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WO2016080749A1 - Pluralité de matières dopantes et dispositif électroluminescent organique comprenant ces matières - Google Patents

Pluralité de matières dopantes et dispositif électroluminescent organique comprenant ces matières Download PDF

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Publication number
WO2016080749A1
WO2016080749A1 PCT/KR2015/012380 KR2015012380W WO2016080749A1 WO 2016080749 A1 WO2016080749 A1 WO 2016080749A1 KR 2015012380 W KR2015012380 W KR 2015012380W WO 2016080749 A1 WO2016080749 A1 WO 2016080749A1
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unsubstituted
substituted
alkyl
aryl
independently
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Sung-Woo Jang
Hong-Yeop NA
Bitnari Kim
Hee-Ryong Kang
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DuPont Specialty Materials Korea Ltd
DuPont Electronic Materials International LLC
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Rohm and Haas Electronic Materials Korea Ltd
Rohm and Haas Electronic Materials LLC
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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
    • 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
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/18—Metal complexes
    • C09K2211/185—Metal complexes of the platinum group, i.e. Os, Ir, Pt, Ru, Rh or Pd
    • 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
    • H10K2101/10—Triplet emission
    • 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
    • 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
    • H10K85/631—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
    • H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
    • 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

Definitions

  • the present disclosure relates to a plurality of dopant materials and an organic electroluminescent device comprising the same.
  • An electroluminescent (EL) device is a self-light-emitting device which has advantages in that it provides a wider viewing angle, a greater contrast ratio, and a faster response time.
  • An organic EL device was first developed by Eastman Kodak, by using small aromatic diamine molecules and aluminum complexes as materials to form a light-emitting layer [Appl. Phys. Lett. 51, 913, 1987].
  • an organic EL device has a structure comprising an anode, a cathode, and an organic layer disposed between the two electrodes.
  • the organic layer may comprise a hole injection layer, a hole transport layer, an electron blocking layer, a light-emitting layer, a hole blocking layer, an electron transport layer, an electron injection layer, etc.
  • an organic EL device In an organic EL device, holes and electrons are injected from an anode and a cathode, respectively, to the light-emitting layer by applying electricity to an organic EL device; excitons having high energy are formed by recombinations between the holes and the electrons, which make organic light-emitting compounds be in an excited state, and the decay of the excited state results in a relaxation of the energy into a ground state, accompanied by light-emission. Therefore, the most important factor determining luminous efficiency in an organic EL device is a light-emitting material.
  • the light-emitting material can be classified according to its function, as a host material and a dopant material.
  • devices showing good electroluminescent characteristics comprise a light-emitting layer in which a dopant is doped into a host.
  • the dopant/host system is provided to enhance luminous efficiency through energy transfer from a host to a dopant.
  • the dopant and host materials highly affect efficiencies and performance of the device.
  • Iridium(III) complexes have been widely known as dopants of phosphorescent materials, including bis(2-(2’-benzothienyl)-pyridinato-N,C-3’)iridium(acetylacetonate) ((acac)Ir(btp) 2 ), tris(2-phenylpyridine)iridium (Ir(ppy) 3 ) and bis(4,6-difluorophenylpyridinato-N,C2)picolinate iridium (Firpic) as red-, green-, and blue-emitting materials, respectively.
  • CBP 4,4’-N,N’-dicarbazol-biphenyl
  • BCP bathocuproine
  • BAlq aluminum(III) bis(2-methyl-8-quinolinate)(4-phenylphenolate)
  • Korean Patent Application Laying-Open No. 2011-0086021, WO 2008/109824, and WO 2010/033550 disclose iridium complexes having 2-phenylquinoline-based ligand as a dopant compound for an organic electroluminescent device.
  • a dopant system which can provide good EL performances meeting EL characteristics level required for a medium- to large-sized OLED panel needs to be developed.
  • the object of the present disclosure is to provide an organic electroluminescent device showing excellence in lifespan, driving voltage, luminous efficiency such as current efficiency and power efficiency, color purity, solubility, and thermal stability.
  • an organic electroluminescent device comprising an anode, a cathode, and an organic layer disposed between the anode and cathode, wherein the organic layer comprises one or more light-emitting layers; and at least one light-emitting layer comprises one or more host compounds, and two or more dopant compounds represented by the following formula 1:
  • R 1 and R 2 each independently, represent hydrogen, a substituted or unsubstituted (C1-C6)alkyl, or a substituted or unsubstituted (C6-C30)aryl, provided that R 1 and R 2 are not simultaneously hydrogen;
  • R 3 and R 4 each independently, represent hydrogen, deuterium, a halogen, a substituted or unsubstituted (C1-C5)alkyl, or a substituted or unsubstituted (C6-C30)aryl;
  • R 5 to R 7 each independently, represent hydrogen, a substituted or unsubstituted (C1-C5)alkyl, or a substituted or unsubstituted (C6-C30)aryl;
  • a represents an integer of 0 to 2; where a is 2, each of R 3 may be the same or different;
  • b represents an integer of 0 to 3; and where b is 2 or more, each of R 4 may be the same or different.
  • An organic electroluminescent device of the present disclosure can show low driving voltage, long lifespan, and excellence in color purity, luminous efficiency such as current efficiency and power efficiency, solubility, and thermal stability. Particularly, an organic electroluminescent device maintaining high color purity and showing good current efficiency can be provided.
  • (C1-C5)alkyl, (C1-C6)alkyl, or (C1-C30)alkyl indicates a linear or branched alkyl having 1 to 5, 1 to 6, or 1 to 30 carbon atoms.
  • (C1-C5)alkyl includes methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 2,2-dimethylpropyl, and 1-ethylpropyl.
  • (C1-C6)alkyl includes n-hexyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl, 1-ethyl-1-methylpropyl, and 1-ethyl-2-methylpropyl, in addition to said (C1-C5)alkyl.
  • (C2-C30)alkenyl indicates a linear or branched alkenyl having 2 to 30, preferably 2 to 20, and more preferably 2 to 10 carbon atoms, and includes vinyl, 1-propenyl, 2-propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 2-methylbut-2-enyl, etc.
  • (C2-C30)alkynyl indicates a linear or branched alkynyl having 2 to 30, preferably 2 to 20, and more preferably 2 to 10 carbon atoms, and includes ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methylpent-2-ynyl, etc.
  • (C3-C30)cycloalkyl indicates a mono- or polycyclic hydrocarbon having 3 to 30, preferably 3 to 20, and more preferably 3 to 7 carbon atoms, and includes cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, etc.
  • “3- to 7-membered heterocycloalkyl” indicates a cycloalkyl having 3 to 7, preferably 5 to 7 ring backbone atoms including at least one hetero atom selected from the group consisting of B, N, O, S, Si, and P, preferably O, S, and N, and includes tetrahydrofuran, pyrrolidine, thiolan, tetrahydropyran, etc.
  • “Aryl(ene)” indicates a monocyclic or fused ring radical derived from an aromatic hydrocarbon.
  • (C6-C30)aryl(ene) has 6 to 30, preferably 6 to 20, and more preferably 6 to 15 ring backbone carbon atoms.
  • (C6-C60)aryl(ene) has 6 to 60, preferably 6 to 30, and more preferably 6 to 15 ring backbone carbon atoms.
  • Aryl includes phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, phenanthrenyl, anthracenyl, indenyl, triphenylenyl, pyrenyl, tetracenyl, perylenyl, chrysenyl, naphthacenyl, fluoranthenyl, etc.
  • “3- to 30-membered heteroaryl(ene)” indicates an aryl group having 3 to 30, preferably 5 to 20, and more preferably 5 to 18 ring backbone atoms including at least one, preferably 1 to 4, hetero atom selected from the group consisting of B, N, O, S, Si, and P; may be 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); and includes a monocyclic ring-type heteroaryl such as 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 group, i.e. a substituent.
  • the substituent may be at least one selected from the group consisting of a halogen; a cyano; a (C1-C20)alkyl; a halo(C1-C20)alkyl; a 5- to 20-membered heteroaryl unsubstituted or substituted with a (C1-C20)alkyl, a tri(C6-C20)arylsilyl, a (C1-C20)alkyldi(C6-C20)arylsilyl, a (C6-C20)aryl, a (C1-C20)alkyl(C6-C20)aryl, or a (C6-C20)aryl; a (C6-C20)aryl unsubstituted or substituted with a (C1-C20)alkyl, a halogen, a tri(C6-C20)arylsilyl, a (C6-C20)aryl, a
  • R 1 and R 2 each independently, may represent hydrogen, a substituted or unsubstituted (C1-C6)alkyl, or a substituted or unsubstituted (C6-C15)aryl. More preferably, R 1 and R 2 , each independently, may represent hydrogen, an unsubstitued (C1-C6)alkyl, or a (C6-C13)aryl unsubstituted or substituted with a (C1-C6)alkyl.
  • R 1 and R 2 may be selected from hydrogen; methyl; ethyl; n-propyl; isopropyl; n-butyl; a branched (C4-C6)alkyl; phenyl unsubstituted or substituted with a (C1-C6)alkyl; naphthyl unsubstituted or substituted with a (C1-C6)alkyl; and biphenyl unsubstituted or substituted with a (C1-C6)alkyl.
  • R 1 may be selected from hydrogen; methyl; ethyl; n-propyl; isopropyl; n-butyl; isobutyl; sec-butyl; tert-butyl; 1-methylbutyl; 2-methylbutyl; 3-methylbutyl; 1,1-dimethylpropyl; 1,2-dimethylpropyl; 2,2-dimethylpropyl; 1-ethylpropyl; 1,1-dimethylbutyl; 1,2-dimethylbutyl; 1,3-dimethylbutyl; 2,2-dimethylbutyl; 2,3-dimethylbutyl; 3,3-dimethylbutyl; 1-ethylbutyl; 2-ethylbutyl; 1,1,2-trimethylpropyl; 1,2,2-trimethylpropyl; 1-ethyl-1-methylpropyl; and 1-ethyl-2-methylpropyl.
  • R 2 may be selected from hydrogen; methyl; ethyl; n-propyl; isopropyl; n-butyl; isobutyl; sec-butyl; tert-butyl; 1-methylbutyl; 2-methylbutyl; 3-methylbutyl; 1,1-dimethylpropyl; 1,2-dimethylpropyl; 2,2-dimethylpropyl; 1-ethylpropyl; 1,1-dimethylbutyl; 1,2-dimethylbutyl; 1,3-dimethylbutyl; 2,2-dimethylbutyl; 2,3-dimethylbutyl; 3,3-dimethylbutyl; 1-ethylbutyl; 2-ethylbutyl; 1,1,2-trimethylpropyl; 1,2,2-trimethylpropyl; 1-ethyl-1-methylpropyl; 1-ethyl-2-methylpropyl; phenyl unsubstituted or substituted with methyl, ethyl,
  • R 3 may represent preferably, hydrogen, deuterium, a halogen, a substituted or unsubstituted (C1-C5)alkyl, or a substituted or unsubstituted (C6-C15)aryl; and more preferably, hydrogen, a halogen, an unsubstituted (C1-C5)alkyl, or a (C6-C13)aryl unsubstituted or substituted with a (C1-C5)alkyl.
  • R 3 may represent hydrogen, a halogen, an unsubstituted (C1-C5)alkyl, phenyl unsubstituted or substituted with a (C1-C5)alkyl, biphenyl unsubstituted or substituted with a (C1-C5)alkyl, or naphthyl unsubstituted or substituted with a (C1-C5)alkyl.
  • R 3 is not hydrogen, it is preferred that R 3 is bonded at 3, 6, or 7 position of the 2-phenylquinoline ligand of formula 1.
  • R 4 may represent preferably, hydrogen, or a substituted or unsubstituted (C1-C5)alkyl; and more preferably, hydrogen or an unsubstituted (C1-C5)alkyl.
  • phenyl comprising R 4 may be represented by any one of the following formulae A-1 to A-3:
  • R 5 and R 7 each independently, may represent a substituted or unsubstituted (C1-C5)alkyl, or a substituted or unsubstituted (C6-C15)aryl; and R 6 may represent hydrogen, a substituted or unsubstituted (C1-C5)alkyl, or a substituted or unsubstituted (C6-C15)aryl. More preferably, R 5 and R 7 , each independently, may represent an unsubstituted (C1-C5)alkyl; and R 6 may represent hydrogen. Preferably, R 5 and R 7 may be the same.
  • R 1 and R 2 each independently, may be selected from hydrogen, a substituted or unsubstituted (C1-C6)alkyl, or a substituted or unsubstituted (C6-C15)aryl, provided that R 1 and R 2 are not simultaneously hydrogen;
  • R 3 may represent hydrogen, deuterium, a halogen, a substituted or unsubstituted (C1-C5)alkyl, or a substituted or unsubstituted (C6-C15)aryl;
  • R 4 may represent hydrogen, or a substituted or unsubstituted (C1-C5)alkyl;
  • R 5 and R 7 each independently, may represent a substituted or unsubstituted (C1-C5)alkyl, or a substituted or unsubstituted (C6-C15)aryl; and
  • R 6 may represent hydrogen, a substituted or unsubstituted (C1-C5)alkyl, or
  • R 1 and R 2 each independently, may represent hydrogen, an unsubtituted (C1-C6)alkyl, or a (C6-C13)aryl unsubstituted or substituted with a (C1-C6)alkyl;
  • R 3 may represent hydrogen, a halogen, an unsubtituted (C1-C5)alkyl, or a (C6-C13)aryl unsubstituted or substituted with a (C1-C5)alkyl;
  • R 4 may represent hydrogen or an unsubstituted (C1-C5)alkyl;
  • R 5 and R 7 each independently, may represent an unsubstituted (C1-C5)alkyl; and
  • R 6 may represent hydrogen.
  • a first dopant compound of the two or more dopant compounds represented by formula 1 is a compound represented by formula 1 in which at least one of R 1 to R 3 represents a substituted or unsubstituted (C6-C15)aryl; and a second dopant compound is a compound represented by formula 1 in which R 1 to R 3 , each independently, represent hydrogen or a substituted or unsubstituted (C1-C5)alkyl, provided that R 1 and R 2 are not simultaneously hydrogen.
  • the compound of formula 1 includes the following, but is not limited thereto:
  • the one or more host compounds which are used with the two or more dopant compounds may be selected from compounds represented by the following formula 2:
  • Ma represents a substituted or unsubstituted, nitrogen-containing 5- to 11-membered heteroaryl
  • La represents a single bond, or a substituted or unsubstituted (C6-C30)arylene
  • Xa to Xh each independently, represent hydrogen, deuterium, a halogen, a cyano, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C2-C30)alkenyl, a substituted or unsubstituted (C2-C30)alkynyl, a substituted or unsubstituted (C3-C30)cycloalkyl, a substituted or unsubstituted (C6-C60)aryl, a substituted or unsubstituted 3- to 30-membered heteroaryl, a substituted or unsubstituted tri(C1-C30)alkylsilyl, a substituted or unsubstituted tri(C6-C30)arylsilyl, a substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, a substituted or un
  • the heteroaryl(ene) contains at least one hetero atom selected from B, N, O, S, Si, and P.
  • La may represent preferably, a single bond, or a substituted or unsubstituted (C6-C12)arylene; and more preferably, a single bond, or a (C6-C12)arylene unsubstituted or substituted with a tri(C6-C10)arylsilyl.
  • La may represent a single bond, a substituted or unsubstituted phenylene, a substituted or unsubstituted naphthylene, or a substituted or unsubstituted biphenylene.
  • Ma may represent preferably, a substituted or unsubstituted, nitrogen-containing 5- to 11-membered heteroaryl; and more preferably, a nitrogen-containing 6- to 11-membered heteroaryl unsubstitued or substituted with a cyano, a (C1-C6)alkyl, a tri(C6-C12)arylsilyl, a (C6-C18)aryl, or a 5- to 15-membered heteroaryl.
  • Ma may represent a substituted or unsubstituted pyrrolyl, a substituted or unsubstituted imidazolyl, a substituted or unsubstituted pyrazolyl, a substituted or unsubstituted triazinyl, a substituted or unsubstituted tetrazinyl, a substituted or unsubstituted triazolyl, a substituted or unsubstituted tetrazolyl, a substituted or unsubstituted pyridyl, a substituted or unsubstituted pyrazinyl, a substituted or unsubstituted pyrimidinyl, a substituted or unsubstituted pyridazinyl, a substituted or unsubstituted benzimidazolyl, a substituted or unsubstituted isoindolyl, a substituted or unsubstituted indolyl,
  • Ma may represent a substituted or unsubstituted triazinyl, a substituted or unsubstituted pyrimidinyl, a substituted or unsubstituted pyridyl, a substituted or unsubstituted quinolyl, a substituted or unsubstituted isoquinolyl, a substituted or unsubstituted quinazolinyl, a substituted or unsubstituted naphthyridinyl, or a substituted or unsubstituted quinoxalinyl.
  • Xa to Xh each independently, may represent hydrogen, a cyano, a substituted or unsubstituted (C6-C15)aryl, a substituted or unsubstituted 6- to 25-membered heteroaryl, or a substituted or unsubstituted tri(C6-C15)arylsilyl; or may be linked to an adjacent substituent(s) to form a substituted or unsubstituted 6- to 20-membered, mono- or polycyclic aromatic ring, whose carbon atom(s) may be replaced with at least one hetero atom selected from the group consisting of nitrogen, oxygen, and sulfur.
  • Xa to Xh each independently, may represent hydrogen, a cyano, a (C6-C15)aryl unsubstituted or substituted with a tri(C6-C12)arylsilyl, a 6- to 25-membered heteroaryl unsubstituted or substituted with a tri(C6-C12)arylsilyl or a (C6-C12)aryl, or a tri(C6-C12)arylsilyl; or may be linked to an adjacent substituent(s) to form a substituted or unsubstituted benzene, a substituted or unsubstituted indole, a substituted or unsubstituted benzindole, a substituted or unsubstituted indene, a substituted or unsubstituted benzofuran, or a substituted or unsubstituted benzothiophene.
  • At least one of Xa to Xh may represent a substituted or unsubstituted carbazole or a substituted or unsubstituted dibenzocarbazole; or may be linked to an adjacent substituent(s) to form a substituted or unsubstituted benzene, a substituted or unsubstituted indole, a substituted or unsubstituted benzindole, a substituted or unsubstituted indene, a substituted or unsubstituted benzofuran, or a substituted or unsubstituted benzothiophene.
  • one of Xa to Xh may be selected from the following formulae 3-1 to 3-3; and the remaining ones, each independently, may be hydrogen, a cyano, a substituted or unsubstituted (C6-C15)aryl, or a substituted or unsubstituted tri(C6-C15)arylsilyl, or may be linked to an adjacent substituent(s) to form a substituted or unsubstituted 6- to 20-membered mono- or polycyclic aromatic ring:
  • L b , L c , and L d each independently, represent a single bond, a substituted or unsubstituted (C6-C30)arylene, or a substituted or unsubstituted 3- to 30-membered heteroarylene;
  • Y represents -S-, -O-, or -NR 18 -;
  • R 11 to R 17 each independently, represent hydrogen, deuterium, a halogen, a cyano, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C3-C30)cycloalkyl, a substituted or unsubstituted (C3-C30)cycloalkenyl, a substituted or unsubstituted 3- to 7-membered heterocycloalkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted 3- to 30-membered heteroaryl, a substituted or unsubstituted tri(C1-C30)alkylsilyl, a substituted or unsubstituted tri(C6-C30)arylsilyl, a substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, a substitute
  • R 18 represents hydrogen, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted 3- to 30-membered heteroaryl, or a substituted or unsubstituted (C3-C30)cycloalkyl, or may be linked to an adjacent substituent(s) to form a substituted or unsubstituted 3- to 30-membered, mono- or polycyclic, alicyclic or aromatic ring;
  • c represents an integer of 1 to 3; d to f, and h, each independently, represent an integer of 1 to 4; g represents an integer of 1 to 5; and where c, d, e, f, g, or h is an integer of 2 or more, each of R 11 , R 12 , R 13 , R 14 , R 15 , or R 16 may be the same or different.
  • the host compound represented by formula 2 may be represented by the following formula 4:
  • La and Ma are as defined in formula 2 above;
  • Z represents -S-, -O-, -NR 24 -, or -CR 25 R 26 -;
  • R 21 to R 23 are defined in the same manner as the definitions of Xa to Xh;
  • the host compound represented by formula 2 may be specifically represented by the following formula 5:
  • R 21 to R 23 are defined in the same manner as the definitions of Xa to Xh;
  • R 24 may represent a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted 3- to 30-membered heteroaryl, or a substituted or unsubstituted (C3-C30)cycloalkyl; and i, j, and k are as defined in formula 4.
  • the compound of formula 2 includes the following, but is not limited thereto.
  • the compound of formula 1 and the compound of formula 2 of the present disclosure can be prepared by a synthetic method known to one skilled in the art, e.g., bromination, Suzuki reaction, Buchwald-Hartwig reaction, Ullmann reaction, etc.
  • the compound may be prepared by methods disclosed in Korean Patent Application Laying-Open No. 10-2011-0015836A.
  • the organic electroluminescent device of the present disclosure comprises an anode, a cathode, and an organic layer disposed between the anode and cathode, wherein the organic layer comprises one or more light-emitting layers; at least one light-emitting layer comprises one or more host compounds, and two or more dopant compounds represented by formula 1.
  • the light-emitting layer indicates a layer from which light is emitted.
  • a doping amount of the dopant compound is less than 20 wt%, preferably less than 17 wt%, based on the total amount of the host compound and the dopant compound.
  • the weight ratio between the first dopant material and the second dopant material is preferably in the range of 10:90 to 90:10, and preferably 30:70 to 70:30 in view of color purity, current efficiency, power efficiency, and driving voltage.
  • the organic layer may further comprise one or more layers selected from a hole injection layer, a hole transport layer, an electron transport layer, an electron injection layer, an electron buffering layer, an interlayer, a hole blocking layer, and an electron blocking layer, in addition to the light-emitting layer.
  • a combination of the two or more dopant compounds represented by formula 1 is provided.
  • the present disclosure provides an organic electroluminescent device comprising the combination of the two or more dopant compounds.
  • an organic electroluminescent material comprises the two or more dopant compounds represented by formula 1, and an organic electroluminescent device comprises the material.
  • an organic electroluminescent material comprises the two or more dopant compounds represented by formula 1, and an organic electroluminescent device comprises the material.
  • an organic electroluminescent material indicates a material which is used for organic electroluminescence.
  • the material may be the one for preparing an organic electroluminescent device.
  • the material may further comprise a conventional material which has been used to prepare an organic electroluminescent device.
  • the material may be a composition or a mixture.
  • an organic layer comprising one or more host compounds, and two or more dopant compounds represented by formula 1 is provided.
  • the organic layer may comprise a plurality of layers, in which the dopant compound and the host compound may be comprised in the same layer, or each of them may be comprised in different layers.
  • the present disclosure provides an organic electroluminescent device comprising the organic layer.
  • the organic layer may further comprise at least one compound selected from the group consisting of arylamine-based compounds and styrylarylamine-based compounds.
  • the organic layer may further comprise at least one metal selected from the group consisting of metals of Group 1, metals of Group 2, transition metals of the 4 th period, transition metals of the 5 th period, lanthanides and organic metals of the d-transition elements of the Periodic Table, or at least one complex compound comprising the metal.
  • the organic electroluminescent device of the present disclosure may emit white light by further comprising at least one light-emitting layer, which comprises a blue electroluminescent compound, a red electroluminescent compound or a green electroluminescent compound known in the art, besides the compounds of the present disclosure. If necessary, it may further comprise an orange light-emitting layer or a yellow light-emitting layer.
  • at least one light-emitting layer which comprises a blue electroluminescent compound, a red electroluminescent compound or a green electroluminescent compound known in the art, besides the compounds of the present disclosure. If necessary, it may further comprise an orange light-emitting layer or a yellow light-emitting layer.
  • a surface layer may be placed on an inner surface(s) of one or both electrode(s), selected from a chalcogenide layer, a metal halide layer, and a metal oxide layer.
  • a chalcogenide (includes oxides) layer of silicon or aluminum is preferably placed on an anode surface of an electroluminescent medium layer
  • a metal halide layer or a metal oxide layer is preferably placed on a cathode surface of an electroluminescent medium layer.
  • the chalcogenide includes SiO X (1 ⁇ X ⁇ 2), AlO X (1 ⁇ X ⁇ 1.5), SiON, SiAlON, etc.;
  • the metal halide includes LiF, MgF 2 , CaF 2 , a rare earth metal fluoride, etc.; and the metal oxide includes Cs 2 O, Li 2 O, MgO, SrO, BaO, CaO, etc.
  • a mixed region of an electron transport compound and a reductive dopant, or a mixed region of a hole transport compound and an oxidative dopant may be placed on at least one surface of a pair of electrodes.
  • the electron transport compound is reduced to an anion, and thus it becomes easier to inject and transport electrons from the mixed region to an electroluminescent medium.
  • the hole transport compound is oxidized to a cation, and thus it becomes easier to inject and transport holes from the mixed region to the electroluminescent medium.
  • the oxidative dopant includes various Lewis acids and acceptor compounds
  • the reductive dopant includes alkali metals, alkali metal compounds, alkaline earth metals, rare-earth metals, and mixtures thereof.
  • a reductive dopant layer may be employed as a charge generating layer to prepare an electroluminescent device having two or more light-emitting layers and emitting white light.
  • dry film-forming methods such as vacuum evaporation, sputtering, plasma and ion plating methods, or wet film-forming methods such as ink jet printing, nozzle printing, slot coating, spin coating, dip coating, and flow coating methods can be used.
  • a thin film can be formed by dissolving or diffusing materials forming each layer into any suitable solvent such as ethanol, chloroform, tetrahydrofuran, dioxane, etc.
  • the solvent can be any solvent where the materials forming each layer can be dissolved or diffused, and where there are no problems in film-formation capability.
  • two or more dopant compounds for a light-emitting layer may be co-evaporated or mixture-evaporated.
  • a co-evaporation indicates a process for two or more materials to be deposited as a mixture, by introducing each of the two or more materials into respective crucible cells, and applying electric current to the cells for each of the materials to be evaporated.
  • a mixture-evaporation indicates a process for two or more materials to be deposited as a mixture, by mixing the two or more materials in one crucible cell before the deposition, and applying electric current to the cell for the mixture to be evaporated.
  • a display system or a lighting system can be produced.
  • OLED was produced using the organic electroluminescent compounds of the present disclosure.
  • a transparent electrode indium tin oxide (ITO) thin film (10 ⁇ /sq) on a glass substrate for an organic light-emitting diode (OLED) (Geomatec) was subjected to an ultrasonic washing with acetone, ethanol, and distilled water, sequentially, and then was stored in isopropanol.
  • the ITO substrate was then mounted on a substrate holder of a vacuum vapor depositing apparatus.
  • HI-1 was introduced into a cell of the vacuum vapor depositing apparatus, and then the pressure in the chamber of said apparatus was controlled to 10 -6 torr.
  • HI-2 was introduced into another cell of the vacuum vapor depositing apparatus, and was evaporated by applying an electric current to the cell, thereby forming a second hole injection layer having a thickness of 5 nm on the first hole injection layer.
  • HT-1 was introduced into a cell of the vaccum vapor depositing apparatus, and was evaporated by applying an electric current to the cell, thereby forming a first hole transport layer having a thickness of 10 nm on the second hole injection layer.
  • HT-2 was introduced into another cell of the 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.
  • compound H2-41 was introduced into one cell of the vacuum vapor depositing apparatus as a host, and a dopant material shown in Table 1 below was introduced into another cell as a dopant. The two materials were evaporated at different rates, so that the dopant was deposited in a doping amount of 1.5 wt% 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.
  • ET-1 and EI-1 were introduced into two cells of the vacuum vapor depositing apparatus, respectively, and evaporated at a 1:1 rate to form an electron transport layer having a thickness of 30 nm on the light-emitting layer.
  • an Al cathode having a thickness of 80 nm was then deposited by another vacuum vapor deposition apparatus on the electron injection layer to produce OLED.
  • OLED was produced in the same manner as in Device Example 1-1, except that a dopant shown in Table 1 below was used as a dopant for a light-emitting layer.
  • the present disclosure employed both a dopant showing short-wavelength and high-efficiency and a dopant showing long-wavelength and relatively low-efficiency so as to provide a device having similar color purities to conventional materials of high color purities and high-efficiency.
  • comparative examples 1-1 and 1-2 employing a single dopant of D-1 or D-29 showed color coordinates of deep-red color having high color purity, but poor efficiency.
  • Comparative example 1-3 employing a single dopant D-10 showed good efficiency, but remarkably low color purity.
  • device example 1-1 employing a plurality of dopant compounds of the present disclosure provided a device showing improvement in efficiency, while maintaining the color coordinates of deep-red color (i.e., maintaining high color purity).

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

Abstract

La présente invention concerne une pluralité de matières dopantes et un dispositif électroluminescent organique les comprenant. Le dispositif électroluminescent organique de l'invention permet de maintenir une haute pureté des couleurs et présente une faible tension d'excitation, une longue durée de vie et d'excellentes caractéristiques en termes d'efficacité lumineuse, notamment de rendement en courant et de rendement en puissance, de solubilité et de stabilité thermique.
PCT/KR2015/012380 2014-11-18 2015-11-18 Pluralité de matières dopantes et dispositif électroluminescent organique comprenant ces matières Ceased WO2016080749A1 (fr)

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KR20140160652 2014-11-18
KR10-2014-0160652 2014-11-18
KR1020150160952A KR102603350B1 (ko) 2014-11-18 2015-11-17 복수종의 도판트 재료 및 이를 포함하는 유기 전계 발광 소자
KR10-2015-0160952 2015-11-17

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WO2018062758A1 (fr) * 2016-09-30 2018-04-05 Rohm And Haas Electronic Materials Korea Ltd. Matériau électroluminescent organique et dispositif électroluminescent organique le comprenant
CN109438468A (zh) * 2018-11-26 2019-03-08 浙江华显光电科技有限公司 一种磷光主体化合物及其使用该化合物的有机电致发光器件
CN109715759A (zh) * 2016-09-30 2019-05-03 罗门哈斯电子材料韩国有限公司 有机电致发光材料和包含所述材料的有机电致发光器件
CN111224005A (zh) * 2018-11-26 2020-06-02 三星显示有限公司 杂环化合物和包括该杂环化合物的有机发光器件
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US11117897B2 (en) 2017-05-01 2021-09-14 Universal Display Corporation Organic electroluminescent materials and devices
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CN109678875B (zh) * 2018-11-08 2022-05-20 浙江华显光电科技有限公司 一种磷光化合物和使用该化合物的有机发光二极管器件
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US12534665B2 (en) 2019-04-15 2026-01-27 Samsung Display Co., Ltd. Organometallic compound, organic light-emitting device including the same, and apparatus including the light-emitting device

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US10840458B2 (en) 2016-05-25 2020-11-17 Universal Display Corporation Organic electroluminescent materials and devices
CN109715759B (zh) * 2016-09-30 2023-05-12 罗门哈斯电子材料韩国有限公司 有机电致发光材料和包含所述材料的有机电致发光器件
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JP2019533035A (ja) * 2016-09-30 2019-11-14 ローム・アンド・ハース・エレクトロニック・マテリアルズ・コリア・リミテッド 有機エレクトロルミネッセンス材料およびそれを含む有機エレクトロルミネッセンス素子
EP3519532A4 (fr) * 2016-09-30 2020-05-06 Rohm And Haas Electronic Materials Korea Ltd. Matériau électroluminescent organique et dispositif électroluminescent organique le comprenant
WO2018062758A1 (fr) * 2016-09-30 2018-04-05 Rohm And Haas Electronic Materials Korea Ltd. Matériau électroluminescent organique et dispositif électroluminescent organique le comprenant
CN109715759A (zh) * 2016-09-30 2019-05-03 罗门哈斯电子材料韩国有限公司 有机电致发光材料和包含所述材料的有机电致发光器件
US11702420B2 (en) 2017-05-01 2023-07-18 Universal Display Corporation Organic electroluminescent materials and devices
US11117897B2 (en) 2017-05-01 2021-09-14 Universal Display Corporation Organic electroluminescent materials and devices
WO2019056515A1 (fr) * 2017-09-21 2019-03-28 南京工业大学 Composé hybridé à l'iridium coordonné à la quinoléine multi-substitué, son procédé de préparation et son application
CN107459535A (zh) * 2017-09-21 2017-12-12 南京工业大学 多取代喹啉配位的铱杂配化合物及其制备方法与应用
US20220384744A1 (en) * 2018-08-29 2022-12-01 Rohm And Haas Electronic Materials Korea Ltd. A plurality of host materials and organic electroluminescent device comprising the same
CN109678875B (zh) * 2018-11-08 2022-05-20 浙江华显光电科技有限公司 一种磷光化合物和使用该化合物的有机发光二极管器件
CN109678867B (zh) * 2018-11-08 2022-05-20 浙江华显光电科技有限公司 一种磷光化合物和使用该化合物的有机发光二极管器件
CN109438468A (zh) * 2018-11-26 2019-03-08 浙江华显光电科技有限公司 一种磷光主体化合物及其使用该化合物的有机电致发光器件
CN111224005A (zh) * 2018-11-26 2020-06-02 三星显示有限公司 杂环化合物和包括该杂环化合物的有机发光器件
EP4215536A1 (fr) * 2018-11-26 2023-07-26 Samsung Display Co., Ltd. Composé hétérocyclique et dispositif électroluminescent organique le comprenant
CN111224005B (zh) * 2018-11-26 2024-12-03 三星显示有限公司 杂环化合物和包括该杂环化合物的有机发光器件
US11637247B2 (en) 2018-11-28 2023-04-25 Samsung Sdi Co., Ltd. Compound for optoelectronic device and organic optoelectronic device and display device
US12534665B2 (en) 2019-04-15 2026-01-27 Samsung Display Co., Ltd. Organometallic compound, organic light-emitting device including the same, and apparatus including the light-emitting device

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