WO2023224413A1 - Composé hétérocyclique, élément électroluminescent organique le comprenant, et composition pour couche organique d'élément électroluminescent organique - Google Patents

Composé hétérocyclique, élément électroluminescent organique le comprenant, et composition pour couche organique d'élément électroluminescent organique Download PDF

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WO2023224413A1
WO2023224413A1 PCT/KR2023/006795 KR2023006795W WO2023224413A1 WO 2023224413 A1 WO2023224413 A1 WO 2023224413A1 KR 2023006795 W KR2023006795 W KR 2023006795W WO 2023224413 A1 WO2023224413 A1 WO 2023224413A1
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이기백
모준태
김동준
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엘티소재주식회사
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    • C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
    • C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
    • C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C07D251/14—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom
    • C07D251/24—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom to three ring carbon atoms
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    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/06—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom
    • C07D213/16—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom containing only one pyridine ring
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    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/26—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
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    • C07D403/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing aromatic rings
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    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
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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
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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
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    • C07D409/10—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 linked by a carbon chain containing aromatic rings
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    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
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    • C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
    • C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
    • C07D491/04—Ortho-condensed systems
    • C07D491/044—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring
    • C07D491/048—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring the oxygen-containing ring being five-membered
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    • C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
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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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    • H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
    • H10K85/622—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing four rings, e.g. pyrene
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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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Definitions

  • the present invention relates to heterocyclic compounds, organic light-emitting devices containing the same, and compositions for organic material layers of organic light-emitting devices.
  • Organic electroluminescent devices are a type of self-luminous display devices and have the advantage 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 annihilate, 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 functions such as hole injection, hole transport, electron blocking, hole blocking, electron transport, and electron injection may be used.
  • the present invention seeks to provide a heterocyclic compound, an organic light-emitting device containing the same, and a composition for the organic material layer of the organic light-emitting device.
  • a heterocyclic compound represented by the following formula (1) is provided.
  • Et is a substituted or unsubstituted heteroaryl group containing N of C2 to C60
  • Ar1 is a substituted or unsubstituted aryl group of C6 to C60; A substituted or unsubstituted C5 to C60 polycyclic heteroaryl group; or a substituted or unsubstituted amine group, p is an integer of 1 to 4, and when p is 2 or more, the substituents in parentheses are the same or different from each other,
  • L1 and L2 are the same or different from each other and are each independently directly bonded; or a substituted or unsubstituted C6 to C60 arylene group, m and n are each an integer of 0 to 3, and when m and n are each 2 or more, the substituents in the parentheses are the same or different from each other,
  • R, R' and R" are the same or different from each other, and are each independently hydrogen; deuterium; cyano group; substituted or unsubstituted C1 to C60 alkyl group; substituted or unsubstituted C3 to C60 cycloalkyl group; substituted or An unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group,
  • R1 to R3 Two or more groups among R1 to R3 that are adjacent to each other are bonded to each other to form a substituted or unsubstituted C6 to C60 aliphatic or aromatic hydrocarbon ring; Or, it forms a substituted or unsubstituted C2 to C60 aliphatic or aromatic heterocycle.
  • a first electrode a second electrode provided opposite to the first electrode; And an organic light-emitting device comprising 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 includes a heterocyclic compound represented by Formula 1. provides.
  • an organic light-emitting device wherein the organic material layer further includes a compound represented by the following formula (2).
  • Ar2 and Ar3 are the same as or different from each other, and are each independently a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted heteroaryl group of C2 to C60, q and r are each integers of 1 to 4, and when q and r are each 2 or more, the substituents in parentheses are the same or different from each other,
  • L3 is a direct bond; Substituted or unsubstituted C6 to C60 arylene group; or a substituted or unsubstituted heteroarylene group of C2 to C60, o is each an integer of 0 to 3, and when o is 2 or more, the substituents in parentheses are the same or different from each other,
  • Ra and Rb are the same or different from each other and are each independently hydrogen; heavy hydrogen; Substituted or unsubstituted C1 to C20 alkyl group; and a substituted or unsubstituted C6 to C20 aryl group,
  • R, R' and R" are the same or different from each other, and are each independently hydrogen; deuterium; cyano group; substituted or unsubstituted C1 to C60 alkyl group; substituted or unsubstituted C3 to C60 cycloalkyl group; substituted or unsubstituted A substituted or unsubstituted C2 to C60 heteroaryl group,
  • g is an integer from 0 to 5
  • h is an integer from 0 to 4
  • the substituents in parentheses are the same or different from each other.
  • a heterocyclic compound represented by Formula 1 and a composition for the organic material layer of an organic light-emitting device comprising the compound represented by Formula 2 above.
  • the heterocyclic compounds described herein can be used as organic layer materials for organic light-emitting devices.
  • it can serve as a light emitting material, hole injection material, hole transport material, electron transport material, electron injection material, etc. in an organic light emitting device.
  • it can be used as a light-emitting layer material for organic light-emitting devices.
  • the heterocyclic compound represented by Formula 1 can be used as a light-emitting layer material of the organic material layer of an organic light-emitting device, and in particular, it can be used as an n-type host material of the light-emitting layer.
  • the heterocyclic compound represented by Formula 1 has fluorene as its basic skeleton and has a substituent with electron transfer properties.
  • the electron transport ability and hole blocking ability can be adjusted by substituting a substituent with electron transport properties at an appropriate position, thereby lowering the driving voltage of the device and improving light efficiency.
  • the hole characteristics are strengthened and the thermal stability of the compound is improved by increasing the planarity and glass transition temperature of the azine derivative, thereby improving the lifespan characteristics of the device.
  • the heterocyclic compound represented by Formula 1 may further include the compound represented by Formula 2 as a p-type host material of the light-emitting layer, and can be applied to an organic light-emitting device in a combination of the two types.
  • the compound represented by Formula 2 due to the exciplex phenomenon, holes are injected into the p-type host and electrons are injected into the p-type (n-type) host.
  • the ratio of the two types of compounds is By appropriately adjusting, the charge balance within the organic light emitting device can be balanced.
  • the driving voltage, efficiency, and lifespan of the organic light-emitting device are improved.
  • 1 to 3 are diagrams schematically showing the stacked structure of an organic light-emitting device according to an exemplary embodiment of the present application.
  • n in Cn refers to the number of carbon atoms. That is, for example, C6 to C60 means 6 to 60 carbon atoms.
  • substitution means that a hydrogen atom bonded to a carbon atom of a compound is changed to another substituent.
  • 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, and if two or more substituents are substituted. , two or more substituents may be the same or different from each other.
  • “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%.
  • the content of deuterium is 0%, the content of hydrogen is 100%, and all substituents are hydrogen, etc., explicitly excluding deuterium. Otherwise, hydrogen and deuterium can be used together in compounds.
  • 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 means that the total number of substituents that the phenyl group can have is 5 (T1 in the formula), and if the number of deuteriums among them is 1 (T2 in the formula), it will be expressed as 20%. You can. That is, the deuterium content of 20% in the phenyl group can be expressed by the following structural formula.
  • 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.
  • 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, octyl group, n-octyl group, tert-octyl group, 1-methylheptyl group Ty
  • 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 to these.
  • 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.
  • a haloalkyl group refers to an alkyl group substituted with a halogen group, and specific examples include -CF 3 and -CF 2 CF 3 , but are not limited thereto.
  • the alkoxy group is represented by -O(R101), and examples of the above-described alkyl group may be applied to R101.
  • the aryloxy group is represented by -O(R102), and examples of the above-described aryl groups may be applied to R102.
  • alkylthioxy group is represented by -S(R103), and examples of the alkyl groups described above may be applied to R103.
  • the arylthioxy group is represented by -S(R104), and examples of the above-described aryl groups may be applied to R104.
  • 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 includes 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, and phenalenyl group.
  • pyrenyl group, tetracenyl group, pentacenyl group, fluorenyl group, indenyl group, acenaphthylenyl group, benzofluorenyl group, spirobifluorenyl group, 2,3-dihydro-1H-indenyl group, these Condensation ring groups, etc. may be included, but are not limited thereto.
  • terphenyl group may be selected from the following structures.
  • the fluorenyl group may be substituted, and adjacent substituents may combine with each other to form a ring.
  • 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 pyridine group, pyrrole group, pyrimidine group, pyridazine group, furan group, thiophene group, imidazole group, pyrazole group, oxazole group, isoxazole group, thiazole group, isothiazole group, Triazole group, furazine group, oxadiazole group, thiadiazole group, dithiazole group, tetrazolyl group, pyran group, thiopyran group, diazine group, oxazine group, thiazine group, dioxine group, triazine group, tetrazine group, quinoline group, Isoquinoline group, quinazoline group, isoquinazoline group, quinozoline group, naphthyridine group, acridine group, phenanthridine group, imidazopyridine group, diazanaphthalene group, triazindene
  • an additional substituent may be substituted on the nitrogen or carbon of the carbazole.
  • benzocarbazole group may have any one of the following structures.
  • the dibenzocarbazole group may have any one of the following structures.
  • the naphthobenzofuran group may have any of the following structures.
  • the naphthobenzothiophene group may have any one of the following structures.
  • the silyl group is a substituent that contains Si and is directly connected to the Si atom as a radical, and is represented by -Si(R107)(R108)(R109), and R107 to R109 are the same or different from each other, and each independently hydrogen; heavy hydrogen; halogen group; Alkyl group; alkenyl group; Alkoxy group; Cycloalkyl group; heterocycloalkyl group; Aryl group; And it may be a substituent consisting of at least one of a heteroaryl group.
  • silyl groups include: (trimethylsilyl group), (triethylsilyl group), (t-butyldimethylsilyl group), (vinyldimethylsilyl group), (propyldimethylsilyl group), (triphenylsilyl group), (diphenylsilyl group), (phenylsilyl group), etc., but is not limited thereto.
  • the phosphine oxide group includes, but is not limited to, dimethylphosphine oxide, diphenylphosphine oxide, and dinaphthylphosphine oxide.
  • the amine group is represented by -N(R112)(R113), and R112 and R113 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; heterocycloalkyl group; Aryl group; And it may be a substituent consisting of at least one of a heteroaryl group.
  • the amine group is -NH 2 ; Monoalkylamine group; monoarylamine group; Monoheteroarylamine group; 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 to these.
  • the examples of the aryl group described above may be applied, except that the arylene group is a divalent group.
  • heteroaryl group described above may be applied, except that the heteroarylene group 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 at the same carbon in an aliphatic ring can be interpreted as “adjacent” groups.
  • Hydrocarbon rings and heterocycles that can be formed by adjacent groups include aliphatic hydrocarbon rings, aromatic hydrocarbon rings, aliphatic heterocycles, and aromatic heterocycles, and the rings are each of the above-described cycloalkyl groups and aryl groups, except that they are not monovalent. Structures exemplified by groups, heterocycloalkyl groups, and heteroaryl groups can be applied.
  • a heterocyclic compound represented by Formula 1 is provided.
  • a group not indicated as a substituent may mean that all groups represented by hydrogen can be replaced by deuterium. i.e. hydrogen; Alternatively, it may indicate that deuterium can be substituted for each other.
  • the deuterium content of the heterocyclic compound represented by Formula 1 may be 0% to 100%.
  • heterocyclic compounds represented by Formula 1 of the present invention compounds substituted with deuterium have a lower ground state energy compared to compounds substituted with hydrogen, and as the bond length between carbon and deuterium becomes shorter, the molecular center becomes shorter.
  • the volume Molecular hardcore volume
  • electrical polarizability can be reduced and the volume of the device thin film can be increased by making intermolecular interaction weaker.
  • These characteristics create an amorphous state in the thin film, leading to the effect of lowering the degree of crystallinity. Therefore, among the heterocyclic compounds represented by Formula 1, compounds substituted with deuterium can be effective in improving the heat resistance of OLED (Organic Light Emitting Diodes) devices, thereby improving their lifespan and driving characteristics.
  • OLED Organic Light Emitting Diodes
  • the 'OLED device' may be expressed by terms such as 'organic light emitting diode', 'OLED (Organic Light Emitting Diodes)', 'organic light emitting device', and 'organic electroluminescent device'.
  • Et of Formula 1 may be a substituted or unsubstituted heteroaryl group containing N of C2 to C60.
  • Et may be a substituted or unsubstituted heteroaryl group containing N of C2 to C40.
  • Et may be a substituted or unsubstituted heteroaryl group containing N of C2 to C20.
  • Et is a substituted or unsubstituted pyridine group, a substituted or unsubstituted pyrimidine group; Substituted or unsubstituted triazine group; Substituted or unsubstituted phenanthroline group; Substituted or unsubstituted benzofuropyrimidine; Or it may be a substituted or unsubstituted benzothienopyrimidine.
  • Ar1 of Formula 1 is a substituted or unsubstituted aryl group of C6 to C60; A substituted or unsubstituted C5 to C60 polycyclic heteroaryl group; Or, it may be a substituted or unsubstituted amine group.
  • Ar1 is a substituted or unsubstituted aryl group of C6 to C40; A substituted or unsubstituted C5 to C40 polycyclic heteroaryl group; Or, it may be a substituted or unsubstituted amine group.
  • Ar1 is a substituted or unsubstituted C6 to C20 aryl group; A substituted or unsubstituted C5 to C20 polycyclic heteroaryl group; Or, it may be a substituted or unsubstituted amine group.
  • Ar1 is a substituted or unsubstituted phenyl group; Substituted or unsubstituted biphenyl group; Substituted or unsubstituted naphthyl group; Substituted or unsubstituted phenanthrene group; Substituted or unsubstituted terphenyl group; Substituted or unsubstituted triphenylene group; Substituted or unsubstituted dibenzofuran group; Substituted or unsubstituted dibenzothiophene group; Substituted or unsubstituted carbazole group; Substituted or unsubstituted benzocarbazole group; Alternatively, it may be an amine group substituted or unsubstituted by an aryl group.
  • Ar1 is a substituted or unsubstituted phenyl group; Substituted or unsubstituted biphenyl group; Substituted or unsubstituted naphthyl group; Substituted or unsubstituted phenanthrene group; Substituted or unsubstituted terphenyl group; Substituted or unsubstituted triphenylene group; Substituted or unsubstituted dibenzofuran group; Substituted or unsubstituted dibenzothiophene group; Substituted or unsubstituted carbazole group; Substituted or unsubstituted benzocarbazole group; Alternatively, it may be an amine group substituted or unsubstituted by a phenyl group, biphenyl group, or dimethylfluorene group.
  • p in Formula 1 is an integer of 1 to 4, and when p is 2 or more, the substituents in parentheses are the same or different from each other. In an exemplary embodiment of the present application, p is 1. In an exemplary embodiment of the present application, p is 2. In an exemplary embodiment of the present application, p is 3. In an exemplary embodiment of the present application, p is 4. That is, when p is 2 or more, Ar1 in parentheses are the same or different from each other.
  • L1 and L2 of Formula 1 are the same as or different from each other, and are each independently directly bonded; Or, it may be a substituted or unsubstituted C6 to C60 arylene group.
  • L1 and L2 are the same or different from each other and are each independently directly bonded; Or, it may be a substituted or unsubstituted C6 to C40 arylene group.
  • L1 and L2 are the same or different from each other and are each independently directly bonded; Or, it may be a substituted or unsubstituted C6 to C20 arylene group.
  • L1 and L2 are the same or different from each other and are each independently directly bonded; Substituted or unsubstituted phenylene group; Substituted or unsubstituted biphenylene group; Or it may be a substituted or unsubstituted naphthylene group.
  • n and n in Formula 1 are integers from 0 to 3, and when m and n are each 2 or more, the substituents in the parentheses are the same or different from each other.
  • m is 0. In an exemplary embodiment of the present application, m is 1. In an exemplary embodiment of the present application, m is 2. In an exemplary embodiment of the present application, m is 3. That is, when m is 2 or more, L1 in parentheses are the same or different from each other.
  • n is 0. In an exemplary embodiment of the present application, n is 1. In an exemplary embodiment of the present application, n is 2. In an exemplary embodiment of the present application, n is 3. That is, when n is 2 or more, L2 in parentheses are the same or different from each other.
  • R, R' and R" are the same or different from each other, and are each independently hydrogen; heavy hydrogen; Cyano group; Substituted or unsubstituted C1 to C60 alkyl group; Substituted or unsubstituted C3 to C60 cycloalkyl group; A substituted or unsubstituted C6 to C60 aryl group; Or it may be a substituted or unsubstituted C2 to C60 heteroaryl group.
  • R1 to R8 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; Substituted or unsubstituted C1 to C20 alkyl group; and a substituted or unsubstituted C6 to C20 aryl group, or two or more groups adjacent to each other are bonded to each other to form a substituted or unsubstituted C6 to C20 aliphatic or aromatic hydrocarbon ring or a substituted or unsubstituted C2 to C20 aryl group. It may form an aliphatic or aromatic heterocycle.
  • two or more groups adjacent to each other among R1 to R3 are bonded to each other to form a substituted or unsubstituted C6 to C60 aliphatic or aromatic hydrocarbon ring; Alternatively, it may form a substituted or unsubstituted C2 to C60 aliphatic or aromatic heterocycle.
  • two or more groups adjacent to each other among R1 to R3 are bonded to each other to form a substituted or unsubstituted C6 to C40 aliphatic or aromatic hydrocarbon ring; Alternatively, it may form a substituted or unsubstituted C2 to C40 aliphatic or aromatic heterocycle.
  • two or more groups adjacent to each other among R1 to R3 are bonded to each other to form a substituted or unsubstituted C6 to C20 aliphatic or aromatic hydrocarbon ring; Alternatively, it may form a substituted or unsubstituted C2 to C20 aliphatic or aromatic heterocycle.
  • two or more groups adjacent to each other among R1 to R3 are bonded to each other to form a substituted or unsubstituted C6 to C10 aliphatic or aromatic hydrocarbon ring; Alternatively, it may form a substituted or unsubstituted C2 to C10 aliphatic or aromatic hetero ring.
  • R7 and R8 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; Substituted or unsubstituted C1 to C20 alkyl group; and a substituted or unsubstituted C6 to C20 aryl group, or two or more groups adjacent to each other are bonded to each other to form a substituted or unsubstituted C6 to C20 aliphatic or aromatic hydrocarbon ring or a substituted or unsubstituted C2 to C20 aryl group. It may form an aliphatic or aromatic heterocycle.
  • R7 and R8 are the same as or different from each other, and are each independently a substituted or unsubstituted C1 to C20 alkyl group; Alternatively, it may be a substituted or unsubstituted C6 to C20 aryl group, or may be combined with each other to form a substituted or unsubstituted C6 to C20 aromatic hydrocarbon ring.
  • R7 and R8 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; Substituted or unsubstituted methyl group; and substituted or unsubstituted phenyl groups, or two or more groups adjacent to each other may be combined with each other to form substituted or unsubstituted fluorene.
  • Formula 1 may be represented by the following Formula 1-A or Formula 1-B.
  • R, R' and R" are the same or different from each other, and are each independently hydrogen; deuterium; cyano group; substituted or unsubstituted C1 to C60 alkyl group; substituted or unsubstituted C3 to C60 cycloalkyl group; substituted or An unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group,
  • a and b are integers from 0 to 4, and when a and b are each 2 or more, the substituents in parentheses are the same or different from each other.
  • R1, R3 to R8, R11, and R12 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; Substituted or unsubstituted C1 to C20 alkyl group; and a substituted or unsubstituted C6 to C20 aryl group, or two or more groups adjacent to each other are bonded to each other to form a substituted or unsubstituted C6 to C20 aliphatic or aromatic hydrocarbon ring or a substituted or unsubstituted C2 to C20 aryl group. It may form an aliphatic or aromatic heterocycle.
  • a and b are integers from 0 to 4, and when a and b are each 2 or more, the substituents in parentheses are the same or different from each other.
  • a is 0, 1, 2, 3, or 4, and when a is 2 or more, R11 in parentheses are the same or different from each other.
  • b is 0, 1, 2, 3, or 4, and when b is 2 or more, R12 in parentheses are the same or different from each other.
  • Formula 1 may be represented by any one of the following Formulas 1-1 to 1-3.
  • X1 to X5 are the same or different from each other, and are each independently N; or CRx, and at least one is N,
  • Y1 is O; or S,
  • Rx, R13 and R14 are hydrogen; heavy hydrogen; Substituted or unsubstituted C6 to C20 aryl group; Or a substituted or unsubstituted C2 to C20 heteroaryl group,
  • c is an integer from 0 to 7
  • d is an integer from 0 to 5
  • substituents in parentheses are the same or different from each other.
  • X1 to X5 are the same as or different from each other, and are each independently N; or CRx, and at least one may be N.
  • one of X1 to X5 may be N, and the others may be CRx.
  • two of X1 to X5 may be N, and the remainder may be CRx.
  • three of X1 to X5 may be N, and the remainder may be CRx.
  • Y1 is O; Or it may be S.
  • Y1 may be O.
  • Y1 may be S.
  • Rx, R13 and R14 are hydrogen; heavy hydrogen; Substituted or unsubstituted C6 to C20 aryl group; Or it may be a substituted or unsubstituted C2 to C20 heteroaryl group.
  • Rx, R13, and R14 are hydrogen; heavy hydrogen; Substituted or unsubstituted phenyl group; Substituted or unsubstituted biphenyl group; Substituted or unsubstituted naphthyl group; Substituted or unsubstituted dibenzothiophene group; Or it may be a substituted or unsubstituted dibentofuran group.
  • -Ar1 of Formula 1 may be represented by any one of the structures 1a to 1d below.
  • Ar11 is a substituted or unsubstituted aryl group of C6 to C20,
  • Y2 is O; or S,
  • R, R' and R" are the same or different from each other, and are each independently hydrogen; deuterium; cyano group; substituted or unsubstituted C1 to C60 alkyl group; substituted or unsubstituted C3 to C60 cycloalkyl group; substituted or An unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group,
  • e is an integer from 0 to 7
  • f is an integer from 0 to 8
  • substituents in parentheses are the same or different from each other
  • p1 to p3 are each an integer of 1 to 4, and when p1 to p3 are each 2 or more, the substituents in the parentheses are the same or different from each other,
  • Formula 1 may be represented by any one of the following Formulas 1-4 to 1-7.
  • Ar11 is a substituted or unsubstituted aryl group of C6 to C20,
  • Y2 is O; or S,
  • R, R' and R" are the same or different from each other, and are each independently hydrogen; deuterium; cyano group; substituted or unsubstituted C1 to C60 alkyl group; substituted or unsubstituted C3 to C60 cycloalkyl group; substituted or An unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group,
  • e is an integer from 0 to 7
  • f is an integer from 0 to 8
  • substituents in parentheses are the same or different from each other
  • p1 to p3 are each an integer of 1 to 4, and when p1 to p3 are each 2 or more, the substituents in the parentheses are the same or different from each other.
  • Ar11 may be a substituted or unsubstituted C6 to C20 aryl group.
  • Ar11 is a substituted or unsubstituted phenyl group; Substituted or unsubstituted biphenyl group; Substituted or unsubstituted naphthyl group; Substituted or unsubstituted phenanthrene group; Substituted or unsubstituted terphenyl group; Or it may be a substituted or unsubstituted triphenylene group.
  • p1 in Formula 1 is an integer of 1 to 4, and when p1 is 2 or more, the substituents in parentheses are the same or different from each other.
  • p1 is 1.
  • p1 is 2.
  • p1 is 3.
  • p1 is 4. That is, when p1 is 2 or more, Ar11 in parentheses are the same or different from each other.
  • Y2 is O; Or it may be S.
  • Y2 may be O.
  • Y2 may be S.
  • R15, R16, Ar12, and Ar13 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; and a substituted or unsubstituted C6 to C20 aryl group, or two or more groups adjacent to each other are bonded to each other to form a substituted or unsubstituted C6 to C20 aliphatic or aromatic hydrocarbon ring or a substituted or unsubstituted C2 to C20 aryl group. It may form an aliphatic or aromatic heterocycle.
  • p2 is an integer of 1 to 4, and when p2 is 2 or more, the substituents in parentheses are the same or different from each other. In an exemplary embodiment of the present application, p2 is 1. In an exemplary embodiment of the present application, p2 is 2. In an exemplary embodiment of the present application, p2 is 3. In an exemplary embodiment of the present application, p2 is 4. That is, when p2 is 2 or more, Ar12 in parentheses are the same or different from each other.
  • p3 is an integer of 1 to 4, and when p3 is 2 or more, the substituents in parentheses are the same or different from each other. In an exemplary embodiment of the present application, p3 is 1. In an exemplary embodiment of the present application, p3 is 2. In an exemplary embodiment of the present application, p3 is 3. In an exemplary embodiment of the present application, p3 is 4. That is, when p3 is 2 or more, Ar13 in parentheses are the same or different from each other.
  • e is 0, 1, 2, 3, 4, 5, 6, or 7, and when e is 2 or more, R15 in parentheses are the same or different from each other.
  • f is 0, 1, 2, 3, 4, 5, 6, 7, or 8, and when f is 2 or more, R16 in parentheses are the same or different.
  • Formula 1 may be represented by any one of the following compounds, but is not limited thereto.
  • a compound having the unique properties of the introduced substituents can be synthesized.
  • substituents mainly used in hole injection materials, hole transport materials, light-emitting materials, electron transport materials, and electron injection materials used in the manufacture of organic light-emitting devices into the core structure, a material that satisfies the conditions required for each organic layer can be created. It can be synthesized.
  • the compound of Formula 1 has excellent thermal stability, and this thermal stability provides driving stability to the organic light-emitting device and improves lifespan characteristics.
  • a first electrode a second electrode provided opposite to the first electrode; And an organic light-emitting device comprising 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 includes a heterocyclic compound represented by Formula 1. provides.
  • a first electrode a second electrode provided opposite to the first electrode; and an organic light-emitting device comprising 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 includes one type of heterocyclic compound represented by Formula 1.
  • a light emitting device is provided.
  • a first electrode a second electrode provided opposite to the first electrode; And an organic light-emitting device comprising 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 includes two or more types of heterocyclic compounds represented by Formula 1.
  • An organic light emitting device is provided.
  • the heterocyclic compound represented by Formula 1 may be used as a light-emitting material for the light-emitting layer of an organic light-emitting device.
  • the heterocyclic compound represented by Formula 1 may be used as a light-emitting material for the light-emitting layer of an organic light-emitting device and may be used as an n-type host material.
  • 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 blue organic light-emitting device, and the heterocyclic compound according to Formula 1 may be used as a material for the blue 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 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 blue organic light-emitting device, and the heterocyclic compound according to Formula 1 may be used as a light-emitting layer material of the blue 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 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 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 may be formed into 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, or may 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 light emitting layer, an electron transport layer, an electron injection layer, etc. as an organic material layer.
  • the structure of the organic light emitting device is not limited to this and may include a smaller number of organic material layers.
  • Ir(ppy) 3 a green phosphorescent dopant
  • a green phosphorescent dopant may be used as the iridium-based dopant.
  • (piq) 2 (Ir) (acac), a red phosphorescent dopant may be used as the iridium-based dopant.
  • an organic light-emitting device wherein the organic material layer of the organic light-emitting device includes a light-emitting layer, and the light-emitting layer includes the heterocyclic compound.
  • an organic light-emitting device wherein the organic material layer of the organic light-emitting device includes a light-emitting layer, the light-emitting layer includes a host material, and the host material includes the heterocyclic compound.
  • 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 the heterocyclic compound.
  • 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 the heterocyclic compound.
  • 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 the heterocyclic compound.
  • anode material materials with a relatively high work function can be used as the anode material, 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 SnO 2 :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 material known hole injection materials may be used, for example, phthalocyanine compounds such as copper phthalocyanine disclosed in U.S. Patent No. 4,356,429 or described in Advanced Material, 6, p.677 (1994).
  • 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-styrenesulfonate)
  • pyrazoline derivatives As hole transport materials, 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 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 material in the industry, but the present application is not limited thereto.
  • Red, green, or blue light-emitting materials may be used as the light-emitting material, and if necessary, two or more light-emitting materials may 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 can be used as a light-emitting material, but it can also be used as a phosphorescent material. As a light-emitting material, a material that emits light by combining holes and electrons injected from an anode and a cathode, respectively, may be used, but materials that participate in light emission together with a host material and a dopant material may also be used.
  • 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 a host material for the light emitting layer.
  • the organic light emitting device may be a front emitting type, a rear emitting type, or a double-sided emitting type depending on the material used.
  • the heterocyclic compound according to an exemplary embodiment of the present application 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.
  • the organic light emitting device of the present invention 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 blocking layer, a hole blocking layer, an electron transport layer, and an electron injection layer.
  • FIG. 1 to 3 illustrate the stacking order of electrodes and organic material layers of an organic light-emitting device according to an exemplary embodiment of the present application.
  • 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.
  • an organic light-emitting device in which the organic material layer of the organic light-emitting device containing the heterocyclic compound represented by Formula 1 further includes a compound represented by Formula 2 below.
  • Ar2 and Ar3 are the same as or different from each other, and are each independently a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted heteroaryl group of C2 to C60, q and r are each integers of 1 to 4, and when q and r are each 2 or more, the substituents in parentheses are the same or different from each other,
  • L3 is a direct bond; Substituted or unsubstituted C6 to C60 arylene group; or a substituted or unsubstituted heteroarylene group of C2 to C60, o is each an integer of 0 to 3, and when o is 2 or more, the substituents in parentheses are the same or different from each other,
  • Ra and Rb are the same or different from each other and are each independently hydrogen; heavy hydrogen; Substituted or unsubstituted C1 to C20 alkyl group; and a substituted or unsubstituted C6 to C20 aryl group,
  • R, R' and R" are the same or different from each other, and are each independently hydrogen; deuterium; cyano group; substituted or unsubstituted C1 to C60 alkyl group; substituted or unsubstituted C3 to C60 cycloalkyl group; substituted or An unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group,
  • g is an integer from 0 to 5
  • h is an integer from 0 to 4
  • the substituents in parentheses are the same or different from each other.
  • Ar2 and Ar3 are the same as or different from each other, and are each independently a substituted or unsubstituted aryl group of C6 to C60; Or it may be a substituted or unsubstituted C2 to C60 heteroaryl group.
  • Ar2 and Ar3 are the same or different from each other, and are each independently a substituted or unsubstituted C6 to C40 aryl group; Or it may be a substituted or unsubstituted C2 to C40 heteroaryl group.
  • Ar2 and Ar3 are the same as or different from each other, and are each independently a substituted or unsubstituted C6 to C30 aryl group; Or it may be a substituted or unsubstituted C2 to C20 heteroaryl group.
  • Ar2 and Ar3 are the same as 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 dibenzofuran group; Substituted or unsubstituted dibenzothiophene group; Substituted or unsubstituted fluorene group; Or it may be a substituted or unsubstituted spirobifluorene group.
  • Ar2 and Ar3 are the same as 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 dibenzofuran group; Substituted or unsubstituted dibenzothiophene group; Substituted or unsubstituted dimethylfluorene group; Substituted or unsubstituted diphenylfluorene group; Or it may be a substituted or unsubstituted spirobifluorene group.
  • q in Formula 2 is an integer of 1 to 4, and when q is 2 or more, the substituents in parentheses are the same or different from each other. In an exemplary embodiment of the present application, q is 1. In an exemplary embodiment of the present application, q is 2. In an exemplary embodiment of the present application, q is 3. In an exemplary embodiment of the present application, q is 4. That is, when q is 2 or more, Ar2 in parentheses are the same or different from each other.
  • r in Formula 2 is an integer of 1 to 4, and when r is 2 or more, the substituents in parentheses are the same or different from each other. In an exemplary embodiment of the present application, r is 1. In an exemplary embodiment of the present application, r is 2. In an exemplary embodiment of the present application, r is 3. In an exemplary embodiment of the present application, r is 4. That is, when r is 2 or more, Ar3 in parentheses are the same or different from each other.
  • L3 is a direct bond; Substituted or unsubstituted C6 to C60 arylene group; Or it may be a substituted or unsubstituted C2 to C60 heteroarylene group.
  • L3 is a direct bond; Substituted or unsubstituted C6 to C40 arylene group; Or it may be a substituted or unsubstituted C2 to C40 heteroarylene group.
  • L3 is a direct bond; Substituted or unsubstituted C6 to C20 arylene group; Or it may be a substituted or unsubstituted C2 to C20 heteroarylene group.
  • L3 is a direct bond; Substituted or unsubstituted C6 to C10 arylene group; Or it may be a substituted or unsubstituted C2 to C10 heteroarylene group.
  • L3 is a direct bond; It may be a substituted or unsubstituted C6 to C10 arylene group.
  • L3 is a direct bond; Substituted or unsubstituted phenylene group; Or it may be a substituted or unsubstituted naphthylene group.
  • L3 is a direct bond; phenylene group; Or it may be a naphthylene group.
  • o is each an integer from 0 to 3, and when o is 2 or more, the substituents in parentheses are the same or different from each other. In one embodiment of the present application, o is 0. In an exemplary embodiment of the present application, o is 1. In one embodiment of the present application, o is 2. In one embodiment of the present application, o is 3. That is, when o is 2 or more, L3 in parentheses are the same or different from each other.
  • Ra and Rb are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; Substituted or unsubstituted methyl group; and a substituted or unsubstituted phenyl group.
  • Ra and Rb are the same or different from each other, and are each independently a substituted or unsubstituted C1 to C20 alkyl group; Or a substituted or unsubstituted C6 to C20 aryl group.
  • R9 and R10 are the same as or different from each other, and are each independently hydrogen; Or it may be deuterium.
  • R9 and R10 may be hydrogen.
  • R9 and R10 may be deuterium.
  • g is 0, 1, 2, 3, 4, or 5, and when g is 2 or more, R9 in parentheses are the same or different from each other.
  • h is 0, 1, 2, 3, or 4, and when each h is 2 or more, R10 in parentheses are the same or different from each other.
  • Formula 2 provides an organic light-emitting device represented by any one of the following compounds, but is not limited thereto.
  • the organic light-emitting device further containing the compound represented by Formula 2 may be applied to the organic light-emitting device containing the heterocyclic compound represented by Formula 1 described above.
  • the compound represented by Formula 2 may be used as a light-emitting material for the light-emitting layer of an organic light-emitting device.
  • the compound represented by Formula 2 may be used as a light-emitting material of the light-emitting layer of an organic light-emitting device and may be used as a p-type host material.
  • the organic material layer may include a heterocyclic compound represented by Formula 1 and a compound represented by Formula 2.
  • the organic material layer can be formed by pre-mixing the heterocyclic compound represented by Formula 1 and the compound represented by Formula 2 using a thermal vacuum deposition method.
  • the organic material layer includes a light-emitting layer, and the light-emitting layer may include a heterocyclic compound represented by Formula 1 and a compound represented by Formula 2.
  • the organic material layer includes a light emitting layer, the light emitting layer includes a host material, and the host material may include a heterocyclic compound represented by Formula 1 and a compound represented by Formula 2. .
  • the organic material layer includes a light emitting layer
  • the n-type host material of the light emitting layer includes a heterocyclic compound represented by Formula 1
  • the p-type host material includes a compound represented by Formula 2.
  • the step of forming the organic material layer is performed by supplying the heterocyclic compound represented by Formula 1 and the compound represented by Formula 2 to each individual source, and then using a thermal vacuum deposition method.
  • a method of manufacturing an organic light emitting device is provided.
  • the step of forming the organic material layer is formed by pre-mixing the heterocyclic compound represented by Formula 1 and the compound represented by Formula 2 using a thermal vacuum deposition method.
  • a method for manufacturing an organic light emitting device is provided.
  • the organic light-emitting device can be manufactured using conventional organic light-emitting device manufacturing methods and materials, except that the organic material layer is formed using the above-described compound.
  • the organic light emitting device of the present invention 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 blocking layer, an electron injection layer, an electron transport layer, a hole auxiliary layer, and a hole blocking layer. You can.
  • composition for an organic material layer of an organic light-emitting device comprising a heterocyclic compound represented by Formula 1 and a compound represented by Formula 2 is provided.
  • the weight ratio of the heterocyclic compound represented by Formula 1 to the compound represented by Formula 2 in the composition may be 1:10 to 10:1, 1:8 to 8:1, and 1:5 to 5. : 1, and 1 : 2 to 2 : 1, but is not limited thereto.
  • the composition can be used when forming an organic material layer of an organic light-emitting device, and can be particularly preferably used as a host material for the light-emitting layer.
  • the composition is a simple mixture of two or more compounds, and powdered materials may be mixed before forming the organic material layer of the organic light-emitting device, or compounds in a liquid state at an appropriate temperature or higher may be mixed.
  • the composition is in a solid state below the melting point of each material, and can be maintained in a liquid state by adjusting the temperature.
  • composition may further include materials known in the art, such as solvents and additives.
  • the water-removed reaction product was dissolved in toluene (100ml), trifluoromethanesulfonic acid (TfOH) (10ml) was added at 0°C, and stirred at 60°C for 2 hours. Afterwards, the temperature was lowered, water was added to terminate the reaction, and extraction was performed using MC (methylene chloride) and water. Afterwards, moisture was removed with MgSO 4 . Afterwards, it was separated using a silica gel column to obtain 7g of compound 413-4 with a yield of 53%.
  • TfOH trifluoromethanesulfonic acid
  • 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, it was ultrasonic washed with solvents such as acetone, methanol, and isopropyl alcohol, dried, and 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 remove the ITO work function and residual film, and then transferred to a thermal evaporation equipment for organic deposition.
  • ITO indium tinoxide
  • 2-TNATA 4,4',4''-Tris[2-naphthyl(phenyl)amino]triphenylamine
  • NPB(N,N'-Di (1-naphthyl)-N,N'-diphenyl-(1,1'-biphenyl)-4,4'-diamine) was formed.
  • a light emitting layer was thermally vacuum deposited thereon as follows.
  • the light-emitting layer was deposited with a compound listed in Table 4 as a red host, and (piq) 2 (Ir) (acac) was used as a red phosphorescent dopant, and 3 wt% of the Ir compound was doped into the host and deposited at 400 ⁇ .
  • the electroluminescence (EL) characteristics of the organic electroluminescent devices manufactured as described above were measured using M7000 from McScience, and the measurement results were used to determine T90 was measured when the standard luminance was 6,000 cd/m 2 using a lifespan measuring device (M6000).
  • M6000 lifespan measuring device
  • the results of measuring the driving voltage, luminous efficiency, color coordinate (CIE), and lifespan of the organic light-emitting device manufactured according to the present invention are shown in Table 4 below.
  • Comparative compounds H1 to H13 used in the comparative examples of Table 4 are as follows.
  • 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, it was ultrasonically cleaned with solvents such as acetone, methanol, and isopropyl alcohol, dried, and 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 remove the ITO work function and residual film, and then transferred to a thermal evaporation equipment for organic deposition.
  • ITO indium tinoxide
  • a light emitting layer was thermally vacuum deposited thereon as follows.
  • two types of compounds listed in Table 5 below were deposited from one source as a red host, and (piq) 2 (Ir) (acac) was used as a red phosphorescent dopant, and 3 wt% of the Ir compound was doped into the host to form a layer of 400 ⁇ . deposited.
  • the ratios shown in Table 5 below are the weight ratios of each compound.
  • the electroluminescence (EL) characteristics of the organic electroluminescent devices manufactured as described above were measured using M7000 from McScience, and the measurement results were used to determine T90 was measured when the standard luminance was 6,000 cd/m 2 using a lifespan measurement equipment (M6000).
  • Table 5 shows the results of measuring the driving voltage, luminous efficiency, color coordinate (CIE), and lifespan of the organic light-emitting device manufactured according to the present invention.
  • Comparative compounds H1 to H13 used in the comparative examples in Table 5 are the same as the compounds described in Table 4.

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

Abstract

La présente invention concerne un composé hétérocyclique, un élément électroluminescent organique le comprenant, et une composition pour une couche organique d'un élément électroluminescent organique.
PCT/KR2023/006795 2022-05-20 2023-05-18 Composé hétérocyclique, élément électroluminescent organique le comprenant, et composition pour couche organique d'élément électroluminescent organique WO2023224413A1 (fr)

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KR20210003041A (ko) * 2019-07-01 2021-01-11 롬엔드하스전자재료코리아유한회사 유기 전계 발광 화합물 및 이를 포함하는 유기 전계 발광 소자
KR20210089524A (ko) * 2020-01-08 2021-07-16 주식회사 엘지화학 신규한 화합물 및 이를 포함하는 유기발광 소자
KR20210155666A (ko) * 2020-06-16 2021-12-23 엘티소재주식회사 헤테로고리 화합물, 이를 포함하는 유기 발광 소자, 이의 제조 방법 및 유기물층용 조성물
KR20220023903A (ko) * 2020-08-21 2022-03-03 엘티소재주식회사 헤테로고리 화합물 및 이를 포함하는 유기 발광 소자

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KR20190120985A (ko) * 2018-04-17 2019-10-25 엘티소재주식회사 헤테로고리 화합물 및 이를 포함하는 유기 발광 소자
KR20210003041A (ko) * 2019-07-01 2021-01-11 롬엔드하스전자재료코리아유한회사 유기 전계 발광 화합물 및 이를 포함하는 유기 전계 발광 소자
KR20210089524A (ko) * 2020-01-08 2021-07-16 주식회사 엘지화학 신규한 화합물 및 이를 포함하는 유기발광 소자
KR20210155666A (ko) * 2020-06-16 2021-12-23 엘티소재주식회사 헤테로고리 화합물, 이를 포함하는 유기 발광 소자, 이의 제조 방법 및 유기물층용 조성물
KR20220023903A (ko) * 2020-08-21 2022-03-03 엘티소재주식회사 헤테로고리 화합물 및 이를 포함하는 유기 발광 소자

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