group, and biphenyltriphenylenylamine group, but are not limited thereto.
  • an arylene group refers to an aryl group having two bonding positions, that is, a bivalent group.
  • the description of the aryl group described above can be applied, except that each of these is a divalent group.
  • a heteroarylene group means that a heteroaryl group has two bonding positions, that is, a bivalent group. The description of the heteroaryl group described above can be applied, except that each of these is a divalent group.
  • an “adjacent” group may mean a substituent substituted on an atom directly connected to the atom on which the substituent is substituted, a substituent located closest to the substituent in terms of structure, or another substituent substituted on the atom on which the substituent is substituted. You can. For example, two substituents substituted at ortho positions in a benzene ring and two substituents substituted on the same carbon in an aliphatic ring can be interpreted as “adjacent” groups.
  • “when a substituent is not indicated in the chemical formula or compound structure” means that a hydrogen atom is bonded to a carbon atom.
  • deuterium 2H , Deuterium
  • some hydrogen atoms may be deuterium.
  • “when a substituent is not indicated in the chemical formula or compound structure” may mean that all positions that can appear as substituents are hydrogen or deuterium. That is, in the case of deuterium, it is an isotope of hydrogen, and some hydrogen atoms may be the isotope deuterium, and in this case, the content of deuterium may be 0% to 100%.
  • deuterium is one of the isotopes of hydrogen and is an element that has a deuteron consisting of one proton and one neutron as its nucleus.
  • Hydrogen- It can be expressed as 2, and the element symbol can also be written as D or 2 H.
  • isotopes refer to atoms having the same atomic number (Z) but different mass numbers (A). Isotopes have the same number of protons but do not contain neutrons. It can also be interpreted as an element with a different number of neutrons.
  • the deuterium content of 20% in the phenyl group represented by can mean that the total number of substituents that the phenyl group can have is 5 (T1 in the formula), and the number of deuteriums among them is 1 (T2 in the formula). . That is, it can be expressed by the following structural formula, which means that the deuterium content in the phenyl group is 20%.
  • a phenyl group with a deuterium content of 0% may mean a phenyl group that does not contain deuterium atoms, that is, has 5 hydrogen atoms.
  • the C6 to C60 aromatic hydrocarbon ring refers to a compound containing an aromatic ring consisting of C6 to C60 carbons and hydrogen, for example, benzene, biphenyl, terphenyl, triphenylene, naphthalene, Anthracene, phenalene, phenanthrene, fluorene, pyrene, chrysene, perylene, azulene, etc. may be mentioned, but are not limited to these, and aromatic hydrocarbon ring compounds known in the art that satisfy the above carbon number may be used. Includes all.
  • the present invention provides a heterocyclic compound represented by the following formula (1):
  • At least one of R2 to R12 is a group represented by the following formula (2),
  • R13 and R14 are -CRaRbRc, and Ra to Rc are the same or different from each other and are each independently hydrogen; heavy hydrogen; halogen; Cyano group; Substituted or unsubstituted C1 to C60 alkyl group; Substituted or unsubstituted C2 to C60 alkenyl group; Substituted or unsubstituted C2 to C60 alkynyl group; Substituted or unsubstituted C1 to C60 alkoxy group; Substituted or unsubstituted C3 to C60 cycloalkyl group; And a substituted or unsubstituted C2 to C60 heterocycloalkyl group; selected from the group consisting of,
  • L1 and L2 are the same or different from each other and are each independently a single bond; Substituted or unsubstituted C6 to C60 arylene group; Or a substituted or unsubstituted C2 to C60 heteroarylene group;
  • Ar1 and Ar2 are the same or different from each other, and are each independently a substituted or unsubstituted aryl group of C6 to C60; Or a substituted or unsubstituted C2 to C60 heteroaryl group;
  • n are the same as or different from each other and are each independently an integer from 0 to 3,
  • R1 to R12 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; halogen; Cyano group; Substituted or unsubstituted C1 to C20 alkyl group; Substituted or unsubstituted C2 to C20 alkenyl group; Substituted or unsubstituted C2 to C20 alkynyl group; A substituted or unsubstituted C1 to C20 alkoxy group; Substituted or unsubstituted C3 to C20 cycloalkyl group; Substituted or unsubstituted C2 to C20 heterocycloalkyl group; Substituted or unsubstituted C6 to C20 aryl group; Substituted or unsubstituted C2 to C20 heteroaryl group; and a group represented by the following formula (2), wherein at least one of R2 to R12 may be a group represented by the formula (2), wherein at least one
  • R1 is hydrogen; heavy hydrogen; halogen; Cyano group; Substituted or unsubstituted C1 to C30 alkyl group; Substituted or unsubstituted C2 to C30 alkenyl group; Substituted or unsubstituted C2 to C30 alkynyl group; Substituted or unsubstituted C1 to C30 alkoxy group; Substituted or unsubstituted C3 to C30 cycloalkyl group; Substituted or unsubstituted C2 to C30 heterocycloalkyl group; Substituted or unsubstituted C6 to C30 aryl group; Or a substituted or unsubstituted C2 to C30 heteroaryl group;
  • R1 is hydrogen; heavy hydrogen; halogen; Cyano group; Substituted or unsubstituted C1 to C20 alkyl group; Substituted or unsubstituted C2 to C20 alkenyl group; Substituted or unsubstituted C2 to C20 alkynyl group; A substituted or unsubstituted C1 to C20 alkoxy group; Substituted or unsubstituted C3 to C20 cycloalkyl group; Substituted or unsubstituted C2 to C20 heterocycloalkyl group; Substituted or unsubstituted C6 to C20 aryl group; Or a substituted or unsubstituted C2 to C20 heteroaryl group.
  • R1 is hydrogen; heavy hydrogen; halogen; Cyano group; Substituted or unsubstituted C6 to C20 aryl group; Or a substituted or unsubstituted C2 to C20 heteroaryl group.
  • R1 is hydrogen; heavy hydrogen; halogen; Cyano group; Substituted or unsubstituted phenyl group; Substituted or unsubstituted biphenyl group; Substituted or unsubstituted terphenyl group; Substituted or unsubstituted dibenzofuranyl group; Substituted or unsubstituted dibenzothiophenyl group; Or it may be a substituted or unsubstituted dibenzocarbazolyl group.
  • At least one of R2 to R8 may be a group represented by the following formula (2):
  • any one of R2 to R4 is a group represented by Formula 2, and R1 and R5 to R8 are each independently hydrogen; heavy hydrogen; halogen; Cyano group; Substituted or unsubstituted C1 to C30 alkyl group; Substituted or unsubstituted C2 to C30 alkenyl group; Substituted or unsubstituted C2 to C30 alkynyl group; Substituted or unsubstituted C1 to C30 alkoxy group; Substituted or unsubstituted C3 to C30 cycloalkyl group; Substituted or unsubstituted C2 to C30 heterocycloalkyl group; Substituted or unsubstituted C6 to C30 aryl group; and a substituted or unsubstituted C2 to C30 heteroaryl group.
  • any one of R2 to R4 is a group represented by Formula 2, and R1 and R5 to R8 are each independently hydrogen; heavy hydrogen; halogen; Cyano group; Substituted or unsubstituted C1 to C20 alkyl group; Substituted or unsubstituted C2 to C20 alkenyl group; Substituted or unsubstituted C2 to C20 alkynyl group; A substituted or unsubstituted C1 to C20 alkoxy group; Substituted or unsubstituted C3 to C20 cycloalkyl group; Substituted or unsubstituted C2 to C20 heterocycloalkyl group; Substituted or unsubstituted C6 to C20 aryl group; and a substituted or unsubstituted C2 to C20 heteroaryl group.
  • any one of R2 to R4 is a group represented by Formula 2, and R1 and R5 to R8 are each independently hydrogen; heavy hydrogen; halogen; Cyano group; Substituted or unsubstituted phenyl group; Substituted or unsubstituted biphenyl group; Substituted or unsubstituted terphenyl group; Substituted or unsubstituted naphthyl group; Substituted or unsubstituted phenanthrenyl group; Substituted or unsubstituted triphenylenyl group; Substituted or unsubstituted dibenzofuranyl group; Substituted or unsubstituted dibenzothiophenyl group; Or it may be a substituted or unsubstituted dibenzocarbazolyl group.
  • any one of R5 to R8 is a group represented by Formula 2, and R1 to R4 are each independently hydrogen; heavy hydrogen; halogen; Cyano group; Substituted or unsubstituted C1 to C30 alkyl group; Substituted or unsubstituted C2 to C30 alkenyl group; Substituted or unsubstituted C2 to C30 alkynyl group; Substituted or unsubstituted C1 to C30 alkoxy group; Substituted or unsubstituted C3 to C30 cycloalkyl group; Substituted or unsubstituted C2 to C30 heterocycloalkyl group; Substituted or unsubstituted C6 to C30 aryl group; and a substituted or unsubstituted C2 to C30 heteroaryl group.
  • any one of R5 to R8 is a group represented by Formula 2, and R1 to R4 are each independently hydrogen; heavy hydrogen; halogen; Cyano group; Substituted or unsubstituted C1 to C20 alkyl group; Substituted or unsubstituted C2 to C20 alkenyl group; Substituted or unsubstituted C2 to C20 alkynyl group; A substituted or unsubstituted C1 to C20 alkoxy group; Substituted or unsubstituted C3 to C20 cycloalkyl group; Substituted or unsubstituted C2 to C20 heterocycloalkyl group; Substituted or unsubstituted C6 to C20 aryl group; and a substituted or unsubstituted C2 to C20 heteroaryl group.
  • any one of R5 to R8 is a group represented by Formula 2, and R1 to R4 are each independently hydrogen; heavy hydrogen; halogen; Cyano group; Substituted or unsubstituted phenyl group; Substituted or unsubstituted biphenyl group; Substituted or unsubstituted terphenyl group; Substituted or unsubstituted naphthyl group; Substituted or unsubstituted phenanthrenyl group; Substituted or unsubstituted triphenylenyl group; Substituted or unsubstituted dibenzofuranyl group; Substituted or unsubstituted dibenzothiophenyl group; Or it may be a substituted or unsubstituted dibenzocarbazolyl group.
  • R13 and R14 are -CRaRbRc, and Ra to Rc are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; halogen; Cyano group; Substituted or unsubstituted C1 to C30 alkyl group; Substituted or unsubstituted C2 to C30 alkenyl group; Substituted or unsubstituted C2 to C30 alkynyl group; Substituted or unsubstituted C1 to C30 alkoxy group; Substituted or unsubstituted C3 to C30 cycloalkyl group; and a substituted or unsubstituted C2 to C30 heterocycloalkyl group.
  • R13 and R14 are -CRaRbRc, and Ra to Rc are the same or different from each other and are each independently hydrogen; heavy hydrogen; halogen; Cyano group; Substituted or unsubstituted C1 to C10 alkyl group; Substituted or unsubstituted C2 to C10 alkenyl group; Substituted or unsubstituted C2 to C10 alkynyl group; Substituted or unsubstituted C1 to C10 alkoxy group; Substituted or unsubstituted C3 to C10 cycloalkyl group; and a substituted or unsubstituted C2 to C10 heterocycloalkyl group.
  • R13 and R14 are -CRaRbRc, and Ra to Rc are the same or different from each other and are each independently hydrogen; heavy hydrogen; halogen; And cyano group; may be selected from the group consisting of.
  • L1 and L2 are the same or different from each other and are each independently a single bond; Substituted or unsubstituted C6 to C30 arylene group; Or it may be a substituted or unsubstituted C2 to C30 heteroarylene group.
  • L1 and L2 are the same or different from each other and are each independently a single bond; Substituted or unsubstituted C6 to C20 arylene group; Or a substituted or unsubstituted C2 to C20 heteroarylene group;
  • L1 and L2 are the same or different from each other and are each independently a single bond; Substituted or unsubstituted phenylene group; Substituted or unsubstituted biphenylene group; Or it may be a substituted or unsubstituted terphenylene group.
  • Ar1 and Ar2 are the same or different from each other, and are each independently a substituted or unsubstituted C6 to C30 aryl group; Or a substituted or unsubstituted C2 to C30 heteroaryl group;
  • Ar1 and Ar2 are the same or different from each other, and are each independently a substituted or unsubstituted C6 to C20 aryl group; Or a substituted or unsubstituted C2 to C20 heteroaryl group.
  • Ar1 and Ar2 are the same or different from each other, and are each independently a substituted or unsubstituted phenyl group; Substituted or unsubstituted biphenyl group; Substituted or unsubstituted terphenyl group; Substituted or unsubstituted naphthyl group; Substituted or unsubstituted phenanthrenyl group; Substituted or unsubstituted triphenylenyl group; Substituted or unsubstituted fluorenyl group; Substituted or unsubstituted dibenzofuranyl group; Substituted or unsubstituted dibenzothiophenyl group; Or it may be a substituted or unsubstituted dibenzocarbazolyl group.
  • Ar1 and Ar2 are the same or different from each other, and the case where Ar1 or Ar2 is a 9,9-diphenylfluorenyl group may be excluded. More specifically, Ar1 or Ar2 is excluded to include a compound represented by any of the following compounds:
  • the compound represented by Formula 1 may not contain deuterium as a substituent, or the content of deuterium relative to the total number of hydrogen atoms and deuterium atoms may be, for example, greater than 0%, 1%. It may be 10% or more, 20% or more, 30% or more, 40% or more, or 50% or more, and may be 100% or less, 90% or less, 80% or less, 70% or less, and 60% or less.
  • the compound represented by Formula 1 may not contain deuterium, or the content of deuterium relative to the total number of hydrogen and deuterium atoms may be 1% to 100%.
  • the compound represented by Formula 1 may not contain deuterium, or the content of deuterium relative to the total number of hydrogen and deuterium atoms may be 20% to 90%.
  • the compound represented by Formula 1 may not contain deuterium, or the content of deuterium relative to the total number of hydrogen and deuterium atoms may be 30% to 80%.
  • the compound represented by Formula 1 may not contain deuterium, or the content of deuterium relative to the total number of hydrogen and deuterium atoms may be 40% to 70%.
  • the deuterium content is 0% or more, 1% or more, 5% or more, 10% or more, 15% or more, 20% or more. It can be more than 25%, more than 30%, more than 35%, more than 40%, more than 45%, or more than 50%, and less than 100%, less than 95%, less than 90%, less than 85%, less than 80%, 75 It may be % or less, 70% or less, 65% or less, or 60% or less.
  • the heterocyclic compound represented by Formula 1 may be any one selected from the group consisting of the following compounds:
  • a compound having the unique properties of the introduced substituent can be synthesized.
  • substituents mainly used in the hole injection layer material, hole transport layer material, hole transport auxiliary layer material, electron blocking layer material, light emitting layer material, electron transport layer material, hole blocking layer material, and electron injection layer material used in manufacturing organic light emitting devices By introducing into the core structure, a material that satisfies the conditions required for each organic layer can be synthesized.
  • the energy band gap can be finely adjusted, while the properties at the interface between organic materials can be improved and the uses of the material can be diversified.
  • Another embodiment of the present invention provides an organic light-emitting device including the heterocyclic compound represented by Formula 1 above.
  • the “organic light emitting device” may be expressed by terms such as “organic light emitting diode”, “OLED (Organic Light Emitting Diodes)”, “OLED device”, “organic electroluminescent device”, etc.
  • the present invention includes a first electrode; a second electrode provided opposite to the first electrode; and one or more organic material layers provided between the first electrode and the second electrode, wherein at least one layer of the organic material layers includes a heterocyclic compound represented by Formula 1. do.
  • the first electrode may be an anode
  • the second electrode may be a cathode
  • the first electrode may be a cathode
  • the second electrode may be an anode
  • the organic light-emitting device may be a red organic light-emitting device, and the heterocyclic compound represented by Formula 1 may be used as a material for the red organic light-emitting device.
  • the organic light-emitting device may be a green organic light-emitting device, and the heterocyclic compound represented by Formula 1 may be used as a material for the green organic light-emitting device.
  • the organic light-emitting device may be a blue organic light-emitting device, and the heterocyclic compound represented by Formula 1 may be used as a material for the blue organic light-emitting device.
  • the organic light-emitting device may be a red organic light-emitting device, and the heterocyclic compound represented by Formula 1 may be used as a light-emitting layer material of the red organic light-emitting device.
  • the organic light-emitting device may be a green organic light-emitting device, and the heterocyclic compound represented by Formula 1 may be used as a light-emitting layer material of the green organic light-emitting device.
  • the organic light-emitting device may be a blue organic light-emitting device, and the heterocyclic compound represented by Formula 1 may be used as a light-emitting layer material of the blue organic light-emitting device.
  • heterocyclic compound represented by Formula 1 Specific details about the heterocyclic compound represented by Formula 1 are the same as described above.
  • the organic light-emitting device of the present invention can be manufactured using conventional organic light-emitting device manufacturing methods and materials, except that one or more organic material layers are formed using the heterocyclic compound described above.
  • the heterocyclic compound can form an organic material layer by a solution coating method as well as a vacuum deposition method when manufacturing an organic light-emitting device.
  • the solution application method refers to spin coating, dip coating, inkjet printing, screen printing, spraying, roll coating, etc., but is not limited to these.
  • the organic material layer of the organic light emitting device of the present invention may have a single-layer structure, but may also have a multi-layer structure in which two or more organic material layers are stacked.
  • the organic light emitting device of the present invention may have a structure including a hole injection layer, a hole transport layer, a hole transport auxiliary layer, a light emitting layer, an electron injection layer, an electron transport layer, a battery blocking layer, a hole blocking layer, etc. as organic material layers.
  • the structure of the organic light emitting device is not limited to this and may include a smaller number of organic material layers.
  • the organic material layer includes a light-emitting layer
  • the light-emitting layer may include a heterocyclic compound represented by Formula 1 above.
  • the heterocyclic compound When the heterocyclic compound is used in the light-emitting layer, strong charge transfer is possible by spatially separating HOMO (Highest Occupied Molecular Orbital) and LUMO (Lowest Unoccupied Molecular Orbital), thereby driving the organic light-emitting device. Efficiency and lifespan can be improved.
  • the organic light-emitting device may include one or more organic material layers, the organic material layer may include a light-emitting layer, and the light-emitting layer may include a heterocyclic compound represented by Formula 1. there is.
  • the organic layer may include a light-emitting layer, the light-emitting layer may include a host material, and the host material may include the heterocyclic compound.
  • the organic light emitting device has one or two or more layers selected from the group consisting of a light emitting layer, a hole injection layer, a hole transport layer, an electron injection layer, an electron transport layer, a battery blocking layer, and a hole blocking layer. More may be included.
  • the organic light-emitting device may include one or more organic material layers, the organic material layer may include a hole transport layer, and the hole transport layer includes a heterocyclic compound represented by Formula 1. can do.
  • the organic light emitting device has one or two layers selected from the group consisting of a light emitting layer, a hole injection layer, a hole transport auxiliary layer, an electron injection layer, an electron transport layer, a battery blocking layer, and a hole blocking layer. It may include more than the above.
  • the organic light-emitting device may include one or more organic material layers, the organic material layer may include a hole transport auxiliary layer, and the hole transport auxiliary layer is a heterogeneous material represented by Formula 1. It may contain a ring compound.
  • the organic light emitting device has one or two or more layers selected from the group consisting of a light emitting layer, a hole injection layer, a hole transport layer, an electron injection layer, an electron transport layer, a battery blocking layer, and a hole blocking layer. More may be included.
  • the organic light-emitting device may include one or more organic material layers, the organic material layer may include an electron blocking layer, and the electron blocking layer is a heterocyclic compound represented by Formula 1. may include.
  • the organic light emitting device has one or two or more layers selected from the group consisting of a light emitting layer, a hole injection layer, a hole transport layer, a hole transport auxiliary layer, an electron injection layer, an electron transport layer, and a hole blocking layer. It may further include.
  • the organic material layer includes a heterocyclic compound represented by Formula 1, and can be used together with a phosphorescent dopant.
  • phosphorescent dopant material those known in the art can be used.
  • phosphorescent dopant materials represented by LL'MX', LL'L"M, LMX'X", L 2 MX' and L 3 M can be used, but the scope of the present invention is not limited by these examples. .
  • the M may be iridium, platinum, osmium, etc.
  • L is an anionic bidentate ligand coordinated to M by an sp 2 carbon and a hetero atom, and X may function to trap electrons or holes.
  • Non-limiting examples of L, L' and L" include 2-(1-naphthyl)benzoxazole, 2-phenylbenzoxazole, 2-phenylbenzothiazole, 7,8-benzoquinoline, phenylpyridine, benzothiazole Thiophenylpyridine, 3-methoxy-2-phenylpyridine, thiophenylpyridine, tolylpyridine, etc.
  • Non-limiting examples of X' and These include silidene, picolinate, and 8-hydroxyquinolinate.
  • the organic material layer includes a heterocyclic compound represented by Formula 1, and can be used together with an iridium-based dopant.
  • a green phosphorescent dopant or a red phosphorescent dopant may be Ir(ppy) 3 as the iridium-based dopant.
  • the content of the dopant may be 1% to 15%, preferably 2% to 10%, more preferably 3% to 7%, based on the total weight of the light emitting layer. .
  • the organic material layer includes a hole transport layer or a hole transport auxiliary layer, and the hole transport layer or the hole transport auxiliary layer may include a heterocyclic compound represented by Formula 1 above. .
  • the organic material layer includes an electron injection layer or an electron transport layer, and the electron injection layer or the electron transport layer may include a heterocyclic compound represented by Formula 1 above.
  • the organic material layer includes an electron blocking layer or a hole blocking layer, and the electron blocking layer or the hole blocking layer may include a heterocyclic compound represented by Formula 1 above. .
  • the organic material layer includes an electron transport layer, a light-emitting layer, or a hole blocking layer, and the electron transport layer, the light-emitting layer, or the hole blocking layer may include a heterocyclic compound represented by Formula 1. You can.
  • the organic material layer includes a light-emitting layer, and the light-emitting layer may include a heterocyclic compound represented by Formula 1 above.
  • the organic material layer includes a light-emitting layer
  • the light-emitting layer includes a host material
  • the host material may include a heterocyclic compound represented by Formula 1.
  • the light emitting layer may include two or more host materials, and at least one of the host materials may include a heterocyclic compound represented by Formula 1 above.
  • the light-emitting layer may be used by pre-mixing two or more host materials, and at least one of the two or more host materials is a heterogeneous compound represented by Formula 1. It may contain a ring compound.
  • the pre-mixed means that the light emitting layer first mixes two or more host materials into one container before depositing them on the organic layer.
  • the organic light emitting device may further include one or two or more layers selected from the group consisting of a light emitting layer, a hole injection layer, a hole transport layer, an electron injection layer, an electron blocking layer, and a hole blocking layer. .
  • FIG. 1 to 3 illustrate the stacking order of electrodes and organic material layers of an organic light-emitting device according to an embodiment of the present invention.
  • the scope of the present application be limited by these drawings, and structures of organic light-emitting devices known in the art may also be applied to the present application.
  • an organic light emitting device is shown in which an anode 200, an organic material layer 300, and a cathode 400 are sequentially stacked on a substrate 100.
  • an organic light-emitting device may be implemented in which a cathode, an organic material layer, and an anode are sequentially stacked on a substrate, as shown in FIG. 2.
  • FIG. 3 illustrates the case where the organic material layer is multi-layered.
  • the organic light emitting device according to FIG. 3 includes a hole injection layer 301, a hole transport layer 302, a light emitting layer 303, a hole blocking layer 304, an electron transport layer 305, and an electron injection layer 306.
  • the scope of the present application is not limited by this laminated structure, and if necessary, the remaining layers except the light-emitting layer may be omitted, and other necessary functional layers may be added.
  • the step of forming the organic layer may include pre-mixing the heterocyclic compound represented by Formula 1 and forming it using a thermal vacuum deposition method.
  • the pre-mixed means mixing the materials in one source before depositing the heterocyclic compound represented by Formula 1 on the organic layer.
  • the premixed material may be referred to as a heterocyclic compound according to an exemplary embodiment of the present application.
  • the organic material layer containing the heterocyclic compound represented by Formula 1 may further include other materials as needed.
  • anode material materials with a relatively large work function can be used, and transparent conductive oxides, metals, or conductive polymers can be used.
  • the anode material include metals such as 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); Combination of metal and oxide such as ZnO:Al or SnO2:Sb; Conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene](PEDOT), polypyrrole, and polyaniline are included, but are not limited to these.
  • the cathode material materials with a relatively low work function can be used, and metals, metal oxides, or conductive polymers can be used.
  • specific examples of the cathode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead, or alloys thereof; There are, but are not limited to, multi-layered materials such as LiF/Al or LiO 2 /Al.
  • hole injection layer material known hole injection layer materials may be used, for example, phthalocyanine compounds such as copper phthalocyanine disclosed in U.S. Patent No. 4,356,429 or those described in Advanced Material, 6, p.677 (1994). Described starburst-type amine derivatives, such as tris(4-carbazoyl-9-ylphenyl)amine (TCTA), 4,4',4"-tri[phenyl(m-tolyl)amino]triphenylamine ( m-MTDATA), 1,3,5-tris[4-(3-methylphenylphenylamino)phenyl]benzene (m-MTDAPB), polyaniline/dodecylbenzenesulfonic acid, a soluble conductive polymer, or Poly(3,4-ethylenedioxythiophene)/Poly(4-styrenesulfonate), Polyaniline/Camphor sulfonic acid, or Polyaniline/Poly(4-(4
  • hole transport layer material pyrazoline derivatives, arylamine derivatives, stilbene derivatives, triphenyldiamine derivatives, etc. may be used, and low molecular or high molecular materials may also be used.
  • Electron transport layer materials include oxadiazole derivatives, anthraquinodimethane and its derivatives, benzoquinone and its derivatives, naphthoquinone and its derivatives, anthraquinone and its derivatives, tetracyanoanthraquinodimethane and its derivatives, and fluorenone.
  • Derivatives, diphenyldicyanoethylene and its derivatives, diphenoquinone derivatives, metal complexes of 8-hydroxyquinoline and its derivatives, etc. may be used, and not only low molecular substances but also high molecular substances may be used.
  • LiF is typically used as an electron injection layer material in the industry, but the present application is not limited thereto.
  • Red, green, or blue light-emitting materials can be used as the light-emitting layer material, and if necessary, two or more light-emitting materials can be mixed. At this time, two or more light emitting materials can be deposited and used from individual sources, or they can be premixed and deposited from a single source. Additionally, a fluorescent material may be used as the light-emitting layer material, but it may also be used as a phosphorescent material.
  • the light emitting layer material may be a material that emits light by combining holes and electrons injected from the anode and the cathode respectively, but may also be used as a host material and a dopant material that participates in light emission together.
  • hosts of the same series may be mixed and used, or hosts of different series may be mixed and used.
  • any two or more types of materials such as an n-type host material or a p-type host material, can be selected and used as the host material of the light-emitting layer.
  • the organic light emitting device may be a front emitting type, a back emitting type, or a double-sided emitting type depending on the material used.
  • the heterocyclic compound according to an embodiment of the present invention may function in organic electronic devices, including organic solar cells, organic photoreceptors, organic transistors, etc., on a principle similar to that applied to organic light-emitting devices.
  • reaction solution was extracted with dichloromethane and distilled water, the organic layer was dried with anhydrous magnesium sulfate (MgSO 4 ), the solvent was removed using a rotary evaporator, and the solvent was purified by column chromatography using dichloromethane and hexane as developing solvents to obtain compound 001. 13g was obtained (yield 83%).
  • a glass substrate coated with a thin film of indium tinoxide (ITO) with a thickness of 1,500 ⁇ was washed with distilled water ultrasonic waves. After washing with distilled water, ultrasonic cleaning was performed with solvents such as acetone, methanol, and isopropyl alcohol, dried, and then treated with UV (Ultraviolet Ozone) for 5 minutes using UV light in a UV (Ultraviolet) cleaner. Afterwards, the substrate was transferred to a plasma cleaner (PT), then plasma treated in a vacuum to increase the work function of ITO and remove the remaining film, and then transferred to a thermal evaporation equipment for organic deposition.
  • ITO indium tinoxide
  • NPB N,N'-bis( ⁇ -naphthyl)-N,N'-diphenyl-4,4'-diamine
  • a light-emitting layer was thermally vacuum deposited thereon as follows.
  • the emitting layer uses 9-[4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl]-9'-phenyl-3,3'-bi-9 H -carbazole as a host.
  • the compound (9-[4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl]-9'-phenyl-3,3'-Bi-9 H -carbazole) was deposited at 400 ⁇ .
  • the green phosphorescent dopant was deposited by doping 7% of Ir(ppy) 3 .
  • 60 ⁇ of bathocuproine (BCP) was deposited as a hole blocking layer, and 300 ⁇ of E1 was deposited on top of it as an electron transport layer.
  • lithium fluoride (LiF) was deposited to a thickness of 10 ⁇ on the electron transport layer to form an electron injection layer, and then an aluminum (Al) cathode was deposited to a thickness of 1,200 ⁇ on the electron injection layer to form the cathode, thereby forming an organic A light emitting device was manufactured.
  • the electroluminescence (EL) characteristics of the organic light emitting device manufactured as described above were measured using McScience's M7000, and the standard luminance was measured to be 20,000 cd using the measurement results using a lifespan measurement equipment (M6000) manufactured by McScience.
  • M6000 lifespan measurement equipment
  • the organic light-emitting devices (Examples 1 to 58) using the compound represented by Formula 1 of the present invention as the hole transport layer material were the organic light emitting devices using the compounds of Comparative Examples 1 to 4 as the hole transport layer material.
  • the driving voltage is lower, and the luminous efficiency and lifespan are significantly improved.
  • the compounds M1 to M3 used in Comparative Examples 2 to 4 are similar to the compounds of Formula 1 of the present invention in that they have a dimethylfluorenobenzofuran-type 5-ring skeleton, but in the case of the compounds M1 and M3, dimethylfluoreno An arylamine substituent is introduced at the 4th position of benzofuran, and the compound of the present invention is different in that an arylamine substituent is not introduced at the 4th position.
  • an arylamine group is introduced at position 4 of the dimethylfluorenobenzofuran, there is a disadvantage that hole mobility becomes slower compared to other positions.
  • the arylamine group was introduced at a position other than the 4th position of the parent nucleus, thereby improving the physical properties of hole mobility and improving device characteristics.
  • the compound M2 used in Comparative Example 3 is similar to the compound of Formula 1 of the present invention in that it has a dimethylfluorenobenzofuran-type 5-ring skeleton, but has a 2-substituted arylamine group structure.
  • the HOMO level increases.
  • the compound of Formula 1 of the present invention has a single arylamine substituent, so its HOMO level is lower than that of the compound M2 used in Comparative Example 3.
  • the HOMO level is lowered, the HOMO level difference between the hole transport layer and the light emitting layer is reduced, making hole transport easier, and for this reason, it was confirmed that the device characteristics are improved.
  • the transparent electrode ITO thin film obtained from OLED glass was ultrasonically cleaned for 5 minutes each using trichlorethylene, acetone, ethanol, and distilled water sequentially, and then stored in isopropanol before use.
  • the ITO substrate was installed in the substrate folder of the vacuum deposition equipment, and the following 4,4',4"-tris(N,N-(2-naphthyl)-phenylamino)triphenylamine ( 4,4',4"-tris(N,N-(2-naphthyl)-phenylamino)triphenyl amine: 2-TNATA) was added.
  • the vacuum in the chamber was evacuated until it reached 10 -6 torr, and then a current was applied to the cell to evaporate 2-TNATA and a 600 ⁇ thick hole injection layer was deposited on the ITO substrate.
  • the following N,N'-bis( ⁇ -naphthyl)-N,N'-diphenyl-4,4'-diamine (N,N'-bis( ⁇ -naphthyl)-N, N'-diphenyl-4,4'-diamine: NPB) was added and evaporated by applying a current to the cell to deposit a 1000 ⁇ thick hole transport layer on the hole injection layer.
  • a compound of the following structural formula M1 was deposited to a thickness of 100 ⁇ as an electron blocking layer thereon.
  • a blue light-emitting material with the following structure was deposited as a light-emitting layer thereon. Specifically, the compound of H1, a blue light-emitting host material, was vacuum deposited to a thickness of 300 ⁇ in one cell of the vacuum deposition equipment, and the compound of D1, a blue light-emitting dopant material, was doped at 5 wt% compared to the host material and deposited on it.
  • lithium fluoride (LiF) is deposited to a thickness of 10 ⁇ as an electron injection layer on the electron transport layer, and then an aluminum (Al) cathode is deposited to a thickness of 1,000 ⁇ on the electron injection layer to form a cathode.
  • Al aluminum
  • the electroluminescence (EL) characteristics of the organic light emitting device manufactured as described above were measured using McScience's M7000, and the standard luminance was measured to be 20,000 cd using the measurement results using a lifespan measurement equipment (M6000) manufactured by McScience.
  • M6000 lifespan measurement equipment
  • Examples 59 to 89 which are organic light-emitting devices using the compound represented by Formula 1 of the present invention as the electron blocking layer material, were obtained by using compounds M1 to M3 and NPB as the electron blocking layer material. Compared to Comparative Examples 5 to 8, which were organic light emitting devices, the driving voltage was lower, and the luminous efficiency and lifespan were significantly improved.

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Abstract

La présente invention concerne un composé hétérocyclique représenté par la formule chimique 1 et un dispositif électroluminescent organique le comprenant.
PCT/KR2023/005090 2022-05-27 2023-04-14 Composé hétérocyclique et dispositif électroluminescent organique le comprenant WO2023229228A1 (fr)

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