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WO2018062758A1 - Matériau électroluminescent organique et dispositif électroluminescent organique le comprenant - Google Patents

Matériau électroluminescent organique et dispositif électroluminescent organique le comprenant Download PDF

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Publication number
WO2018062758A1
WO2018062758A1 PCT/KR2017/010326 KR2017010326W WO2018062758A1 WO 2018062758 A1 WO2018062758 A1 WO 2018062758A1 KR 2017010326 W KR2017010326 W KR 2017010326W WO 2018062758 A1 WO2018062758 A1 WO 2018062758A1
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Prior art keywords
substituted
unsubstituted
alkyl
ring
organic electroluminescent
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WO2018062758A9 (fr
Inventor
Bitnari Kim
Hyun Kim
Dong Hyung Lee
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DuPont Specialty Materials Korea Ltd
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Rohm and Haas Electronic Materials Korea Ltd
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Priority claimed from KR1020160130817A external-priority patent/KR102863646B1/ko
Application filed by Rohm and Haas Electronic Materials Korea Ltd filed Critical Rohm and Haas Electronic Materials Korea Ltd
Priority to US16/327,877 priority Critical patent/US20190221758A1/en
Priority to EP17856644.4A priority patent/EP3519532A4/fr
Priority to CN201780056766.3A priority patent/CN109715759B/zh
Priority to JP2019513883A priority patent/JP2019533035A/ja
Publication of WO2018062758A1 publication Critical patent/WO2018062758A1/fr
Publication of WO2018062758A9 publication Critical patent/WO2018062758A9/fr
Anticipated expiration legal-status Critical
Priority to JP2022082985A priority patent/JP2022122903A/ja
Ceased legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/04—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
    • 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
    • H05B33/14—Light sources with substantially two-dimensional radiating surfaces characterised by the chemical or physical composition or the arrangement of the electroluminescent material, or by the simultaneous addition of the electroluminescent material in or onto the light source
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/30—Coordination compounds
    • H10K85/341—Transition metal complexes, e.g. Ru(II)polypyridine complexes
    • H10K85/342—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising iridium
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K2101/00—Properties of the organic materials covered by group H10K85/00
    • H10K2101/10—Triplet emission
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole

Definitions

  • the present disclosure relates to an organic electroluminescent material comprising at least two types of compounds and an organic electroluminescent device comprising the same.
  • An electroluminescent device is a self-light-emitting display device which has advantages in that it provides a wider viewing angle, a greater contrast ratio, and a faster response time.
  • the first organic EL device was developed by Eastman Kodak in 1987, by using small aromatic diamine molecules and aluminum complexes as materials for forming a light-emitting layer ( see Appl. Phys. Lett. 51, 913, 1987).
  • An organic EL device changes electric energy into light by applying electricity to an organic electroluminescent material, and commonly comprises an anode, a cathode, and an organic layer formed between the two electrodes.
  • the organic layer of the organic EL device may comprise a hole injection layer, a hole transport layer, a hole auxiliary layer, a light-emitting auxiliary layer, an electron blocking layer, a light-emitting layer (containing host and dopant materials), an electron buffer layer, a hole blocking layer, an electron transport layer, an electron injection layer, etc., if necessary.
  • the materials used in the organic layer can be classified into a hole injection material, a hole transport material, a hole auxiliary material, a light-emitting auxiliary material, an electron blocking material, a light-emitting material, an electron buffer material, a hole blocking material, an electron transport material, an electron injection material, etc., depending on their functions.
  • a hole injection material a hole transport material, a hole auxiliary material, a light-emitting auxiliary material, an electron blocking material, a light-emitting material, an electron buffer material, a hole blocking material, an electron transport material, an electron injection material, etc.
  • holes from the anode and electrons from the cathode are injected into a light-emitting layer by the application of electric voltage, and excitons having high energy are 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 an energy when the organic light-emitting compound returns to the ground state from the excited state
  • the most important factor determining luminous efficiency in an organic EL device is light-emitting materials.
  • the light-emitting materials are required to have the following features: high quantum efficiency, high mobility of an electron and a hole, and uniformity and stability of the formed light-emitting material layer.
  • the light-emitting material is classified into blue, green, and red light-emitting materials according to the light-emitting color, and further includes yellow or orange light-emitting materials. Furthermore, the light-emitting material is classified into a host material and a dopant material in a functional aspect.
  • a device having excellent EL characteristics has a structure comprising a light-emitting layer made by doping a dopant to a host.
  • a problem arises in that the maximum emission wavelength moves toward a long wavelength and the color purity deteriorates due to intermolecular forces.
  • Iridium(III) complexes have been widely known as phosphorescent light-emitting materials, including bis(2-(2'-benzothienyl)-pyridinato-N,C-3')iridium(acetylacetonate) [(acac)Ir(btp) 2 ], tris(2-phenylpyridine)iridium [Ir(ppy) 3 ] and bis(4,6-difluorophenylpyridinato-N,C2)picolinato iridium (Firpic) as red, green, and blue light-emitting materials, respectively.
  • CBP 4,4'-N,N'-dicarbazol-biphenyl
  • BCP bathocuproine
  • BAlq aluminum(III) bis(2-methyl-8-quinolinate)(4-phenylphenolate)
  • Korean Patent No. 1082144 discloses an organic electroluminescent device comprising an indolocarbazole derivative, or a compound wherein a dibenzoindolocarbazole and a naphthyridinyl are combined, as a host.
  • Korean Patent Application Laid-Open No. 2016-0039561 discloses an organic electroluminescent device comprising an indolocarbazole derivative as a host.
  • the aforementioned documents do not specifically disclose a device comprising a benzoindolocarbazole as a host.
  • the objective of the present disclosure is to provide an organic electroluminescent material for producing an organic electroluminescent device having better color purity than a conventional organic electroluminescent device.
  • the present inventors found that the color reproduction range can be increased by drawing the wavelength band toward the longest wavelength in red light-emission.
  • the characteristics of the dopant material of host and dopant materials more influence the wavelength band, it is possible to further optimize the luminous characteristics by using a host material suitable for the dopant material.
  • the energy band gap of the dopant material is narrow since it has a long wavelength.
  • the host material used in the present disclosure has a narrow energy band gap, which is suitable for the dopant material having a long wavelength.
  • the combination is suitable for the objective of transferring energy from a host to a dopant.
  • an organic electroluminescent material comprising a compound represented by the following formula 1 and a compound represented by the following formula 2.
  • the compound represented by formula 1 may be comprised as a dopant, and the compound represented by formula 2 may be comprised as a host.
  • R 1 to R 3 each independently, represent hydrogen, deuterium, a substituted or unsubstituted (C1-C10)alkyl, a substituted or unsubstituted (C2-C10)alkenyl, or a substituted or unsubstituted (C6-C30)aryl, or may be linked to an adjacent substituent to form a substituted or unsubstituted, mono- or polycyclic, (C3-C30) alicyclic or aromatic ring, or the combination thereof, whose carbon atom(s) may be replaced with at least one heteroatom selected from nitrogen, oxygen, and sulfur,
  • R 4 represents a substituted or unsubstituted (C1-C10)alkyl, or a substituted or unsubstituted (C6-C30)aryl,
  • R 5 to R 7 each independently, represent hydrogen, deuterium, a substituted or unsubstituted (C1-C10)alkyl, or a substituted or unsubstituted (C6-C30)aryl,
  • a and b each independently, represent an integer of 1 to 4, where if a and b, each independently, are an integer of 2 or more, each of R 1 and R 2 may be the same or different.
  • a ring and B ring each independently, represent a substituted or unsubstituted benzene ring, or a substituted or unsubstituted naphthalene ring, with a proviso that at least one of A ring and B ring is a substituted or unsubstituted naphthalene ring,
  • Ar 1 and Ar 2 each independently, represent a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted nitrogen-containing (8- to 30-membered)heteroaryl,
  • L 1 and L 2 each independently, represent a single bond, a substituted or unsubstituted (C6-C30)arylene, or a substituted or unsubstituted (3- to 30-membered)heteroarylene, and
  • the heteroaryl(ene) contains at least one heteroatom selected from B, N, O, S, Si, and P.
  • an organic electroluminescent device having excellent color purity can be provided.
  • an organic electroluminescent material in the present disclosure means a material that may be used in an organic electroluminescent device, and may comprise at least one compound. If necessary, the organic electroluminescent material may be comprised in any layers constituting an organic electroluminescent device.
  • the organic electroluminescent material may be a hole injection material, a hole transport material, a hole auxiliary material, a light-emitting auxiliary material, an electron blocking material, a light-emitting material, an electron buffer material, a hole blocking material, an electron transport material, an electron injection material, etc.
  • the organic electroluminescent material of the present disclosure may comprise at least one compound represented by formula 1, and at least one compound represented by formula 2.
  • the compound of formula 1 and the compound of formula 2 may be included in the light-emitting layer.
  • the compound of formula 1 may be included as a dopant, and the compound of formula 2 may be included as a host.
  • R 1 to R 3 each independently, represent hydrogen, deuterium, a substituted or unsubstituted (C1-C10)alkyl, a substituted or unsubstituted (C2-C10)alkenyl, or a substituted or unsubstituted (C6-C30)aryl, or may be linked to an adjacent substituent to form a substituted or unsubstituted, mono- or polycyclic, (C3-C30) alicyclic or aromatic ring, or the combination thereof, whose carbon atom(s) may be replaced with at least one heteroatom selected from nitrogen, oxygen, and sulfur; as one embodiment, hydrogen, a substituted or unsubstituted (C1-C8)alkyl, or a substituted or unsubstituted (C6-C25)aryl, or may be linked to an adjacent substituent to form a substituted or unsubstituted, mono- or polycyclic, (C5-C25) alicyclic or aromatic ring
  • R 1 may represent hydrogen, an unsubstituted methyl, a phenyl unsubstituted or substituted with a methyl(s), or an unsubstituted biphenyl, or may be linked to an adjacent substituent to form an indene ring substituted with a methyl(s);
  • R 2 may represent hydrogen, or an unsubstituted methyl; and
  • R 3 may represent hydrogen.
  • R 4 represents a substituted or unsubstituted (C1-C10)alkyl, or a substituted or unsubstituted (C6-C30)aryl; as one embodiment, a substituted or unsubstituted (C1-C8)alkyl, or a substituted or unsubstituted (C6-C25)aryl; as another embodiment, a substituted or unsubstituted (C1-C4)alkyl, or a substituted or unsubstituted (C6-C18)aryl; and for example, an unsubstituted methyl, an unsubstituted iso -butyl; a phenyl unsubstituted or substituted with a methyl(s), an iso -butyl(s) and/or a tert -butyl(s).
  • R 5 to R 7 each independently, represent hydrogen, deuterium, a substituted or unsubstituted (C1-C10)alkyl, or a substituted or unsubstituted (C6-C30)aryl; and as one embodiment, hydrogen, a substituted or unsubstituted (C1-C8)alkyl, or a substituted or unsubstituted (C6-C25)aryl.
  • R 5 and R 7 each independently, represent an unsubstituted (C1-C5)alkyl, or a substituted or unsubstituted (C6-C18)aryl
  • R 6 represents hydrogen, an unsubstituted (C1-C5)alkyl, or a substituted or unsubstituted (C6-C18)aryl.
  • R 5 and R 7 each independently, may represent an unsubstituted methyl, an unsubstituted butyl, an unsubstituted tert -butyl, an unsubstituted iso -butyl, an unsubstituted pentyl, or an unsubstituted phenyl; and R 6 may represent hydrogen, an unsubstituted methyl, or an unsubstituted phenyl.
  • a and b each independently, represent an integer of 1 to 4; as one embodiment, may represent 1 or 2, where if a and b, each independently, are an integer of 2 or more, each of R 1 and R 2 may be the same or different,
  • a ring and B ring each independently, represent a substituted or unsubstituted benzene ring, or a substituted or unsubstituted naphthalene ring, with a proviso that at least one of A ring and B ring is a substituted or unsubstituted naphthalene ring.
  • any one of A ring and B ring may represent a substituted or unsubstituted benzene ring, and the other may represent a substituted or unsubstituted naphthalene ring.
  • a ring and B ring each independently, may represent an unsubstituted benzene ring, or a naphthalene ring unsubstituted or substituted with a phenyl(s).
  • Ar 1 and Ar 2 each independently, represent a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted nitrogen-containing (8- to 30-membered)heteroaryl. Any one of Ar 1 and Ar 2 may represent a substituted or unsubstituted (C6-C30)aryl, and the other may represent a substituted or unsubstituted nitrogen-containing (8- to 30-membered)heteroaryl.
  • Ar 1 and Ar 2 each independently, represent a substituted or unsubstituted (C6-C25)aryl, or a substituted or unsubstituted nitrogen-containing (8- to 25-membered)heteroaryl; and as another embodiment, represent a substituted or unsubstituted (C6-C18)aryl, or a substituted or unsubstituted nitrogen-containing (8- to 18-membered)heteroaryl.
  • Ar 1 and Ar 2 each independently, represent an unsubstituted phenyl; an unsubstituted naphthyl; a quinazolinyl substituted with a phenyl(s); or a quinoxalinyl unsubstituted or substituted with a phenyl(s), a biphenyl(s), a naphthyl(s) and/or a naphthylphenyl(s).
  • L 1 and L 2 each independently, represent a single bond, a substituted or unsubstituted (C6-C30)arylene, or a substituted or unsubstituted (3- to 30-membered)heteroarylene; as one embodiment, a single bond, a substituted or unsubstituted (C6-C25)arylene, or a substituted or unsubstituted (5- to 25-membered)heteroarylene; as another embodiment, a single bond, a substituted or unsubstituted (C6-C18)arylene, or a substituted or unsubstituted (5- to 18-membered)heteroarylene; and for example, a single bond, an unsubstituted phenylene, or an unsubstituted pyridinylene.
  • the heteroaryl(ene) contains at least one heteroatom selected from B, N, O, S, Si, and P; as one embodiment, may contain at least one heteroatom selected from N, O and S; as another embodiment, may contain a nitrogen(s).
  • formula 1 may be represented by any one of the following formulas 3 to 6.
  • Y represents CR 13 R 14 , O or S; and as one embodiment, may represent CR 13 R 14 .
  • R 8 , R 13 and R 14 each independently, represent hydrogen, deuterium, a substituted or unsubstituted (C1-C10)alkyl, or a substituted or unsubstituted (C6-C30)aryl; as one embodiment, hydrogen, a substituted or unsubstituted (C1-C8)alkyl, or a substituted or unsubstituted (C6-C18)aryl; and as another embodiment, hydrogen, or a substituted or unsubstituted (C1-C4)alkyl.
  • R 8 may represent hydrogen, and R 13 and R 14 , each independently, may represent an unsubstituted (C1-C4)alkyl.
  • R 8 may represent hydrogen, and R 13 and R 14 , each independently, may represent an unsubstituted methyl.
  • R 12 represents hydrogen, deuterium, a substituted or unsubstituted (C1-C10)alkyl, or a substituted or unsubstituted (C6-C30)aryl; as one embodiment, hydrogen, a substituted or unsubstituted (C1-C8)alkyl, or a substituted or unsubstituted (C6-C25)aryl; as another embodiment, hydrogen, an unsubstituted (C1-C4)alkyl, or an unsubstituted (C6-C18)aryl; and for example, hydrogen, an unsubstituted methyl, or an unsubstituted phenyl.
  • R 9 to R 11 each independently, represent hydrogen, or a substituted or unsubstituted (C1-C10)alkyl; as one embodiment, may represent hydrogen, or a substituted or unsubstituted (C1-C8)alkyl; as another embodiment, may represent hydrogen, or a substituted or unsubstituted (C1-C4)alkyl; and for example, may represent hydrogen.
  • c represents an integer of 1 to 4
  • d represents an integer of 1 to 5, where if c and d, each independently, are an integer of 2 or more, each of R 8 and R 12 may be the same or different.
  • c and d, each independently, may represent 1 or 2.
  • c and d, each independently, may represent 1.
  • R 2 to R 7 , and b are as defined in formula 1.
  • formula 2 may be represented by the following formula 7.
  • any one of A ring and B ring represents a substituted or unsubstituted naphthalene ring, and the other represents a substituted or unsubstituted benzene ring.
  • any one of A ring and B ring represents a naphthalene ring unsubstituted or substituted with a phenyl(s), and the other represents an unsubstituted benzene ring.
  • X 1 to X 3 each independently, represent CR 15 or N, with a proviso that at least one of X 1 to X 3 represents N; as one embodiment, at least two of X 1 to X 3 may represent N; and as another embodiment, two of X 1 to X 3 may represent N.
  • X 1 may represent N; any one of X 2 and X 3 may represnet N; and the other of X 2 and X 3 may represent CR 15 .
  • R 15 represents hydrogen, or a substituted or unsubstituted (C6-C30)aryl; as one embodiment, may represent a substituted or unsubstituted (C6-C25)aryl; as another embodiment, may represent a substituted or unsubstituted (C6-C18)aryl; and for example, an unsubstituted phenyl, an unsubstituted naphthyl, an unsubstituted biphenyl, or an unsubstituted naphthylphenyl.
  • Ar 3 represents represent hydrogen, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (3- to 30-membered)heteroaryl; as one embodiment, hydrogen, a substituted or unsubstituted (C1-C20)alkyl, a substituted or unsubstituted (C6-C25)aryl, or a substituted or unsubstituted (3- to 25-membered)heteroaryl; as another embodiment, hydrogen, a substituted or unsubstituted (C1-C10)alkyl, a substituted or unsubstituted (C6-C18)aryl, or a substituted or unsubstituted (5- to 18-membered)heteroaryl; and for example, hydrogen.
  • e represents an integer of 1 to 4; as one embodiment, may represent 1 or 2; and as another embodiment, may represent 1. If e is an integer of 2 or more, each of Ar 3 may be the same or different.
  • Ar 1 , L 1 and L 2 are as defined in formula 2.
  • (C1-C30)alkyl is meant to be a linear or branched alkyl having 1 to 30 carbon atoms constituting the chain, in which the number of carbon atoms is preferably 1 to 20, and more preferably 1 to 10.
  • the above alkyl may include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, 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, and more preferably 3 to 7.
  • the above cycloalkyl may include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, etc.
  • the term “(3- to 7-membered) heterocycloalkyl” is a cycloalkyl having 3 to 7, preferably 5 to 7, ring backbone atoms, and including at least one heteroatom selected from the group consisting of B, N, O, S, Si, and P, and preferably the group consisting of O, S, and N.
  • the above heterocycloalkyl may include 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, in which the number of the ring backbone carbon atoms is preferably 6 to 25, more preferably 6 to 18.
  • the above aryl(ene) may be partially saturated, and may comprise a spiro structure.
  • the above aryl may include phenyl, biphenyl, terphenyl, naphthyl, binaphthyl, phenylnaphthyl, naphthylphenyl, fluorenyl, phenylfluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, phenylphenanthrenyl, anthracenyl, indenyl, triphenylenyl, pyrenyl, tetracenyl, perylenyl, chrysenyl, naphthacenyl, fluoranthenyl, spirobifluorenyl, etc.
  • (3- to 30-membered)heteroaryl(ene) is an aryl having 3 to 30 ring backbone atoms, and including at least one, preferably 1 to 4 heteroatoms selected from the group consisting of B, N, O, S, Si, and P.
  • the above heteroaryl(ene) 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 may comprise a spiro structure.
  • the above heteroaryl may include 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, and pyridazinyl, and a fused ring-type heteroaryl such as benzofuranyl, benzothiophenyl, isobenzofuranyl, dibenzofuranyl, dibenzothiophenyl, benzimidazolyl, benzothiazolyl, benzoisothiazolyl, benzoisoxazolyl, benzoxazolyl, isoindolyl
  • substituted in the expression “substituted or unsubstituted” means that a hydrogen atom in a certain functional group is replaced with another atom or another functional group, i.e. a substituent.
  • the compound represented by formula 1 includes the following compounds, but is not limited thereto.
  • the compound represented by formula 2 includes the following compounds, but is not limited thereto.
  • organic electroluminescent compounds represented by formulas 1 and 2 of the present disclosure may be produced by a synthetic method known to a person skilled in the art, and, for example, referring to the following method, but is not limited thereto.
  • the compound represented by formula 3 may be synthesized as shown in the following reaction scheme 1.
  • the compound represented by formula 4 may be synthesized by the method disclosed in Korean Patent No. 1636310.
  • the compound represented by formula 2 may be synthesized as shown in the following reaction scheme 2 or 3.
  • the organic electroluminescent device of the present disclosure may comprise a first electrode, a second electrode, and at least one organic layer between the first and second electrodes.
  • the organic layer may comprise a light-emitting layer.
  • the light-emitting layer may comprise at least one compound represented by formula 1 and at least one compound represented by formula 2, and the compound represented by formula 1 may be comprised as a dopant compound, and the compound represented by formula 2 may be comprised as a host compound.
  • the organic layer may comprise a light-emitting layer, and may further comprise at least one layer selected from a hole injection layer, a hole transport layer, a hole auxiliary layer, a light-emitting auxiliary layer, an electron transport layer, an electron buffer layer, an electron injection layer, an interlayer, a hole blocking layer, and an electron blocking layer.
  • the hole auxiliary layer or the light-emitting auxiliary layer may be placed between the hole transport layer and the light-emitting layer, and may control the hole transport rate.
  • the hole auxiliary layer or the light-emitting auxiliary layer may have an effect of improving the efficiency and/or the lifespan of the organic electroluminescent device.
  • the light-emitting layer is a layer from which light is emitted, and can be a single layer or a multi-layer of which two or more layers are stacked. In the light-emitting layer, it is preferable that the doping concentration of the dopant compound based on the host compound is less than 20 wt%.
  • the combination of dopant and host may be provided as the combination of at least one dopant compound represented by formula 1 and at least one host compound represented by formula 2.
  • the organic electroluminescent device comprising the combination of dopant and host may be provided.
  • an organic electroluminescent material comprising a combination of at least one dopant compound represented by formula 1 and at least one host compound represented by formula 2, and an organic electroluminescent device comprising the material may be provided.
  • the material may consist of only the combination of the compound of formula 1 and the compound of formula 2, and may further comprise conventional materials comprised in an organic electroluminescent material.
  • the organic layer comprising a combination of at least one dopant compound represented by formula 1 and at least one host compound represented by formula 2 may be provided.
  • the organic layer may comprise a plurality of layers, and the dopant compound and the host compound may be comprised in the same layer or different layers, respectively.
  • an organic electroluminescent device comprising the organic layer may be provided in present disclosure.
  • the organic electroluminescent device of the present disclosure may comprise the compounds of formulas 1 and 2, and further comprise at least one compound selected from the group consisting of arylamine-based compounds and styrylarylamine-based compounds.
  • the organic layer may further comprise at least one metal selected from the group consisting of metals of Group 1, metals of Group 2, transition metals of the 4 th period, transition metals of the 5 th period, lanthanides and organic metals of d-transition elements of the Periodic Table, or at least one complex compound comprising said metal, besides the compounds of formulas 1 and 2.
  • the organic layer may further comprise a light-emitting layer and a charge generating layer.
  • the organic electroluminescent device of the present disclosure may emit white light by further including at least one light-emitting layer containing a blue, red or green light-emitting compound, which are known in the art. Further, it may further comprise a yellow or orange light-emitting layer, if necessary.
  • a surface layer may be preferably placed on an inner surface(s) of one or both electrodes.
  • a chalcogenide (including 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.
  • Such a surface layer may provide operation stability for the organic electroluminescent device.
  • the chalcogenide includes SiO X (1 ⁇ X ⁇ 2), AlO X (1 ⁇ X ⁇ 1.5), SiON, SiAlON, etc.;
  • the metal halide includes LiF, MgF 2 , CaF 2 , a rare earth metal fluoride, etc.; and the metal oxide includes Cs 2 O, Li 2 O, MgO, SrO, BaO, CaO, etc.
  • a mixed region of an electron transport compound and a reductive dopant, or a mixed region of a hole transport compound and an oxidative dopant is preferably 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; 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 organic electroluminescent device having two or more light-emitting layers and emitting white light.
  • dry film-forming methods such as vacuum evaporation, sputtering, plasma and ion plating methods, or wet film-forming methods such as ink jet printing, nozzle printing, slot coating, spin coating, dip coating, and flow coating methods may be used.
  • the dopant and host compounds of the present disclosure may be co-evaporated or mixture-evaporated.
  • a thin film may be formed by dissolving or diffusing materials forming each layer into any suitable solvent such as ethanol, chloroform, tetrahydrofuran, dioxane, etc.
  • the solvent may 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 co-evaporation is a mixed deposition method in which two or more isomer materials are placed in a respective individual crucible source and a current is applied to both cells at the same time to evaporate the materials.
  • the mixture-evaporation is a mixed deposition method in which two or more isomer materials are mixed in one crucible source before evaporating them, and a current is applied to the cell to evaporate the materials.
  • a display system or a lighting system can be produced by using the organic electroluminescent device of the present disclosure.
  • the luminous properties of the organic light-emitting diode (OLED) device comprising the dopant copmpoud and the host compound of the present disclosure will be explained in detail by comparing with the conventional OLED device.
  • the present disclosure is not limited by the following examples.
  • An OLED device was produced by using the organic electroluminescent compound according to the present disclosure.
  • 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.
  • Compound 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.
  • compound 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.
  • Compound 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.
  • Compound HT-2 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: Compound H-2 was introduced into one cell of the vacuum vapor depositing apparatus as a host, and compound D-11 was introduced into another cell as a dopant. 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 40 nm on the second hole transport layer.
  • Compound ET-1 and compound EI-1 were then introduced into the other two cells and evaporated at a rate of 1:1 to form an electron transport layer having a thickness of 30 nm on the light-emitting layer.
  • an Al cathode having a thickness of 80 nm was deposited on the electron injection layer by another vacuum vapor deposition apparatus.
  • an OLED device was produced.
  • An OLED device was produced in the same manner as in Device Example 1, except that compound D-1 was used as a dopant.
  • Comparative Example 1 Producing an OLED device comprising a
  • An OLED device was produced in the same manner as in Device Example 1, except that the following compound X was used as a dopant.
  • the color reproduction range was calculated under the standard of the color space made by the National Television System Committee (NTSC), which is based on the color coordinate system defined by the International Commission on Illumination (CIE).
  • NTSC area The area of the triangle formed by the three points of red (0.67, 0.33), green (0.21, 0.71), and blue (0.14, 0.08) defined by NTSC is calculated (hereinafter, “NTSC area”). Also, the area of the triangle is calculated by using NTSC definition values for blue and green, and the measured values in the produced device for red, and the ratio of the triangle area versus the NTSC area is then calculated.
  • NTSC Color Space The percentages of the areas of the Comparative Example and the Device Examples versus the NTSC area, i.e. NTSC Color Space, are calculated as shown in Table 1 below.
  • R(x) represents CIE X coordinate of red light-emission
  • R(y) represents CIE Y coordinate of red light-emission
  • G(x) represents CIE X coordinate of green light-emission
  • G(y) represents a CIE Y coordinate of green light-emission
  • B(x) represents a CIE X coordinate of blue light-emission
  • B(y) represents a CIE Y coordinate of blue light-emission.

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

Abstract

La présente invention concerne un matériau électroluminescent organique comprenant au moins deux types de composés et un dispositif électroluminescent organique le comprenant. Le dispositif électroluminescent organique qui a une pureté de couleur meilleure que celle d'un dispositif électroluminescent organique classique peut être obtenu en comprenant la combinaison spécifique des composés de la présente invention.
PCT/KR2017/010326 2016-09-30 2017-09-20 Matériau électroluminescent organique et dispositif électroluminescent organique le comprenant Ceased WO2018062758A1 (fr)

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US16/327,877 US20190221758A1 (en) 2016-09-30 2017-09-20 Organic electroluminescent material and organic electroluminescent device comprising the same
EP17856644.4A EP3519532A4 (fr) 2016-09-30 2017-09-20 Matériau électroluminescent organique et dispositif électroluminescent organique le comprenant
CN201780056766.3A CN109715759B (zh) 2016-09-30 2017-09-20 有机电致发光材料和包含所述材料的有机电致发光器件
JP2019513883A JP2019533035A (ja) 2016-09-30 2017-09-20 有機エレクトロルミネッセンス材料およびそれを含む有機エレクトロルミネッセンス素子
JP2022082985A JP2022122903A (ja) 2016-09-30 2022-05-20 有機エレクトロルミネッセンス材料およびそれを含む有機エレクトロルミネッセンス素子

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EP3725793A1 (fr) * 2019-04-16 2020-10-21 Samsung Electronics Co., Ltd. Composé organométallique, dispositif électroluminescent organique le comprenant et composition de diagnostic comprenant le composé organométallique
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KR20220142392A (ko) * 2021-04-14 2022-10-21 베이징 썸머 스프라우트 테크놀로지 컴퍼니 리미티드 유기 전계발광재료 및 그 소자
KR102856819B1 (ko) 2021-04-14 2025-09-05 베이징 썸머 스프라우트 테크놀로지 컴퍼니 리미티드 유기 전계발광재료 및 그 소자

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