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WO2018124697A1 - Composé électroluminescent organique et dispositif électroluminescent organique le comprenant - Google Patents

Composé électroluminescent organique et dispositif électroluminescent organique le comprenant Download PDF

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Publication number
WO2018124697A1
WO2018124697A1 PCT/KR2017/015481 KR2017015481W WO2018124697A1 WO 2018124697 A1 WO2018124697 A1 WO 2018124697A1 KR 2017015481 W KR2017015481 W KR 2017015481W WO 2018124697 A1 WO2018124697 A1 WO 2018124697A1
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Prior art keywords
substituted
unsubstituted
organic electroluminescent
alkyl
compound
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PCT/KR2017/015481
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English (en)
Inventor
Hyun Kim
Dong-Hyung Lee
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Rohm And Haas Electronic Materials Korea Ltd.
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Priority claimed from KR1020170178000A external-priority patent/KR102359412B1/ko
Application filed by Rohm And Haas Electronic Materials Korea Ltd. filed Critical Rohm And Haas Electronic Materials Korea Ltd.
Priority to CN202210969683.6A priority Critical patent/CN115181135A/zh
Priority to JP2019530396A priority patent/JP2020503672A/ja
Priority to CN201780075157.2A priority patent/CN110036499A/zh
Priority to US16/462,985 priority patent/US20190312218A1/en
Priority to EP17886492.2A priority patent/EP3563437A4/fr
Publication of WO2018124697A1 publication Critical patent/WO2018124697A1/fr
Priority to US17/666,885 priority patent/US20220165969A1/en

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    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/30—Coordination compounds
    • H10K85/341—Transition metal complexes, e.g. Ru(II)polypyridine complexes
    • H10K85/342—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising iridium
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/30—Coordination compounds
    • H10K85/361—Polynuclear complexes, i.e. complexes comprising two or more metal centers
    • 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
    • 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
    • H10K50/12—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers comprising dopants

Definitions

  • the present disclosure relates to an organic electroluminescent compound 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 [Appl. Phys. Lett. 51, 913, 1987].
  • An organic EL device changes electric energy into light by applying electricity to an organic light-emitting material, and commonly comprises an anode, a cathode, and an organic layer formed between the two electrodes.
  • the organic layer of the OLED 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 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 an anode and electrons from a cathode are injected into a light-emitting layer by the application of 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 most important factor determining luminous efficiency in an OLED is light-emitting materials.
  • the light-emitting materials are required to have the following features: high quantum efficiency, high movement degree of an electron and a hole, and uniformality and stability of the formed light-emitting material layer.
  • the light-emitting material may be classified into blue, green, and red light-emitting materials according to the light-emitting color, and further includes yellow or orange light-emitting materials.
  • the light-emitting material may be 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 formed by doping a dopant to a host.
  • Iridium(III) complexes have been widely known as a dopant of a phosphorescent light-emitting material, 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-emitting materials, respectively.
  • a phosphorescent light-emitting material including bis(2-(2'-benzothienyl)-pyridinato-N,C-3')iridium(acetylacetonate) [(acac)Ir(btp) 2 ], tris(2-phenylpyridine)iridium [Ir(ppy) 3
  • CBP 4,4'-N,N'-dicarbazol-biphenyl
  • BCP bathocuproine
  • BAlq aluminum(III) bis(2-methyl-8-quinolinate)(4-phenylphenolate)
  • U.S. Patent Application Publication No. 2015/357588 discloses the following compound as a phosphorescent light-emitting material.
  • Korean Patent Application Laid-Open No. 2011-0077350 discloses the following compound as a red phosphorescent light-emitting material.
  • organic electroluminescent devices comprising the compound disclosed in the aforementioned documents are still limited in showing high color purity while exhibiting high luminescent efficiency.
  • the objective of the present disclosure is firstly, to provide an organic electroluminescent compound capable of producing an organic electroluminescent device having low driving voltage and/or high luminous efficiency properties while exhibiting a deep red color, and secondly, to provide an organic electroluminescent device comprising the organic electroluminescent compound.
  • CIE 1931 colorimetric system The higher the X value in a standard colorimetric system set by the International Commission on Illumination (CIE) (hereinafter, referred to as "CIE 1931 colorimetric system"), the higher color purity of red, and thus, conventionally, the study has been conducted to develop a deep red organic electroluminescent device having a large X value in order to increase color purity.
  • CIE 1931 colorimetric system the luminous efficiency of the device is lowered.
  • an organic electroluminescent device having low driving voltage and/or high luminous efficiency properties while exhibiting deep red color can be provided by using a ligand specified by introducing an alkyl group having two or more carbons at the 6-position which is the farthest from the amine of isoquinoline, and thus the present invention has been completed.
  • the above objective can be achieved by an organic electroluminescent compound represented by the following formula 1, wherein an organic electroluminescent device comprising the organic electroluminescent compound represents a deep red color.
  • R 1 represents a substituted or unsubstituted (C2-C6)alkyl
  • R 2 and R 3 each independently, represent a substituted or unsubstituted (C1-C5)alkyl
  • R 4 to R 6 each independently, represent hydrogen, deuterium, a substituted or unsubstituted (C1-C5)alkyl, or a substituted or unsubstituted (C5-C30)aryl; or are linked to an adjacent substituent to form a substituted or unsubstituted, mono- or polycyclic, (C3-C30) alicyclic or aromatic ring, or the combination thereof, wherein the carbon atom(s) of the alicyclic or aromatic ring, or the combination thereof may be replaced with at least one heteroatom selected from nitrogen, oxygen, and sulfur.
  • organic electroluminescent compound of the present disclosure By comprising the organic electroluminescent compound of the present disclosure, it is possible to provide an organic electroluminescent device having low driving voltage and/or high luminous efficiency properties while exhibiting deep red color.
  • Figure 1 illustrates NMR data of compound C-4 which is the organic electroluminescent compound according to one embodiment of the present disclosure.
  • Figure 2 illustrates NMR data of compound C-2 which is the organic electroluminescent compound according to one embodiment of the present disclosure.
  • Figure 3 illustrates NMR data of compound C-16 which is the organic electroluminescent compound according to one embodiment of the present disclosure.
  • organic electroluminescent compound in the present disclosure means a compound that may be used in an organic electroluminescent device, and may be comprised in any layer constituting an organic electroluminescent device, as necessary.
  • organic electroluminescent material in the present disclosure means a material that may be used in an organic electroluminescent device, and may comprise at least one compound.
  • the organic electroluminescent material may be comprised in any layer constituting an organic electroluminescent device, as necessary.
  • the organic electroluminescent material may be a hole injection material, a hole transport material, a hole auxiliary material, a light-emitting auxiliary material, an electron blocking material, a light-emitting material, an electron buffer material, a hole blocking material, an electron transport material, or an electron injection material.
  • CIE 1931 colorimetric system in the present disclosure means a standard colorimetric system defined by the International Commission on Illumination (CIE) in 1931, and is based on the XYZ colorimetric system which is a CIE standard colorimetric system among RGB colorimetric system and XYZ colorimetric system.
  • the XYZ colorimetric system represents all colors as three parameters of X, Y and Z, based on the measurement value by the spectrophotometer.
  • X and Y indicate chromaticity, and a color is represented by a point of chromaticity coordinates made up of X and Y coordinates.
  • Z means lightness, and indicates luminous quantity, which is the amount of brightness of color.
  • the deep red color means that the X value of the CIE 1931 colorimetric system is about 0.68 or more, preferably about 0.69 or more.
  • R 1 represents a substituted or unsubstituted (C2-C6)alkyl, and preferably a (C2-C6)alkyl unsubstituted or substituted with deuterium.
  • the (C2-C6)alkyl may be any one selected from the group consisting of ethyl, n -propyl, isopropyl, n -butyl, isobutyl, sec -butyl, tert -butyl, n -pentyl, tert -pentyl, neopentyl, isopentyl, sec -pentyl and 3-pentyl, and the longer chain may be preferable.
  • R 1 represents a substituted or unsubstituted (C3-C5)alkyl. According to another embodiment of the present disclosure, R 1 represents a substituted or unsubstituted (C4-C5)alkyl.
  • R 2 and R 3 each independently, represent a substituted or unsubstituted (C1-C5)alkyl, preferably a (C1-C5)alkyl unsubstituted or substituted with deuterium, and more preferably a (C1-C4)alkyl unsubstituted or substituted with deuterium.
  • R 2 and R 3 may be the same or different from each other, and preferably the same.
  • the (C1-C5)alkyl is any one selected from the group consisting of methyl, ethyl, n -propyl, isopropyl, n -butyl, isobutyl, sec -butyl, tert -butyl, n -pentyl, tert -pentyl, neopentyl, isopentyl, sec -pentyl and 3-pentyl.
  • R 2 and R 3 each independently, may represent methyl, ethyl or isobutyl, and R 2 and R 3 may be the same.
  • R 4 to R 6 each independently, represent hydrogen, deuterium, a substituted or unsubstituted (C1-C5)alkyl, or a substituted or unsubstituted (C5-C30)aryl; or are linked to an adjacent substituent to form a substituted or unsubstituted, mono- or polycyclic, (C3-C30) alicyclic or aromatic ring, or the combination thereof, wherein the carbon atom(s) of the alicyclic or aromatic ring, or the combination thereof may be replaced with at least one heteroatom selected from nitrogen, oxygen, and sulfur.
  • R 4 to R 6 each independently, represent hydrogen, a substituted or unsubstituted (C1-C5)alkyl, or a substituted or unsubstituted (C5-C25)aryl.
  • the (C1-C5)alkyl is any one selected from the group consisting of methyl, ethyl, n -propyl, isopropyl, n -butyl, isobutyl, sec -butyl, tert -butyl, n -pentyl, tert -pentyl, neopentyl, isopentyl, sec -pentyl and 3-pentyl.
  • R 4 and R 6 each independently, represent an unsubstituted (C1-C5)alkyl, or an unsubstituted (C5-C18)aryl.
  • R 4 and R 6 each independently, represent methyl, isopropyl, isobutyl, sec -butyl, sec -pentyl, 3-pentyl or phenyl.
  • R 4 and R 6 may be the same or different from each other.
  • R 5 represents hydrogen, an unsubstituted (C1-C5)alkyl, or an unsubstituted (C5-C18)aryl.
  • R 5 represents hydrogen, methyl, or phenyl.
  • formula 1 may represent any one selected from the group consisting of the following, but is not limited thereto.
  • formula 1 may represent any one selected from the group consisting of the following, but is not limited thereto.
  • (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, iso -propyl, n -butyl, iso -butyl, tert -butyl, etc.
  • (C3-C30)cycloalkyl is meant to be 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 meant to be 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 meant to be 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
  • the compound represented by formula 1 includes the following compounds, but is not limited thereto.
  • the compound represented by formula 1 of the present disclosure may be produced by a synthetic method known to one skilled in the art.
  • the compound represented by formula 1 may be synthesized as shown in the following reaction scheme 1 or 2, but is not limited thereto.
  • R 1 to R 6 are as defined in formula 1.
  • the host compound capable to be used in combination with the compound of the present disclosure may be a compound represented by any one of the following formulas 2 to 4, but is not limited thereto.
  • Ma represents a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (6- to 30-membered)heteroaryl,
  • La represents a single bond, a substituted or unsubstituted (C6-C30)arylene, or a substituted or unsubstituted (6- to 30-membered)heteroarylene,
  • A represents S, O, NR 7 , or CR 8 R 9 ,
  • Xa to Xh each independently, represent hydrogen, deuterium, a halogen, a cyano, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C2-C30)alkenyl, a substituted or unsubstituted (C2-C30)alkynyl, a substituted or unsubstituted (C3-C30)cycloalkyl, a substituted or unsubstituted (C6-C60)aryl, a substituted or unsubstituted (3- to 30-membered)heteroaryl, a substituted or unsubstituted tri(C1-C30)alkylsilyl, a substituted or unsubstituted tri(C6-C30)arylsilyl, a substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, a
  • R 7 to R 9 each independently, represent hydrogen, deuterium, a halogen, a cyano, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (3- to 30-membered)heteroaryl, a substituted or unsubstituted (C3-C30)cycloalkyl, a substituted or unsubstituted (C1-C30)alkoxy, a substituted or unsubstituted tri(C1-C30)alkylsilyl, a substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, a substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, a substituted or unsubstituted tri(C6
  • the heteroaryl(ene) contains at least one heteroatom selected from B, N, O, S, Si, and P.
  • La preferably represents a single bond, a substituted or unsubstituted (C6-C25)arylene, or a substituted or unsubstituted (6- to 25-membered)heteroarylene; and more preferably represents a single bond, an unsubstituted (C6-C18)arylene, or a (6- to 20-membered)heteroarylene unsubstituted or substituted with phenyl, biphenyl and/or carbazolyl.
  • La may represent a single bond; an unsubstituted phenylene; an unsubstituted naphthylene; an unsubstituted biphenylene; a pyridinylene unsubstituted or substituted with phenyl; a pyrimidinylene unsubstituted or substituted with phenyl, biphenyl and/or carbazolyl; a triazinylene unsubstituted or substituted with phenyl, biphenyl and/or carbazolyl; an unsubstituted quinolinylene; quinazolinylene unsubstituted or substituted with phenyl; an unsubstituted quinoxalinylene; an unsubstituted carbazolylene; an unsubstituted dibenzothiophenylene; an unsubstituted benzofuropyrimidinylene; an unsubstituted benzothienopyrimidinylene; an unsubsubsti
  • Ma preferably represents a substituted or unsubstituted (C6-C25)aryl, or a substituted or unsubstituted (6- to 25-membered)heteroaryl; and more preferably represents a substituted or unsubstituted (C6-C18)aryl, or a substituted or unsubstituted (6- to 20-membered)heteroaryl.
  • Ma represents a substituted or unsubstituted phenyl, a substituted or unsubstituted naphthylphenyl, an unsubstituted naphthyl, an unsubstituted biphenyl, a fluorenyl substituted with at least one methyl, an unsubstituted terphenyl, an unsubstituted triphenylenyl, a substituted pyrimidinyl, a substituted triazinyl, a substituted quinoxalinyl, a substituted quinazolinyl, a substituted or unsubstituted carbazolyl, an unsubstituted dibenzothiophenyl, a benzofuropyrimidinyl substituted with a phenyl, a benzothienopyrimidinyl substituted with a phenyl, a benzoquinazolinyl substituted with a phenyl, or an indo
  • the substituent of the substituted phenyl may be at least one selected from the group consisting of a carbazolyl unsubstituted or substituted with a phenyl, a pyrimidinyl substituted with at least one phenyl, a triphenylsilyl, a dibanzothiophenyl, a dimethylfluorenyl and a triphenylenyl;
  • the substituent of the substituted pyrimidinyl may be at least one selected from the group consisting of a phenyl, a biphenyl and a terphenyl;
  • the substituent of the substituted triazinyl may be at least one selected from the group consisting of a phenyl unsubstituted or substituted with a triphenylsilyl, a biphenyl, a naphthyl and a terphenyl;
  • the substituent of the substituted quinoxalinyl may be at least one selected from the
  • Xa to Xh each independently, preferably represent hydrogen, a substituted or unsubstituted (C6-C18)aryl, or a substituted or unsubstituted (6- to 20-membered)heteroaryl, or are linked to an adjacent substituent to form a substituted or unsubstituted, mono- or polycyclic, (C6-C20) aromatic ring, wherein the carbon atom(s) of the alicyclic or aromatic ring, or the combination thereof may be replaced with at least one heteroatom selected from nitrogen, oxygen, and sulfur; and more preferably represent hydrogen, a substituted or unsubstituted (C6-C15)aryl, or a (10- to 20-membered)heteroaryl unsubstituted or substituted with a (C6-C18)aryl, or are linked to an adjacent substituent to form a substituted or unsubstituted benzene ring, a substituted or unsubstituted
  • Xa to Xh each independently, represent hydrogen, a substituted or unsubstituted phenyl, an unsubstituted biphenyl, a substituted or unsubstituted carbazolyl, an unsubstituted dibenzofuranyl, or an unsubstituted dibenzothiophenyl; or are linked to an adjacent substituent to form an unsubstituted benzene ring, a substituted indene ring, a substituted indole ring, a substituted or unsubstituted benzothiophene ring, an unsubstituted benzofuran ring, or a substituted benzoindole ring.
  • the substituent of the substituted phenyl may be at least one selected from the group consisting of a carbazolyl unsubstituted or substituted with a phenyl, and a dibenzothiophenyl; the substituent of the substituted carbazolyl may be at least one selected from the group consisting of a phenyl, a biphenyl, a naphthyl and a terphenyl; the substituent of the substituted indene ring may be at least one selected from the group consisting of a methyl and a phenyl; the substituent of the substituted indole ring may be at least one selected from the group consisting of a phenyl, a naphthyl, and a biphenyl; the substituent of the benzothiophene ring may be a triazinyl substituted with at least one phenyl; and the substituent of the substituted benzoindole ring may be at least one selected from the group consist
  • A preferably represents S or CR 8 R 9 , wherein R 8 and R 9 , each independently, represent hydrogen, a substituted or unsubstituted (C1-C30)alkyl, or a substituted or unsubstituted (C6-C25)aryl, or are linked to each other to form a substituted or unsubstituted, mono- or polycyclic, (C3-C25) alicyclic or aromatic ring, or the combination thereof; preferably represent an unsubstituted (C6-C18)aryl, or are linked to each other to form an unsubstituted, mono- or polycyclic, (C3-C18) alicyclic or aromatic ring, or the combination thereof; and for example, represent a phenyl, or are linked to each other to form a fluorene ring having a spiro structure.
  • 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 any one of formulas 2 to 4 includes the following compounds, but is not limited thereto.
  • the compound represented by any one of formulas 2 to 4 of the present disclosure may be produced by a synthetic method known to one skilled in the art, but is not limited thereto.
  • 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.
  • One of the first and second electrodes may be an anode, and the other may be a cathode.
  • the organic layer may comprise at least one 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 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 light-emitting auxiliary layer may be placed between the anode and the light-emitting layer, or between the cathode and the light-emitting layer.
  • the light-emitting auxiliary layer When the light-emitting auxiliary layer is placed between the anode and the light-emitting layer, it can be used for promoting the hole injection and/or the hole transport, or for preventing the overflow of electrons.
  • the light-emitting auxiliary layer is placed between the cathode and the light-emitting layer, it can be used for promoting the electron injection and/or the electron transport, or for preventing the overflow of holes.
  • the hole auxiliary layer may be placed between the hole transport layer (or hole injection layer) and the light-emitting layer, and may be effective to promote or block the hole transport rate (or the hole injection rate), thereby enabling the charge balance to be controlled.
  • the electron blocking layer may be placed between the hole transport layer (or hole injection layer) and the light-emitting layer, and may block overflowing electrons from the light-emitting layer and confine the excitons in the light-emitting layer to prevent light leakage.
  • the hole transport layer which is further included, may be used as a hole auxiliary layer or an electron blocking layer.
  • the light-emitting auxiliary layer, the hole auxiliary layer or the electron blocking layer may have an effect of improving the efficiency and/or the lifespan of the organic electroluminescent device.
  • the organic layer comprising a combination of at least one compound represented by formula 1 and at least one compound represented by any one of formulas 2 to 4 may be provided.
  • the organic layer may be a single layer or a plurality of layers.
  • the compound represented by formula 1 and the compound represented by any one of formulas 2 to 4 may be comprised in the same layer or different layers, respectively.
  • the present disclosure provides an organic electroluminescent device comprising the organic layer.
  • the combination of the dopant and the host which is a combination of at least one dopant compound represented by formula 1 and at least one host compound represented by any one of formulas 2 to 4, may be provided.
  • the present disclosure may provide an organic electroluminescent device comprising the combination of the dopant and the host.
  • an organic electroluminescent material comprising a combination of at least one compound represented by formula 1 and at least one compound represented by any one of formulas 2 to 4, 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 any one of formulas 2 to 4, and may further comprise conventional materials comprised in an organic electroluminescent material.
  • the organic electroluminescent device of the present disclosure may comprise the compound represented by formula 1, and the compounds represented by any one of formulas 2 to 4, and may further comprise at least one compound selected from the group consisting of arylamine-based compounds and styrylarylamine-based compounds.
  • the organic layer may further comprise at least one metal selected from the group consisting of metals of Group 1, metals of Group 2, transition metals of the 4 th period, transition metals of the 5 th period, lanthanides and organic metals of d-transition elements of the Periodic Table, or at least one complex compound comprising said metal, besides the compound of formula 1, and the compound of any one of formulas 2 to 4.
  • 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 is known in the art. Also, it may further comprise a yellow or orange light-emitting layer, if necessary.
  • a layer selected from a chalcogenide layer, a metal halide layer and a metal oxide 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.
  • OLED organic light-emitting diode
  • an OLED device comprising a conventional red phosphorescent organic electroluminescent material was produced as follows: A transparent electrode indium tin oxide (ITO) thin film (10 ⁇ /sq) on a glass substrate for an OLED (GEOMATEC CO., LTD., Japan) was subjected to an ultrasonic washing with acetone, ethanol and distilled water, sequentially, and then was stored in isopropanol. Next, the ITO substrate was 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 the pressure in the chamber of the apparatus was then controlled to 10 -6 torr.
  • ITO indium tin oxide
  • Compound HT-2 was then introduced into another cell of the vacuum vapor deposition apparatus, and an electric current was applied to the cell to evaporate the introduced material, thereby forming a second hole transport layer having a thickness of 60 nm on the first hole transport layer.
  • a light-emitting layer was then deposited as follows.
  • Compound B-109 as a host was introduced into one cell of the vacuum vapor deposition apparatus and any one of the following compounds D-1 to D-6 as a dopant was introduced into another cell of the apparatus.
  • the two materials were evaporated at a different rate and the dopant was deposited in a doping amount of 2 wt%, based on the total weight 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 35 nm on the light-emitting layer.
  • an Al cathode having a thickness of 80 nm was deposited by another vacuum vapor deposition apparatus on the electron injection layer.
  • an OLED device was produced.
  • An OLED device was produced in the same manner as in Comparative Examples 1 to 6, except that compound C-4 , compound C-2 , compound C-1 , compound C-16 and compound C-21 according to the present disclosure were used respectively as a dopont.
  • the OLED devices (Device Examples 1 to 5) using the compound of the present disclosure, wherein the 6-position of isoquinoline in the ligand of the iridium (Ir) complex is substituted with a specific alkyl group according to the present disclosure, as a dopant, has an X value of the CIE 1931 colorimetric system equivalent to or at a similar level to the OLED devices (Comparative Examples 1 to 6) using a conventional compound as a dopant, the OLED devices according to the present disclosure exhibit low driving voltage and high current efficiency, thereby exhibiting a high luminance efficiency while realizing a deep red color.

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  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Inorganic Chemistry (AREA)
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  • High Energy & Nuclear Physics (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Organic Chemistry (AREA)
  • Electroluminescent Light Sources (AREA)

Abstract

La présente invention concerne un composé électroluminescent organique et un dispositif électroluminescent organique le comprenant. En comprenant le composé électroluminescent organique de la présente invention, il est possible de fournir un dispositif électroluminescent organique ayant une faible tension d'attaque et/ou des propriétés d'efficacité lumineuse élevées tout en présentant une couleur rouge profonde par comparaison avec un dispositif électroluminescent organique classique.
PCT/KR2017/015481 2016-12-27 2017-12-26 Composé électroluminescent organique et dispositif électroluminescent organique le comprenant WO2018124697A1 (fr)

Priority Applications (6)

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CN202210969683.6A CN115181135A (zh) 2016-12-27 2017-12-26 有机电致发光化合物和包含其的有机电致发光装置
JP2019530396A JP2020503672A (ja) 2016-12-27 2017-12-26 有機エレクトロルミネセント化合物及びそれを含む有機エレクトロルミネセントデバイス
CN201780075157.2A CN110036499A (zh) 2016-12-27 2017-12-26 有机电致发光化合物和包含其的有机电致发光装置
US16/462,985 US20190312218A1 (en) 2016-12-27 2017-12-26 Organic electroluminescent compound and organic electroluminescent device comprising the same
EP17886492.2A EP3563437A4 (fr) 2016-12-27 2017-12-26 Composé électroluminescent organique et dispositif électroluminescent organique le comprenant
US17/666,885 US20220165969A1 (en) 2016-12-27 2022-02-08 Organic electroluminescent compound and organic electroluminescent device comprising the same

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KR10-2016-0180012 2016-12-27
KR20160180012 2016-12-27
KR20170027214 2017-03-02
KR10-2017-0027214 2017-03-02
KR10-2017-0178000 2017-12-22
KR1020170178000A KR102359412B1 (ko) 2016-12-27 2017-12-22 유기 전계 발광 화합물 및 이를 포함하는 유기 전계 발광 소자

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US17/666,885 Continuation-In-Part US20220165969A1 (en) 2016-12-27 2022-02-08 Organic electroluminescent compound and organic electroluminescent device comprising the same

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CN110878105A (zh) * 2018-09-05 2020-03-13 三星电子株式会社 有机金属化合物、包括其的有机发光器件、和包括所述有机金属化合物的诊断组合物
JP2020186236A (ja) * 2019-05-09 2020-11-19 北京夏禾科技有限公司 ３−重水素置換イソキノリン配位子を含有する有機発光材料
DE102021100230A1 (de) 2020-01-10 2021-07-15 Beijing Summer Sprout Technology Co., Ltd. Organisches lichtemittierendes Material
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US11459348B2 (en) 2018-04-02 2022-10-04 Samsung Electronics Co., Ltd. Organometallic compound, organic light-emitting device including the same, and diagnostic composition including the organometallic compound
US11581498B2 (en) 2019-05-09 2023-02-14 Beijing Summer Sprout Technology Co., Ltd. Organic luminescent material containing 6-silyl-substituted isoquinoline ligand
US11653559B2 (en) 2019-05-09 2023-05-16 Beijing Summer Sprout Technology Co., Ltd. Metal complex containing a first ligand, a second ligand, and a third ligand
US11993617B2 (en) 2019-10-18 2024-05-28 Beijing Summer Sprout Technology Co., Ltd. Organic luminescent material having an ancillary ligand with a partially fluorine-substituted substituent

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EP3549944B1 (fr) * 2018-04-02 2021-12-29 Samsung Electronics Co., Ltd. Composé organométallique, dispositif électroluminescent organique le comprenant et composition de diagnostic comprenant le composé organométallique
US11459348B2 (en) 2018-04-02 2022-10-04 Samsung Electronics Co., Ltd. Organometallic compound, organic light-emitting device including the same, and diagnostic composition including the organometallic compound
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US11827649B2 (en) 2018-04-02 2023-11-28 Samsung Electronics Co., Ltd. Organometallic compound, organic light-emitting device including the same, and diagnostic composition including the organometallic compound
EP3604321A1 (fr) * 2018-07-31 2020-02-05 Samsung Electronics Co., Ltd. Composé organométallique, dispositif électroluminescent organique le comprenant et composition de diagnostic comprenant le composé organométallique
US11856805B2 (en) 2018-07-31 2023-12-26 Samsung Electronics Co., Ltd. Organometallic compound, organic light-emitting device including the same, and diagnostic composition including the organometallic compound
JP7249917B2 (ja) 2018-09-05 2023-03-31 三星電子株式会社 有機金属化合物とそれを含む有機発光素子及び診断用組成物
EP3620460A1 (fr) * 2018-09-05 2020-03-11 Samsung Electronics Co., Ltd. Composé organométallique, dispositif électroluminescent organique le comprenant et composition de diagnostic comprenant le composé organométallique
CN110878105A (zh) * 2018-09-05 2020-03-13 三星电子株式会社 有机金属化合物、包括其的有机发光器件、和包括所述有机金属化合物的诊断组合物
JP2020059695A (ja) * 2018-09-05 2020-04-16 三星電子株式会社Ｓａｍｓｕｎｇ Ｅｌｅｃｔｒｏｎｉｃｓ Ｃｏ．，Ｌｔｄ． 有機金属化合物とそれを含む有機発光素子及び診断用組成物
JP2020186236A (ja) * 2019-05-09 2020-11-19 北京夏禾科技有限公司 ３−重水素置換イソキノリン配位子を含有する有機発光材料
US11581498B2 (en) 2019-05-09 2023-02-14 Beijing Summer Sprout Technology Co., Ltd. Organic luminescent material containing 6-silyl-substituted isoquinoline ligand
JP7208641B2 (ja) 2019-05-09 2023-01-19 北京夏禾科技有限公司 ３－重水素置換イソキノリン配位子を含有する有機発光材料
US11653559B2 (en) 2019-05-09 2023-05-16 Beijing Summer Sprout Technology Co., Ltd. Metal complex containing a first ligand, a second ligand, and a third ligand
DE102020205833B4 (de) 2019-05-09 2022-12-22 Beijing Summer Sprout Technology Co., Ltd. Organisches lumineszierendes Material, das einen 3-Deuterium-substituierten Isochinolinliganden beinhaltet
US11498937B2 (en) 2019-05-09 2022-11-15 Beijing Summer Sprout Technology Co., Ltd. Organic luminescent material including 3-deuterium-substituted isoquinoline ligand
US11993617B2 (en) 2019-10-18 2024-05-28 Beijing Summer Sprout Technology Co., Ltd. Organic luminescent material having an ancillary ligand with a partially fluorine-substituted substituent
DE102021100230A1 (de) 2020-01-10 2021-07-15 Beijing Summer Sprout Technology Co., Ltd. Organisches lichtemittierendes Material

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