WO2018169352A1 - Dispositif électroluminescent organique - Google Patents

Dispositif électroluminescent organique Download PDF

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Publication number
WO2018169352A1
WO2018169352A1 PCT/KR2018/003101 KR2018003101W WO2018169352A1 WO 2018169352 A1 WO2018169352 A1 WO 2018169352A1 KR 2018003101 W KR2018003101 W KR 2018003101W WO 2018169352 A1 WO2018169352 A1 WO 2018169352A1
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Prior art keywords
unsubstituted
substituted
membered
organic electroluminescent
hole transport
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PCT/KR2018/003101
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English (en)
Inventor
Tae-Jin Lee
Bitnari Kim
Hee-Ryong Kang
Dong-Hyung Lee
Hong-Se OH
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Rohm And Haas Electronic Materials Korea Ltd.
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Priority claimed from KR1020180026943A external-priority patent/KR102550843B1/ko
Application filed by Rohm And Haas Electronic Materials Korea Ltd. filed Critical Rohm And Haas Electronic Materials Korea Ltd.
Priority to JP2019546890A priority Critical patent/JP7057369B2/ja
Priority to CN201880012803.5A priority patent/CN110313079B/zh
Priority to US16/492,632 priority patent/US20200058882A1/en
Publication of WO2018169352A1 publication Critical patent/WO2018169352A1/fr

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    • 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
    • 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
    • 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
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • 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
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/14—Carrier transporting layers
    • H10K50/15—Hole transporting layers
    • H10K50/156—Hole transporting layers comprising a multilayered structure
    • 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
    • H10K85/30—Coordination compounds
    • H10K85/341—Transition metal complexes, e.g. Ru(II)polypyridine complexes
    • H10K85/342—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising iridium
    • 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
    • H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom

Definitions

  • the present disclosure relates to an organic electroluminescent device comprising a light-emitting layer and a hole transport zone.
  • the first low molecular green light-emitting organic electroluminescent device was developed by Tang, etc., of Eastman Kodak in 1987 by using TPD/ALq3 bi-layer consisting of a light-emitting layer and a charge transport layer. Thereafter, the development of organic EL devices was rapidly effected and the devices were currently commercialized. Current organic EL devices mostly use phosphorescent materials with excellent luminous efficiency for panel manufacture. For long-term use and high resolution of the display, a low driving voltage and high luminous efficiency are required.
  • Korean Patent Appln. Laying-Open No. 2015-0071685 A discloses an organic electroluminescent device using a compound comprising a carbazole and a nitrogen-containing 10-membered heteroaryl as a host.
  • the reference does not disclose an organic electroluminescent device using a compound comprising a benzoindolocarbazole and a nitrogen-containing 10-membered heteroaryl as a host and comprising a compound having a HOMO (Highest Occupied Molecular Orbital) energy level of -5.0 eV to -4.6 eV between the first electrode and the light-emitting layer.
  • HOMO Highest Occupied Molecular Orbital
  • the objective of the present disclosure is to provide an organic electroluminescent device having excellent luminous efficiency while maintaining excellent lifespan or driving voltage characteristic of the device by comprising the combination of a light-emitting layer and a hole transport zone having a certain HOMO energy value.
  • an organic electroluminescent device comprising a first electrode; a second electrode facing the first electrode; a light-emitting layer between the first electrode and the second electrode; and a hole transport zone between the first electrode and the light-emitting layer, wherein the light-emitting layer comprises a compound represented by the following formula 1:
  • L 1 represents a single bond, a substituted or unsubstituted (C6-C30)arylene, or a substituted or unsubstituted (5- to 30-membered)heteroarylene;
  • X 1 to X 6 each independently represent N or CR 3 , with a proviso that at least one of X 1 to X 6 represent N;
  • Ar 1 represents a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (5- to 30-membered)heteroaryl;
  • R 1 to R 3 each independently represent hydrogen, deuterium, a halogen, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (5- to 30-membered)heteroaryl, a substituted or unsubstituted (C3-C30)cycloalkyl, a substituted or unsubstituted (3- to 7-membered)heterocycloalkyl, a substituted or unsubstituted (C6-C30)aryl(C1-C30)alkyl, -NR 11 R 12 , -SiR 13 R 14 R 15 , -SR 16 , -OR 17 , a cyano, a nitro, or a hydroxyl, with a proviso that in at least one group of the adjacent two R 1 's and the adjacent two R 2 's groups,
  • R 11 to R 17 each independently represent hydrogen, deuterium, a halogen, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (5- to 30-membered)heteroaryl, a substituted or unsubstituted (3- to 7-membered)heterocycloalkyl, or a substituted or unsubstituted (C3-C30)cycloalkyl; or may be linked to an adjacent substituent(s) to form a substituted or unsubstituted, mono- or polycyclic, (3- to 30-membered) alicyclic or aromatic ring, or the combination thereof, whose carbon atom(s) may be replaced with at least one heteroatom selected from nitrogen, oxygen, and sulfur;
  • a and b each independently represent an integer of 1 to 4, where if a and b each independently are an integer of 2 or more, each of R 1 and R 2 may be the same or different;
  • the heteroaryl(ene) contains at least one heteroatom selected from B, N, O, S, Si, and P;
  • the heterocycloalkyl contains at least one heteroatom selected from O, S, and N, and
  • the hole transport zone comprises an arylamine derivative comprising one carbazole or fused carbazole
  • the HOMO energy value of the arylamine derivative comprising one carbazole or fused carbazole satisfies the following equation 11:
  • an organic electroluminescent device of excellent luminous efficiency while maintaining excellent lifespan or driving voltage characteristic of the device can be provided, and it is possible to produce a display device or a lighting device using the same.
  • organic electroluminescent compound in the present disclosure means a compound that may be used in an organic electroluminescent device, and may be comprised in any layer constituting an organic electroluminescent device, as necessary.
  • organic electroluminescent material in the present disclosure means a material that may be used in an organic electroluminescent device, and may comprise at least one compound.
  • the organic electroluminescent material may be comprised in any layer constituting an organic electroluminescent device, as necessary.
  • the organic electroluminescent material may be a hole injection material, a hole transport material, a hole auxiliary material, a light-emitting auxiliary material, an electron blocking material, a light-emitting material, an electron buffer material, a hole blocking material, an electron transport material, or an electron injection material.
  • the organic electroluminescent device of the present disclosure comprises a first electrode; a second electrode facing the first electrode; and a light-emitting layer between the first electrode and the second electrode, may comprise a hole transport zone between the first electrode and the light-emitting layer, and may comprise an electron transport zone between the light-emitting layer and the second electrode.
  • One of the first and second electrodes may be an anode and the other may be a cathode.
  • the hole transport zone is meant to be a zone wherein holes are transported between the first electrode and the light-emitting layer, and may comprise, for example, one or more of a hole injection layer, a hole transport layer, a hole auxiliary layer, a light-emitting auxiliary layer, and an electron blocking layer.
  • the hole injection layer, the hole transport layer, the hole auxiliary layer, the light-emitting auxiliary layer, and the electron blocking layer, respectively may be a single layer, or a multi-layer in which two or more layers are stacked.
  • the hole transport zone may comprise a first hole transport layer and a second hole transport layer.
  • the second hole transport layer may be one or more layers of the multiple hole transport layers, and may comprise one or more of a hole auxiliary layer, a light-emitting auxiliary layer, and an electron blocking layer.
  • the hole transport zone may comprise a first hole transport layer and a second hole transport layer, in which the first hole transport layer may be placed between the first electrode and the light-emitting layer and the second hole transport layer may be placed between the first hole transport layer and the light-emitting layer, and the second hole transport layer may be a layer which plays a role as a hole transport layer, a light-emitting auxiliary layer, a hole auxiliary layer, and/or an electron blocking layer.
  • the hole transport layer is placed between the anode (or hole injection layer) and the light-emitting layer, enables the holes transported from the anode to be transported smoothly to the light-emitting layer, and can also function so as to block the electrons transported from the cathode to stay at the light-emitting layer.
  • the light-emitting auxiliary layer may be placed between the anode and the light-emitting layer, or between the cathode and the light-emitting layer. When the light-emitting auxiliary layer is placed between the anode and the light-emitting layer, it can be used for promoting the hole injection and/or hole transport, or for preventing the overflow of electrons.
  • the light-emitting auxiliary layer When the light-emitting auxiliary layer is placed between the cathode and the light-emitting layer, it can be used for promoting the electron injection and/or electron transport, or for preventing the overflow of holes.
  • the hole auxiliary layer may be placed between the hole transport layer (or hole injection layer) and the light-emitting layer, and may be effective to promote or block the hole transport rate (or hole injection rate), thereby enabling the charge balance to be controlled.
  • the electron blocking layer may be placed between the hole transport layer (or hole injection layer) and the light-emitting layer, and can confine the excitons within the light-emitting layer by blocking the overflow of electrons from the light-emitting layer to prevent a light-emitting leakage.
  • the hole transport layer which is further included, may be used as a light-emitting auxiliary layer, a hole auxiliary layer, an electron blocking layer, etc.
  • the light-emitting auxiliary layer, the hole auxiliary layer, and/or the electron blocking layer may have an effect of improving the luminous efficiency and/or the lifespan of the organic electroluminescent device.
  • the hole transport zone comprises an arylamine derivative comprising one carbazole or fused carbazole, and the HOMO energy value of the arylamine derivative comprising one carbazole or fused carbazole satisfies equation 11.
  • the compound comprised in the hole transport zone has a HOMO energy level of -4.6 eV to -5.0 eV. If the HOMO energy level is lower than -5.0 eV, the luminous efficiency of the device increases but there is no significant advantage in terms of power efficiency since the driving voltage also increases as the luminous efficiency increases. If the HOMO energy level is higher than -4.6 eV, the driving voltage of the device decreases but the luminous efficiency also decreases.
  • the organic electroluminescent device wherein the compound comprised in the hole transport zone has a HOMO energy value satisfying equation 11 and the light-emitting layer comprises a compound represented by formula 1, has high luminous efficiency and an appropriately low driving voltage.
  • the electron transport zone may comprise one or more of an electron buffer layer, a hole blocking layer, an electron transport layer, and an electron injection layer, and preferably may comprise one or more of an electron transport layer and an electron injection layer.
  • the electron buffer layer is a layer capable of improving the problem that the current characteristics in the device changes upon exposure to a high temperature in a panel fabrication process to cause deformation of light emission luminance, which can control the flow of charge.
  • the light-emitting layer emits light, which may be a single layer, or a multi-layer in which two or more layers are stacked.
  • the doping concentration of the dopant compound to the host compound in the light-emitting layer is preferably less than 20 wt%.
  • the light-emitting layer comprises a compound represented by formula 1.
  • L 1 represents a single bond, a substituted or unsubstituted (C6-C30)arylene, or a substituted or unsubstituted (5- to 30-membered)heteroarylene; preferably, a single bond, a substituted or unsubstituted (C6-C25)arylene, or a substituted or unsubstituted (5- to 25-membered)heteroarylene; more preferably, a single bond, a substituted or unsubstituted (C6-C18)arylene, or a substituted or unsubstituted (5- to 18-membered)heteroarylene; and for example, a single bond, an unsubstituted phenylene, an unsubstituted naphthylene, or an unsubstituted pyridinylene.
  • X 1 to X 6 each independently represent N or CR 3 , with a proviso that at least one of X 1 to X 6 represent N. At least one of X 1 and X 6 may represent N, and X 2 to X 5 may represent CR 3 .
  • the structure of may represent a substituted or unsubstituted quinoxalinyl, a substituted or unsubstituted quinazolinyl, a substituted or unsubstituted naphthyridinyl, a substituted or unsubstituted pyridopyrimidinyl, or a substituted or unsubstituted pyridopyrazinyl; preferably, a substituted or unsubstituted quinoxalinyl, or a substituted or unsubstituted quinazolinyl, and wherein, * represents a bonding site with L 1 .
  • Ar 1 represents a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (5- to 30-membered)heteroaryl; preferably, a substituted or unsubstituted (C6-C25)aryl, or a substituted or unsubstituted (5- to 25-membered)heteroaryl; more preferably, a substituted or unsubstituted (C6-C18)aryl, or a substituted or unsubstituted (5- to 18-membered)heteroaryl; and for example, an unsubstituted phenyl, an unsubstituted naphthyl, an unsubstituted biphenyl, a fluorenyl substituted with dimethyl, an unsubstituted phenanthrenyl, or an unsubstituted pyridinyl.
  • R 1 to R 3 each independently represent hydrogen, deuterium, a halogen, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (5- to 30-membered)heteroaryl, a substituted or unsubstituted (C3-C30)cycloalkyl, a substituted or unsubstituted (3- to 7-membered)heterocycloalkyl, a substituted or unsubstituted (C6-C30)aryl(C1-C30)alkyl, -NR 11 R 12 , -SiR 13 R 14 R 15 , -SR 16 , -OR 17 , a cyano, a nitro, or a hydroxyl; preferably, hydrogen, or a substituted or unsubstituted (C6-C25)aryl; and more
  • R 1 and R 2 each independently may represent hydrogen, or an unsubstituted phenyl
  • R 3 may represent hydrogen, a phenyl unsubstituted or substituted with at least one methyl, an unsubstituted naphthyl, an unsubstituted biphenyl, an unsubstituted naphthylphenyl, a fluorenyl substituted with dimethyl, or an unsubstituted phenanthrenyl.
  • the adjacent two R 1 's or the adjacent two R 2 's each independently are linked to each other to form at least one substituted or unsubstituted benzene ring.
  • the adjacent two R 1 's or the adjacent two R 2 's each independently may be linked to each other to form one substituted or unsubstituted benzene ring, and preferably, an unsubstituted benzene ring.
  • R 3 may represent a substituted or unsubstituted (C6-C18)aryl.
  • R 3 may represent hydrogen.
  • R 11 to R 17 each independently represent hydrogen, deuterium, a halogen, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (5- to 30-membered)heteroaryl, a substituted or unsubstituted (3- to 7-membered)heterocycloalkyl, or a substituted or unsubstituted (C3-C30)cycloalkyl; or may be linked to an adjacent substituent(s) to form a substituted or unsubstituted, mono- or polycyclic, (3- to 30-membered) alicyclic or aromatic ring, or the combination thereof, whose carbon atom(s) may be replaced with at least one heteroatom selected from nitrogen, oxygen, and sulfur.
  • a and b each independently represent an integer of 1 to 4, and preferably an integer of 1 to 3. If a and b each independently are an integer of 2 or more, each of R 1 and R 2 may be the same or different.
  • Formula 1 may be represented by any one of the following formulas 2 to 7.
  • L 1 , Ar 1 , R 1 , R 2 , X 1 to X 6 , a, and b are as defined in formula 1, and R 5 and R 6 are each independently identical to the definition of R 1 .
  • c and d each independently represent an integer of 1 to 6; preferably 1 or 2; and more preferably 1. If c and d each independently are an integer of 2 or more, each of R 5 and R 6 may be the same or different.
  • the arylamine derivative comprising one carbazole or fused carbazole comprised in the hole transport zone of the present disclosure, for example, one or more of a light-emitting auxiliary layer and a hole auxiliary layer, and the second hole transport layer may comprise at least one compound represented by the following formula 11 or 12:
  • Ar 2 to Ar 6 each independently represent a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (5- to 30-membered)heteroaryl, preferably, a substituted or unsubstituted (C6-C25)aryl, or a substituted or unsubstituted (5- to 25-membered)heteroaryl, and more preferably, a substituted or unsubstituted (C6-C18)aryl, or a substituted or unsubstituted (5- to 18-membered)heteroaryl.
  • Ar 2 to Ar 5 each independently may represent a phenyl unsubstituted or substituted with a dibenzothiophenyl(s), an unsubstituted naphthyl, a biphenyl unsubstituted or substituted with a dibenzothiophenyl(s), an unsubstituted naphthylphenyl, an unsubstituted terphenyl, a fluorenyl substituted with dimethyl, a benzofluorenyl substituted with dimethyl, or an unsubstituted dibenzothiophenyl
  • Ar 6 may represent a phenyl unsubstituted or substituted with a dibenzothiophenyl(s), or an unsubstituted biphenyl.
  • L 2 and L 3 each independently represent a single bond, or a substituted or unsubstituted (C6-C30)arylene, preferably, a single bond, or a substituted or unsubstituted (C6-C25)arylene, and more preferably, a single bond, or a substituted or unsubstituted (C6-C18)arylene.
  • L 2 and L 3 each independently may represent a single bond, a phenylene unsubstituted or substituted with a dibenzothiophenyl(s) or a diphenylamino(s), an unsubstituted biphenylene, an unsubstituted terphenylene, or a fluorenylene substituted with dimethyl.
  • R 7 to R 10 each independently represent hydrogen, deuterium, a halogen, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (5- to 30-membered)heteroaryl, a substituted or unsubstituted (C3-C30)cycloalkyl, a substituted or unsubstituted (3- to 7-membered)heterocycloalkyl, a substituted or unsubstituted (C6-C30)aryl(C1-C30)alkyl, -NR 11 R 12 , -SiR 13 R 14 R 15 , -SR 16 , -OR 17 , a cyano, a nitro, or a hydroxyl; or may be linked to an adjacent substituent(s) to form a substituted or unsubstituted, mono
  • R 7 to R 10 each independently may represent a fluorenyl substituted with dimethyl, an unsubstituted dibenzofuranyl, an unsubstituted dibenzothiophenyl, an unsubstituted benzofuranocarbazolyl, or an unsubstituted diphenylamino; or may be linked to an adjacent substituent(s) to form a benzene ring, a benzofuran ring unsubstituted or substituted with a phenyl(s), a benzothiophene ring unsubstituted or substituted with a phenyl(s), an indene ring substituted with dimethyl, or an indole ring substituted with a phenyl(s).
  • R 11 to R 17 each independently represent hydrogen, deuterium, a halogen, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (5- to 30-membered)heteroaryl, a substituted or unsubstituted (3- to 7-membered)heterocycloalkyl, or a substituted or unsubstituted (C3-C30)cycloalkyl; or may be linked to an adjacent substituent(s) to form a substituted or unsubstituted, mono- or polycyclic, (3- to 30-membered) alicyclic or aromatic ring, or the combination thereof, whose carbon atom(s) may be replaced with at least one heteroatom selected from nitrogen, oxygen, and sulfur.
  • R 11 and R 12 each independently may represent an unsubstituted
  • e to g each independently represent an integer of 1 to 4, and h represents an integer of 1 to 3. If e to h each independently are an integer of 2 or more, each of R 7 to R 10 may be the same or different.
  • (C1-C30)alkyl is meant to be a linear or branched alkyl having 1 to 30 carbon atoms constituting the chain, in which the number of carbon atoms is preferably 1 to 20, more preferably 1 to 10, and includes methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, etc.
  • (C2-C30)alkenyl is meant to be a linear or branched alkenyl having 2 to 30 carbon atoms constituting the chain, in which the number of carbon atoms is preferably 2 to 20, more preferably 2 to 10, and includes vinyl, 1-propenyl, 2-propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 2-methylbut-2-enyl, etc.
  • (C2-C30)alkynyl is a linear or branched alkynyl having 2 to 30 carbon atoms constituting the chain, in which the number of carbon atoms is preferably 2 to 20, more preferably 2 to 10, and includes ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methylpent-2-ynyl, etc.
  • (C3-C30)cycloalkyl is a mono- or polycyclic hydrocarbon having 3 to 30 ring backbone carbon atoms, in which the number of carbon atoms is preferably 3 to 20, more preferably 3 to 7, and includes cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, etc.
  • (3- to 7-membered)heterocycloalkyl is a cycloalkyl having at least one heteroatom selected from the group consisting of B, N, O, S, Si, and P, preferably O, S, and N, and 3 to 7, preferably 5 to 7 ring backbone atoms, and includes tetrahydrofuran, pyrrolidine, thiolan, tetrahydropyran, etc.
  • (C6-C30)aryl(ene) is a monocyclic or fused ring-type radical derived from an aromatic hydrocarbon having 6 to 30 ring backbone carbon atoms, in which the number of ring backbone carbon atoms is preferably 6 to 25, more preferably 6 to 18, may be partially saturated, may comprise a spiro structure, and includes phenyl, biphenyl, terphenyl, naphthyl, binaphthyl, phenylnaphthyl, naphthylphenyl, phenylterphenyl, fluorenyl, phenylfluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, phenylphenanthrenyl, anthracenyl, indenyl, triphenylenyl, pyrenyl, tetracenyl, perylenyl, chrysenyl, naphthaceny
  • (5- to 30-membered)heteroaryl(ene) is an aryl group having at least one, preferably 1 to 4 heteroatoms selected from the group consisting of B, N, O, S, Si, and P, and 5 to 30 ring backbone atoms; is a monocyclic ring, or a fused ring condensed with at least one benzene ring; may be partially saturated; may be one formed by linking at least one heteroaryl or aryl group to a heteroaryl group via a single bond(s); may comprise a spiro structure; and includes a monocyclic ring-type heteroaryl including furyl, thiophenyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetrazinyl, triazolyl, te
  • substituted in the expression “substituted or unsubstituted” means that a hydrogen atom in a certain functional group is replaced with another atom or functional group, i.e., a substituent.
  • the compound represented by formula 1 includes the following compounds, but is not limited thereto:
  • the compound represented by formula 11 or 12 includes the following compounds, but is not limited thereto:
  • the compound of formula 1 of the present disclosure can be prepared by a synthetic method known to a person skilled in the art, for example, according to the following reaction schemes, but is not limited thereto.
  • L 1 , Ar 1 , R 1 , R 2 , R 5 , R 6 , X 1 to X 6 , a, b, c, and d are as defined in formulas 1 to 7, and X represents halogen.
  • the compounds of formulas 11 and 12 of the present disclosure can be prepared by a synthetic method known to a person skilled in the art, for example, using or modifying the synthesis method disclosed in KR 2013-0106255 A, KR 2010-0106014 A, KR 2014-0043224 A, etc.
  • the dopant comprised in the organic electroluminescent device according to the present disclosure may be at least one phosphorescent or fluorescent dopant, and preferably a phosphorescent dopant.
  • the phosphorescent dopant materials applied to the organic electroluminescent device according to the present disclosure are not particularly limited, but may be selected from metallated complex compounds of iridium (Ir), osmium (Os), copper (Cu), and platinum (Pt), more preferably selected from ortho-metallated complex compounds of iridium (Ir), osmium (Os), copper (Cu), and platinum (Pt), and even more preferably an ortho-metallated iridium complex compound.
  • the dopant comprised in the organic electroluminescent device of the present disclosure may be a compound represented by formula 101 below, but is not limited thereto.
  • L is selected from the following structures 1 and 2:
  • R 100 to R 103 each independently represent hydrogen, deuterium, a halogen, a (C1-C30)alkyl unsubstituted or substituted with a halogen(s), a substituted or unsubstituted (C3-C30)cycloalkyl, a substituted or unsubstituted (C6-C30)aryl, a cyano, a substituted or unsubstituted (3- to 30-membered)heteroaryl, or a substituted or unsubstituted (C1-C30)alkoxy; or adjacent substituents of R 100 to R 103 may be linked to each other to form a substituted or unsubstituted fused ring together with the pyridine, e.g., a substituted or unsubstituted quinoline, a substituted or unsubstituted isoquinoline, a substituted or unsubstituted benzofuropyridine, a substituted or unsub
  • R 104 to R 107 each independently represent hydrogen, deuterium, a halogen, a (C1-C30)alkyl unsubstituted or substituted with a halogen(s), a substituted or unsubstituted (C3-C30)cycloalkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (3- to 30-membered)heteroaryl, a cyano, or a substituted or unsubstituted (C1-C30)alkoxy; or adjacent substituents of R 104 to R 107 may be linked to each other to form a substituted or unsubstituted fused ring together with the benzene, e.g., a substituted or unsubstituted naphthyl, a substituted or unsubstituted fluorene, a substituted or unsubstituted dibenzothiophene,
  • R 201 to R 211 each independently represent hydrogen, deuterium, a halogen, a (C1-C30)alkyl unsubstituted or substituted with a halogen(s), a substituted or unsubstituted (C3-C30)cycloalkyl, or a substituted or unsubstituted (C6-C30)aryl; or adjacent substituents of R 201 to R 211 may be linked to each other to form a substituted or unsubstituted fused ring; and
  • n an integer of 1 to 3.
  • dopant compound is as follows, but are not limited thereto.
  • the organic electroluminescent device comprises a hole transport zone between the first electrode and the light-emitting layer, wherein the hole transport zone comprises an arylamine derivative comprising one carbazole or fused carbazole, and the HOMO energy value of the arylamine derivative comprising one carbazole or fused carbazole satisfies equation 11 below.
  • the first hole transport layer may be comprised between the first electrode and the light-emitting layer
  • the second hole transport layer may be comprised between the first hole transport layer and the light-emitting layer
  • the second hole transport layer may comprise an arylamine derivative comprising one carbazole or fused carbazole
  • the HOMO energy value of the arylamine derivative comprising one carbazole or fused carbazole may satisfy equation 11 below.
  • the second hole transport layer may be a single layer or a multi-layer
  • the second hole transport layer may be a layer which plays a role as a hole transport layer, a light-emitting auxiliary layer, a hole auxiliary layer, and/or an electron blocking layer.
  • the HOMO energy value of the arylamine derivative comprising one carbazole or fused carbazole may satisfy the following equation 12.
  • the HOMO energy value of the arylamine derivative comprising one carbazole or fused carbazole may satisfy the following equation 13.
  • the hole injection and/or transport from the first electrode to the second hole transport layer is not so smooth that the problem of unsatisfactory luminous efficiency of the device may occur, and if the HOMO energy value is lower than the lower limit of the above, the luminous efficiency of the device increases but there is no significant advantage in terms of power efficiency since the driving voltage also increases as the luminous efficiency increases.
  • a display device for example, for smartphones, tablets, notebooks, PCs, TVs, or vehicles, or a lighting device, for example, an indoor or outdoor lighting device can be produced.
  • the organic electroluminescent device of the present disclosure is intended to explain one embodiment of the present disclosure, and is not meant in any way to restrict the scope of the invention.
  • the organic electroluminescent device may be embodied in another way.
  • the HOMO and LUMO energy levels of the present disclosure were measured by using the density functional theory (DFT) in the program of Gaussian 03 of Gaussian, Inc. Specifically, the HOMO and LUMO energy values of the Examples and the Comparative Examples of the present disclosure were extracted from the structure having the lowest energy among the calculated energies of the conformational isomers after structurally optimizing the structures of all of the possible conformational isomers at the level of B3LYP/6-31g*.
  • DFT density functional theory
  • An OLED device was produced as follows.
  • a transparent electrode indium tin oxide (ITO) thin film (10 ⁇ /sq) on a glass substrate for an organic light-emitting diode (OLED) device (Geomatec, Japan) was subjected to an ultrasonic washing with acetone and isopropanol, sequentially, and was then stored in isopropanol.
  • the ITO substrate was mounted on a substrate holder of a vacuum vapor depositing apparatus.
  • Compound HI-1 was introduced into a cell of said vacuum vapor depositing apparatus, and then the pressure in the chamber of said apparatus was controlled to 10 -6 torr.
  • the second hole transport material of Table 1 below was introduced into another cell of said vacuum vapor depositing apparatus, and was evaporated by applying an electric current to the cell, thereby forming a second hole transport layer having a thickness of 60 nm on the first hole transport layer.
  • a light-emitting layer was then deposited as follows.
  • Compound H-139 as below was introduced into one cell of the vacuum vapor depositing apparatus as a host of the light-emitting layer, and compound D-39 was introduced into another cell as a dopant.
  • the two materials were evaporated at different rates and were deposited in a doping amount of 2 wt% (the amount of dopant) based on the total amount of the host and dopant to form a light-emitting layer having a thickness of 40 nm on the second hole transport layer.
  • Compound ET-1 and compound EI-1 were then introduced into another two cells, evaporated at the rate of 1:1, and deposited to form an electron transport layer having a thickness of 35 nm on the light-emitting layer.
  • an Al cathode having a thickness of 80 nm was deposited by another vacuum vapor deposition apparatus on the electron injection layer.
  • an OLED device was produced.
  • the driving voltage, luminous efficiency, and CIE color coordinates based on a luminance of 1,000 nits, and the lifespan (measured as the luminance dropped from 100% after 16.7 hours at 5,000 nits and a constant current) of the OLEDs are shown in Table 1 below.
  • Comparative Example 1 Production of an OLED device not according to
  • OLED device was produced in the same manner as in Device Example 1, except for using another material for the second hole transport material, and the evaluation result of the device is shown in Table 1 below.
  • the compounds used in the second hole transport layer of Examples 1 to 4 have lower HOMO energy values than the compound used in the second hole transport layer of Comparative Example 1. This contributes to an increase of the hole transport ability between the second hole transport layer and the light-emitting layer.
  • the second hole transport layers of the organic electroluminescent devices of Examples 1 to 4 have HOMO energy values of -4.6 to -5.0 eV to show superior efficiency characteristic at the condition of equivalent or longer lifespan and equivalent or lower driving voltage compared to Comparative Example 1 (but not limited by the theory).

Abstract

La présente invention concerne un dispositif électroluminescent organique comprenant une couche électroluminescente et une zone de transport de trous. En comprenant la combinaison de la couche électroluminescente et de la zone de transport de trous ayant une certaine valeur d'énergie HOMO selon la présente invention, un dispositif électroluminescent organique ayant un excellent rendement lumineux tout en maintenant une excellente durée de vie ou une excellente caractéristique de tension d'attaque du dispositif peut être fourni.
PCT/KR2018/003101 2017-03-16 2018-03-16 Dispositif électroluminescent organique WO2018169352A1 (fr)

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JP2019546890A JP7057369B2 (ja) 2017-03-16 2018-03-16 有機エレクトロルミネセントデバイス
CN201880012803.5A CN110313079B (zh) 2017-03-16 2018-03-16 有机电致发光装置
US16/492,632 US20200058882A1 (en) 2017-03-16 2018-03-16 Organic electroluminescent device

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KR1020180026943A KR102550843B1 (ko) 2017-03-16 2018-03-07 유기 전계 발광 소자

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Cited By (3)

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Publication number Priority date Publication date Assignee Title
WO2020085793A1 (fr) * 2018-10-24 2020-04-30 덕산네오룩스 주식회사 Composé pour élément électronique organique, élément électronique organique l'utilisant, et dispositif électronique le comprenant
US11608344B2 (en) 2020-05-04 2023-03-21 Amgen Inc. Heterocyclic compounds as triggering receptor expressed on myeloid cells 2 agonists and methods of use
US11718617B2 (en) 2020-05-04 2023-08-08 Amgen Inc. Heterocyclic compounds as triggering receptor expressed on myeloid cells2 agonists and methods of use

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WO2015182994A1 (fr) * 2014-05-27 2015-12-03 Rohm And Haas Electronic Materials Korea Ltd. Composé électroluminescent organique et dispositif électroluminescent organique comprenant ce composé
WO2016148390A1 (fr) * 2015-03-13 2016-09-22 Rohm And Haas Electronic Materials Korea Ltd. Pluralité de matériaux hôtes et dispositif électroluminescent organique comprenant ces matériaux
WO2017014546A1 (fr) * 2015-07-20 2017-01-26 Rohm And Haas Electronic Materials Korea Ltd. Matériau luminescent pour fluorescence retardée et dispositif électroluminescent organique comprenant ce dernier

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Publication number Priority date Publication date Assignee Title
WO2015182994A1 (fr) * 2014-05-27 2015-12-03 Rohm And Haas Electronic Materials Korea Ltd. Composé électroluminescent organique et dispositif électroluminescent organique comprenant ce composé
WO2016148390A1 (fr) * 2015-03-13 2016-09-22 Rohm And Haas Electronic Materials Korea Ltd. Pluralité de matériaux hôtes et dispositif électroluminescent organique comprenant ces matériaux
WO2017014546A1 (fr) * 2015-07-20 2017-01-26 Rohm And Haas Electronic Materials Korea Ltd. Matériau luminescent pour fluorescence retardée et dispositif électroluminescent organique comprenant ce dernier

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2020085793A1 (fr) * 2018-10-24 2020-04-30 덕산네오룩스 주식회사 Composé pour élément électronique organique, élément électronique organique l'utilisant, et dispositif électronique le comprenant
US11608344B2 (en) 2020-05-04 2023-03-21 Amgen Inc. Heterocyclic compounds as triggering receptor expressed on myeloid cells 2 agonists and methods of use
US11718617B2 (en) 2020-05-04 2023-08-08 Amgen Inc. Heterocyclic compounds as triggering receptor expressed on myeloid cells2 agonists and methods of use
US11884675B2 (en) 2020-05-04 2024-01-30 Amgen Inc. Heterocyclic compounds as triggering receptor expressed on myeloid cells 2 agonists and methods of use
US11912711B2 (en) 2020-05-04 2024-02-27 Amgen Inc. Heterocyclic compounds as triggering receptor expressed on myeloid cells 2 agonists and methods of use

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