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WO2017086629A1 - A plurality of host materials and organic electroluminescent device comprising the same - Google Patents

A plurality of host materials and organic electroluminescent device comprising the same Download PDF

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Publication number
WO2017086629A1
WO2017086629A1 PCT/KR2016/012455 KR2016012455W WO2017086629A1 WO 2017086629 A1 WO2017086629 A1 WO 2017086629A1 KR 2016012455 W KR2016012455 W KR 2016012455W WO 2017086629 A1 WO2017086629 A1 WO 2017086629A1
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Prior art keywords
substituted
unsubstituted
integer
independently
host
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PCT/KR2016/012455
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French (fr)
Inventor
Young-Mook Lim
Bitnari Kim
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Rohm And Haas Electronic Materials Korea Ltd.
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Priority claimed from KR1020160120026A external-priority patent/KR102728866B1/en
Application filed by Rohm And Haas Electronic Materials Korea Ltd. filed Critical Rohm And Haas Electronic Materials Korea Ltd.
Priority to US15/774,288 priority Critical patent/US10454044B2/en
Priority to CN201680066231.XA priority patent/CN108291140B/en
Publication of WO2017086629A1 publication Critical patent/WO2017086629A1/en

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/04—Indoles; Hydrogenated indoles
    • C07D209/08—Indoles; Hydrogenated indoles with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to carbon atoms of the hetero ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/56—Ring systems containing three or more rings
    • C07D209/80—[b, c]- or [b, d]-condensed
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/56—Ring systems containing three or more rings
    • C07D209/80—[b, c]- or [b, d]-condensed
    • C07D209/82—Carbazoles; Hydrogenated carbazoles
    • C07D209/86—Carbazoles; Hydrogenated carbazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
    • C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
    • C07D491/04—Ortho-condensed systems
    • C07D491/044—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring
    • C07D491/048—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring the oxygen-containing ring being five-membered
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
    • C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
    • C07D495/04—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
    • 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
    • H10K85/649—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
    • 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
    • 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
    • H10K2101/00—Properties of the organic materials covered by group H10K85/00
    • H10K2101/90—Multiple hosts in the emissive layer
    • 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
    • H10K85/30—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

Definitions

  • the present disclosure relates to a plurality of host 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].
  • the organic EL device(OLED) converts electric energy into light when electricity is applied to an organic light-emitting material(s).
  • the organic EL device has a structure comprising an anode, a cathode, and an organic layer disposed between the anode and the cathode.
  • the organic layer of the organic EL device comprises a hole injection layer, a hole transport layer, an electron blocking layer, a light-emitting layer (comprising a host material and a dopant material), an electron buffering layer, a hole blocking layer, an electron transport layer, an electron injection layer, etc.
  • materials for forming the organic layer can be classified as a hole injection material, a hole transport material, an electron blocking material, a light-emitting material, an electron buffering material, a hole blocking material, an electron transport material, an electron injection material, etc.
  • a voltage is applied to the organic EL device, holes and electrons are injected from an anode and a cathode, respectively, to the light-emitting layer.
  • Excitons having high energy are formed by recombinations between the holes and the electrons, the energy puts the organic light-emitting compound in an excited state, and the decay of the excited state results in a relaxation of the energy level into a ground state, accompanied by light-emission.
  • the most important factor determining luminous efficiency in the organic EL device is light-emitting materials.
  • the light-emitting material needs to have high quantum efficiency, high electron mobility, and high hole mobility.
  • the light-emitting layer formed by the light-emitting material needs to be uniform and stable.
  • the light-emitting materials can be classified as a blue-, green-, or red-emitting material, and can additionally include a yellow- or orange-emitting material.
  • the light-emitting material can be classified according to its function, as a host material and a dopant material. Recently, the development of an OLED providing high efficiency and a long lifespan is urgent.
  • a host material which plays a role as a solvent in a solid state and transfers energy, should have high purity, and an appropriate molecular weight for being deposited under a vacuum.
  • a host material should have high glass transition temperature and high thermal decomposition temperature to ensure thermal stability; high electrochemical stability to have a long lifespan; ease of preparation for amorphous thin film; and good adhesion to materials of adjacent layers.
  • a host material should not move to an adjacent layer.
  • the light-emitting material can be prepared by combining a host with a dopant to improve color purity, luminous efficiency, and stability.
  • a device showing good EL performances comprises a light-emitting layer prepared by combining a host with a dopant.
  • the host material greatly influences the efficiency and lifespan of the EL device when using a host/dopant system, and thus its selection is important.
  • Korean Patent Application Laying-Open No. 10-2014-0096203 discloses an organic electroluminescent device using indole derivatives and biscarbazole compounds as a plurality of host materials. However, it does not specifically disclose an organic electroluminescent device comprising a compound having a structure wherein benzocarbazole and triazinyl are connected via a pyridine linker, as a host material.
  • the objective of the present disclosure is to provide an organic electroluminescent device that has luminous efficiency at least equivalent to or higher than conventional devices and has lifespan longer than conventional devices.
  • the present inventors found that the above objective can be achieved by a host material that comprises one or more first host compounds and one or more second host compounds wherein the first host compound is represented by the following formula 1 and the second host compound is represented by the following formula 2.
  • L 1 represents a single bond or a substituted or unsubstituted (C6-C30)arylene
  • A represents hydrogen, a substituted or unsubstituted phenyl, a substituted or unsubstituted naphthyl, a substituted or unsubstituted fluorenyl, a substituted or unsubstituted dibenzothiophenyl, or a substituted or unsubstituted dibenzofuranyl,
  • Ar 1 , Ar 2 and Ar 3 each independently, represent a substituted or unsubstituted (C6-C30)aryl(ene), or a substituted or unsubstituted 3- to 30-membered heteroaryl(ene); or Ar 2 and Ar 3 may be linked to form a substituted or unsubstituted 3 to 30-membered, mono- or polycyclic, alicyclic or aromatic ring, or a combination of the alicyclic ring and the aromatic ring, whose carbon atom(s) may be replaced with at least one heteroatom selected from the group consisting of nitrogen, oxygen, and sulfur,
  • R 1 represents 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-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, or a substituted or unsubstituted mono- or di
  • heteroaryl(ene) contains one or more heteroatoms selected from the group consisting of B, N, O, S, Si, and P,
  • a represents an integer of 0 to 4
  • each of R 1 may be the same or different;
  • Ar 4 and Ar 5 each independently, represent a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (C3-C30)cycloalkyl, or a substituted or unsubstituted 3- to 30-membered heteroaryl,
  • R 3 and R 4 each independently, represent 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-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, or a substituted or unsubstit
  • heteroaryl contains one or more heteroatoms selected from the group consisting of B, N, O, S, Si, and P, and
  • the present disclosure provides an organic electroluminescent device that has luminous efficiency at least equivalent to or higher than conventional devices and has lifespan longer than conventional devices. Furthermore, a display system or a lighting system using the organic electroluminescent device of the present disclosure can be produced.
  • L 1 may represent a single bond or a substituted or unsubstituted (C6-C30)arylene, preferably a single bond or a substituted or unsubstituted (C6-C25)arylene, more preferably a single bond or a substituted or unsubstituted (C6-C18)arylene, and may include a single bond, an unsubstituted phenylene, an unsubstituted naphthylene, and an unsubstituted biphenylene.
  • A may represent hydrogen, a substituted or unsubstituted phenyl, a substituted or unsubstituted naphthyl, a substituted or unsubstituted fluorenyl, a substituted or unsubstituted dibenzothiophenyl, or a substituted or unsubstituted dibenzofuranyl, preferably hydrogen, an unsubstituted phenyl, a fluorenyl substituted with one or more methyl, an unsubstituted naphthyl, an unsubstituted dibenzothiophenyl, or an unsubstituted dibenzofuranyl; and the substituted fluorenyl may be a fluorenyl substituted with dimethyl.
  • Ar 1 to Ar 3 each independently, may represent a substituted or unsubstituted (C6-C30)aryl(ene), or a substituted or unsubstituted 3 to 30-membered heteroaryl(ene);
  • Ar 2 and Ar 3 may be linked to form a substituted or unsubstituted 3 to 30-membered, mono- or polycyclic, alicyclic or aromatic ring, or a combination of the alicyclic ring and the aromatic ring, whose carbon atom(s) may be replaced with at least one heteroatom selected from the group consisting of nitrogen, oxygen, and sulfur;
  • Ar 1 to Ar 3 each independently, may represent a substituted or unsubstituted (C6-C25)aryl(ene);
  • Ar 2 and Ar 3 may be linked to form a substituted or unsubstituted 5 to 25-membered, mono- or polycyclic, alicyclic or aromatic ring, or a combination of the alicyclic ring and the
  • Ar 1 and Ar 2 may be a phenyl substituted or unsubstituted with naphthyl or phenanthrenyl, an unsubstituted biphenyl, an unsubstituted terphenyl, a fluorenyl substituted with dimethyl, or a benzofluorenyl substituted with dimethyl;
  • Ar 3 may represent an unsubstituted phenylene, an unsubstituted naphthylene, or a fluorenylene substituted with dimethyl; and Ar 2 and Ar 3 may be linked to form an unsubstituted carbazole.
  • R 1 may represent 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-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, or a substituted or unsubstituted mono
  • a represents an integer of 0 to 4, preferably an integer of 0 to 2; and when a is an integer of 2 or more, each of R 1 may be the same or different.
  • Ar 4 and Ar 5 each independently, may represent a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (C3-C30)cycloalkyl, or a substituted or unsubstituted 3- to 30-membered heteroaryl; preferably, each independently, may represent a substituted or unsubstituted (C6-C25)aryl; more preferably, each independently, may represent an unsubstituted (C6-C18)aryl, such as, an unsubstituted phenyl, an unsubstituted naphthyl, or an unsubstituted biphenyl.
  • R 3 and R 4 each independently, may represent 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-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, or a substituted or unsubsti
  • each of c or d represents an integer of 2 or more, each of R 3 or R 4 may be the same or different.
  • the heteroaryl contains one or more heteroatoms selected from the group consisting of B, N, O, S, Si, and P; preferably, one or more heteroatoms selected from the group consisting of N, O, and S.
  • the compound of formula 1 of the present disclosure may be represented by any one of the following formulae 3 to 7:
  • Ar 1 to Ar 3 each independently, may represent a substituted or unsubstituted (C6-C30)aryl(ene), or a substituted or unsubstituted 3 to 30-membered heteroaryl(ene); preferably, a substituted or unsubstituted (C6-C25)aryl(ene); more preferably a substituted or unsubstituted (C6-C20)aryl(ene); for example, Ar 1 and Ar 2 , each independently, may represent a phenyl substituted or unsubstituted with naphthyl or phenanthrenyl, an unsubstituted biphenyl, an unsubstituted terphenyl, a fluorenyl substituted with dimethyl, or a benzofluorenyl substituted with dimethyl; and Ar 3 may represent an unsubstituted phenylene, an unsubstituted naphthylene, or a fluoren
  • X may represent S, O or CR 7 R 8 , preferably S or O.
  • R 2 and R 5 to R 8 each independently, may represent 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-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 substituted or un
  • the heteroaryl contains one or more heteroatoms selected from the group consisting of B, N, O, S, Si, and P; preferably, one or more heteroatoms selected from the group consisting of N, O, and S.
  • b and f each independently, may represent an integer of 0 to 4, and e may represent an integer of 0 to 2; when each of b or f represents an integer of 2 or more, or when e represents an integer of 2, each of R 2 , R 5 , or R 6 may be the same or different.
  • b and f each independently, may represent an integer of 0 to 2
  • e may represent an integer of 0.
  • L 1 , R 1 , and a are as defined in formula 1 above.
  • the compound of formula 3 of the present disclosure may be represented by any one of the following formulae 8 to 10, and the compound of formula 4 of the present disclosure may be represented by the following formula 11:
  • R 9 to R 14 each independently, may represent 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-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, or or unsubstituted di
  • the heteroaryl contains one or more heteroatoms selected from the group consisting of B, N, O, S, Si, and P; preferably, one or more heteroatoms selected from the group consisting of N, O, and S.
  • g and h each independently, may represent an integer of 0 to 6; i and k, each independently, may represent an integer of 0 to 4; j and m, each independently, may represent an integer of 0 to 7; when each of g, h, i, j, k or m represents an integer of 2 or more, each of R 9 , R 10 , R 11 , R 12 , R 13 , or R 14 may be the same or different.
  • g, h, i, and k each independently, may represent 0, and, j and m, each independently, may represent 0 or 2.
  • L 1 , R 1 , R 2 , R 5 , R 6 , Ar 1 to Ar 3 , a, b, e, and f are as defined in formulae 3 to 7.
  • the compound of formula 2 of the present disclosure may be represented by any one of the following formulae 12 to 16:
  • R 3 , R 4 , Ar 4 , Ar 5 , c, and d are as defined in formula 2.
  • (C1-C30)alkyl indicates a linear or branched alkyl having 1 to 30, preferably 1 to 20, and more preferably 1 to 10 carbon atoms, and includes methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, etc.
  • “(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, preferabley 3 to 20, more preferably 3 to 7 ring backbone carbon atoms.
  • the cycloalkyl 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 heteroatom selected from B, N, O, S, Si, and P; preferably O, S, and N, and includes tetrahydrofuran, pyrrolidine, thiolan, tetrahydropyran, etc.
  • (C6-C30)aryl(ene) indicates a monocyclic ring-type or fused ring-type radical derived from aromatic hydrocarbon having 6 to 30, preferabley 6 to 20 ring backbone carbon atoms wherein the (C6-C30)aryl(ene) may be partially saturated.
  • the aryl includes phenyl, biphenyl, terphenyl, naphthyl, binaphthyl, phenylnaphthyl, naphthylphenyl, fluorenyl, phenylfluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, phenylphenanthrenyl, anthracenyl, indenyl, triphenylenyl, pyrenyl, tetracenyl, perylenyl, chrysenyl, naphthacenyl, fluoranthenyl, etc.
  • “3 to 30-membered heteroaryl(ene)” indicates an aryl group having 3 to 30 ring backbone atoms including at least one, preferably 1 to 4, heteroatoms 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, tetrazolyl, furazanyl,
  • 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 first host compound of formula 1 of the present disclosure includes the following, but is not limited thereto:
  • the second host compound of formula 2 above of the present disclosure 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.
  • a combination comprising the compound of formula 1 and the compound of formula 2 is provided.
  • the combination above may be a combination that is comprised in a light-emitting layer of an organic electroluminescent device.
  • the weight ratio in the light-emitting layer between the compound of formula 1 and the compound of formula 2 is in the range of 1:99 to 99:1, and preferably 30:70 to 70:30 in view of driving voltage, luminous efficiency, and lifespan.
  • the organic electroluminescent device of the present disclosure comprises an anode, a cathode, and one or more light-emitting layers disposed between the anode and cathode, wherein the light-emitting layers comprise a dopant and a host; the host comprises two or more host compounds; and a first host compound of the host compounds is represented by the formula 1 above; and a second host compound is represented by formula 2 above.
  • the light-emitting layer indicates a layer or plural layers consisting of two or more stacked layers, from which light is emitted. It is preferable that a doping amount of the dopant compound is less than 20 wt% based on the total amount of the host compound and the dopant compound.
  • the weight ratio in the light-emitting layer between the first host material and the second host material is in the range of 1:99 to 99:1, and preferably 30:70 to 70:30 in view of driving voltage, luminous efficiency, and lifespan.
  • the dopant for the organic electroluminescent device of the present disclosure is preferably one or more phosphorescent dopant compounds.
  • the phosphorescent dopant compound for the organic electroluminescent device of the present disclosure is not limited, but may be preferably selected from metallated complex compounds of iridium (Ir), osmium (Os), copper (Cu) or platinum (Pt), more preferably selected from ortho-metallated complex compounds of iridium (Ir), osmium (Os), copper (Cu) or platinum (Pt), and even more preferably ortho-metallated iridium complex compounds.
  • the phosphorescent dopant may be preferably selected from the compound of the following formulae 101 to 103:
  • L is selected from the following structures:
  • R 100 represents hydrogen, or a substituted or unsubstituted (C1-C30)alkyl
  • R 101 to R 109 and R 111 to R 123 each independently, represent hydrogen, deuterium, a halogen, a (C1-C30)alkyl substituted or unsubstituted with a halogen, a cyano, a substituted or unsubstituted (C1-C30)alkoxy, a substituted or unsubstituted (C3-C30)cycloalkyl, or a substituted or unsubstituted (C6-C30)aryl;
  • R 120 to R 123 each independently, 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, or a combination of the alicyclic ring and the aromatic ring, for example, a quinoline;
  • R 124 to R 127 each independently, represent hydrogen, deuterium, a halogen, a substituted or unsubstituted
  • the phosphorescent dopant includes the following:
  • the organic electroluminescent device of the present disclosure may further comprise at least one compound selected from the group consisting of arylamine-based compounds and styrylarylamine-based compounds in the organic layer.
  • 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.
  • 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 hole injection layer, a hole transport layer, a hole auxiliary layer, an auxiliary light-emitting layer, or an electron blocking layer, or a combination thereof may be disposed between the anode and the light-emitting layer.
  • the hole injection layer may be composed of two or more layers in order to lower an energy barrier for injecting holes from the anode to a hole transport layer or an electron blocking layer (or a voltage for injecting a hole). Each of the layers may comprise two or more compounds.
  • the hole transport layer or electron blocking layer may be composed of two or more layers. Wherein the hole auxiliary layer or the auxiliary light-emitting layer is disposed between the hole transport layer and the light-emitting layer, and modulates hole mobility.
  • the hole auxiliary layer or the auxiliary light-emitting layer has the effects to provide improved efficiency and lifespan of the organic electroluminescent device.
  • An electron buffering layer, a hole blocking layer, an electron transport layer, an electron injection layer, or a combination thereof may be disposed between the light-emitting layer and the cathode.
  • the electron buffering layer may be composed of two or more layers in order to control the electron injection and improve characteristics of interface between the light-emitting layer and the electron injection layer.
  • Each of the layers may comprise two or more compounds.
  • the hole blocking layer or electron transport layer may be composed of two or more layers, and each of the layers may comprise two or more compounds.
  • 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.
  • any of dry film-forming methods such as vacuum evaporation, sputtering, plasma, and ion plating methods, or wet film-forming methods such as spin coating, dip coating, and flow coating methods can be used.
  • a co-evaporation or a mixture-evaporation is used for forming a film of the first host material and a film of the second host material.
  • the 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 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.
  • a display system or a lighting system using the organic electroluminescent device of the present disclosure can be produced.
  • organic electroluminescent compound of the present disclosure the preparation method and the physical properties of the compound, and the luminescent properties of the organic electroluminescent device comprising the compound will be explained in detail with reference to the following examples.
  • OLED comprising a first host compound and a
  • An OLED was produced using the organic electroluminescent compound of the present disclosure as follows.
  • a transparent electrode indium tin oxide (ITO) thin film (10 ⁇ /sq) on a glass substrate for an OLED (Geomatec) was subjected to an ultrasonic washing with acetone, ethanol, and distilled water sequentially, and was then 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 said vacuum vapor depositing apparatus, and then the pressure in the chamber of said apparatus was controlled to 10 -6 torr.
  • HI-2 was then introduced into another cell of said vacuum vapor depositing apparatus, and evaporated by applying 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 one cell of the vacuum vapor depositing apparatus, and evaporated by applying 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-3 was introduced into another cell of the vacuum vapor depositing apparatus, and evaporated by applying 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 deposited thereon as follows.
  • a first host material and a second host material shown in Table 1 below were introduced, as host materials, into a cell of the vacuum vapor depositing apparatus, and compound D-71 was introduced, as a dopant, into another cell.
  • the two host compounds were then evaporated at the same rate of 1:1, so that the dopant was deposited in a doping amount of 3 wt% based on the total amount of the host and dopant to form a light-emitting layer having a thickness of 40nm on the second hole transport layer.
  • Compounds ET-1 and El-1 were then introduced into another two cells of the vacuum vapor depositing apparatus, respectively, and evaporated at the same rate of 1:1, thereby forming an electron transport layer having a thickness of 30nm on the light-emitting layer.
  • OLED comprising a first host compound and a
  • OLEDs were produced in the same manner as in Device Examples 1 to 4, except that a first hole injection layer having a thickness of 90nm was formed, the doping amount of the dopant was 2 wt%, an electron transport layer having a thickness of 35 nm was deposited, and the first host was changed as shown in Table 2 below. Evaluation results of the devices produced in Device Examples 5 to 8 are shown in Table 2 below.
  • An OLED was produced in the same manner as in Device Examples 1 to 4, except that the first host shown in Table 3 below was employed as a host for a light-emitting layer and the second host was not employed.
  • An OLED was produced in the same manner as in Device Examples 1 to 4, except that the second host shown in Table 4 below was employed as a host for a light-emitting layer and the first host was not employed.
  • An OLED was produced in the same manner as in Device Examples 1 to 4, except that the first host and the second host shown in Table 5 below were employed as a host for a light-emitting layer.
  • the organic electroluminescent device of the present disclosure has luminous efficiency at least equivalent to or higher than conventional devices and has lifespan longer than conventional devices.

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Abstract

The present disclosure relates to a host material and an organic electroluminescent device comprising the same. By using a specific combination of two or more host compounds according to the present disclosure, the organic electroluminescent device of the present disclosure has luminous efficiency at least equivalent to or higher than conventional devices and has lifespan better than conventional devices.

Description

A PLURALITY OF HOST MATERIALS AND ORGANIC ELECTROLUMINESCENT DEVICE COMPRISING THE SAME
The present disclosure relates to a plurality of host 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].
The organic EL device(OLED) converts electric energy into light when electricity is applied to an organic light-emitting material(s). Generally, the organic EL device has a structure comprising an anode, a cathode, and an organic layer disposed between the anode and the cathode. The organic layer of the organic EL device comprises a hole injection layer, a hole transport layer, an electron blocking layer, a light-emitting layer (comprising a host material and a dopant material), an electron buffering layer, a hole blocking layer, an electron transport layer, an electron injection layer, etc. Depending on its function, materials for forming the organic layer can be classified as a hole injection material, a hole transport material, an electron blocking material, a light-emitting material, an electron buffering material, a hole blocking material, an electron transport material, an electron injection material, etc. When a voltage is applied to the organic EL device, holes and electrons are injected from an anode and a cathode, respectively, to the light-emitting layer. Excitons having high energy are formed by recombinations between the holes and the electrons, the energy puts the organic light-emitting compound in an excited state, and the decay of the excited state results in a relaxation of the energy level into a ground state, accompanied by light-emission.
The most important factor determining luminous efficiency in the organic EL device is light-emitting materials. The light-emitting material needs to have high quantum efficiency, high electron mobility, and high hole mobility. Furthermore, the light-emitting layer formed by the light-emitting material needs to be uniform and stable. Depending on the colors visualized by light-emission, the light-emitting materials can be classified as a blue-, green-, or red-emitting material, and can additionally include a yellow- or orange-emitting material. Furthermore, the light-emitting material can be classified according to its function, as a host material and a dopant material. Recently, the development of an OLED providing high efficiency and a long lifespan is urgent. In particular, considering EL requirements for a middle or large-sized OLED panel, materials showing better performance than conventional ones must be urgently developed. In order to achieve the development, a host material which plays a role as a solvent in a solid state and transfers energy, should have high purity, and an appropriate molecular weight for being deposited under a vacuum. In addition, a host material should have high glass transition temperature and high thermal decomposition temperature to ensure thermal stability; high electrochemical stability to have a long lifespan; ease of preparation for amorphous thin film; and good adhesion to materials of adjacent layers. Furthermore, a host material should not move to an adjacent layer.
The light-emitting material can be prepared by combining a host with a dopant to improve color purity, luminous efficiency, and stability. Generally, a device showing good EL performances comprises a light-emitting layer prepared by combining a host with a dopant. The host material greatly influences the efficiency and lifespan of the EL device when using a host/dopant system, and thus its selection is important.
Korean Patent Application Laying-Open No. 10-2014-0096203 discloses an organic electroluminescent device using indole derivatives and biscarbazole compounds as a plurality of host materials. However, it does not specifically disclose an organic electroluminescent device comprising a compound having a structure wherein benzocarbazole and triazinyl are connected via a pyridine linker, as a host material.
The objective of the present disclosure is to provide an organic electroluminescent device that has luminous efficiency at least equivalent to or higher than conventional devices and has lifespan longer than conventional devices.
As a result of an earnest study for solving the above-described problems, the present inventors found that the above objective can be achieved by a host material that comprises one or more first host compounds and one or more second host compounds wherein the first host compound is represented by the following formula 1 and the second host compound is represented by the following formula 2.
Figure PCTKR2016012455-appb-I000001
wherein
L1 represents a single bond or a substituted or unsubstituted (C6-C30)arylene,
A represents hydrogen, a substituted or unsubstituted phenyl, a substituted or unsubstituted naphthyl, a substituted or unsubstituted fluorenyl, a substituted or unsubstituted dibenzothiophenyl, or a substituted or unsubstituted dibenzofuranyl,
Ar1, Ar2 and Ar3, each independently, represent a substituted or unsubstituted (C6-C30)aryl(ene), or a substituted or unsubstituted 3- to 30-membered heteroaryl(ene); or Ar2 and Ar3 may be linked to form a substituted or unsubstituted 3 to 30-membered, mono- or polycyclic, alicyclic or aromatic ring, or a combination of the alicyclic ring and the aromatic ring, whose carbon atom(s) may be replaced with at least one heteroatom selected from the group consisting of nitrogen, oxygen, and sulfur,
R1 represents 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-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, or a substituted or unsubstituted mono- or di-(C6-C30)arylamino; or R1 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, or a combination of the alicyclic ring and the aromatic ring,
wherein the heteroaryl(ene) contains one or more heteroatoms selected from the group consisting of B, N, O, S, Si, and P,
a represents an integer of 0 to 4,
and when a is an integer of 2 or more, each of R1 may be the same or different;
Figure PCTKR2016012455-appb-I000002
wherein
Ar4 and Ar5, each independently, represent a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (C3-C30)cycloalkyl, or a substituted or unsubstituted 3- to 30-membered heteroaryl,
R3 and R4, each independently, represent 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-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, or a substituted or unsubstituted mono- or di-(C6-C30)arylamino,
wherein the heteroaryl contains one or more heteroatoms selected from the group consisting of B, N, O, S, Si, and P, and
c represents an integer of 0 to 4; d represents an integer of 0 to 6; and when c or d is an integer of 2 or more, each of R3 or R4 may be the same or different.
The present disclosure provides an organic electroluminescent device that has luminous efficiency at least equivalent to or higher than conventional devices and has lifespan longer than conventional devices. Furthermore, a display system or a lighting system using the organic electroluminescent device of the present disclosure can be produced.
Hereinafter, the present disclosure will be described in detail. However, the following description is intended to explain the invention, and is not meant in any way to restrict the scope of the invention.
The host materials that comprise organic electroluminescent compounds represented by formula 1 above and represented by formula 2 above will be described in detail.
In formula 1, L1 may represent a single bond or a substituted or unsubstituted (C6-C30)arylene, preferably a single bond or a substituted or unsubstituted (C6-C25)arylene, more preferably a single bond or a substituted or unsubstituted (C6-C18)arylene, and may include a single bond, an unsubstituted phenylene, an unsubstituted naphthylene, and an unsubstituted biphenylene.
In formula 1, A may represent hydrogen, a substituted or unsubstituted phenyl, a substituted or unsubstituted naphthyl, a substituted or unsubstituted fluorenyl, a substituted or unsubstituted dibenzothiophenyl, or a substituted or unsubstituted dibenzofuranyl, preferably hydrogen, an unsubstituted phenyl, a fluorenyl substituted with one or more methyl, an unsubstituted naphthyl, an unsubstituted dibenzothiophenyl, or an unsubstituted dibenzofuranyl; and the substituted fluorenyl may be a fluorenyl substituted with dimethyl.
In formula 1, Ar1 to Ar3, each independently, may represent a substituted or unsubstituted (C6-C30)aryl(ene), or a substituted or unsubstituted 3 to 30-membered heteroaryl(ene); Ar2 and Ar3 may be linked to form a substituted or unsubstituted 3 to 30-membered, mono- or polycyclic, alicyclic or aromatic ring, or a combination of the alicyclic ring and the aromatic ring, whose carbon atom(s) may be replaced with at least one heteroatom selected from the group consisting of nitrogen, oxygen, and sulfur; preferably, Ar1 to Ar3, each independently, may represent a substituted or unsubstituted (C6-C25)aryl(ene); Ar2 and Ar3 may be linked to form a substituted or unsubstituted 5 to 25-membered, mono- or polycyclic, alicyclic or aromatic ring, or a combination of the alicyclic ring and the aromatic ring, whose carbon atom(s) may be replaced with at least one heteroatom selected from the group consisting of nitrogen, oxygen, and sulfur; more preferably, Ar1 to Ar3, each independently, may represent a substituted or unsubstituted (C6-C20)aryl(ene); Ar2 and Ar3 may be linked to form a substituted or unsubstituted 5 to 20-membered, mono- or polycyclic, alicyclic or aromatic ring, or a combination of the alicyclic ring and the aromatic ring, whose carbon atom(s) may be replaced with nitrogen. For example, Ar1 and Ar2 may be a phenyl substituted or unsubstituted with naphthyl or phenanthrenyl, an unsubstituted biphenyl, an unsubstituted terphenyl, a fluorenyl substituted with dimethyl, or a benzofluorenyl substituted with dimethyl; Ar3 may represent an unsubstituted phenylene, an unsubstituted naphthylene, or a fluorenylene substituted with dimethyl; and Ar2 and Ar3 may be linked to form an unsubstituted carbazole.
In formula 1, R1 may represent 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-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, or a substituted or unsubstituted mono- or di-(C6-C30)arylamino; or R1 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, or a combination of the alicyclic ring and the aromatic ring; preferably, R1 may be linked to an adjacent substituent(s) to form a substituted or unsubstituted 5 to 25-membered, mono- or polycyclic aromatic ring; more preferably, R1 may be linked to an adjacent substituent(s) to form a substituted or unsubstituted 5 to 18-membered, mono- or polycyclic, aromatic ring; specifically, the aromatic ring formed by linking the adjacent substituents may be selected from the group consisiting of a benzene, an indole, an indene, a benzofuran and a bezothiophene, substituted or unsubstituted with a (C1-C10)alkyl or a (C6-C15)aryl; for example, the adjacent substituents may be linked to form an unsubstituted benzene, an indene substituted with dimethyl, an unsubstituted benzofuran or an unsubstituted benzothiophene.
In formula 1, a represents an integer of 0 to 4, preferably an integer of 0 to 2; and when a is an integer of 2 or more, each of R1 may be the same or different.
In formula 2, Ar4 and Ar5, each independently, may represent a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (C3-C30)cycloalkyl, or a substituted or unsubstituted 3- to 30-membered heteroaryl; preferably, each independently, may represent a substituted or unsubstituted (C6-C25)aryl; more preferably, each independently, may represent an unsubstituted (C6-C18)aryl, such as, an unsubstituted phenyl, an unsubstituted naphthyl, or an unsubstituted biphenyl.
In formula 2, R3 and R4, each independently, may represent 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-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, or a substituted or unsubstituted mono- or di-(C6-C30)arylamino; preferably, each independently, may represent a substituted or unsubstituted (C6-C25)aryl; or more preferably, each independently, may represent an unsubstituted (C6-C20)aryl, such as an unsubstituted phenyl, or an unsubstituted terphenyl .
In formula 2, c may represent an integer of 0 to 4; d may represent an integer of 0 to 6; preferably, c and d, each independently, may represent 0 or 2; more preferably, c and d, each independently, may represent 0 or 1. When each of c or d represents an integer of 2 or more, each of R3 or R4 may be the same or different.
In formulae 1 and 2, the heteroaryl contains one or more heteroatoms selected from the group consisting of B, N, O, S, Si, and P; preferably, one or more heteroatoms selected from the group consisting of N, O, and S.
The compound of formula 1 of the present disclosure may be represented by any one of the following formulae 3 to 7:
Figure PCTKR2016012455-appb-I000003
Figure PCTKR2016012455-appb-I000004
Figure PCTKR2016012455-appb-I000005
Figure PCTKR2016012455-appb-I000006
Figure PCTKR2016012455-appb-I000007
In formulae 3 to 7, Ar1 to Ar3, each independently, may represent a substituted or unsubstituted (C6-C30)aryl(ene), or a substituted or unsubstituted 3 to 30-membered heteroaryl(ene); preferably, a substituted or unsubstituted (C6-C25)aryl(ene); more preferably a substituted or unsubstituted (C6-C20)aryl(ene); for example, Ar1 and Ar2, each independently, may represent a phenyl substituted or unsubstituted with naphthyl or phenanthrenyl, an unsubstituted biphenyl, an unsubstituted terphenyl, a fluorenyl substituted with dimethyl, or a benzofluorenyl substituted with dimethyl; and Ar3 may represent an unsubstituted phenylene, an unsubstituted naphthylene, or a fluorenylene substituted with dimethyl.
In formulae 4 and 6, X may represent S, O or CR7R8, preferably S or O.
In formulae 3 to 6, R2 and R5 to R8, each independently, may represent 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-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, or a substituted or unsubstituted mono- or di-(C6-C30)arylamino; or R2 and R5 to R8, each independently, 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, or a combination of the alicyclic ring and the aromatic ring, whose carbon atom(s) may be replaced with at least one heteroatom selected from the group consisting of nitrogen, oxygen, and sulfur; or preferably, R2 and R5 to R8, each independently, may represent a substituted or unsubstituted (C1-C20)alkyl; or R2 and R5 to R8, each independently, may be linked to an adjacent substituent(s) to form a substituted or unsubstituted 5 to 25-membered, mono- or polycyclic, aromatic ring, whose carbon atom(s) may be replaced with at least one heteroatom selected from the group consisting of nitrogen, oxygen, and sulfur; or more preferably, R2 and R5 to R8, each independently, may be linked to an adjacent substituent(s) to form a substituted or unsubstituted 5 to 18-membered, mono- or polycyclic, aromatic ring; for example, the adjacent substituents may be linked to form an unsubstituted benzene ring, or an indene ring substituted with dimethyl.
In formulae 3 to 7, the heteroaryl contains one or more heteroatoms selected from the group consisting of B, N, O, S, Si, and P; preferably, one or more heteroatoms selected from the group consisting of N, O, and S.
In formulae 3 to 7, b and f, each independently, may represent an integer of 0 to 4, and e may represent an integer of 0 to 2; when each of b or f represents an integer of 2 or more, or when e represents an integer of 2, each of R2, R5, or R6 may be the same or different. Preferably, b and f, each independently, may represent an integer of 0 to 2, and e may represent an integer of 0.
In formulae 3 to 7, L1, R1, and a are as defined in formula 1 above.
The compound of formula 3 of the present disclosure may be represented by any one of the following formulae 8 to 10, and the compound of formula 4 of the present disclosure may be represented by the following formula 11:
Figure PCTKR2016012455-appb-I000008
Figure PCTKR2016012455-appb-I000009
Figure PCTKR2016012455-appb-I000010
Figure PCTKR2016012455-appb-I000011
In formulae 8 to 11, R9 to R14, each independently, may represent 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-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, or a substituted or unsubstituted mono- or di-(C6-C30)arylamino; R9 to R14, each independently, 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, or a combination of the alicyclic ring and the aromatic ring, whose carbon atom(s) may be replaced with at least one heteroatom selected from the group consisting of nitrogen, oxygen, and sulfur; preferably, R9 to R14, each independently, may be linked to an adjacent substituent(s) to form a substituted or unsubstituted 5 to 25-membered, mono- or polycyclic, aromatic ring, whose carbon atom(s) may be replaced with at least one heteroatom selected from the group consisting of nitrogen, oxygen, and sulfur; or more preferably, R9 to R14, each independently, may be linked to an adjacent substituent(s) to form an unsubstituted 5 to 18-membered, mono- or polycyclic, aromatic ring; for example, R9 to R14, each independently, may be linked to an adjacent substituent(s) to form an unsubstituted benzene ring.
In formulae 8 to 11, the heteroaryl contains one or more heteroatoms selected from the group consisting of B, N, O, S, Si, and P; preferably, one or more heteroatoms selected from the group consisting of N, O, and S.
In formulae 8 to 11, g and h, each independently, may represent an integer of 0 to 6; i and k, each independently, may represent an integer of 0 to 4; j and m, each independently, may represent an integer of 0 to 7; when each of g, h, i, j, k or m represents an integer of 2 or more, each of R9, R10, R11, R12, R13, or R14 may be the same or different. Preferably, g, h, i, and k, each independently, may represent 0, and, j and m, each independently, may represent 0 or 2.
In formulae 8 to 11, L1, R1, R2, R5, R6, Ar1 to Ar3, a, b, e, and f are as defined in formulae 3 to 7.
According to one embodiment of the present disclosure, the compound of formula 2 of the present disclosure may be represented by any one of the following formulae 12 to 16:
Figure PCTKR2016012455-appb-I000012
Figure PCTKR2016012455-appb-I000013
Figure PCTKR2016012455-appb-I000014
In formulae 12 to 16, R3, R4, Ar4, Ar5, c, and d are as defined in formula 2.
Herein, “(C1-C30)alkyl” indicates a linear or branched alkyl having 1 to 30, preferably 1 to 20, and more preferably 1 to 10 carbon atoms, and includes methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, etc. “(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. Herein, “(C3-C30)cycloalkyl” indicates a mono- or polycyclic hydrocarbon having 3 to 30, preferabley 3 to 20, more preferably 3 to 7 ring backbone carbon atoms. The cycloalkyl includes cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, etc. Herein, “3 to 7-membered heterocycloalkyl” indicates a cycloalkyl having 3 to 7, preferably 5 to 7 ring backbone atoms including at least one heteroatom selected from B, N, O, S, Si, and P; preferably O, S, and N, and includes tetrahydrofuran, pyrrolidine, thiolan, tetrahydropyran, etc. Herein, “(C6-C30)aryl(ene)” indicates a monocyclic ring-type or fused ring-type radical derived from aromatic hydrocarbon having 6 to 30, preferabley 6 to 20 ring backbone carbon atoms wherein the (C6-C30)aryl(ene) may be partially saturated. The aryl includes phenyl, biphenyl, terphenyl, naphthyl, binaphthyl, phenylnaphthyl, naphthylphenyl, fluorenyl, phenylfluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, phenylphenanthrenyl, anthracenyl, indenyl, triphenylenyl, pyrenyl, tetracenyl, perylenyl, chrysenyl, naphthacenyl, fluoranthenyl, etc. Herein, “3 to 30-membered heteroaryl(ene)” indicates an aryl group having 3 to 30 ring backbone atoms including at least one, preferably 1 to 4, heteroatoms 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, tetrazolyl, furazanyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, etc., and a fused ring-type heteroaryl such as benzofuranyl, benzothiophenyl, isobenzofuranyl, dibenzofuranyl, dibenzothiophenyl, benzoimidazolyl, benzothiazolyl, benzoisothiazolyl, benzoisoxazolyl, benzoxazolyl, isoindolyl, indolyl, benzoindolyl, indazolyl, benzothiadiazolyl, quinolyl, isoquinolyl, cinnolinyl, quinazolinyl, quinoxalinyl, naphtyridyl, carbazolyl, phenoxazinyl, phenanthridinyl, benzodioxolyl, etc. Further, “halogen” includes F, Cl, Br, and I.
Furthermore, herein, “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 substituents of the substituted aryl(ene), the substituted heteroaryl(ene), the substituted alkyl, the substituted alkenyl, the substituted alkynyl, the substituted cycloalkyl, the substituted trialkylsilyl, the substituted triarylsilyl, the substituted dialkylarylsilyl, the substituted mono- or di-arylamino, the substituted phenyl, the substituted naphthyl, the substituted fluorenyl, the substituted dibenzothiophenyl, the substituted dibenzofuranyl, and the substituted, mono- or polycyclic, alicyclic or aromatic ring, or a combination of the alicyclic ring and the aromatic ring in L1, A, Ar1 to Ar5, and R1 to R14 of formulae 1 to 11 of the present disclosure, each independently, are at least one selected from the group consisting of deuterium, a halogen; a cyano; a carboxy; a nitro; a hydroxyl; a (C1-C30)alkyl; a halo(C1-C30)alkyl; a (C2-C30)alkenyl; a (C2-C30)alkynyl; a (C1-C30)alkoxy; a (C1-C30)alkylthio; a (C3-C30)cycloalkyl; a 3- to 7-membered heterocycloalkyl; a (C6-C30)aryloxy; a (C6-C30)arylthio; a 3- to 30-membered heteroaryl unsubstituted or substituted with a (C6-C30)aryl or di(C6-C30)arylamino; a (C6-C30)aryl unsubstituted or substituted with a cyano, a 3- to 30-membered heteroaryl or a tri(C6-C30)arylsilyl; a tri(C1-C30)alkylsilyl; a tri(C6-C30)arylsilyl; a di(C1-C30)alkyl(C6-C30)arylsilyl; a (C1-C30)alkyldi(C6-C30)arylsilyl; an amino; a mono- or di-(C1-C30)alkylamino; a mono- or di-(C6-C30)arylamino; a (C1-C30)alkyl(C6-C30)arylamino; a (C1-C30)alkylcarbonyl; a (C1-C30)alkoxycarbonyl; a (C6-C30)arylcarbonyl; a di(C6-C30)arylboronyl; a di(C1-C30)alkylboronyl; a (C1-C30)alkyl(C6-C30)arylboronyl; a (C6-C30)aryl(C1-C30)alkyl; and a (C1-C30)alkyl(C6-C30)aryl; and preferably, each independently, are at least one selected from the group consisting of a (C1-C20)alkyl, and an unsubstituted (C6-C25)aryl; more preferably, each independently, are at least one selected from the group consisting of a (C1-C10)alkyl, and an unsubstituted (C6-C18)aryl; and the substituent may include methyl, an unsubstituted naphthyl or an unsubstituted phenanthrenyl.
The first host compound of formula 1 of the present disclosure includes the following, but is not limited thereto:
Figure PCTKR2016012455-appb-I000015
Figure PCTKR2016012455-appb-I000016
Figure PCTKR2016012455-appb-I000017
Figure PCTKR2016012455-appb-I000018
Figure PCTKR2016012455-appb-I000019
Figure PCTKR2016012455-appb-I000020
Figure PCTKR2016012455-appb-I000021
Figure PCTKR2016012455-appb-I000022
Figure PCTKR2016012455-appb-I000023
Figure PCTKR2016012455-appb-I000024
Figure PCTKR2016012455-appb-I000025
Figure PCTKR2016012455-appb-I000026
Figure PCTKR2016012455-appb-I000027
Figure PCTKR2016012455-appb-I000028
Figure PCTKR2016012455-appb-I000029
Figure PCTKR2016012455-appb-I000030
The second host compound of formula 2 above of the present disclosure includes the following, but is not limited thereto:
Figure PCTKR2016012455-appb-I000031
Figure PCTKR2016012455-appb-I000032
Figure PCTKR2016012455-appb-I000033
Figure PCTKR2016012455-appb-I000034
Figure PCTKR2016012455-appb-I000035
Figure PCTKR2016012455-appb-I000036
Figure PCTKR2016012455-appb-I000037
Figure PCTKR2016012455-appb-I000038
Figure PCTKR2016012455-appb-I000039
Figure PCTKR2016012455-appb-I000040
Figure PCTKR2016012455-appb-I000041
Figure PCTKR2016012455-appb-I000042
Figure PCTKR2016012455-appb-I000043
Figure PCTKR2016012455-appb-I000044
Figure PCTKR2016012455-appb-I000045
Figure PCTKR2016012455-appb-I000046
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.
According to another embodiment of the present disclosure, a combination comprising the compound of formula 1 and the compound of formula 2 is provided. The combination above may be a combination that is comprised in a light-emitting layer of an organic electroluminescent device. In the combination of the present disclosure, the weight ratio in the light-emitting layer between the compound of formula 1 and the compound of formula 2 is in the range of 1:99 to 99:1, and preferably 30:70 to 70:30 in view of driving voltage, luminous efficiency, and lifespan.
The organic electroluminescent device of the present disclosure comprises an anode, a cathode, and one or more light-emitting layers disposed between the anode and cathode, wherein the light-emitting layers comprise a dopant and a host; the host comprises two or more host compounds; and a first host compound of the host compounds is represented by the formula 1 above; and a second host compound is represented by formula 2 above.
The light-emitting layer indicates a layer or plural layers consisting of two or more stacked layers, from which light is emitted. It is preferable that a doping amount of the dopant compound is less than 20 wt% based on the total amount of the host compound and the dopant compound. In the organic electroluminescent device of the present disclosure, the weight ratio in the light-emitting layer between the first host material and the second host material is in the range of 1:99 to 99:1, and preferably 30:70 to 70:30 in view of driving voltage, luminous efficiency, and lifespan.
The dopant for the organic electroluminescent device of the present disclosure is preferably one or more phosphorescent dopant compounds. The phosphorescent dopant compound for the organic electroluminescent device of the present disclosure is not limited, but may be preferably selected from metallated complex compounds of iridium (Ir), osmium (Os), copper (Cu) or platinum (Pt), more preferably selected from ortho-metallated complex compounds of iridium (Ir), osmium (Os), copper (Cu) or platinum (Pt), and even more preferably ortho-metallated iridium complex compounds.
The phosphorescent dopant may be preferably selected from the compound of the following formulae 101 to 103:
Figure PCTKR2016012455-appb-I000047
Figure PCTKR2016012455-appb-I000048
Figure PCTKR2016012455-appb-I000049
wherein L is selected from the following structures:
Figure PCTKR2016012455-appb-I000050
R100 represents hydrogen, or a substituted or unsubstituted (C1-C30)alkyl;
R101 to R109 and R111 to R123, each independently, represent hydrogen, deuterium, a halogen, a (C1-C30)alkyl substituted or unsubstituted with a halogen, a cyano, a substituted or unsubstituted (C1-C30)alkoxy, a substituted or unsubstituted (C3-C30)cycloalkyl, or a substituted or unsubstituted (C6-C30)aryl; R120 to R123, each independently, 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, or a combination of the alicyclic ring and the aromatic ring, for example, a quinoline; R124 to R127, each independently, represent hydrogen, deuterium, a halogen, a substituted or unsubstituted (C1-C30)alkyl, or a substituted or unsubstituted (C6-C30)aryl; when R124 to R127, each independently, are an aryl, R124 to R127, each independently, may be linked to an adjacent substituent(s) to form a substituted or unsubstituted 3 to 30-membered, mono- or polycyclic, alicyclic or (hetero)aromatic ring, or a combination of the alicyclic ring and the (hetero)aromatic ring, for example, a fluorene, a dibenzothiophene, a dibenzofuran; R201 to R211, each independently, represent hydrogen, deuterium, a halogen, or a (C1-C30)alkyl substituted or unsubstituted with a halogen; R208 to R211, each independently, may be linked to an adjacent substituent(s) to form a substituted or unsubstituted 3 to 30-membered, mono- or polycyclic, alicyclic, aromatic, or heteroaromatic ring, or a combination of the alicyclic ring, the aromatic ring, and the heteroaromatic ring, for example, a fluorene, a dibenzothiophene, a dibenzofuran; r and s, each independently, represent an integer of 1 to 3; when r or s is an integer of 2 or more, each of R100 may be the same or different; and e represents an integer of 1 to 3.
Specifically, the phosphorescent dopant includes the following:
Figure PCTKR2016012455-appb-I000051
Figure PCTKR2016012455-appb-I000052
Figure PCTKR2016012455-appb-I000053
Figure PCTKR2016012455-appb-I000054
Figure PCTKR2016012455-appb-I000055
Figure PCTKR2016012455-appb-I000056
Figure PCTKR2016012455-appb-I000057
Figure PCTKR2016012455-appb-I000058
Figure PCTKR2016012455-appb-I000059
Figure PCTKR2016012455-appb-I000060
Figure PCTKR2016012455-appb-I000061
Figure PCTKR2016012455-appb-I000062
Figure PCTKR2016012455-appb-I000063
Figure PCTKR2016012455-appb-I000064
Figure PCTKR2016012455-appb-I000065
Figure PCTKR2016012455-appb-I000066
Figure PCTKR2016012455-appb-I000067
Figure PCTKR2016012455-appb-I000068
Figure PCTKR2016012455-appb-I000069
Figure PCTKR2016012455-appb-I000070
Figure PCTKR2016012455-appb-I000071
Figure PCTKR2016012455-appb-I000072
Figure PCTKR2016012455-appb-I000073
Figure PCTKR2016012455-appb-I000074
Figure PCTKR2016012455-appb-I000075
The organic electroluminescent device of the present disclosure may further comprise at least one compound selected from the group consisting of arylamine-based compounds and styrylarylamine-based compounds in the organic layer.
In the organic electroluminescent device of the present disclosure, 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 4th period, transition metals of the 5th period, lanthanides and organic metals of the d-transition elements of the Periodic Table, or at least one complex compound comprising the metal.
In the organic electroluminescent device of the present disclosure, preferably, at least one layer (hereinafter, "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. Specifically, a chalcogenide (includes oxides) layer of silicon or aluminum is preferably placed on an anode surface of an electroluminescent medium layer, and a metal halide layer or a metal oxide layer is preferably placed on a cathode surface of an electroluminescent medium layer. Such a surface layer provides operation stability for the organic electroluminescent device. Preferably, the chalcogenide includes SiOX(1≤X≤2), AlOX(1≤X≤1.5), SiON, SiAlON, etc.; the metal halide includes LiF, MgF2, CaF2, a rare earth metal fluoride, etc.; and the metal oxide includes Cs2O, Li2O, MgO, SrO, BaO, CaO, etc.
In the organic electroluminescent device of the present disclosure, a hole injection layer, a hole transport layer, a hole auxiliary layer, an auxiliary light-emitting layer, or an electron blocking layer, or a combination thereof may be disposed between the anode and the light-emitting layer. The hole injection layer may be composed of two or more layers in order to lower an energy barrier for injecting holes from the anode to a hole transport layer or an electron blocking layer (or a voltage for injecting a hole). Each of the layers may comprise two or more compounds. The hole transport layer or electron blocking layer may be composed of two or more layers. Wherein the hole auxiliary layer or the auxiliary light-emitting layer is disposed between the hole transport layer and the light-emitting layer, and modulates hole mobility. The hole auxiliary layer or the auxiliary light-emitting layer has the effects to provide improved efficiency and lifespan of the organic electroluminescent device.
An electron buffering layer, a hole blocking layer, an electron transport layer, an electron injection layer, or a combination thereof may be disposed between the light-emitting layer and the cathode. The electron buffering layer may be composed of two or more layers in order to control the electron injection and improve characteristics of interface between the light-emitting layer and the electron injection layer. Each of the layers may comprise two or more compounds. The hole blocking layer or electron transport layer may be composed of two or more layers, and each of the layers may comprise two or more compounds.
In the organic electroluminescent device of the present disclosure, 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. In this case, 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. Furthermore, 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. Preferably, the oxidative dopant includes various Lewis acids and acceptor compounds, and 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.
In order to form each layer of the organic electroluminescent device of the present disclosure, any of dry film-forming methods such as vacuum evaporation, sputtering, plasma, and ion plating methods, or wet film-forming methods such as spin coating, dip coating, and flow coating methods can be used. A co-evaporation or a mixture-evaporation is used for forming a film of the first host material and a film of the second host material. The 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. Herein, 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.
When using a wet film-forming method, 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.
A display system or a lighting system using the organic electroluminescent device of the present disclosure can be produced.
Hereinafter, for a more in-depth understanding of the present disclosure, the luminescent properties of the organic electroluminescent device comprising the host compound of the present disclosure will be explained.
Hereinafter, the organic electroluminescent compound of the present disclosure, the preparation method and the physical properties of the compound, and the luminescent properties of the organic electroluminescent device comprising the compound will be explained in detail with reference to the following examples.
[Example 1] Preparation of compound H2-2
Figure PCTKR2016012455-appb-I000076
1) Preparation of compound 1-1
After introducing a compound 7H-benzo[c]carbazole (30 g, 138.1 mmol), 5-bromo-2-iodopyridine (58.8 g, 207.1 mmol), CuI (12.5 g, 65.4 mmol), K3PO4 (73 g, 345.2 mmol), ethylene diamine (8.3 g, 138.1 mmol), and toluene (600 mL) into a flask, the mixture was stirred under reflux at 120℃ for 4 hours. After completion of the reaction, the mixture was extracted with ethyl acetate and purified water, and the obtained organic layer was concentrated under reduced pressure. The organic layer was subjected to silica gel column chromatography (methylene chloride(MC):hexane(Hex)) to obtain compound 1-1 (16 g, yield: 31%).
2) Preparation of compound 1-2
After introducing compound 1-1 (16 g, 42.86 mmol), pinacolatodiboron (13.1 g, 51.44 mmol), PdCl2 (PPh3)2 (3 g, 4.3 mmol), potassium acetate (KOAc) (10.5 g, 107 mmol), and 1,4-dioxane (200 mL) into a flask, the mixture was stirred under reflux at 120℃ for 2 hours. After completion of the reaction, the mixture was extracted with ethyl acetate and purified water, and the obtained organic layer was dried under reduced pressure. The organic layer was subjected to silica gel column chromatography (MC:Hex) to obtain compound 1-2 (11 g, yield: 61%).
3) Preparation of compound H2-2
After introducing compound 1-2 (11 g, 26.17 mmol), 2-chloro-4-(naphthalen-2-yl)-6-phenyl-1,3,5-triazine (8.3 g, 26.17 mmol), Na2CO3 (6.9 g, 65.42 mmol), Pd(PPh3)4 (1.5 g, 1.3 mmol), tetrahydrofuran (THF) (100 mL), and purified water (30 mL) into a flask, the mixture was stirred under reflux at 120℃ for 4 hours. After completion of the reaction, the mixture was extracted with ethyl acetate and purified water, and the obtained organic layer was concentrated under reduced pressure. The organic layer was subjected to silica gel column chromatography (MC:Hex) to obtain compound H2-2 (6.54 g, yield: 43.1 %).
[Device Examples 1 to 4] OLED comprising a first host compound and a
second host compound of the present disclosure as a host
An OLED was produced using the organic electroluminescent compound of the present disclosure as follows. A transparent electrode indium tin oxide (ITO) thin film (10 Ω/sq) on a glass substrate for an OLED (Geomatec) was subjected to an ultrasonic washing with acetone, ethanol, and distilled water sequentially, and was then 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 said vacuum vapor depositing apparatus, and then the pressure in the chamber of said apparatus was controlled to 10-6 torr. Thereafter, an electric current was applied to the cell to evaporate the above introduced material, thereby forming a first hole injection layer having a thickness of 80 nm on the ITO substrate. HI-2 was then introduced into another cell of said vacuum vapor depositing apparatus, and evaporated by applying 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 one cell of the vacuum vapor depositing apparatus, and evaporated by applying 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-3 was introduced into another cell of the vacuum vapor depositing apparatus, and evaporated by applying electric current to the cell, thereby forming a second hole transport layer having a thickness of 60 nm on the first hole transport layer. After forming the hole injection layer and the hole transport layer, a light-emitting layer was deposited thereon as follows. A first host material and a second host material shown in Table 1 below were introduced, as host materials, into a cell of the vacuum vapor depositing apparatus, and compound D-71 was introduced, as a dopant, into another cell. The two host compounds were then evaporated at the same rate of 1:1, so that the dopant was deposited in a doping amount of 3 wt% based on the total amount of the host and dopant to form a light-emitting layer having a thickness of 40nm on the second hole transport layer. Compounds ET-1 and El-1 were then introduced into another two cells of the vacuum vapor depositing apparatus, respectively, and evaporated at the same rate of 1:1, thereby forming an electron transport layer having a thickness of 30nm on the light-emitting layer. After depositing compound El-1 as an electron injection layer having a thickness of 2nm on the electron transport layer, an Al cathode having a thickness of 80nm was then deposited by another vacuum vapor deposition apparatus on the electron injection layer to produce an OLED. Evaluation results of the devices produced in Device Examples 1 to 4 are shown in Table 1 below.
Figure PCTKR2016012455-appb-I000077
Figure PCTKR2016012455-appb-I000078
Figure PCTKR2016012455-appb-I000079
Figure PCTKR2016012455-appb-I000080
[Device Examples 5 to 8] OLED comprising a first host compound and a
second host compound of the present disclosure as a host
In Device Examples 5 to 8, OLEDs were produced in the same manner as in Device Examples 1 to 4, except that a first hole injection layer having a thickness of 90nm was formed, the doping amount of the dopant was 2 wt%, an electron transport layer having a thickness of 35 nm was deposited, and the first host was changed as shown in Table 2 below. Evaluation results of the devices produced in Device Examples 5 to 8 are shown in Table 2 below.
Figure PCTKR2016012455-appb-I000081
Figure PCTKR2016012455-appb-I000082
[Comparative Device Example 1] OLED comprising a conventional organic
electroluminescent compound
An OLED was produced in the same manner as in Device Examples 1 to 4, except that the first host shown in Table 3 below was employed as a host for a light-emitting layer and the second host was not employed.
Figure PCTKR2016012455-appb-I000083
[Comparative Device Example 2] OLED comprising a conventional organic
electroluminescent compound
An OLED was produced in the same manner as in Device Examples 1 to 4, except that the second host shown in Table 4 below was employed as a host for a light-emitting layer and the first host was not employed.
Figure PCTKR2016012455-appb-I000084
[Comparative Device Example 3] OLED comprising a conventional organic
electroluminescent compound
An OLED was produced in the same manner as in Device Examples 1 to 4, except that the first host and the second host shown in Table 5 below were employed as a host for a light-emitting layer.
Figure PCTKR2016012455-appb-I000085
Figure PCTKR2016012455-appb-I000086
By using a specific combination of two or more host compounds according to the present disclosure, the organic electroluminescent device of the present disclosure has luminous efficiency at least equivalent to or higher than conventional devices and has lifespan longer than conventional devices.

Claims (8)

  1. A host material that comprises one or more first host compounds and one or more second host compounds wherein the first host compound is represented by the following formula 1 and the second host compound is represented by the following formula 2:
    Figure PCTKR2016012455-appb-I000087
    wherein
    L1 represents a single bond or a substituted or unsubstituted (C6-C30)arylene,
    A represents hydrogen, a substituted or unsubstituted phenyl, a substituted or unsubstituted naphthyl, a substituted or unsubstituted fluorenyl, a substituted or unsubstituted dibenzothiophenyl, or a substituted or unsubstituted dibenzofuranyl,
    Ar1, Ar2, and Ar3, each independently, represent a substituted or unsubstituted (C6-C30)aryl(ene), or a substituted or unsubstituted 3- to 30-membered heteroaryl(ene); or Ar2 and Ar3 may be linked to form a substituted or unsubstituted 3 to 30-membered, mono- or polycyclic, alicyclic or aromatic ring, or a combination of the alicyclic ring and the aromatic ring, whose carbon atom(s) may be replaced with at least one heteroatom selected from the group consisting of nitrogen, oxygen, and sulfur,
    R1 represents 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-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, or a substituted or unsubstituted mono- or di-(C6-C30)arylamino; or R1 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, or a combination of the alicyclic ring and the aromatic ring,
    wherein the heteroaryl(ene) contains one or more heteroatoms selected from the group consisting of B, N, O, S, Si, and P,
    a represents an integer of 0 to 4,
    and when a is an integer of 2 or more, each of R1 may be the same or different;
    Figure PCTKR2016012455-appb-I000088
    wherein
    Ar4 and Ar5, each independently, represent a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (C3-C30)cycloalkyl, or a substituted or unsubstituted 3- to 30-membered heteroaryl,
    R3 and R4, each independently, represent 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-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, or a substituted or unsubstituted mono- or di-(C6-C30)arylamino,
    wherein the heteroaryl contains one or more heteroatoms selected from the group consisting of B, N, O, S, Si, and P, and
    c represents an integer of 0 to 4; d represents an integer of 0 to 6; and when c or d is an integer of 2 or more, each of R3 or R4 may be the same or different.
  2. The host material according to claim 1, wherein formula 1 is represented by any one of the following formulae 3 to 7:
    Figure PCTKR2016012455-appb-I000089
    Figure PCTKR2016012455-appb-I000090
    Figure PCTKR2016012455-appb-I000091
    Figure PCTKR2016012455-appb-I000092
    Figure PCTKR2016012455-appb-I000093
    wherein
    Ar1, Ar2, and Ar3, each independently, represent a substituted or unsubstituted (C6-C30)aryl(ene), or a substituted or unsubstituted 3 to 30-membered heteroaryl(ene);
    X represents S, O or CR7R8;
    R2 and R5 to R8, each independently, represent 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-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, or a substituted or unsubstituted mono- or di-(C6-C30)arylamino; or R2 and R5 to R8, each independently, are linked to an adjacent substituent(s) to form a substituted or unsubstituted 3 to 30-membered, mono- or polycyclic, alicyclic or aromatic ring, or a combination of the alicyclic ring and the aromatic ring, whose carbon atom(s) may be replaced with at least one heteroatom selected from the group consisting of nitrogen, oxygen, and sulfur;
    b and f, each independently, represent an integer of 0 to 4, and e represents an integer of 0 to 2; when each of b or f represents an integer of 2 or more, or when e represents an integer of 2, each of R2, R5, or R6 may be the same or different; and
    L1, R1, and a are as defined in claim 1.
  3. The host material according to claim 2, wherein formula 3 is represented by any one of the following formulae 8 to 10:
    Figure PCTKR2016012455-appb-I000094
    Figure PCTKR2016012455-appb-I000095
    Figure PCTKR2016012455-appb-I000096
    wherein
    R9 to R12, each independently, represent 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-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, or a substituted or unsubstituted mono- or di-(C6-C30)arylamino; or R9 to R12, each independently, 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, or a combination of the alicyclic ring and the aromatic ring, whose carbon atom(s) may be replaced with at least one heteroatom selected from the group consisting of nitrogen, oxygen, and sulfur;
    the heteroaryl contains one or more heteroatoms selected from the group consisting of B, N, O, S, Si, and P;
    g and h, each independently, represent an integer of 0 to 6; i represents an integer of 0 to 4; j represents an integer of 0 to 7; when each of g, h, i or j represents an integer of 2 or more, each of R9, R10, R11 or R12 may be the same or different; and
    L1, R1, R2, Ar1, Ar2, Ar3, a, and b are as defined in claim 2.
  4. The host material according to claim 2, wherein formula 4 is represented by the following formula 11:
    Figure PCTKR2016012455-appb-I000097
    wherein
    R13 and R14, each independently, represent 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-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, or a substituted or unsubstituted mono- or di-(C6-C30)arylamino; or R13 and R14, each independently, 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, or a combination of the alicyclic ring and the aromatic ring, whose carbon atom(s) may be replaced with at least one heteroatom selected from the group consisting of nitrogen, oxygen, and sulfur;
    the heteroaryl contains one or more heteroatoms selected from the group consisting of B, N, O, S, Si, and P;
    k represents an integer of 0 to 4, and m represents an integer of 0 to 7; when each of k or m represents an integer of 2 or more, each of R13 or R14 may be the same or different; and
    L1, R1, R5, R6, Ar1, Ar3, a, e, and f are as defined in claim 2.
  5. The host material according to claim 1, wherein formula 2 is represented by any one of the following formulae 12 to 16:
    Figure PCTKR2016012455-appb-I000098
    Figure PCTKR2016012455-appb-I000099
    Figure PCTKR2016012455-appb-I000100
    wherein Ar4, Ar5, R3, R4, c, and d are as defined in claim 1.
  6. The host material according to claim 1, wherein the first host compound of formula 1 is selected from the group consisting of:
    Figure PCTKR2016012455-appb-I000101
    Figure PCTKR2016012455-appb-I000102
    Figure PCTKR2016012455-appb-I000103
    Figure PCTKR2016012455-appb-I000104
    Figure PCTKR2016012455-appb-I000105
    Figure PCTKR2016012455-appb-I000106
    Figure PCTKR2016012455-appb-I000107
    Figure PCTKR2016012455-appb-I000108
    Figure PCTKR2016012455-appb-I000109
    Figure PCTKR2016012455-appb-I000110
    Figure PCTKR2016012455-appb-I000111
    Figure PCTKR2016012455-appb-I000112
    Figure PCTKR2016012455-appb-I000113
    Figure PCTKR2016012455-appb-I000114
    Figure PCTKR2016012455-appb-I000115
    Figure PCTKR2016012455-appb-I000116
  7. The host material according to claim 1, wherein the second host compound of formula 2 is selected from the group consisting of:
    Figure PCTKR2016012455-appb-I000117
    Figure PCTKR2016012455-appb-I000118
    Figure PCTKR2016012455-appb-I000119
    Figure PCTKR2016012455-appb-I000120
    Figure PCTKR2016012455-appb-I000121
    Figure PCTKR2016012455-appb-I000122
    Figure PCTKR2016012455-appb-I000123
    Figure PCTKR2016012455-appb-I000124
    Figure PCTKR2016012455-appb-I000125
    Figure PCTKR2016012455-appb-I000126
    Figure PCTKR2016012455-appb-I000127
    Figure PCTKR2016012455-appb-I000128
    Figure PCTKR2016012455-appb-I000129
    Figure PCTKR2016012455-appb-I000130
    Figure PCTKR2016012455-appb-I000131
    Figure PCTKR2016012455-appb-I000132
  8. An organic electroluminescent device comprising an anode, a cathode, and at least one light-emitting layer disposed between the anode and cathode, wherein the light-emitting layer comprises a host and a dopant, and the host comprises the host material according to claim 1.
PCT/KR2016/012455 2015-11-17 2016-11-01 A plurality of host materials and organic electroluminescent device comprising the same WO2017086629A1 (en)

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CN108780853A (en) * 2016-04-18 2018-11-09 罗门哈斯电子材料韩国有限公司 A variety of material of main parts and organic electroluminescence device comprising it
EP3446345A4 (en) * 2016-04-18 2020-01-01 Rohm And Haas Electronic Materials Korea Ltd. A plurality of host materials and organic electroluminescent device comprising the same
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