WO2023182775A1 - Novel heterocyclic compound and organic light-emitting diode including same - Google Patents

Novel heterocyclic compound and organic light-emitting diode including same Download PDF

Info

Publication number
WO2023182775A1
WO2023182775A1 PCT/KR2023/003724 KR2023003724W WO2023182775A1 WO 2023182775 A1 WO2023182775 A1 WO 2023182775A1 KR 2023003724 W KR2023003724 W KR 2023003724W WO 2023182775 A1 WO2023182775 A1 WO 2023182775A1
Authority
WO
WIPO (PCT)
Prior art keywords
group
carbon atoms
unsubstituted
substituted
structural formula
Prior art date
Application number
PCT/KR2023/003724
Other languages
French (fr)
Korean (ko)
Inventor
정재경
최호정
신봉기
Original Assignee
에스에프씨 주식회사
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by 에스에프씨 주식회사 filed Critical 에스에프씨 주식회사
Publication of WO2023182775A1 publication Critical patent/WO2023182775A1/en

Links

Images

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
    • C07D263/52—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems
    • C07D263/62—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems having two or more ring systems containing condensed 1,3-oxazole rings
    • C07D263/64—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems having two or more ring systems containing condensed 1,3-oxazole rings linked in positions 2 and 2' by chains containing six-membered aromatic rings or ring systems containing such rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
    • C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
    • C07D263/52—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems
    • C07D263/60—Naphthoxazoles; Hydrogenated naphthoxazoles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
    • C07D277/84—Naphthothiazoles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—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
    • C07D403/12—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 chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—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
    • C07D405/12—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 linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—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
    • C07D409/12—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 chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
    • C07D498/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
    • H10K50/12—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers comprising dopants
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
    • H10K85/622—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing four rings, e.g. pyrene
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
    • H10K85/623—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing five rings, e.g. pentacene
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
    • H10K85/626—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
    • H10K85/633—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
    • H10K85/636—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising heteroaromatic hydrocarbons as substituents on the nitrogen atom
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/656—Aromatic compounds comprising a hetero atom comprising two or more different heteroatoms per ring
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6574—Polycyclic condensed heteroaromatic hydrocarbons comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6576—Polycyclic condensed heteroaromatic hydrocarbons comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K2101/00—Properties of the organic materials covered by group H10K85/00
    • H10K2101/90—Multiple hosts in the emissive layer

Definitions

  • the present invention relates to a novel compound that can be used in organic light-emitting devices, and more specifically, to a novel compound that can be used as a host material for the light-emitting layer in an organic light-emitting device, through which device characteristics of low voltage, high efficiency, and long lifespan can be realized. It relates to a heterocyclic compound and an organic light-emitting device containing the same.
  • OLED Organic light emitting diode
  • organic luminescence refers to a phenomenon that converts electrical energy into light energy using organic materials.
  • Organic light-emitting devices that utilize the organic light-emitting phenomenon usually have a structure including an anode, a cathode, and an organic material layer between them.
  • the organic material layer is often composed of a multi-layer structure composed of different materials to increase the efficiency and stability of the organic light-emitting device, and may be composed of, for example, a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, and an electron injection layer.
  • this organic light-emitting device when a voltage is applied between the two electrodes, holes are injected from the anode and electrons from the cathode into the organic material layer. When the injected holes and electrons meet, an exciton is formed, and this exciton is When it falls back to the ground state, it glows.
  • These organic light-emitting devices are known to have characteristics such as self-luminescence, high brightness, high efficiency, low driving voltage, wide viewing angle, high contrast, and high-speed response.
  • Materials used as organic layers in organic light-emitting devices can be classified into light-emitting materials and charge transport materials, such as hole injection materials, hole transport materials, electron transport materials, and electron injection materials, depending on their function.
  • the light-emitting materials can be classified into high-molecular-type and low-molecular-type types depending on their molecular weight, and can be classified into fluorescent materials derived from the singlet excited state of electrons and phosphorescent materials derived from the triplet excited state of electrons depending on the light-emitting mechanism. .
  • a host-dopant system can be used as a light-emitting material to increase light-emitting efficiency through transition.
  • the principle is that when a small amount of a dopant with a smaller energy band gap than the host forming the light-emitting layer is mixed into the light-emitting layer, excitons generated in the light-emitting layer are transported to the dopant, producing highly efficient light. At this time, since the wavelength of the host moves to the wavelength of the dopant, light of the desired wavelength can be obtained depending on the type of dopant used.
  • heterocyclic compounds containing heteroatoms such as nitrogen and oxygen have recently been studied as host compounds for organic light-emitting devices using phosphorescence, and related prior art is published in Patent Publication No. 10-2023-0028739 ( 2023.03.02) presents an organic light-emitting device using carbazole-structured aromatic heterocyclic compounds as first and second host materials, respectively, and in Patent Publication No. 10-2020-0139834 (2020.12.14), polycyclic An organic light-emitting device containing a ring-structured aromatic heterocyclic compound as a phosphorescent host It is listed.
  • the first technical task to be achieved by the present invention is to provide a novel organic compound that can be used as a phosphorescent host material for the light-emitting layer in an organic light-emitting device.
  • the second technical problem to be achieved by the present invention is to provide a low-voltage, high-efficiency, and long-life organic light emitting diode (OLED) containing the organic compound as a host material in the organic light emitting device.
  • OLED organic light emitting diode
  • the present invention provides an aromatic heterocyclic compound represented by [Formula A] or [Formula B] below.
  • the X 1 is any one selected from NR 4 , O and S,
  • Z 1 to Z 8 are the same or different from each other, and are each independently selected from CR or N,
  • each R is the same as or different from each other
  • One of Z 3 to Z 6 is a carbon atom containing a single bond bonded to the linking group L,
  • R, R 1 to R 4 are the same or different from each other, and each independently represents hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, substituted or unsubstituted.
  • a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms a substituted or unsubstituted cycloalkyloxy group having 3 to 30 carbon atoms, a substituted or unsubstituted heteroaryloxy group having 2 to 30 carbon atoms, a substituted or unsubstituted Alkylthio group with 1 to 30 carbon atoms, substituted or unsubstituted arylthio group with 6 to 30 carbon atoms, substituted or unsubstituted cycloalkylthio group with 3 to 30 carbon atoms, substituted or unsubstituted heteroaryl with 2 to 30 carbon atoms Any one selected from a thio group, a substituted or unsubstituted amine group with 0 to 30 carbon atoms, a substituted or unsubstituted silyl group with 0 to 30 carbon atoms, a germanium group with 0 to 30 carbon atoms, a
  • each R adjacent to each other may be connected to each other to further form an alicyclic or aromatic monocyclic or polycyclic ring, and the formed alicyclic or aromatic ring may be
  • the carbon atom of the monocyclic or polycyclic ring may be substituted with one or more heteroatoms selected from N, S and O,
  • R 2 and R 3 may be connected to each other to further form an alicyclic or aromatic monocyclic or polycyclic ring,
  • L is a single bond, a substituted or unsubstituted arylene group having 6 to 50 carbon atoms and a substituted or unsubstituted heteroarylene group having 2 to 50 carbon atoms,
  • alkyl group cycloalkyl group with 3 to 30 carbon atoms, alkenyl group with 2 to 24 carbon atoms, alkynyl group with 2 to 24 carbon atoms, heteroalkyl group with 1 to 24 carbon atoms, aryl group with 6 to 24 carbon atoms, arylalkyl group with 7 to 24 carbon atoms , an alkylaryl group having 7 to 24 carbon atoms, a heteroaryl group having 2 to 24 carbon atoms, a heteroarylalkyl group having 2 to 24 carbon atoms, a cycloalkyl group in which an aromatic hydrocarbon ring is condensed, having 7 to 24 carbon atoms, and an aromatic group having 5 to 24 carbon atoms.
  • Cycloalkyl group with a condensed hetero ring a heterocycloalkyl group with a condensed aromatic hydrocarbon ring having 6 to 24 carbon atoms, an aryl group with a condensed aliphatic hydrocarbon ring with 8 to 24 carbon atoms, and a condensed aliphatic hydrocarbon ring with 5 to 24 carbon atoms.
  • heteroaryl group alkoxy group of 1 to 24 carbon atoms, amine group of 1 to 24 carbon atoms, silyl group of 1 to 24 carbon atoms, germanium group of 1 to 24 carbon atoms, aryloxy group of 6 to 24 carbon atoms, 6 to 24 carbon atoms means being substituted with one or more substituents selected from the group consisting of arylthionyl groups, and one or more hydrogens in each substituent can be replaced with deuterium.
  • aromatic heterocyclic compound represented by Formula A or Formula B according to the present invention When used as a phosphorescent host material for the light-emitting layer in an organic light-emitting device, it has lower voltage, higher efficiency, and longer lifespan compared to the organic light-emitting device according to the prior art.
  • An organic light emitting device that can be implemented can be provided.
  • FIG. 1 is a schematic diagram of an organic light-emitting device according to an embodiment of the present invention.
  • the present invention provides an aromatic heterocyclic compound represented by the following [Formula A] or [Formula B].
  • the X 1 is any one selected from NR 4 , O and S,
  • Z 1 to Z 8 are the same or different from each other, and are each independently selected from CR or N,
  • each R is the same as or different from each other
  • One of Z 3 to Z 6 is a carbon atom containing a single bond bonded to the linking group L,
  • R, R 1 to R 4 are the same or different from each other, and each independently represents hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, substituted or unsubstituted.
  • a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms a substituted or unsubstituted cycloalkyloxy group having 3 to 30 carbon atoms, a substituted or unsubstituted heteroaryloxy group having 2 to 30 carbon atoms, a substituted or unsubstituted Alkylthio group with 1 to 30 carbon atoms, substituted or unsubstituted arylthio group with 6 to 30 carbon atoms, substituted or unsubstituted cycloalkylthio group with 3 to 30 carbon atoms, substituted or unsubstituted heteroaryl with 2 to 30 carbon atoms Any one selected from a thio group, a substituted or unsubstituted amine group with 0 to 30 carbon atoms, a substituted or unsubstituted silyl group with 0 to 30 carbon atoms, a germanium group with 0 to 30 carbon atoms, a
  • each R adjacent to each other may be connected to each other to further form an alicyclic or aromatic monocyclic or polycyclic ring, and the formed alicyclic or aromatic ring may be
  • the carbon atom of the monocyclic or polycyclic ring may be substituted with one or more heteroatoms selected from N, S and O,
  • R 2 and R 3 may be connected to each other to further form an alicyclic or aromatic monocyclic or polycyclic ring,
  • L is a single bond, a substituted or unsubstituted arylene group having 6 to 50 carbon atoms and a substituted or unsubstituted heteroarylene group having 2 to 50 carbon atoms,
  • alkyl group cycloalkyl group with 3 to 30 carbon atoms, alkenyl group with 2 to 24 carbon atoms, alkynyl group with 2 to 24 carbon atoms, heteroalkyl group with 1 to 24 carbon atoms, aryl group with 6 to 24 carbon atoms, arylalkyl group with 7 to 24 carbon atoms , an alkylaryl group having 7 to 24 carbon atoms, a heteroaryl group having 2 to 24 carbon atoms, a heteroarylalkyl group having 2 to 24 carbon atoms, a cycloalkyl group in which an aromatic hydrocarbon ring is condensed, having 7 to 24 carbon atoms, and an aromatic group having 5 to 24 carbon atoms.
  • Cycloalkyl group with a condensed hetero ring a heterocycloalkyl group with a condensed aromatic hydrocarbon ring having 6 to 24 carbon atoms, an aryl group with a condensed aliphatic hydrocarbon ring with 8 to 24 carbon atoms, and a condensed aliphatic hydrocarbon ring with 5 to 24 carbon atoms.
  • heteroaryl group alkoxy group of 1 to 24 carbon atoms, amine group of 1 to 24 carbon atoms, silyl group of 1 to 24 carbon atoms, germanium group of 1 to 24 carbon atoms, aryloxy group of 6 to 24 carbon atoms, 6 to 24 carbon atoms means being substituted with one or more substituents selected from the group consisting of arylthionyl groups, and one or more hydrogens in each substituent can be replaced with deuterium.
  • the range of the carbon number of the alkyl group having 1 to 30 carbon atoms and the aryl group having 5 to 50 carbon atoms means the total number of carbon atoms constituting the alkyl portion or aryl portion when the substituent is regarded as unsubstituted without considering the substituted portion, respectively.
  • a phenyl group substituted with a butyl group at the para position should be viewed as corresponding to an aryl group with 6 carbon atoms substituted with a butyl group with 4 carbon atoms.
  • the aryl group which is a substituent used in the compound of the present invention, is an organic radical derived from an aromatic hydrocarbon by removal of one hydrogen. When the aryl group has a substituent, it can be fused with neighboring substituents to further form a ring. Additionally, the aryl group may include an organic radical obtained by removing one hydrogen from an arene ring formed by condensing two arene rings.
  • aryl group examples include phenyl group, o-biphenyl group, m-biphenyl group, p-biphenyl group, o-terphenyl group, m-terphenyl group, p-terphenyl group, naphthyl group, anthryl group, phenanthryl group, Aromatic radical groups such as pyrenyl group, indenyl group, fluorenyl group, tetrahydronaphthyl group, perylenyl group, chrysenyl group, naphthacenyl group, fluoranthenyl group, etc. can be mentioned, and the fluorene ring and the phenylene ring are condensed.
  • It may also include an organic radical resulting from the removal of one hydrogen in an arene ring formed by condensing two arene rings, such as an arene ring or an arene ring in which a fluorene ring and a phenanthrene ring are condensed.
  • one or more hydrogen atoms of the aryl group may be a deuterium atom, a halogen atom, a hydroxy group, a nitro group, a cyano group, a silyl group, an amino group (-NH 2 , -NH(R), -N(R')(R'' ), R' and R" are independently an alkyl group having 1 to 10 carbon atoms, in this case referred to as an "alkylamino group”), amidino group, hydrazine group, hydrazone group, carboxyl group, sulfonic acid group, phosphoric acid group, carbon number 1 to 24 alkyl group, halogenated alkyl group with 1 to 24 carbon atoms, alkenyl group with 2 to 24 carbon atoms, alkynyl group with 2 to 24 carbon atoms, heteroalkyl group with 1 to 24 carbon atoms, aryl group with 6 to 24 carbon atoms, aryl with 7 to 24 carbon carbon atom
  • the aromatic hydrocarbon ring refers to an aromatic ring made up of carbon and hydrogen
  • the aliphatic hydrocarbon ring refers to a hydrocarbon ring made up of carbon and hydrogen but does not belong to the aromatic hydrocarbon ring.
  • the aliphatic ring refers to a hydrocarbon ring made up of carbon and hydrogen.
  • the hydrocarbon ring is preferably a hydrocarbon ring in which at least 30% or more of the carbon atoms forming the ring are bonded through an sp 3 orbital structure and contain 0 to 3 double bonds and/or triple bonds in the ring. , more preferably, at least 50% or more of the carbon atoms forming the ring are bonded by sp 3 orbitals, and may be a hydrocarbon ring containing 0 to 2 double bonds and/or triple bonds in the ring.
  • the aryl group in which the aliphatic hydrocarbon ring is condensed consists of two carbon atoms adjacent to each other in the aliphatic hydrocarbon ring and two carbon atoms excluding the carbon atom that becomes an organic radical by removing the hydrogen of one of the carbon atoms forming the ring in the aryl group. It refers to a cyclic substituent in which two adjacent carbon atoms are condensed together to share one double bond and has overall non-aromaticity. Specific examples include tetrahydronaphthyl group, tetrahydrobenzocycloheptene, and tetrahydrophene. Nantrene group, tetrahydroanthracenyl group, octahydrotriphenylene group, etc. are mentioned.
  • the heteroaryl group which is a substituent used in the compound of the present invention, contains 1, 2, or 3 heteroatoms selected from N, O, P, Si, S, Ge, Se, and Te in the aromatic ring, and the remaining ring atom is carbon. It refers to an aryl group of an aromatic system with 2 to 24 rings, and the rings can be fused to form a ring. And one or more hydrogen atoms of the heteroaryl group may be replaced with the same substituent as that of the aryl group.
  • the aromatic heterocycle means that one or more aromatic carbons in the aromatic hydrocarbon ring are substituted with a hetero atom
  • the aromatic hetero ring preferably has 1 to 3 aromatic carbons in the aromatic hydrocarbon ring consisting of N, O, P, It may be substituted with one or more heteroatoms selected from Si, S, Ge, Se, and Te.
  • heteroaryl groups in which aliphatic hydrocarbon rings are condensed A substituent having a structure in which a heteroaryl group is substituted for an aryl group in the aryl group in which the aliphatic hydrocarbon ring is condensed, specific examples include tetrahydroindole group, tetrahydrobenzofuranyl group, tetrahydrobenzothiophene group, tetrahydrocarbazole group, Tetrahydrodibenzofuranyl group, tetrahydrobenzothiophene group, tetrahydroquinoline group, tetrahydroquinoxaline group, etc. are mentioned.
  • the aromatic heterocycle means that one or more aromatic carbons in the aromatic hydrocarbon ring are substituted with a hetero atom
  • the aromatic hetero ring preferably has 1 to 3 aromatic carbons in the aromatic hydrocarbon ring consisting of N, O, P, It may be substituted with one or more heteroatoms selected from Si, S, Ge, Se, and Te.
  • the 'condensed ring in which an aromatic hydrocarbon ring and an aliphatic hydrocarbon ring are condensed means a condensed ring in which two adjacent carbon atoms of an aromatic hydrocarbon ring and two adjacent carbon atoms of an aliphatic hydrocarbon ring are shared.
  • Examples include a tetrahydronaphthalene ring in which two carbon atoms adjacent to each other in a benzene ring and a cyclohexane ring are shared and condensed.
  • the 'condensed ring in which an aromatic heterocycle and an aliphatic hydrocarbon ring are condensed' is a condensed ring in which two adjacent carbon atoms of an aromatic heterocycle and two adjacent carbon atoms of an aliphatic hydrocarbon ring are shared. It means, and an example is a hexahydrodibenzofuran ring in which two adjacent carbon atoms in each ring of a benzofuran ring and a cyclohexane ring are shared and condensed.
  • the alkyl group which is a substituent used in the present invention, is a substituent in which one hydrogen is removed from an alkane, and has a straight-chain and branched structure, and specific examples thereof include methyl, ethyl, propyl, isopropyl, isobutyl, and sec. -butyl, tert-butyl, pentyl, iso-amyl, hexyl, etc., and one or more hydrogen atoms of the alkyl group may be replaced with the same substituent as that of the aryl group.
  • 'Cyclo' in the cycloalkyl group, cycloalkoxy group, etc. which are substituents used in the compound of the present invention, refers to a substituent with a structure capable of forming a single ring or multiple rings of a saturated hydrocarbon in an alkyl or alkoxy group, for example, the specific substituent of the cycloalkyl group.
  • Examples include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, methylcyclopentyl, methylcyclohexyl, ethylcyclopentyl, ethylcyclohexyl, adamantyl, dicyclopentadienyl, decahydronaphthyl, norbornyl, bornyl, Isobornyl, etc. may be mentioned, and one or more hydrogen atoms of the cycloalkyl group may be replaced by the same substituent as that of the aryl group, and this may also be applied to cycloalkoxy.
  • the heterocycloalkyl group means that at least one carbon in the ring of the substituent forming the cycloalkyl structure is substituted with a hetero atom, preferably, 1 to 3 carbons are N, O, P, S, It may be substituted with one or more heteroatoms selected from Si, Ge, Se, and Te.
  • the cycloalkyl group in which the aromatic hydrocarbon ring or aromatic hetero ring is condensed contains two carbon atoms adjacent to each other in the aromatic hydrocarbon ring or aromatic hetero ring; and an organic radical by removal of hydrogen from one of the carbon atoms forming the ring in the cycloalkyl group.
  • the heterocycloalkyl group in which the aromatic hydrocarbon ring is condensed means that one or more carbon atoms in the cycloalkyl ring in the cycloalkyl group in which the aromatic hydrocarbon ring is condensed are substituted with a hetero atom, and preferably 1 to 1 in the cycloalkyl ring. It is a substituent in which three carbons are substituted with one or more heteroatoms selected from N, O, P, S, Si, Ge, Se, and Te. Specific examples include hexahydrodibenzofuranyl group, hexahydrocarbazole group, and hexahydrodi. Benzothiophene group, dihydrobenzodioxine group, etc. are included, and overall, it shows non-aromaticity.
  • an aryl group or heteroaryl group in which an aliphatic heterocycle is condensed A substituent having a structure in which an aliphatic heterocycle is condensed instead of an aliphatic hydrocarbon ring in the aryl group or heteroaryl group in which the aliphatic hydrocarbon ring is condensed.
  • Specific examples include chroman group, dihydropyranopyridine group, thiochroman group, and dihydrobenzodioxin. group, dihydrothiopyranopyridine group, dihydropyranopyrimidine group, etc., and shows non-aromaticity overall.
  • the aliphatic heterocycle means that at least one carbon in the aliphatic hydrocarbon ring is substituted with a hetero atom, and the aliphatic heterocycle preferably has 1 to 3 carbon atoms in the aliphatic hydrocarbon ring at least one hetero atom selected from N, O, or S. It can be replaced with an atom.
  • the alkoxy group which is a substituent used in the compound of the present invention, is a substituent in which an oxygen atom is bonded to the end of an alkyl group or cycloalkyl group, and specific examples thereof include methoxy, ethoxy, propoxy, isobutyloxy, sec-butyloxy, pentyloxy, and iso.
  • at least one hydrogen atom of the alkoxy group is the aryl group. It can be substituted with the same substituent as in the case of.
  • One or more hydrogen atoms in the aryl group may be replaced with the same substituent as in the case of the aryl group.
  • silyl group as a substituent used in the compound of the present invention examples include trimethylsilyl, triethylsilyl, triphenylsilyl, trimethoxysilyl, dimethoxyphenylsilyl, diphenylmethylsilyl, diphenylvinylsilyl, and methylcyclobutylsilyl. , dimethylfurylsilyl, etc., and one or more hydrogen atoms of the silyl group may be replaced with the same substituent as that of the aryl group.
  • an alkenyl group refers to an alkyl substituent containing one carbon-carbon double bond made up of two carbon atoms
  • an alkynyl group means one made up of two carbon atoms. It refers to an alkyl substituent containing a carbon-carbon triple bond.
  • the alkylene group used in the present invention is an organic radical derived by removing two hydrogens in an alkane molecule, which is a straight-chain or branched saturated hydrocarbon.
  • the alkylene group include methylene group. , ethylene group, propylene group, isopropylene group, isobutylene group, sec-butylene group, tert-butylene group, pentylene group, iso-amylene group, hexylene group, etc., and hydrogen at least one of the alkylene groups Atoms can be substituted with the same substituents as in the case of the aryl group above.
  • diarylamino group refers to an amine group in which two identical or different aryl groups described above are bonded to a nitrogen atom
  • diheteroarylamino group in the present invention refers to an amine group in which two identical or different heteroaryl groups are bonded to a nitrogen atom
  • the aryl (heteroaryl) amino group refers to an amine group in which the aryl group and the heteroaryl group are each bonded to a nitrogen atom.
  • this is deuterium, cyano group, halogen group, hydroxy group, nitro group, carbon number 1 to 12 alkyl group, halogenated alkyl group with 1 to 12 carbon atoms, alkenyl group with 2 to 12 carbon atoms, alkynyl group with 2 to 12 carbon atoms, cycloalkyl group with 3 to 12 carbon atoms, heteroalkyl group with 1 to 12 carbon atoms, aryl with 6 to 18 carbon atoms group, arylalkyl group with 7 to 20 carbon atoms, alkylaryl group with 7 to 20 carbon atoms, heteroaryl group with 2 to 18 carbon atoms, heteroarylalkyl group with 3 to 18 carbon atoms, alkylheteroaryl group with 3 to 18 carbon atoms, 9 to 9 carbon atoms
  • Aryl group in which a hydrocarbon ring is condensed a heteroaryl group in which an aliphatic hydrocarbon ring having 7 to 20 carbon atoms is condensed,
  • An alkoxy group with 1 to 12 carbon atoms an amine group with 1 to 18 carbon atoms, a silyl group with 1 to 18 carbon atoms, a germanium group with 1 to 18 carbon atoms, an aryloxy group with 6 to 18 carbon atoms, and an arylthionyl group with 6 to 18 carbon atoms. It may be substituted with one or more substituents selected from the group consisting of, and one or more hydrogens in each substituent may be replaced with deuterium.
  • the cycloalkyl group in which a substituted or unsubstituted aromatic hydrocarbon ring having 7 to 30 carbon atoms is condensed it is a cycloalkyl group in which a substituted or unsubstituted aromatic hydrocarbon ring having 9 to 20 carbon atoms is condensed. It may be a cycloalkyl group.
  • the cycloalkyl group in which a substituted or unsubstituted aromatic heterocycle having 5 to 30 carbon atoms is condensed it is a cycloalkyl group in which a substituted or unsubstituted aromatic heteroring having 7 to 20 carbon atoms is condensed. It may be a cycloalkyl group.
  • the substituted or unsubstituted carbon number is 6
  • a heterocycloalkyl group in which a 30 to 30 aromatic hydrocarbon ring is condensed it may be a substituted or unsubstituted heterocycloalkyl group in which a 9 to 20 carbon atom aromatic hydrocarbon ring is condensed.
  • the aryl group in which a substituted or unsubstituted aliphatic hydrocarbon ring having 8 to 30 carbon atoms is condensed it is an aryl group in which a substituted or unsubstituted aliphatic hydrocarbon ring having 9 to 20 carbon atoms is condensed. It may be an aryl group.
  • the heteroaryl group in which the substituted or unsubstituted aliphatic hydrocarbon ring having 5 to 30 carbon atoms is condensed it is a substituted or unsubstituted heteroaryl group having 7 to 20 carbon atoms in which the aliphatic hydrocarbon ring is condensed. It may be a heteroaryl group.
  • an aryl group in which a substituted or unsubstituted aliphatic heterocycle having 6 to 30 carbon atoms is condensed it is an aryl group in which a substituted or unsubstituted aliphatic heteroring having 7 to 20 carbon atoms is condensed. It may be an aryl group.
  • heteroaryl group in which a substituted or unsubstituted aliphatic heterocycle having 5 to 30 carbon atoms is condensed it is a group in which a substituted or unsubstituted aliphatic heteroring having 6 to 20 carbon atoms is condensed. It may be a heteroaryl group.
  • 'R 2 and R 3 may be connected to each other to additionally form an alicyclic or aromatic single or polycyclic ring', this means that one hydrogen radical from each of R 2 and R 3 This means that an additional ring can be formed by removing and connecting them.
  • the aromatic heterocyclic compound represented by [Formula A] or [Formula B] is an aromatic heterocyclic compound containing X 1 and a nitrogen atom (N) in a phenanthrene-like ring containing Z 1 to Z 8 It has a parent core structure in which a pentagonal ring is condensed, and a substituent R 1 is bonded to the aromatic carbon atom bonded to One of Z 3 to Z 6 is an amine substituent ( ) has a technical characteristic of being a carbon atom containing a single bond bonded to the linking group L.
  • X 1 in Formula A and Formula B may be O or S.
  • R 1 to R 4 in Formula A and Formula B are preferably the same as or different from each other, and are each independently hydrogen, deuterium, or a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms. , a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 20 carbon atoms.
  • At least one of R 1 to R 3 in Formula A and Formula B may be an aryl group having 6 to 24 carbon atoms, and more preferably, at least one of R 1 to R 3 is It may be any one selected from Structural Formulas 1 to 6 below.
  • Z is any one selected from NR 5 , CR 6 R 7 , O and S,
  • R 5 to R 7 are the same as R 1 to R 4 ,
  • the carbon site of the aromatic ring may be bonded to one or more selected from hydrogen, deuterium, an alkyl group having 1 to 10 carbon atoms, and an aryl group having 6 to 18 carbon atoms.
  • At least one of R 1 to R 3 in the aromatic heterocyclic compound may be a substituent represented by [Structural Formula A] below.
  • Q is any one ring selected from the structural formulas Q-1 to Q-3 below,
  • a pair of substituents among the neighboring carbon atoms R 17 and R 18 , R 18 and R 19 , and R 19 and R 20 in structural formula Q-1 are aromatic carbon atoms in structural formula A. It is a single bond that is condensed with f and the aromatic carbon atom g to form a 6-membered ring,
  • substituents R 11 to R 16 and R 17 to R 44 are the same or different from each other, and each independently represents hydrogen, deuterium, deuterium, substituted or unsubstituted carbon atoms of 1 to 24.
  • Alkyl group deuterated or unsubstituted halogenated alkyl group having 1 to 24 carbon atoms, deuterated or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, deuterated or unsubstituted alkenyl group having 2 to 24 carbon atoms, deuterium substituted or unsubstituted Alkynyl group having 2 to 24 carbon atoms, deuterated or unsubstituted heteroalkyl group having 1 to 24 carbon atoms, deuterated or unsubstituted aryl group having 6 to 24 carbon atoms, deuterium substituted or unsubstituted arylalkyl group having 7 to 24 carbon atoms , deuterium substituted or unsubstituted alkylaryl group having 7 to 24 carbon atoms, deuterium substituted or unsubstituted heteroaryl group having 2 to 24 carbon atoms, deuterium substituted or unsubstituted heteroarylalkyl group
  • Aryl group deuterium-substituted or unsubstituted alkoxy group of 1 to 24 carbon atoms, deuterium-substituted or unsubstituted amine group of 1 to 24 carbon atoms, deuterium-substituted or unsubstituted silyl group of 1 to 24 carbon atoms, deuterium-substituted or unsubstituted Any one selected from the group consisting of a germanium group having 1 to 24 carbon atoms, a deuterium-substituted or unsubstituted aryloxy group having 6 to 24 carbon atoms, and a deuterium-substituted or unsubstituted arylthionyl group having 6 to 24 carbon atoms,
  • R 11 to R 16 in the structural formula A When Q in the structural formula A is structural formula Q-2, one of R 11 to R 16 in the structural formula A, or Within structural formula Q-2 One of R 25 to R 34 is a single bond bonded to the carbon atom or nitrogen atom bonded to R 1 to R 3 ,
  • R 11 to R 16 in the structural formula A When Q in the structural formula A is structural formula Q-3, one of R 11 to R 16 in the structural formula A, or Within structural formula Q-3 One of R 35 to R 42 is a single bond bonded to the carbon atom or nitrogen atom bonded to R 1 to R 3 ,
  • R 43 and R 44 may be connected to each other to further form an alicyclic or aromatic monocyclic or polycyclic ring.
  • the substituent represented by [Structural Formula A] may be any one of the substituents selected from the following [Structural Formula A-1] to [Structural Formula A-15].
  • At least one of R 1 to R 3 in [Formula A] and [Formula B] may be a substituent represented by [Structural Formula A], and more preferably, only R 2 It may be a substituent represented by [structural formula A], or only R 3 may be a substituent represented by [structural formula A].
  • the substituent R 1 in Formula A and Formula B may be any one selected from a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, and a substituted or unsubstituted phenanthryl group. there is.
  • aromatic heterocyclic compound represented by [Formula A] or [Formula B] of the present invention it may be any one compound selected from ⁇ 1> to ⁇ 240> below, but is not limited thereto. No.
  • the present invention includes a first electrode; a second electrode opposite the first electrode; and an organic layer interposed between the first electrode and the second electrode, wherein the organic layer includes one or more compounds represented by [Formula A] or [Formula B] according to the present invention.
  • the organic light emitting device according to the present invention can exhibit low voltage driving, high efficiency, and long life characteristics.
  • the organic layer includes one or more organic compounds
  • the organic layer in the organic light emitting device of the present invention may include at least one of a hole injection layer, a hole transport layer, a functional layer having both a hole injection function and a hole transport function, a light emitting layer, an electron transport layer, and an electron injection layer, At least one of the organic layers may include one or more aromatic heterocyclic compounds represented by [Formula A] or [Formula B].
  • the present invention includes a first electrode; a second electrode opposite the first electrode; and an organic layer interposed between the first electrode and the second electrode, wherein the organic layer includes: a light emitting layer; And, at least one layer of a hole injection layer, a hole transport layer, a functional layer having both a hole injection function and a hole transport function, an electron blocking layer, a hole blocking layer, an electron transport layer, and an electron injection layer; and the light emitting layer is a host. and a dopant, and the host provides an organic light-emitting device including one or more of the aromatic heterocyclic compounds according to the present invention.
  • a dopant material may be used in the light emitting layer in addition to a host.
  • the content of the dopant can typically be selected in the range of about 0.01 to about 20 parts by weight based on about 100 parts by weight of the host, but is not limited thereto.
  • the dopant is not a fluorescent dopant material that only transitions to a singlet state using the Forster energy transfer method in the existing host-dopant system, but a singlet dopant material.
  • Ir, Pt, Os, Ti, Zr, Hf, Eu, Tb, Tm, Fe, Co, Ni, Ru, Rh, Re using the Dexter Energy transfer method that transfers without distinguishing between and triplet states.
  • It includes a phosphorescent dopant material of a metal complex containing one or more metals selected from Pd, etc., and known dopant materials can be used without particular restrictions as long as they emit light from triplet excitons.
  • Ir, Pt, Pd, etc. can be selected as the metal complex, and specific examples include Ir(ppy) 3 , Ir(ppy) 2 acac, Ir(Bt) 2 acac, Ir(MDQ) 2 acac, Ir( mppy) 3 , Ir(piq) 3, Ir (piq) 2 acac, Ir (pq) 2 acac, Ir(mpp) 2 acac, F 2 Irpic, (F 2 ppy) 2 Ir(tmd), Ir(ppy) 2 tmd, Ir(pmi) 3 , Ir(pmb) 3 , FCNIr, FCNIrpic, FIr6, FIrN4, FIrpic, PtOEP, Ir(chpy) 3 ,P0-01(C 31 H 23 IrN 2 O 2 S 2 ), Ir (ppz) 3, Ir(dfppz) 3, PtNON, Pt-10,
  • PtOEP Ir(Bt) 2 acac, Ir(MDQ) 2 acac, Ir(piq) 3 , Ir(piq) 2 acac, Ir(pq) 2 acac used as a red phosphorescent dopant. etc. may be used, but are not limited thereto.
  • the organic layer interposed between the first electrode and the second electrode includes a light-emitting layer, and the host in the light-emitting layer is represented by [Formula A] or [Formula B].
  • the host in the light-emitting layer is represented by [Formula A] or [Formula B].
  • one or more additional host compounds may be included, and two or more types of host compounds may be mixed or stacked.
  • one or more additional host compounds are additionally included, and when two or more host compounds are used mixed or stacked, more preferably As the additional host, a compound having an electron accepting moiety may be used, Due to the high hole injection caused by mixing or stacking with [Formula A] or [Formula B] having an amine group, which is an electron donor moiety, and the HOMO/LUMO level of the electron injection barrier, the recombination area is limited to the interface of the two hosts, thereby reducing current loss. Due to the advantages of minimizing high efficiency and long lifespan, organic light emitting devices can be implemented.
  • compounds having the electron accepting moiety receive electrons from the outside, such as azine compounds, which are nitrogen-containing aromatic heterocycles such as pyridine, pyrimidine, and triazine, and compounds substituted with a cyano group (-CN) in the molecule.
  • a compound having a moiety that has an environment that is easy to receive Preferably a heteroaryl group containing 1 to 3 N (nitrogen) elements in the molecule; Alternatively, it may include a compound containing an aryl group containing 1 to 3 cyano groups (-CN) in the molecule.
  • the light emitting layer may further include various hosts and various dopant materials in addition to the dopant and host.
  • FIG. 1 is a diagram showing the structure of an organic light-emitting device according to an embodiment of the present invention.
  • the organic light emitting device includes an anode 20, a hole transport layer 40, a light emitting layer 50 including a host and a dopant, an electron transport layer 60, and a cathode ( 80) in sequential order, wherein the anode is a first electrode, the cathode is a second electrode, a hole transport layer is provided between the anode and the light-emitting layer, and an electron transport layer is provided between the light-emitting layer and the cathode. Applies to organic light emitting devices.
  • the organic light emitting device includes a hole injection layer 30 between the anode 20 and the hole transport layer 40, and an electron transport layer 60 and the cathode 80.
  • An injection layer 70 may be included.
  • the organic light-emitting device of the present invention and its manufacturing method will be described with reference to FIG. 1 as follows.
  • the positive electrode (anode) material is coated on the upper part of the substrate 10 to form the positive electrode 20.
  • the substrate 10 a substrate used in a typical organic EL device is used, and an organic substrate or a transparent plastic substrate having excellent transparency, surface smoothness, ease of handling, and waterproofness is preferable.
  • the hole injection layer 30 is formed by vacuum thermal deposition or spin coating of a hole injection layer material on the upper electrode of the anode 20.
  • a hole transport layer 40 is formed on the top of the hole injection layer 30 by vacuum thermal evaporation or spin coating of a hole transport layer material.
  • the hole injection layer material can be used without particular restrictions as long as it is commonly used in the industry, for example, 2-TNATA [4,4',4"-tris(2-naphthylphenyl-phenylamino)-triphenylamine] , NPD[N,N'-di(1-naphthyl)-N,N'-diphenylbenzidine)], TPD[N,N'-diphenyl-N,N'-bis(3-methylphenyl)-1,1'- biphenyl-4,4'-diamine], DNTPD[N,N'-diphenyl-N,N'-bis-[4-(phenyl-m-tolyl-amino)-phenyl]-biphenyl-4,4'-diamine ] can be used, etc.
  • 2-TNATA 4,4',4"-tris(2-naphthylphenyl-phenylamino)-triphenylamine]
  • NPD
  • the material of the hole transport layer is not particularly limited as long as it is commonly used in the art, for example, N,N'-bis(3-methylphenyl)-N,N'-diphenyl -[1,1- Biphenyl]-4,4'-diamine (TPD) or N,N'-di(naphthalen-1-yl)-N,N'-diphenylbenzidine (a-NPD) can be used.
  • TPD N,N'-bis(3-methylphenyl)-N,N'-diphenyl -[1,1- Biphenyl]-4,4'-diamine
  • a-NPD N,N'-di(naphthalen-1-yl)-N,N'-diphenylbenzidine
  • the present invention is not necessarily limited thereto.
  • an electron blocking layer may be additionally formed on the hole transport layer.
  • the electron blocking layer is a layer to improve the lifespan and efficiency of the device by preventing electrons injected from the electron injection layer from passing through the light-emitting layer and entering the hole transport layer, and can be formed in an appropriate portion between the light-emitting layer and the hole injection layer. and may preferably be formed between the light emitting layer and the hole transport layer.
  • the light emitting layer 50 may be laminated on the hole transport layer 40 or the electron blocking layer using a vacuum deposition method or a spin coating method.
  • the light-emitting layer may be composed of a host and a dopant, and the materials constituting them are as described above.
  • the thickness of the light-emitting layer is preferably 50 to 2,000 ⁇ .
  • a thin film of a hole blocking layer (not shown) can be selectively formed on the organic light emitting layer 50 using a vacuum deposition method or a spin coating method.
  • the hole blocking layer serves to prevent this problem by using a material with a very low HOMO (Highest Occupied Molecular Orbital) level because the lifespan and efficiency of the device are reduced when holes pass through the light emitting layer and flow into the cathode.
  • the hole blocking material used is not particularly limited, but must have electron transport ability and a higher ionization potential than the light-emitting compound.
  • Materials used in the hole blocking layer include BAlq, BCP, Bphen, TPBI, NTAZ, BeBq 2 , OXD-7, Liq and any one selected from Formulas 1001 to 1007 may be used, but are not limited thereto.
  • the electron transport layer 60 is deposited on the light emitting layer or the hole blocking layer through a vacuum deposition method or a spin coating method.
  • a known electron transport material that functions to stably transport electrons injected from an electron injection electrode (cathode) can be used.
  • known electron transport materials include quinoline derivatives, especially tris(8-quinolinolate) aluminum (Alq 3 ), Liq, TAZ, BAlq, beryllium bis(benzoquinolin-10-noate) Materials such as -10-olate: Bebq2), Compound 201, Compound 202, BCP, and oxadiazole derivatives such as PBD, BMD, and BND may be used, but are not limited thereto.
  • an electron injection layer which is a material that has the function of facilitating injection of electrons from the cathode, can be laminated on the top of the electron transport layer. This is a special material. No restrictions.
  • any material known as an electron injection layer forming material such as CsF, NaF, LiF, Li 2 O, BaO, etc. can be used.
  • the deposition conditions for the electron injection layer vary depending on the compound used, but can generally be selected from a range of conditions that are substantially the same as those for forming the hole injection layer.
  • the thickness of the electron injection layer may be about 1 ⁇ to about 100 ⁇ , or about 3 ⁇ to about 90 ⁇ . When the thickness of the electron injection layer satisfies the range described above, satisfactory electron injection characteristics can be obtained without a substantial increase in driving voltage.
  • the cathode may be made of a material with a low work function to facilitate electron injection.
  • Lithium (Li), magnesium (Mg), calcium (Ca), or their alloys aluminum (Al), aluminum-lithium (Al-Li), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag) etc., or a transmission type cathode using ITO or IZO can be used.
  • the organic light-emitting device of the present invention may additionally include a light-emitting layer of a blue light-emitting material, a green light-emitting material, or a red light-emitting material that emits light in a wavelength range of 380 nm to 800 nm. That is, the light-emitting layer in the present invention is a plurality of light-emitting layers, and the blue light-emitting material, green light-emitting material, or red light-emitting material in the additionally formed light-emitting layer may be a fluorescent material or a phosphorescent material.
  • one or more layers selected from among the above layers may be formed by a single molecule deposition process or a solution process.
  • the deposition process refers to a method of forming a thin film by evaporating the material used as a material for forming each layer through heating in a vacuum or low pressure state, and the solution process is used to form each layer.
  • This refers to a method of mixing a substance used as a material with a solvent and forming a thin film through methods such as inkjet printing, roll-to-roll coating, screen printing, spray coating, dip coating, and spin coating.
  • the organic light emitting device in the present invention may include a flat panel display device; flexible display device; Devices for monochromatic or white flat panel lighting; and devices for single-color or white flexible lighting; Vehicle display devices; and a display device for virtual or augmented reality.
  • ⁇ B-2> was synthesized in the same manner except that ⁇ B-1> was used instead of ⁇ A-2> used in Synthesis Example 1-3, and ⁇ B-2a> was used instead of ⁇ A-3a>. got it (yield 68.2%)
  • ⁇ C-1a> 100 g of ⁇ C-1a>, 8.4 g of iodine, and 500 mL of pyridine were added to the nitrogen-purged reactor.
  • ⁇ A-1b> 57.9 mL was added dropwise, and the temperature was raised to 80°C. After 3 hours, it was cooled to room temperature, and then saturated sodium thiosulfate aqueous solution and ethyl acetate were added to separate the layers. After concentrating the organic layer under reduced pressure, toluene was added and heated to dissolve, filtered using silica gel, concentrated under reduced pressure, and recrystallized to obtain ⁇ C-1>. (128 g, 95.1%)
  • ⁇ G-1> was obtained by synthesis in the same manner, except that ⁇ G-1a> was used instead of ⁇ A-2> used in Synthesis Example 1-3. (yield 95.2%)
  • ⁇ G-4> was synthesized in the same manner except that ⁇ G-3> was used instead of ⁇ A-4> used in Synthesis Example 1-5, and ⁇ G-4a> was used instead of ⁇ A-5a>. got it (yield 65.2%)
  • ⁇ G-7> was obtained by synthesis in the same manner, except that ⁇ G-6> was used instead of ⁇ A-3> used in Synthesis Example 1-4. (yield 30.5%)
  • the ITO glass was patterned so that the light emitting area was 2 mm ⁇ 2 mm in size and then cleaned. After mounting the ITO glass in a vacuum chamber, the base pressure is set to 1 ⁇ 10 -6 torr, and then HATCN (50 ⁇ ) and NPD (1500 ⁇ ) are formed on the ITO in that order.
  • the organic light emitting device for the comparative example was manufactured in the same manner as the device structure of the above example, except for the following [RH-1] and [RH-2] instead of the compound according to the present invention as the host compound.
  • the emission characteristics of the organic light emitting device were measured at 0.4 mA.
  • the structures of [RH-1] and [RH-2] are as follows.
  • the organic light-emitting compound according to the present invention appears to have better low-voltage driving, high efficiency, and long life characteristics compared to Comparative Examples 1 and 2 according to the prior art. It shows high applicability as a light-emitting device.
  • the aromatic heterocyclic compound represented by [Formula A] or [Formula A] according to the present invention When used as a phosphorescent host material for a light-emitting layer in an organic light-emitting device, it operates at a lower voltage and has higher efficiency than the organic light-emitting device according to the prior art. and long lifespan, it has high industrial applicability in industrial fields such as organic light-emitting devices and displays.

Abstract

The present invention pertains to: a novel aromatic heterocyclic compound that can be used in an organic light-emitting diode; and an organic light-emitting diode including same.

Description

신규한 헤테로고리 화합물 및 이를 포함하는 유기발광소자Novel heterocyclic compounds and organic light-emitting devices containing them
본 발명은 유기 발광 소자에 사용될 수 있는 신규한 화합물에 관한 것으로서, 보다 상세하게는, 유기 발광 소자내 발광층의 호스트 재료로 사용될 수 있으며, 이를 통해 저전압, 고효율 및 장수명의 소자 특성을 구현할 수 있는 신규한 헤테로고리 화합물 및 이를 포함하는 유기 발광 소자에 관한 것이다. The present invention relates to a novel compound that can be used in organic light-emitting devices, and more specifically, to a novel compound that can be used as a host material for the light-emitting layer in an organic light-emitting device, through which device characteristics of low voltage, high efficiency, and long lifespan can be realized. It relates to a heterocyclic compound and an organic light-emitting device containing the same.
유기 발광 소자(organic light emitting diode, OLED)는 자기 발광 현상을 이용한 디스플레이로서, 시야각이 크고 액정 디스플레이에 비해 경박, 단소해질 수 있고, 빠른 응답 속도 등의 장점을 가지고 있어 풀-컬러(full-color) 디스플레이 또는 조명으로의 응용이 기대되고 있다.Organic light emitting diode (OLED) is a display that uses the self-luminescence phenomenon, and has advantages such as a large viewing angle, being lightweight and compact compared to liquid crystal displays, and fast response speed, so it is full-color. ) Application to displays or lighting is expected.
일반적으로 유기 발광 현상이란 유기 물질을 이용하여 전기에너지를 빛에너지로 전환시켜주는 현상을 말한다. 유기 발광 현상을 이용하는 유기 발광 소자는 통상 양극과 음극 및 이 사이에 유기물층을 포함하는 구조를 가진다. 여기서 유기물층은 유기 발광 소자의 효율과 안정성을 높이기 위하여 각기 다른 물질로 구성된 다층의 구조로 이루어진 경우가 많으며, 예컨대 정공주입층, 정공수송층, 발광층, 전자수송층, 전자주입층 등으로 이루어질 수 있다. 이러한 유기 발광 소자의 구조에서 두 전극 사이에 전압을 걸어주게 되면 양극에서는 정공이, 음극에서는 전자가 유기물층에 주입되게 되고, 주입된 정공과 전자가 만났을 때 엑시톤(exciton)이 형성되며, 이 엑시톤이 다시 바닥상태로 떨어질 때 빛이 나게 된다. 이러한 유기 발광 소자는 자발광, 고휘도, 고효율, 낮은 구동전압, 넓은 시야각, 높은 콘트라스트, 고속 응답성 등의 특성을 갖는 것으로 알려져 있다.In general, organic luminescence refers to a phenomenon that converts electrical energy into light energy using organic materials. Organic light-emitting devices that utilize the organic light-emitting phenomenon usually have a structure including an anode, a cathode, and an organic material layer between them. Here, the organic material layer is often composed of a multi-layer structure composed of different materials to increase the efficiency and stability of the organic light-emitting device, and may be composed of, for example, a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, and an electron injection layer. In the structure of this organic light-emitting device, when a voltage is applied between the two electrodes, holes are injected from the anode and electrons from the cathode into the organic material layer. When the injected holes and electrons meet, an exciton is formed, and this exciton is When it falls back to the ground state, it glows. These organic light-emitting devices are known to have characteristics such as self-luminescence, high brightness, high efficiency, low driving voltage, wide viewing angle, high contrast, and high-speed response.
유기 발광 소자에서 유기물층으로 사용되는 재료는 기능에 따라, 발광 재료와 전하수송 재료, 예컨대 정공주입 재료, 정공수송 재료, 전자수송 재료, 전자주입 재료 등으로 분류될 수 있다. 상기 발광 재료는 분자량에 따라 고분자형과 저분자형으로 분류될 수 있고, 발광 메커니즘에 따라 전자의 일중항 여기상태로부터 유래되는 형광 재료와 전자의 삼중항 여기상태로부터 유래되는 인광 재료로 분류될 수 있다. Materials used as organic layers in organic light-emitting devices can be classified into light-emitting materials and charge transport materials, such as hole injection materials, hole transport materials, electron transport materials, and electron injection materials, depending on their function. The light-emitting materials can be classified into high-molecular-type and low-molecular-type types depending on their molecular weight, and can be classified into fluorescent materials derived from the singlet excited state of electrons and phosphorescent materials derived from the triplet excited state of electrons depending on the light-emitting mechanism. .
한편, 발광 재료로서 하나의 물질만 사용하는 경우, 분자간 상호 작용에 의하여 최대 발광 파장이 장파장으로 이동하고 색순도가 떨어지거나 발광 감쇄 효과로 소자의 효율이 감소되는 문제가 발생하므로, 색순도의 증가와 에너지 전이를 통한 발광 효율을 증가시키기 위하여 발광 재료로서 호스트-도판트 시스템을 사용할 수 있다.On the other hand, when only one substance is used as a light-emitting material, the maximum emission wavelength moves to a longer wavelength due to intermolecular interactions, and problems arise such as color purity being reduced or the efficiency of the device being reduced due to the emission attenuation effect. Therefore, color purity is increased and energy is reduced. A host-dopant system can be used as a light-emitting material to increase light-emitting efficiency through transition.
그 원리는 발광층을 형성하는 호스트보다 에너지 대역 간극이 작은 도판트를 발광층에 소량 혼합하면, 발광층에서 발생한 엑시톤이 도판트로 수송되어 효율이 높은 빛을 내는 것이다. 이때, 호스트의 파장이 도판트의 파장대로 이동하므로, 이용하는 도판트의 종류에 따라 원하는 파장의 빛을 얻을 수 있다.The principle is that when a small amount of a dopant with a smaller energy band gap than the host forming the light-emitting layer is mixed into the light-emitting layer, excitons generated in the light-emitting layer are transported to the dopant, producing highly efficient light. At this time, since the wavelength of the host moves to the wavelength of the dopant, light of the desired wavelength can be obtained depending on the type of dopant used.
이러한 발광층 중 인광을 이용한 유기발광소자용 호스트 화합물로서 최근 질소, 산소 등의 헤테로원자를 함유하는 헤테로고리 화합물에 대해 연구가 되고 있으며, 이와 관련된 종래기술로서 공개특허공보 제10-2023-0028739호(2023.03.02)에는 카바졸 구조의 방향족 헤테로고리 화합물을 각각 제1 호스트 및 제2 호스트 물질로 사용한 유기발광소자가 제시되어 있고, 공개특허 공보 제10-2020-0139834호(2020.12.14)에서는 다환고리 구조의 방향족 헤테로고리 화합물을 인광 호스트로 포함하는 유기발광소자가 기재되어 있다.Among these light-emitting layers, heterocyclic compounds containing heteroatoms such as nitrogen and oxygen have recently been studied as host compounds for organic light-emitting devices using phosphorescence, and related prior art is published in Patent Publication No. 10-2023-0028739 ( 2023.03.02) presents an organic light-emitting device using carbazole-structured aromatic heterocyclic compounds as first and second host materials, respectively, and in Patent Publication No. 10-2020-0139834 (2020.12.14), polycyclic An organic light-emitting device containing a ring-structured aromatic heterocyclic compound as a phosphorescent host It is listed.
그러나, 상기 종래기술을 포함하여 유기발광소자의 발광층에 사용하기 위한 다양한 형태의 화합물이 제조되었음에도 불구하고, 아직까지 유기 발광 소자용으로 응용가능하면서, 저전압 구동, 고효율 및 장수명의 소자 특성을 가지는 신규한 화합물 및 이를 포함하는 유기발광소자의 개발의 필요성은 지속적으로 요구되고 있는 실정이다.However, despite the fact that various types of compounds have been manufactured for use in the light-emitting layer of organic light-emitting devices, including the above-described prior art, novel compounds that are still applicable to organic light-emitting devices and have device characteristics of low voltage operation, high efficiency, and long lifespan. The need for development of a compound and an organic light-emitting device containing the same continues to be required.
따라서, 본 발명이 이루고자 하는 첫 번째 기술적 과제는 유기발광소자내 발광층의 인광 호스트 물질로 사용가능한 신규한 유기 화합물을 제공하는 것이다.Therefore, the first technical task to be achieved by the present invention is to provide a novel organic compound that can be used as a phosphorescent host material for the light-emitting layer in an organic light-emitting device.
또한 본 발명이 이루고자 하는 두 번째 기술적 과제는 상기 유기 화합물을 유기발광소자내 호스트 물질로서 포함하는, 저전압, 고효율 및 장수명의 유기발광소자(organic light emitting diode, OLED)를 제공하는 것이다.In addition, the second technical problem to be achieved by the present invention is to provide a low-voltage, high-efficiency, and long-life organic light emitting diode (OLED) containing the organic compound as a host material in the organic light emitting device.
본 발명은 상기 기술적 과제들을 달성하기 위하여, 하기 [화학식 A] 또는 [화학식 B] 로 표시되는 방향족 헤테로고리 화합물을 제공한다.In order to achieve the above technical problems, the present invention provides an aromatic heterocyclic compound represented by [Formula A] or [Formula B] below.
[화학식 A] [Formula A]
Figure PCTKR2023003724-appb-img-000001
Figure PCTKR2023003724-appb-img-000001
[화학식 B] [Formula B]
Figure PCTKR2023003724-appb-img-000002
Figure PCTKR2023003724-appb-img-000002
상기 [화학식 A] 및 [화학식 B]에서,In [Formula A] and [Formula B],
상기 X1은 NR4, O 및 S 중에서 선택되는 어느 하나이며,The X 1 is any one selected from NR 4 , O and S,
상기 Z1 내지 Z8은 서로 동일하거나 상이하고, 각각 독립적으로 CR 또는 N 중에서 선택되는 어느 하나이며,Z 1 to Z 8 are the same or different from each other, and are each independently selected from CR or N,
상기 Z1 내지 Z8이 복수의 CR을 포함하는 경우에 각각의 R은 서로 동일하거나 상이하고,When Z 1 to Z 8 include a plurality of CR, each R is the same as or different from each other,
상기 Z3 내지 Z6 중 하나는 연결기 L과 결합하는 단일결합을 포함하는 탄소원자이고,One of Z 3 to Z 6 is a carbon atom containing a single bond bonded to the linking group L,
상기 R, R1 내지 R4은 서로 동일하거나 상이하며, 각각 독립적으로 수소, 중수소, 치환 또는 비치환된 탄소수 1 내지 30의 알킬기, 치환 또는 비치환된 탄소수 2 내지 30의 알케닐기, 치환 또는 비치환된 탄소수 2 내지 20의 알키닐기, 치환 또는 비치환된 탄소수 6 내지 50의 아릴기, 치환 또는 비치환된 탄소수 3 내지 30의 시클로알킬기, 치환 또는 비치환된 탄소수 5 내지 30의 시클로알케닐기, 치환 또는 비치환된 탄소수 2 내지 30의 헤테로시클로알킬기, 치환 또는 비치환된 탄소수 2 내지 50의 헤테로알킬기, 치환 또는 비치환된 탄소수 2 내지 50의 헤테로아릴기, 치환 또는 비치환된 탄소수 7 내지 30의 방향족 탄화수소 고리가 축합된 시클로알킬기, 치환 또는 비치환된 탄소수 5 내지 30의 방향족 헤테로고리가 축합된 시클로알킬기, 치환 또는 비치환된 탄소수 6 내지 30의 방향족 탄화수소 고리가 축합된 헤테로시클로알킬기, 치환 또는 비치환된 탄소수 8 내지 30의 지방족 탄화수소 고리가 축합된 아릴기, 치환 또는 비치환된 탄소수 5 내지 30의 지방족 탄화수소 고리가 축합된 헤테로아릴기, 치환 또는 비치환된 탄소수 1 내지 30의 알콕시기, 치환 또는 비치환된 탄소수 6 내지 30의 아릴옥시기, 치환 또는 비치환된 탄소수 3 내지 30의 시클로알킬옥시기, 치환 또는 비치환된 탄소수 2 내지 30의 헤테로아릴옥시기, 치환 또는 비치환된 탄소수 1 내지 30의 알킬티오기, 치환 또는 비치환된 탄소수 6 내지 30의 아릴티오기, 치환 또는 비치환된 탄소수 3 내지 30의 시클로알킬티오기, 치환 또는 비치환된 탄소수 2 내지 30의 헤테로아릴티오기, 치환 또는 비치환된 탄소수 0 내지 30의 아민기, 치환 또는 비치환된 탄소수 0 내지 30의 실릴기, 탄소수 0 내지 30의 저마늄기, 니트로기, 시아노기, 할로겐기 중에서 선택되는 어느 하나이며, R, R 1 to R 4 are the same or different from each other, and each independently represents hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, substituted or unsubstituted. A substituted or unsubstituted alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted cycloalkenyl group having 5 to 30 carbon atoms, Substituted or unsubstituted heterocycloalkyl group having 2 to 30 carbon atoms, substituted or unsubstituted heteroalkyl group having 2 to 50 carbon atoms, substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms, substituted or unsubstituted heteroaryl group having 7 to 30 carbon atoms A cycloalkyl group in which an aromatic hydrocarbon ring is condensed, a cycloalkyl group in which a substituted or unsubstituted aromatic heterocycle of 5 to 30 carbon atoms is condensed, a heterocycloalkyl group in which a substituted or unsubstituted aromatic hydrocarbon ring of 6 to 30 carbon atoms is condensed, substituted Or an aryl group in which an unsubstituted aliphatic hydrocarbon ring having 8 to 30 carbon atoms is condensed, a heteroaryl group in which a substituted or unsubstituted aliphatic hydrocarbon ring in the carbon number of 5 to 30 is condensed, or a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms. , a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted cycloalkyloxy group having 3 to 30 carbon atoms, a substituted or unsubstituted heteroaryloxy group having 2 to 30 carbon atoms, a substituted or unsubstituted Alkylthio group with 1 to 30 carbon atoms, substituted or unsubstituted arylthio group with 6 to 30 carbon atoms, substituted or unsubstituted cycloalkylthio group with 3 to 30 carbon atoms, substituted or unsubstituted heteroaryl with 2 to 30 carbon atoms Any one selected from a thio group, a substituted or unsubstituted amine group with 0 to 30 carbon atoms, a substituted or unsubstituted silyl group with 0 to 30 carbon atoms, a germanium group with 0 to 30 carbon atoms, a nitro group, a cyano group, or a halogen group. and
상기 Z1 내지 Z8이 복수의 CR을 포함하는 경우에 서로 인접한 각각의 R은 서로 연결되어 지환족 또는 방향족의 단일환 또는 다환의 고리를 추가 형성할 수 있고, 상기 형성된 지환족, 방향족의 단일환 또는 다환 고리의 탄소원자는 N, S 및 O 중에서 선택되는 어느 하나 이상의 헤테로원자로 치환될 수 있으며,When Z 1 to Z 8 include a plurality of CR, each R adjacent to each other may be connected to each other to further form an alicyclic or aromatic monocyclic or polycyclic ring, and the formed alicyclic or aromatic ring may be The carbon atom of the monocyclic or polycyclic ring may be substituted with one or more heteroatoms selected from N, S and O,
상기 R2 및 R3는 서로 연결되어 지환족 또는 방향족의 단일환 또는 다환의 고리를 추가 형성할 수 있으며,R 2 and R 3 may be connected to each other to further form an alicyclic or aromatic monocyclic or polycyclic ring,
상기 L은 단일결합, 치환 또는 비치환된 탄소수 6 내지 50의 아릴렌기 및 치환 또는 비치환된 탄소수 2 내지 50의 헤테로아릴렌기 중에서 선택되는 어느 하나이고,Wherein L is a single bond, a substituted or unsubstituted arylene group having 6 to 50 carbon atoms and a substituted or unsubstituted heteroarylene group having 2 to 50 carbon atoms,
상기 [화학식 A] 및 [화학식 B] 내 '치환 또는 비치환된'에서의 '치환'은 중수소, 시아노기, 할로겐기, 히드록시기, 니트로기, 탄소수 1 내지 24의 알킬기, 탄소수 1 내지 24의 할로겐화된 알킬기, 탄소수 3 내지 30의 시클로알킬기, 탄소수 2 내지 24의 알케닐기, 탄소수 2 내지 24의 알키닐기, 탄소수 1 내지 24의 헤테로알킬기, 탄소수 6 내지 24의 아릴기, 탄소수 7 내지 24의 아릴알킬기, 탄소수 7 내지 24의 알킬아릴기, 탄소수 2 내지 24의 헤테로아릴기, 탄소수 2 내지 24의 헤테로아릴알킬기, 탄소수 7 내지 24의, 방향족 탄화수소 고리가 축합된 시클로알킬기, 탄소수 5 내지 24의, 방향족 헤테로고리가 축합된 시클로알킬기, 탄소수 6 내지 24의, 방향족 탄화수소 고리가 축합된 헤테로시클로알킬기, 탄소수 8 내지 24의, 지방족 탄화수소 고리가 축합된 아릴기, 탄소수 5 내지 24의, 지방족 탄화수소 고리가 축합된 헤테로아릴기, 탄소수 1 내지 24의 알콕시기, 탄소수 1 내지 24의 아민기, 탄소수 1 내지 24의 실릴기, 탄소수 1 내지 24의 저마늄기, 탄소수 6 내지 24의 아릴옥시기, 탄소수 6 내지 24의 아릴티오닐기로 이루어진 군에서 선택된 1개 이상의 치환기로 치환되는 것을 의미하며, 상기 각각의 치환기내 하나 이상의 수소는 중수소로 치환가능하다.'Substitution' in 'substituted or unsubstituted' in [Formula A] and [Formula B] means deuterium, cyano group, halogen group, hydroxy group, nitro group, alkyl group with 1 to 24 carbon atoms, halogenation with 1 to 24 carbon atoms. alkyl group, cycloalkyl group with 3 to 30 carbon atoms, alkenyl group with 2 to 24 carbon atoms, alkynyl group with 2 to 24 carbon atoms, heteroalkyl group with 1 to 24 carbon atoms, aryl group with 6 to 24 carbon atoms, arylalkyl group with 7 to 24 carbon atoms , an alkylaryl group having 7 to 24 carbon atoms, a heteroaryl group having 2 to 24 carbon atoms, a heteroarylalkyl group having 2 to 24 carbon atoms, a cycloalkyl group in which an aromatic hydrocarbon ring is condensed, having 7 to 24 carbon atoms, and an aromatic group having 5 to 24 carbon atoms. Cycloalkyl group with a condensed hetero ring, a heterocycloalkyl group with a condensed aromatic hydrocarbon ring having 6 to 24 carbon atoms, an aryl group with a condensed aliphatic hydrocarbon ring with 8 to 24 carbon atoms, and a condensed aliphatic hydrocarbon ring with 5 to 24 carbon atoms. heteroaryl group, alkoxy group of 1 to 24 carbon atoms, amine group of 1 to 24 carbon atoms, silyl group of 1 to 24 carbon atoms, germanium group of 1 to 24 carbon atoms, aryloxy group of 6 to 24 carbon atoms, 6 to 24 carbon atoms means being substituted with one or more substituents selected from the group consisting of arylthionyl groups, and one or more hydrogens in each substituent can be replaced with deuterium.
본 발명에 따른 상기 화학식 A 또는 화학식 B로 표시되는 방향족 헤테로고리 화합물을 유기발광소자내 발광층의 인광 호스트 물질로 이용하는 경우에, 종래기술에 따른 유기발광소자에 비하여 보다 저전압, 고효율 및 장수명의 특성을 구현할 수 있는 유기발광소자를 제공할 수 있다. When the aromatic heterocyclic compound represented by Formula A or Formula B according to the present invention is used as a phosphorescent host material for the light-emitting layer in an organic light-emitting device, it has lower voltage, higher efficiency, and longer lifespan compared to the organic light-emitting device according to the prior art. An organic light emitting device that can be implemented can be provided.
도 1은 본 발명의 일 구체예에 따른 유기 발광 소자의 개략도이다.1 is a schematic diagram of an organic light-emitting device according to an embodiment of the present invention.
이하, 본 발명을 더욱 상세하게 설명한다. 본 발명의 각 도면에 있어서, 구조물들의 사이즈나 치수는 본 발명의 명확성을 기하기 위하여 실제보다 확대하거나 축소하여 도시한 것이고, 특징적 구성이 드러나도록 공지의 구성들은 생략하여 도시하였으므로 도면으로 한정하지는 아니한다. Hereinafter, the present invention will be described in more detail. In each drawing of the present invention, the size or dimensions of the structures are enlarged or reduced from the actual size for clarity of the present invention, and known structures are omitted to reveal the characteristic structure, so it is not limited to the drawing. .
또한, 도면에서 나타난 각 구성의 크기 및 두께는 설명의 편의를 위해 임의로 나타내었으므로, 본 발명이 반드시 도시된 바에 한정되지 않으며, 또한 도면에서 여러 층 및 영역을 명확하게 표현하기 위하여 두께를 확대하여 나타내었다. 그리고 도면에서, 설명의 편의를 위해, 일부 층 및 영역의 두께를 과장되게 나타내었다. 층, 막, 영역, 판 등의 부분이 다른 부분 "상에" 있다고 할 때, 이는 다른 부분 "바로 상에" 있는 경우뿐 아니라 그 중간에 또 다른 부분이 있는 경우도 포함한다.In addition, the size and thickness of each component shown in the drawings are arbitrarily shown for convenience of explanation, so the present invention is not necessarily limited to what is shown, and the thickness is enlarged to clearly express various layers and regions in the drawings. indicated. And in the drawings, for convenience of explanation, the thicknesses of some layers and regions are exaggerated. When a part of a layer, membrane, region, plate, etc. is said to be “on” another part, this includes not only being “directly on” the other part, but also cases where there is another part in between.
또한, 명세서 전체에서, 어떤 부분이 어떤 구성요소를 "포함" 한다고 할 때, 이는 특별히 반대되는 기재가 없는 한 다른 구성요소를 제외하는 것이 아니라 다른 구성요소를 더 포함할 수 있는 것을 의미한다. 또한, 명세서 전체에서, "~상에"라 함은 대상 부분의 위 또는 아래에 위치함을 의미하는 것이며, 반드시 중력 방향을 기준으로 상측에 위치하는 것을 의미하는 것은 아니다.In addition, throughout the specification, when a part is said to "include" a certain component, this means that it may further include other components rather than excluding other components, unless specifically stated to the contrary. In addition, throughout the specification, “on” means located above or below the object part, and does not necessarily mean located above the direction of gravity.
본 발명은 하기 [화학식 A] 또는 [화학식 B] 로 표시되는 방향족 헤테로고리 화합물을 제공한다.The present invention provides an aromatic heterocyclic compound represented by the following [Formula A] or [Formula B].
[화학식 A] [Formula A]
Figure PCTKR2023003724-appb-img-000003
Figure PCTKR2023003724-appb-img-000003
[화학식 B] [Formula B]
Figure PCTKR2023003724-appb-img-000004
Figure PCTKR2023003724-appb-img-000004
상기 [화학식 A] 및 [화학식 B]에서,In [Formula A] and [Formula B],
상기 X1은 NR4, O 및 S 중에서 선택되는 어느 하나이며,The X 1 is any one selected from NR 4 , O and S,
상기 Z1 내지 Z8은 서로 동일하거나 상이하고, 각각 독립적으로 CR 또는 N 중에서 선택되는 어느 하나이며,Z 1 to Z 8 are the same or different from each other, and are each independently selected from CR or N,
상기 Z1 내지 Z8이 복수의 CR을 포함하는 경우에 각각의 R은 서로 동일하거나 상이하고,When Z 1 to Z 8 include a plurality of CR, each R is the same as or different from each other,
상기 Z3 내지 Z6 중 하나는 연결기 L과 결합하는 단일결합을 포함하는 탄소원자이고,One of Z 3 to Z 6 is a carbon atom containing a single bond bonded to the linking group L,
상기 R, R1 내지 R4은 서로 동일하거나 상이하며, 각각 독립적으로 수소, 중수소, 치환 또는 비치환된 탄소수 1 내지 30의 알킬기, 치환 또는 비치환된 탄소수 2 내지 30의 알케닐기, 치환 또는 비치환된 탄소수 2 내지 20의 알키닐기, 치환 또는 비치환된 탄소수 6 내지 50의 아릴기, 치환 또는 비치환된 탄소수 3 내지 30의 시클로알킬기, 치환 또는 비치환된 탄소수 5 내지 30의 시클로알케닐기, 치환 또는 비치환된 탄소수 2 내지 30의 헤테로시클로알킬기, 치환 또는 비치환된 탄소수 2 내지 50의 헤테로알킬기, 치환 또는 비치환된 탄소수 2 내지 50의 헤테로아릴기, 치환 또는 비치환된 탄소수 7 내지 30의 방향족 탄화수소 고리가 축합된 시클로알킬기, 치환 또는 비치환된 탄소수 5 내지 30의 방향족 헤테로고리가 축합된 시클로알킬기, 치환 또는 비치환된 탄소수 6 내지 30의 방향족 탄화수소 고리가 축합된 헤테로시클로알킬기, 치환 또는 비치환된 탄소수 8 내지 30의 지방족 탄화수소 고리가 축합된 아릴기, 치환 또는 비치환된 탄소수 5 내지 30의 지방족 탄화수소 고리가 축합된 헤테로아릴기, 치환 또는 비치환된 탄소수 1 내지 30의 알콕시기, 치환 또는 비치환된 탄소수 6 내지 30의 아릴옥시기, 치환 또는 비치환된 탄소수 3 내지 30의 시클로알킬옥시기, 치환 또는 비치환된 탄소수 2 내지 30의 헤테로아릴옥시기, 치환 또는 비치환된 탄소수 1 내지 30의 알킬티오기, 치환 또는 비치환된 탄소수 6 내지 30의 아릴티오기, 치환 또는 비치환된 탄소수 3 내지 30의 시클로알킬티오기, 치환 또는 비치환된 탄소수 2 내지 30의 헤테로아릴티오기, 치환 또는 비치환된 탄소수 0 내지 30의 아민기, 치환 또는 비치환된 탄소수 0 내지 30의 실릴기, 탄소수 0 내지 30의 저마늄기, 니트로기, 시아노기, 할로겐기 중에서 선택되는 어느 하나이며, R, R 1 to R 4 are the same or different from each other, and each independently represents hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, substituted or unsubstituted. A substituted or unsubstituted alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted cycloalkenyl group having 5 to 30 carbon atoms, Substituted or unsubstituted heterocycloalkyl group having 2 to 30 carbon atoms, substituted or unsubstituted heteroalkyl group having 2 to 50 carbon atoms, substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms, substituted or unsubstituted heteroaryl group having 7 to 30 carbon atoms A cycloalkyl group in which an aromatic hydrocarbon ring is condensed, a cycloalkyl group in which a substituted or unsubstituted aromatic heterocycle of 5 to 30 carbon atoms is condensed, a heterocycloalkyl group in which a substituted or unsubstituted aromatic hydrocarbon ring of 6 to 30 carbon atoms is condensed, substituted Or an aryl group in which an unsubstituted aliphatic hydrocarbon ring having 8 to 30 carbon atoms is condensed, a heteroaryl group in which a substituted or unsubstituted aliphatic hydrocarbon ring in the carbon number of 5 to 30 is condensed, or a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms. , a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted cycloalkyloxy group having 3 to 30 carbon atoms, a substituted or unsubstituted heteroaryloxy group having 2 to 30 carbon atoms, a substituted or unsubstituted Alkylthio group with 1 to 30 carbon atoms, substituted or unsubstituted arylthio group with 6 to 30 carbon atoms, substituted or unsubstituted cycloalkylthio group with 3 to 30 carbon atoms, substituted or unsubstituted heteroaryl with 2 to 30 carbon atoms Any one selected from a thio group, a substituted or unsubstituted amine group with 0 to 30 carbon atoms, a substituted or unsubstituted silyl group with 0 to 30 carbon atoms, a germanium group with 0 to 30 carbon atoms, a nitro group, a cyano group, or a halogen group. and
상기 Z1 내지 Z8이 복수의 CR을 포함하는 경우에 서로 인접한 각각의 R은 서로 연결되어 지환족 또는 방향족의 단일환 또는 다환의 고리를 추가 형성할 수 있고, 상기 형성된 지환족, 방향족의 단일환 또는 다환 고리의 탄소원자는 N, S 및 O 중에서 선택되는 어느 하나 이상의 헤테로원자로 치환될 수 있으며,When Z 1 to Z 8 include a plurality of CR, each R adjacent to each other may be connected to each other to further form an alicyclic or aromatic monocyclic or polycyclic ring, and the formed alicyclic or aromatic ring may be The carbon atom of the monocyclic or polycyclic ring may be substituted with one or more heteroatoms selected from N, S and O,
상기 R2 및 R3는 서로 연결되어 지환족 또는 방향족의 단일환 또는 다환의 고리를 추가 형성할 수 있으며,R 2 and R 3 may be connected to each other to further form an alicyclic or aromatic monocyclic or polycyclic ring,
상기 L은 단일결합, 치환 또는 비치환된 탄소수 6 내지 50의 아릴렌기 및 치환 또는 비치환된 탄소수 2 내지 50의 헤테로아릴렌기 중에서 선택되는 어느 하나이고,Wherein L is a single bond, a substituted or unsubstituted arylene group having 6 to 50 carbon atoms and a substituted or unsubstituted heteroarylene group having 2 to 50 carbon atoms,
상기 [화학식 A] 및 [화학식 B] 내 '치환 또는 비치환된'에서의 '치환'은 중수소, 시아노기, 할로겐기, 히드록시기, 니트로기, 탄소수 1 내지 24의 알킬기, 탄소수 1 내지 24의 할로겐화된 알킬기, 탄소수 3 내지 30의 시클로알킬기, 탄소수 2 내지 24의 알케닐기, 탄소수 2 내지 24의 알키닐기, 탄소수 1 내지 24의 헤테로알킬기, 탄소수 6 내지 24의 아릴기, 탄소수 7 내지 24의 아릴알킬기, 탄소수 7 내지 24의 알킬아릴기, 탄소수 2 내지 24의 헤테로아릴기, 탄소수 2 내지 24의 헤테로아릴알킬기, 탄소수 7 내지 24의, 방향족 탄화수소 고리가 축합된 시클로알킬기, 탄소수 5 내지 24의, 방향족 헤테로고리가 축합된 시클로알킬기, 탄소수 6 내지 24의, 방향족 탄화수소 고리가 축합된 헤테로시클로알킬기, 탄소수 8 내지 24의, 지방족 탄화수소 고리가 축합된 아릴기, 탄소수 5 내지 24의, 지방족 탄화수소 고리가 축합된 헤테로아릴기, 탄소수 1 내지 24의 알콕시기, 탄소수 1 내지 24의 아민기, 탄소수 1 내지 24의 실릴기, 탄소수 1 내지 24의 저마늄기, 탄소수 6 내지 24의 아릴옥시기, 탄소수 6 내지 24의 아릴티오닐기로 이루어진 군에서 선택된 1개 이상의 치환기로 치환되는 것을 의미하며, 상기 각각의 치환기내 하나 이상의 수소는 중수소로 치환가능하다.'Substitution' in 'substituted or unsubstituted' in [Formula A] and [Formula B] means deuterium, cyano group, halogen group, hydroxy group, nitro group, alkyl group with 1 to 24 carbon atoms, halogenation with 1 to 24 carbon atoms. alkyl group, cycloalkyl group with 3 to 30 carbon atoms, alkenyl group with 2 to 24 carbon atoms, alkynyl group with 2 to 24 carbon atoms, heteroalkyl group with 1 to 24 carbon atoms, aryl group with 6 to 24 carbon atoms, arylalkyl group with 7 to 24 carbon atoms , an alkylaryl group having 7 to 24 carbon atoms, a heteroaryl group having 2 to 24 carbon atoms, a heteroarylalkyl group having 2 to 24 carbon atoms, a cycloalkyl group in which an aromatic hydrocarbon ring is condensed, having 7 to 24 carbon atoms, and an aromatic group having 5 to 24 carbon atoms. Cycloalkyl group with a condensed hetero ring, a heterocycloalkyl group with a condensed aromatic hydrocarbon ring having 6 to 24 carbon atoms, an aryl group with a condensed aliphatic hydrocarbon ring with 8 to 24 carbon atoms, and a condensed aliphatic hydrocarbon ring with 5 to 24 carbon atoms. heteroaryl group, alkoxy group of 1 to 24 carbon atoms, amine group of 1 to 24 carbon atoms, silyl group of 1 to 24 carbon atoms, germanium group of 1 to 24 carbon atoms, aryloxy group of 6 to 24 carbon atoms, 6 to 24 carbon atoms means being substituted with one or more substituents selected from the group consisting of arylthionyl groups, and one or more hydrogens in each substituent can be replaced with deuterium.
한편, 본 발명에서의 상기 "치환 또는 비치환된 탄소수 1 내지 30의 알킬기", "치환 또는 비치환된 탄소수 5 내지 50의 아릴기" 등에서의 상기 알킬기 또는 아릴기의 범위를 고려하여 보면, 상기 탄소수 1 내지 30의 알킬기 및 탄소수 5 내지 50의 아릴기의 탄소수의 범위는 각각 상기 치환기가 치환된 부분을 고려하지 않고 비치환된 것으로 보았을 때의 알킬 부분 또는 아릴 부분을 구성하는 전체 탄소수를 의미하는 것이다. 예컨대, 파라위치에 부틸기가 치환된 페닐기는 탄소수 4의 부틸기로 치환된 탄소수 6의 아릴기에 해당하는 것으로 보아야 한다. Meanwhile, considering the range of the alkyl group or aryl group in the “substituted or unsubstituted alkyl group having 1 to 30 carbon atoms” and “substituted or unsubstituted aryl group having 5 to 50 carbon atoms” in the present invention, the The range of the carbon number of the alkyl group having 1 to 30 carbon atoms and the aryl group having 5 to 50 carbon atoms means the total number of carbon atoms constituting the alkyl portion or aryl portion when the substituent is regarded as unsubstituted without considering the substituted portion, respectively. will be. For example, a phenyl group substituted with a butyl group at the para position should be viewed as corresponding to an aryl group with 6 carbon atoms substituted with a butyl group with 4 carbon atoms.
본 발명의 화합물에서 사용되는 치환기인 아릴기는 하나의 수소 제거에 의해서 방향족 탄화수소로부터 유도된 유기 라디칼로, 상기 아릴기가 치환기가 있는 경우 서로 이웃하는 치환기와 서로 융합 (fused)되어 고리를 추가로 형성할 수 있고, 또한, 상기 아릴기는 두 개의 아렌고리가 서로 축합되어 이루어진 아렌고리로부터 하나의 수소 제거에 의해 얻어지는 유기라디칼을 포함할 수 있다.The aryl group, which is a substituent used in the compound of the present invention, is an organic radical derived from an aromatic hydrocarbon by removal of one hydrogen. When the aryl group has a substituent, it can be fused with neighboring substituents to further form a ring. Additionally, the aryl group may include an organic radical obtained by removing one hydrogen from an arene ring formed by condensing two arene rings.
상기 아릴기의 구체적인 예로는 페닐기, o-비페닐기, m-비페닐기, p-비페닐기, o-터페닐기, m-터페닐기, p-터페닐기, 나프틸기, 안트릴기, 페난트릴기, 피레닐기, 인데닐기, 플루오레닐기, 테트라히드로나프틸기, 페릴레닐기, 크라이세닐기, 나프타세닐기, 플루오란테닐기 등과 같은 방향족 라디칼 그룹을 들 수 있고, 플루오렌 고리와 페닐렌고리가 축합된 아렌고리, 또는 플루오렌 고리와 페난트렌 고리가 축합된 아렌고리 등의 두개의 아렌고리가 축합되어 이루어진 아렌고리내 하나의 수소제거에 의한 유기 라디칼을 또한 포함할 수 있다.Specific examples of the aryl group include phenyl group, o-biphenyl group, m-biphenyl group, p-biphenyl group, o-terphenyl group, m-terphenyl group, p-terphenyl group, naphthyl group, anthryl group, phenanthryl group, Aromatic radical groups such as pyrenyl group, indenyl group, fluorenyl group, tetrahydronaphthyl group, perylenyl group, chrysenyl group, naphthacenyl group, fluoranthenyl group, etc. can be mentioned, and the fluorene ring and the phenylene ring are condensed. It may also include an organic radical resulting from the removal of one hydrogen in an arene ring formed by condensing two arene rings, such as an arene ring or an arene ring in which a fluorene ring and a phenanthrene ring are condensed.
또한, 상기 아릴기 중 하나 이상의 수소 원자는 중수소 원자, 할로겐 원자, 히드록시기, 니트로기, 시아노기, 실릴기, 아미노기 (-NH2, -NH(R), -N(R')(R''), R'과 R"은 서로 독립적으로 탄소수 1 내지 10의 알킬기이며, 이 경우 "알킬아미노기"라 함), 아미디노기, 히드라진기, 히드라존기, 카르복실기, 술폰산기, 인산기, 탄소수 1 내지 24의 알킬기, 탄소수 1 내지 24의 할로겐화된 알킬기, 탄소수 2 내지 24의 알케닐기, 탄소수 2 내지 24의 알키닐기, 탄소수 1 내지 24의 헤테로알킬기, 탄소수 6 내지 24의 아릴기, 탄소수 7 내지 24의 아릴알킬기, 탄소수 7 내지 24의 알킬아릴기, 탄소수 2 내지 24의 헤테로아릴기, 탄소수 3 내지 24의 헤테로아릴알킬기 또는 탄소수 3 내지 24의 알킬헤테로아릴기로 치환될 수 있다.In addition, one or more hydrogen atoms of the aryl group may be a deuterium atom, a halogen atom, a hydroxy group, a nitro group, a cyano group, a silyl group, an amino group (-NH 2 , -NH(R), -N(R')(R'' ), R' and R" are independently an alkyl group having 1 to 10 carbon atoms, in this case referred to as an "alkylamino group"), amidino group, hydrazine group, hydrazone group, carboxyl group, sulfonic acid group, phosphoric acid group, carbon number 1 to 24 alkyl group, halogenated alkyl group with 1 to 24 carbon atoms, alkenyl group with 2 to 24 carbon atoms, alkynyl group with 2 to 24 carbon atoms, heteroalkyl group with 1 to 24 carbon atoms, aryl group with 6 to 24 carbon atoms, aryl with 7 to 24 carbon atoms It may be substituted with an alkyl group, an alkylaryl group with 7 to 24 carbon atoms, a heteroaryl group with 2 to 24 carbon atoms, a heteroarylalkyl group with 3 to 24 carbon atoms, or an alkylheteroaryl group with 3 to 24 carbon atoms.
본 발명에서의 상기 방향족 탄화수소 고리는 탄소와 수소로 이루어진 방향족 고리를 의미하며, 또한, 상기 지방족 탄화수소 고리는 탄소와 수소로 이루어지되, 방향족 탄화수소 고리에 속하지 않는 탄화수소 고리를 의미하며, 이때, 상기 지방족 탄화수소 고리는 바람직하게는, 고리를 형성하는 탄소 원자 중 적어도 30% 이상이 sp3 오비탈 구조를 통해 결합을 이루며, 고리내에 이중결합 및/또는 삼중결합을 0 내지 3개 포함하는 탄화수소 고리일 수 있고, 더욱 바람직하게는 고리를 형성하는 탄소 원자 중 적어도 50% 이상이 sp3 오비탈에 의해 결합을 이루며, 고리내에 이중결합 및/또는 삼중결합을 0 내지 2개 포함하는 탄화수소 고리일 수 있다.In the present invention, the aromatic hydrocarbon ring refers to an aromatic ring made up of carbon and hydrogen, and the aliphatic hydrocarbon ring refers to a hydrocarbon ring made up of carbon and hydrogen but does not belong to the aromatic hydrocarbon ring. In this case, the aliphatic ring refers to a hydrocarbon ring made up of carbon and hydrogen. The hydrocarbon ring is preferably a hydrocarbon ring in which at least 30% or more of the carbon atoms forming the ring are bonded through an sp 3 orbital structure and contain 0 to 3 double bonds and/or triple bonds in the ring. , more preferably, at least 50% or more of the carbon atoms forming the ring are bonded by sp 3 orbitals, and may be a hydrocarbon ring containing 0 to 2 double bonds and/or triple bonds in the ring.
또한, 본 발명에서의 상기 지방족 탄화수소 고리가 축합된 아릴기는 지방족 탄화수소 고리 중 서로 인접한 두 개의 탄소원자와, 아릴기내 고리를 이루는 탄소원자 중 하나의 수소 제거에 의해서 유기 라디칼이 된 탄소 원자를 제외한 두 개의 서로 인접한 탄소원자가 서로 축합되어 하나의 이중결합을 공유하고 전체적으로 비방향족성(non-aromaticity)을 가지는 고리형 치환기를 의미하며, 구체적인 예로는 테트라히드로나프틸기, 테트라히드로벤조시클로헵텐, 테트라히드로페난트렌기, 테트라히드로안트라세닐기, 옥타히드로트리페닐렌기 등을 들 수 있다.In addition, in the present invention, the aryl group in which the aliphatic hydrocarbon ring is condensed consists of two carbon atoms adjacent to each other in the aliphatic hydrocarbon ring and two carbon atoms excluding the carbon atom that becomes an organic radical by removing the hydrogen of one of the carbon atoms forming the ring in the aryl group. It refers to a cyclic substituent in which two adjacent carbon atoms are condensed together to share one double bond and has overall non-aromaticity. Specific examples include tetrahydronaphthyl group, tetrahydrobenzocycloheptene, and tetrahydrophene. Nantrene group, tetrahydroanthracenyl group, octahydrotriphenylene group, etc. are mentioned.
본 발명의 화합물에서 사용되는 치환기인 헤테로아릴기는 방향족 고리내 N, O, P, Si, S, Ge, Se, Te 중에서 선택된 1, 2 또는 3개의 헤테로 원자를 포함하고, 나머지 고리 원자가 탄소인 탄소수 2 내지 24의 고리 방향족 시스템의 아릴기를 의미하며, 상기 고리들은 융합(fused)되어 고리를 형성할 수 있다. 그리고 상기 헤테로아릴기 중 하나 이상의 수소 원자는 상기 아릴기의 경우와 마찬가지의 치환기로 치환가능하다.The heteroaryl group, which is a substituent used in the compound of the present invention, contains 1, 2, or 3 heteroatoms selected from N, O, P, Si, S, Ge, Se, and Te in the aromatic ring, and the remaining ring atom is carbon. It refers to an aryl group of an aromatic system with 2 to 24 rings, and the rings can be fused to form a ring. And one or more hydrogen atoms of the heteroaryl group may be replaced with the same substituent as that of the aryl group.
또한 본 발명에서 상기 방향족 헤테로고리는 방향족 탄화수소 고리에서 방향족 탄소중 하나이상이 헤테로 원자로 치환된 것을 의미하며, 상기 방향족 헤테로 고리는 바람직하게는 방향족 탄화수소내 방향족 탄소 1 내지 3개가 N, O, P, Si, S, Ge, Se, Te 중에서 선택된 하나이상의 헤테로원자로 치환될 수 있다. In addition, in the present invention, the aromatic heterocycle means that one or more aromatic carbons in the aromatic hydrocarbon ring are substituted with a hetero atom, and the aromatic hetero ring preferably has 1 to 3 aromatic carbons in the aromatic hydrocarbon ring consisting of N, O, P, It may be substituted with one or more heteroatoms selected from Si, S, Ge, Se, and Te.
또한, 지방족 탄화수소 고리가 축합된 헤테로아릴기는 상기 지방족 탄화수소 고리가 축합된 아릴기에서 아릴기 대신에 헤테로아릴기가 치환된 구조의 치환기로서, 구체적인 예로는 테트라히드로인돌기, 테트라히드로벤조퓨라닐기, 테트라히드로벤조티오펜기, 테트라히드로카바졸기, 테트라히드로디벤조퓨라닐기, 테트라히드로벤조티오펜기, 테트라히드로퀴놀린기, 테트라히드로퀴녹살린기 등을 들 수 있다. In addition, heteroaryl groups in which aliphatic hydrocarbon rings are condensed A substituent having a structure in which a heteroaryl group is substituted for an aryl group in the aryl group in which the aliphatic hydrocarbon ring is condensed, specific examples include tetrahydroindole group, tetrahydrobenzofuranyl group, tetrahydrobenzothiophene group, tetrahydrocarbazole group, Tetrahydrodibenzofuranyl group, tetrahydrobenzothiophene group, tetrahydroquinoline group, tetrahydroquinoxaline group, etc. are mentioned.
또한 본 발명에서 상기 방향족 헤테로고리는 방향족 탄화수소 고리에서 방향족 탄소중 하나이상이 헤테로 원자로 치환된 것을 의미하며, 상기 방향족 헤테로 고리는 바람직하게는 방향족 탄화수소내 방향족 탄소 1 내지 3개가 N, O, P, Si, S, Ge, Se, Te 중에서 선택된 하나이상의 헤테로원자로 치환될 수 있다. In addition, in the present invention, the aromatic heterocycle means that one or more aromatic carbons in the aromatic hydrocarbon ring are substituted with a hetero atom, and the aromatic hetero ring preferably has 1 to 3 aromatic carbons in the aromatic hydrocarbon ring consisting of N, O, P, It may be substituted with one or more heteroatoms selected from Si, S, Ge, Se, and Te.
본 발명에서 상기 '방향족 탄화수소 고리와 지방족 탄화수소 고리가 축합된 축합 고리'는 방향족 탄화수소 고리 중 서로 인접한 두 개의 탄소원자와 지방족 탄화수소 고리 중 두 개의 서로 인접한 탄소원자가 서로 공유되도록 축합된 축합고리를 의미하며, 예시적으로 벤젠 고리와 시클로헥산고리에서 각각의 서로 인접한 2 개의 탄소원자가 공유되어 축합된, 테트라히드로나프탈렌 고리를 들 수 있다. In the present invention, the 'condensed ring in which an aromatic hydrocarbon ring and an aliphatic hydrocarbon ring are condensed' means a condensed ring in which two adjacent carbon atoms of an aromatic hydrocarbon ring and two adjacent carbon atoms of an aliphatic hydrocarbon ring are shared. , Examples include a tetrahydronaphthalene ring in which two carbon atoms adjacent to each other in a benzene ring and a cyclohexane ring are shared and condensed.
또한, 본 발명에서의 상기 '방향족 헤테로고리와 지방족 탄화수소 고리가 축합된 축합 고리'는 방향족 헤테로고리 중 서로 인접한 두 개의 탄소원자와 지방족 탄화수소 고리 중 두 개의 서로 인접한 탄소원자가 서로 공유되도록 축합된 축합고리를 의미하며, 예시적으로 벤조퓨란 고리와 시클로헥산고리에서 각각의 고리내 서로 인접한 2 개의 탄소원자가 서로 공유되어 축합된, 헥사히드로디벤조퓨란 고리를 들 수 있다.In addition, in the present invention, the 'condensed ring in which an aromatic heterocycle and an aliphatic hydrocarbon ring are condensed' is a condensed ring in which two adjacent carbon atoms of an aromatic heterocycle and two adjacent carbon atoms of an aliphatic hydrocarbon ring are shared. It means, and an example is a hexahydrodibenzofuran ring in which two adjacent carbon atoms in each ring of a benzofuran ring and a cyclohexane ring are shared and condensed.
본 발명에서 사용되는 치환기인 알킬기는 알칸(alkane)으로부터 수소 하나가 제거된 치환기로서, 직쇄형, 분지형을 포함하는 구조이며, 이의 구체적인 예로는 메틸, 에틸, 프로필, 이소프로필, 이소부틸, sec-부틸, tert-부틸, 펜틸, iso-아밀, 헥실 등을 들 수 있고, 상기 알킬기 중 하나 이상의 수소 원자는 원자는 상기 아릴기의 경우와 마찬가지의 치환기로 치환가능하다.The alkyl group, which is a substituent used in the present invention, is a substituent in which one hydrogen is removed from an alkane, and has a straight-chain and branched structure, and specific examples thereof include methyl, ethyl, propyl, isopropyl, isobutyl, and sec. -butyl, tert-butyl, pentyl, iso-amyl, hexyl, etc., and one or more hydrogen atoms of the alkyl group may be replaced with the same substituent as that of the aryl group.
본 발명의 화합물에서 사용되는 치환기인 시클로알킬기, 시클로알콕시기 등에서의 '시클로'는 알킬기 또는 알콕시기내 포화탄화수소의 단일 고리 또는 다중 고리를 형성할 수 있는 구조의 치환기를 의미하며, 예컨대 시클로알킬기의 구체적인 예로는 시클로프로필, 시클로부틸, 시클로펜틸, 시클로헥실, 메틸시클로펜틸, 메틸시클로헥실, 에틸시클로펜틸, 에틸시클로헥실, 아다만틸, 디시클로펜타디에닐, 데카히드로나프틸, 노보닐, 보닐, 아이소보닐 등을 들 수 있고, 상기 시클로알킬기 중 하나 이상의 수소 원자는 상기 아릴기의 경우와 마찬가지의 치환기로 치환가능 하며, 이는 시클로알콕시에서도 마찬가지로 적용될 수 있다.'Cyclo' in the cycloalkyl group, cycloalkoxy group, etc., which are substituents used in the compound of the present invention, refers to a substituent with a structure capable of forming a single ring or multiple rings of a saturated hydrocarbon in an alkyl or alkoxy group, for example, the specific substituent of the cycloalkyl group. Examples include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, methylcyclopentyl, methylcyclohexyl, ethylcyclopentyl, ethylcyclohexyl, adamantyl, dicyclopentadienyl, decahydronaphthyl, norbornyl, bornyl, Isobornyl, etc. may be mentioned, and one or more hydrogen atoms of the cycloalkyl group may be replaced by the same substituent as that of the aryl group, and this may also be applied to cycloalkoxy.
또한 본 발명에서, 상기 헤테로시클로알킬기는 시클로알킬 구조를 이루는 치환기의 고리내 탄소 중 하나 이상이 헤테로 원자로 치환된 것을 의미하고, 바람직하게는, 1 내지 3개의 탄소가 N, O, P, S, Si, Ge, Se, Te 중에서 선택된 하나이상의 헤테로원자로 치환될 수 있다.In addition, in the present invention, the heterocycloalkyl group means that at least one carbon in the ring of the substituent forming the cycloalkyl structure is substituted with a hetero atom, preferably, 1 to 3 carbons are N, O, P, S, It may be substituted with one or more heteroatoms selected from Si, Ge, Se, and Te.
또한, 상기 방향족 탄화수소 고리 또는 방향족 헤테로 고리가 축합된 시클로알킬기는 방향족 탄화수소 고리 또는 방향족 헤테로 고리내에 서로 인접한 두 개의 탄소원자;와, 시클로알킬기내 고리를 이루는 탄소원자 중 하나의 수소 제거에 의해서 유기 라디칼이 된 탄소 원자를 제외한 두 개의 서로 인접한 탄소원자;가 서로 축합되어 하나의 이중결합을 공유하고, 전체적으로 비방향족성(non-aromaticity)을 나타내는 고리형 치환기를 의미하며, 구체적인 예로는 테트라히드로나프틸, 테트라히드로페난트렌기, 테트라히드로퀴놀린기, 테트라히드로퀴녹살린기, 시클로펜타벤조퓨란 등을 들 수 있다.In addition, the cycloalkyl group in which the aromatic hydrocarbon ring or aromatic hetero ring is condensed contains two carbon atoms adjacent to each other in the aromatic hydrocarbon ring or aromatic hetero ring; and an organic radical by removal of hydrogen from one of the carbon atoms forming the ring in the cycloalkyl group. means a cyclic substituent that is condensed with each other and shares one double bond, and exhibits overall non-aromaticity; a specific example is tetrahydronaphthyl. , tetrahydrophenanthrene group, tetrahydroquinoline group, tetrahydroquinoxaline group, cyclopentabenzofuran, etc.
또한, 상기 방향족 탄화수소 고리가 축합된 헤테로시클로알킬기는 상기 방향족 탄화수소 고리가 축합된 시클로알킬기에서 시클로알킬 고리내 탄소원자 중 하나 이상이 헤테로 원자로 치환된 것을 의미하고, 바람직하게는 시클로알킬 고리내 1 내지 3개의 탄소가 N, O, P, S, Si, Ge, Se, Te 중에서 선택된 하나이상의 헤테로원자로 치환된 구조의 치환기이며, 구체적인 예로는 헥사히드로디벤조퓨라닐기, 헥사히드로카바졸기, 헥사히드로디벤조티오펜기, 디히드로벤조디옥신기 등을 들 수 있으며, 전체적으로 비방향족성(non-aromaticity)을 나타낸다.In addition, the heterocycloalkyl group in which the aromatic hydrocarbon ring is condensed means that one or more carbon atoms in the cycloalkyl ring in the cycloalkyl group in which the aromatic hydrocarbon ring is condensed are substituted with a hetero atom, and preferably 1 to 1 in the cycloalkyl ring. It is a substituent in which three carbons are substituted with one or more heteroatoms selected from N, O, P, S, Si, Ge, Se, and Te. Specific examples include hexahydrodibenzofuranyl group, hexahydrocarbazole group, and hexahydrodi. Benzothiophene group, dihydrobenzodioxine group, etc. are included, and overall, it shows non-aromaticity.
또한, 지방족 헤테로고리가 축합된 아릴기 또는 헤테로아릴기는 상기 지방족 탄화수소 고리가 축합된 아릴기 또는 헤테로아릴기에서 지방족 탄화수소 고리 대신 지방족 헤테로고리가 축합된 구조의 치환기로서, 구체적인 예로는 크로만기, 디하이드로피라노피리딘기, 티오크로만기, 디하이드로벤조다이옥신기, 디하이드로티오피라노피리딘기, 디하이드로피라노피리미딘기 등을 들 수 있으며, 전체적으로 비방향족성(non-aromaticity)을 나타낸다.In addition, an aryl group or heteroaryl group in which an aliphatic heterocycle is condensed A substituent having a structure in which an aliphatic heterocycle is condensed instead of an aliphatic hydrocarbon ring in the aryl group or heteroaryl group in which the aliphatic hydrocarbon ring is condensed. Specific examples include chroman group, dihydropyranopyridine group, thiochroman group, and dihydrobenzodioxin. group, dihydrothiopyranopyridine group, dihydropyranopyrimidine group, etc., and shows non-aromaticity overall.
또한 상기 지방족 헤테로고리는 지방족 탄화수소고리 내 탄소중 하나이상이 헤테로 원자로 치환된 것을 의미하며, 상기 지방족 헤테로 고리는 바람직하게는 지방족 탄화수소내 탄소 1 내지 3개가 N, O 또는 S 등으로 선택된 하나이상의 헤테로원자로 치환될 수 있다. In addition, the aliphatic heterocycle means that at least one carbon in the aliphatic hydrocarbon ring is substituted with a hetero atom, and the aliphatic heterocycle preferably has 1 to 3 carbon atoms in the aliphatic hydrocarbon ring at least one hetero atom selected from N, O, or S. It can be replaced with an atom.
본 발명의 화합물에서 사용되는 치환기인 알콕시기는 알킬기 또는 시클로알킬기의 말단에 산소원자가 결합한 치환기로서, 이의 구체적인 예로는 메톡시, 에톡시, 프로폭시, 이소부틸옥시, sec-부틸옥시, 펜틸옥시, iso-아밀옥시, 헥실옥시, 시클로부틸옥시, 시클로펜틸옥시, 아다만탄옥시, 디시클로펜탄옥시, 보닐옥시, 이소보닐옥시 등을 들 수 있고, 상기 알콕시기 중 하나 이상의 수소 원자는 상기 아릴기의 경우와 마찬가지의 치환기로 치환가능하다.The alkoxy group, which is a substituent used in the compound of the present invention, is a substituent in which an oxygen atom is bonded to the end of an alkyl group or cycloalkyl group, and specific examples thereof include methoxy, ethoxy, propoxy, isobutyloxy, sec-butyloxy, pentyloxy, and iso. -Amyloxy, hexyloxy, cyclobutyloxy, cyclopentyloxy, adamantaneoxy, dicyclopentaneoxy, bornyloxy, isobornyloxy, etc., and at least one hydrogen atom of the alkoxy group is the aryl group. It can be substituted with the same substituent as in the case of.
본 발명의 화합물에서 사용되는 치환기인 아릴알킬기의 구체적인 예로는 페닐메틸(벤질), 페닐에틸, 페닐프로필, 나프틸메틸 나프틸에틸 등을 들 수 있고, 상기 아릴알킬기 중 하나 이상의 수소 원자는 상기 아릴기의 경우와 마찬가지의 치환기로 치환가능하다.Specific examples of the arylalkyl group as a substituent used in the compound of the present invention include phenylmethyl (benzyl), phenylethyl, phenylpropyl, naphthylmethyl naphthylethyl, etc., and at least one hydrogen atom of the arylalkyl group is the arylalkyl group. It can be substituted with the same substituent as in the case of a group.
본 발명의 화합물에서 사용되는 치환기인 알킬아릴기의 구체적인 예로는 톨릴, 자일레닐, 디메틸나프틸, t-부틸페닐, t-부틸나프틸, t-부틸페난트릴 등을 들 수 있고, 상기 알킬아릴기 중 하나 이상의 수소 원자는 상기 아릴기의 경우와 마찬가지의 치환기로 치환가능하다.Specific examples of the alkylaryl group as a substituent used in the compound of the present invention include tolyl, xylenyl, dimethylnaphthyl, t-butylphenyl, t-butylnaphthyl, and t-butylphenanthryl, and the alkyl group One or more hydrogen atoms in the aryl group may be replaced with the same substituent as in the case of the aryl group.
본 발명의 화합물에서 사용되는 치환기인 실릴기의 구체적인 예로는 트리메틸실릴, 트리에틸실릴, 트리페닐실릴, 트리메톡시실릴, 디메톡시페닐실릴, 디페닐메틸실릴, 디페닐비닐실릴, 메틸사이클로뷰틸실릴, 디메틸퓨릴실릴 등을 들 수 있고, 상기 실릴기 중 하나 이상의 수소 원자는 상기 아릴기의 경우와 마찬가지의 치환기로 치환가능 하다.Specific examples of the silyl group as a substituent used in the compound of the present invention include trimethylsilyl, triethylsilyl, triphenylsilyl, trimethoxysilyl, dimethoxyphenylsilyl, diphenylmethylsilyl, diphenylvinylsilyl, and methylcyclobutylsilyl. , dimethylfurylsilyl, etc., and one or more hydrogen atoms of the silyl group may be replaced with the same substituent as that of the aryl group.
또한, 본 발명에서 알케닐(alkenyl)기는 두 개의 탄소원자에 의해 이루어지는 하나의 탄소-탄소 이중 결합을 포함하는 알킬 치환기를 의미하며, 또한 알키닐(alkynyl)기는 두 개의 탄소원자에 의해 이루어지는 하나의 탄소-탄소 삼중 결합을 포함하는 알킬 치환기를 의미한다.In addition, in the present invention, an alkenyl group refers to an alkyl substituent containing one carbon-carbon double bond made up of two carbon atoms, and an alkynyl group means one made up of two carbon atoms. It refers to an alkyl substituent containing a carbon-carbon triple bond.
또한, 본 발명에서 사용되는 알킬렌(alkylene)기는 직쇄형 또는 분지형 형태의 포화탄화수소인 알칸(alkane) 분자내 두 개의 수소 제거에 의하여 유도된 유기 라디칼로, 상기 알킬렌기의 구체적인 예로는 메틸렌기, 에틸렌기, 프로필렌기, 이소프로필렌기, 이소부틸렌기, sec-부틸렌기, tert-부틸렌기, 펜틸렌기, iso-아밀렌기, 헥실렌기 등을 들 수 있고, 상기 알킬렌기 중 하나 이상의 수소 원자는 원자는 상기 아릴기의 경우와 마찬가지의 치환기로 치환가능하다.In addition, the alkylene group used in the present invention is an organic radical derived by removing two hydrogens in an alkane molecule, which is a straight-chain or branched saturated hydrocarbon. Specific examples of the alkylene group include methylene group. , ethylene group, propylene group, isopropylene group, isobutylene group, sec-butylene group, tert-butylene group, pentylene group, iso-amylene group, hexylene group, etc., and hydrogen at least one of the alkylene groups Atoms can be substituted with the same substituents as in the case of the aryl group above.
또한 본 발명에서 디아릴아미노기는 상기 기재된 동일하거나 상이한 두 개의 아릴기가 질소원자에 결합된 아민기를 의미하며, 또한 본 발명에서 디헤테로아릴아미노기는 동일하거나 상이한 두 개의 헤테로아릴기가 질소원자에 결합된 아민기를 의미하고, 또한, 상기 아릴(헤테로아릴)아미노기는 상기 아릴기와 헤테로아릴기가 각각 질소원자에 결합된 아민기를 의미한다.In addition, in the present invention, diarylamino group refers to an amine group in which two identical or different aryl groups described above are bonded to a nitrogen atom, and diheteroarylamino group in the present invention refers to an amine group in which two identical or different heteroaryl groups are bonded to a nitrogen atom. The aryl (heteroaryl) amino group refers to an amine group in which the aryl group and the heteroaryl group are each bonded to a nitrogen atom.
한편, 상기 [화학식 A] 및 [화학식 B] 내 상기 '치환 또는 비치환된'에서의 '치환' 대한 보다 바람직한 예로서, 이는 중수소, 시아노기, 할로겐기, 히드록시기, 니트로기, 탄소수 1 내지 12의 알킬기, 탄소수 1 내지 12의 할로겐화된 알킬기, 탄소수 2 내지 12의 알케닐기, 탄소수 2 내지 12의 알키닐기, 탄소수 3 내지 12의 시클로알킬기, 탄소수 1 내지 12의 헤테로알킬기, 탄소수 6 내지 18의 아릴기, 탄소수 7 내지 20의 아릴알킬기, 탄소수 7 내지 20의 알킬아릴기, 탄소수 2 내지 18의 헤테로아릴기, 탄소수 3 내지 18의 헤테로아릴알킬기, 탄소수 3 내지 18의 알킬헤테로아릴기, 탄소수 9 내지 20의, 방향족 탄화수소 고리가 축합된 시클로알킬기, 탄소수 7 내지 20의, 방향족 헤테로 고리가 축합된 시클로알킬기, 탄소수 9 내지 20의, 방향족 탄화수소 고리가 축합된 헤테로시클로알킬기, 탄소수 9 내지 20의, 지방족 탄화수소 고리가 축합된 아릴기, 탄소수 7 내지 20의, 지방족 탄화수소 고리가 축합된 헤테로아릴기, 탄소수 1 내지 12의 알콕시기, 탄소수 1 내지 18의 아민기, 탄소수 1 내지 18의 실릴기, 탄소수 1 내지 18의 저마늄기, 탄소수 6 내지 18의 아릴옥시기, 탄소수 6 내지 18의 아릴티오닐기로 이루어진 군에서 선택된 1개 이상의 치환기로 치환되는 것일 수 있고, 상기 각각의 치환기내 하나 이상의 수소는 중수소로 치환가능하다.On the other hand, as a more preferable example of 'substitution' in 'substituted or unsubstituted' in [Formula A] and [Formula B], this is deuterium, cyano group, halogen group, hydroxy group, nitro group, carbon number 1 to 12 alkyl group, halogenated alkyl group with 1 to 12 carbon atoms, alkenyl group with 2 to 12 carbon atoms, alkynyl group with 2 to 12 carbon atoms, cycloalkyl group with 3 to 12 carbon atoms, heteroalkyl group with 1 to 12 carbon atoms, aryl with 6 to 18 carbon atoms group, arylalkyl group with 7 to 20 carbon atoms, alkylaryl group with 7 to 20 carbon atoms, heteroaryl group with 2 to 18 carbon atoms, heteroarylalkyl group with 3 to 18 carbon atoms, alkylheteroaryl group with 3 to 18 carbon atoms, 9 to 9 carbon atoms 20, a cycloalkyl group in which an aromatic hydrocarbon ring is condensed, a cycloalkyl group in which an aromatic heterocycle is condensed, having 7 to 20 carbon atoms, a heterocycloalkyl group in which an aromatic hydrocarbon ring is condensed, having 9 to 20 carbon atoms, and aliphatic, having 9 to 20 carbon atoms. Aryl group in which a hydrocarbon ring is condensed, a heteroaryl group in which an aliphatic hydrocarbon ring having 7 to 20 carbon atoms is condensed, An alkoxy group with 1 to 12 carbon atoms, an amine group with 1 to 18 carbon atoms, a silyl group with 1 to 18 carbon atoms, a germanium group with 1 to 18 carbon atoms, an aryloxy group with 6 to 18 carbon atoms, and an arylthionyl group with 6 to 18 carbon atoms. It may be substituted with one or more substituents selected from the group consisting of, and one or more hydrogens in each substituent may be replaced with deuterium.
또한, 본 발명에서, 상기 치환 또는 비치환된 탄소수 7 내지 30의, 방향족 탄화수소 고리가 축합된 시클로알킬기의 보다 바람직한 예로서, 이는 치환 또는 비치환된 탄소수 9 내지 20의, 방향족 탄화수소 고리가 축합된 시클로알킬기일 수 있다. In addition, in the present invention, as a more preferred example of the cycloalkyl group in which a substituted or unsubstituted aromatic hydrocarbon ring having 7 to 30 carbon atoms is condensed, it is a cycloalkyl group in which a substituted or unsubstituted aromatic hydrocarbon ring having 9 to 20 carbon atoms is condensed. It may be a cycloalkyl group.
또한, 본 발명에서, 상기 치환 또는 비치환된 탄소수 5 내지 30의, 방향족 헤테로고리가 축합된 시클로알킬기의 보다 바람직한 예로서, 이는 치환 또는 비치환된 탄소수 7 내지 20의, 방향족 헤테로 고리가 축합된 시클로알킬기일 수 있다.In addition, in the present invention, as a more preferred example of the cycloalkyl group in which a substituted or unsubstituted aromatic heterocycle having 5 to 30 carbon atoms is condensed, it is a cycloalkyl group in which a substituted or unsubstituted aromatic heteroring having 7 to 20 carbon atoms is condensed. It may be a cycloalkyl group.
또한, 본 발명에서, 상기 치환 또는 비치환된 탄소수 6 내지 30의, 방향족 탄화수소 고리가 축합된 헤테로시클로알킬기의 보다 바람직한 예로서, 이는 치환 또는 비치환된 탄소수 9 내지 20의, 방향족 탄화수소 고리가 축합된 헤테로시클로알킬기일 수 있다.In addition, in the present invention, the substituted or unsubstituted carbon number is 6 As a more preferable example of a heterocycloalkyl group in which a 30 to 30 aromatic hydrocarbon ring is condensed, it may be a substituted or unsubstituted heterocycloalkyl group in which a 9 to 20 carbon atom aromatic hydrocarbon ring is condensed.
또한, 본 발명에서, 상기 치환 또는 비치환된 탄소수 8 내지 30의, 지방족 탄화수소 고리가 축합된 아릴기의 보다 바람직한 예로서, 이는 치환 또는 비치환된 탄소수 9 내지 20의, 지방족 탄화수소 고리가 축합된 아릴기일 수 있다.In addition, in the present invention, as a more preferred example of the aryl group in which a substituted or unsubstituted aliphatic hydrocarbon ring having 8 to 30 carbon atoms is condensed, it is an aryl group in which a substituted or unsubstituted aliphatic hydrocarbon ring having 9 to 20 carbon atoms is condensed. It may be an aryl group.
또한, 본 발명에서, 상기 치환 또는 비치환된 탄소수 5 내지 30의, 지방족 탄화수소 고리가 축합된 헤테로아릴기의 보다 바람직한 예로서, 이는 치환 또는 비치환된 탄소수 7 내지 20의, 지방족 탄화수소 고리가 축합된 헤테로아릴기일 수 있다.In addition, in the present invention, as a more preferred example of the heteroaryl group in which the substituted or unsubstituted aliphatic hydrocarbon ring having 5 to 30 carbon atoms is condensed, it is a substituted or unsubstituted heteroaryl group having 7 to 20 carbon atoms in which the aliphatic hydrocarbon ring is condensed. It may be a heteroaryl group.
또한, 본 발명에서, 상기 치환 또는 비치환된 탄소수 6 내지 30의, 지방족 헤테로 고리가 축합된 아릴기의 보다 바람직한 예로서, 이는 치환 또는 비치환된 탄소수 7 내지 20의, 지방족 헤테로 고리가 축합된 아릴기일 수 있다.In addition, in the present invention, as a more preferable example of an aryl group in which a substituted or unsubstituted aliphatic heterocycle having 6 to 30 carbon atoms is condensed, it is an aryl group in which a substituted or unsubstituted aliphatic heteroring having 7 to 20 carbon atoms is condensed. It may be an aryl group.
또한, 본 발명에서, 상기 치환 또는 비치환된 탄소수 5 내지 30의, 지방족 헤테로 고리가 축합된 헤테로아릴기의 보다 바람직한 예로서, 이는 치환 또는 비치환된 탄소수 6 내지 20의, 지방족 헤테로 고리가 축합된 헤테로아릴기일 수 있다.In addition, in the present invention, as a more preferred example of a heteroaryl group in which a substituted or unsubstituted aliphatic heterocycle having 5 to 30 carbon atoms is condensed, it is a group in which a substituted or unsubstituted aliphatic heteroring having 6 to 20 carbon atoms is condensed. It may be a heteroaryl group.
한편, 본 발명에서, 상기 'R2 및 R3 는 서로 연결되어 지환족 또는 방향족의 단일환 또는 다환고리를 추가적으로 형성할 수 있으며'의 경우에 이는 상기 R2와 R3 각각으로부터 하나의 수소라디칼을 제거하고 이들을 연결함으로써 추가적으로 고리를 형성할 수 있는 것을 의미한다. Meanwhile, in the present invention, in the case of 'R 2 and R 3 may be connected to each other to additionally form an alicyclic or aromatic single or polycyclic ring', this means that one hydrogen radical from each of R 2 and R 3 This means that an additional ring can be formed by removing and connecting them.
본 발명에 있어서 상기 [화학식 A] 또는 [화학식 B]로 표시되는 방향족 헤테로고리 화합물은 상기 Z1 내지 Z8을 포함하는 페난트렌 유사 고리에 상기 X1 및 질소원자(N)를 포함하는 방향족 헤테로 오각 고리가 축합된 모핵구조를 가지되, 상기 방향족 헤테로 오각 고리내 X1 및 질소원자(N)에 결합된 방향족 탄소원자에 치환기 R1이 결합하고, 상기 페난트렌 유사 고리의 말단 방향족 육각 고리내 Z3 내지 Z6 중 하나는 아민 치환기(
Figure PCTKR2023003724-appb-img-000005
)내 연결기 L과 결합하는 단일결합을 포함하는 탄소원자인 것을 기술적 특징으로 한다.In the present invention, the aromatic heterocyclic compound represented by [Formula A] or [Formula B] is an aromatic heterocyclic compound containing X 1 and a nitrogen atom (N) in a phenanthrene-like ring containing Z 1 to Z 8 It has a parent core structure in which a pentagonal ring is condensed, and a substituent R 1 is bonded to the aromatic carbon atom bonded to One of Z 3 to Z 6 is an amine substituent (
Figure PCTKR2023003724-appb-img-000005
) has a technical characteristic of being a carbon atom containing a single bond bonded to the linking group L.
[화학식 A] [Formula A]
Figure PCTKR2023003724-appb-img-000006
Figure PCTKR2023003724-appb-img-000006
[화학식 B] [Formula B]
Figure PCTKR2023003724-appb-img-000007
Figure PCTKR2023003724-appb-img-000007
본 발명의 일 실시예로서, 상기 화학식 A 및 화학식 B내 X1은 O 또는 S일 수 있다.As an example of the present invention, X 1 in Formula A and Formula B may be O or S.
본 발명의 일 실시예로서, 상기 화학식 A 및 화학식 B내 상기 R1 내지 R4는 바람직하게는, 서로 동일하거나 상이하며, 각각 독립적으로 수소, 중수소, 치환 또는 비치환된 탄소수 1 내지 10의 알킬기, 치환 또는 비치환된 탄소수 6 내지 20의 아릴기, 치환 또는 비치환된 탄소수 3 내지 30의 시클로알킬기, 치환 또는 비치환된 탄소수 2 내지 20의 헤테로아릴기 중에서 선택되는 어느 하나일 수 있다.As an embodiment of the present invention, R 1 to R 4 in Formula A and Formula B are preferably the same as or different from each other, and are each independently hydrogen, deuterium, or a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms. , a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 20 carbon atoms.
본 발명의 일 실시예로서, 상기 화학식 A 및 화학식 B내 상기 R1 내지 R3 중 적어도 하나는 탄소수 6 내지 24의 아릴기일 수 있고, 더욱 바람직하게는, 상기 R1 내지 R3 중 적어도 하나는 아래 구조식 1 내지 구조식 6 중에서 선택되는 어느 하나일 수 있다. As an embodiment of the present invention, at least one of R 1 to R 3 in Formula A and Formula B may be an aryl group having 6 to 24 carbon atoms, and more preferably, at least one of R 1 to R 3 is It may be any one selected from Structural Formulas 1 to 6 below.
[구조식 1] [구조식 2] [구조식 3] [Structural Formula 1] [Structural Formula 2] [Structural Formula 3]
Figure PCTKR2023003724-appb-img-000008
Figure PCTKR2023003724-appb-img-000008
[구조식 4] [구조식 5] [구조식 6][Structural Formula 4] [Structural Formula 5] [Structural Formula 6]
Figure PCTKR2023003724-appb-img-000009
Figure PCTKR2023003724-appb-img-000009
상기 구조식 6에서, 상기 Z는 NR5, CR6R7, O 및 S 중에서 선택되는 어느 하나이고,In structural formula 6, Z is any one selected from NR 5 , CR 6 R 7 , O and S,
상기 R5 내지 R7은 상기 R1 내지 R4와 동일하고,R 5 to R 7 are the same as R 1 to R 4 ,
상기 구조식 1 내지 6에서 방향족 고리의 탄소자리는 수소, 중수소, 탄소수 1 내지 10의 알킬기, 탄소수 6 내지 18의 아릴기 중에서 선택되는 어느 하나 이상이 결합될 수 있다.In the structural formulas 1 to 6, the carbon site of the aromatic ring may be bonded to one or more selected from hydrogen, deuterium, an alkyl group having 1 to 10 carbon atoms, and an aryl group having 6 to 18 carbon atoms.
또한 본 발명의 일 실시예로서, 상기 방향족 헤테로고리 화합물내 R1 내지 R3 중 적어도 하나는 아래의 [구조식 A]로 표시되는 치환기일 수 있다. Additionally, as an example of the present invention, at least one of R 1 to R 3 in the aromatic heterocyclic compound may be a substituent represented by [Structural Formula A] below.
[구조식 A][Structural Formula A]
Figure PCTKR2023003724-appb-img-000010
Figure PCTKR2023003724-appb-img-000010
[구조식 Q-1] [구조식 Q-2] [구조식 Q-3][Structural formula Q-1] [Structural formula Q-2] [Structural formula Q-3]
Figure PCTKR2023003724-appb-img-000011
Figure PCTKR2023003724-appb-img-000011
상기 [구조식 A]에서,In the above [structural formula A],
상기 Q는 아래의 구조식 Q-1 내지 Q-3 중에서 선택되는 어느 하나의 고리이고,Wherein Q is any one ring selected from the structural formulas Q-1 to Q-3 below,
상기 Q가 구조식 Q-1인 경우, 상기 구조식 Q-1 내 이웃한 탄소 원자인 R17과 R18, R18과 R19 및 R19와 R20 중 한 쌍의 치환기는 구조식 A 내 방향족 탄소원자 f 및 방향족 탄소원자 g와 축합되어 6원환의 고리를 형성하는 단일결합이고,When Q is structural formula Q-1, a pair of substituents among the neighboring carbon atoms R 17 and R 18 , R 18 and R 19 , and R 19 and R 20 in structural formula Q-1 are aromatic carbon atoms in structural formula A. It is a single bond that is condensed with f and the aromatic carbon atom g to form a 6-membered ring,
상기 Q가 구조식 Q-2 인 경우, 상기 구조식 Q-2 내 이웃한 탄소 원자인 R25와 R26, R27과 R28, R28과 R29 및 R29와 R30 중 한 쌍의 치환기는 구조식 A 내 방향족 탄소원자 f 및 방향족 탄소원자 g와 축합되어 6원환의 고리를 형성하는 단일결합이며, When Q is the structural formula Q-2, a pair of substituents among the neighboring carbon atoms in the structural formula Q-2, R 25 and R 26 , R 27 and R 28 , R 28 and R 29 , and R 29 and R 30 It is a single bond that is condensed with the aromatic carbon atom f and the aromatic carbon atom g in structural formula A to form a six-membered ring,
상기 Q가 구조식 Q-3인 경우, 상기 구조식 Q-3 내 이웃한 탄소 원자인 R35와 R36, R36과 R37 및 R37과 R38 중 한 쌍의 치환기는 구조식 A 내 방향족 탄소원자 f 및 방향족 탄소원자 g와 축합되어 6원환의 고리를 형성하는 단일결합이며, When Q is structural formula Q-3, a pair of substituents among the neighboring carbon atoms R 35 and R 36 , R 36 and R 37 , and R 37 and R 38 in structural formula Q-3 are aromatic carbon atoms in structural formula A. It is a single bond that is condensed with f and the aromatic carbon atom g to form a 6-membered ring,
상기 치환기 R11 내지 R16 및, R17 내지 R44 중 고리를 형성하는 단일결합이 아닌 나머지 치환기는 서로 동일하거나 상이하며, 각각 독립적으로 수소, 중수소, 중수소 치환되거나 비치환된 탄소수 1 내지 24의 알킬기, 중수소 치환되거나 비치환된 탄소수 1 내지 24의 할로겐화된 알킬기, 중수소 치환되거나 비치환된 탄소수 3 내지 30의 시클로알킬기, 중수소 치환되거나 비치환된 탄소수 2 내지 24의 알케닐기, 중수소 치환되거나 비치환된 탄소수 2 내지 24의 알키닐기, 중수소 치환되거나 비치환된 탄소수 1 내지 24의 헤테로알킬기, 중수소 치환되거나 비치환된 탄소수 6 내지 24의 아릴기, 중수소 치환되거나 비치환된 탄소수 7 내지 24의 아릴알킬기, 중수소 치환되거나 비치환된 탄소수 7 내지 24의 알킬아릴기, 중수소 치환되거나 비치환된 탄소수 2 내지 24의 헤테로아릴기, 중수소 치환되거나 비치환된 탄소수 2 내지 24의 헤테로아릴알킬기, 중수소 치환되거나 비치환된 탄소수 7 내지 24의, 방향족 탄화수소 고리가 축합된 시클로알킬기, 중수소 치환되거나 비치환된 탄소수 5 내지 24의, 방향족 헤테로고리가 축합된 시클로알킬기, 중수소 치환되거나 비치환된 탄소수 6 내지 24의, 방향족 탄화수소 고리가 축합된 헤테로시클로알킬기, 중수소 치환되거나 비치환된 탄소수 8 내지 24의, 지방족 탄화수소 고리가 축합된 아릴기, 중수소 치환되거나 비치환된 탄소수 5 내지 24의, 지방족 탄화수소 고리가 축합된 헤테로아릴기, 중수소 치환되거나 비치환된 탄소수 1 내지 24의 알콕시기, 중수소 치환되거나 비치환된 탄소수 1 내지 24의 아민기, 중수소 치환되거나 비치환된 탄소수 1 내지 24의 실릴기, 중수소 치환되거나 비치환된 탄소수 1 내지 24의 저마늄기, 중수소 치환되거나 비치환된 탄소수 6 내지 24의 아릴옥시기, 중수소 치환되거나 비치환된 탄소수 6 내지 24의 아릴티오닐기 중에서 선택되는 어느 하나이되,Among the substituents R 11 to R 16 and R 17 to R 44 , the remaining substituents that are not a single bond forming a ring are the same or different from each other, and each independently represents hydrogen, deuterium, deuterium, substituted or unsubstituted carbon atoms of 1 to 24. Alkyl group, deuterated or unsubstituted halogenated alkyl group having 1 to 24 carbon atoms, deuterated or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, deuterated or unsubstituted alkenyl group having 2 to 24 carbon atoms, deuterium substituted or unsubstituted Alkynyl group having 2 to 24 carbon atoms, deuterated or unsubstituted heteroalkyl group having 1 to 24 carbon atoms, deuterated or unsubstituted aryl group having 6 to 24 carbon atoms, deuterium substituted or unsubstituted arylalkyl group having 7 to 24 carbon atoms , deuterium substituted or unsubstituted alkylaryl group having 7 to 24 carbon atoms, deuterium substituted or unsubstituted heteroaryl group having 2 to 24 carbon atoms, deuterium substituted or unsubstituted heteroarylalkyl group having 2 to 24 carbon atoms, deuterated or unsubstituted A cycloalkyl group in which a ringed C7-C24 aromatic hydrocarbon ring is condensed, a deuterium-substituted or unsubstituted C5-C24 aromatic heterocycle-condensed cycloalkyl group, a deuterium-substituted or unsubstituted C6-C24 ring, Heterocycloalkyl group in which an aromatic hydrocarbon ring is condensed, an aryl group in which a deuterium-substituted or unsubstituted aliphatic hydrocarbon ring having 8 to 24 carbon atoms is condensed, a hetero group in which a deuterium-substituted or unsubstituted aliphatic hydrocarbon ring is condensed in 5 to 24 carbon atoms. Aryl group, deuterium-substituted or unsubstituted alkoxy group of 1 to 24 carbon atoms, deuterium-substituted or unsubstituted amine group of 1 to 24 carbon atoms, deuterium-substituted or unsubstituted silyl group of 1 to 24 carbon atoms, deuterium-substituted or unsubstituted Any one selected from the group consisting of a germanium group having 1 to 24 carbon atoms, a deuterium-substituted or unsubstituted aryloxy group having 6 to 24 carbon atoms, and a deuterium-substituted or unsubstituted arylthionyl group having 6 to 24 carbon atoms,
상기 구조식 A내 Q가 구조식 Q-1인 경우, 구조식 A내 R11 내지 R16 중 하나, 또는 구조식 Q-1내 R17 내지 R24 중 하나는 R1 내지 R3 와 결합되는 탄소원자 또는 질소원자에 결합되는 단일 결합이고, When Q in the structural formula A is structural formula Q-1, one of R 11 to R 16 in the structural formula A, or Within structural formula Q-1 One of R 17 to R 24 is a single bond bonded to the carbon atom or nitrogen atom bonded to R 1 to R 3 ,
상기 구조식 A내 Q가 구조식 Q-2인 경우, 구조식 A내 R11 내지 R16 중 하나, 또는 구조식 Q-2내 R25 내지 R34 중 하나는 R1 내지 R3 와 결합되는 탄소원자 또는 질소원자에 결합되는 단일 결합이며, When Q in the structural formula A is structural formula Q-2, one of R 11 to R 16 in the structural formula A, or Within structural formula Q-2 One of R 25 to R 34 is a single bond bonded to the carbon atom or nitrogen atom bonded to R 1 to R 3 ,
상기 구조식 A내 Q가 구조식 Q-3인 경우, 구조식 A내 R11 내지 R16 중 하나, 또는 구조식 Q-3내 R35 내지 R42 중 하나는 R1 내지 R3 와 결합되는 탄소원자 또는 질소원자에 결합되는 단일 결합이고,When Q in the structural formula A is structural formula Q-3, one of R 11 to R 16 in the structural formula A, or Within structural formula Q-3 One of R 35 to R 42 is a single bond bonded to the carbon atom or nitrogen atom bonded to R 1 to R 3 ,
상기 R43 및 R44는 서로 연결되어 지환족 또는 방향족의 단일환 또는 다환의 고리를 추가 형성할 수 있다.R 43 and R 44 may be connected to each other to further form an alicyclic or aromatic monocyclic or polycyclic ring.
여기서 상기 상기 구조식 A내 Q가 구조식 Q-1 내지 Q-3에 해당하는 경우 상기 구조식 A의 구조를 보충하여 설명하면, 상기 구조식 A내 Q가 구조식 Q-1인 경우, 상기 구조식 Q-1내 치환기 R17과 R18, 치환기 R18과 R19, 및 치환기 R19와 R20 중 하나의 서로 인접한 치환기들(서로 인접한 두 개의 치환기)은 구조식 A 내 R11 및 R12를 포함하는 6원환의 방향족고리와 상기 구조식 Q-1내 방향족 고리가 2개의 탄소원자를 공유하는 축합고리를 형성하기 위한 방향족 탄소원자들 간의 결합(bonding)에 해당하며, 또한, 상기 Q가 구조식 Q-2인 경우, 상기 구조식 Q-2 내 치환기 R25과 R26, 치환기 R27과 R28, 치환기 R28과 R29, 및 치환기 R29와 R30 중 하나의 서로 인접한 치환기들(서로 인접한 두 개의 치환기)은 구조식 A 내 R11 및 R12를 포함하는 6원환의 방향족고리와 상기 구조식 Q-2내 방향족 고리가 2개의 탄소원자를 공유하는 축합고리를 형성하기 위한 방향족 탄소원자들 간의 결합(bonding)에 해당하고, 또한, 상기 Q가 구조식 Q-3인 경우, 상기 구조식 Q-3 내 치환기 R35과 R36, 치환기 R36과 R37, 및 치환기 R37와 R38 중 하나의 서로 인접한 치환기들(서로 인접한 두 개의 치환기)은 구조식 A 내 R11 및 R12를 포함하는 6원환의 방향족고리와 상기 구조식 Q-3내 방향족 고리가 2개의 탄소원자를 공유하는 축합고리를 형성하기 위한 방향족 탄소원자들 간의 결합(bonding)에 해당한다. Here, if Q in the structural formula A corresponds to structural formulas Q-1 to Q-3, the structure of structural formula A will be supplemented and explained. If Q in structural formula A is structural formula Q-1, then Q in structural formula A corresponds to structural formula Q-1. One of the substituents R 17 and R 18 , the substituents R 18 and R 19 , and the substituents R 19 and R 20 are adjacent to each other (two substituents adjacent to each other) of a 6-membered ring containing R 11 and R 12 in structural formula A. Corresponds to bonding between aromatic rings and aromatic carbon atoms to form a condensed ring in which the aromatic ring in the structural formula Q-1 shares two carbon atoms, and when Q is structural formula Q-2, In structural formula Q-2, one of the substituents R 25 and R 26, the substituents R 27 and R 28, the substituents R 28 and R 29, and the substituents R 29 and R 30 that are adjacent to each other (two substituents adjacent to each other) are represented by structural formula A Corresponds to a bonding between aromatic carbon atoms to form a condensed ring in which the aromatic ring of the 6-membered ring containing R 11 and R 12 and the aromatic ring in the structural formula Q-2 share two carbon atoms, and , when Q is the structural formula Q-3, one of the substituents R 35 and R 36, the substituents R 36 and R 37, and the substituents R 37 and R 38 in the structural formula Q-3 are adjacent to each other (two adjacent to each other Substituent) is a bond between aromatic carbon atoms to form a condensed ring in which the 6-membered aromatic ring containing R 11 and R 12 in structural formula A and the aromatic ring in structural formula Q-3 share two carbon atoms. corresponds to
본 발명에 따른 상기 [구조식 A]로 표시되는 치환기의 구체적 예로서, 이는 하기 [구조식 A-1] 내지 [구조식 A-15] 중에서 선택되는 어느 하나의 치환기일 수 있다.As a specific example of the substituent represented by [Structural Formula A] according to the present invention, it may be any one of the substituents selected from the following [Structural Formula A-1] to [Structural Formula A-15].
[구조식 A-1] [구조식 A-2][Structural Formula A-1] [Structural Formula A-2]
Figure PCTKR2023003724-appb-img-000012
Figure PCTKR2023003724-appb-img-000012
[구조식 A-3] [구조식 A-4][Structural Formula A-3] [Structural Formula A-4]
Figure PCTKR2023003724-appb-img-000013
Figure PCTKR2023003724-appb-img-000013
[구조식 A-5] [구조식 A-6][Structural Formula A-5] [Structural Formula A-6]
Figure PCTKR2023003724-appb-img-000014
Figure PCTKR2023003724-appb-img-000014
[구조식 A-7] [구조식 A-8][Structural Formula A-7] [Structural Formula A-8]
Figure PCTKR2023003724-appb-img-000015
Figure PCTKR2023003724-appb-img-000015
[구조식 A-9] [구조식 A-10][Structural Formula A-9] [Structural Formula A-10]
Figure PCTKR2023003724-appb-img-000016
Figure PCTKR2023003724-appb-img-000016
[구조식 A-11] [구조식 A-12][Structural Formula A-11] [Structural Formula A-12]
Figure PCTKR2023003724-appb-img-000017
Figure PCTKR2023003724-appb-img-000017
[구조식 A-13] [구조식 A-14][Structural Formula A-13] [Structural Formula A-14]
Figure PCTKR2023003724-appb-img-000018
Figure PCTKR2023003724-appb-img-000018
[구조식 A-15][Structural Formula A-15]
Figure PCTKR2023003724-appb-img-000019
Figure PCTKR2023003724-appb-img-000019
여기서, 상기 [구조식 A-1] 내지 [구조식 A-15]내 치환기 R11 내지 R44는 앞에서 정의한 바와 동일하다.Here, the substituents R 11 to R 44 in [Structural Formula A-1] to [Structural Formula A-15] are the same as previously defined.
또한 본 발명의 일 실시예로서, 상기 [화학식 A] 및 [화학식 B] 내 R1 내지 R3 중 적어도 하나는 상기 [구조식 A]로 표시되는 치환기일 수 있으며, 더욱 바람직하게는, R2 만이 [구조식 A]로 표시되는 치환기이거나, 또는 R3 만이 [구조식 A]로 표시되는 치환기일 수 있다.In addition, as an embodiment of the present invention, at least one of R 1 to R 3 in [Formula A] and [Formula B] may be a substituent represented by [Structural Formula A], and more preferably, only R 2 It may be a substituent represented by [structural formula A], or only R 3 may be a substituent represented by [structural formula A].
또한 본 발명의 일 실시예로서, 상기 화학식 A 및 화학식 B내 치환기 R1은 치환 또는 비치환된 페닐기, 치환 또는 비치환된 나프틸기, 치환 또는 비치환된 페난트릴기 중에서 선택되는 어느 하나일 수 있다.In addition, as an embodiment of the present invention, the substituent R 1 in Formula A and Formula B may be any one selected from a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, and a substituted or unsubstituted phenanthryl group. there is.
또한 본 발명의 상기 [화학식 A] 또는 [화학식 B]로 표시되는 방향족 헤테로고리 화합물의 구체적 예시로서, 이는 아래의 <1> 내지 <240> 중에서 선택되는 어느 하나의 화합물일 수 있으나, 이에 제한되지 않는다. Additionally, as a specific example of the aromatic heterocyclic compound represented by [Formula A] or [Formula B] of the present invention, it may be any one compound selected from <1> to <240> below, but is not limited thereto. No.
Figure PCTKR2023003724-appb-img-000020
Figure PCTKR2023003724-appb-img-000020
1 2 31 2 3
Figure PCTKR2023003724-appb-img-000021
Figure PCTKR2023003724-appb-img-000021
4 5 64 5 6
Figure PCTKR2023003724-appb-img-000022
Figure PCTKR2023003724-appb-img-000022
7 8 97 8 9
Figure PCTKR2023003724-appb-img-000023
Figure PCTKR2023003724-appb-img-000023
10 11 1210 11 12
Figure PCTKR2023003724-appb-img-000024
Figure PCTKR2023003724-appb-img-000024
13 14 1513 14 15
Figure PCTKR2023003724-appb-img-000025
Figure PCTKR2023003724-appb-img-000025
16 17 1816 17 18
Figure PCTKR2023003724-appb-img-000026
Figure PCTKR2023003724-appb-img-000026
19 20 2119 20 21
Figure PCTKR2023003724-appb-img-000027
Figure PCTKR2023003724-appb-img-000027
22 23 2422 23 24
Figure PCTKR2023003724-appb-img-000028
Figure PCTKR2023003724-appb-img-000028
25 26 2725 26 27
Figure PCTKR2023003724-appb-img-000029
Figure PCTKR2023003724-appb-img-000029
28 29 3028 29 30
Figure PCTKR2023003724-appb-img-000030
Figure PCTKR2023003724-appb-img-000030
31 32 3331 32 33
Figure PCTKR2023003724-appb-img-000031
Figure PCTKR2023003724-appb-img-000031
34 35 3634 35 36
Figure PCTKR2023003724-appb-img-000032
Figure PCTKR2023003724-appb-img-000032
37 38 3937 38 39
Figure PCTKR2023003724-appb-img-000033
Figure PCTKR2023003724-appb-img-000033
40 41 4240 41 42
Figure PCTKR2023003724-appb-img-000034
Figure PCTKR2023003724-appb-img-000034
43 44 4543 44 45
Figure PCTKR2023003724-appb-img-000035
Figure PCTKR2023003724-appb-img-000035
46 47 4846 47 48
Figure PCTKR2023003724-appb-img-000036
Figure PCTKR2023003724-appb-img-000036
49 50 5149 50 51
Figure PCTKR2023003724-appb-img-000037
Figure PCTKR2023003724-appb-img-000037
52 53 5452 53 54
Figure PCTKR2023003724-appb-img-000038
Figure PCTKR2023003724-appb-img-000038
55 56 5755 56 57
Figure PCTKR2023003724-appb-img-000039
Figure PCTKR2023003724-appb-img-000039
58 59 6058 59 60
Figure PCTKR2023003724-appb-img-000040
Figure PCTKR2023003724-appb-img-000040
61 62 6361 62 63
Figure PCTKR2023003724-appb-img-000041
Figure PCTKR2023003724-appb-img-000041
64 65 6664 65 66
Figure PCTKR2023003724-appb-img-000042
Figure PCTKR2023003724-appb-img-000042
67 68 6967 68 69
Figure PCTKR2023003724-appb-img-000043
Figure PCTKR2023003724-appb-img-000043
70 71 7270 71 72
Figure PCTKR2023003724-appb-img-000044
Figure PCTKR2023003724-appb-img-000044
73 74 7573 74 75
Figure PCTKR2023003724-appb-img-000045
Figure PCTKR2023003724-appb-img-000045
76 77 7876 77 78
Figure PCTKR2023003724-appb-img-000046
Figure PCTKR2023003724-appb-img-000046
79 80 8179 80 81
Figure PCTKR2023003724-appb-img-000047
Figure PCTKR2023003724-appb-img-000047
82 83 8482 83 84
Figure PCTKR2023003724-appb-img-000048
Figure PCTKR2023003724-appb-img-000048
85 86 8785 86 87
Figure PCTKR2023003724-appb-img-000049
Figure PCTKR2023003724-appb-img-000049
88 89 9088 89 90
Figure PCTKR2023003724-appb-img-000050
Figure PCTKR2023003724-appb-img-000050
91 92 9391 92 93
Figure PCTKR2023003724-appb-img-000051
Figure PCTKR2023003724-appb-img-000051
94 95 9694 95 96
Figure PCTKR2023003724-appb-img-000052
Figure PCTKR2023003724-appb-img-000052
97 98 9997 98 99
Figure PCTKR2023003724-appb-img-000053
Figure PCTKR2023003724-appb-img-000053
100 101 102100 101 102
Figure PCTKR2023003724-appb-img-000054
Figure PCTKR2023003724-appb-img-000054
103 104 105103 104 105
Figure PCTKR2023003724-appb-img-000055
Figure PCTKR2023003724-appb-img-000055
106 107 108106 107 108
Figure PCTKR2023003724-appb-img-000056
Figure PCTKR2023003724-appb-img-000056
109 110 111109 110 111
Figure PCTKR2023003724-appb-img-000057
Figure PCTKR2023003724-appb-img-000057
112 113 114112 113 114
Figure PCTKR2023003724-appb-img-000058
Figure PCTKR2023003724-appb-img-000058
115 116 117115 116 117
Figure PCTKR2023003724-appb-img-000059
Figure PCTKR2023003724-appb-img-000059
118 119 120118 119 120
Figure PCTKR2023003724-appb-img-000060
Figure PCTKR2023003724-appb-img-000060
121 122 123121 122 123
Figure PCTKR2023003724-appb-img-000061
Figure PCTKR2023003724-appb-img-000061
124 125 126124 125 126
Figure PCTKR2023003724-appb-img-000062
Figure PCTKR2023003724-appb-img-000062
127 128 129127 128 129
Figure PCTKR2023003724-appb-img-000063
Figure PCTKR2023003724-appb-img-000063
130 131 132130 131 132
Figure PCTKR2023003724-appb-img-000064
Figure PCTKR2023003724-appb-img-000064
133 134 135133 134 135
Figure PCTKR2023003724-appb-img-000065
Figure PCTKR2023003724-appb-img-000065
136 137 138136 137 138
Figure PCTKR2023003724-appb-img-000066
Figure PCTKR2023003724-appb-img-000066
139 140 141139 140 141
Figure PCTKR2023003724-appb-img-000067
Figure PCTKR2023003724-appb-img-000067
142 143 144142 143 144
Figure PCTKR2023003724-appb-img-000068
Figure PCTKR2023003724-appb-img-000068
145 146 147145 146 147
Figure PCTKR2023003724-appb-img-000069
Figure PCTKR2023003724-appb-img-000069
148 149 150148 149 150
Figure PCTKR2023003724-appb-img-000070
Figure PCTKR2023003724-appb-img-000070
151 152 153151 152 153
Figure PCTKR2023003724-appb-img-000071
Figure PCTKR2023003724-appb-img-000071
154 155 156154 155 156
Figure PCTKR2023003724-appb-img-000072
Figure PCTKR2023003724-appb-img-000072
157 158 159157 158 159
Figure PCTKR2023003724-appb-img-000073
Figure PCTKR2023003724-appb-img-000073
160 161 162160 161 162
Figure PCTKR2023003724-appb-img-000074
Figure PCTKR2023003724-appb-img-000074
163 164 165163 164 165
Figure PCTKR2023003724-appb-img-000075
Figure PCTKR2023003724-appb-img-000075
166 167 168166 167 168
Figure PCTKR2023003724-appb-img-000076
Figure PCTKR2023003724-appb-img-000076
169 170 171169 170 171
Figure PCTKR2023003724-appb-img-000077
Figure PCTKR2023003724-appb-img-000077
172 173 174172 173 174
Figure PCTKR2023003724-appb-img-000078
Figure PCTKR2023003724-appb-img-000078
175 176 177175 176 177
Figure PCTKR2023003724-appb-img-000079
Figure PCTKR2023003724-appb-img-000079
178 179 180178 179 180
Figure PCTKR2023003724-appb-img-000080
Figure PCTKR2023003724-appb-img-000080
181 182 183181 182 183
Figure PCTKR2023003724-appb-img-000081
Figure PCTKR2023003724-appb-img-000081
184 185 186184 185 186
Figure PCTKR2023003724-appb-img-000082
Figure PCTKR2023003724-appb-img-000082
187 188 189187 188 189
Figure PCTKR2023003724-appb-img-000083
Figure PCTKR2023003724-appb-img-000083
190 191 192190 191 192
Figure PCTKR2023003724-appb-img-000084
Figure PCTKR2023003724-appb-img-000084
193 194 195193 194 195
Figure PCTKR2023003724-appb-img-000085
Figure PCTKR2023003724-appb-img-000085
196 197 198196 197 198
Figure PCTKR2023003724-appb-img-000086
Figure PCTKR2023003724-appb-img-000086
199 200 201199 200 201
Figure PCTKR2023003724-appb-img-000087
Figure PCTKR2023003724-appb-img-000087
202 203 204202 203 204
Figure PCTKR2023003724-appb-img-000088
Figure PCTKR2023003724-appb-img-000088
205 206 207205 206 207
Figure PCTKR2023003724-appb-img-000089
Figure PCTKR2023003724-appb-img-000089
208 209 210208 209 210
Figure PCTKR2023003724-appb-img-000090
Figure PCTKR2023003724-appb-img-000090
211 212 213211 212 213
Figure PCTKR2023003724-appb-img-000091
Figure PCTKR2023003724-appb-img-000091
214 215 216214 215 216
Figure PCTKR2023003724-appb-img-000092
Figure PCTKR2023003724-appb-img-000092
217 218 219217 218 219
Figure PCTKR2023003724-appb-img-000093
Figure PCTKR2023003724-appb-img-000093
220 221 222220 221 222
Figure PCTKR2023003724-appb-img-000094
Figure PCTKR2023003724-appb-img-000094
223 224 225223 224 225
Figure PCTKR2023003724-appb-img-000095
Figure PCTKR2023003724-appb-img-000095
226 227 228226 227 228
Figure PCTKR2023003724-appb-img-000096
Figure PCTKR2023003724-appb-img-000096
229 230 231229 230 231
Figure PCTKR2023003724-appb-img-000097
Figure PCTKR2023003724-appb-img-000097
232 233 234232 233 234
Figure PCTKR2023003724-appb-img-000098
Figure PCTKR2023003724-appb-img-000098
235 236 237235 236 237
Figure PCTKR2023003724-appb-img-000099
Figure PCTKR2023003724-appb-img-000099
238 239 240238 239 240
또한, 본 발명은 제1전극; 상기 제1전극에 대향된 제2전극; 및 상기 제1전극과 상기 제2전극 사이에 개재되는 유기층;을 포함하고, 상기 유기층이 본 발명에 따른 상기 [화학식 A] 또는 [화학식 B]로 표시되는 화합물을 1종 이상 포함하는 유기발광소자를 제공하며, 본 발명에 따른 유기발광소자는 저전압 구동, 고효율 및 장수명 특성을 나타낼 수 있다.In addition, the present invention includes a first electrode; a second electrode opposite the first electrode; and an organic layer interposed between the first electrode and the second electrode, wherein the organic layer includes one or more compounds represented by [Formula A] or [Formula B] according to the present invention. Provides that the organic light emitting device according to the present invention can exhibit low voltage driving, high efficiency, and long life characteristics.
한편, 본 발명에서 "(유기층이) 유기 화합물을 1종 이상 포함한다" 란, "(유기층이) 본 발명의 범주에 속하는 1종의 유기 화합물 또는 상기 유기 화합물의 범주에 속하는 서로 다른 2종 이상의 화합물을 포함할 수 있다"로 해석될 수 있다.Meanwhile, in the present invention, “(the organic layer) includes one or more organic compounds” means “(the organic layer) contains one type of organic compound within the scope of the present invention or two or more different types of organic compounds within the scope of the organic compound.” It can be interpreted as “may include compounds.”
이때, 본 발명의 상기 유기발광소자내 유기층은 정공 주입층, 정공 수송층, 정공 주입 기능 및 정공수송 기능을 동시에 갖는 기능층, 발광층, 전자 수송층, 및 전자주입층 중 적어도 하나를 포함할 수 있고, 상기 유기층들 중 적어도 하나 이상이 상기 [화학식 A] 또는 [화학식 B]로 표시되는 방향족 헤테로고리 화합물을 1 종 이상 포함할 수 있다.At this time, the organic layer in the organic light emitting device of the present invention may include at least one of a hole injection layer, a hole transport layer, a functional layer having both a hole injection function and a hole transport function, a light emitting layer, an electron transport layer, and an electron injection layer, At least one of the organic layers may include one or more aromatic heterocyclic compounds represented by [Formula A] or [Formula B].
보다 바람직한 본 발명의 일 실시예로서, 본 발명은 제1전극; 상기 제1전극에 대향된 제2전극; 및 상기 제1전극과 상기 제2전극사이에 개재되는 유기층;을 포함하고, 상기 유기층은 발광층; 및, 정공 주입층, 정공 수송층, 정공 주입 기능 및 정공 수송 기능을 동시에 갖는 기능층, 전자저지층, 정공저지층, 전자 수송층 및 전자 주입층 중 적어도 하나의 층;을 포함하고, 상기 발광층은 호스트와 도판트를 포함하며, 상기 호스트는 본 발명에 따른 상기 방향족 헤테로고리 화합물을 1 종 이상 포함하는 유기발광소자를 제공한다.As a more preferred embodiment of the present invention, the present invention includes a first electrode; a second electrode opposite the first electrode; and an organic layer interposed between the first electrode and the second electrode, wherein the organic layer includes: a light emitting layer; And, at least one layer of a hole injection layer, a hole transport layer, a functional layer having both a hole injection function and a hole transport function, an electron blocking layer, a hole blocking layer, an electron transport layer, and an electron injection layer; and the light emitting layer is a host. and a dopant, and the host provides an organic light-emitting device including one or more of the aromatic heterocyclic compounds according to the present invention.
한편 본 발명에서 상기 발광층에는 호스트와 더불어, 도판트 재료가 사용될 수 있다. 상기 발광층이 호스트 및 도판트를 포함할 경우, 도판트의 함량은 통상적으로 호스트 약 100 중량부를 기준으로하여 약 0.01 내지 약 20중량부의 범위에서 선택될 수 있으며, 이에 한정되는 것은 아니다.Meanwhile, in the present invention, a dopant material may be used in the light emitting layer in addition to a host. When the light-emitting layer includes a host and a dopant, the content of the dopant can typically be selected in the range of about 0.01 to about 20 parts by weight based on about 100 parts by weight of the host, but is not limited thereto.
본 발명에서 상기 발광층에 포함되는 도판트 화합물로서, 상기 도판트는 기존의 Host-Dopant 시스템에서 포스터 에너지전이(Forster energy transfer) 방식을 이용하여 단일항 상태로만 전이되는 형광 도판트 물질이 아닌, 단일항과 삼중항 상태 구분하지 않고 전이되는 덱스터 에너지전이(Dexter Energy trnaster) 방식을 이용하는 Ir, Pt, Os, Ti, Zr, Hf, Eu, Tb, Tm, Fe, Co, Ni, Ru, Rh, Re, Pd 등에서 선택되는 하나 이상의 금속을 포함하는 금속착체의 인광 도판트 물질을 포함하며, 삼중항 여기자로부터 발광하는 한 특별한 제한 없이 공지의 도판트 물질을 사용할 수 있다.As a dopant compound included in the light-emitting layer in the present invention, the dopant is not a fluorescent dopant material that only transitions to a singlet state using the Forster energy transfer method in the existing host-dopant system, but a singlet dopant material. Ir, Pt, Os, Ti, Zr, Hf, Eu, Tb, Tm, Fe, Co, Ni, Ru, Rh, Re, using the Dexter Energy transfer method that transfers without distinguishing between and triplet states. It includes a phosphorescent dopant material of a metal complex containing one or more metals selected from Pd, etc., and known dopant materials can be used without particular restrictions as long as they emit light from triplet excitons.
바람직하게는 금속 착체로써 Ir, Pt 및 Pd 등을 선택할 수 있으며, 구체적인 예로는, Ir(ppy)3, Ir(ppy)2acac, Ir(Bt)2acac, Ir(MDQ)2acac, Ir(mppy)3, Ir(piq)3, Ir(piq)2acac, Ir(pq)2acac, Ir(mpp)2acac, F2Irpic, (F2ppy)2Ir(tmd), Ir(ppy)2tmd, Ir(pmi)3, Ir(pmb)3, FCNIr, FCNIrpic, FIr6, FIrN4, FIrpic, PtOEP, Ir(chpy)3,P0-01(C31H23IrN2O2S2), Ir(ppz)3, Ir(dfppz)3, PtNON, Pt-10, Pt-11 등이 있으나. 이에 제한되지 않으며, 더욱 바람직하게는 적색 인광 도판트로 사용되는 PtOEP, Ir(Bt)2acac, Ir(MDQ)2acac, Ir(piq)3, Ir(piq)2acac, Ir(pq)2acac 등이 사용될 수 있으며, 이에 제한되지 않는다.Preferably, Ir, Pt, Pd, etc. can be selected as the metal complex, and specific examples include Ir(ppy) 3 , Ir(ppy) 2 acac, Ir(Bt) 2 acac, Ir(MDQ) 2 acac, Ir( mppy) 3 , Ir(piq) 3, Ir (piq) 2 acac, Ir (pq) 2 acac, Ir(mpp) 2 acac, F 2 Irpic, (F 2 ppy) 2 Ir(tmd), Ir(ppy) 2 tmd, Ir(pmi) 3 , Ir(pmb) 3 , FCNIr, FCNIrpic, FIr6, FIrN4, FIrpic, PtOEP, Ir(chpy) 3 ,P0-01(C 31 H 23 IrN 2 O 2 S 2 ), Ir (ppz) 3, Ir(dfppz) 3, PtNON, Pt-10, Pt-11, etc. It is not limited thereto, and more preferably PtOEP, Ir(Bt) 2 acac, Ir(MDQ) 2 acac, Ir(piq) 3 , Ir(piq) 2 acac, Ir(pq) 2 acac used as a red phosphorescent dopant. etc. may be used, but are not limited thereto.
보다 바람직한 본 발명의 일 실시예로서, 본 발명은 상기 제1전극과 상기 제2전극 사이에 개재된 유기층이 발광층을 포함하며, 상기 발광층내 호스트는 상기 [화학식 A] 또는 [화학식 B]로 표시되는 화합물 1종 외 추가적인 호스트 화합물이 1종 이상 추가로 포함하여, 2종 이상의 호스트 화합물이 혼합 또는 적층되어 사용될 수 있다. As a more preferred embodiment of the present invention, the organic layer interposed between the first electrode and the second electrode includes a light-emitting layer, and the host in the light-emitting layer is represented by [Formula A] or [Formula B]. In addition to the one type of compound, one or more additional host compounds may be included, and two or more types of host compounds may be mixed or stacked.
여기서, 상기 [화학식 A] 또는 [화학식 B]로 표시되는 화합물 1종 외 추가적인 호스트 화합물이 1종 이상 추가로 포함하여, 2종 이상의 호스트 화합물이 혼합 또는 적층되어 사용되는 경우에, 보다 바람직하게는 상기 추가적인 호스트로서, 전자받개 모이어티를 가지는 화합물이 사용될 수 있으며, 전자주개 모이어티인 아민기를 가진 [화학식 A] 또는 [화학식 B]와의 혼합 또는 적층으로 생기는 높은 정공주입과 전자주입 장벽의 HOMO/LUMO 레벨로 인해 재결합영역을 두 호스트의 계면으로 제한함으로써 전류 손실을 최소화하는 장점 등으로 인해 고효율, 장수명의 유기발광소자를 구현할 수 있다.Here, in addition to the one compound represented by [Formula A] or [Formula B], one or more additional host compounds are additionally included, and when two or more host compounds are used mixed or stacked, more preferably As the additional host, a compound having an electron accepting moiety may be used, Due to the high hole injection caused by mixing or stacking with [Formula A] or [Formula B] having an amine group, which is an electron donor moiety, and the HOMO/LUMO level of the electron injection barrier, the recombination area is limited to the interface of the two hosts, thereby reducing current loss. Due to the advantages of minimizing high efficiency and long lifespan, organic light emitting devices can be implemented.
이때, 상기 전자받개 모이어티를 가지는 화합물은 분자내에 피리딘, 피리미딘, 트리아진 등과 같은 질소 함유 방향족 헤테로고리인 아진(Azine)화합물 및 시아노기(-CN)가 치환된 화합물 등과 같이 외부로부터 전자를 받기 쉬운 환경을 구비하고 있는 모이어티를 가지는 화합물로써, 바람직하게는 분자내 N(질소)을 1 내지 3개 포함하는 헤테로아릴기; 또는, 분자내 1 내지 3개의 시아노기(-CN)를 포함하는 아릴기;를 포함하는 화합물을 포함할 수 있다.At this time, compounds having the electron accepting moiety receive electrons from the outside, such as azine compounds, which are nitrogen-containing aromatic heterocycles such as pyridine, pyrimidine, and triazine, and compounds substituted with a cyano group (-CN) in the molecule. As a compound having a moiety that has an environment that is easy to receive, Preferably a heteroaryl group containing 1 to 3 N (nitrogen) elements in the molecule; Alternatively, it may include a compound containing an aryl group containing 1 to 3 cyano groups (-CN) in the molecule.
또한 상기 발광층은 상기 도판트와 호스트 이외에도 다양한 호스트와 다양한 도펀트 물질을 추가로 포함할 수 있다.Additionally, the light emitting layer may further include various hosts and various dopant materials in addition to the dopant and host.
이하, 도면을 참조하여 본 발명에 따른 유기발광소자를 설명한다. Hereinafter, an organic light emitting device according to the present invention will be described with reference to the drawings.
도 1은 본 발명의 일 실시예에 따른 유기 발광 소자의 구조를 도시한 그림이다.1 is a diagram showing the structure of an organic light-emitting device according to an embodiment of the present invention.
도 1에 도시된 바와 같이, 본 발명의 실시예에 따른 유기 발광 소자는 양극(20), 정공수송층(40), 호스트 및 도판트를 포함하는 발광층(50), 전자수송층(60) 및 음극(80)을 순차적 순서로 포함하는 유기발광소자로서, 상기 양극을 제1 전극으로, 음극을 제2전극으로 하여, 상기 양극과 발광층 사이에 정공수송층을 포함하고, 발광층과 음극 사이에 전자수송층을 포함한 유기발광소자에 해당한다. As shown in Figure 1, the organic light emitting device according to an embodiment of the present invention includes an anode 20, a hole transport layer 40, a light emitting layer 50 including a host and a dopant, an electron transport layer 60, and a cathode ( 80) in sequential order, wherein the anode is a first electrode, the cathode is a second electrode, a hole transport layer is provided between the anode and the light-emitting layer, and an electron transport layer is provided between the light-emitting layer and the cathode. Applies to organic light emitting devices.
또한, 본 발명의 실시예에 따른 유기 발광 소자는 상기 양극(20)과 정공수송층(40) 사이에 정공주입층(30)이 포함되며, 상기 전자수송층(60)과 음극(80) 사이에 전자주입층(70)이 포함될 수 있다.In addition, the organic light emitting device according to an embodiment of the present invention includes a hole injection layer 30 between the anode 20 and the hole transport layer 40, and an electron transport layer 60 and the cathode 80. An injection layer 70 may be included.
상기 도 1을 참조하여 본 발명의 유기 발광 소자 및 그 제조방법에 대하여 살펴보면 다음과 같다. The organic light-emitting device of the present invention and its manufacturing method will be described with reference to FIG. 1 as follows.
먼저 기판(10) 상부에 양극(애노드) 전극용 물질을 코팅하여 양극(20)을 형성한다. 여기에서 기판(10)으로는 통상적인 유기 EL 소자에서 사용되는 기판을 사용하는데 투명성, 표면 평활성, 취급용이성 및 방수성이 우수한 유기 기판 또는 투명 플라스틱 기판이 바람직하다. 그리고, 양극 전극용 물질로는 투명하고 전도성이 우수한 산화인듐주석(ITO), 산화인듐아연(IZO), 산화주석(SnO2), 산화아연(ZnO) 등을 사용한다. First, the positive electrode (anode) material is coated on the upper part of the substrate 10 to form the positive electrode 20. Here, as the substrate 10, a substrate used in a typical organic EL device is used, and an organic substrate or a transparent plastic substrate having excellent transparency, surface smoothness, ease of handling, and waterproofness is preferable. In addition, indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO 2 ), and zinc oxide (ZnO), which are transparent and have excellent conductivity, are used as materials for the anode electrode.
상기 양극(20) 전극 상부에 정공 주입층 물질을 진공열 증착, 또는 스핀 코팅하여 정공주입층(30)을 형성한다. 그 다음으로 상기 정공주입층(30)의 상부에 정공수송층 물질을 진공 열증착 또는 스핀 코팅하여 정공수송층(40)을 형성한다.The hole injection layer 30 is formed by vacuum thermal deposition or spin coating of a hole injection layer material on the upper electrode of the anode 20. Next, a hole transport layer 40 is formed on the top of the hole injection layer 30 by vacuum thermal evaporation or spin coating of a hole transport layer material.
상기 정공주입층 재료는 당업계에서 통상적으로 사용되는 것인 한 특별히 제한되지 않고 사용할 수 있으며, 예를 들어 2-TNATA [4,4',4"-tris(2-naphthylphenyl-phenylamino)-triphenylamine], NPD[N,N'-di(1-naphthyl)-N,N'-diphenylbenzidine)], TPD[N,N'-diphenyl-N,N'-bis(3-methylphenyl)-1,1'-biphenyl-4,4'-diamine], DNTPD[N,N'-diphenyl-N,N'-bis-[4-(phenyl-m-tolyl-amino)-phenyl]-biphenyl-4,4'-diamine] 등을 사용할 수 있다. 하지만 본 발명이 반드시 이에 한정되는 것은 아니다.The hole injection layer material can be used without particular restrictions as long as it is commonly used in the industry, for example, 2-TNATA [4,4',4"-tris(2-naphthylphenyl-phenylamino)-triphenylamine] , NPD[N,N'-di(1-naphthyl)-N,N'-diphenylbenzidine)], TPD[N,N'-diphenyl-N,N'-bis(3-methylphenyl)-1,1'- biphenyl-4,4'-diamine], DNTPD[N,N'-diphenyl-N,N'-bis-[4-(phenyl-m-tolyl-amino)-phenyl]-biphenyl-4,4'-diamine ] can be used, etc. However, the present invention is not necessarily limited to this.
또한 상기 정공수송층의 재료로서 당업계에 통상적으로 사용되는것인 한 특별히 제한되지 않으며, 예를 들어, N,N'-비스(3-메틸페닐)-N,N'-디페닐 -[1,1-비페닐]-4,4'-디아민(TPD) 또는 N,N'-디(나프탈렌-1-일)-N,N'-디페닐벤지딘(a-NPD) 등을 사용할 수 있다. 하지만 본 발명이 반드시 이에 한정되는 것은 아니다.Additionally, the material of the hole transport layer is not particularly limited as long as it is commonly used in the art, for example, N,N'-bis(3-methylphenyl)-N,N'-diphenyl -[1,1- Biphenyl]-4,4'-diamine (TPD) or N,N'-di(naphthalen-1-yl)-N,N'-diphenylbenzidine (a-NPD) can be used. However, the present invention is not necessarily limited thereto.
한편, 본 발명은 상기 정공 수송층 상부에 전자 차단층을 추가적으로 형성할 수 있다. 상기 전자차단층은 전자주입층으로부터 주입된 전자가 발광층을 지나 정공수송층으로 진입하는 것을 방지하여 소자의 수명과 효율을 향상시키기 위한 층으로서, 발광층과 정공주입층의 사이에 적절한 부분에 형성될 수 있으며, 바람직하게는 발광층과 정공수송층 사이에 형성될 수 있다.Meanwhile, in the present invention, an electron blocking layer may be additionally formed on the hole transport layer. The electron blocking layer is a layer to improve the lifespan and efficiency of the device by preventing electrons injected from the electron injection layer from passing through the light-emitting layer and entering the hole transport layer, and can be formed in an appropriate portion between the light-emitting layer and the hole injection layer. and may preferably be formed between the light emitting layer and the hole transport layer.
이어서, 상기 정공수송층(40) 또는 전자차단층의 상부에 발광층(50)을 진공 증착 방법, 또는 스핀 코팅 방법으로서 적층할 수 있다.Subsequently, the light emitting layer 50 may be laminated on the hole transport layer 40 or the electron blocking layer using a vacuum deposition method or a spin coating method.
여기서, 상기 발광층은 호스트와 도펀트로 이루어질 수 있으며, 이들을 구성하는 재료에 대해서는 앞서 기재한 바와 같다.Here, the light-emitting layer may be composed of a host and a dopant, and the materials constituting them are as described above.
또한, 본 발명의 구체적인 예에 의하면, 상기 발광층의 두께는 50 내지 2,000 Å인 것이 바람직하다. Additionally, according to a specific example of the present invention, the thickness of the light-emitting layer is preferably 50 to 2,000 Å.
본 발명은 상기 유기발광층(50)의 상부에 선택적으로, 정공저지층(미도시)을 진공 증착 방법, 또는 스핀 코팅 방법으로서 박막을 형성할 수 있다. In the present invention, a thin film of a hole blocking layer (not shown) can be selectively formed on the organic light emitting layer 50 using a vacuum deposition method or a spin coating method.
상기 정공저지층은 정공이 발광층을 통과하여 캐소드로 유입되는 경우에는 소자의 수명과 효율이 감소되기 때문에 HOMO(Highest Occupied Molecular Orbital) 레벨이 매우 낮은 물질을 사용함으로써 이러한 문제를 방지하는 역할을 한다. 이 때, 사용되는 정공 저지 물질은 특별히 제한되지는 않으나 전자수송능력을 가지면서 발광 화합물보다 높은 이온화 포텐셜을 가져야 하며, 상기 정공저지층에 사용되는 물질로써, BAlq, BCP, Bphen, TPBI, NTAZ, BeBq2, OXD-7, Liq 및 화학식 1001 내지 화학식 1007 중 에서 선택되는 어느 하나가 사용될 수 있으나, 이에 한정되는 것은 아니다.The hole blocking layer serves to prevent this problem by using a material with a very low HOMO (Highest Occupied Molecular Orbital) level because the lifespan and efficiency of the device are reduced when holes pass through the light emitting layer and flow into the cathode. At this time, the hole blocking material used is not particularly limited, but must have electron transport ability and a higher ionization potential than the light-emitting compound. Materials used in the hole blocking layer include BAlq, BCP, Bphen, TPBI, NTAZ, BeBq 2 , OXD-7, Liq and any one selected from Formulas 1001 to 1007 may be used, but are not limited thereto.
BAlq BCP BphenBAlq BCP Bphen
Figure PCTKR2023003724-appb-img-000100
Figure PCTKR2023003724-appb-img-000100
TPBI NTAZ BeBq2 TPBI NTAZ BeBq 2
Figure PCTKR2023003724-appb-img-000101
Figure PCTKR2023003724-appb-img-000101
OXD-7 Liq OXD-7 Liq
Figure PCTKR2023003724-appb-img-000102
Figure PCTKR2023003724-appb-img-000102
화학식 1001 화학식 1002 화학식 1003 Formula 1001 Formula 1002 Formula 1003
Figure PCTKR2023003724-appb-img-000103
Figure PCTKR2023003724-appb-img-000103
화학식 1004 화학식 1005 화학식 1006Formula 1004 Formula 1005 Formula 1006
Figure PCTKR2023003724-appb-img-000104
Figure PCTKR2023003724-appb-img-000104
화학식 1007Chemical formula 1007
Figure PCTKR2023003724-appb-img-000105
Figure PCTKR2023003724-appb-img-000105
한편, 상기 발광층 또는 정공저지층 상에 전자수송층(60)을 진공 증착 방법, 또는 스핀 코팅 방법을 통해 증착한다. Meanwhile, the electron transport layer 60 is deposited on the light emitting layer or the hole blocking layer through a vacuum deposition method or a spin coating method.
한편 본 발명에서 상기 전자수송층 재료로는 전자주입전극(Cathode)로부터 주입된 전자를 안정하게 수송하는 기능을 하는 것으로서 공지의 전자수송물질을 이용할 수 있다. 공지의 전자수송물질의 예로는, 퀴놀린유도체, 특히트리스(8-퀴놀리노레이트)알루미늄(Alq3), Liq, TAZ, BAlq, 베릴륨비스(벤조퀴놀리-10-노에이트)(beryllium bis(benzoquinolin-10-olate: Bebq2), 화합물 201, 화합물 202, BCP, 옥사디아졸유도체인 PBD, BMD, BND 등과 같은 재료를 사용할 수도 있으나, 이에 한정되는 것은 아니다.Meanwhile, in the present invention, as the material for the electron transport layer, a known electron transport material that functions to stably transport electrons injected from an electron injection electrode (cathode) can be used. Examples of known electron transport materials include quinoline derivatives, especially tris(8-quinolinolate) aluminum (Alq 3 ), Liq, TAZ, BAlq, beryllium bis(benzoquinolin-10-noate) Materials such as -10-olate: Bebq2), Compound 201, Compound 202, BCP, and oxadiazole derivatives such as PBD, BMD, and BND may be used, but are not limited thereto.
Figure PCTKR2023003724-appb-img-000106
Figure PCTKR2023003724-appb-img-000106
TAZ BAlqTAZ BAlq
Figure PCTKR2023003724-appb-img-000107
Figure PCTKR2023003724-appb-img-000107
<화합물 201> <화합물 202> BCP<Compound 201> <Compound 202> BCP
Figure PCTKR2023003724-appb-img-000108
Figure PCTKR2023003724-appb-img-000108
또한, 본 발명에서의 유기발광소자는 상기 전자수송층을 형성한 후에 전자 수송층 상부에 음극으로부터 전자의 주입을 용이하게 하는 기능을 가지는 물질인 전자 주입층(EIL)이 적층될 수 있으며 이는 특별히 재료를 제한하지 않는다.In addition, in the organic light emitting device of the present invention, after forming the electron transport layer, an electron injection layer (EIL), which is a material that has the function of facilitating injection of electrons from the cathode, can be laminated on the top of the electron transport layer. This is a special material. No restrictions.
상기 전자 주입층 형성 재료로는 CsF, NaF, LiF, Li2O, BaO등과 같은 전자주입층 형성 재료로서 공지된 임의의 물질을 이용할 수 있다. 상기 전자주입층의 증착조건은 사용하는 화합물에 따라 다르지만, 일반적으로 정공 주입층의 형성과 거의 동일한 조건범위 중에서 선택될 수 있다.As the electron injection layer forming material, any material known as an electron injection layer forming material such as CsF, NaF, LiF, Li 2 O, BaO, etc. can be used. The deposition conditions for the electron injection layer vary depending on the compound used, but can generally be selected from a range of conditions that are substantially the same as those for forming the hole injection layer.
상기 전자 주입층의 두께는 약 1 Å 내지 약 100 Å, 약 3 Å 내지 약 90 Å일 수 있다. 상기 전자 주입층의 두께가 전술한 바와 같은 범위를 만족할 경우, 실질적인 구동 전압 상승없이 만족스러운 정도의 전자 주입 특성을 얻을 수 있다.The thickness of the electron injection layer may be about 1 Å to about 100 Å, or about 3 Å to about 90 Å. When the thickness of the electron injection layer satisfies the range described above, satisfactory electron injection characteristics can be obtained without a substantial increase in driving voltage.
또한, 본 발명에서 상기 음극은 전자 주입이 용이하도록 일함수가 작은 물질을 이용할 수 있다. 리튬(Li), 마그네슘(Mg), 칼슘(Ca), 또는 이들의 합금 알루미늄(Al), 알루미늄-리듐(Al-Li), 마그네슘-인듐(Mg-In), 마그네슘-은(Mg-Ag) 등을 사용하거나, ITO, IZO를 사용한 투과형 음극을 사용할 수 있다.Additionally, in the present invention, the cathode may be made of a material with a low work function to facilitate electron injection. Lithium (Li), magnesium (Mg), calcium (Ca), or their alloys aluminum (Al), aluminum-lithium (Al-Li), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag) etc., or a transmission type cathode using ITO or IZO can be used.
또한 본 발명에서의 유기 발광 소자는 380 nm 내지 800 nm의 파장범위에서 발광하는 청색 발광재료, 녹색 발광재료 또는 적색 발광재료의 발광층을 추가적으로 포함할 수 있다. 즉, 본 발명에서의 발광층은 복수의 발광층으로서, 상기 추가적으로 형성되는 발광층내 청색 발광재료, 녹색 발광재료 또는 적색 발광재료는 형광재료 또는 인광재료일 수 있다.Additionally, the organic light-emitting device of the present invention may additionally include a light-emitting layer of a blue light-emitting material, a green light-emitting material, or a red light-emitting material that emits light in a wavelength range of 380 nm to 800 nm. That is, the light-emitting layer in the present invention is a plurality of light-emitting layers, and the blue light-emitting material, green light-emitting material, or red light-emitting material in the additionally formed light-emitting layer may be a fluorescent material or a phosphorescent material.
또한, 본 발명에서 상기 각각의 층중에서 선택된 하나 이상의 층은 단분자 증착공정 또는 용액공정에 의하여 형성될 수 있다. Additionally, in the present invention, one or more layers selected from among the above layers may be formed by a single molecule deposition process or a solution process.
여기서 상기 증착 공정은 상기 각각의 층을 형성하기 위한 재료로 사용되는 물질을 진공 또는 저압상태에서 가열 등을 통해 증발시켜 박막을 형성하는 방법을 의미하고, 상기 용액공정은 상기 각각의 층을 형성하기 위한 재료로 사용되는 물질을 용매와 혼합하고 이를 잉크젯 인쇄, 롤투롤 코팅, 스크린 인쇄, 스프레이 코팅, 딥 코팅, 스핀 코팅 등과 같은 방법을 통하여 박막을 형성하는 방법을 의미한다. Here, the deposition process refers to a method of forming a thin film by evaporating the material used as a material for forming each layer through heating in a vacuum or low pressure state, and the solution process is used to form each layer. This refers to a method of mixing a substance used as a material with a solvent and forming a thin film through methods such as inkjet printing, roll-to-roll coating, screen printing, spray coating, dip coating, and spin coating.
또한 본 발명에서의 상기 유기 발광 소자는 평판 디스플레이 장치; 플렉시블 디스플레이 장치; 단색 또는 백색의 평판 조명용 장치; 및 단색 또는 백색의 플렉시블 조명용 장치; 차량용 디스플레이 장치; 및 가상 또는 증강 현실용 디스플레이 장치;에서 선택되는 어느 하나의 장치에 사용될 수 있다. Additionally, the organic light emitting device in the present invention may include a flat panel display device; flexible display device; Devices for monochromatic or white flat panel lighting; and devices for single-color or white flexible lighting; Vehicle display devices; and a display device for virtual or augmented reality.
이하, 바람직한 실시예를 들어 본 발명을 더욱 상세하게 설명한다. 그러나, 이들 실시예는 본 발명을 보다 구체적으로 설명하기 위한 것으로, 본 발명의 범위가 이에 의하여 제한되지 않는다는 것은 당업계의 통상의 지식을 가진 자에게 자명할 것이다. Hereinafter, the present invention will be described in more detail with reference to preferred embodiments. However, these examples are for illustrating the present invention in more detail, and it will be apparent to those skilled in the art that the scope of the present invention is not limited thereto.
(실시예) (Example)
합성예 1. [화합물 182]의 제조Synthesis Example 1. Preparation of [Compound 182]
합성예 1-1 : A-1의 합성Synthesis Example 1-1: Synthesis of A-1
Figure PCTKR2023003724-appb-img-000109
Figure PCTKR2023003724-appb-img-000109
<A-1a> <A-1b> <A-1><A-1a> <A-1b> <A-1>
질소퍼지한 반응기에 <A-1a> 50 g, 자일렌 500 mL, 피리딘 21.5 mL, <A-1b> 30.9 mL를 투입하였다. 1시간 후, 파라 톨루엔 술폰산 137.4 g을 투입하고, 120 ℃로 승온하였다. 16시간 후, 상온으로 냉각한 다음, 에틸아세테이트와 물을 투입하여 층분리 하였다. 유기층을 감압 농축 후, 실리카겔 컬럼크로마토그래피로 정제하여 <A-1>을 얻었다. (36.3 g, 49.8%)50 g of <A-1a>, 500 mL of xylene, 21.5 mL of pyridine, and 30.9 mL of <A-1b> were added to the nitrogen-purged reactor. After 1 hour, 137.4 g of para-toluene sulfonic acid was added, and the temperature was raised to 120°C. After 16 hours, it was cooled to room temperature, and then ethyl acetate and water were added to separate the layers. The organic layer was concentrated under reduced pressure and purified by silica gel column chromatography to obtain <A-1>. (36.3 g, 49.8%)
합성예 1-2 : A-2의 합성Synthesis Example 1-2: Synthesis of A-2
Figure PCTKR2023003724-appb-img-000110
Figure PCTKR2023003724-appb-img-000110
<A-1> <A-2><A-1> <A-2>
질소퍼지한 반응기에 <A-1> 36.3 g, 테트라하이드로퓨란 360 mL를 투입하고, -78 ℃로 냉각하였다. 2M 리튬다이아이소프로필아마이드 109 mL를 적하한 다음, 2시간 반 후 메틸 아이오다이드 26.3 g을 적하한 뒤 30분 후 상온으로 승온하였다. 16시간 후, 암모늄클로라이드 포화 수용액과 에틸아세테이트를 투입하고 층분리 하였다. 유기층을 감압 농축 후, 실리카겔 컬럼크로마토그래피로 정제하여 <A-2>를 얻었다. (30.4 g, 79.7%)36.3 g of <A-1> and 360 mL of tetrahydrofuran were added to the nitrogen-purged reactor and cooled to -78°C. 109 mL of 2M lithium diisopropylamide was added dropwise, and after 2.5 hours, 26.3 g of methyl iodide was added dropwise, and the temperature was raised to room temperature after 30 minutes. After 16 hours, saturated aqueous ammonium chloride solution and ethyl acetate were added and the layers were separated. The organic layer was concentrated under reduced pressure and purified by silica gel column chromatography to obtain <A-2>. (30.4 g, 79.7%)
합성예 1-3 : A-3의 합성Synthesis Example 1-3: Synthesis of A-3
Figure PCTKR2023003724-appb-img-000111
Figure PCTKR2023003724-appb-img-000111
<A-2> <A-3a> <A-3> <A-2> <A-3a> <A-3>
질소퍼지한 반응기에 <A-2> 30.4 g, <A-3a> 21.4 g, 테트라키스(트리페닐포스핀)팔라듐(0) 2.44 g, 포타슘 카보네이트 36.5 g, 톨루엔 122 mL, 에탄올 91 mL, 물 91 mL를 투입하고, 100 ℃로 승온하였다. 16시간 후, 에틸아세테이트와 물을 투입하여 층분리 하였다. 유기층을 감압 농축 후, 실리카겔 컬럼크로마토그래피로 정제하여 <A-3>을 얻었다. (14.7 g, 40.1%)In a nitrogen-purged reactor, 30.4 g of <A-2>, 21.4 g of <A-3a>, 2.44 g of tetrakis(triphenylphosphine)palladium(0), 36.5 g of potassium carbonate, 122 mL of toluene, 91 mL of ethanol, and water. 91 mL was added, and the temperature was raised to 100°C. After 16 hours, ethyl acetate and water were added to separate the layers. The organic layer was concentrated under reduced pressure and purified by silica gel column chromatography to obtain <A-3>. (14.7 g, 40.1%)
합성예 1-4 : A-4의 합성Synthesis Example 1-4: Synthesis of A-4
Figure PCTKR2023003724-appb-img-000112
Figure PCTKR2023003724-appb-img-000112
<A-3> <A-4> <A-3> <A-4>
질소퍼지한 반응기에 <A-3> 9 g, 다이메틸포름아마이드 90 mL를 투입하였다. 영하 30 ℃로 냉각 후, 포타슘 터셔리 부톡사이드 3.5 g을 투입하였다. 1시간 후, 반응액을 메탄올 300 mL가 들어있는 다른 반응기에 투입하였다. 1시간 후, 여과하고 얻은 고체를 재결정하여 <A-4>를 얻었다. (2.7 g, 31.6%)9 g of <A-3> and 90 mL of dimethylformamide were added to the nitrogen-purged reactor. After cooling to -30°C, 3.5 g of potassium tertiary butoxide was added. After 1 hour, the reaction solution was added to another reactor containing 300 mL of methanol. After 1 hour, the solid obtained after filtration was recrystallized to obtain <A-4>. (2.7 g, 31.6%)
합성예 1-5. [화합물 182]의 합성Synthesis Example 1-5. Synthesis of [Compound 182]
Figure PCTKR2023003724-appb-img-000113
Figure PCTKR2023003724-appb-img-000113
<A-4> <A-5a> [화합물 182]<A-4> <A-5a> [Compound 182]
질소퍼지한 반응기에 <A-4> 5.8 g, <A-5a> 6.5 g, 비스(트리터셔리부틸포스핀)팔라듐(0) 0.18 g, 소듐 터셔리 부톡사이드 3.4 g, 톨루엔 58 mL을 투입하고 110 ℃로 승온하였다. 3시간 후, 에틸아세테이트와 물을 투입하여 층분리 하였다. 유기층을 감압 농축 후, 톨루엔을 투입하고 가열하여 녹인 후, 실리카겔을 사용하여 여과한 다음, 감압농축하고 재결정하여 [화합물 182]를 얻었다. (2.9 g, 26.2%)Introduce 5.8 g of <A-4>, 6.5 g of <A-5a>, 0.18 g of bis(tri-tertiary butylphosphine)palladium(0), 3.4 g of sodium tertiary butoxide, and 58 mL of toluene into the nitrogen-purged reactor. And the temperature was raised to 110°C. After 3 hours, ethyl acetate and water were added to separate the layers. After concentrating the organic layer under reduced pressure, toluene was added and heated to dissolve, filtered using silica gel, concentrated under reduced pressure, and recrystallized to obtain [Compound 182]. (2.9 g, 26.2%)
MS (MALDI-TOF) : m/z 628.22 [M+]MS (MALDI-TOF): m/z 628.22 [M + ]
합성예 2. [화합물 186]의 제조Synthesis Example 2. Preparation of [Compound 186]
합성예 2-1 : B-1의 합성Synthesis Example 2-1: Synthesis of B-1
Figure PCTKR2023003724-appb-img-000114
Figure PCTKR2023003724-appb-img-000114
<A-1> <B-1> <A-1> <B-1>
질소퍼지한 반응기에 <A-1> 40 g, 테트라하이드로퓨란 480 mL를 투입하고, -78 ℃로 냉각하였다. 2M 리튬다이아이소프로필아마이드 109 mL를 적하한 다음, 1시간 후 다이메틸포름아마이드 7.8 mL을 적하하였다. 4시간 반 후, 상온으로 승온하고, 암모늄클로라이드 포화 수용액과 에틸아세테이트를 투입하고 층분리 하였다. 유기층을 감압 농축 후, 실리카겔 컬럼크로마토그래피로 정제하여 <B-1>을 얻었다. (33.5 g, 76%)40 g of <A-1> and 480 mL of tetrahydrofuran were added to the nitrogen-purged reactor and cooled to -78°C. 109 mL of 2M lithium diisopropylamide was added dropwise, and after 1 hour, 7.8 mL of dimethylformamide was added dropwise. After 4 and a half hours, the temperature was raised to room temperature, saturated aqueous ammonium chloride solution and ethyl acetate were added, and the layers were separated. The organic layer was concentrated under reduced pressure and purified by silica gel column chromatography to obtain <B-1>. (33.5 g, 76%)
합성예 2-2 : B-2의 합성Synthesis Example 2-2: Synthesis of B-2
Figure PCTKR2023003724-appb-img-000115
Figure PCTKR2023003724-appb-img-000115
<B-1> <B-2a> <B-2> <B-1> <B-2a> <B-2>
상기 합성예 1-3에서 사용한 <A-2> 대신 <B-1>을 사용하고, <A-3a> 대신 <B-2a>를 사용한 것을 제외하고는 동일한 방법으로 합성하여 <B-2>를 얻었다. (수율 68.2%)<B-2> was synthesized in the same manner except that <B-1> was used instead of <A-2> used in Synthesis Example 1-3, and <B-2a> was used instead of <A-3a>. got it (yield 68.2%)
합성예 2-3 : B-3의 합성Synthesis Example 2-3: Synthesis of B-3
Figure PCTKR2023003724-appb-img-000116
Figure PCTKR2023003724-appb-img-000116
<B-2> <B-3a> <B-3><B-2> <B-3a> <B-3>
질소퍼지한 반응기에 포타슘 터셔리-부톡사이드 19.7 g, 테트라하이드로퓨란 260 mL을 투입하고 -20 ℃로 냉각하였다. 20분 후, <B-3a> 19.7 g을 투입한 후 30분 뒤 <B-2> 12.8 g을 투입하고 상온으로 승온하였다. 에틸아세테이트와 물을 투입하여 층분리 한 뒤 유기층을 감압 농축 후, 실리카겔 컬럼크로마토그래피로 정제하여 <B-3>을 얻었다. (12.7 g, 91.5%)19.7 g of potassium tertiary-butoxide and 260 mL of tetrahydrofuran were added to the nitrogen-purged reactor and cooled to -20°C. After 20 minutes, 19.7 g of <B-3a> was added, and 30 minutes later, 12.8 g of <B-2> was added and the temperature was raised to room temperature. After separating the layers by adding ethyl acetate and water, the organic layer was concentrated under reduced pressure and purified by silica gel column chromatography to obtain <B-3>. (12.7 g, 91.5%)
합성예 2-4 : B-4의 합성Synthesis Example 2-4: Synthesis of B-4
Figure PCTKR2023003724-appb-img-000117
Figure PCTKR2023003724-appb-img-000117
<B-3> <B-4><B-3> <B-4>
질소퍼지한 반응기에 <B-3> 12.7 g, 모노클로로벤젠 102 mL, 이튼시약 2.5 mL 을 투입하고, 130 ℃로 승온하였다. 2시간 후, 메탄올 300 mL가 들어있는 다른 반응기에 반응액을 투입하였다. 1시간 후, 여과하고 얻은 고체에 톨루엔을 투입하고 가열하여 녹인 후, 실리카겔을 사용하여 여과한 다음, 감압농축하고 재결정하여 <B-4>를 얻었다. (6.6 g, 57%)12.7 g of <B-3>, 102 mL of monochlorobenzene, and 2.5 mL of Eaton's reagent were added to the nitrogen-purged reactor, and the temperature was raised to 130°C. After 2 hours, the reaction solution was added to another reactor containing 300 mL of methanol. After 1 hour, toluene was added to the solid obtained after filtration, heated to dissolve, filtered using silica gel, concentrated under reduced pressure, and recrystallized to obtain <B-4>. (6.6 g, 57%)
합성예 2-5 : B-5의 합성Synthesis Example 2-5: Synthesis of B-5
Figure PCTKR2023003724-appb-img-000118
Figure PCTKR2023003724-appb-img-000118
<B-5a> <B-5b> <B-5><B-5a> <B-5b> <B-5>
질소퍼지한 반응기에 <B-5a> 50 g, <B-5b> 53.1 g, 트리스(다이벤질리덴아세톤)다이팔라듐(0) 4.4 g, 바이냅 6 g, 소듐터셔리부톡사이드 46.4 g, 톨루엔 500 mL 을 투입하고, 110 ℃로 승온하였다. 20분 후, 상온으로 냉각한 다음, 에틸아세테이트와 물을 투입하여 층분리 하였다. 유기층을 감압 농축 후, 실리카겔 컬럼크로마토그래피로 정제하여 <B-5>를 얻었다. (50 g, 61.7%)In a nitrogen-purged reactor, 50 g of <B-5a>, 53.1 g of <B-5b>, 4.4 g of tris(dibenzylideneacetone)dipalladium (0), 6 g of Vinap, 46.4 g of sodium tertiary butoxide, 500 mL of toluene was added, and the temperature was raised to 110°C. After 20 minutes, it was cooled to room temperature, and then ethyl acetate and water were added to separate the layers. The organic layer was concentrated under reduced pressure and purified by silica gel column chromatography to obtain <B-5>. (50 g, 61.7%)
합성예 2-6 : [화합물 186]의 합성Synthesis Example 2-6: Synthesis of [Compound 186]
Figure PCTKR2023003724-appb-img-000119
Figure PCTKR2023003724-appb-img-000119
<B-4> <B-5> [화합물 186] <B-4> <B-5> [Compound 186]
상기 합성예 1-5에서 사용한 <A-4> 대신 <B-4>를 사용하고, <A-5a> 대신 <B-5>를 사용한 것을 제외하고는 동일한 방법으로 합성하여 [화합물 186]를 얻었다. (수율 53.4%)[Compound 186] was synthesized in the same manner, except that <B-4> was used instead of <A-4> used in Synthesis Example 1-5, and <B-5> was used instead of <A-5a>. got it (yield 53.4%)
MS (MALDI-TOF) : m/z 628.25 [M+]MS (MALDI-TOF): m/z 628.25 [M + ]
합성예 3. [화합물 190]의 제조Synthesis Example 3. Preparation of [Compound 190]
합성예 3-1 : C-1의 합성Synthesis Example 3-1: Synthesis of C-1
Figure PCTKR2023003724-appb-img-000120
Figure PCTKR2023003724-appb-img-000120
<C-1a> <A-1b> <C-1><C-1a> <A-1b> <C-1>
질소퍼지한 반응기에 <C-1a> 100 g, 아이오딘 8.4 g, 피리딘 500 mL을 투입하였다. <A-1b> 57.9 mL를 적하하고, 80 ℃로 승온하였다. 3시간 후, 상온으로 냉각한 다음, 포화 소듐싸이오설페이트 수용액과 에틸아세테이트를 투입하여 층분리 하였다. 유기층을 감압 농축 후, 톨루엔을 투입하고 가열하여 녹인 후, 실리카겔을 사용하여 여과한 다음, 감압농축하고 재결정하여 <C-1>을 얻었다. (128 g, 95.1%)100 g of <C-1a>, 8.4 g of iodine, and 500 mL of pyridine were added to the nitrogen-purged reactor. <A-1b> 57.9 mL was added dropwise, and the temperature was raised to 80°C. After 3 hours, it was cooled to room temperature, and then saturated sodium thiosulfate aqueous solution and ethyl acetate were added to separate the layers. After concentrating the organic layer under reduced pressure, toluene was added and heated to dissolve, filtered using silica gel, concentrated under reduced pressure, and recrystallized to obtain <C-1>. (128 g, 95.1%)
합성예 3-2. C-2의 합성Synthesis Example 3-2. Synthesis of C-2
Figure PCTKR2023003724-appb-img-000121
Figure PCTKR2023003724-appb-img-000121
<C-1> <C-2><C-1> <C-2>
질소퍼지한 반응기에 <C-1> 128 g, 포타슘 카보네이트 87.3 g, 다이메틸술폭사이드 1300 mL을 투입하고, 140 ℃로 승온하였다. 16시간 후, 상온으로 냉각한 다음, 물 5 L가 들어있는 반응기에 반응액을 투입하였다. 여과하여 얻은 고체를 톨루엔을 투입하고 가열하여 녹인 후, 실리카겔을 사용하여 여과한 다음, 감압농축하고 재결정하여 <C-2>를 얻었다. (39.3 g, 38.4%)128 g of <C-1>, 87.3 g of potassium carbonate, and 1300 mL of dimethyl sulfoxide were added to the nitrogen-purged reactor, and the temperature was raised to 140°C. After 16 hours, it was cooled to room temperature, and then the reaction solution was added to a reactor containing 5 L of water. The solid obtained by filtration was dissolved by adding toluene and heating, then filtered using silica gel, concentrated under reduced pressure, and recrystallized to obtain <C-2>. (39.3 g, 38.4%)
합성예 3-3 : C-3의 합성Synthesis Example 3-3: Synthesis of C-3
Figure PCTKR2023003724-appb-img-000122
Figure PCTKR2023003724-appb-img-000122
<C-2> <C-3> <C-2> <C-3>
상기 합성예 2-1에서 사용한 <A-1> 대신 <C-2>를 사용한 것을 제외하고는 동일한 방법으로 합성하여 <C-3>를 얻었다. (수율 71.1%)<C-3> was obtained by synthesis in the same manner, except that <C-2> was used instead of <A-1> used in Synthesis Example 2-1. (yield 71.1%)
합성예 3-4 : C-4의 합성Synthesis Example 3-4: Synthesis of C-4
Figure PCTKR2023003724-appb-img-000123
Figure PCTKR2023003724-appb-img-000123
<C-3> <A-3a> <C-4><C-3> <A-3a> <C-4>
상기 합성예 1-3에서 사용한 <A-2> 대신 <C-3>을 사용한 것을 제외하고는 동일한 방법으로 합성하여 <C-4>를 얻었다. (수율 85.9%)<C-4> was obtained by synthesis in the same manner, except that <C-3> was used instead of <A-2> used in Synthesis Example 1-3. (yield 85.9%)
합성예 3-5 : C-5의 합성Synthesis Example 3-5: Synthesis of C-5
Figure PCTKR2023003724-appb-img-000124
Figure PCTKR2023003724-appb-img-000124
<C-4> <C-5> <C-4> <C-5>
질소퍼지한 반응기에 <C-4> 30.5 g, 아세틱 에시드 1000 mL를 투입하였다. 하이드라진 3.1 g을 아세틱 에시트 200 mL로 녹인 용액을 적하하고, 120 ℃로 승온하였다. 3시간 30분 후, 상온으로 냉각한 다음, 물 4 L를 투입하고 여과하였다. 여과하여 얻은 고체를 톨루엔을 투입하고 가열하여 녹인 후, 실리카겔을 사용하여 여과한 다음, 감압농축하고 재결정하여 <C-5>를 얻었다. (12.6 g, 44.8%)30.5 g of <C-4> and 1000 mL of acetic acid were added to the nitrogen-purged reactor. A solution of 3.1 g of hydrazine dissolved in 200 mL of acetic acid was added dropwise, and the temperature was raised to 120°C. After 3 hours and 30 minutes, it was cooled to room temperature, then 4 L of water was added and filtered. The solid obtained by filtration was dissolved by adding toluene and heating, then filtered using silica gel, concentrated under reduced pressure, and recrystallized to obtain <C-5>. (12.6 g, 44.8%)
합성예 3-6 : [화합물 190]의 합성Synthesis Example 3-6: Synthesis of [Compound 190]
Figure PCTKR2023003724-appb-img-000125
Figure PCTKR2023003724-appb-img-000125
<C-5> <A-5a> [화합물 190] <C-5> <A-5a> [Compound 190]
상기 합성예 1-5에서 사용한 <A-4> 대신 <C-5>를 사용한 것을 제외하고는 동일한 방법으로 합성하여 [화합물 190]을 얻었다. (수율 61.5%)[Compound 190] was obtained by synthesis in the same manner except that <C-5> was used instead of <A-4> used in Synthesis Example 1-5. (yield 61.5%)
MS (MALDI-TOF) : m/z 678.23 [M+]MS (MALDI-TOF): m/z 678.23 [M + ]
합성예 4. [화합물 194]의 제조Synthesis Example 4. Preparation of [Compound 194]
합성예 4-1 : [화합물 194]의 합성Synthesis Example 4-1: Synthesis of [Compound 194]
Figure PCTKR2023003724-appb-img-000126
Figure PCTKR2023003724-appb-img-000126
<B-4> <A-5a> [화합물 194]<B-4> <A-5a> [Compound 194]
상기 합성예 1-5에서 사용한 <A-4> 대신 <B-4>를 사용한 것을 제외하고는 동일한 방법으로 합성하여 [화합물 194]를 얻었다. (수율 75.3%) [Compound 194] was obtained by synthesis in the same manner except that <B-4> was used instead of <A-4> used in Synthesis Example 1-5. (yield 75.3%)
MS (MALDI-TOF) : m/z 628.22 [M+]MS (MALDI-TOF): m/z 628.22 [M + ]
합성예 5. [화합물 196]의 제조Synthesis Example 5. Preparation of [Compound 196]
합성예 5-1 : E-1의 합성Synthesis Example 5-1: Synthesis of E-1
Figure PCTKR2023003724-appb-img-000127
Figure PCTKR2023003724-appb-img-000127
<B-5a> <E-1a> <E-1> <B-5a> <E-1a> <E-1>
상기 합성예 2-5에서 사용한 <B-5b> 대신 <E-1a>를 사용한 것을 제외하고는 동일한 방법으로 합성하여 <E-1>을 얻었다. (수율 57.2%)<E-1> was obtained by synthesis in the same manner, except that <E-1a> was used instead of <B-5b> used in Synthesis Example 2-5. (yield 57.2%)
합성예 5-2 : [화합물 196]의 합성Synthesis Example 5-2: Synthesis of [Compound 196]
Figure PCTKR2023003724-appb-img-000128
Figure PCTKR2023003724-appb-img-000128
<B-4> <E-1> [화합물 196]<B-4> <E-1> [Compound 196]
상기 합성예 1-5에서 사용한 <A-4> 대신 <B-4>를 사용하고, <A-5a> 대신 <E-1>을 사용한 것을 제외하고는 동일한 방법으로 합성하여 [화합물 196]을 얻었다. (수율 45.9%)[Compound 196] was synthesized in the same manner, except that <B-4> was used instead of <A-4> used in Synthesis Example 1-5, and <E-1> was used instead of <A-5a>. got it (yield 45.9%)
MS (MALDI-TOF) : m/z 602.20 [M+]MS (MALDI-TOF): m/z 602.20 [M + ]
합성예 6. [화합물 197]의 제조Synthesis Example 6. Preparation of [Compound 197]
합성예 6-1 : F-1의 합성Synthesis Example 6-1: Synthesis of F-1
Figure PCTKR2023003724-appb-img-000129
Figure PCTKR2023003724-appb-img-000129
<A-1a> <F-1a> <F-1> <A-1a> <F-1a> <F-1>
상기 합성예 1-1에서 사용한 <A-1b> 대신 <F-1a>를 사용한 것을 제외하고는 동일한 방법으로 합성하여 <F-1>을 얻었다. (수율 63.8%)<F-1> was obtained by synthesis in the same manner, except that <F-1a> was used instead of <A-1b> used in Synthesis Example 1-1. (yield 63.8%)
합성예 6-2 : F-2의 합성Synthesis Example 6-2: Synthesis of F-2
Figure PCTKR2023003724-appb-img-000130
Figure PCTKR2023003724-appb-img-000130
<F-1> <F-2> <F-1> <F-2>
상기 합성예 2-1에서 사용한 <A-1> 대신 <F-1>을 사용한 것을 제외하고는 동일한 방법으로 합성하여 <F-2>를 얻었다. (수율 48.7%)<F-2> was obtained by synthesis in the same manner, except that <F-1> was used instead of <A-1> used in Synthesis Example 2-1. (yield 48.7%)
합성예 6-3 : F-3의 합성Synthesis Example 6-3: Synthesis of F-3
Figure PCTKR2023003724-appb-img-000131
Figure PCTKR2023003724-appb-img-000131
<F-2> <A-3a> <F-3> <F-2> <A-3a> <F-3>
상기 합성예 1-3에서 사용한 <A-2> 대신 <F-2>를 사용한 것을 제외하고는 동일한 방법으로 합성하여 <F-3>을 얻었다. (수율 65.6%)<F-3> was obtained by synthesis in the same manner, except that <F-2> was used instead of <A-2> used in Synthesis Example 1-3. (yield 65.6%)
합성예 6-4 : F-4의 합성Synthesis Example 6-4: Synthesis of F-4
Figure PCTKR2023003724-appb-img-000132
Figure PCTKR2023003724-appb-img-000132
<F-3> <F-4> <F-3> <F-4>
상기 합성예 3-5에서 사용한 <C-4> 대신 <F-3>을 사용한 것을 제외하고는 동일한 방법으로 합성하여 <F-4>를 얻었다. (수율 77.8%)<F-4> was obtained by synthesis in the same manner, except that <F-3> was used instead of <C-4> used in Synthesis Example 3-5. (yield 77.8%)
합성예 6-5 : [화합물 197]의 합성Synthesis Example 6-5: Synthesis of [Compound 197]
Figure PCTKR2023003724-appb-img-000133
Figure PCTKR2023003724-appb-img-000133
<F-4> <A-5a> [화합물 197]<F-4> <A-5a> [Compound 197]
상기 합성예 1-5에서 사용한 <A-4> 대신 <F-4>를 사용한 것을 제외하고는 동일한 방법으로 합성하여 [화합물 197]을 얻었다. (수율 48.7%)[Compound 197] was obtained by synthesis in the same manner except that <F-4> was used instead of <A-4> used in Synthesis Example 1-5. (yield 48.7%)
MS (MALDI-TOF) : m/z 678.23 [M+]MS (MALDI-TOF): m/z 678.23 [M + ]
합성예 7. [화합물 198]의 제조Synthesis Example 7. Preparation of [Compound 198]
합성예 7-1 : [화합물 198]의 합성Synthesis Example 7-1: Synthesis of [Compound 198]
Figure PCTKR2023003724-appb-img-000134
Figure PCTKR2023003724-appb-img-000134
<A-4> <E-1> [화합물 198]<A-4> <E-1> [Compound 198]
상기 합성예 1-5에서 사용한 <A-5a> 대신 <E-1>을 사용한 것을 제외하고는 동일한 방법으로 합성하여 [화합물 198]을 얻었다. (수율 35.9%)[Compound 198] was obtained by synthesis in the same manner except that <E-1> was used instead of <A-5a> used in Synthesis Example 1-5. (yield 35.9%)
MS (MALDI-TOF) : m/z 602.20 [M+]MS (MALDI-TOF): m/z 602.20 [M + ]
합성예 8. [화합물 201]의 제조Synthesis Example 8. Preparation of [Compound 201]
합성예 8-1 : [화합물 201]의 합성Synthesis Example 8-1: Synthesis of [Compound 201]
Figure PCTKR2023003724-appb-img-000135
Figure PCTKR2023003724-appb-img-000135
<F-4> <E-1> [화합물 201]<F-4> <E-1> [Compound 201]
상기 합성예 1-5에서 사용한 <A-4> 대신 <F-4>를 사용하고, <A-5a> 대신 <E-1>을 사용한 것을 제외하고는 동일한 방법으로 합성하여 [화합물 201]을 얻었다. (수율 35.9%)[Compound 201] was synthesized in the same manner, except that <F-4> was used instead of <A-4> used in Synthesis Example 1-5, and <E-1> was used instead of <A-5a>. got it (yield 35.9%)
MS (MALDI-TOF) : m/z 652.22 [M+]MS (MALDI-TOF): m/z 652.22 [M + ]
합성예 9. [화합물 224]의 제조Synthesis Example 9. Preparation of [Compound 224]
합성예 9-1 : G-1의 합성Synthesis Example 9-1: Synthesis of G-1
Figure PCTKR2023003724-appb-img-000136
Figure PCTKR2023003724-appb-img-000136
<G-1a> <A-3a> <G-1><G-1a> <A-3a> <G-1>
상기 합성예 1-3에서 사용한 <A-2> 대신 <G-1a>를 사용한 것을 제외하고는 동일한 방법으로 합성하여 <G-1>을 얻었다. (수율 95.2%)<G-1> was obtained by synthesis in the same manner, except that <G-1a> was used instead of <A-2> used in Synthesis Example 1-3. (yield 95.2%)
합성예 9-2. G-2의 합성Synthesis Example 9-2. Synthesis of G-2
Figure PCTKR2023003724-appb-img-000137
Figure PCTKR2023003724-appb-img-000137
<G-1> <B-3a> <G-2><G-1> <B-3a> <G-2>
상기 합성예 2-3에서 사용한 <B-2> 대신 <G-1>을 사용한 것을 제외하고는 동일한 방법으로 합성하여 <G-2>를 얻었다. (수율 95.3%)<G-2> was obtained by synthesis in the same manner, except that <G-1> was used instead of <B-2> used in Synthesis Example 2-3. (yield 95.3%)
합성예 9-3 : G-3의 합성Synthesis Example 9-3: Synthesis of G-3
Figure PCTKR2023003724-appb-img-000138
Figure PCTKR2023003724-appb-img-000138
<G-2> <G-3> <G-2> <G-3>
상기 합성예 2-4에서 사용한 <B-3> 대신 <G-2>를 사용한 것을 제외하고는 동일한 방법으로 합성하여 <G-3>을 얻었다. (수율 63.7%)<G-3> was obtained by synthesis in the same manner, except that <G-2> was used instead of <B-3> used in Synthesis Example 2-4. (yield 63.7%)
합성예 9-4 : G-4의 합성Synthesis Example 9-4: Synthesis of G-4
Figure PCTKR2023003724-appb-img-000139
Figure PCTKR2023003724-appb-img-000139
<G-3> <G-4a> <G-4><G-3> <G-4a> <G-4>
상기 합성예 1-5에서 사용한 <A-4> 대신 <G-3>을 사용하고, <A-5a> 대신 <G-4a>를 사용한 것을 제외하고는 동일한 방법으로 합성하여 <G-4>를 얻었다. (수율 65.2%)<G-4> was synthesized in the same manner except that <G-3> was used instead of <A-4> used in Synthesis Example 1-5, and <G-4a> was used instead of <A-5a>. got it (yield 65.2%)
합성예 9-5 : G-5의 합성Synthesis Example 9-5: Synthesis of G-5
Figure PCTKR2023003724-appb-img-000140
Figure PCTKR2023003724-appb-img-000140
<G-5a> <G-5><G-5a> <G-5>
상기 합성예 1-2에서 사용한 <A-1> 대신 <G-5a>를 사용한 것을 제외하고는 동일한 방법으로 합성하여 <G-5>를 얻었다. (수율 77.1%)<G-5> was obtained by synthesis in the same manner, except that <G-5a> was used instead of <A-1> used in Synthesis Example 1-2. (yield 77.1%)
합성예 9-6 : G-6의 합성Synthesis Example 9-6: Synthesis of G-6
Figure PCTKR2023003724-appb-img-000141
Figure PCTKR2023003724-appb-img-000141
<G-5> <A-3a> <G-6> <G-5> <A-3a> <G-6>
상기 합성예 1-3에서 사용한 <A-2> 대신 <G-5>를 사용한 것을 제외하고는 동일한 방법으로 합성하여 <G-6>을 얻었다. (수율 42.5%)<G-6> was obtained by synthesis in the same manner, except that <G-5> was used instead of <A-2> used in Synthesis Example 1-3. (yield 42.5%)
합성예 9-7 : G-7의 합성Synthesis Example 9-7: Synthesis of G-7
Figure PCTKR2023003724-appb-img-000142
Figure PCTKR2023003724-appb-img-000142
<G-6> <G-7> <G-6> <G-7>
상기 합성예 1-4에서 사용한 <A-3> 대신 <G-6>을 사용한 것을 제외하고는 동일한 방법으로 합성하여 <G-7>을 얻었다. (수율 30.5%)<G-7> was obtained by synthesis in the same manner, except that <G-6> was used instead of <A-3> used in Synthesis Example 1-4. (yield 30.5%)
합성예 9-8. [화합물 224]의 합성Synthesis Example 9-8. Synthesis of [Compound 224]
Figure PCTKR2023003724-appb-img-000143
Figure PCTKR2023003724-appb-img-000143
<G-7> <G-4> [화합물 224]<G-7> <G-4> [Compound 224]
상기 합성예 1-5에서 사용한 <A-4> 대신 <G-7>을 사용하고, <A-5a> 대신 <G-4>를 사용한 것을 제외하고는 동일한 방법으로 합성하여 [화합물 224]를 얻었다. (수율 25.1%)[Compound 224] was synthesized in the same manner, except that <G-7> was used instead of <A-4> used in Synthesis Example 1-5, and <G-4> was used instead of <A-5a>. got it (yield 25.1%)
MS (MALDI-TOF) : m/z 770.28 [M+]MS (MALDI-TOF): m/z 770.28 [M + ]
실시예 1 내지 12 : 유기발광소자의 제조Examples 1 to 12: Preparation of organic light-emitting devices
ITO 글래스의 발광면적이 2 mm × 2 mm 크기가 되도록 패터닝한 후 세정하였다. 상기 ITO 글래스를 진공 챔버에 장착한 후 베이스 압력이 1 × 10-6 torr가 되도록 한 후 상기 ITO 위에 HATCN (50 Å), NPD (1500 Å) 순으로 성막한다. 발광층으로서, 본 발명에 따른 호스트 화합물을 [RH]와 1:1혼합 및 도판트 화합물 [RD]를 5 wt% 혼합하여 성막 (400 Å)한 다음, 전자 수송 및 전자 주입층으로 ET : Liq = 1:1 (300 Å)를 차례로 성막하고, Liq (10 Å), Al (1000 Å)을 성막하여 유기발광소자를 제작하였다. 상기 유기발광소자의 발광특성은 0.4 mA에서 측정을 하였다.The ITO glass was patterned so that the light emitting area was 2 mm × 2 mm in size and then cleaned. After mounting the ITO glass in a vacuum chamber, the base pressure is set to 1 × 10 -6 torr, and then HATCN (50 Å) and NPD (1500 Å) are formed on the ITO in that order. As a light-emitting layer, a host compound according to the present invention was mixed 1:1 with [RH] and a dopant compound [RD] was mixed at 5 wt% to form a film (400 Å), and then as an electron transport and electron injection layer, ET: Liq = An organic light-emitting device was manufactured by forming a 1:1 (300 Å) film sequentially, followed by Liq (10 Å) and Al (1000 Å). The emission characteristics of the organic light emitting device were measured at 0.4 mA.
[HATCN] [NPD] [RD][HATCN] [NPD] [RD]
Figure PCTKR2023003724-appb-img-000144
Figure PCTKR2023003724-appb-img-000144
[RH] [ET] [Liq] [RH] [ET] [Liq]
Figure PCTKR2023003724-appb-img-000145
Figure PCTKR2023003724-appb-img-000145
비교예 1 내지 2Comparative Examples 1 to 2
비교예를 위한 유기발광소자는 상기 실시예의 소자구조에서 호스트 화합물로 본 발명에 따른 화합물 대신에 하기 [RH-1] 및 [RH-2]를 제외하고는 동일하게 유기발광소자를 제작하였으며, 상기 유기발광소자의 발광 특성은 0.4 mA에서 측정하였다. 상기 [RH-1] 및 [RH-2]의 구조는 아래와 같다.The organic light emitting device for the comparative example was manufactured in the same manner as the device structure of the above example, except for the following [RH-1] and [RH-2] instead of the compound according to the present invention as the host compound. The emission characteristics of the organic light emitting device were measured at 0.4 mA. The structures of [RH-1] and [RH-2] are as follows.
[RH-1] [RH-2] [RH-1] [RH-2]
Figure PCTKR2023003724-appb-img-000146
Figure PCTKR2023003724-appb-img-000146
구 분division 호스트host 구동전압
(V)driving voltage
(V) 		전류효율
(cd/A)Current efficiency
(cd/A) 		수명
(T95, hr)life span
(T95, hr) 		발광색
(color)Luminous color
(color)
실시예 1Example 1 182182 3.473.47 24.924.9 270270 적색Red
실시예 2Example 2 186186 3.313.31 24.524.5 210210 적색Red
실시예 3Example 3 187187 3.303.30 25.225.2 200200 적색Red
실시예 4Example 4 190190 3.473.47 26.326.3 252252 적색Red
실시예 5Example 5 194194 3.363.36 24.424.4 269269 적색Red
실시예 6Example 6 196196 3.393.39 24.724.7 244244 적색Red
실시예 7Example 7 197197 3.413.41 24.524.5 291291 적색Red
실시예 8Example 8 198198 3.423.42 24.324.3 228228 적색Red
실시예 9Example 9 201201 3.413.41 23.923.9 290290 적색Red
실시예 10Example 10 224224 3.333.33 25.225.2 292292 적색Red
실시예 11 Example 11 238238 3.313.31 24.924.9 233233 적색Red
실시예 12Example 12 239239 3.423.42 25.425.4 205 205 적색Red
비교예 1Comparative Example 1 RH-1RH-1 4.754.75 19.219.2 145145 적색Red
비교예 2Comparative Example 2 RH-2RH-2 4.324.32 15.015.0 136136 적색Red
상기 [표 1]에서 보는 바와 같이 본 발명에 의한 유기 발광 화합물은 종래기술에 따른 비교예 1 내지 비교예 2에 비하여 보다 저전압 구동, 고효율 및 장수명 특성이 모두 고르게 양호한 성질을 가지는 것으로 나타남으로, 유기발광소자로서 응용가능성 높은 것을 나타내고 있다. As shown in [Table 1], the organic light-emitting compound according to the present invention appears to have better low-voltage driving, high efficiency, and long life characteristics compared to Comparative Examples 1 and 2 according to the prior art. It shows high applicability as a light-emitting device.
본 발명에 따른 상기 [화학식 A] 또는 [화학식 A]로 표시되는 방향족 헤테로고리 화합물은 유기발광소자내 발광층의 인광 호스트 물질로 이용하는 경우에, 종래기술에 따른 유기발광소자에 비하여 보다 저전압 구동, 고효율 및 장수명의 특성을 나타내므로, 유기발광소자 및 디스플레이 분야 등의 산업 분야에서 산업상 이용가능성이 높다.When the aromatic heterocyclic compound represented by [Formula A] or [Formula A] according to the present invention is used as a phosphorescent host material for a light-emitting layer in an organic light-emitting device, it operates at a lower voltage and has higher efficiency than the organic light-emitting device according to the prior art. and long lifespan, it has high industrial applicability in industrial fields such as organic light-emitting devices and displays.

Claims (13)

  1. 하기 [화학식 A] 또는 [화학식 B]로 표시되는 방향족 헤테로고리 화합물.An aromatic heterocyclic compound represented by [Formula A] or [Formula B] below.
    [화학식 A] [Formula A]
    Figure PCTKR2023003724-appb-img-000147
    Figure PCTKR2023003724-appb-img-000147
    [화학식 B] [Formula B]
    Figure PCTKR2023003724-appb-img-000148
    Figure PCTKR2023003724-appb-img-000148
    상기 [화학식 A] 및 [화학식 B]에서,In [Formula A] and [Formula B],
    상기 X1은 NR4, O 및 S 중에서 선택되는 어느 하나이며,The X 1 is any one selected from NR 4 , O and S,
    상기 Z1 내지 Z8은 서로 동일하거나 상이하고, 각각 독립적으로 CR 또는 N 중에서 선택되는 어느 하나이며,Z 1 to Z 8 are the same or different from each other, and are each independently selected from CR or N,
    상기 Z1 내지 Z8이 복수의 CR을 포함하는 경우에 각각의 R은 서로 동일하거나 상이하고,When Z 1 to Z 8 include a plurality of CR, each R is the same as or different from each other,
    상기 Z3 내지 Z6 중 하나는 연결기 L과 결합하는 단일결합을 포함하는 탄소원자이며,One of Z 3 to Z 6 is a carbon atom containing a single bond bonded to the linking group L,
    상기 R, R1 내지 R4는 서로 동일하거나 상이하고, 각각 독립적으로 수소, 중수소, 치환 또는 비치환된 탄소수 1 내지 30의 알킬기, 치환 또는 비치환된 탄소수 2 내지 30의 알케닐기, 치환 또는 비치환된 탄소수 2 내지 20의 알키닐기, 치환 또는 비치환된 탄소수 6 내지 50의 아릴기, 치환 또는 비치환된 탄소수 3 내지 30의 시클로알킬기, 치환 또는 비치환된 탄소수 5 내지 30의 시클로알케닐기, 치환 또는 비치환된 탄소수 2 내지 30의 헤테로시클로알킬기, 치환 또는 비치환된 탄소수 2 내지 50의 헤테로알킬기, 치환 또는 비치환된 탄소수 2 내지 50의 헤테로아릴기, 치환 또는 비치환된 탄소수 7 내지 30의 방향족 탄화수소 고리가 축합된 시클로알킬기, 치환 또는 비치환된 탄소수 5 내지 30의 방향족 헤테로고리가 축합된 시클로알킬기, 치환 또는 비치환된 탄소수 6 내지 30의 방향족 탄화수소 고리가 축합된 헤테로시클로알킬기, 치환 또는 비치환된 탄소수 8 내지 30의 지방족 탄화수소 고리가 축합된 아릴기, 치환 또는 비치환된 탄소수 5 내지 30의 지방족 탄화수소 고리가 축합된 헤테로아릴기, 치환 또는 비치환된 탄소수 1 내지 30의 알콕시기, 치환 또는 비치환된 탄소수 6 내지 30의 아릴옥시기, 치환 또는 비치환된 탄소수 3 내지 30의 시클로알킬옥시기, 치환 또는 비치환된 탄소수 2 내지 30의 헤테로아릴옥시기, 치환 또는 비치환된 탄소수 1 내지 30의 알킬티오기, 치환 또는 비치환된 탄소수 6 내지 30의 아릴티오기, 치환 또는 비치환된 탄소수 3 내지 30의 시클로알킬티오기, 치환 또는 비치환된 탄소수 2 내지 30의 헤테로아릴티오기, 치환 또는 비치환된 탄소수 0 내지 30의 아민기, 치환 또는 비치환된 탄소수 0 내지 30의 실릴기, 탄소수 0 내지 30의 저마늄기, 니트로기, 시아노기, 할로겐기 중에서 선택되는 어느 하나이며, R, R 1 to R 4 are the same or different from each other, and are each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, substituted or unsubstituted A substituted or unsubstituted alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted cycloalkenyl group having 5 to 30 carbon atoms, Substituted or unsubstituted heterocycloalkyl group having 2 to 30 carbon atoms, substituted or unsubstituted heteroalkyl group having 2 to 50 carbon atoms, substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms, substituted or unsubstituted heteroaryl group having 7 to 30 carbon atoms A cycloalkyl group in which an aromatic hydrocarbon ring is condensed, a cycloalkyl group in which a substituted or unsubstituted aromatic heterocycle of 5 to 30 carbon atoms is condensed, a heterocycloalkyl group in which a substituted or unsubstituted aromatic hydrocarbon ring of 6 to 30 carbon atoms is condensed, substituted Or an aryl group in which an unsubstituted aliphatic hydrocarbon ring having 8 to 30 carbon atoms is condensed, a heteroaryl group in which a substituted or unsubstituted aliphatic hydrocarbon ring in the carbon number of 5 to 30 is condensed, or a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms. , a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted cycloalkyloxy group having 3 to 30 carbon atoms, a substituted or unsubstituted heteroaryloxy group having 2 to 30 carbon atoms, a substituted or unsubstituted Alkylthio group with 1 to 30 carbon atoms, substituted or unsubstituted arylthio group with 6 to 30 carbon atoms, substituted or unsubstituted cycloalkylthio group with 3 to 30 carbon atoms, substituted or unsubstituted heteroaryl with 2 to 30 carbon atoms Any one selected from a thio group, a substituted or unsubstituted amine group with 0 to 30 carbon atoms, a substituted or unsubstituted silyl group with 0 to 30 carbon atoms, a germanium group with 0 to 30 carbon atoms, a nitro group, a cyano group, or a halogen group. and
    상기 Z1 내지 Z8이 복수의 CR을 포함하는 경우에 서로 인접한 각각의 R은 서로 연결되어 지환족 또는 방향족의 단일환 또는 다환의 고리를 추가 형성할 수 있고, 상기 형성된 지환족, 방향족의 단일환 또는 다환 고리의 탄소원자는 N, S 및 O 중에서 선택되는 어느 하나 이상의 헤테로원자로 치환될 수 있으며,When Z 1 to Z 8 include a plurality of CR, each R adjacent to each other may be connected to each other to further form an alicyclic or aromatic monocyclic or polycyclic ring, and the formed alicyclic or aromatic ring may be The carbon atom of the monocyclic or polycyclic ring may be substituted with one or more heteroatoms selected from N, S and O,
    상기 R2 및 R3는 서로 연결되어 지환족 또는 방향족의 단일환 또는 다환의 고리를 추가 형성할 수 있으며,R 2 and R 3 may be connected to each other to further form an alicyclic or aromatic monocyclic or polycyclic ring,
    상기 L은 단일결합, 치환 또는 비치환된 탄소수 6 내지 50의 아릴렌기 및 치환 또는 비치환된 탄소수 2 내지 50의 헤테로아릴렌기 중에서 선택되는 어느 하나이고,Wherein L is a single bond, a substituted or unsubstituted arylene group having 6 to 50 carbon atoms and a substituted or unsubstituted heteroarylene group having 2 to 50 carbon atoms,
    상기 [화학식 A] 및 [화학식 B] 내 '치환 또는 비치환된'에서의 '치환'은 중수소, 시아노기, 할로겐기, 히드록시기, 니트로기, 탄소수 1 내지 24의 알킬기, 탄소수 1 내지 24의 할로겐화된 알킬기, 탄소수 3 내지 30의 시클로알킬기, 탄소수 2 내지 24의 알케닐기, 탄소수 2 내지 24의 알키닐기, 탄소수 1 내지 24의 헤테로알킬기, 탄소수 6 내지 24의 아릴기, 탄소수 7 내지 24의 아릴알킬기, 탄소수 7 내지 24의 알킬아릴기, 탄소수 2 내지 24의 헤테로아릴기, 탄소수 2 내지 24의 헤테로아릴알킬기, 탄소수 7 내지 24의, 방향족 탄화수소 고리가 축합된 시클로알킬기, 탄소수 5 내지 24의, 방향족 헤테로고리가 축합된 시클로알킬기, 탄소수 6 내지 24의, 방향족 탄화수소 고리가 축합된 헤테로시클로알킬기, 탄소수 8 내지 24의, 지방족 탄화수소 고리가 축합된 아릴기, 탄소수 5 내지 24의, 지방족 탄화수소 고리가 축합된 헤테로아릴기, 탄소수 1 내지 24의 알콕시기, 탄소수 1 내지 24의 아민기, 탄소수 1 내지 24의 실릴기, 탄소수 1 내지 24의 저마늄기, 탄소수 6 내지 24의 아릴옥시기, 탄소수 6 내지 24의 아릴티오닐기로 이루어진 군에서 선택된 1개 이상의 치환기로 치환되는 것을 의미하며, 상기 각각의 치환기내 하나 이상의 수소는 중수소로 치환가능하다.'Substitution' in 'substituted or unsubstituted' in [Formula A] and [Formula B] means deuterium, cyano group, halogen group, hydroxy group, nitro group, alkyl group with 1 to 24 carbon atoms, halogenation with 1 to 24 carbon atoms. alkyl group, cycloalkyl group with 3 to 30 carbon atoms, alkenyl group with 2 to 24 carbon atoms, alkynyl group with 2 to 24 carbon atoms, heteroalkyl group with 1 to 24 carbon atoms, aryl group with 6 to 24 carbon atoms, arylalkyl group with 7 to 24 carbon atoms , an alkylaryl group having 7 to 24 carbon atoms, a heteroaryl group having 2 to 24 carbon atoms, a heteroarylalkyl group having 2 to 24 carbon atoms, a cycloalkyl group in which an aromatic hydrocarbon ring is condensed, having 7 to 24 carbon atoms, and an aromatic group having 5 to 24 carbon atoms. Cycloalkyl group with a condensed hetero ring, a heterocycloalkyl group with a condensed aromatic hydrocarbon ring having 6 to 24 carbon atoms, an aryl group with a condensed aliphatic hydrocarbon ring with 8 to 24 carbon atoms, and a condensed aliphatic hydrocarbon ring with 5 to 24 carbon atoms. heteroaryl group, alkoxy group of 1 to 24 carbon atoms, amine group of 1 to 24 carbon atoms, silyl group of 1 to 24 carbon atoms, germanium group of 1 to 24 carbon atoms, aryloxy group of 6 to 24 carbon atoms, 6 to 24 carbon atoms means being substituted with one or more substituents selected from the group consisting of arylthionyl groups, and one or more hydrogens in each substituent can be replaced with deuterium.
  2. 제 1 항에 있어서,According to claim 1,
    상기 [화학식 A] 및 [화학식 B] 내 X1이 O 또는 S인 것을 특징으로 하는 방향족 헤테로고리 화합물.An aromatic heterocyclic compound in which X 1 in [Formula A] and [Formula B] is O or S.
  3. 제 1 항에 있어서,According to claim 1,
    상기 [화학식 A] 및 [화학식 B] 내 R1 내지 R3 중 적어도 하나는 탄소수 6 내지 24의 아릴기인 것을 특징으로 하는 방향족 헤테로고리 화합물.An aromatic heterocyclic compound, wherein at least one of R 1 to R 3 in [Formula A] and [Formula B] is an aryl group having 6 to 24 carbon atoms.
  4. 제 1 항에 있어서,According to claim 1,
    상기 [화학식 A] 및 [화학식 B] 내 R1 내지 R3 중 적어도 하나는 하기 [구조식 A]로 표시되는 치환기 인 것을 특징으로 하는 방향족 헤테로고리 화합물.An aromatic heterocyclic compound, wherein at least one of R 1 to R 3 in [Formula A] and [Formula B] is a substituent represented by the following [Structural Formula A].
    [구조식 A][Structural Formula A]
    Figure PCTKR2023003724-appb-img-000149
    Figure PCTKR2023003724-appb-img-000149
    [구조식 Q-1] [구조식 Q-2] [구조식 Q-3][Structural formula Q-1] [Structural formula Q-2] [Structural formula Q-3]
    Figure PCTKR2023003724-appb-img-000150
    Figure PCTKR2023003724-appb-img-000150
    상기 [구조식 A]에서,In the above [structural formula A],
    상기 Q는 아래의 구조식 Q-1 내지 Q-3 중에서 선택되는 어느 하나의 고리이고,Wherein Q is any one ring selected from the structural formulas Q-1 to Q-3 below,
    상기 Q가 구조식 Q-1인 경우, 상기 구조식 Q-1 내 이웃한 탄소 원자인 R17과 R18, R18과 R19 및 R19와 R20 중 한 쌍의 치환기는 구조식 A 내 방향족 탄소원자 f 및 방향족 탄소원자 g와 축합되어 6원환의 고리를 형성하는 단일결합이고,When Q is structural formula Q-1, a pair of substituents among the neighboring carbon atoms R 17 and R 18 , R 18 and R 19 , and R 19 and R 20 in structural formula Q-1 are aromatic carbon atoms in structural formula A. It is a single bond that is condensed with f and the aromatic carbon atom g to form a 6-membered ring,
    상기 Q가 구조식 Q-2 인 경우, 상기 구조식 Q-2 내 이웃한 탄소 원자인 R25와 R26, R27과 R28, R28과 R29 및 R29와 R30 중 한 쌍의 치환기는 구조식 A 내 방향족 탄소원자 f 및 방향족 탄소원자 g와 축합되어 6원환의 고리를 형성하는 단일결합이며, When Q is the structural formula Q-2, a pair of substituents among the neighboring carbon atoms in the structural formula Q-2, R 25 and R 26 , R 27 and R 28 , R 28 and R 29 , and R 29 and R 30 It is a single bond that is condensed with the aromatic carbon atom f and the aromatic carbon atom g in structural formula A to form a six-membered ring,
    상기 Q가 구조식 Q-3인 경우, 상기 구조식 Q-3 내 이웃한 탄소 원자인 R35와 R36, R36과 R37 및 R37과 R38 중 한 쌍의 치환기는 구조식 A 내 방향족 탄소원자 f 및 방향족 탄소원자 g와 축합되어 6원환의 고리를 형성하는 단일결합이며, When Q is structural formula Q-3, a pair of substituents among the neighboring carbon atoms R 35 and R 36 , R 36 and R 37 , and R 37 and R 38 in structural formula Q-3 are aromatic carbon atoms in structural formula A. It is a single bond that is condensed with f and the aromatic carbon atom g to form a 6-membered ring,
    상기 치환기 R11 내지 R16 및, R17 내지 R44 중 고리를 형성하는 단일결합이 아닌 나머지 치환기는 서로 동일하거나 상이하며, 각각 독립적으로 수소, 중수소, 중수소 치환되거나 비치환된 탄소수 1 내지 24의 알킬기, 중수소 치환되거나 비치환된 탄소수 1 내지 24의 할로겐화된 알킬기, 중수소 치환되거나 비치환된 탄소수 3 내지 30의 시클로알킬기, 중수소 치환되거나 비치환된 탄소수 2 내지 24의 알케닐기, 중수소 치환되거나 비치환된 탄소수 2 내지 24의 알키닐기, 중수소 치환되거나 비치환된 탄소수 1 내지 24의 헤테로알킬기, 중수소 치환되거나 비치환된 탄소수 6 내지 24의 아릴기, 중수소 치환되거나 비치환된 탄소수 7 내지 24의 아릴알킬기, 중수소 치환되거나 비치환된 탄소수 7 내지 24의 알킬아릴기, 중수소 치환되거나 비치환된 탄소수 2 내지 24의 헤테로아릴기, 중수소 치환되거나 비치환된 탄소수 2 내지 24의 헤테로아릴알킬기, 중수소 치환되거나 비치환된 탄소수 7 내지 24의, 방향족 탄화수소 고리가 축합된 시클로알킬기, 중수소 치환되거나 비치환된 탄소수 5 내지 24의, 방향족 헤테로고리가 축합된 시클로알킬기, 중수소 치환되거나 비치환된 탄소수 6 내지 24의, 방향족 탄화수소 고리가 축합된 헤테로시클로알킬기, 중수소 치환되거나 비치환된 탄소수 8 내지 24의, 지방족 탄화수소 고리가 축합된 아릴기, 중수소 치환되거나 비치환된 탄소수 5 내지 24의, 지방족 탄화수소 고리가 축합된 헤테로아릴기, 중수소 치환되거나 비치환된 탄소수 1 내지 24의 알콕시기, 중수소 치환되거나 비치환된 탄소수 1 내지 24의 아민기, 중수소 치환되거나 비치환된 탄소수 1 내지 24의 실릴기, 중수소 치환되거나 비치환된 탄소수 1 내지 24의 저마늄기, 중수소 치환되거나 비치환된 탄소수 6 내지 24의 아릴옥시기, 중수소 치환되거나 비치환된 탄소수 6 내지 24의 아릴티오닐기 중에서 선택되는 어느 하나이되,Among the substituents R 11 to R 16 and R 17 to R 44 , the remaining substituents that are not a single bond forming a ring are the same or different from each other, and each independently represents hydrogen, deuterium, deuterium, substituted or unsubstituted carbon atoms of 1 to 24. Alkyl group, deuterated or unsubstituted halogenated alkyl group having 1 to 24 carbon atoms, deuterated or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, deuterated or unsubstituted alkenyl group having 2 to 24 carbon atoms, deuterium substituted or unsubstituted Alkynyl group having 2 to 24 carbon atoms, deuterated or unsubstituted heteroalkyl group having 1 to 24 carbon atoms, deuterated or unsubstituted aryl group having 6 to 24 carbon atoms, deuterium substituted or unsubstituted arylalkyl group having 7 to 24 carbon atoms , deuterium substituted or unsubstituted alkylaryl group having 7 to 24 carbon atoms, deuterium substituted or unsubstituted heteroaryl group having 2 to 24 carbon atoms, deuterium substituted or unsubstituted heteroarylalkyl group having 2 to 24 carbon atoms, deuterated or unsubstituted A cycloalkyl group in which a ringed C7-C24 aromatic hydrocarbon ring is condensed, a deuterium-substituted or unsubstituted C5-C24 aromatic heterocycle-condensed cycloalkyl group, a deuterium-substituted or unsubstituted C6-C24 ring, Heterocycloalkyl group in which an aromatic hydrocarbon ring is condensed, an aryl group in which a deuterium-substituted or unsubstituted aliphatic hydrocarbon ring having 8 to 24 carbon atoms is condensed, a hetero group in which a deuterium-substituted or unsubstituted aliphatic hydrocarbon ring is condensed in 5 to 24 carbon atoms. Aryl group, deuterium-substituted or unsubstituted alkoxy group of 1 to 24 carbon atoms, deuterium-substituted or unsubstituted amine group of 1 to 24 carbon atoms, deuterium-substituted or unsubstituted silyl group of 1 to 24 carbon atoms, deuterium-substituted or unsubstituted Any one selected from the group consisting of a germanium group having 1 to 24 carbon atoms, a deuterium-substituted or unsubstituted aryloxy group having 6 to 24 carbon atoms, and a deuterium-substituted or unsubstituted arylthionyl group having 6 to 24 carbon atoms,
    상기 구조식 A내 Q가 구조식 Q-1인 경우, 구조식 A내 R11 내지 R16 중 하나, 또는 구조식 Q-1내 R17 내지 R24 중 하나는 R1 내지 R3 와 결합되는 탄소원자 또는 질소원자에 결합되는 단일 결합이고, When Q in the structural formula A is structural formula Q-1, one of R 11 to R 16 in the structural formula A, or Within structural formula Q-1 One of R 17 to R 24 is a single bond bonded to the carbon atom or nitrogen atom bonded to R 1 to R 3 ,
    상기 구조식 A내 Q가 구조식 Q-2인 경우, 구조식 A내 R11 내지 R16 중 하나, 또는 구조식 Q-2내 R25 내지 R34 중 하나는 R1 내지 R3 와 결합되는 탄소원자 또는 질소원자에 결합되는 단일 결합이며, When Q in the structural formula A is structural formula Q-2, one of R 11 to R 16 in the structural formula A, or Within structural formula Q-2 One of R 25 to R 34 is a single bond bonded to the carbon atom or nitrogen atom bonded to R 1 to R 3 ,
    상기 구조식 A내 Q가 구조식 Q-3인 경우, 구조식 A내 R11 내지 R16 중 하나, 또는 구조식 Q-3내 R35 내지 R42 중 하나는 R1 내지 R3 와 결합되는 탄소원자 또는 질소원자에 결합되는 단일 결합이고,When Q in the structural formula A is structural formula Q-3, one of R 11 to R 16 in the structural formula A, or Within structural formula Q-3 One of R 35 to R 42 is a single bond bonded to the carbon atom or nitrogen atom bonded to R 1 to R 3 ,
    상기 R43 및 R44는 서로 연결되어 지환족 또는 방향족의 단일환 또는 다환의 고리를 추가 형성할 수 있다.R 43 and R 44 may be connected to each other to further form an alicyclic or aromatic monocyclic or polycyclic ring.
  5. 제 4 항에 있어서,According to claim 4,
    상기 [구조식 A]는 하기 [구조식 A-1] 내지 [구조식 A-15] 중에서 선택되는 어느 하나인 것을 특징으로 하는 방향족 헤테로고리 화합물.The [Structural Formula A] is an aromatic heterocyclic compound selected from the following [Structural Formula A-1] to [Structural Formula A-15].
    [구조식 A-1] [구조식 A-2][Structural Formula A-1] [Structural Formula A-2]
    Figure PCTKR2023003724-appb-img-000151
    Figure PCTKR2023003724-appb-img-000151
    [구조식 A-3] [구조식 A-4][Structural Formula A-3] [Structural Formula A-4]
    Figure PCTKR2023003724-appb-img-000152
    Figure PCTKR2023003724-appb-img-000152
    [구조식 A-5] [구조식 A-6][Structural Formula A-5] [Structural Formula A-6]
    Figure PCTKR2023003724-appb-img-000153
    Figure PCTKR2023003724-appb-img-000153
    [구조식 A-7] [구조식 A-8][Structural Formula A-7] [Structural Formula A-8]
    Figure PCTKR2023003724-appb-img-000154
    Figure PCTKR2023003724-appb-img-000154
    [구조식 A-9] [구조식 A-10][Structural Formula A-9] [Structural Formula A-10]
    Figure PCTKR2023003724-appb-img-000155
    Figure PCTKR2023003724-appb-img-000155
    [구조식 A-11] [구조식 A-12][Structural Formula A-11] [Structural Formula A-12]
    Figure PCTKR2023003724-appb-img-000156
    Figure PCTKR2023003724-appb-img-000156
    [구조식 A-13] [구조식 A-14][Structural Formula A-13] [Structural Formula A-14]
    Figure PCTKR2023003724-appb-img-000157
    Figure PCTKR2023003724-appb-img-000157
    [구조식 A-15][Structural Formula A-15]
    Figure PCTKR2023003724-appb-img-000158
    Figure PCTKR2023003724-appb-img-000158
    상기 [구조식 A-1] 내지 [구조식 A-15]에서, 치환기 R11 내지 R44는 상기 제4항에서 정의한 바와 동일하다.In [Structural Formula A-1] to [Structural Formula A-15], substituents R 11 to R 44 are the same as defined in paragraph 4 above.
  6. 제 4 항에 있어서,According to claim 4,
    상기 [화학식 A] 및 [화학식 B] 내 R1 내지 R3 중 적어도 하나는 [구조식 A]로 표시되는 치환기 인 것을 특징으로 하는 방향족 헤테로고리 화합물.An aromatic heterocyclic compound, wherein at least one of R 1 to R 3 in [Formula A] and [Formula B] is a substituent represented by [Structural Formula A].
  7. 제 1 항에 있어서,According to claim 1,
    상기 화학식 A내 치환기 R1은 치환 또는 비치환된 페닐기, 치환 또는 비치환된 나프틸기, 치환 또는 비치환된 페난트릴기 중에서 선택되는 어느 하나인 것을 특징으로 하는 방향족 헤테로고리 화합물.The substituent R 1 in Formula A is an aromatic heterocyclic compound, characterized in that any one selected from a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, and a substituted or unsubstituted phenanthryl group.
  8. 제 1 항에 있어서,According to claim 1,
    상기 [화학식 A] 또는 [화학식 B]로 표시되는 화합물은 하기 <1> 내지 <240>으로 표시되는 군으로부터 선택되는 어느 하나의 화합물인 것을 특징으로 하는 방향족 헤테로고리 화합물.The compound represented by [Formula A] or [Formula B] is an aromatic heterocyclic compound, characterized in that it is any one compound selected from the group represented by <1> to <240> below.
    Figure PCTKR2023003724-appb-img-000159
    Figure PCTKR2023003724-appb-img-000159
    1 2 31 2 3
    Figure PCTKR2023003724-appb-img-000160
    Figure PCTKR2023003724-appb-img-000160
    4 5 64 5 6
    Figure PCTKR2023003724-appb-img-000161
    Figure PCTKR2023003724-appb-img-000161
    7 8 97 8 9
    Figure PCTKR2023003724-appb-img-000162
    Figure PCTKR2023003724-appb-img-000162
    10 11 1210 11 12
    Figure PCTKR2023003724-appb-img-000163
    Figure PCTKR2023003724-appb-img-000163
    13 14 1513 14 15
    Figure PCTKR2023003724-appb-img-000164
    Figure PCTKR2023003724-appb-img-000164
    16 17 1816 17 18
    Figure PCTKR2023003724-appb-img-000165
    Figure PCTKR2023003724-appb-img-000165
    19 20 2119 20 21
    Figure PCTKR2023003724-appb-img-000166
    Figure PCTKR2023003724-appb-img-000166
    22 23 2422 23 24
    Figure PCTKR2023003724-appb-img-000167
    Figure PCTKR2023003724-appb-img-000167
    25 26 2725 26 27
    Figure PCTKR2023003724-appb-img-000168
    Figure PCTKR2023003724-appb-img-000168
    28 29 3028 29 30
    Figure PCTKR2023003724-appb-img-000169
    Figure PCTKR2023003724-appb-img-000169
    31 32 3331 32 33
    Figure PCTKR2023003724-appb-img-000170
    Figure PCTKR2023003724-appb-img-000170
    34 35 3634 35 36
    Figure PCTKR2023003724-appb-img-000171
    Figure PCTKR2023003724-appb-img-000171
    37 38 3937 38 39
    Figure PCTKR2023003724-appb-img-000172
    Figure PCTKR2023003724-appb-img-000172
    40 41 4240 41 42
    Figure PCTKR2023003724-appb-img-000173
    Figure PCTKR2023003724-appb-img-000173
    43 44 4543 44 45
    Figure PCTKR2023003724-appb-img-000174
    Figure PCTKR2023003724-appb-img-000174
    46 47 4846 47 48
    Figure PCTKR2023003724-appb-img-000175
    Figure PCTKR2023003724-appb-img-000175
    49 50 5149 50 51
    Figure PCTKR2023003724-appb-img-000176
    Figure PCTKR2023003724-appb-img-000176
    52 53 5452 53 54
    Figure PCTKR2023003724-appb-img-000177
    Figure PCTKR2023003724-appb-img-000177
    55 56 5755 56 57
    Figure PCTKR2023003724-appb-img-000178
    Figure PCTKR2023003724-appb-img-000178
    58 59 6058 59 60
    Figure PCTKR2023003724-appb-img-000179
    Figure PCTKR2023003724-appb-img-000179
    61 62 6361 62 63
    Figure PCTKR2023003724-appb-img-000180
    Figure PCTKR2023003724-appb-img-000180
    64 65 6664 65 66
    Figure PCTKR2023003724-appb-img-000181
    Figure PCTKR2023003724-appb-img-000181
    67 68 6967 68 69
    Figure PCTKR2023003724-appb-img-000182
    Figure PCTKR2023003724-appb-img-000182
    70 71 7270 71 72
    Figure PCTKR2023003724-appb-img-000183
    Figure PCTKR2023003724-appb-img-000183
    73 74 7573 74 75
    Figure PCTKR2023003724-appb-img-000184
    Figure PCTKR2023003724-appb-img-000184
    76 77 7876 77 78
    Figure PCTKR2023003724-appb-img-000185
    Figure PCTKR2023003724-appb-img-000185
    79 80 8179 80 81
    Figure PCTKR2023003724-appb-img-000186
    Figure PCTKR2023003724-appb-img-000186
    82 83 8482 83 84
    Figure PCTKR2023003724-appb-img-000187
    Figure PCTKR2023003724-appb-img-000187
    85 86 8785 86 87
    Figure PCTKR2023003724-appb-img-000188
    Figure PCTKR2023003724-appb-img-000188
    88 89 9088 89 90
    Figure PCTKR2023003724-appb-img-000189
    Figure PCTKR2023003724-appb-img-000189
    91 92 9391 92 93
    Figure PCTKR2023003724-appb-img-000190
    Figure PCTKR2023003724-appb-img-000190
    94 95 9694 95 96
    Figure PCTKR2023003724-appb-img-000191
    Figure PCTKR2023003724-appb-img-000191
    97 98 9997 98 99
    Figure PCTKR2023003724-appb-img-000192
    Figure PCTKR2023003724-appb-img-000192
    100 101 102100 101 102
    Figure PCTKR2023003724-appb-img-000193
    Figure PCTKR2023003724-appb-img-000193
    103 104 105103 104 105
    Figure PCTKR2023003724-appb-img-000194
    Figure PCTKR2023003724-appb-img-000194
    106 107 108106 107 108
    Figure PCTKR2023003724-appb-img-000195
    Figure PCTKR2023003724-appb-img-000195
    109 110 111109 110 111
    Figure PCTKR2023003724-appb-img-000196
    Figure PCTKR2023003724-appb-img-000196
    112 113 114112 113 114
    Figure PCTKR2023003724-appb-img-000197
    Figure PCTKR2023003724-appb-img-000197
    115 116 117115 116 117
    Figure PCTKR2023003724-appb-img-000198
    Figure PCTKR2023003724-appb-img-000198
    118 119 120118 119 120
    Figure PCTKR2023003724-appb-img-000199
    Figure PCTKR2023003724-appb-img-000199
    121 122 123121 122 123
    Figure PCTKR2023003724-appb-img-000200
    Figure PCTKR2023003724-appb-img-000200
    124 125 126124 125 126
    Figure PCTKR2023003724-appb-img-000201
    Figure PCTKR2023003724-appb-img-000201
    127 128 129127 128 129
    Figure PCTKR2023003724-appb-img-000202
    Figure PCTKR2023003724-appb-img-000202
    130 131 132130 131 132
    Figure PCTKR2023003724-appb-img-000203
    Figure PCTKR2023003724-appb-img-000203
    133 134 135133 134 135
    Figure PCTKR2023003724-appb-img-000204
    Figure PCTKR2023003724-appb-img-000204
    136 137 138136 137 138
    Figure PCTKR2023003724-appb-img-000205
    Figure PCTKR2023003724-appb-img-000205
    139 140 141139 140 141
    Figure PCTKR2023003724-appb-img-000206
    Figure PCTKR2023003724-appb-img-000206
    142 143 144142 143 144
    Figure PCTKR2023003724-appb-img-000207
    Figure PCTKR2023003724-appb-img-000207
    145 146 147145 146 147
    Figure PCTKR2023003724-appb-img-000208
    Figure PCTKR2023003724-appb-img-000208
    148 149 150148 149 150
    Figure PCTKR2023003724-appb-img-000209
    Figure PCTKR2023003724-appb-img-000209
    151 152 153151 152 153
    Figure PCTKR2023003724-appb-img-000210
    Figure PCTKR2023003724-appb-img-000210
    154 155 156154 155 156
    Figure PCTKR2023003724-appb-img-000211
    Figure PCTKR2023003724-appb-img-000211
    157 158 159157 158 159
    Figure PCTKR2023003724-appb-img-000212
    Figure PCTKR2023003724-appb-img-000212
    160 161 162160 161 162
    Figure PCTKR2023003724-appb-img-000213
    Figure PCTKR2023003724-appb-img-000213
    163 164 165163 164 165
    Figure PCTKR2023003724-appb-img-000214
    Figure PCTKR2023003724-appb-img-000214
    166 167 168166 167 168
    Figure PCTKR2023003724-appb-img-000215
    Figure PCTKR2023003724-appb-img-000215
    169 170 171169 170 171
    Figure PCTKR2023003724-appb-img-000216
    Figure PCTKR2023003724-appb-img-000216
    172 173 174172 173 174
    Figure PCTKR2023003724-appb-img-000217
    Figure PCTKR2023003724-appb-img-000217
    175 176 177175 176 177
    Figure PCTKR2023003724-appb-img-000218
    Figure PCTKR2023003724-appb-img-000218
    178 179 180178 179 180
    Figure PCTKR2023003724-appb-img-000219
    Figure PCTKR2023003724-appb-img-000219
    181 182 183181 182 183
    Figure PCTKR2023003724-appb-img-000220
    Figure PCTKR2023003724-appb-img-000220
    184 185 186184 185 186
    Figure PCTKR2023003724-appb-img-000221
    Figure PCTKR2023003724-appb-img-000221
    187 188 189187 188 189
    Figure PCTKR2023003724-appb-img-000222
    Figure PCTKR2023003724-appb-img-000222
    190 191 192190 191 192
    Figure PCTKR2023003724-appb-img-000223
    Figure PCTKR2023003724-appb-img-000223
    193 194 195193 194 195
    Figure PCTKR2023003724-appb-img-000224
    Figure PCTKR2023003724-appb-img-000224
    196 197 198196 197 198
    Figure PCTKR2023003724-appb-img-000225
    Figure PCTKR2023003724-appb-img-000225
    199 200 201199 200 201
    Figure PCTKR2023003724-appb-img-000226
    Figure PCTKR2023003724-appb-img-000226
    202 203 204202 203 204
    Figure PCTKR2023003724-appb-img-000227
    Figure PCTKR2023003724-appb-img-000227
    205 206 207205 206 207
    Figure PCTKR2023003724-appb-img-000228
    Figure PCTKR2023003724-appb-img-000228
    208 209 210208 209 210
    Figure PCTKR2023003724-appb-img-000229
    Figure PCTKR2023003724-appb-img-000229
    211 212 213211 212 213
    Figure PCTKR2023003724-appb-img-000230
    Figure PCTKR2023003724-appb-img-000230
    214 215 216214 215 216
    Figure PCTKR2023003724-appb-img-000231
    Figure PCTKR2023003724-appb-img-000231
    217 218 219217 218 219
    Figure PCTKR2023003724-appb-img-000232
    Figure PCTKR2023003724-appb-img-000232
    220 221 222220 221 222
    Figure PCTKR2023003724-appb-img-000233
    Figure PCTKR2023003724-appb-img-000233
    223 224 225223 224 225
    Figure PCTKR2023003724-appb-img-000234
    Figure PCTKR2023003724-appb-img-000234
    226 227 228226 227 228
    Figure PCTKR2023003724-appb-img-000235
    Figure PCTKR2023003724-appb-img-000235
    229 230 231229 230 231
    Figure PCTKR2023003724-appb-img-000236
    Figure PCTKR2023003724-appb-img-000236
    232 233 234232 233 234
    Figure PCTKR2023003724-appb-img-000237
    Figure PCTKR2023003724-appb-img-000237
    235 236 237235 236 237
    Figure PCTKR2023003724-appb-img-000238
    Figure PCTKR2023003724-appb-img-000238
    238 239 240238 239 240
  9. 제1전극;first electrode;
    상기 제1전극에 대향된 제2전극; 및 a second electrode opposite the first electrode; and
    상기 제1전극과 상기 제2전극사이에 개재되는 유기층;을 포함하고, It includes an organic layer interposed between the first electrode and the second electrode,
    상기 유기층은 발광층; 및, The organic layer is a light emitting layer; and,
    정공 주입층, 정공 수송층, 정공 주입 기능 및 정공 수송 기능을 동시에 갖는 기능층, 전자저지층, 정공저지층, 전자 수송층 및 전자 주입층 중 적어도 하나의 층;을 포함하며, At least one layer of a hole injection layer, a hole transport layer, a functional layer having both a hole injection function and a hole transport function, an electron blocking layer, a hole blocking layer, an electron transport layer, and an electron injection layer;
    상기 발광층은 호스트와 도판트를 포함하며, 상기 호스트는 제 1 항 내지 제 8 항에 따른, [화학식 A] 또는 [화학식 B]로 표시되는 방향족 헤테로고리 화합물을 1 종 이상 포함하는 유기발광소자.The light-emitting layer includes a host and a dopant, and the host includes one or more aromatic heterocyclic compounds represented by [Formula A] or [Formula B] according to claims 1 to 8. An organic light-emitting device.
  10. 제 9 항에 있어서,According to clause 9,
    상기 발광층내 호스트는 상기 [화학식 A] 또는 [화학식 B]로 표시되는 방향족 헤테로고리 화합물 1종 외에의 추가적인 호스트 화합물이 혼합 또는 적층되어 사용되는 것을 특징으로 하는 유기발광소자.An organic light-emitting device, wherein the host in the light-emitting layer is used by mixing or stacking additional host compounds in addition to the aromatic heterocyclic compound represented by [Formula A] or [Formula B].
  11. 제 10 항에 있어서,According to claim 10,
    상기 발광층내 상기 [화학식 A] 또는 [화학식 B]로 표시되는 방향족 헤테로고리 화합물 1종외의 추가적으로 사용되는 호스트는, 전자받개 모이어티를 가지는 화합물이 사용되는 것을 특징으로 하는 유기발광소자.An organic light-emitting device, wherein the host used in addition to the aromatic heterocyclic compound represented by [Formula A] or [Formula B] in the light-emitting layer is a compound having an electron accepting moiety.
  12. 제 11 항에 있어서,According to claim 11,
    상기 전자받개 모이어티를 가지는 화합물은 분자내 N(질소)을 1 내지 3개 포함하는 헤테로아릴기; 또는, 분자내 1 내지 3개의 시아노기(-CN)를 포함하는 아릴기;를 포함하는 화합물인 것을 특징으로 하는 유기발광소자.The compound having the electron accepting moiety is a heteroaryl group containing 1 to 3 N (nitrogen) atoms in the molecule; Or, an organic light-emitting device characterized in that it is a compound containing an aryl group containing 1 to 3 cyano groups (-CN) in the molecule.
  13. 제 9 항에 있어서,According to clause 9,
    상기 유기발광 소자는 평판 디스플레이 장치; 플렉시블 디스플레이 장치; 단색 또는 백색의 평판 조명용 장치; 단색 또는 백색의 플렉시블 조명용 장치; 차량용 디스플레이 장치; 및 가상 또는 증강 현실용 디스플레이 장치;에서 선택되는 어느 하나의 장치에 사용되는 유기발광소자.The organic light emitting device may include a flat panel display device; flexible display device; Devices for monochromatic or white flat lighting; Devices for flexible lighting, either monochromatic or white; Vehicle display devices; and a display device for virtual or augmented reality. An organic light emitting device used in any one device selected from the group consisting of:
PCT/KR2023/003724 2022-03-23 2023-03-21 Novel heterocyclic compound and organic light-emitting diode including same WO2023182775A1 (en)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
KR20220036039 2022-03-23
KR10-2022-0036039 2022-03-23
KR20220076756 2022-06-23
KR10-2022-0076756 2022-06-23

Publications (1)

Publication Number Publication Date
WO2023182775A1 true WO2023182775A1 (en) 2023-09-28

Family

ID=88101796

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/KR2023/003724 WO2023182775A1 (en) 2022-03-23 2023-03-21 Novel heterocyclic compound and organic light-emitting diode including same

Country Status (2)

Country Link
KR (1) KR20230138921A (en)
WO (1) WO2023182775A1 (en)

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2014003336A1 (en) * 2012-06-27 2014-01-03 덕산하이메탈(주) Compound, electro-organic device using same, and electronic device thereof
US20140047976A1 (en) * 2011-04-29 2014-02-20 Yin Fong Yeong Cardo-Polybenzoxazole Polymer/Copolymer Membranes For Improved Permeability And Method For Fabricating The Same
US20160141515A1 (en) * 2013-06-11 2016-05-19 Idemitsu Kosan Co., Ltd. Material for organic electroluminescent elements, organic electroluminescent element using same, and electronic device
US20170346018A1 (en) * 2015-03-13 2017-11-30 Fujifilm Corporation Composition for forming organic semiconductor film, organic thin film transistor, electronic paper, and display device
KR20210006283A (en) * 2019-07-08 2021-01-18 롬엔드하스전자재료코리아유한회사 A plurality of host materials and organic electroluminescent device comprising the same

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20160143678A (en) 2014-04-22 2016-12-14 유니버셜 디스플레이 코포레이션 Material for phosphorescent light-emitting element
CN114497425A (en) 2014-05-23 2022-05-13 罗门哈斯电子材料韩国有限公司 Multi-component host material and organic electroluminescent device comprising same

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20140047976A1 (en) * 2011-04-29 2014-02-20 Yin Fong Yeong Cardo-Polybenzoxazole Polymer/Copolymer Membranes For Improved Permeability And Method For Fabricating The Same
WO2014003336A1 (en) * 2012-06-27 2014-01-03 덕산하이메탈(주) Compound, electro-organic device using same, and electronic device thereof
US20160141515A1 (en) * 2013-06-11 2016-05-19 Idemitsu Kosan Co., Ltd. Material for organic electroluminescent elements, organic electroluminescent element using same, and electronic device
US20170346018A1 (en) * 2015-03-13 2017-11-30 Fujifilm Corporation Composition for forming organic semiconductor film, organic thin film transistor, electronic paper, and display device
KR20210006283A (en) * 2019-07-08 2021-01-18 롬엔드하스전자재료코리아유한회사 A plurality of host materials and organic electroluminescent device comprising the same

Also Published As

Publication number Publication date
KR20230138921A (en) 2023-10-05

Similar Documents

Publication Publication Date Title
WO2020105990A1 (en) Novel boron compound and organic light-emitting device comprising same
WO2018066830A1 (en) Organic light-emitting device having long life, low voltage and high efficiency
WO2018066831A1 (en) Organic light-emitting device having long life, low voltage and high efficiency
WO2016117848A1 (en) Compound for organic light-emitting device and organic light-emitting device comprising same
WO2020106032A1 (en) Novel boron compound and organic light-emitting device comprising same
WO2013081315A1 (en) Compound for organic electronic device, organic electronic device comprising same and electronic device comprising the organic electronic device
WO2021010770A1 (en) Novel boron compound and organic light-emitting device comprising same
WO2019240464A1 (en) Organic light-emitting device
WO2017082574A1 (en) Novel heterocyclic compound and organic light-emitting device comprising same
WO2016167505A1 (en) Novel heterocyclic compound and organic light emitting element including same
WO2022211594A1 (en) Composition for organic optoelectronic device, organic optoelectronic device, and display device
WO2021162347A1 (en) Novel boron compound, and organic light-emitting element comprising same
WO2020067593A1 (en) Heterocyclic compound and organic light-emitting device comprising same
WO2016089165A2 (en) Novel compound and organic light emitting element comprising same
WO2021210894A1 (en) Novel boron compound and organic light-emitting element comprising same
WO2021187939A1 (en) Novel boron compound and organic light-emitting element comprising same
WO2016060463A2 (en) Novel compound and organic light-emitting element comprising same
WO2023096399A1 (en) High efficiency and long lifetime organic light-emitting diode
WO2020159334A1 (en) Compound and organic light-emitting element comprising same
WO2020159333A1 (en) Compound and organic light emitting device comprising same
WO2023128521A1 (en) Organoelectroluminescent device
WO2022025511A1 (en) Novel heterocyclic compound and organic light-emitting device comprising same
WO2020263000A1 (en) Novel compound and organic light emitting device using same
WO2023182775A1 (en) Novel heterocyclic compound and organic light-emitting diode including same
WO2020111728A1 (en) Organic light emitting device

Legal Events

Date Code Title Description
121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 23775271

Country of ref document: EP

Kind code of ref document: A1