WO2018070821A1 - Dispositif électroluminescent organique - Google Patents

Dispositif électroluminescent organique Download PDF

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Publication number
WO2018070821A1
WO2018070821A1 PCT/KR2017/011300 KR2017011300W WO2018070821A1 WO 2018070821 A1 WO2018070821 A1 WO 2018070821A1 KR 2017011300 W KR2017011300 W KR 2017011300W WO 2018070821 A1 WO2018070821 A1 WO 2018070821A1
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Prior art keywords
substituted
unsubstituted
alkyl
layer
organic electroluminescence
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PCT/KR2017/011300
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English (en)
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Dong-Hyung Lee
Tae-Jin Lee
Bitnari Kim
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Rohm And Haas Electronic Materials Korea Ltd.
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Priority claimed from KR1020170129677A external-priority patent/KR102520279B1/ko
Application filed by Rohm And Haas Electronic Materials Korea Ltd. filed Critical Rohm And Haas Electronic Materials Korea Ltd.
Priority to US16/335,839 priority Critical patent/US20200028082A1/en
Priority to CN201780062440.1A priority patent/CN109804045A/zh
Publication of WO2018070821A1 publication Critical patent/WO2018070821A1/fr

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    • H—ELECTRICITY
    • H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
    • H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
    • H05B33/00—Electroluminescent light sources
    • H05B33/12—Light sources with substantially two-dimensional radiating surfaces
    • H05B33/20—Light sources with substantially two-dimensional radiating surfaces characterised by the chemical or physical composition or the arrangement of the material in which the electroluminescent material is embedded
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
    • H10K85/633—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C211/00—Compounds containing amino groups bound to a carbon skeleton
    • C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
    • C07C211/57—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton
    • C07C211/61—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton with at least one of the condensed ring systems formed by three or more rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2603/00—Systems containing at least three condensed rings
    • C07C2603/02—Ortho- or ortho- and peri-condensed systems
    • C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
    • C07C2603/06—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members
    • C07C2603/10—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings
    • C07C2603/12—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings only one five-membered ring
    • C07C2603/18—Fluorenes; Hydrogenated fluorenes
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2603/00—Systems containing at least three condensed rings
    • C07C2603/93—Spiro compounds
    • C07C2603/94—Spiro compounds containing "free" spiro atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/14—Carrier transporting layers
    • H10K50/15—Hole transporting layers

Definitions

  • the present disclosure relates to an organic electroluminescence device.
  • An electroluminescence device is a self-light-emitting device with the advantages of providing a wider viewing angle, a greater contrast ratio, and a faster response time.
  • the first organic EL device was developed by Eastman Kodak, 1987, by using a low-molecular aromatic diamine and an aluminum complex as materials for forming a light-emitting layer ( see Appl. Phys. Lett. 51, 913, 1987).
  • An organic electroluminescence device changes electric energy into light by the injection of a charge into an organic light-emitting material, and commonly comprises an anode, a cathode, and an intermediate layer formed between the two electrodes.
  • the intermediate layer of the organic electroluminescence device may be composed of a hole injection layer, a hole transport layer, an electron blocking layer, a light-emitting layer, an electron buffer layer, a hole blocking layer, an electron transport layer, an electron injection layer, etc.
  • the materials used in the intermediate layer can be classified into a hole injection material, a hole transport material, an electron blocking material, a light-emitting material, an electron buffer material, a hole blocking material, an electron transport material, an electron injection material, etc., depending on functions.
  • the organic electroluminescence device holes from an anode and electrons from a cathode are injected into a light-emitting layer by electric voltage, and an exciton having high energy is produced by the recombination of the holes and electrons.
  • the organic light-emitting compound moves into an excited state by the energy and emits light from energy when the organic light-emitting compound returns to the ground state from the excited state.
  • the selection of a compound contained in the hole transport layer, etc. is recognized as a means for improving device characteristics such as hole transport efficiency to the light-emitting layer, luminous efficiency, and lifespan.
  • the light-emitting material of the organic electroluminescence device is the most important factor for determining the luminous efficiency of the device so that the light-emitting material should have high quantum efficiency and high electron and hole mobility, and the formed light-emitting layer should be uniform and stable.
  • Such a light-emitting material is divided into a blue, green or red light-emitting material depending on a luminescent color, and further there is a yellow or orange light-emitting material.
  • the light-emitting material can be used by mixing a host and dopant in order to improve color purity, luminous efficiency, and stability.
  • a device having excellent EL characteristics is a structure including a light-emitting layer made by doping a dopant with a host.
  • the selection thereof is important since the host material has a significant effect on the efficiency and lifespan of the light-emitting device.
  • Japanese Patent Publication No. 3670707 and Korean Laid-Open Patent Publication No. 2013-0099098 disclose spirobifluorene substituted with a diarylamine as an organic electroluminescence compound including a hole transport material.
  • Korean Patent Publication No. 1477614 discloses, as a host material, a compound in which a benzene ring is fused to one of two carbazoles in a biscarbazole structure and a heteroaryl containing nitrogen is bonded to one of two nitrogen atoms.
  • an organic electroluminescence device using spirobifluorene substituted with a diarylamine is used as a hole transport material and a compound in which a benzene ring is fused to one of two carbazoles in a biscarbazole structure and a heteroaryl containing nitrogen is bonded to one of two nitrogen atoms as a host material.
  • the objective of the present disclosure is to provide an organic electroluminescence device having long lifespan by comprising a specific combination of a hole transport material and a host material.
  • an organic electroluminescence device comprising a first electrode; a second electrode facing the first electrode; an intermediate layer between the first electrode and the second electrode; wherein the intermediate layer comprises at least one layer of a hole transporting band and at least one layer of a light-emitting layer; wherein at least one layer of the hole transporting band comprises a compound represented by the following Formula 1; wherein at least one layer of the light-emitting layer comprises at least one dopant compound and at least one host compound; and the at least one host compound comprises a compound represented by the following Formula 2:
  • L, L 1 and L 2 each independently represent a single bond or a substituted or unsubstituted (C6-C30)arylene;
  • Ar 1 to Ar 4 each independently represent a substituted or unsubstituted (C6-C30)aryl or a substituted or unsubstituted (3- to 30-membered)heteroaryl;
  • R 1 to R 5 each independently represent hydrogen, deuterium, halogen, 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 unsubstit
  • n and n each independently represent an integer of 1 or 2;
  • p, q, r, and t each independently represent an integer of 1 to 4.
  • s represents an integer of 1 to 6;
  • each of [L-(NAr 1 Ar 2 ) n ], each of (NAr 1 Ar 2 ), each of R 1 , each of R 2 , each of R 3 , each of R 4 or each of R 5 may be the same or different;
  • the heteroaryl contains at least one heteroatom selected from B, N, O, S, Si, and P.
  • the present disclosure provides an organic electroluminescence device having long lifespan, and a display system or a lighting system can be produced by using the device.
  • the organic electroluminescence device of the present disclousre will be described in more detail as follows.
  • (C1-C30)alkyl is meant to be a linear or branched alkyl having 1 to 30 carbon atoms constituting the chain, in which the number of carbon atoms is preferably 1 to 10, more preferably 1 to 6, and includes methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, etc.
  • (C2-C30)alkenyl is meant to be a linear or branched alkenyl having 2 to 30 carbon atoms constituting the chain, in which the number of carbon atoms is preferably 2 to 20, more preferably 2 to 10, and includes vinyl, 1-propenyl, 2-propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 2-methylbut-2-enyl, etc.
  • (C2-C30)alkynyl is a linear or branched alkynyl having 2 to 30 carbon atoms constituting the chain, in which the number of carbon atoms is preferably 2 to 20, more preferably 2 to 10, and includes ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methylpent-2-ynyl, etc.
  • (C3-C30)cycloalkyl is a mono- or polycyclic hydrocarbon having 3 to 30 ring backbone carbon atoms, in which the number of carbon atoms is preferably 3 to 20, more preferably 3 to 7, and includes cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, etc.
  • “(3- to 7-membered)heterocycloalkyl” is a cycloalkyl having 3 to 7 ring backbone atoms and at least one heteroatom selected from the group consisting of B, N, O, S, Si, and P, preferably O, S, and N, and includes tetrahydrofuran, pyrrolidine, thiolan, tetrahydropyran, etc.
  • (C6-C30)aryl(ene) is a monocyclic or fused ring radical derived from an aromatic hydrocarbon having 6 to 30 ring backbone carbon atoms and may be partially saturated, in which the number of ring backbone carbon atoms is preferably 6 to 20, more preferably 6 to 15, and 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)” is an aryl group having at least one, preferably 1 to 4 heteroatoms selected from the group consisting of B, N, O, S, Si, and P, and 3 to 30 ring backbone atoms, in which the number of ring backbone atoms is preferably 3 to 20, more preferably 5 to 15; is a monocyclic ring, or a fused ring condensed with at least one benzene ring; may be partially saturated; may be one formed by linking at least one heteroaryl or aryl group to a heteroaryl group via a single bond(s); and includes a monocyclic ring-type heteroaryl including furyl, thiophenyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl,
  • “(5- to 30-membered)heteroaryl(ene) containing nitrogen” is a heteroaryl group having at least one, preferably 1 to 4 heteroatoms selected from the group consisting of B, N, O, S, Si and P, in particular at least one N, and 5 to 30 ring backbone atoms, in which the number of ring backbone atoms is preferably 5 to 20, more preferably 5 to 15; is a monocyclic ring, or a fused ring condensed with at least one benzene ring; may be partially saturated; may be one formed by linking at least one heteroaryl or aryl group to a heteroaryl group via a single bond(s); and includes a monocyclic ring-type heteroaryl including pyrrolyl, imidazolyl, pyrazolyl, triazinyl, tetrazinyl, triazolyl, tetrazolyl, pyridyl, pyrazinyl, pyrimidinyl,
  • substituted in the expression “substituted or unsubstituted” means that a hydrogen atom is replaced with another atom or functional group (i.e., a substituent) in a certain functional group.
  • Formula 1 may be represented by any one of the following Formulae 3 to 5:
  • L a and L b are as defined in L;
  • Ar 1a and Ar 1b are as defined in Ar 1 ;
  • Ar 2a and Ar 2b are as defined in Ar 2 ;
  • Ar 1 , Ar 2 , Ar 1a , Ar 2a , Ar 1b , and Ar 2b each independently may be represented by any one of the following Formulae R-1 to R-9.
  • Formula 2 may be represented by the following Formula 6 or 7.
  • HAr represents a substituted or unsubstituted (5- to 30-membered)heteroaryl containing nitrogen;
  • L 1 and L 2 each independently represent a single bond or a substituted or unsubstituted (C6-C30)arylene;
  • R 6 and R 7 each independently represent a substituted or unsubstituted (C6-C30)aryl.
  • L represents a single bond, or a substituted or unsubstituted (C6-C30)arylene, preferably a single bond, or a substituted or unsubstituted (C6-C12)arylene, more preferably, a single bond, or unsubstituted (C6-C12)arylene.
  • L may represent a single bond or phenylene.
  • Ar 1 and Ar 2 each independently represent a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (3- to 30-membered) heteroaryl, preferably a substituted or unsubstituted (C6-C20)aryl, more preferably (C1-C6)alkyl- or (C6-C12)aryl-substituted or unsubstituted (C6-C20)aryl.
  • Ar 1 and Ar 2 each independently may represent phenyl, biphenyl, terphenyl, naphthylphenyl, phenylnaphthyl, dimethylfluorenyl, or dimethylbenzofluorenyl.
  • R 1 to R 3 each independently represent hydrogen, deuterium, halogen, 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 unsubstit
  • L 1 and L 2 each independently represent a single bond, or a substituted or unsubstituted (C6-C30)arylene, preferably a single bond or a substituted or unsubstituted (C6-C12)arylene, more preferably, a single bond or an unsubstituted (C6-C12)arylene.
  • L 1 and L 2 each independently may represent a single bond, phenylene or naphthylene.
  • Ar 3 and Ar 4 each independently represent a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (3- to 30-membered)heteroaryl, preferably, a substituted or unsubstituted (C6-C20)aryl, or a substituted or unsubstituted (5- to 30-membered)heteroaryl containing nitrogen, more preferably, (C1-C6)alkyl- or (C6-C12)aryl-substituted or unsubstituted (C6-C20)aryl; (C6-C20)aryl, (C1-C6)alkyl(C6-C20)aryl, or (5- to 15-membered)heteroaryl containing nitrogen substituted with (C6-C12)aryl-substituted or unsubstituted (5- to 20-membered)heteroaryl.
  • Ar 3 and Ar 4 each independently may represent phenyl, biphenyl, naphthylphenyl, phenylnaphthyl, terphenyl, anthracenyl, phenanthrenyl, di(C1-C6)alkylfluorenyl, quinazolinyl substituted with phenyl, quinazolinyl substituted with di(C1-C6)alkylphenyl, quinazolinyl substituted with naphthylphenyl, quinazolinyl substituted with phenylnaphthyl, quinazolinyl substituted with terphenyl, quinazolinyl substituted with anthracenyl, quinazolinyl substituted with phenanthrenyl, quinazolinyl substituted with biphenyl, quinazolinyl substituted with di(C1-C6)alkylfluorenyl, quinazolin
  • R 4 and R 5 each independently represent hydrogen, deuterium, halogen, 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 unsubstit
  • the compound represented by Formula 1 may be illustrated by the following compounds, but is not limited thereto.
  • the compound represented by Formula 2 may be illustrated by the following compounds, but is not limited thereto.
  • An organic electroluminescence device comprises a first electrode; a second electrode facing the first electrode; an intermediate layer between the first electrode and the second electrode; wherein the intermediate layer comprises at least one layer of hole transporting band and at least one layer of light-emitting layer; wherein at least one layer of the hole transporting band comprises a compound represented by Formula 1; wherein at least one layer of the light-emitting layer comprises at least one dopant compound and at least one host compound; and at least one host compound comprises a compound represented by Formula 2.
  • the intermediate layer may further include one or more layers selected from a light-emitting auxiliary layer, an electron transport layer, an electron buffer layer, an electron injection layer, an interlayer, and a hole blocking layer.
  • the hole transporting band of the present disclosure may be composed of one or more layers from the group consisting of a hole transport layer, a hole injection layer, an electron blocking layer and a hole auxiliary layer, and each of the layers may be formed of one or more layers.
  • the hole transporting band includes a hole transport layer.
  • the hole transporting band may include a hole transport layer, and may further include at least one layer of a hole injection layer, an electron blocking layer, and a hole auxiliary layer.
  • the hole auxiliary layer or the light-emitting auxiliary layer is disposed between the hole transport layer and the light-emitting layer and controls transport speed of the hole.
  • the hole auxiliary layer or the light-emitting auxiliary layer provides effects of improving the efficiency and lifespan of the organic electroluminescence device.
  • the hole transport layer may be a single layer, and may include a hole transport material comprising a compound represented by Formula 1 of the present disclosrue.
  • the hole transporting band includes a hole transport layer, and the hole transport layer may be composed of two or more layers, wherein at least one of a plurality of layers may include a hole transport material comprising a compound represented by Formula 1 of the present disclosure.
  • the hole transport layer comprising a compound of Formula 1 or other layers may comprise all compounds used in conventional hole transport material, e.g., may comprise a compound represented by the following Formula 10:
  • L 11 represents a single bond, a substituted or unsubstituted (C6-C30)arylene, or a substituted or unsubstituted (5- to 30-membered)heteroarylene;
  • Ar 11 and Ar 12 each independently represent substituted or unsubstituted (C6-C30)aryl or a substituted or unsubstituted (5- to 30-membered)heteroaryl, or Ar 11 and L 11 may form (5- to 30-membered)heteroaryl containing nitrogen together with bonded nitrogen;
  • R 11 to R 13 each independently represent hydrogen, deuterium, halogen, cyano, carboxyl, nitro, hydroxyl, 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 (C1-C30)alkoxy, a substituted or unsubstituted (C3-C30)cycloalkyl, a substituted or unsubstituted (C3-C30)cycloalkenyl, a substituted or unsubstituted (3- to 7-membered)heterocycloalkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (5- to 30-membered)heteroaryl, -NR 41 R 42 ,
  • R 41 to R 50 each independently represent hydrogen, deuterium, halogen, cyano, carboxyl, nitro, hydroxyl, 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 (C1-C30)alkoxy, a substituted or unsubstituted (C3-C30)cycloalkyl, a substituted or unsubstituted (C3-C30)cycloalkenyl, a substituted or unsubstituted (3- to 7-membered)heterocycloalkyl, a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (5- to 30-membered)heteroaryl, or may be linked to an adjacent
  • x represents an integer of 1 to 4, where if x represents an integer of 2 or more, each of R 11 may be the same or different;
  • y represents an integer of 1 to 3, where if y represents an integer of 2 or more, each of R 12 may be the same or different;
  • the heteroaryl(ene) contains at least one heteroatom selected from B, N, O, S, Si and P;
  • the heterocycloalkyl contains at least one heteroatom selected from O, S, and N.
  • the compound of the present disclosure represented by Formula 2 may be comprised in the light-emitting layer.
  • the organic electroluminescence compound of Formula 2 may be comprised as a host material.
  • the light-emitting layer may further comprise at least one dopant.
  • the compound of the present disclosure represented by Formula 2 may be used as a co-host material. That is, the light-emitting layer may comprise the organic electroluminescence compound of Formula 2 of the present disclosure (a first host material) and may further comprise a compound other than the first host material as a second host material.
  • the weight ratio of the first host material to the second host material is in the range of 1:99 to 99:1.
  • the second host material may be preferably selected from the group consisting of the compounds represented by the following Formulae 11 to 16:
  • A represents -O- or -S-
  • R 21 to R 24 each independently, represent hydrogen, deuterium, halogen, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (5- to 30-membered)heteroaryl, or -SiR 25 R 26 R 27 , in which R 25 to R 27 , each independently, represent a substituted or unsubstituted (C1-C30)alkyl or a substituted or unsubstituted (C6-C30)aryl;
  • L 4 represents a single bond, a substituted or unsubstituted (C6-C30)arylene, or a substituted or unsubstituted (5- to 30-membered)heteroarylene;
  • M represents a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (5- to 30-
  • Y 3 to Y 5 each independently, represent CR 34 or N;
  • R 34 represents hydrogen, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (5- to 30-membered)heteroaryl;
  • B 1 and B 2 each independently, represent hydrogen, a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (5- to 30-membered)heteroaryl;
  • B 3 represents a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (5- to 30-membered)heteroaryl;
  • L 5 represents a single bond, a substituted or unsubstituted (C6-C30)arylene, or a substituted or unsubstituted (5- to 30-membered)heteroarylene.
  • the preferred examples of the second host material are as follows.
  • TPS represents a triphenylsilyl group.
  • the dopant comprised in the organic electroluminescence device of the present disclosure is preferably at least one phosphorescent dopant.
  • the phosphorescent dopant material applied to the organic electroluminescence device of the present disclosure is not particulary limited, but may be preferably selected from the metallated complex compounds of iridium (Ir), osmium (Os), copper (Cu), and platinum (Pt), more preferably selected from ortho-metallated complex compounds of iridium (Ir), osmium (Os), copper (Cu), and platinum (Pt), and even more preferably ortho-metallated iridium complex compounds.
  • the dopant comprised in the organic electroluminescence device of the present disclosure may comprise the compound represented by the following Formula 101, but is not limited thereto:
  • L is selected from the following structures 1 and 2:
  • R 100 to R 103 each independently represent hydrogen, deuterium, halogen, a halogen-substituted or unsubstituted (C1-C30)alkyl , a substituted or unsubstituted (C3-C30)cycloalkyl, a substituted or unsubstituted (C6-C30)aryl, cyano, a substituted or unsubstituted (3- to 30-membered)heteroaryl, or a substituted or unsubstituted (C1-C30)alkoxy; or R 100 to R 103 may be linked to adjacent substituents to form a substituted or unsubstituted fused ring along with pyridine, e.g., a substituted or unsubstituted quinoline, a substituted or unsubstituted isoquinoline, a substituted or unsubstituted benzofuropyridine, a substituted or unsubstituted benzothien
  • R 104 to R 107 each independently represent hydrogen, deuterium, halogen, a halogen-substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C3-C30)cycloalkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (3- to 30-membered)heteroaryl, cyano, or a substituted or unsubstituted (C1-C30)alkoxy; or R 104 to R 107 may be linked to adjacent substituents to form a substituted or unsubstituted fused ring along with benzene, e.g., a substituted or unsubstituted naphthyl, a substituted or unsubstituted fluorene, a substituted or unsubstituted dibenzothiophene, a substituted or unsubstitute
  • R 201 to R 211 each independently represent hydrogen, deuterium, halogen, a halogen-substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C3-C30)cycloalkyl, a substituted or unsubstituted (C6-C30)aryl; or R 201 to R 211 may be linked to adjacent substituents to form a substituted or unsubstituted fused ring;
  • n an integer of 1 to 3.
  • the specific examples of the dopant compound include the following, but are not limited thereto.
  • the organic electroluminescence device of the present disclosure may further comprise at least one compound selected from the group consisting of an arylamine compound and a styrylarylamine compound in the intermediate layer.
  • the intermediate 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 such a metal.
  • a surface layer preferably, at least one layer selected from a chalcogenide layer, a metal halide layer, and a metal oxide layer (hereinafter, "a surface layer”) may be placed on an inner surface(s) of one or both electrode(s).
  • a chalcogenide (including oxides) layer of silicon or aluminum is preferably placed on an anode surface of an electroluminescence medium layer
  • a metal halide layer or a metal oxide layer is preferably placed on a cathode surface of an electroluminescence medium layer.
  • the operation stability for the organic electroluminescence device may be obtained by the surface 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.
  • the first electrode may be an anode, and a hole transporting band may be disposed between the anode and the light-emitting layer and may include a hole transport layer.
  • a hole injection layer In addition to the hole transport layer, a hole injection layer, an electron blocking layer, or a combination of a hole injection layer and an electron blocking layer may be used.
  • the hole injection layer may be formed of a plurality of layers for the purpose of lowering the hole injection barrier (or hole injection voltage) from the anode to the hole transport layer or the electron blocking layer, and each layer may use two compounds at the same time.
  • the electron blocking layer may also be used as a plurality of layers.
  • the second electrode may be a cathode, and a layer selected from an electron buffer layer, a hole blocking layer, an electron transport layer, or an electron injection layer or a combination thereof may be used between the light-emitting layer and the cathode.
  • the electron buffer layer may be formed of a plurality of layers for the purpose of controlling electron injection and improving interfacial characteristics between the light-emitting layer and the electron injection layer, and each layer may use two compounds at the same time.
  • a plurality of layers may also be used as the hole blocking layer or the electron transporting layer, and a plurality of compounds may be used in each layer.
  • 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 electroluminescence 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 electroluminescence 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 organic electroluminescence device having two or more light-emitting layers and emitting white light.
  • dry film-forming methods such as vacuum evaporation, sputtering, plasma, ion plating methods, etc.
  • wet film-forming methods such as ink jet printing, nozzle printing, slot coating, spin coating, dip coating, flow coating methods, etc.
  • 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.
  • the organic electroluminescence device of the present disclosure can be used for the manufacture of a display device or a lighting device.
  • An OLED device including a combination of a hole transport material and a host compound of the present disclosure was prepared.
  • a transparent electrode indium tin oxide (ITO) thin film (10 ⁇ /sq) on a glass substrate for an OLED device (GEOMATEC CO., LTD., Japan) was subjected to an ultrasonic washing with acetone, ethanol, and distilled water, sequentially, and then was stored in isopropanol.
  • the ITO substrate was then mounted on a substrate holder of a vacuum vapor deposition apparatus.
  • HI-1 was introduced into a cell of the vacuum vapor deposition apparatus, and then the pressure in the chamber of the apparatus was controlled to 10 -6 torr by air exhaustion.
  • HI-2 was introduced into another cell of the vacuum vapor deposition apparatus, and was evaporated by applying an electric current to the cell, thereby forming a second hole injection layer having a thickness of 5 nm on the first hole injection layer.
  • HT-1 was then introduced into another cell of the vacuum vapor deposition apparatus, and was evaporated by applying an electric current to the cell, thereby forming a first hole transport layer having a thickness of 10 nm on the second hole injection layer.
  • C-10 was then introduced into another cell of the vacuum vapor deposition apparatus, and was evaporated by applying an electric current to the cell, thereby forming a second hole transport layer having a thickness of 60 nm on the first hole transport layer.
  • a light-emitting layer was formed thereon as follows: H-17 was introduced into one cell of the vacuum vapor depositing apparatus as a host, and D-39 was introduced into another cell as a dopant. The dopant was deposited in a doping amount of 2 wt% based on the total amount of the host and dopant by evaporating the two materials at different rates to form a light-emitting layer having a thickness of 40 nm on the second hole transport layer.
  • ET-1 and EI-1 were then introduced into the other two cells, and were respectively evaporated at a rate of 1:1 to form an electron transport layer having a thickness of 35 nm on the light-emitting layer.
  • EI-1 As an electron injection layer having a thickness of 2 nm on the electron transport layer, an Al cathode having a thickness of 80 nm was deposited on the electron injection layer with another vacuum vapor deposition apparatus. Thus, an OLED device was produced.
  • the minimum time taken to be reduced from 100% to 97% of the luminance at 5,000 nit was 159 hours.
  • An OLED device was produced in the same manner as in Device Example 1, except for using C-7 as a second hole transport material.
  • the minimum time taken to be reduced from 100% to 97% of the luminance at 5,000 nit was 258 hours.
  • An OLED device was produced in the same manner as in Device Example 1, except for using C-58 as a second hole transport material.
  • the minimum time taken to be reduced from 100% to 97% of the luminance at 5,000 nit was 221 hours.
  • An OLED device was produced in the same manner as in Device Example 1, except for using C-10 as a second hole transport material and compound C as a host.
  • the minimum time taken to be reduced from 100% to 97% of the luminance at 5,000 nit was 1.8 hours.
  • An OLED device was produced in the same manner as in Device Example 1, except for using C-10 as a second hole transport material and compound D as a host.
  • the minimum time taken to be reduced from 100% to 97% of the luminance at 5,000 nit was 21.4 hours.
  • An OLED device was produced in the same manner as in Device Example 1, except for using compound A as a second hole transport material and H-17 as a host.
  • the minimum time taken to be reduced from 100% to 97% of the luminance at 5,000 nit was 16.5 hours.
  • An OLED device was produced in the same manner as in Device Example 1, except for using compound B as a second hole transport material and H-17 as a host.
  • the minimum time taken to be reduced from 100% to 97% of the luminance at 5,000 nit was 137 hours.
  • the present disclosure has confirmed that the organic electroluminescence device is manufactured by using a combination of a specific hole transport material and a host compound, so that the driving lifetime is much better than that of a conventional organic electroluminescence device.
  • the HOMO (highest occupied molecular orbital) energy level of the compound comprising spirofluorene used in a hole transport material is formed to be 4.7 to 4.8 eV.
  • the compound in which a benzene ring is fused to one of two carbazole of a biscarbazole structure used as a host material of a light-emitting layer and heteroaryl containing nitrogen is bonded to one of two nitrogen atoms has a HOMO energy level of 5.0 eV, so that the hole injection ability can be improved due to the relatively low energy barrier, thereby reducing the deterioration phenomenon at the interface between the hole transport layer and the light-emitting layer, and improving the lifespan of the device.
  • the present disclosure relates to the combination of a benzo-HOMO (highest occupied molecular orbital) site of a cabazole group and a spirofluorene group so that it is possible to smoothly transfer a hole to the light-emitting layer in the organic electroluminescence device.
  • the phenomenon extends the recombination region to generate more excitons and recombine more electron-hole pairs.
  • the device of the present discloure can have better lifespan characteristics than the devices containing each of the aforementioned components.

Abstract

La présente invention concerne un dispositif électroluminescent organique. Le dispositif électroluminescent organique de la présente invention comprend une combinaison spécifique d'un composé hôte et d'un matériau de transport de trous qui peut fournir d'excellentes caractéristiques de durée de vie.
PCT/KR2017/011300 2016-10-14 2017-10-13 Dispositif électroluminescent organique WO2018070821A1 (fr)

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WO2018180709A1 (fr) * 2017-03-28 2018-10-04 東レ株式会社 Composé, dispositif électronique le contenant, élément électroluminescent à film mince organique, dispositif d'affichage et dispositif d'éclairage
CN109251148A (zh) * 2018-09-11 2019-01-22 武汉华星光电半导体显示技术有限公司 覆盖层分子结构、制作方法及对应的oled器件
CN111785841A (zh) * 2020-07-09 2020-10-16 吉林奥来德光电材料股份有限公司 一种有机电致发光器件及其应用

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US20140367649A1 (en) * 2013-06-14 2014-12-18 Samsung Display Co., Ltd. Organic light-emitting devices
WO2016013867A1 (fr) * 2014-07-22 2016-01-28 Rohm And Haas Electronic Materials Korea Ltd. Dispositif électroluminescent organique
US20160260905A1 (en) * 2015-03-03 2016-09-08 Samsung Display Co., Ltd. Organic light-emitting device
US20170288147A1 (en) * 2016-03-30 2017-10-05 Samsung Display Co., Ltd. Organic light emitting device

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US20140367649A1 (en) * 2013-06-14 2014-12-18 Samsung Display Co., Ltd. Organic light-emitting devices
WO2016013867A1 (fr) * 2014-07-22 2016-01-28 Rohm And Haas Electronic Materials Korea Ltd. Dispositif électroluminescent organique
US20160260905A1 (en) * 2015-03-03 2016-09-08 Samsung Display Co., Ltd. Organic light-emitting device
US20170288147A1 (en) * 2016-03-30 2017-10-05 Samsung Display Co., Ltd. Organic light emitting device

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2018180709A1 (fr) * 2017-03-28 2018-10-04 東レ株式会社 Composé, dispositif électronique le contenant, élément électroluminescent à film mince organique, dispositif d'affichage et dispositif d'éclairage
CN109251148A (zh) * 2018-09-11 2019-01-22 武汉华星光电半导体显示技术有限公司 覆盖层分子结构、制作方法及对应的oled器件
CN111785841A (zh) * 2020-07-09 2020-10-16 吉林奥来德光电材料股份有限公司 一种有机电致发光器件及其应用
CN111785841B (zh) * 2020-07-09 2022-05-27 吉林奥来德光电材料股份有限公司 一种有机电致发光器件及其应用

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